########################################################################################################################################################################################################################## Database Name: EPFL_LISP_BXD_Liver_Polar_Metabolites_CD+HFD_Jun14 GeneNetwork Accession Number: GN473 For more information regarding this data set please visit: http://www.genenetwork.org/webqtl/main.py?FormID=sharinginfo&GN_AccessionId=473 Z-Score. In general, the array data that we enter in GeneNetwork have been log transformed and then z-score normalized, but instead of leaving the mean at 0 and the standard deviation of 1 unit, the data is rescaled to a mean of 8 units with a standard deviation of 2 units (what we call 2Z + 8 normalized data). Usage Conditions and Limitations: Data sets that have been incorporated in the GeneNetwork belong to individuals, groups, and companies listed in the Status and Contacts page. 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Data providers shall not be responsible for any damage or loss of any kind arising out of or related to your use of the databases,including without limitation data loss or corruption, regardless of whether such liability is based in tort, contract, or otherwise. ########################################################################################################################################################################################################################## ProbeSet Gene Symbol Chr Mb Gene Id Strand Gene Blat Mb Start Blat Mb End Description Aliases Blat Sequence UniGeneId OMIM HomoloGeneID C57BL/6J DBA/2J BXD68 BXD43 BXD44 BXD45 BXD48 BXD49 BXD50 BXD51 BXD55 BXD56 BXD60 BXD61 BXD62 BXD63 BXD64 BXD65 BXD66 BXD69 BXD70 BXD71 BXD73 BXD75 BXD79 BXD81 BXD83 BXD84 BXD85 BXD87 BXD89 BXD90 BXD98 BXD95 BXD99 BXD100 BXD101 BXD103 BXD97 BXD80 BXD92 BXD96 51.02407804_MZ Methanol Un 1.0 None None None None Methanol is the simplest alcohol, and is a light, volatile, colourless, flammable, poisonous liquid with a distinctive odor that is somewhat milder and sweeter than ethanol (Wikipedia). Methanol is responsible for accidental, suicidal, and epidemic poisonings, resulting in death or permanent sequelae. Toxicity is due to the metabolic products of alcohol dehydrogenase (ADH) and aldehyde dehydrogenase. (PMID 15627163). The rapid and accurate diagnosis of toxic alcohol poisoning due to methanol (methyl alcohol) is paramount in preventing serious adverse outcomes. The quantitative measurement of specific serum levels of methanol using gas chromatography is expensive, time consuming and generally only available at major tertiary-care facilities. (PMID 15862085). CH4O None None None 4164.36 4415.39 4457.15 3467.02 4372.0 6234.15 5158.01 3872.71 6478.56 5512.44 4926.18 4777.77 4330.23 4323.88 4477.22 4651.46 3428.56 4703.18 5010.05 4598.0 4955.95 5627.21 5308.9 4454.17 4277.65 4522.44 4201.2 4063.03 5439.21 4957.01 3258.59 4129.05 4958.22 4250.11 4892.01 5011.07 5304.27 4315.8 3284.2 5374.09 3987.87 5185.5 52.02081441_MZ Hydroxylamine Un 1.0 None None None None Hydroxylamine is a reactive chemical with formula NH2OH. It can be considered a hybrid of ammonia and water due to parallels it shares with each. At room temperature pure NH2OH is ordinarily a white, unstable crystalline, hygroscopic compound; however it is almost always encountered as an aqueous solution. A colorless inorganic compound (HONH2) used in organic synthesis and as a reducing agent, due to its ability to donate nitric oxide. Hydroxylamine may explode on heating. It is an irritant to the respiratory tract, skin, eyes, and other mucous membranes. It may be absorbed through the skin, is harmful if swallowed, and is a possible mutagen. NH2OH is an intermediate in the biological nitrification. The oxidation of NH3 is mediated by HAO (hydroxylamine oxidoreductase). H3NO None None None 993.512 951.321 1016.58 987.435 751.626 913.796 1081.51 1114.01 991.447 1124.96 1184.29 563.476 1331.43 694.998 787.63 990.844 702.626 445.8 913.797 987.236 846.414 1402.28 897.803 1100.58 921.215 746.646 604.449 1265.67 1238.4 749.435 528.692 570.212 1044.51 1004.15 1137.3 1002.12 998.712 632.796 723.666 945.02 1118.99 700.726 53.00263058_MZ 2-Propyn-1-al Un 1.0 None None None None 2-Propyn-1-al is involved in the propanoate metabolism system. It is created from 2-Propyn-1-ol through the action of alcohol dehydrogenase [EC:1.1.99.8]. 2-Propyn-1-al is converted to propynoate by aldehyde dehydrogenase [EC:1.2.1.3]. C3H2O None None None 725.697 706.766 823.308 778.586 840.702 935.828 990.881 899.302 956.395 1018.02 780.944 604.027 943.785 874.378 895.517 951.508 740.09 1292.89 927.2 816.139 602.204 871.263 835.131 922.521 990.556 1173.22 605.903 712.734 614.791 1065.0 871.599 1172.98 913.981 712.634 1095.9 972.591 901.805 1096.87 737.391 889.72 1038.16 757.622 54.97564605_MZ Hydrochloric acid Un 1.0 None None None None Hydrochloric acid constitutes the majority of gastric acid, the human digestive fluid. In a complex process and at a large energetic burden, it is secreted by parietal cells (also known as oxyntic cells). These cells contain an extensive secretory network (called canaliculi) from which the HCl is secreted into the lumen of the stomach. They are part of the epithelial fundic glands (also known as oxyntic glands) in the stomach. The chemical compound hydrochloric acid is the aqueous (water-based) solution of hydrogen chloride gas (HCl). It is a strong acid, the major component of gastric acid and of wide industrial use. Hydrochloric acid must be handled with appropriate safety precautions because it is a highly corrosive liquid. Hydrochloric acid, or muriatic acid by its historical but still occasionally used name, has been an important and frequently used chemical from early history and was discovered by the alchemist Jabir ibn Hayyan around the year 800. Hydrogen chloride, also known under the name HCl, is a highly corrosive and toxic colorless gas that forms white fumes on contact with humidity. These fumes consist of hydrochloric acid which forms when hydrogen chloride dissolves in water. The hydrogen chloride molecule HCl is a simple diatomic molecule consisting of a hydrogen atom H and a chlorine atom Cl connected with a covalent single bond. Since the chlorine atom is much more electronegative than the hydrogen atom, the covalent bond between the atoms is quite polar. Hydrogen chloride forms corrosive hydrochloric acid on contact with body tissue. Inhalation of the fumes can cause coughing, choking, inflammation of the nose, throat, and upper respiratory tract, and in severe cases, pulmonary edema, circulatory system failure, and death. Skin contact can cause redness, pain, and severe skin burns. Hydrogen chloride may cause severe burns to the eye and permanent eye damage. ClH None None None 915.772 671.219 1136.08 1529.5 1257.83 921.328 603.559 1113.09 1048.13 1364.11 905.482 1530.18 873.83 1139.5 745.656 1181.06 1284.81 782.151 890.244 889.274 1077.59 731.753 1049.94 1013.57 1210.04 1086.82 974.053 908.354 573.753 843.243 639.569 1561.69 885.653 1577.26 810.777 519.651 1177.16 1230.44 583.492 933.379 1326.3 837.026 57.03446253_MZ Acetone Un 1.0 None None None None Acetone is one of the ketone bodies produced during ketoacidosis. Acetone is not regarded as a waste product of metabolism. However, its physiological role in biochemical machinery is not clear. A model for the role of acetone metabolism is presented that orders the events occurring in acetonemia in sequence: in diabetic ketosis or starvation, ketone body production (b-hydroxy-butyrate, acetoacetate) provides fuel for vital organs (heart, brain .) raising the chance of survival of the metabolic catastrophe. However, when ketone body production exceeds the degrading capacity, the accumulating acetoacetic acid presents a new challenge to the pH regulatory system. Acetone production and its further degradation to C3 fragments fulfill two purposes: the maintenance of pH buffering capacity and provision of fuel for peripheral tissues. Since ketosis develops under serious metabolic circumstances, all the mechanisms that balance or moderate the effects of ketosis enhance the chance for survival. From this point of view, the theory that transportable C3 fragments can serve as additional nutrients is a novel view of acetone metabolism which introduces a new approach to the study of acetone degradation, especially in understanding its physiological function and the interrelationship between liver and peripheral tissues. (PMID 10580530). Acetone is typically derived from acetoacetate through the action of microbial acetoacetate decarboxylases found in gut microflora. In chemistry, acetone is the simplest representative of the ketones. Acetone is a colorless, mobile, flammable liquid readily soluble in water, ethanol, ether, etc., and itself serves as an important solvent. Acetone is an irritant and inhalation may lead to hepatotoxic effects (causing liver damage). C3H6O, Propanal None None None 36063.8 40283.9 39012.8 38479.3 42177.8 50609.1 39167.9 32970.2 38948.7 43995.3 43483.1 40828.4 27301.6 47942.4 49378.7 36281.3 35455.2 28853.0 35907.9 32813.2 37298.0 38043.2 39616.6 37469.8 36583.3 35225.2 41222.0 33888.3 34710.7 50620.5 34560.7 36546.4 37954.3 32222.1 38505.0 36322.9 32999.4 39217.1 27435.2 38831.5 27886.1 29146.9 58.02967943_MZ N-Methylformamide Un 1.0 None None None None N-Methylformamide (NMF) is one of the two major urinary biomarkers of exposure to N,N-Dimethylformamide (DMF), a compound widely used in industries because of its extensive miscibility with water and solvents. Metabolism of NMF results in the formation of N-methylcarbamoyl adducts at the N-terminal valine and lysine in blood protein globin. (PMID: 17254560, 17254560, 16289959). C2H5NO, Acetaldehyde oxime None None None 3569.27 2876.21 3115.65 2675.1 2829.25 2957.11 2853.28 2906.72 2704.14 3036.88 2637.59 2403.52 2656.83 3084.41 2336.26 3426.51 2740.87 3043.21 2922.18 2612.49 3350.17 2308.26 2759.5 2511.86 3171.92 2637.06 3269.58 2471.43 3460.44 2340.89 3063.97 3518.79 2777.28 2264.48 3164.58 3169.48 2899.2 2208.74 2674.2 2554.83 2930.23 3059.91 59.01373236_MZ Acetic acid Un 1.0 None None None None Acetic acid is one of the simplest carboxylic acids. It is an important chemical reagent and industrial chemical that is used in the production of plastic soft drink bottles, photographic film; and polyvinyl acetate for wood glue, as well as many synthetic fibres and fabrics. In households diluted acetic acid is often used as a cleaning agent. In the food industry acetic acid is used as an acidity regulator. The acetyl group, derived from acetic acid, is fundamental to the biochemistry of virtually all forms of life. When bound to coenzyme A it is central to the metabolism of carbohydrates and fats. However, the concentration of free acetic acid in cells is kept at a low level to avoid disrupting the control of the pH of the cell contents. Acetic acid is produced and excreted by certain bacteria, notably the Acetobacter genus and Clostridium acetobutylicum. These bacteria are found universally in foodstuffs, water, and soil, and acetic acid is produced naturally as fruits and some other foods spoil. Acetic acid is also a component of the vaginal lubrication of humans and other primates, where it appears to serve as a mild antibacterial agent. C2H4O2, Glycolaldehyde None None None 84209.5 90056.9 96006.6 99257.3 92619.2 106179.0 93983.7 82835.5 86402.4 94459.9 78669.5 89900.6 108617.0 73150.1 101886.0 99937.1 81967.2 114429.0 101879.0 101971.0 85717.7 87577.4 91177.9 93801.6 96657.6 92834.4 98406.9 94965.3 99175.8 75514.8 82695.6 104727.0 91112.9 85721.3 96096.8 106838.0 93366.9 83655.1 68634.4 103412.0 92002.5 95411.5 59.05011986_MZ Propyl alcohol Un 1.0 None None None None C3H8O, Isopropyl alcohol None None None 4688.49 5312.33 4539.25 4987.15 4382.32 4351.61 4235.31 4791.1 4499.39 4795.78 4991.98 4401.22 4346.94 4342.48 4633.27 4754.43 4643.4 4485.0 4247.0 4444.88 4744.52 4864.89 4754.5 4899.88 4388.13 4506.49 4427.86 4999.64 4868.33 4891.6 4701.19 4569.65 3975.97 4461.52 5265.52 4976.9 4209.84 4490.76 4153.89 4899.37 4027.1 4424.13 64.01869394_MZ Formamide Un 1.0 None None None None Formamide is a metabolite used for biological monitoring of workers exposed to N-N-dimethylformamide (DMF).(PMID 7622279). There is a case of significant association between ever having been exposed to DMF and subsequent development of prostate cancer (PMID 2715850). CH3NO None None None 1705.97 1341.37 1217.76 1232.8 1376.19 1361.83 1135.95 1119.71 915.576 1268.29 1038.67 1219.2 1073.39 969.022 1209.09 1447.13 1196.84 1396.54 1323.83 835.141 1011.07 1217.25 1487.41 1334.76 1288.64 1254.23 1126.76 1337.45 1651.75 1011.48 1151.79 1476.06 1611.13 1457.34 1260.07 1324.69 1039.52 1727.53 870.405 1379.21 994.722 1044.17 65.03921071_MZ Ethanol Un 1.0 None None None None Ethanol is a clear, colorless liquid rapidly absorbed from the gastrointestinal tract and distributed throughout the body. It has bactericidal activity and is used often as a topical disinfectant. It is widely used as a solvent and preservative in pharmaceutical preparations as well as serving as the primary ingredient in alcoholic beverages. Indeed, ethanol has widespread use as a solvent of substances intended for human contact or consumption, including scents, flavorings, colorings, and medicines. Ethanol has a depressive effect on the central nervous system and because of its psychoactive effects, it is considered a drug. Ethanol has a complex mode of action and affects multiple systems in the brain, most notably it acts as an agonist to the GABA receptors. Death from ethanol consumption is possible when blood alcohol level reaches 0.4%. A blood level of 0.5% or more is commonly fatal. Levels of even less than 0.1% can cause intoxication, with unconsciousness often occurring at 0.3-0.4 %. Ethanol is metabolized by the body as an energy-providing carbohydrate nutrient, as it metabolizes into acetyl CoA, an intermediate common with glucose metabolism, that can be used for energy in the citric acid cycle or for biosynthesis. Ethanol within the human body is converted into acetaldehyde by alcohol dehydrogenase and then into acetic acid by acetaldehyde dehydrogenase. The product of the first step of this breakdown, acetaldehyde, is more toxic than ethanol. Acetaldehyde is linked to most of the clinical effects of alcohol. It has been shown to increase the risk of developing cirrhosis of the liver,[77] multiple forms of cancer, and alcoholism. Industrially, ethanol is produced both as a petrochemical, through the hydration of ethylene, and biologically, by fermenting sugars with yeast. Small amounts of ethanol are endogenously produced by gut microflora through anaerobic fermentation. However most ethanol detected in biofluids and tissues likely comes from consumption of alcoholic beverages. Absolute ethanol or anhydrous alcohol generally refers to purified ethanol, containing no more than one percent water. Absolute alcohol is not intended for human consumption. It often contains trace amounts of toxic benzene (used to remove water by azeotropic distillation). Consumption of this form of ethanol can be fatal over a short time period. Generally absolute or pure ethanol is used as a solvent for lab and industrial settings where water will disrupt a desired reaction. Pure ethanol is classed as 200 proof in the USA and Canada, equivalent to 175 degrees proof in the UK system. C2H6O None None None 1117.35 1161.19 1239.73 1324.71 1321.74 1351.72 1061.13 1302.56 1166.95 1005.95 1413.63 1117.0 807.534 1255.41 1603.38 1431.99 909.954 1353.44 958.044 1236.85 1018.34 1119.76 1204.48 1015.36 1074.97 1095.1 1357.27 1106.67 1080.18 1089.26 1077.02 808.224 1241.18 1110.38 850.981 980.72 1149.49 1111.34 916.663 1373.81 801.451 958.825 67.01885406_MZ 3-Butyn-1-al Un 1.0 None None None None 3-Butyn-1-al is an intermediate in Butanoate metabolism (KEGG ID C06145). It is the third to last step in the synthesis and degradation of ketone bodies and is converted from 3-Butyn-1-ol via the enzyme alcohol dehydrogenase (acceptor) [EC:1.1.99.8]. It is then converted to 3-Butynoate via the enzyme aldehyde dehydrogenase (NAD+) [EC:1.2.1.3]. C4H4O None None None 5366.58 4843.37 5745.88 4521.28 5967.68 6085.63 5879.44 5888.7 6250.28 5734.17 5834.5 5752.66 6339.79 6181.99 6064.84 4306.39 5718.79 5590.62 6038.61 5718.59 5415.84 5982.69 5948.04 5443.98 5678.2 5382.21 5739.97 5142.46 5540.78 5769.33 4827.18 4618.73 5706.1 5696.12 5983.68 5312.21 5949.31 5747.21 5779.49 5622.02 4948.86 5720.05 67.02953357_MZ Imidazole Un 1.0 None None None None Imidazole is a heterocyclic aromatic organic compound. It is further classified as an alkaloid. Imidazole refers to the parent compound C3H4N2, while imidazoles are a class of heterocycles with similar ring structure but varying substituents. This ring system is present in important biological building blocks such as histidine and histamine. Imidazole can act as a base and as a weak acid. Imidazole exists in two tautomeric forms with the hydrogen atom moving between the two nitrogens. Many drugs contain an imidazole ring, such as antifungal drugs and nitroimidazole. Imidazole is a 5 membered planar ring which is soluble in water and polar solvents. Imidazole is a base and an excellent nucleophile. It reacts at the NH nitrogen, attacking alkylating and acylating compounds. It is not particularly susceptible to electrophilic attacks at the carbon atoms, and most of these reactions are substitutions that keep the aromaticity intact. One can see from the resonance structure that the carbon-2 is the carbon most likely to have a nucleophile attack it, but in general nucleophilic substitutions are difficult with imidazole. Imidazole is incorporated into many important biological molecules. The most obvious is the amino acid histidine, which has an imidazole side chain. histidine is present in many proteins and enzymes and plays a vital part in the structure and binding functions of hemoglobin. C3H4N2 None None None 3963.32 3362.3 3878.71 3949.34 3588.64 4153.6 3497.66 4181.27 3906.16 3544.17 4178.02 3987.79 4435.94 3751.14 3800.03 4030.96 3895.82 4577.88 4092.29 3560.37 3746.26 4148.02 4072.14 4008.43 3697.27 3779.07 3371.34 3390.24 4092.7 3940.26 3401.48 3542.64 3925.58 4115.29 4416.47 4163.79 4022.67 3682.86 4296.42 3644.04 3514.22 4258.06 70.02977243_MZ Acrylamide Un 1.0 None None None None Acrylamide (ACR) is a chemical used in many industries around the world and more recently was found to form naturally in foods cooked at high temperatures. Acrylamide is a neurotoxicant, reproductive toxicant, and carcinogen in animal species. Only the neurotoxic effects have been observed in humans and only at high levels of exposure in occupational settings. The mechanism underlying neurotoxic effects of ACR may be basic to the other toxic effects seen in animals. This mechanism involves interference with the kinesin-related motor proteins in nerve cells or with fusion proteins in the formation of vesicles at the nerve terminus and eventual cell death. Neurotoxicity and resulting behavioral changes can affect reproductive performance of ACR-exposed laboratory animals with resulting decreased reproductive performance. Further, the kinesin motor proteins are important in sperm motility, which could alter reproduction parameters. Effects on kinesin proteins could also explain some of the genotoxic effects on ACR. These proteins form the spindle fibers in the nucleus that function in the separation of chromosomes during cell division. This could explain the clastogenic effects of the chemical noted in a number of tests for genotoxicity and assays for germ cell damage. Other mechanisms underlying ACR-induced carcinogenesis or nerve toxicity are likely related to an affinity for sulfhydryl groups on proteins. Binding of the sulfhydryl groups could inactive proteins/enzymes involved in DNA repair and other critical cell functions. Direct interaction with DNA may or may not be a major mechanism for cancer induction in animals. The DNA adducts that form do not correlate with tumor sites and ACR is mostly negative in gene mutation assays except at high doses that may not be achievable in the diet. All epidemiologic studies fail to show any increased risk of cancer from either high-level occupational exposure or the low levels found in the diet. In fact, two of the epidemiologic studies show a decrease in cancer of the large bowel. A number of risk assessment studies were performed to estimate increased cancer risk. The results of these studies are highly variable depending on the model. There is universal consensus among international food safety groups in all countries that examined the issue of ACR in the diet that not enough information is available at this time to make informed decisions on which to base any regulatory action. Too little is known about levels of this chemical in different foods and the potential risk from dietary exposure. Avoidance of foods containing ACR would result in worse health issues from an unbalanced diet or pathogens from under cooked foods. There is some consensus that low levels of ACR in the diet are not a concern for neurotoxicity or reproductive toxicity in humans, although further research is need to study the long-term, low-level cumulative effects on the nervous system. Any relationship to cancer risk from dietary exposure is hypothetical at this point and awaits more definitive studies. (PMID: 17492525). C3H5NO None None None 4797.68 4820.93 3725.8 3759.14 4910.19 4639.95 4617.25 4689.33 3632.32 3630.61 3808.66 2954.58 3641.15 4755.44 4449.4 4684.75 4388.52 4554.66 4678.38 8956.41 3954.02 3762.0 4496.18 4263.5 4124.11 4094.41 4538.61 3912.27 3909.26 4474.05 11093.7 3862.39 3511.72 8042.7 3740.67 5081.73 3677.15 3614.7 5490.74 4568.12 13090.8 4200.57 71.01382126_MZ Pyruvaldehyde Un 1.0 None None None None Pyruvaldehyde is an organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals. C3H4O2, Malondialdehyde None None None 118428.0 124114.0 122058.0 88273.4 142599.0 118323.0 131988.0 162646.0 123443.0 107843.0 127056.0 134236.0 137775.0 104055.0 145946.0 115324.0 118831.0 102256.0 125537.0 130389.0 129120.0 139707.0 125917.0 137613.0 129175.0 131069.0 143222.0 125361.0 132366.0 97509.1 128025.0 135611.0 112151.0 103863.0 132696.0 123702.0 105108.0 139270.0 95489.3 149651.0 113571.0 120543.0 71.04981752_MZ Butanal Un 1.0 None None None None Butanal is an organic compound that is the aldehyde analog of butane. It is a colorless flammable liquid with an acrid smell. It is miscible with most organic solvents.(wikipedia). IN man, butanal is a biomarker for oxidative damage to lipids, proteins and DNA. (PubMed ID 15763951 ). C4H8O, Butanone, tetrahydrofuran None None None 2750.51 2398.29 2889.11 3222.97 3555.01 2927.27 2353.57 3234.91 2894.8 2909.94 2915.98 2979.06 1484.84 3482.95 3009.22 2354.93 3622.09 2133.98 2792.12 2073.15 2521.43 3109.68 2475.49 3084.74 3145.6 4023.81 3002.9 2510.83 3037.86 2973.64 2254.74 2517.72 3273.68 2993.12 2435.55 2689.03 2872.32 2587.33 3322.77 2943.5 1898.14 1876.85 72.04493457_MZ Aminoacetone Un 1.0 None None None None Threonine dehydrogenase catalyzes the oxidation of threonine by NAD+ to glycine and acetyl-CoA, but when the ratio acetyl-CoA/CoA increases in nutritional deprivation (e.g., in diabetes) the enzyme produces aminoacetone (Chem. Res. Toxicol., 14 (9), 1323 -1329, 2001). Aminoacetone is thought to be a substrate for SSAO (semicarbazide-sensitive amine oxidase), leading to the production of the toxic product methylglyoxal (Journal of Chromatography B. Volume 824, Issues 1-2 , 25 September 2005, Pages 116-122 ). C3H7NO, 3-Aminopropionaldehyde None None None 3762.65 3182.45 3520.07 3694.4 3693.66 3889.55 3468.78 3275.72 3908.5 3148.59 3771.11 2952.07 3524.04 3218.97 3745.96 3575.51 3272.95 3987.37 3545.94 3295.89 3882.73 4016.96 4311.92 3576.89 3374.54 3343.54 3885.03 2997.32 4140.94 4306.31 3704.94 3445.88 4431.78 3590.0 3557.21 4319.37 3901.93 4271.27 2428.96 3338.55 3258.8 3435.39 72.99314123_MZ Glyoxylic acid Un 1.0 None None None None Glyoxylic acid or oxoacetic acid is an organic compound that is both an aldehyde and a carboxylic acid. Glyoxylic acid is a liquid with a melting Point of -93 degree centigrade and a boiling Point of 111 degree centigrade. It is an intermediate of the glyoxylate cycle, which enables certain organisms to convert fatty acids into carbohydrates. The conjugate base of gloxylic acid is known as glyoxylate. This compound is an intermediate of the glyoxylate cycle, which enables organisms, such as bacteria, fungi and plants to convert fatty acids into carbohydrates. Glyoxylate is the byproduct of the amidation process in biosynthesis of several amidated peptides. The glyoxylate cycle is a metabolic pathway occurring in plants, and several microorganisms, such as E. coli and yeast. Recent research shows that it is present in vertebrates (including humans) and insects. The glyoxylate cycle allows these organisms to use fats for the synthesis of carbohydrates. [PMID: 16396466]. C2H2O3 None None None 15201.8 15727.6 14932.4 12503.9 17239.0 12979.6 15799.5 20114.5 14008.2 13517.5 15697.2 17045.7 14417.8 14180.9 16630.2 13380.1 15428.7 9713.8 13624.1 13952.9 14914.7 16629.0 14824.2 16921.5 14456.3 16238.5 16822.0 13805.5 14123.9 12456.4 16310.3 15546.1 13272.8 13287.8 16909.7 13061.5 13903.2 17346.4 12318.2 17117.4 12529.9 14091.0 73.02946956_MZ Propionic acid Un 1.0 None None None None Propionic acid (PA) is widely used as an antifungal agent in food. It is present naturally at low levels in dairy products and occurs ubiquitously, together with other short-chain fatty acids (SCFA), in the gastro-intestinal tract of humans and other mammals as an end-product of the microbial digestion of carbohydrates. It has significant physiological activity in animals. PA is irritant but produces no acute systemic effects and has no demonstrable genotoxic potential. (PMID 1628870) Propionic aciduria is one of the most frequent organic acidurias, a disease that comprise many various disorders. The outcome of patients born with Propionic aciduria is poor intellectual development patterns, with 60% having an IQ less than 75 and requiring special education. Successful liver and/or renal transplantations, in a few patients, have resulted in better quality of life but have not necessarily prevented neurological and various visceral complications. These results emphasize the need for permanent metabolic follow-up whatever the therapeutic strategy. (PMID 15868474) Decreased early mortality, less severe symptoms at diagnosis, and more favorable short-term neurodevelopmental outcome were recorded in patients identified through expanded newborn screening. (PMID 16763906). C3H6O2, Lactaldehyde, Hydroxyacetone, D-Lactaldehyde, 3-Hydroxypropanal None None None 55438.5 65945.5 56839.8 37257.6 65715.3 63936.4 57144.0 60214.6 65173.3 61659.0 64158.5 66462.2 62325.5 53332.5 63431.3 60108.0 49571.9 71707.1 65759.4 55082.4 60062.6 63668.4 60089.3 64375.3 53771.3 63891.9 61761.7 70258.1 62603.4 58512.9 49204.9 59097.4 64527.1 55336.0 65284.4 68017.7 61198.4 62549.0 46805.1 71563.8 52046.2 65219.8 73.06727298_MZ 1-Butanol Un 1.0 None None None None 1-Butanol, which is also known as n-butanol or 1-butanol or butyl alcohol (sometimes also called biobutanol when produced biologically), is an alcohol with a 4 carbon structure and the molecular formula of C4H10O. It is primarily used as a solvent, as an intermediate in chemical synthesis, and as a fuel. There are four isomeric structures for butanol. The straight chain isomer with the alcohol at an internal carbon is sec-butanol or 2-butanol. The branched isomer with the alcohol at a terminal carbon is isobutanol, and the branched isomer with the alcohol at the internal carbon is tert-butanol. 1-Butanol is produced in small amounts by gut microbial fermenetation through the butanoate metabolic pathway. C4H10O, Isobutanol, 2-Butanol None None None 1990.95 1873.86 1764.2 2017.57 1529.69 1720.9 1544.32 1433.43 1728.7 2067.35 1684.74 1740.71 1969.4 1733.64 1685.66 1762.67 1871.35 2156.4 2057.96 1707.72 1769.26 1844.67 1766.69 1670.35 1675.09 1755.02 1576.14 1693.74 1943.0 1847.44 1763.63 1666.33 1680.84 1976.99 1980.61 1805.89 2392.91 1968.93 2550.67 1850.45 1751.12 1964.01 74.02469911_MZ Glycine Un 1.0 None None None None Glycine is a simple, nonessential amino acid, although experimental animals show reduced growth on low-glycine diets. The average adult ingests 3 to 5 grams of glycine daily. Glycine is involved in the body's production of DNA, phospholipids and collagen, and in release of energy. Glycine levels are effectively measured in plasma in both normal patients and those with inborn errors of glycine metabolism. (http://www.dcnutrition.com/AminoAcids/) Nonketotic hyperglycinaemia (OMIM 606899) is an autosomal recessive condition caused by deficient enzyme activity of the glycine cleavage enzyme system (EC 2.1.1.10). The glycine cleavage enzyme system comprises four proteins: P-, T-, H- and L-proteins (EC 1.4.4.2, EC 2.1.2.10 and EC 1.8.1.4 for P-, T- and L-proteins). Mutations have been described in the GLDC (OMIM 238300), AMT (OMIM 238310), and GCSH (OMIM 238330) genes encoding the P-, T-, and H-proteins respectively. The glycine cleavage system catalyses the oxidative conversion of glycine into carbon dioxide and ammonia, with the remaining one-carbon unit transferred to folate as methylenetetrahydrofolate. It is the main catabolic pathway for glycine and it also contributes to one-carbon metabolism. Patients with a deficiency of this enzyme system have increased glycine in plasma, urine and cerebrospinal fluid (CSF) with an increased CSF: plasma glycine ratio. (PMID 16151895). C2H5NO2 None None None 88924.6 65177.1 55398.9 62450.4 55682.2 75419.7 76946.8 70599.1 39497.4 43778.0 52567.0 38268.4 100571.0 52069.1 42965.9 102506.0 51451.6 97639.1 59987.4 81948.5 80843.7 31182.1 61054.1 66192.7 67861.6 39013.5 71430.6 62080.8 43310.5 54430.4 87353.7 75694.6 34661.6 48730.4 37572.7 60869.6 44125.3 38213.4 39433.8 55114.9 82763.2 75523.7 75.00881472_MZ Glycolic acid Un 1.0 None None None None Glycolic acid (or hydroxyacetic acid) is the smallest alpha-hydroxy acid (AHA). In its pure form, glycolic acid is a colorless crystalline solid. Due to its excellent capability to penetrate skin, glycolic acid finds applications in skin care products, most often as a chemical peel. Glycolic acid is also used for tattoo removal. C2H4O3 None None None 13752.7 14432.1 12647.3 12766.6 11169.9 13352.7 10379.4 11783.6 16020.0 13014.4 13363.8 16569.3 8789.89 15115.5 13071.6 9406.82 12108.2 11150.0 10135.6 10093.7 12384.1 15202.2 11490.3 12946.7 10193.9 13863.6 10851.1 11930.7 12525.3 15696.8 9796.5 9432.56 13780.3 10979.2 16613.2 12231.1 13518.6 14956.5 9469.45 11698.8 7834.41 10308.0 75.04456014_MZ (S)-Propane-1,2-diol Un 1.0 None None None None (S)-Propane-1,2-diol is a clear, colorless, viscous organic solvent and diluent used in pharmaceutical preparations. C3H8O2 None None None 2194.88 2610.49 1668.71 1939.78 1965.98 2092.23 1826.94 1869.46 2174.99 2168.08 1894.05 1853.02 3037.84 2225.71 1932.94 2320.36 2271.3 2367.0 2163.11 2237.74 2072.73 2064.13 2198.15 1977.75 1883.02 2212.22 2126.22 1845.82 2465.66 2026.67 2088.15 2090.29 2440.79 1917.54 2093.56 1985.05 2126.29 2235.67 2022.38 2084.15 1819.26 2174.86 77.00754023_MZ Dimethyl sulfoxide Un 1.0 None None None None Dimethyl sulfoxide (DMSO) is a key dipolar aprotic solvent. It is less toxic than other members of this class: dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, HMPA. Dimethyl sulfoxide is the chemical compound (CH3)2SO. This colorless liquid is an important dipolar aprotic solvent. It is readily miscible in a wide range of organic solvents as well as water. It has a distinctive property of penetrating the skin very readily, allowing the handler to taste it. Some describe it as an oyster-like taste, others claim it tastes like garlic. DMSO is also employed as a rinsing agent in the electronics industry and, in its deuterated form (DMSO-d6), is a useful solvent in NMR due to its ability to dissolve a wide range of chemical compounds and its minimal interference with the sample signals. In cryobiology DMSO has been used as a cryoprotectant and is still an important constituent of cryoprotectant vitrification mixtures used to preserve organs, tissues, and cell suspensions. It is particularly important in the freezing and long-term storage of embryonic stem cells and hematopoietic stem cell, which are often frozen in a mixture of 10% DMSO and 90% fetal calf serum. As part of an autologous bone marrow transplant the DMSO is re-infused along with the patient's own hematopoietic stem cell. Dimethyl sulfoxide is a by-product of wood pulping. One of the leading suppliers of DMSO is the Gaylord company in the USA. DMSO is frequently used as solvent in a number of chemical reactions. In particular it is an excellent reaction solvent for SN2 alkylations: it is possible to alkylate indoles with very high yields using potassium hydroxide as the base and a similar reaction also occurs with phenols. DMSO can be reacted with methyl iodide to form a sulfoxonium ion which can be reacted with sodium hydride to form a sulfur ylide. The methyl groups of DMSO are somewhat acidic in character (pKa=35) due to the stabilization of the resultant anions by the sulfoxide group. C2H6OS None None None 2847.89 2549.01 2631.03 2936.83 2473.74 3116.32 2267.48 2722.09 2626.11 2507.16 2775.76 2472.31 2916.26 2967.17 2606.02 2323.33 2874.68 2501.01 2537.26 2638.29 2417.24 2534.17 2951.47 2620.16 2503.75 2627.34 2818.9 2679.02 2776.92 2964.73 2505.52 2243.24 2775.26 3036.98 2599.11 3020.0 3050.11 2583.36 2820.56 2361.97 2870.95 2678.01 77.03962129_MZ Benzene Un 1.0 None None None None Benzene is a toxic, volatile, flammable liquid hydrocarbon biproduct of coal distillation. Chronic benzene exposure produces hematotoxicity, bone marrow dysplasia (Displasia is a pre-neoplastic or pre-cancerous change). (PMID 16183116). It is used as an industrial solvent in paints, varnishes, lacquer thinners, gasoline, etc. Benzene causes central nervous system damage acutely and is carcinogenic. It was formerly used as parasiticide. C6H6 None None None 5935.47 5898.85 4995.49 5236.85 5086.63 6627.62 8661.6 7741.37 3033.34 4833.3 3972.85 2149.59 5963.1 5707.26 6075.68 4749.07 8677.89 7310.26 5925.84 7342.26 4707.92 2331.03 4417.28 6775.02 4968.83 2340.18 5430.27 5364.8 2337.17 5819.62 6584.71 4577.03 1907.43 6194.91 2384.7 6088.59 3280.96 1709.82 3789.49 5565.09 7297.51 5914.26 78.03521821_MZ Pyridine Un 1.0 None None None None Pyridine is a clear liquid with an odor that is sour, putrid, and fish-like. It is a relatively simple heterocyclic aromatic organic compound that is structurally related to benzene, with one CH group in the six-membered ring replaced by a nitrogen atom. Pyridine is obtained from crude coal tar or is synthesized from acetaldehyde, formaldehyde and ammonia. Pyridine is often used as a denaturant for antifreeze mixtures, for ethyl alcohol, for fungicides, and as a dyeing aid for textiles. It is a harmful substance if inhaled, ingested or absorbed through the skin. In particular, it is known to reduce male fertility and is considered carcinogenic. Common symptoms of acute exposure to pyridine include: headache, coughing, asthmatic breathing, laryngitis, nausea and vomiting. -- Wikipedia. C5H5N None None None 924.078 575.647 611.016 581.437 708.067 832.404 702.043 508.568 569.634 925.494 866.098 603.311 476.673 963.185 583.136 545.743 346.806 608.871 658.441 587.123 625.869 642.565 601.721 688.11 583.132 705.438 596.904 797.194 543.647 908.282 549.147 663.477 512.549 630.087 522.284 690.543 661.676 788.461 684.721 639.173 667.559 726.64 83.05001724_MZ 3-Methyl-2-butenal Un 1.0 None None None None 3-Methyl-2-butenal is derivative of acrolein that is an alpha, beta unsaturated carbonyl metabolite. It can be formed endogenously during lipid peroxidation or after oxidative stress, and is considered to play an important role in human carcinogenesis. The endogenously formed acroleins are a constant source of DNA damage, can lead to mutation and can also induce tumors in humans. (PMID: 8319634). 3-methyl-2-butenal, which is an unsaturated aldehyde bearing substitution at the alkene terminus, is a poor inactivator of the enzymes protein tyrosine phosphatases (PTPs). The inactivation of PTPs can yield profound biological consequences arising from the disruption of cellular signaling pathways (PMID: 17655273). C5H8O, Methyl propenyl ketone None None None 3611.25 3921.0 4026.68 4365.62 4226.1 3790.05 3702.4 3847.81 3537.98 3709.89 4149.82 3461.4 3070.27 3999.16 4077.85 3181.56 4429.71 2530.92 3219.54 3521.41 3433.03 3488.15 3501.34 3763.03 3591.8 3305.2 3967.39 3641.06 3104.22 4054.06 2742.04 3227.31 3112.08 3421.45 3398.57 3581.84 3448.13 3481.38 3246.24 4158.19 2733.87 3349.61 84.04546797_MZ 2-Pyrrolidinone Un 1.0 None None None None 2-Pyrrolidinone is a lactam cyclization product of gamma-aminobutyric acid (GABA). (PMID 10332870). Vigabatrin (VGB, an antiepileptic drug) increases human brain gamma-aminobutyric acid (GABA) and the related metabolites, including 2-pyrrolidinone. Patients taking VGB are expected to have an increase of these metabolites. (PMID 10403220, 10840398). 2-Pyrrolidone is an organic compound consisting of a five-membered lactam. It is a colorless liquid which is used in industrial settings as a high-boiling non-corrosive polar solvent for a wide variety of applications. It is miscible with a wide variety of other solvents including water, ethanol, diethyl ether, chloroform, benzene, ethyl acetate and carbon disulfide. -- Wikipedia. C4H7NO None None None 5901.54 4984.75 5123.87 5020.42 4890.78 5120.1 4850.2 5810.75 5347.7 4491.55 5752.19 5211.5 4746.31 5313.54 4966.25 5682.12 4530.3 5609.05 5556.05 5179.12 5838.24 4940.45 4503.45 5385.75 4534.43 5603.12 5076.36 4800.51 4975.3 4676.05 4693.6 4836.43 4971.86 4564.31 5569.79 6247.48 4612.05 5136.58 4495.94 5005.64 4957.22 5271.94 85.02952458_MZ Diacetyl Un 1.0 None None None None Diacetyl is a natural by-product of secondary or malolactic fermentation. It is a vicinal diketone (two C=O groups, side-by-side) with the molecular formula C4H6O2. Carrier of aroma of butter, vinegar, coffee, and other foods. Beer sometimes undergoes a diacetyl rest, which entails waiting two or three days after fermentation is complete, to allow the yeast to absorb the diacetyl it produced earlier in the fermentation cycle. The makers of some wines, such as chardonnay, deliberately promote the production of diacetyl because of the feel and flavors it imparts. C4H6O2, But-2-enoic acid, Oxolan-3-one None None None 55750.5 51655.5 59804.4 40905.2 55543.2 74517.3 57870.8 46546.4 57896.3 62694.0 55078.8 58932.9 65240.5 55048.8 63469.4 51900.3 41782.9 72726.8 63536.1 62554.6 55098.0 58944.0 58116.3 55294.8 57577.1 53867.3 56898.0 58238.3 61232.3 58217.0 43788.2 49560.7 60732.1 50243.7 59027.9 66111.7 52087.0 54457.5 38966.3 64120.7 51947.6 53403.2 85.06578237_MZ Iso-Valeraldehyde Un 1.0 None None None None iso-Valeraldehyde is an oxygenated (aldehyde) volatile organic compounds (VOC), normally found in humans, particularly in the gut. iso-Valeraldehyde is a leucine degradation product that has been found in elevated concentrations in some cases of hepatic encephalopathy, however not significantly. Fermentation of carbohydrates in the gut produces ethanoic, propionic, butanoic, pentanoic, and hexanoic acid acids, particularly by Bacteroides, although it is possible that some of the iso-Valeraldehyde is of dietetic origin. iso-Valeraldehyde has been found to be a normal component of the chemical profile of cheddar cheese, spirits (beer, rum, sake, wine). (PMID: 17314143, 18275147, 18175918, 16899660). C5H10O None None None 1395.93 1246.88 1230.11 1419.21 1321.65 1150.91 1163.76 1444.1 1272.79 1126.46 1232.89 1146.02 683.8 1189.95 1282.36 1120.87 1540.46 876.118 1113.58 896.323 1158.69 1217.62 1195.96 1263.9 1134.24 1125.98 1188.94 1070.01 1061.78 1267.55 973.222 879.234 1031.9 1249.37 1060.19 1216.44 1056.87 1320.95 1066.34 1233.71 909.756 1198.79 86.02489067_MZ 2-Aminoacrylic acid Un 1.0 None None None None Dehydroalanine (or (alpha)-(beta)-di-dehydroalanine) is an uncommon amino acid found in peptides of microbial origin (an unsaturated amino acid). C3H5NO2 None None None 8402.49 7362.5 6459.77 5823.41 6092.79 7514.26 7774.84 6423.37 5494.8 6791.87 6392.85 5900.0 11088.0 7243.39 5831.36 7962.78 6864.76 8249.48 6444.51 8321.45 8657.77 5092.87 6139.6 7162.69 6286.4 5406.91 6992.54 7435.89 6538.78 5734.11 8238.15 6921.42 5891.68 6957.99 5761.86 7270.22 5937.59 6419.07 7694.59 6229.69 7990.13 7435.75 87.00865528_MZ Pyruvic acid Un 1.0 None None None None Pyruvic acid is an intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed.) Biological Source: Intermediate in primary metabolism including fermentation processes. Present in muscle in redox equilibrium with Lactic acid. A common constituent, as a chiral cyclic acetal linked to saccharide residues, of bacterial polysaccharides. Isolated from cane sugar fermentation broth and peppermint. Constituent of Bauhinia purpurea, Cicer arietinum (chickpea), Delonix regia, Pisum sativum (pea) and Trigonella caerulea (sweet trefoil) Use/Importance: Reagent for regeneration of carbonyl compdounds from semicarbazones, phenylhydrazones and oximes. Flavoring ingredient (Dictionary of Organic Compounds). C3H4O3, Malonic semialdehyde None None None 188776.0 310287.0 235155.0 329974.0 286240.0 208973.0 249663.0 269664.0 192574.0 194260.0 204626.0 204586.0 317499.0 215966.0 281498.0 267819.0 286317.0 256541.0 274492.0 239621.0 244631.0 193310.0 237594.0 307194.0 297913.0 259382.0 355512.0 214038.0 268866.0 166052.0 301076.0 361978.0 240708.0 227752.0 221295.0 253388.0 201801.0 194073.0 226910.0 276652.0 272505.0 292995.0 87.04518183_MZ Butyric acid Un 1.0 None None None None Butyric acid, a four-carbon fatty acid, is formed in the human colon by bacterial fermentation of carbohydrates (including dietary fiber), and putatively suppresses colorectal cancer (CRC). Butyrate has diverse and apparently paradoxical effects on cellular proliferation, apoptosis and differentiation that may be either pro-neoplastic or anti-neoplastic, depending upon factors such as the level of exposure, availability of other metabolic substrate and the intracellular milieu. In humans, the relationship between luminal butyrate exposure and CRC has been examined only indirectly in case-control studies, by measuring fecal butyrate concentrations, although this may not accurately reflect effective butyrate exposure during carcinogenesis. Perhaps not surprisingly, results of these investigations have been mutually contradictory. The direct effect of butyrate on tumorigenesis has been assessed in a no. of in vivo animal models, which have also yielded conflicting results. In part, this may be explained by methodology: differences in the amount and route of butyrate administration, which are likely to significantly influence delivery of butyrate to the distal colon. (PMID: 16460475) Butyric acid is a carboxylic acid found in rancid butter, parmesan cheese, and vomit, and has an unpleasant odor and acrid taste, with a sweetish aftertaste (similar to ether). Butyric acid is a fatty acid occurring in the form of esters in animal fats and plant oils. Interestingly, low-molecular-weight esters of butyric acid, such as methyl butyrate, have mostly pleasant aromas or tastes. As a consequence, they find use as food and perfume additives. Butyrate is produced as end-product of a fermentation process solely performed by obligate anaerobic bacteria. C4H8O2, Isobutyric acid None None None 8107.52 8023.75 8428.07 8776.66 7627.05 7351.88 7815.5 8569.18 6373.28 7585.83 7051.79 6985.62 6193.7 10860.7 8154.16 7525.13 8775.52 7851.53 6834.02 6841.47 8449.46 5709.42 6471.62 7467.51 6669.12 6279.56 7669.58 6869.54 6533.06 7546.71 6853.75 6807.2 6719.77 6196.23 6638.68 7437.54 6684.76 5715.92 5995.35 7531.63 5327.38 7836.2 88.04051410_MZ L-Alanine Un 1.0 None None None None Alanine is a nonessential amino acid made in the body from the conversion of the carbohydrate pyruvate or the breakdown of DNA and the dipeptides carnosine and anserine. It is highly concentrated in muscle and is one of the most important amino acids released by muscle, functioning as a major energy source. Plasma alanine is often decreased when the BCAA (Branched Chain Amino Acids) are deficient. This finding may relate to muscle metabolism. Alanine is highly concentrated in meat products and other high-protein foods like wheat germ and cottage cheese. Alanine is an important participant as well as regulator in glucose metabolism. Alanine levels parallel blood sugar levels in both diabetes and hypoglycemia, and alanine reduces both severe hypoglycemia and the ketosis of diabetes. It is an important amino acid for lymphocyte reproduction and immunity. Alanine therapy has helped dissolve kidney stones in experimental animals. Normal alanine metabolism, like that of other amino acids, is highly dependent upon enzymes that contain vitamin B6. Alanine, like GABA, taurine and glycine, is an inhibitory neurotransmitter in the brain. http://www.dcnutrition.com/AminoAcids/). C3H7NO2, Beta-Alanine, Sarcosine None None None 383875.0 513464.0 373871.0 118114.0 449907.0 455914.0 297345.0 455261.0 287525.0 272636.0 395689.0 350705.0 313188.0 385288.0 462607.0 495646.0 376666.0 336957.0 318195.0 461754.0 391174.0 444884.0 413394.0 415504.0 347235.0 412364.0 295759.0 347641.0 475879.0 540143.0 439394.0 349192.0 268503.0 299504.0 379302.0 266338.0 279268.0 464697.0 232424.0 423138.0 243556.0 288664.0 88.98799573_MZ Oxalic acid Un 1.0 None None None None Oxalic acid is a strong dicarboxylic acid occurring in many plants and vegetables. It is produced in the body by metabolism of glyoxylic acid or ascorbic acid. It is not metabolized but excreted in the urine. It is used as an analytical reagent and general reducing agent. -- Pubchem; Oxalic acid (IUPAC name: ethanedioic acid, formula H2C2O4) is a dicarboxylic acid with structure (HOOC)-(COOH). Because of the joining of two carboxyl groups, this is one of the strongest organic acids. It is also a reducing agent. The anions of oxalic acid as well as its salts and esters are known as oxalates. -- Wikipedia; Bodily oxalic acid may also be synthesized via the metabolism of either glyoxylic acid or unused ascorbic acid (vitamin C), which is a serious health consideration for long term megadosers of vitamin C supplements. 80% of kidney stones are formed from calcium oxalate. Some Aspergillus species produce oxalic acid, which reacts with blood or tissue calcium to precipitate calcium oxalate. There is some preliminary evidence that the administration of probiotics can affect oxalic acid excretion rates (and presumably oxalic acid levels as well.) -- Wikipedia. C2H2O4 None None None 2761.9 2668.96 2842.96 2921.48 2713.23 2637.14 2886.49 3736.35 3357.23 2973.85 2977.57 2874.19 2223.79 3020.87 2843.55 1788.35 3352.48 1782.78 2502.56 2229.16 3007.07 3487.67 2777.58 3098.02 3084.08 3674.89 2412.3 2488.66 2587.67 3528.15 2394.72 1427.89 2631.7 2482.91 3542.7 3230.34 3109.16 3122.09 3198.05 3433.14 2343.11 2321.89 89.02459351_MZ L-Lactic acid Un 1.0 None None None None Lactic acid plays a role in several biochemical processes and is produced in the muscles during intense activity. Lactate measurement in the critically ill has been traditionally used to stratify patients with poor outcome. However, plasma lactate levels are the result of a finely tuned interplay of factors that affect the balance between its production and its clearance. When the oxygen supply does not match its consumption, organisms such as man who are forced to produce ATP for their integrity adapt in many different ways up to the point when energy failure occurs. Lactate, being part of the adaptive response, may then be used to assess the severity of the supply/demand imbalance. In such a scenario, the time to intervention becomes relevant: early and effective treatment may allow the cell to revert to a normal state, as long as the oxygen machinery (i.e. mitochondria) is intact. Conversely, once the mitochondria are deranged, energy failure occurs even in the presence of normoxia. The lactate increase in critically ill patients may therefore be viewed as an early marker of a potentially reversible state. (PMID 16356243) A number of studies have demonstrated that malignant transformation is associated with an increase in glycolytic flux and in anaerobic and aerobic cellular lactate excretion. Using quantitative bioluminescence imaging in various primary carcinomas in patients (uterine cervix, head and neck, colorectal region) at first diagnosis of the disease, lactate concentrations in tumors in vivo could be relatively low or extremely high (up to 40 micromol/g) in different individual tumors or within the same lesion. In all tumor entities investigated, high molar concentrations of lactate were correlated with a high incidence of distant metastasis already in an early stage of the disease. Low lactate tumors (< median of approximately 8 micromol/g) were associated with both a longer overall and disease free survival compared to high lactate lesions (lactate > approximately 8 micromol/g). Lactate dehydrogenase was found to be upregulated in most of these tumors compared to surrounding normal tissue. (PMID 15279558). C3H6O3, Hydroxypropionic acid, Glyceraldehyde, Dihydroxyacetone None None None 1872030.0 1873920.0 1555630.0 685724.0 1507190.0 2908960.0 1519430.0 1781610.0 1732300.0 1737230.0 1594840.0 2008420.0 1436670.0 1774270.0 1476510.0 2672320.0 988620.0 2621750.0 1817940.0 2330990.0 1580690.0 2112740.0 1879180.0 1854000.0 1443870.0 2154750.0 1496380.0 2110280.0 1726950.0 2297190.0 2048650.0 1903220.0 1871550.0 1777580.0 1386840.0 2090720.0 1547550.0 1542840.0 792430.0 1827130.0 1471380.0 1657770.0 92.05059939_MZ Aniline Un 1.0 None None None None Aniline is an organic chemical compound, specifically a primary aromatic amine. It consists of a benzene ring attached to an amino group. Aniline is oily and, although colorless, it can be slowly oxidized and resinified in air to form impurities which can give it a red-brown tint. Its boiling point is 184 degree centigrade and its melting point is -6 degree centegrade. It is a liquid at room temperature. Like most volatile amines, it possesses a somewhat unpleasant odour of rotten fish, and also has a burning aromatic taste; it is a highly acrid poison. It ignites readily, burning with a large smoky flame. Aniline reacts with strong acids to form salts containing the anilinium (or phenylammonium) ion (C6H5-NH3+), and reacts with acyl halides (such as acetyl chloride (ethanoyl chloride), CH3COCl) to form amides. The amides formed from aniline are sometimes called anilides, for example CH3-CO-NH-C6H5 is acetanilide, for which the modern name is N-phenyl ethanamide. Like phenols, aniline derivatives are highly reactive in electrophilic substitution reactions. For example, sulfonation of aniline produces sulfanilic acid, which can be converted to sulfanilamide. Sulfanilamide is one of the sulfa drugs which were widely used as antibacterial in the early 20th century. Aniline was first isolated from the destructive distillation of indigo in 1826 by Otto Unverdorben. In 1834, Friedrich Runge isolated from coal tar a substance which produced a beautiful blue color on treatment with chloride of lime; this he named kyanol or cyanol. In 1841, C. J. Fritzsche showed that by treating indigo with caustic potash it yielded an oil, which he named aniline, from the specific name of one of the indigo-yielding plants, Indigofera anil, anil being derived from the Sanskrit, dark-blue. C6H7N None None None 4329.32 4584.4 4032.59 4296.52 4051.27 4169.75 4609.37 4518.54 3984.85 4409.38 4398.95 4318.95 3904.55 4433.45 4431.03 4159.5 5299.87 4568.99 4101.95 4434.16 4265.7 4205.41 4106.28 4693.13 4107.19 3818.74 3965.98 4076.02 4268.19 4626.14 4096.57 3855.5 3464.26 4421.26 4054.17 4284.92 4148.65 3561.62 3945.0 4376.47 4587.74 4135.9 92.98445263_MZ Dimethyldisulfide Un 1.0 None None None None Dimethyldisulfide is a volatile organic compound. Methyl disulfide is occasionally found as a volatile component of normal human breath and biofluids. Dimethyldisulfide is one of the representative volatile components found in oral malodor. Dimethyldisulfide concentrations in breath is a practical noninvasive way to assess recent exposure to sulfur compounds in sulfate pulp mills, and therefore it should be applicable to workplaces contaminated. (PMID: 5556886, 14691119, 11236158, 8481097). C2H6S2 None None None 2029.58 8567.48 2222.28 1314.54 1060.94 4009.13 1181.39 1815.33 1432.28 1566.2 2454.97 3066.71 1426.68 1910.84 1017.4 3894.62 4054.39 1669.7 1759.72 1354.55 4138.17 2587.75 2231.66 2324.9 2645.77 1237.78 2918.76 2394.04 2021.81 3778.87 3826.71 4975.06 1548.06 3453.46 3235.6 1473.77 3490.98 2342.08 2831.48 1335.17 608.826 1381.64 93.03490045_MZ Phenol Un 1.0 None None None None Phenol, is a toxic, colourless crystalline solid with a sweet tarry odor that resembles a hospital smell. It is commonly used as an antiseptic and disinfectant. It is active against a wide range of micro-organisms including some fungi and viruses, but is only slowly effective against spores. It has been used to disinfect skin and to relieve itching. Phenol is also used in the preparation of cosmetics including sunscreens, hair dyes, and skin lightening preparations. It is also used in the production of drugs (it is the starting material in the industrial production of aspirin), weedkillers, and synthetic resins. Phenol can be found in areas with high levels of motor traffic, therefore, people living in crowded urban areas are frequently exposed to traffic-derived phenol vapor. The average (mean +/- SD) phenol concentration in urine among normal individuals living in urban areas is 7.4 +/- 2.2 mg/g of creatinine. Exposure of the skin to concentrated phenol solutions causes chemical burns which may be severe; in laboratories where it is used, it is usually recommended that polyethylene glycol solution is kept available for washing off splashes. Notwithstanding the effects of concentrated solutions, it is also used in cosmetic surgery as an exfoliant, to remove layers of dead skin (Wikipedia). In some bacteria phenol can be directly synthesized from tyrosine via the enzyme tyrosine phenol-lyase [EC:4.1.99.2]. C6H6O None None None 41638.3 42322.2 41333.9 42454.4 45584.5 45657.2 50116.2 50122.9 42610.2 44009.1 47007.5 43757.3 39150.9 44171.4 47610.4 40584.0 58179.0 46079.6 40902.4 47485.3 42119.6 44891.7 45249.9 48365.9 41850.1 36961.6 44219.8 43754.3 43677.8 51861.5 39182.6 38158.7 34449.3 41278.0 38623.3 49540.8 33729.0 34656.3 36260.8 46681.2 42955.4 40568.5 96.96953796_MZ Phosphoric acid Un 1.0 None None None None Phosphoric acid, also known as orthophosphoric acid or phosphoric(V) acid, is a mineral acid with the chemical formula H3PO4. Alternatively, orthophosphoric acid molecules can combine with themselves to form a variety of compounds referred to as phosphoric acids in a more general way. For a discussion of these, see Phosphoric acids and Phosphates. Appears to exist only as a food additive and produced synthetically. --Wikipedia. H3O4P None None None 532331.0 576776.0 614967.0 693890.0 716288.0 667910.0 695412.0 643107.0 665913.0 599491.0 560635.0 622056.0 610678.0 570931.0 746836.0 574054.0 682956.0 653427.0 731538.0 699023.0 609473.0 578242.0 658899.0 551939.0 681733.0 528020.0 738149.0 613636.0 603229.0 661873.0 594772.0 613138.0 470139.0 551048.0 672776.0 639436.0 608478.0 613217.0 468925.0 627251.0 610553.0 592947.0 97.06560871_MZ Cyclohexanone Un 1.0 None None None None Cyclohexanone is a colorless oily liquid with an odor resembling acetone and peppermint. Cyclohexanone is occasionally found as a volatile component of human urine. Biological fluids such as blood and urine have been shown to contain a large number of components, some of them volatiles (low boiling point) apparently present in all individuals, while others such are much more variable. In some cases differences up to an order of magnitude are observed. Although some of these changes may have dietary origins, others seem to be characteristic of the individual. Cyclohexanone is obtained through oxidation of cyclohexane or dehydrogenation of phenol. Approx. 95% of its manufacturing is used for the production of nylon. Information on toxicity to human beings is fragmentary. Acute exposure is characterized by irritation of the eyes, nose, and throat. In two persons, drowsiness and renal impairment were found; however, these workers were also exposed to other compounds. Hepatic disorders were found in a group of workers exposed for over five years. In animals, cyclohexanone is characterized by relatively low acute toxicity (DL50 by intragastric administration is approximately 2 g/kg body wt.). Effects on the central nervous system (CNS) were found (narcosis), as well as irritation of the eyes and skin. Following multiple administration, effects were found in the CNS, liver, and kidneys as well as irritation of the conjunctiva. Mutagenic and genotoxic effects were found, but no teratogenic effects were detected; however, there were embryotoxic effects and influence on reproduction Cyclohexanone is well absorbed through the skin, respiratory tract, and alimentary tract. The main metabolic pathway leads to cyclohexanol, which is excreted in urine coupled with glucuronic acid. A high correlation was found between the concentration of cyclohexanone in the working environment and its concentration in urine. Cyclohexanone is formed from the hydrocarbons cyclohexane and 1-, 2-, and 3-hexanol. A patient's case report documents the development of anosmia (an olfactory disorder) and rhinitis caused by occupational exposure to organic solvents, including cyclohexanone (PMID: 10476412, 16925936, 16477465). C6H10O None None None 11898.3 12033.6 15718.2 11796.9 15807.2 13032.4 16375.4 19390.5 10226.9 11024.3 12124.9 9827.31 12627.4 13564.9 15933.4 12388.1 26849.9 12488.6 12719.3 15653.4 12484.2 10231.1 14366.9 15740.2 12310.8 9878.32 13961.0 11522.0 9790.35 13312.0 11339.2 10620.1 9753.67 12058.7 9092.33 11399.4 9828.17 9843.82 11278.3 12214.2 9507.13 12282.8 98.00694510_MZ Allyl isothiocyanate Un 1.0 None None None None Allyl isothiocyanate is a volatile organic compound. Allyl isothiocyanate (AITC) is a constituent of mustard, horseradish and wasabi and certain vegetables found in the human diet, mostly in cruciferous vegetables. AITC is a colorless to pale yellow liquid that is slightly soluble in water, but well soluble in most organic solvents. AITC possesses numerous biochemical and physiological activities. It is cytotoxic and tumorigenic at high doses and also is a modulator of enzymes involved in metabolism of xenobiotics, including carcinogens. It is plausible that the wide consumption of dietary AITC may have profound effects on human health. oxidative DNA damage may play important roles in carcinogenic processes induced by AITC. Allergic contact dermatitis from AICT is well known but infrequently reported. AITC is occasionally found as a volatile component of normal human biofluids. (PMID: 5556886, 8222057, 8000299, 10754276, 15373848). C4H5NS None None None 78788.7 57882.7 65880.8 78941.5 50115.2 63310.9 48485.8 45542.2 38724.0 56759.9 64699.4 53118.7 60901.9 76074.0 33776.7 78060.4 76634.9 47959.4 63330.8 42968.0 28954.1 39188.9 64326.0 61441.2 58715.1 51406.9 72178.8 71023.4 41918.1 54028.0 68045.7 38415.7 49086.2 44226.1 55192.9 66056.0 31592.9 54149.9 6420.69 56876.4 91476.2 47299.3 99.08230253_MZ 4-Methylpentanal Un 1.0 None None None None 4-Methylpentanal is an intermediate in the metabolism of C21-Steroid hormone. It is a substrate for Cytochrome P450 11A1 (mitochondrial). C6H12O, Hexanal, 3-Hexanone, Methyl isobutyl ketone, 2-Oxohexane, Ethyl isopropyl ketone None None None 5840.55 7838.03 7885.0 7176.13 10220.5 9254.55 7113.35 6259.71 7479.64 7803.53 9286.9 9375.34 4384.04 8462.94 9287.53 6759.26 5607.64 5662.02 6124.92 5478.04 6776.94 7940.04 7982.82 7561.67 6779.31 8007.75 9095.06 7234.55 7810.53 7629.92 5483.48 6204.55 9904.96 6655.45 8128.77 6492.62 6776.67 9733.67 6014.21 7820.59 5209.65 5558.14 100.0767784_MZ 5-Aminopentanal Un 1.0 None None None None The aminoaldehydes 5-aminopentanal, derived from the oxidation of the diamines putrescine and cadaverine,is produced utilizing a copper amine oxidase (CAO) from Euphorbia characias latex and tested with in vitro cultivation of Leishmania infantum promastigotes.Whereas the aminoaldehydes derived from the oxidation of the diamines were stimulating factors for growth of Leishmania infantum promastigotes, the aldehydes derived from polyamines oxidation had a drastic inhibitory effect on the vitality and growth of these parasites. Thus, a double scenario arises, showing the use of aldehydes from diamines to obtain a large number of organisms of Leishmania infantum promastigotes to use in serological studies, whereas the aldehydes derived from polyamines could be used as a new strategy for therapeutic treatment against these parasites. C5H11NO None None None 5656.71 4727.06 5110.97 6692.79 7367.83 4345.39 5580.77 4005.08 6294.56 5233.25 5000.33 4407.97 4766.18 5870.46 6079.0 5715.28 8134.61 6852.93 3992.54 3430.59 4828.84 3574.96 5651.54 3952.45 6216.57 2763.25 4456.8 5414.69 6277.52 4539.35 5257.6 6578.08 3626.38 3108.23 5446.0 4586.86 3862.15 5311.47 3060.04 4657.33 5240.29 3838.22 101.0245480_MZ Acetoacetic acid Un 1.0 None None None None Acetoacetic acid is a weak organic acid and can be produced in the human liver under certain conditions of poor metabolism leading to excessive fatty acid breakdown (diabetes mellitus leading to diabetic ketoacidosis), it is then partially converted to acetone by decarboxylation and excreted either in urine or through respiration. Persistent mild hyperketonemia is a common finding in newborns. These compounds serve as an indispensable source of energy for extrahepatic tissues, especially the brain and lung of developing rats. Another important function of ketone bodies is to provide acetoacetyl-CoA and acetyl-CoA for synthesis of cholesterol, fatty acids, and complex lipids. During the early postnatal period, acetoacetate (AcAc) and beta-hydroxybutyrate are preferred over glucose as substrates for synthesis of phospholipids and sphingolipids in accord with requirements for brain growth and myelination. Thus, during the first 2 wk of postnatal development, when the accumulation of cholesterol and phospholipids accelerates, the proportion of ketone bodies incorporated into these lipids increases. On the other hand, an increased proportion of ketone bodies are utilized for cerebroside synthesis during the period of active myelination. In the lung, AcAc serves better than glucose as a precursor for the synthesis of lung phospholipids. The synthesized lipids, particularly dipalmityl phosphatidylcholine, are incorporated into surfactant, and thus have a potential role in supplying adequate surfactant lipids to maintain lung function during the early days of life. (PMID 3884391) The acid is also present in the metabolism of those undergoing starvation or prolonged physical exertion as part of gluconeogenesis. When ketone bodies are measured by way of urine concentration, acetoacetic acid, along with beta-hydroxybutyric acid or acetone, is what is detected. C4H6O3, 2-Ketobutyric acid, Acetoacetic acid, 2-Methyl-3-oxopropanoic acid, Succinic acid semialdehyde, (S)-Methylmalonic acid semialdehyde, 4-Hydroxycrotonic acid None None None 108013.0 106012.0 116849.0 103071.0 107722.0 135069.0 109001.0 95183.6 116749.0 121063.0 113413.0 116262.0 115260.0 112565.0 123367.0 104506.0 97816.6 115624.0 120485.0 115803.0 111165.0 120780.0 115855.0 112015.0 106098.0 104889.0 113005.0 114927.0 122194.0 125260.0 93046.7 99546.1 111630.0 102432.0 129690.0 128941.0 105297.0 110351.0 97411.2 126333.0 101826.0 105624.0 101.0608791_MZ Valeric acid Un 1.0 None None None None C5H10O2, Isovaleric acid None None None 14618.6 15925.8 13614.8 15577.4 12658.1 13764.6 13015.4 16565.2 11129.8 14415.4 12808.9 12462.2 10973.3 14864.4 13501.2 11932.4 15310.9 15441.3 11238.7 11409.7 13827.2 11607.3 12921.0 15436.8 11098.8 10957.6 12771.3 13272.9 10954.4 15060.9 12015.4 11200.9 11042.6 13326.0 12497.2 13785.3 10779.3 11057.0 11459.6 14563.4 9903.93 12492.5 102.0196529_MZ 3-Oxoalanine Un 1.0 None None None None Human lysosomal arylsulfate A (ASA) is a member of the sulfatase family which requires the posttranslational oxidation of thiol group of a cysteine that is conserved among all eukaryotic sulfatases, yielding 2-formylglycine. (PMID: 9521684). C3H5NO3, Pyruvatoxime None None None 1527.56 1775.35 1213.94 1680.71 2309.06 1712.15 1488.44 1404.8 1321.74 1654.21 1468.28 1171.43 1212.26 1578.45 1750.31 1632.7 1175.91 1220.09 1568.9 1361.59 1179.32 1189.64 1523.84 1627.48 1298.92 1259.48 1756.73 1191.72 1205.96 1513.07 1393.27 2132.42 1432.78 1283.29 1235.39 1616.16 1278.15 1318.36 1525.02 1894.99 1391.15 1467.54 102.0468342_MZ 5-Aminoimidazole Un 1.0 None None None None Because of its ability to mimic a low energy status of the cell, the cell-permeable nucleoside 5-aminoimidazole-4-carboxamide (AICA) riboside was proposed as an antineoplastic agent switching off major energy-consuming processes associated with the malignant phenotype (lipid production, DNA synthesis, cell proliferation, cell migration, etc.). Key to the antineoplastic action of AICA riboside is its conversion to ZMP, an AMP mimetic that at high concentrations activates the AMP-activated protein kinase (AMPK). (PMID: 16985054). C3H5N3 None None None 385.505 358.026 448.724 364.045 373.931 447.304 401.626 314.829 354.125 468.795 413.555 444.143 444.688 378.954 423.805 361.857 484.102 368.251 343.781 304.881 379.406 408.379 440.084 405.572 354.23 325.549 372.508 413.818 472.968 406.728 371.839 468.06 347.014 299.021 463.093 454.06 367.436 413.767 401.892 485.448 325.012 367.031 102.0559894_MZ Dimethylglycine Un 1.0 None None None None Dimethylglycine (DMG) is an amino acid derivative found in the cells of all plants and animals and can be obtained in the diet in small amounts from grains and meat. The human body produces DMG when metabolizing choline into Glycine. Dimethylglycine that is not metabolized in the liver is transported by the circulatory system to body tissue. Dimethylglycine was popular with Russian athletes and cosmonauts owing to its reputed ability to increase endurance and reduce fatigue. DMG is also a byproduct of homocysteine metabolism. Homocysteine and betaine are converted to methionine and N, N-dimethylglycine by betaine-homocysteine methyltransferase. C4H9NO2, Gamma-Aminobutyric acid, L-Alpha-aminobutyric acid, 2-Aminoisobutyric acid, (S)-b-aminoisobutyric acid, (R)-b-aminoisobutyric acid, 3-Aminoisobutanoic acid None None None 222759.0 192638.0 228840.0 184739.0 210326.0 130718.0 169722.0 303868.0 185087.0 167880.0 191876.0 158723.0 189698.0 241463.0 231839.0 128090.0 213200.0 198146.0 147147.0 161199.0 207899.0 181994.0 189430.0 174718.0 243937.0 173946.0 166287.0 205034.0 251264.0 170424.0 182146.0 159871.0 187879.0 140874.0 237573.0 149302.0 199669.0 208866.0 200202.0 216035.0 240641.0 178408.0 104.0353471_MZ L-Serine Un 1.0 None None None None Serine is a nonessential amino acid derived from glycine. Like all the amino acid building blocks of protein and peptides, serine can become essential under certain conditions, and is thus important in maintaining health and preventing disease. Low-average concentration of serine compared to other amino acids is found in muscle. Serine is highly concentrated in all cell membranes. (http://www.dcnutrition.com/AminoAcids/) L-Serine may be derived from four possible sources: dietary intake; biosynthesis from the glycolytic intermediate 3-phosphoglycerate; from glycine ; and by protein and phospholipid degradation. Little data is available on the relative contributions of each of these four sources of l-serine to serine homoeostasis. It is very likely that the predominant source of l-serine will be very different in different tissues and during different stages of human development. In the biosynthetic pathway, the glycolytic intermediate 3-phosphoglycerate is converted into phosphohydroxypyruvate, in a reaction catalyzed by 3-phosphoglycerate dehydrogenase (3- PGDH; EC 1.1.1.95). Phosphohydroxypyruvate is metabolized to phosphoserine by phosphohydroxypyruvate aminotransferase (EC 2.6.1.52) and, finally, phosphoserine is converted into l-serine by phosphoserine phosphatase (PSP; EC 3.1.3.3). In liver tissue, the serine biosynthetic pathway is regulated in response to dietary and hormonal changes. Of the three synthetic enzymes, the properties of 3-PGDH and PSP are the best documented. Hormonal factors such as glucagon and corticosteroids also influence 3-PGDH and PSP activities in interactions dependent upon the diet. L-serine plays a central role in cellular proliferation. L-Serine is the predominant source of one-carbon groups for the de novo synthesis of purine nucleotides and deoxythymidine monophosphate. It has long been recognized that, in cell cultures, L-serine is a conditional essential amino acid, because it cannot be synthesized in sufficient quantities to meet the cellular demands for its utilization. In recent years, L-serine and the products of its metabolism have been recognized not only to be essential for cell proliferation, but also to be necessary for specific functions in the central nervous system. The findings of altered levels of serine and glycine in patients with psychiatric disorders and the severe neurological abnormalities in patients with defects of L-serine synthesis underscore the importance of L-serine in brain development and function. (PMID 12534373). C3H7NO3 None None None 43358.5 41924.1 43830.8 31665.8 45014.1 44734.4 43813.0 54515.9 49842.2 34401.5 52829.3 47195.5 39290.6 38216.3 45443.3 55361.6 42368.3 30976.9 36377.7 48296.7 37283.1 38934.0 48890.7 51574.6 37519.4 33598.1 43737.0 49408.3 65768.3 45798.3 42271.2 52156.5 32655.0 32640.6 59775.6 38707.2 41758.0 56804.3 41763.3 47110.2 31228.1 36727.8 105.0201586_MZ L-Glyceric acid Un 1.0 None None None None L-glyceric acid is a human urinary metabolite present in patients with L-Glyceric aciduria. The formation of L-glyceric acid from accumulated hydroxypyruvate is due to deficiency of human glyoxylate reductase/hydroxypyruvate reductase (GRHPR, EC 1.1.1.81), a D-2-hydroxy-acid dehydrogenase that plays a critical role in the removal of the metabolic by-product glyoxylate from within the liver. Deficiency of this enzyme is the underlying cause of primary hyperoxaluria type 2 (PH2) and leads to increased urinary oxalate levels, formation of kidney stones and renal failure. (PMID: 16756993). C3H6O4, Glyceric acid None None None 9733.99 10983.8 6998.42 7354.5 6547.45 8710.33 6483.49 7527.87 18241.4 12274.1 8720.26 10537.6 4095.01 14817.4 11342.2 7331.66 6681.94 5325.47 5604.58 6302.38 8059.31 10706.4 6571.4 6858.96 6231.6 9253.89 6861.86 8173.31 6593.71 10228.5 8423.86 7339.73 6897.1 8648.61 12435.5 8076.27 8759.04 8470.33 4886.29 7095.32 4997.08 6739.58 105.0332333_MZ Benzaldehyde Un 1.0 None None None None Benzaldehyde is occasionally found as a volatile component of urine. Benzaldehyde is an aromatic aldehyde used in cosmetics as a denaturant, a flavoring agent, and as a fragrance. Currently used in only seven cosmetic products, its highest reported concentration of use was 0.5% in perfumes. Benzaldehyde is a generally regarded as safe (GRAS) food additive in the United States and is accepted as a flavoring substance in the European Union. Because Benzaldehyde rapidly metabolizes to Benzoic Acid in the skin, the available dermal irritation and sensitization data demonstrating no adverse reactions to Benzoic Acid were considered supportive of the safety of Benzaldehyde. Benzaldehyde is absorbed through skin and by the lungs, distributes to all well-perfused organs, but does not accumulate in any specific tissue type. After being metabolized to benzoic acid, conjugates are formed with glycine or glucuronic acid, and excreted in the urine. Several studies have suggested that Benzaldehyde can have carcinostatic or antitumor properties. Overall, at the concentrations used in cosmetics, Benzaldehyde was not considered a carcinogenic risk to humans. Although there are limited irritation and sensitization data available for Benzaldehyde, the available dermal irritation and sensitization data and ultraviolet (UV) absorption and phototoxicity data demonstrating no adverse reactions to Benzoic Acid support the safety of Benzaldehyde as currently used in cosmetic products. (PMID: 16835129, Int J Toxicol. 2006;25 Suppl 1:11-27.). C7H6O None None None 1903.57 1901.56 1562.34 1547.86 1900.8 2158.9 1807.69 1802.87 2619.94 2237.15 1975.84 1900.07 1245.29 2377.46 2308.07 1865.34 1538.87 1587.91 1558.87 1660.99 1592.43 1784.13 1682.52 1955.58 1336.72 1504.94 1763.02 1855.61 1720.42 1933.88 1762.62 1690.23 1454.97 1615.23 1906.61 1648.24 1493.55 1680.37 1199.27 1701.34 1469.15 1631.62 106.0662054_MZ 4-Aminobutyraldehyde Un 1.0 None None None None 4-Aminobutyraldehyde is a metabolite of putrescine. It is a substrate of human liver aldehyde dehydrogenase (EC 1.2.1.3) cytoplasmic (E1) and mitochondrial (E2) isozymes (PMID 3324802). C4H9NO None None None 1108.84 1072.35 1106.19 1118.01 1247.9 1156.65 1413.65 1070.66 1077.09 1147.14 1098.8 1295.17 993.073 955.446 1026.17 1101.97 1365.46 1119.94 999.605 1306.39 999.144 981.718 1034.49 965.788 969.884 919.489 1142.99 1215.92 1004.93 1102.66 1124.54 1025.17 1177.93 1066.52 957.579 848.138 790.593 1060.04 670.93 1004.91 1129.59 943.909 107.0128098_MZ Quinone Un 1.0 None None None None Quinone is also called 1,4-benzoquinone or cyclohexadienedione. Quinones are oxidized derivatives of aromatic compounds and are often readily made from reactive aromatic compounds with electron-donating substituents such as phenols and catechols, which increase the nucleophilicity of the ring and contributes to the large redox potential needed to break aromaticity. Derivatives of quinones are common constituents of biologically relevant molecules. Some serve as electron acceptors in electron transport chains such as those in photosynthesis (plastoquinone, phylloquinone), and aerobic respiration (ubiquinone). Quinone is a common constituent of biologically relevant molecules (e.g. Vitamin K1 is phylloquinone). A natural example of quinones as oxidizing agents is the spray of bombardier beetles. Hydroquinone is reacted with hydrogen peroxide to produce a fiery blast of steam, a strong deterent in the animal world. C6H4O2, 1,2-Benzoquinone None None None 1437.06 1375.76 1724.23 1424.83 1777.28 1778.42 1446.94 1118.17 1799.75 1790.66 1878.96 1847.62 1182.82 1678.2 1631.59 1320.29 1116.24 1429.56 1622.46 1359.95 1582.3 1911.48 1645.95 1360.38 1395.69 1837.26 1526.59 1722.76 1882.5 1623.7 1178.14 1370.82 1924.78 1229.63 1832.8 1600.97 1381.45 1921.67 1137.4 1682.33 1073.85 1420.88 107.0501507_MZ p-Cresol Un 1.0 None None None None p-Cresol (4-methylphenol), a 108.1 Da volatile low-molecular-weight compound, is a phenol. It is a partially lipophilic moiety which strongly binds to plasma protein (close to 100%) under normal conditions. p-Cresol is metabolized through conjugation, mainly sulphation and glucuronization, but removal of the unconjugated p-cresol is, at least in part, via the urine. Therefore it is not surprising that this compound, together with several other phenoles, is retained when the kidneys fail. P-Cresol is an end-product of protein breakdown, and an increase of the nutritional protein load in healthy individuals results in enhanced generation and urinary excretion. The serum p-cresol concentration in uremic patients can be decreased by changing to a low-protein diet. p-Cresol is one of the metabolites of the amino acid tyrosine, and to a certain extent also of phenylalanine, which are converted to 4-hydroxyphenylacetic acid by intestinal bacteria, before being decarboxylated to p-cresol (putrefaction). The main contributing bacteria are aerobes (mainly enterobacteria), but to a certain extent also anaerobes play a role (mainly Clostridium perfringens). In uremia, modifications in the intestinal flora result in the specific overgrowth of bacteria that are specific p-cresol producers. The administration of antibiotics reduces urinary excretion of p-cresol, as a result of the liquidation of the producing bacteria. Environmental factors might also contribute. The liver cytochrome P450 metabolizes toluene to benzyl alcohol, but also to o-cresol and p-cresol. Toluene is not only used industrially, but it is also the most widely abusively inhaled solvent. Furthermore, p-cresol is a metabolite of menthofuran, one of the metabolites of R-(+)-pulegone, which is found in extracts from the plants Mentha pulegium and Hedeoma pulegioides, commonly known as pennyroyal oil and pennyroyal tea. These extracts are popular as unconventional herbal therapeutic agents and are applied as abortiva, diaphoretics, emmenagogues, and psychedelic drugs. Pennyroyal oil is extensively used for its pleasant mint-like smell in the flavoring industry. The toxicity of pennyroyal oil and menthofuran is well known. Another compound used in traditional medicine, especially in Japan, which is a precursor of p-cresol is wood tar creosote. p-Cresol has been reported to affect several biochemical, biological and physiological functions: (i) it diminishes the oxygen uptake of rat cerebral cortex slices; (ii) it increases the free active drug concentration of warfarin and diazepam; (iii) it has been related to growth retardation in the weanling pig; (iv) it alters cell membrane permeability, at least in bacteria; (v) it induces LDH leakage from rat liver slices; (vi) it induces susceptibility to auditive epileptic crises; and (vii) it blocks cell K+ channels. (PMID: 10570076). p-Cresol is a uremic toxin that is at least partially removed by peritoneal dialysis in haemodialysis patients, and has been involved in the progression of renal failure. (MID: 11169029). At concentrations encountered during uremia, p-cresol inhibits phagocyte function and decreases leukocyte adhesion to cytokine-stimulated endothelial cells. (PMID: 14681860). C7H8O, m-Cresol, o-Cresol, Benzyl alcohol None None None 17304.2 18979.5 20202.7 19093.2 22618.4 20781.2 18305.3 20950.7 17371.3 17955.2 19017.4 21432.5 14628.8 19229.6 22877.7 20230.5 21532.3 16641.9 15434.2 16767.4 15292.8 17052.8 18548.1 17089.9 15768.9 16170.1 19698.5 17707.6 19899.1 19643.7 20367.4 15252.4 17430.3 15116.8 18930.6 15994.7 15446.6 16364.6 15912.0 19678.3 13476.7 14940.8 108.0123814_MZ Hypotaurine Un 1.0 None None None None Hypotaurine is a product of enzyme cysteamine dioxygenase [EC 1.13.11.19] in taurine and hypotaurine metabolism pathway (KEGG). It may function as an antioxidant and a protective agent under physiological conditions (PMID 14992269). C2H7NO2S None None None 19496.0 9417.18 7797.31 3960.46 3235.86 10702.7 4790.33 9019.36 3924.1 5155.17 7472.43 8265.67 6753.84 4610.12 3053.73 9252.36 3403.34 8849.22 1958.14 4511.71 7714.01 5618.96 7932.53 6833.61 11097.5 2136.92 3391.64 4994.36 7962.57 12282.3 15577.3 9074.79 3268.59 3430.86 5537.98 4908.92 3475.34 8065.75 4116.72 4031.22 5416.97 2694.07 108.0454972_MZ 4-Aminophenol Un 1.0 None None None None 4-aminophenol is considered a minor nephrotoxic metabolite of phenacetin and acetaminophen (paracetamol) in man. 4-Aminophenol can undergo autoxidations and metal-catalyzed and enzymatic oxidations in man to produce reactive oxygen species. (PMID 1713494). C6H7NO None None None 14540.7 13754.3 14530.8 13771.0 13269.5 14878.7 14072.3 14143.3 14170.2 13744.5 13597.0 14713.9 15291.1 14502.5 14069.7 13936.4 14146.9 15203.7 14022.5 14091.4 14740.7 13984.1 13667.6 13774.0 13709.9 13656.0 13925.2 13681.8 13657.1 15404.4 13627.0 12670.9 13303.6 13618.6 14604.6 13852.3 14260.4 14092.6 13863.7 13483.9 12974.2 13272.3 109.0294949_MZ Pyrocatechol Un 1.0 None None None None Pyrocatechol, often known as catechol or benzene-1,2-diol, is a benzenediol, with formula C6H4(OH)2. It was first prepared in 1839 by H. Reinsch by distilling catechin (the juice of Mimosa catechu). This colourless compound occurs naturally, but about 20000 tons are manufactured each year, mainly as precursors to pesticides, flavors, and fragrances. Its sulfonic acid is often present in the urine of many mammals. Small amounts of catechol occur naturally in fruits and vegetables, along with the enzyme polyphenol oxidase. Upon mixing the enzyme with the substrate and exposure to oxygen (as when a potato or apple is cut), the colorless catechol oxidizes to reddish-brown benzoquinone derivatives. The enzyme is inactivated by adding an acid, such as lemon juice, or by refrigeration. Excluding oxygen also prevents the browning reaction. Catechol melts at 28 oC and boils at 250 oC. It is employed in medicine as an expectorant. The dimethyl ether or veratrol is also used in medicine. Many other pyrocatechin derivatives have been suggested for therapeutic application. C6H6O2, Hydroquinone None None None 20907.4 20748.5 22475.7 21403.4 25816.5 23326.3 19088.3 19655.1 21165.2 22907.6 25418.1 26440.2 17070.8 22627.2 23011.8 19859.1 18964.8 21246.3 17549.1 19213.4 17393.1 22537.8 23948.0 17551.3 20286.4 20488.5 22540.2 20940.6 20236.5 25678.2 18105.8 18994.9 22477.0 17744.9 20824.6 18235.3 18812.3 22543.6 14944.2 22403.4 19138.6 15682.3 109.0405562_MZ Imidazole-4-acetaldehyde Un 1.0 None None None None Imidazole-4-acetaldehyde is a naturally occurring aldehyde metabolite of histamine formed by the action of histaminase (E.C. 1.4.3.6), and can be synthesized by oxidation of histidine. Aldehyde dehydrogenase (EC 1.2.1.3) is the only enzyme in the human liver capable of catalyzing dehydrogenation of aldehydes arising via monoamine, diamine, and plasma amine oxidases. NAD-linked dehydrogenation of short chain aliphatic aldehydes has been found in virtually every organ of the mammalian body. Imidazole-4-acetaldehyde is a good substrate for all aldehyde dehydrogenase isozymes. Experimentally, the prebiotic formation of histidine has been accomplished by the reaction of erythrose with formamidine followed by a Strecker synthesis. Imidazole-4-acetaldehyde could have been converted to histidine on the primitive earth by a Strecker synthesis, and several prebiotic reactions could convert imidazole-4-glycol and imidazole-4-ethanol to imidazole-4-acetaldehyde. (PMID: 2071588, 2957640, 11536478). C5H6N2O None None None 32781.1 29865.7 29235.9 25392.1 25942.2 31832.5 25158.9 31259.3 24620.7 22887.0 31097.7 29544.7 31108.2 28083.8 26113.7 34347.7 23273.0 29334.3 29381.0 27753.4 33094.7 26800.9 24857.8 29002.0 24320.6 27406.8 27217.9 27842.9 25963.3 27477.6 27065.5 27650.0 26263.9 23741.6 30726.8 34308.8 24771.1 24494.1 20659.1 25884.5 29334.5 31088.1 109.0658001_MZ 2,3-Butanediol Un 1.0 None None None None 2,3-Butanediol is an isomer of butanediol. The 2R,3R stereoisomer of 2,3-butanediol is produced by a variety of microorganisms, in a process known as butanediol fermentation. 2,3-Butanediol fermentation is the anaerobic fermentation of glucose with 2,3-butanediol as one of the end products. The overall stoichiometry of the reaction is 2 pyruvate + NADH --> 2CO2 + 2,3-butanediol. Butanediol fermentation is typical for Enterobacter species or microbes found in the gut. 2,3-butanediol has been identified in the sera of alcoholics and it may be a specific marker of alcohol abuse (PMID: 6139706). In humans, 2,3-butanediol is oxidized to acetyl-CoA via acetoin. 2,3-Butanediol is also found in cocoa butter. C4H10O2 None None None 6103.43 7192.64 8135.88 7203.27 8699.92 7863.95 7269.52 9412.5 6353.86 6825.12 7981.42 6915.64 4944.44 7267.77 8967.63 7351.61 11472.5 4211.21 5774.13 6268.61 6383.31 6198.33 6887.21 6423.13 6355.14 6422.9 8080.46 6479.93 5559.57 7475.44 5615.76 5531.73 5962.02 5741.52 5919.26 5886.07 5438.42 6450.29 4909.22 6903.66 4154.18 5564.45 110.0246430_MZ Pyrrole-2-carboxylic acid Un 1.0 None None None None Pyrrole-2-carboxylic acid was synthesized over a century ago, but its history as a compound of biological origin is rather recent. It was first identified as a degradation product of sialic acids, then as a derivative of the oxidation of the D-hydroxyproline isomers by mammalian D-amino acid oxidase. The latter relationship results from the lability of the direct oxidation product, A'-pyrroline-4-hydroxy-2-carboxylic acid, which loses water spontaneously to form the pyrrole. A similar reaction is catalyzed by the more specific allohydroxy-D-proline oxidase of Pseudomonas. In whole animal observations, pyrrole-2-carboxylate (PCA) ' was identified in rat or human urine after administration of the D-isomers of hydroxyproline, a finding ascribable to the action of D-amino acid oxidase. (PMID: 4430715). Urinary excretion of N-(pyrrole-2-carboxyl) glycine has been reported in a 5-year-old affected with type II hyperprolinemia; The child has mild developmental delay, recurrent seizures of the grand mal type and EEG alterations. The urinary excretion of the conjugate is stressed, since it appears that only one previous report in the literature described this compound in the urine of two patients affected by this disturbance. (PMID 2383933). C5H5NO2 None None None 16439.1 17073.8 17908.3 20587.5 15808.6 23408.2 19094.8 14883.3 18933.8 24919.1 15718.6 20143.2 22996.7 16901.1 19156.6 27320.5 14963.9 34857.1 21454.0 20134.1 15036.0 17450.1 18532.8 16191.6 18162.5 19278.5 17158.8 23583.3 20894.0 21483.9 13682.9 22833.8 19265.6 16878.9 20762.1 22071.5 18348.9 15941.6 20561.1 20572.4 19770.9 18895.3 110.0348772_MZ Cytosine Un 1.0 None None None None Cytosine is a pyrimidine base that is a fundamental unit of nucleic acids. The deamination of cytosine alone is apparent and the nucleotide of cytosine is the prime mutagenic nucleotide in leukaemia and cancer. C4H5N3O None None None 4307.57 4509.02 4825.05 5266.29 5093.69 5627.3 4613.22 4402.65 5200.79 5599.05 5302.37 5329.85 5103.44 5009.18 5290.12 5704.41 4519.81 6300.49 4852.29 4636.31 3981.0 4922.71 5066.89 4221.82 4540.23 5302.03 5209.9 4996.69 4794.56 5173.46 3864.73 4920.5 4826.79 4127.25 5161.84 4882.27 4912.66 4711.38 4232.55 5130.39 4193.16 4337.19 110.0723844_MZ Histamine Un 1.0 None None None None Histamine is an amine derived by enzymatic decarboxylation of histidine. It is a powerful stimulant of gastric secretion, a constrictor of bronchial smooth muscle, a vasodilator, and also a centrally acting neurotransmitter. C5H9N3 None None None 23735.4 22850.0 23021.0 17489.4 19970.3 30647.1 18905.9 18413.7 20820.9 15613.0 21882.6 20764.2 16987.2 20699.0 19877.4 46880.7 17926.9 15810.1 15532.3 19752.2 19044.2 18325.0 22427.3 22508.5 20150.0 15850.4 18897.2 19854.7 23762.5 25484.9 25275.3 32179.2 15191.2 16563.2 34728.8 19642.4 15678.0 20419.0 13971.1 19288.7 17888.4 17111.4 111.0087546_MZ 3-Furoic acid Un 1.0 None None None None 3-Furoic acid is an organic acid regularly occurring in urine of healthy individuals. (PMID 2338430). 3-Furoic acid is also a compound found in honey and honeydew samples (PMID 11403496), and is a structural analog of nicotinic acid (niacin, a vitamin of the B complex). (PMID 12563315). C5H4O3, 2-Furoic acid None None None 74010.6 76236.1 101517.0 64469.7 114878.0 77000.8 108259.0 106688.0 113969.0 91473.0 98016.8 98484.3 91922.1 133166.0 113601.0 54813.3 109360.0 72285.5 88898.1 89974.6 84983.0 94739.0 79310.6 83984.8 105705.0 94960.4 129242.0 76400.1 81301.3 89988.9 78147.7 61754.4 105829.0 90210.7 87353.6 63196.2 101898.0 106703.0 80499.2 86348.2 85333.9 81229.7 111.0198218_MZ Uracil Un 1.0 None None None None Uracil is a common naturally occurring pyrimidine found in RNA, it base pairs with adenine and is replaced by thymine in DNA. Methylation of uracil produces thymine. Uracil's use in the body is to help carry out the synthesis of many enzymes necessary for cell function through bonding with riboses and phosphates. Uracil serves as allosteric regulator and coenzyme for many important biochemical reactions. UDP and UTP regulate CPSase II activity in animals. UDP-glucose regulates the conversion of glucose to galactose in the liver and other tissues in the process of carbohydrate metabolism. Uracil is also involved in the biosynthesis of polysaccharides and the transportation of sugars containing aldehydes. C4H4N2O2 None None None 76071.9 79727.4 93836.7 87810.5 81912.4 111002.0 94495.3 76586.5 101065.0 120730.0 69318.3 106105.0 122021.0 89296.9 100349.0 120046.0 81004.6 193581.0 111549.0 96401.3 73188.2 87505.9 90130.8 79254.2 91295.4 96796.0 93949.1 120565.0 108349.0 107300.0 63441.5 95624.3 107966.0 86266.2 108457.0 105478.0 98640.5 84892.6 103529.0 105064.0 98389.8 97135.1 111.0449922_MZ trans-1,2-Dihydrobenzene-1,2-diol Un 1.0 None None None None Trans-1,2-Dihydrobenzene-1,2-diol is an intermediate in the metabolism of Prostaglandin and leukotriene. It is a substrate for Aldo-keto reductase family 1 member C3, Aldo-keto reductase family 1 member C4, Aldo-keto reductase family 1 member C2 and Aldo-keto reductase family 1 member C1. C6H8O2 None None None 14196.0 19029.7 20976.8 18772.7 26181.4 21166.0 18929.4 21153.3 19353.2 19539.6 24582.5 23796.2 12386.0 21786.7 24910.8 17908.3 22559.9 12988.0 15929.6 15753.8 15889.7 19473.5 18802.6 16393.1 17757.9 18370.3 21893.9 18933.2 17726.2 20259.7 13996.1 14616.3 21373.7 15577.6 17966.5 15653.9 16016.1 21208.4 13642.0 19262.6 11293.8 14184.9 112.0408009_MZ 1-Pyrroline-5-carboxylic acid Un 1.0 None None None None 1-Pyrroline-5-carboxylic acid is an enamine or an imino acid that forms on spontaneous dehydration of L-glutamate γ-semialdehyde in aqueous solutions. The stereoisomer (S)-1-Pyrroline-5-carboxylate is an intermediate in glutamate metabolism, in arginine degradation and in proline biosynthesis and degradation and it can be converted to or be formed from the three amino acids L-glutamate, L-ornithine and L-proline. In particular, it is synthesized with the oxidation of proline by pyrroline-5-carboxylate reductase 1 (EC 1.5.1.2, PYCR1) or by proline dehydrogenase (EC 1.5.99.8, PRODH) and it is hydrolyzed to L-glutamate by delta-1-pyrroline-5-carboxylate dehydrogenase (EC 1.5.1.12, ALDH4A1). It is also one of the few metabolites that can be a precursor to other metabolites of both the urea cycle and the tricarboxylic acid (TCA) cycle. C5H7NO2, 1-Pyrroline-2-carboxylic acid None None None 10019.1 8701.93 9418.02 18140.8 9997.16 10107.8 11838.1 10565.2 9258.4 8705.97 13050.9 7995.41 10291.9 8923.88 10463.4 10263.9 9890.79 10044.3 9949.03 8757.19 10076.7 6955.3 10542.1 12728.5 9387.11 8040.63 13068.1 9688.71 7524.69 8316.91 9921.72 9281.08 6376.84 9578.54 7292.33 10377.4 8127.14 8558.22 6768.59 11033.8 9073.14 11421.7 112.0516579_MZ Creatinine Un 1.0 None None None None Creatinine or creatine anhydride, is a breakdown product of creatine phosphate in muscle. The loss of water molecule from creatine results in the formation of creatinine. Creatinine is transferred to the kidneys by blood plasma, whereupon it is eliminated from the body by glomerular filtration and partial tubular excretion. Creatinine is usually produced at a fairly constant rate by the body. Measuring serum creatinine is a simple test and it is the most commonly used indicator of renal function. A rise in blood creatinine levels is observed only with marked damage to functioning nephrons; therefore this test is not suitable for detecting early kidney disease. The typical reference range for women is considered about 45-90 umol/l, for men 60-110 umol/l. Creatine and creatinine are metabolized in the kidneys, muscle, liver and pancreas. C4H7N3O None None None 18609.7 24027.2 45984.3 24316.4 22521.2 21749.4 26682.6 26173.3 23335.4 24105.6 24001.0 27988.9 18309.3 24689.4 24537.8 24262.0 19522.8 41795.0 21010.7 24390.8 24955.1 31646.2 21277.6 23731.3 21091.0 43634.2 21624.6 41201.5 41517.9 38801.7 19911.7 20878.5 21703.1 29528.8 58576.4 25889.5 19885.5 28508.2 21478.6 22051.2 16934.1 20939.5 113.0971535_MZ 4-Heptanone Un 1.0 None None None None 4-heptanone is a volatile organic ketone found in almost all urine samples of normal individuals. (PMID 15996539). It has been hypothesized that arises from in vivo beta-oxidation of 2-ethylhexanoic acid (EHA) from plasticizers, similar to formation of 3-heptanone from valproic acid. (PMID 11282094). C7H14O, 2-Heptanone, Ethyl isobutyl ketone None None None 2251.05 3243.07 3213.35 3022.16 4779.16 4372.82 2769.35 2316.86 2900.84 3064.33 3913.48 3713.38 1743.06 3749.19 4389.52 2628.37 2118.06 1417.78 2247.86 2050.44 2972.53 2980.13 3115.44 2685.73 2572.32 2768.7 4143.57 2605.14 2759.0 3212.35 2014.83 2496.32 3883.87 2294.26 3454.33 2196.76 2554.78 4327.47 1739.75 2892.41 1563.76 1832.34 114.0561021_MZ L-Proline Un 1.0 None None None None L-Proline is one of the twenty amino acids used in living organisms as the building blocks of proteins. Proline is sometimes called an imino acid, although the IUPAC definition of an imine requires a carbon-nitrogen double bond. Proline is a non-essential amino acid that is synthesized from glutamic acid. It is an essential component of collagen and is important for proper functioning of joints and tendons. C5H9NO2, Acetamidopropanal None None None 145356.0 200421.0 122194.0 72602.0 94603.2 199625.0 90470.7 107889.0 98003.0 92597.0 96895.2 121335.0 100853.0 142968.0 96212.1 246052.0 85201.0 159219.0 119943.0 144253.0 139965.0 109203.0 119724.0 148401.0 88247.6 94253.6 97932.7 106046.0 143178.0 221363.0 114756.0 131432.0 100703.0 86129.8 125943.0 136852.0 95785.6 123691.0 66537.8 113473.0 79805.2 92527.4 115.0036897_MZ Fumaric acid Un 1.0 None None None None Fumaric acid is a precursor to L-malate in the Krebs tricarboxylic acid cycle. It is formed by the oxidation of succinate by succinate dehydrogenase. Fumarate is converted by fumarase to malate. A fumarate is a salt or ester of the organic compound fumaric acid, a dicarboxylic acid. (wikipedia). C4H4O4, Maleic acid None None None 563525.0 685573.0 633192.0 531417.0 801202.0 425076.0 672280.0 961985.0 555886.0 439290.0 634808.0 669170.0 761238.0 477902.0 753516.0 549518.0 700792.0 430433.0 638637.0 596446.0 676373.0 682099.0 636584.0 776210.0 685276.0 677139.0 841654.0 601585.0 686593.0 356954.0 730773.0 756084.0 533172.0 532471.0 681958.0 574688.0 534427.0 715547.0 553305.0 792878.0 583621.0 687271.0 115.0765001_MZ Caproic acid Un 1.0 None None None None Caproic acid is a colorless oily liquid smelling of cheese. It is a fatty acid found naturally in various animal fats and oils. Caproic acid is a medium chain triglycerides (MCT). MCTs are widely used for parenteral nutrition in individuals requiring supplemental nutrition and are being more widely used in foods, drugs and cosmetics; they are essentially non-toxic. It is safe for human dietary consumption up to levels of 1g/kg. (PMID 10685018). C6H12O2, Isocaproic acid None None None 35491.6 40376.9 35250.4 34370.9 41430.1 43588.7 33828.5 34237.3 28964.2 34948.9 36719.2 29966.6 21819.0 42602.9 41240.9 29664.9 34516.4 25897.2 25822.8 24729.0 35363.0 30508.7 37138.5 44186.8 27370.8 28382.9 38137.1 29985.0 28232.0 38488.7 26146.9 28896.4 30002.8 29557.3 35367.8 32013.2 27874.1 33189.6 26096.9 36569.3 19587.1 29304.0 116.0352151_MZ L-Aspartate-semialdehyde Un 1.0 None None None None L-Aspartate-semialdehyde is involved in both the lysine biosynthesis I and homoserine biosynthesis pathways. In the lysine biosynthesis I pathway, L-Aspartate-semialdehyde is produce from a reaction between L-aspartyl-4-phosphate and NADPH, with phosphate and NADP+ as byproducts. The reaction is catalyzed by aspartate-semialdehyde dehydrogenase. L-Aspartate-semialdehyde reacts with pyruvate to produce L-2,3-dihydrodipicolinate and water. Dihydrodipicolinate synthase catalyzes this reaction. In the homoserine biosynthesis pathway, L-Aspartate-semialdehyde is produce from a reaction between L-aspartyl-4-phosphate and NADPH, with phosphate and NADP+ as byproducts. The reaction is catalyzed by aspartate-semialdehyde dehydrogenase. L-Aspartate-semialdehyde reacts with NAD(P)H and H+ to form homoserine and NAD(P)+. C4H7NO3, Acetylglycine, L-2-Amino-3-oxobutanoic acid None None None 15414.8 12139.8 17543.4 49998.7 14920.7 15734.0 17365.2 18140.7 17452.3 15121.2 21667.0 27018.8 12012.8 19112.4 13474.8 15538.9 16054.7 8529.92 12485.6 9784.55 13131.5 17833.4 20049.8 13594.9 13722.3 12429.1 13724.2 18021.3 16919.3 11714.6 14676.1 21135.5 9975.7 14520.9 11997.6 18061.8 14946.2 22868.7 7435.43 17499.4 8411.25 12537.8 116.0504057_MZ Indole Un 1.0 None None None None Indole is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. It can be produced by bacteria as a degradation product of the amino acid tryptophan. It occurs naturally in human feces and has an intense fecal smell. At very low concentrations, however, it has a flowery smell, and is a constituent of many flower scents (such as orange blossoms) and perfumes. Natural jasmine oil, used in the perfume industry, contains around 2.5% of indole. Indole also occurs in coal tar. The participation of the nitrogen lone electron pair in the aromatic ring means that indole is not a base, and it does not behave like a simple amine. C8H7N None None None 13388.7 12061.5 12596.5 10505.2 11305.0 15124.3 11201.9 11045.3 13143.8 11477.4 10782.0 15779.5 14396.4 13508.2 12432.8 13031.4 10636.0 12838.6 12423.7 13034.3 12994.7 12871.8 11854.2 11322.9 10503.6 10160.1 12983.2 12241.1 13017.8 12243.5 9340.19 10359.2 13318.5 10630.1 15519.7 13192.5 11212.4 11516.8 8594.88 12384.8 10376.2 10890.2 116.0717491_MZ L-Valine Un 1.0 None None None None Valine (abbreviated as Val or V) is an -amino acid with the chemical formula HO2CCH(NH2)CH(CH3)2. It is named after the plant valerian. L-Valine is one of 20 proteinogenic amino acids. Its codons are GUU, GUC, GUA, and GUG. This essential amino acid is classified as nonpolar. Along with leucine and isoleucine, valine is a branched-chain amino acid. Branched chain amino acids (BCAA) are essential amino acids whose carbon structure is marked by a branch point. These three amino acids are critical to human life and are particularly involved in stress, energy and muscle metabolism. BCAA supplementation as therapy, both oral and intravenous, in human health and disease holds great promise. BCAA denotes valine, isoleucine and leucine which are branched chain essential amino acids. Despite their structural similarities, the branched amino acids have different metabolic routes, with valine going solely to carbohydrates, leucine solely to fats and isoleucine to both. The different metabolism accounts for different requirements for these essential amino acids in humans: 12 mg/kg, 14 mg/kg and 16 mg/kg of valine, leucine and isoleucine respectively. Furthermore, these amino acids have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors. Many types of inborn errors of BCAA metabolism exist, and are marked by various abnormalities. The most common form is the maple syrup urine disease, marked by a characteristic urinary odor. Other abnormalities are associated with a wide range of symptoms, such as mental retardation, ataxia, hypoglycemia, spinal muscle atrophy, rash, vomiting and excessive muscle movement. Most forms of BCAA metabolism errors are corrected by dietary restriction of BCAA and at least one form is correctable by supplementation with 10 mg of biotin daily. BCAA are decreased in patients with liver disease, such as hepatitis, hepatic coma, cirrhosis, extrahepatic biliary atresia or portacaval shunt; aromatic amino acids (AAA)‰ÛÓtyrosine, tryptophan and phenylalanine, as well as methionine‰ÛÓare increased in these conditions. Valine in particular, has been established as a useful supplemental therapy to the ailing liver. All the BCAA probably compete with AAA for absorption into the brain. Supplemental BCAA with vitamin B6 and zinc help normalize the BCAA:AAA ratio. (http://www.dcnutrition.com). In sickle-cell disease, valine substitutes for the hydrophilic amino acid glutamic acid in hemoglobin. Because valine is hydrophobic, the hemoglobin does not fold correctly. Valine is an essential amino acid, hence it must be ingested, usually as a component of proteins. C5H11NO2, N-Methyl-a-aminoisobutyric acid, 5-Aminopentanoic acid None None None 261109.0 251500.0 278800.0 166954.0 292593.0 296060.0 261445.0 201644.0 237542.0 196153.0 199559.0 261535.0 267684.0 225297.0 222713.0 311121.0 208806.0 285918.0 248165.0 284522.0 260464.0 249800.0 258233.0 259066.0 250095.0 230101.0 236347.0 258497.0 340711.0 270588.0 178149.0 217531.0 255253.0 166623.0 311990.0 276337.0 225357.0 255430.0 146750.0 255996.0 244942.0 228092.0 117.0192773_MZ Methylmalonic acid Un 1.0 None None None None Methylmalonic acid is a malonic acid derivative which is a vital intermediate in the metabolism of fat and protein. Abnormalities in methylmalonic acid metabolism lead to methylmalonic aciduria. This metabolic disease is attributed to a block in the enzymatic conversion of methylmalonyl CoA to succinyl CoA. C4H6O4, Succinic acid, Erythrono-1,4-lactone, Threonolactone None None None 659100.0 848206.0 698358.0 364294.0 846334.0 772683.0 703073.0 752514.0 837238.0 763458.0 776932.0 852079.0 692852.0 617283.0 766862.0 747923.0 546873.0 934812.0 799048.0 644986.0 749136.0 750288.0 721974.0 797942.0 634563.0 806253.0 725005.0 891833.0 726805.0 667163.0 568457.0 727571.0 828450.0 686616.0 803521.0 817123.0 761071.0 772200.0 547395.0 876429.0 609657.0 824399.0 117.0556099_MZ 2-Hydroxy-3-methylbutyric acid Un 1.0 None None None None 2-Hydroxy-3-methylbutyric acid (also known as 2-Hydroxyisovaleric acid) is a metabolite found in the urine of patients with Phenylketonuria (PMID 7978272), Methylmalonic acidemia, Propionic acidemia, 3-Ketothiolase deficiency, Isovaleric acidemia, 3-Methylcrotonylglycemia, 3-Hydroxy-3-methylglutaric acidemia, Multiple carboxylase deficiency, Glutaric aciduria, Ornithine transcarbamylase deficiency, glyceroluria, Tyrosinemia type 1, Galactosemia, and Maple syrup urine disease (PMID 11048741). 2-hydroxyisovaleric acid has been identified in the urine of patients with lactic and ketoacidosis (PMID: 884872). It has also been identified in the urine of severely asphyxiated babies (PMID: 1610944). 2-hydroxyisovaleric acid originates mainly from ketogenesis and from the metabolism of valine, leucine and isoleucine (PMID: 6434570). C5H10O3, 3-Hydroxy-2-methyl-[R-(R,S)]-butanoic acid, 2-Methyl-3-hydroxybutyric acid, 2-Ethylhydracrylic acid, 3-Hydroxy-2-methyl-[S-(R,R)]-butanoic acid, 3-Hydroxyvaleric acid, Erythronilic acid, 3-Hydroxyisovaleric acid, 2-Hydroxyvaleric acid. 2-Hydroxy-2-methylbutyric acid, 4-Hydroxyisovaleric acid None None None 26142.9 15846.5 32428.5 23754.8 27215.5 22276.9 17162.0 31333.5 21740.3 13888.3 16985.7 19974.1 17303.7 18400.4 25390.9 17193.8 15335.0 20598.1 19761.3 16531.6 18857.4 21153.8 26833.3 23896.5 17177.8 26319.0 18750.8 18635.5 19151.8 18615.9 12384.5 14979.4 13253.9 24872.7 25938.4 23008.1 20290.0 26387.7 18010.7 29978.8 13709.7 16398.0 118.0509686_MZ L-Threonine Un 1.0 None None None None Threonine is an essential amino acid in humans. It is abundant in human plasma, particularly in newborns. Severe deficiency of threonine causes neurological dysfunction and lameness in experimental animals. Threonine is an immunostimulant which promotes the growth of thymus gland. It also can probably promote cell immune defense function. This amino acid has been useful in the treatment of genetic spasticity disorders and multiple sclerosis at a dose of 1 gram daily. It is highly concentrated in meat products, cottage cheese and wheat germ. (http://www.dcnutrition.com/AminoAcids/) The threonine content of most of the infant formulas currently on the market is approximately 20% higher than the threonine concentration in human milk. Due to this high threonine content the plasma threonine concentrations are up to twice as high in premature infants fed these formulas than in infants fed human milk. The whey proteins which are used for infant formulas are sweet whey proteins. Sweet whey results from cheese production. Threonine catabolism in mammals appears to be due primarily (70-80%) to the activity of threonine dehydrogenase (EC 1.1.1.103) that oxidizes threonine to 2-amino-3-oxobutyrate, which forms glycine and acetyl CoA, whereas threonine dehydratase (EC 4.2.1.16) that catabolizes threonine into 2-oxobutyrate and ammonia, is significantly less active. Increasing the threonine plasma concentrations leads to accumulation of threonine and glycine in the brain. Such accumulation affects the neurotransmitter balance which may have consequences for the brain development during early postnatal life. Thus, excessive threonine intake during infant feeding should be avoided. (PMID 9853925). C4H9NO3, L-Homoserine, L-Allothreonine None None None 48144.3 47522.4 45725.3 31262.5 39118.9 56981.2 38331.4 44289.3 42896.9 33782.4 42865.9 41501.1 35651.6 44733.8 39051.1 76309.8 31696.8 44840.7 38306.5 48653.5 43380.2 39682.9 47254.1 50125.5 37218.0 31244.9 39203.7 41466.7 52966.1 61599.0 46935.0 58084.3 33737.9 30213.5 48224.4 47267.4 36657.4 46056.4 27087.2 43694.7 30496.6 34829.2 118.9804540_MZ 3-Mercaptopyruvic acid Un 1.0 None None None None 3-Mercaptopyruvic acid is an intermediate in the metabolism of Cysteine. It is a substrate for L-lactate dehydrogenase A chain, 3-mercaptopyruvate sulfurtransferase, Aspartate aminotransferase (mitochondrial), L-lactate dehydrogenase C chain, L-lactate dehydrogenase A-like 6A, Aspartate aminotransferase (cytoplasmic), L-lactate dehydrogenase B chain and L-lactate dehydrogenase A-like 6B. C3H4O3S None None None 273879.0 207363.0 267459.0 88650.6 203600.0 349882.0 256538.0 174957.0 281518.0 300985.0 233954.0 276701.0 333268.0 181550.0 267042.0 195456.0 142968.0 454637.0 327561.0 327131.0 233966.0 295880.0 261845.0 253250.0 257089.0 234440.0 214754.0 291092.0 300161.0 254167.0 132230.0 156548.0 333786.0 244344.0 268881.0 336472.0 260971.0 270541.0 187373.0 313799.0 234868.0 255824.0 119.0501380_MZ 4-Hydroxystyrene Un 1.0 None None None None 4-hydroxystyrene occurs frequently in different ciders, wines, foods and berries, e.g. cloudberry. Styrene is a prohapten metabolized in the skin by aryl hydrocarbon hydroxylase (AHH, EC 1.14.14.1) to styrene epoxide acting as the true hapten. Styrene occurs in nature and as a synthetic product.(PMID: 6713846). C8H8O, Phenylacetaldehyde None None None 29969.6 31525.9 25666.7 26535.3 28035.9 31828.4 24857.2 29038.5 28844.7 27610.4 27090.1 27198.8 28603.7 31066.2 26823.7 25493.7 33492.8 25043.2 31676.9 27788.1 27326.7 27606.9 28199.6 28006.6 28621.9 25678.6 25221.5 28885.8 24361.7 38450.5 23115.1 21489.5 25799.0 25657.8 26342.7 27356.9 25673.2 24041.8 29120.3 26342.9 20535.4 24619.9 120.0453765_MZ Benzamide Un 1.0 None None None None Benzamide is an intermediate in the Benzoate degradation via CoA ligation. Benzamides are a class of chemical compounds derived from Benzamid, the carbonic acid amide of benzoic acid. In psychiatry some substituted benzamides are therapeutically used as neuroleptics and/or antipsychotics (wikipedia). C7H7NO None None None 4740.86 4584.85 4693.55 4660.87 4252.0 4726.78 5246.63 5342.18 4063.25 4280.0 4389.59 4431.22 4207.24 4570.52 4541.22 4469.9 5079.09 5418.51 4036.39 4942.43 4174.92 3733.93 4451.29 4393.3 4326.26 4363.98 4142.06 4749.01 4094.94 4882.43 4617.83 4134.53 3699.59 4607.26 4238.92 4616.47 4094.92 3395.04 3775.94 4275.26 4994.38 4129.98 120.9963797_MZ 3-Mercaptolactic acid Un 1.0 None None None None 3-Mercaptolactic acid is a thiol that has been confirmed to be found in urine (PMID 8852041). C3H6O3S None None None 25100.8 10405.8 13363.7 11396.4 10570.7 37998.6 21151.2 19390.8 31721.8 16088.9 23116.8 14154.9 14396.5 11712.7 15617.5 22752.2 7649.58 20096.1 15540.8 15034.2 14963.5 14293.8 12270.6 12427.1 12775.7 13029.0 10540.1 13394.7 14664.5 12478.3 7987.58 8718.33 15852.2 12197.3 12956.3 21578.8 13118.4 21059.0 9102.25 14236.9 12719.1 20961.6 121.0294623_MZ Benzoic acid Un 1.0 None None None None Benzoic acid, C6H5COOH, is a colourless crystalline solid and the simplest aromatic carboxylic acid. Benzoic acid occurs naturally free and bound as benzoic acid esters in many plant and animal species. Appreciable amounts have been found in most berries (around 0.05%). Cranberries contain as much as 300-1300 mg free benzoic acid per kg fruit. Benzoic acid is a fungistatic compound that is widely used as a food preservative. It often is conjugated to glycine in the liver and excreted as hippuric acid. Benzoic acid is a byproduct of phenylalanine metabolism in bacteria. It is also produced when gut bacteria process polyphenols (from ingested fruits or beverages). C7H6O2, 4-Hydroxybenzaldehyde None None None 160994.0 164261.0 134096.0 151729.0 150405.0 173504.0 227628.0 209830.0 95387.1 152050.0 127701.0 74373.9 155511.0 160373.0 161372.0 128112.0 229489.0 198879.0 160653.0 203965.0 140305.0 79222.2 125568.0 180133.0 138879.0 80541.8 151876.0 155072.0 70811.9 168103.0 177232.0 122385.0 64452.8 169248.0 78664.6 158314.0 96070.2 63845.2 112823.0 163086.0 196884.0 159610.0 121.0405399_MZ Niacinamide Un 1.0 None None None None Niacinamide or vitamin B3 is an important compound functioning as a component of the coenzyme NAD. Its primary significance is in the prevention and/or cure of blacktongue and pellagra. Most animals cannot manufacture this compound in amounts sufficient to prevent nutritional deficiency and it therefore must be supplemented through dietary intake. Niacinamide is used to increase the effect of radiation therapy on tumor cells. Niacin (nicotinic acid) and niacinamide, while both labeled as vitamin B3 also have different applications. Niacinamide is useful in arthritis and early-onset type I diabetes while niacin is an effective reducer of high cholesterol levels. C6H6N2O None None None 68878.6 69351.5 80556.2 76741.2 82416.8 68176.0 126031.0 81359.1 77978.4 71194.4 57105.8 83453.9 71924.4 60431.6 86100.5 71005.1 83902.4 90518.4 85597.0 89163.1 66299.8 84211.2 64037.8 76728.9 71618.3 90364.4 109444.0 81348.9 78592.3 81296.2 88524.5 63564.6 66702.1 76148.2 85303.1 82044.9 65379.5 85197.0 68170.3 79277.4 90278.5 91377.9 122.0247599_MZ Nicotinic acid Un 1.0 None None None None Nicotinic acid, also known as niacin or vitamin B3, is a water-soluble vitamin whose derivatives such as NADH, NAD, NAD+, and NADP play essential roles in energy metabolism in the living cell and DNA repair. The designation vitamin B3 also includes the amide form, nicotinamide or niacinamide. Severe lack of niacin causes the deficiency disease pellagra, whereas a mild deficiency slows down the metabolism decreasing cold tolerance. The recommended daily allowance of niacin is 2-12 mg a day for children, 14 mg a day for women, 16 mg a day for men, and 18 mg a day for pregnant or breast-feeding women. It is found in various animal and plant tissues and has pellagra-curative, vasodilating, and antilipemic properties. The liver can synthesize niacin from the essential amino acid tryptophan (see below), but the synthesis is extremely slow and requires vitamin B6; 60 mg of tryptophan are required to make one milligram of niacin. Bacteria in the gut may also perform the conversion but are inefficient. C6H5NO2, Picolinic acid None None None 14137.2 10969.6 10860.3 10777.8 11270.7 14496.8 12726.2 10664.7 10729.7 13659.1 11875.8 11340.9 11716.5 14646.8 11145.3 11802.1 10664.8 13452.4 10811.0 11278.8 11876.0 11634.5 12530.3 12039.0 10799.4 12008.6 10471.7 13148.1 12513.0 15869.1 10082.7 11644.1 10932.0 10692.2 11225.1 11396.5 11208.0 11241.8 12563.8 11049.0 10757.7 11221.0 124.0073856_MZ Taurine Un 1.0 None None None None Taurine is a sulfur amino acid like methionine, cystine, cysteine and homocysteine. It is a lesser-known amino acid because it is not incorporated into the structural building blocks of protein. Yet taurine is an essential amino acid in pre-term and newborn infants of humans and many other species. Adults can synthesize their own taurine, yet are probably dependent in part on dietary taurine. Taurine is abundant in the brain, heart, breast, gallbladder and kidney and has important roles in health and disease in these organs. Taurine has many diverse biological functions serving as a neurotransmitter in the brain, a stabilizer of cell membranes and a facilitator in the transport of ions such as sodium, potassium, calcium and magnesium. Taurine is highly concentrated in animal and fish protein, which are good sources of dietary taurine. It can be synthesized by the body from cysteine when vitamin B6 is present. Deficiency of taurine occurs in premature infants and neonates fed formula milk, and in various disease states. Inborn errors of taurine metabolism have been described. OMIM 168605, an unusual neuropsychiatric disorder inherited in an autosomal dominant fashion through 3 generations of a family. Symptoms began late in the fifth decade in 6 affected persons and death occurred after 4 to 6 years. The earliest and most prominent symptom was mental depression not responsive to antidepressant drugs or electroconvulsive therapy. Sleep disturbances, exhaustion and marked weight loss were features. Parkinsonism developed later, and respiratory failure occurred terminally. OMIM 145350 describes congestive cardiomyopathy and markedly elevated urinary taurine levels (about 5 times normal). Other family members had late or holosystolic mitral valve prolapse and elevated urinary taurine values (about 2.5 times normal). In 2 with mitral valve prolapse, congestive cardiomyopathy eventually developed while the amounts of urinary taurine doubled. Taurine, after GABA, is the second most important inhibitory neurotransmitter in the brain. Its inhibitory effect is one source of taurine's anticonvulsant and antianxiety properties. It also lowers glutamic acid in the brain, and preliminary clinical trials suggest taurine may be useful in some forms of epilepsy. Taurine in the brain is usually associated with zinc or manganese. The amino acids alanine and glutamic acid, as well as pantothenic acid, inhibit taurine metabolism while vitamins A and B6, zinc and manganese help build taurine. Cysteine and B6 are the nutrients most directly involved in taurine synthesis. Taurine levels have been found to decrease significantly in many depressed patients. One reason that the findings are not entirely clear is because taurine is often elevated in the blood of epileptics who need it. It is often difficult to distinguish compensatory changes in human biochemistry from true metabolic or deficiency disease. Low levels of taurine are found in retinitis pigmentosa. Taurine deficiency in experimental animals produces degeneration of light-sensitive cells. Therapeutic applications of taurine to eye disease are likely to be forthcoming. Taurine has many important metabolic roles. Supplements can stimulate prolactin and insulin release. The parathyroid gland makes a peptide hormone called glutataurine (glutamic acid-taurine), which further demonstrates taurine's role in endocrinology. Taurine increases bilirubin and cholesterol excretion in bile, critical to normal gallbladder function. It seems to inhibit the effect of morphine and potentiates the effects of opiate antagonists. Low plasma taurine levels have been found in a variety of conditions, i.e., depression, hypertension, hypothyroidism, gout, institutionalized patients, infertility, obesity, kidney failure and others. (http://www.dcnutrition.com/AminoAcids/). C2H7NO3S None None None 16994900.0 17086100.0 19444500.0 19996400.0 19667000.0 17645800.0 17552300.0 12661000.0 16983500.0 15311000.0 17653000.0 17476200.0 17925600.0 18964100.0 18025100.0 18315900.0 18692400.0 15557000.0 18586100.0 14883100.0 19828200.0 17838400.0 17801000.0 17274700.0 16787000.0 17219600.0 18476300.0 17537400.0 17015900.0 17781500.0 18370500.0 17698600.0 17079300.0 16035700.0 19256100.0 18373700.0 17224000.0 17395500.0 12676400.0 17412200.0 18254300.0 17691300.0 124.9912492_MZ 2-Hydroxyethanesulfonate Un 1.0 None None None None Isethionic acid C2H6O4S is a short chain alkane sulfonate containing hydroxy group, is a water soluble liquid used in the manufacture of mild, biodegradable and high foaming anionic surfactants which provides gentle cleansing and soft skin feel. A colorless, syrupy, strongly acidic liquid that can form detergents with oleic acid. C2H6O4S None None None 507712.0 443775.0 474717.0 425296.0 505267.0 611837.0 646107.0 449905.0 480387.0 610536.0 493426.0 253235.0 713629.0 446612.0 566412.0 372284.0 613000.0 557597.0 699512.0 476934.0 596232.0 339975.0 556641.0 586629.0 478250.0 267794.0 496310.0 465662.0 283530.0 588307.0 352289.0 398746.0 263650.0 501625.0 312128.0 744298.0 420670.0 288684.0 296669.0 597498.0 463808.0 627854.0 127.0512007_MZ Dihydrothymine Un 1.0 None None None None Dihydrothymine is an intermediate breakdown product of thymine. Dihydropyrimidine dehydrogenase catalyzes the reduction of thymine to 5, 6-dihydrothymine then dihydropyrimidinase hydrolyzes 5, 6-dihydrothymine to N-carbamyl-b-alanine. Finally, beta-ureidopropionase catalyzes the conversion of N-carbamyl-b-alanine to beta-alanine. Patients with dihydropyrimidinase deficiency exhibit highly increased concentrations of 5, 6-dihydrouracil and 5, 6-dihydrothymine and moderately increased concentrations of uracil and thymine can be detected in urine. C5H8N2O2 None None None 309258.0 282078.0 277825.0 247951.0 254794.0 273183.0 213818.0 313848.0 223551.0 212768.0 309897.0 316951.0 267915.0 268831.0 248876.0 316355.0 202692.0 271224.0 308948.0 253488.0 331961.0 274080.0 210429.0 286310.0 203131.0 305811.0 248050.0 259598.0 255828.0 243383.0 225191.0 260476.0 265409.0 213539.0 314938.0 368377.0 223077.0 214305.0 191135.0 244562.0 285612.0 310381.0 128.0353384_MZ Pyroglutamic acid Un 1.0 None None None None Pyroglutamic acid is a cyclized derivative of L-glutamic acid. It is an uncommon amino acid derivative in which the free amino group of glutamic acid cyclizes to form a lactam. It is formed nonenzymatically from glutamate, glutamine, and gamma-glutamylated peptides, but it can also be produced by the action of gamma-glutamylcyclotransferase on an L-amino acid. Elevated blood levels may be associated with problems of glutamine or glutathione metabolism. This compound is found in substantial amounts in brain tissue and other tissue in bound form, especially skin. Also present in plant tissues. It is sold, over the counter, as a smart drug for improving blood circulation in the brain. C5H7NO3, 1-Pyrroline-4-hydroxy-2-carboxylate, N-Acryloylglycine, Pyrrolidonecarboxylic acid, Pyrroline hydroxycarboxylic acid None None None 599052.0 578868.0 567457.0 516095.0 537762.0 533051.0 525522.0 730261.0 440768.0 466242.0 516296.0 521220.0 602694.0 542407.0 548306.0 573568.0 533184.0 625797.0 547364.0 486667.0 587629.0 464316.0 478270.0 545159.0 573368.0 492174.0 529520.0 520823.0 559013.0 468366.0 547829.0 569944.0 490496.0 428866.0 601003.0 555404.0 480702.0 487360.0 465255.0 529033.0 651609.0 573170.0 128.0714741_MZ Pipecolic acid Un 1.0 None None None None Pipecolic acid is a metabolite of lysine found in human physiological fluids such as urine, plasma and CSF. However, it is uncertain if pipecolic acid originates directly from food intake or from mammalian or intestinal bacterial enzyme metabolism. Recent studies suggest that plasma pipecolic acid, particularly the D-isomer, originates mainly from the catabolism of dietary lysine by intestinal bacteria rather than by direct food intake. In classic Zellweger syndrome (a cerebro-hepato-renal genetic disorder, OMIM 214100) pipecolic acid accumulate in the plasma of the patients. It is known that plasma pipecolic acid levels are also elevated in patients with chronic liver diseases. Pipecolic acid is moderately elevated in patients with pyridoxine-dependent seizures and might therefore be a possible biochemical marker for selecting candidates for pyridoxine therapy (Plecko et al 2000). Pipecolic acid was also elevated in CSF in these vitamin B6-responsive patients. (PMID 12705501). C6H11NO2, L-Pipecolic acid, N4-Acetylaminobutanal, D-Pipecolic acid None None None 12168.8 13380.8 18485.0 18077.0 17356.5 12031.5 18846.1 19358.0 16287.6 10570.3 14546.1 14828.5 15781.9 12861.8 26456.5 12831.4 15540.7 14381.4 14306.0 13815.7 23197.4 16852.4 14358.5 13103.6 20018.3 26723.4 11624.6 20354.8 17242.5 13295.5 14232.9 15255.1 12948.3 15643.3 15261.2 15467.7 16973.1 14426.0 8679.34 17975.6 17120.0 17941.6 129.0192840_MZ Mesaconic acid Un 1.0 None None None None Mesaconic acid is one of several isomeric carboxylic acids obtained from citric acid. Is used as a fire retardant, recent studies revealed this acid is a competitive inhibitor of fumarate reduction. C5H6O4, Itaconic acid, Glutaconic acid, Gamma-delta-Dioxovaleric acid, Citraconic acid None None None 135465.0 138829.0 153628.0 161217.0 161272.0 193506.0 156159.0 116028.0 142801.0 161328.0 160217.0 145478.0 108357.0 195421.0 178052.0 118921.0 119866.0 78293.9 126022.0 112522.0 138146.0 138231.0 137574.0 129674.0 129547.0 118820.0 156842.0 116649.0 122853.0 181661.0 125683.0 134793.0 128756.0 107642.0 149314.0 120794.0 122540.0 135461.0 91654.4 145925.0 95579.3 101611.0 129.0556350_MZ Ketoleucine Un 1.0 None None None None Ketoleucine is a metabolite that accumulates in Maple Syrup Urine Disease (MSUD) and shown to compromise brain energy metabolism by blocking the respiratory chain; this is of relevance to the understanding of the pathophysiology of the neurological dysfunction of MSUD patients. (PMID 14636955). C6H10O3, 2-Methyl-3-ketovaleric acid, 3-Methyl-2-oxovaleric acid, 2-Ketohexanoic acid, Mevalonolactone, 3-Oxohexanoic acid, Adipate semialdehyde None None None 28316.1 29360.2 34995.1 27772.4 31764.4 29573.3 31662.9 47155.5 24256.6 27489.8 28094.1 24355.0 23578.8 28944.5 37009.8 30325.9 57920.5 27753.7 27434.0 31890.6 27324.7 23445.5 27862.4 30551.9 26547.3 22845.0 31514.2 26744.8 22879.6 30296.8 25162.4 26049.0 21942.3 25834.0 25273.0 27505.2 23424.3 22373.3 25249.8 29505.2 21568.9 27343.8 129.0921040_MZ Heptanoic acid Un 1.0 None None None None Heptanoic acid, also called enanthic acid, is an organic compound composed of a seven-carbon chain terminating in a carboxylic acid. It is an oily liquid with an unpleasant, rancid odor. It contributes to the odor of some rancid oils. It is slightly soluble in water, but well soluble in ethanol and ether. C7H14O2 None None None 27662.3 29308.0 22916.1 22488.9 24614.0 28224.2 24061.0 27010.8 19821.9 23685.9 23530.1 19309.6 18038.3 30070.2 25262.6 18306.8 29897.9 20849.4 18515.1 18955.8 23282.1 19866.2 25193.3 31137.6 18703.4 18649.5 23577.3 21367.6 19341.2 28852.4 18774.6 17871.4 18554.8 20997.7 22873.9 22668.4 18237.8 18648.0 20071.4 26337.1 14430.5 20974.8 130.0621759_MZ Creatine Un 1.0 None None None None Creatine is an amino acid that occurs in vertebrate tissues and in urine. In muscle tissue, creatine generally occurs as phosphocreatine. Creatine is excreted as creatinine in the urine. Creatine functions as part of the cell's energy shuttle. The high energy phosphate group of ATP is transferred to creatine to form phosphocreatine in the following reaction: Cr + ATP <-> PCr + ADP. This reaction is reversibly catalyzed by creatine kinase. In the human body creatine is synthesized mainly in the liver by the use of parts from three different amino acids - arginine, glycine, and methionine. 95% of it is later stored in the skeletal muscles, with the rest in the brain, heart, testes. C4H9N3O2, Beta-Guanidinopropionic acid None None None 11315.3 13405.5 12801.0 16598.2 13120.1 14994.1 11904.8 15991.5 12867.4 10693.6 14556.9 16173.9 9555.48 17341.6 14751.8 14106.4 13734.5 9847.62 11680.1 12286.1 18453.4 14680.5 12833.8 13180.9 13236.9 12947.0 12824.6 12667.2 13042.8 34492.4 12464.6 12556.3 13103.1 12317.6 13034.2 11360.1 10711.1 13737.2 7714.76 14082.4 10003.7 11220.4 130.0873871_MZ L-Leucine Un 1.0 None None None None Branched chain amino acids (BCAA) are essential amino acids whose carbon structure is marked by a branch point. These three amino acids are critical to human life and are particularly involved in stress, energy and muscle metabolism. BCAA supplementation as therapy, both oral and intravenous, in human health and disease holds great promise. 'BCAA' denotes valine, isoleucine and leucine which are branched chain essential amino acids. Despite their structural similarities, the branched amino acids have different metabolic routes, with valine going solely to carbohydrates, leucine solely to fats and isoleucine to both. The different metabolism accounts for different requirements for these essential amino acids in humans: 12 mg/kg, 14 mg/kg and 16 mg/kg of valine, leucine and isoleucine respectively. Furthermore, these amino acids have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors. Many types of inborn errors of BCAA metabolism exist, and are marked by various abnormalities. The most common form is the maple syrup urine disease, marked by a characteristic urinary odor. Other abnormalities are associated with a wide range of symptoms, such as mental retardation, ataxia, hypoglycemia, spinal muscle atrophy, rash, vomiting and excessive muscle movement. Most forms of BCAA metabolism errors are corrected by dietary restriction of BCAA and at least one form is correctable by supplementation with 10 mg of biotin daily. BCAA are useful because they are metabolized primarily by muscle. Stress state- e.g surgery, trauma, cirrhosis, infections, fever and starvation--require proportionately more BCAA than other amino acids and probably proportionately more leucine than either valine or isoleucine. BCAA and other amino acids are frequently fed intravenously (TPN) to malnourished surgical patients and in some cases of severe trauma. BCAA, particularly leucine, stimulate protein synthesis, increase reutilization of amino acids in many organs and reduce protein breakdown. Furthermore, leucine can be an important source of calories, and is superior as fuel to the ubiquitous intravenous glucose (dextrose). Leucine also stimulates insulin release, which in turn stimulates protein synthesis and inhibits protein breakdown. These effects are particularly useful in athletic training. BCAA should also replace the use of steroids as commonly used by weightlifters. Huntington's chorea and anorexic disorders both are characterized by low serum BCAA. These diseases, as well as forms of Parkinson's, may respond to BCAA therapy. BCAA, and particularly leucine, are among the amino acids most essential for muscle health. (http://www.dcnutrition.com). C6H13NO2, L-Isoleucine, L-Alloisoleucine, L-Norleucine, Aminocaproic acid, Beta-Leucine None None None 790160.0 646907.0 829313.0 457251.0 799506.0 913585.0 753847.0 650464.0 774561.0 624494.0 592942.0 892637.0 902915.0 721872.0 690216.0 845991.0 527908.0 830479.0 743173.0 847375.0 716705.0 744363.0 755195.0 689501.0 681496.0 700673.0 752202.0 775650.0 958145.0 774001.0 442996.0 559499.0 783684.0 484773.0 936892.0 830319.0 679241.0 777925.0 426576.0 784317.0 707336.0 698678.0 131.0348766_MZ Ethylmalonic acid Un 1.0 None None None None Ethylmalonic acid is identified in the urine of patients with short-chain acyl-coenzyme A dehydrogenase deficiency, which is a fatty acid metabolism disorder. C5H8O4, Glutaric acid, Methylsuccinic acid, Dimethylmalonic acid, 2-Acetolactate, (S)-2-Acetolactate, Monoethyl malonic acid None None None 33914.8 35986.2 44033.7 37320.3 31636.9 35520.4 37408.8 40476.9 28233.3 28279.0 28993.0 29654.5 35374.3 55577.7 37703.4 36465.3 44746.7 31938.0 31693.7 33889.3 39556.5 28372.8 29257.1 32813.4 31269.9 31577.2 35825.2 30698.5 31095.6 31798.2 32399.3 31983.4 27428.0 28173.2 30559.5 35210.3 29777.3 26620.5 25763.2 33287.4 26279.4 36759.7 131.0461975_MZ L-Asparagine Un 1.0 None None None None Asparagine (Asn) is one of the 20 most common natural amino acids on Earth. It has carboxamide as the side chain's functional group. It is considered a non-essential amino acid. Asparagine is not an essential amino acid, which means that it can be synthesized from central metabolic pathway intermediates in humans and is not required in the diet. The precursor to asparagine is oxaloacetate. Oxaloacetate is converted to aspartate using a transaminase enzyme. The enzyme transfers the amino group from glutamate to oxaloacetate producing alpha-ketoglutarate and aspartate. The enzyme asparagine synthetase produces asparagine, AMP, glutamate, and pyrophosphate from aspartate, glutamine, and ATP. In the asparagine synthetase reaction, ATP is used to activate aspartate, forming beta-aspartyl-AMP. glutamine donates an ammonium group which reacts with beta-aspartyl-AMP to form asparagine and free AMP. Since the asparagine side chain can make efficient hydrogen bond interactions with the peptide backbone, asparagines are often found near the beginning and end of alpha-helices, and in turn motifs in beta sheets. Its role can be thought as capping the hydrogen bond interactions which would otherwise need to be satisfied by the polypeptide backbone. glutamines have an extra methylene group, have more conformational entropy and thus are less useful in this regard. Asparagine also provides key sites for N-linked glycosylation, modification of the protein chain with the addition of carbohydrate chains. A reaction between asparagine and reducing sugars or reactive carbonyls produces acrylamide (acrylic amide) in food when heated to sufficient temperature, i.e. baking. These occur primarily in baked goods such as french fries, potato chips, and roasted coffee. Asparagine was first isolated in 1806 from asparagus juice, in which it is abundant--hence its name--becoming the first amino acid to be isolated. The smell observed in the urine of some individuals after their consumption of asparagus is attributed to a byproduct of the metabolic breakdown of asparagine, asparagine-amino-succinic-acid monoamide. (However, some scientists disagree and implicate other substances in the smell, especially methanethiol). (http://en.wikipedia.org/wiki/Asparagine). C4H8N2O3, Glycyl-glycine, N-Carbamoylsarcosine, Ureidopropionic acid None None None 35010.3 36111.0 37932.0 21936.7 33059.1 43163.7 31771.7 34378.0 33784.3 29398.8 30072.0 39995.9 36791.5 43056.7 34276.6 39006.9 28587.1 40503.6 37134.3 35160.9 39065.8 33388.8 36071.9 36727.1 29049.7 32573.4 35560.6 36790.8 37529.2 34764.7 24556.6 29700.7 34876.9 27781.2 45249.4 39657.4 30830.0 31099.3 23729.7 35237.9 28664.7 30743.4 131.0824602_MZ L-Ornithine Un 1.0 None None None None Ornithine is an amino acid produced in the urea cycle by the splitting off of urea from arginine. It is a central part of the urea cycle, which allows for the disposal of excess nitrogen. L-Ornithine is also a precursor of citrulline and arginine. In order for ornithine produced in the cytosol to be converted to citrulline, it must first cross the inner mitochondrial membrane into the mitochondrial matrix where it is carbamylated by ornithine transcarbamylase. This transfer is mediated by the mitochondrial ornithine transporter (SLC25A15; AF112968; ORNT1). Mutations in the mitochondrial ornithine transporter result in hyperammonemia, hyperornithinemia, homocitrullinuria (HHH) syndrome, a disorder of the urea cycle. (PMID 16256388) The pathophysiology of the disease may involve diminished ornithine transport into mitochondria, resulting in ornithine accumulation in the cytoplasm and reduced ability to clear carbamoyl phosphate and ammonia loads. (OMIM 838970). C5H12N2O2 None None None 160675.0 148003.0 120718.0 104238.0 113883.0 158627.0 132471.0 131459.0 117355.0 115473.0 140931.0 124320.0 119602.0 134772.0 120459.0 160827.0 145884.0 114285.0 122212.0 138542.0 142728.0 126071.0 144634.0 132776.0 132182.0 118751.0 153064.0 130935.0 136365.0 167026.0 141300.0 158595.0 111480.0 114153.0 175055.0 122157.0 134686.0 130703.0 103064.0 130317.0 107965.0 124022.0 132.0302377_MZ L-Aspartic acid Un 1.0 None None None None Aspartic acid (Asp, D), also known as aspartate, the name of its anion, is one of the 20 natural proteinogenic amino acids which are the building blocks of proteins. As its name indicates, aspartic acid is the carboxylic acid analog of asparagine. As a neurotransmitter, aspartic acid may provide resistance to fatigue and thus lead to endurance, although the evidence to support this idea is not strong. (http://en.wikipedia.org/wiki/Aspartic_acid) Aspartic acid is a nonessential amino acid which is made from glutamic acid by enzymes using vitamin B6. The amino acid has important roles in the urea cycle and DNA metabolism. Aspartic acid is a major excitatory neurotransmitter, which is sometimes found to be increased in epileptic and stroke patients. It is decreased in depressed patients and in patients with brain atrophy. Aspartic acid supplements are being evaluated. Five grams can raise blood levels. Magnesium and zinc may be natural inhibitors of some of the actions of aspartic acid. Aspartic acid, with the amino acid phenylalanine, is a part of a new natural sweetener, aspartame. This sweetener is an advance in artificial sweeteners, and is probably safe in normal doses to all except phenylketonurics. The jury is still out on the long term effects it has on many brain neurohormones. Aspartic acid may be a significant immunostimulant of the thymus and can protect against some of the damaging effects of radiation. Many claims have been made for the special value of administering aspartic acid in the form of potassium and magnesium salts. Since aspartic acid is relatively nontoxic, studies are now in progress to elucidate its pharmacological and therapeutic roles. (http://www.dcnutrition.com/AminoAcids). C4H7NO4, Iminodiacetate None None None 369228.0 395902.0 394442.0 123105.0 744093.0 238951.0 424974.0 671636.0 316129.0 189234.0 506456.0 439960.0 561320.0 314831.0 823414.0 299881.0 598655.0 177589.0 254422.0 535590.0 432381.0 485490.0 402650.0 440832.0 391437.0 379516.0 320776.0 271988.0 616219.0 282842.0 355285.0 288663.0 248463.0 190707.0 584902.0 187991.0 236650.0 796989.0 301461.0 668422.0 205134.0 291519.0 133.0142794_MZ L-Malic acid Un 1.0 None None None None Malic acid is a tart-tasting organic dicarboxylic acid that plays a role in many sour or tart foods. Apples contain malic acid, which contributes to the sourness of a green apple. Malic acid can make a wine taste tart, although the amount decreases with increasing fruit ripeness. (wikipedia). In its ionized form malic acid is called malate. Malate is an intermediate of the TCA cycle along with fumarate. It can also be formed from pyruvate as one of the anaplerotic reactions. In humans, malic acid is both derived from food sources and synthesized in the body through the citric acid cycle or Krebs cycle which takes place in the mitochondria. Malate's importance to the production of energy in the body during both aerobic and anaerobic conditions is well established. Under aerobic conditions, the oxidation of malate to oxaloacetate provides reducing equivalents to the mitochondria through the malate-aspartate redox shuttle. During anaerobic conditions, where a buildup of excess of reducing equivalents inhibits glycolysis, malic acid's simultaneous reduction to succinate and oxidation to oxaloacetate is capable of removing the accumulating reducing equivalents. This allows malic acid to reverse hypoxia's inhibition of glycolysis and energy production. In studies on rats it has been found that only tissue malate is depleted following exhaustive physical activity. Other key metabolites from the citric acid cycle needed for energy production were found to be unchanged. Because of this, a deficiency of malic acid has been hypothesized to be a major cause of physical exhaustion. Notably, the administration of malic acid to rats has been shown to elevate mitochondrial malate and increase mitochondrial respiration and energy production. C4H6O5 None None None 3711270.0 3057010.0 3689560.0 1174810.0 4350540.0 2431110.0 3647230.0 6224880.0 3657510.0 2501310.0 4185810.0 4476640.0 3287770.0 3009820.0 4356210.0 1977160.0 3587290.0 1172310.0 3041230.0 3095030.0 4112360.0 4729390.0 3662340.0 4001920.0 3213270.0 3572440.0 3901740.0 3564060.0 3358060.0 2607730.0 3168770.0 2632160.0 2506280.0 2660910.0 4203340.0 2800030.0 3079980.0 4889680.0 2563550.0 4453930.0 2241980.0 3006640.0 133.0505218_MZ Deoxyribose Un 1.0 None None None None Deoxyribose is an aldopentose, a monosaccharide containing five carbon atoms, and including an aldehyde functional group. It is derived from the pentose sugar ribose by the replacement of the hydroxyl group at the 2 position with hydrogen, leading to the net loss of an oxygen atom, and has chemical formula C5H10O4. In deoxyribose, the carbon furthest from the attached carbon is stripped of the oxygen atom in what would be a hydroxyl group in ribose. The common base adenine (a purine derivative) coupled to deoxyribose is called deoxyadenosine. The 5-triphosphate derivative of adenosine, commonly called adenosine triphosphate (ATP) is an important energy transport molecule in cells. -- Wikipedia. C5H10O4, 2,3-Dihydroxyvaleric acid, 1-Deoxy-D-xylulose, (R)-glycerol 1-acetate, (R)-2,3-Dihydroxy-isovalerate None None None 106721.0 41803.9 51223.3 17097.3 61699.7 65264.9 46742.5 99903.4 49289.9 59875.1 78591.2 65299.0 37542.7 92543.8 60375.3 28355.7 45824.4 19290.7 38888.4 40134.0 74538.4 65788.0 65946.0 63878.9 40831.3 51879.1 50956.1 47482.3 46824.5 130216.0 40432.2 37073.5 32451.2 36170.8 64945.4 36636.0 41130.9 72131.8 34395.4 60529.6 26120.4 36402.1 134.0472728_MZ Adenine Un 1.0 None None None None Adenine is a purine base. Adenine is found in both DNA and RNA. Adenine is a fundamental component of adenine nucleotides. Adenine forms adenosine, a nucleoside, when attached to ribose, and deoxyadenosine when attached to deoxyribose; it forms adenosine triphosphate (ATP), a nucleotide, when three phosphate groups are added to adenosine. Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring chemical energy between chemical reactions. Purine inborn errors of metabolism (IEM) are serious hereditary disorders, which should be suspected in any case of neonatal fitting, failure to thrive, recurrent infections, neurological deficit, renal disease, self-mutilation and other manifestations. Investigation usually starts with uric acid (UA) determination in urine and plasma. (OMIM 300322, 229600, 603027, 232400, 232600, 232800, 201450, 220150, 232200, 162000, 164050, 278300). (PMID: 17052198, 17520339). C5H5N5 None None None 1245000.0 1356590.0 1375980.0 1566880.0 1515120.0 1316610.0 1609040.0 1191360.0 1622920.0 1333470.0 1350710.0 1549820.0 1328610.0 1292660.0 1750200.0 1473710.0 1558550.0 1692070.0 1485010.0 1382550.0 1333200.0 1597640.0 1423000.0 1379260.0 1463470.0 1517950.0 1749640.0 1658390.0 1850260.0 1511640.0 1350740.0 1452710.0 1420460.0 1321480.0 2466750.0 1308070.0 1715990.0 1616530.0 2043180.0 1407770.0 1432550.0 1363870.0 135.0300982_MZ Erythronic acid Un 1.0 None None None None Erythronic acid is a sugar component of aqueous humour (eye). It may be derived from glycated proteins or from degradation of ascorbic acid. Erythronic acid is a normal organic acid present in a healthy adult and pediatric population. It has been found in urine, plasma, CSF and synovial fluid. (PMID: 14708889, 8087979, 8376520, 10420182). Erythronic acid is formed when N-Acetyl-D-glucosamine (GlcNAc) is oxidised. GlcNAc is a constituent of hyaluronic acid (HA), a polysaccharide consisting of alternating units of Glucuronic acid and GlcNAc, present as an aqueous solution in synovial fluid. In synovial fluid of patients suffering from rheumatoid arthritis, HA is thought to be degraded either by radicals generated by Fenton chemistry (Fe2+/H2O2) or by NaOCl generated by myeloperoxidase. (PMID: 10614067). C4H8O5, Threonic acid None None None 342639.0 423877.0 399439.0 414516.0 311050.0 440165.0 307032.0 367770.0 757594.0 534741.0 449669.0 849143.0 242100.0 502949.0 480067.0 266334.0 335002.0 445742.0 369005.0 247718.0 421036.0 705073.0 367014.0 436157.0 313010.0 571718.0 358143.0 517735.0 448051.0 624139.0 260312.0 355155.0 581513.0 339948.0 827948.0 544924.0 536428.0 608828.0 333488.0 465955.0 264152.0 360868.0 135.0451688_MZ Phenylacetic acid Un 1.0 None None None None Phenyl acetate (or phenylacetate) is a carboxylic acid ester that has been found in the biofluids of patients with nephritis and/or hepatitis as well as patients with phenylketonuria (PKU). Excess phenylalanine in the body can be disposed of through a transamination process leading to the production of phenylpyruvate. The phenylpyruvate can be further metabolized into a number of products. Decarboxylation of phenylpyruvate gives phenylacetate, while a reduction reaction gives phenyllactate. The phenylacetate can be further conjugated with glutamine to give phenylacetyl glutamine. All of these metabolites can be detected in serum and urine of PKU patients. Phenyl acetate is also produced endogenously as the metabolite of 2-Phenylethylamine, which is mainly metabolized by monoamine oxidase to form phenyl acetate. 2-phenylethylamine is an endogenous amphetamine which may modulate central adrenergic functions, and the urinary phenyl acetate levels have been postulated as a marker for depression. (PMID: 17978765, 476920, 6857245). Phenylacetate is also found in essential oils, e.g. neroli, rose oil, free and as esters' and in many fruits. As a result it is used as a perfumery and flavoring ingredient. C8H8O2, 4-Hydroxyphenylacetaldehyde None None None 309903.0 315530.0 251379.0 257994.0 265060.0 340853.0 330608.0 314902.0 296832.0 299019.0 246117.0 277494.0 257463.0 322912.0 290290.0 233881.0 362732.0 295142.0 309226.0 305538.0 290671.0 273823.0 289718.0 363795.0 242381.0 244414.0 270736.0 294511.0 246654.0 350873.0 244591.0 235929.0 235336.0 280420.0 308983.0 278348.0 269166.0 230637.0 268487.0 299761.0 254622.0 273453.0 136.0412797_MZ Trigonelline Un 1.0 None None None None Trigonelline is an alkaloid with chemical formula C7H7NO2 and CAS number 535-83-1. Trigonelline is a product of the metabolism of niacin (vitamin B3) which is excreted in the urine. It is also found in coffee, where it may help to prevent dental caries by preventing the bacteria Streptococcus mutans from adhering to teeth. Trigonelline occurs in many other plants, including fenugreek seeds, garden peas, hemp seed, oats and potatoes. C7H7NO2, 3-Pyridylacetic acid, 2-Aminobenzoic acid, p-Aminobenzoic acid None None None 17432.2 16632.0 16088.6 12140.7 14595.8 16968.3 19106.8 15962.9 15108.7 16177.0 14053.1 16767.8 17237.1 14572.2 14774.0 18732.3 15383.8 20858.4 14776.1 19214.8 17490.8 12806.6 14295.7 15323.8 15694.4 13601.6 16565.9 15669.3 13050.4 16219.8 17657.5 15108.1 12787.9 13627.3 15008.0 14583.0 14466.5 13881.0 11531.5 14613.9 18245.4 16197.7 136.0766207_MZ Tyramine Un 1.0 None None None None m-Tyramine is an amine derived from Tyrosine, Phenylethylamine and other catecholamines. (PMID 7335956). C8H11NO, 2-Hydroxyphenethylamine, Dimethylaniline-N-oxide None None None 3769.2 3170.62 3500.35 3158.57 3371.63 3407.48 3146.91 3484.56 3402.06 3176.78 2958.67 3055.7 3079.52 3391.05 3273.53 3098.25 3333.33 2848.93 3001.29 3407.34 3299.12 3035.71 3300.17 3256.53 3131.85 3044.38 3347.97 3404.42 3412.57 3664.67 2910.92 2811.84 2953.52 3396.76 3369.98 3015.67 3140.68 3297.78 3379.09 3325.02 2728.77 2882.36 137.0357944_MZ Urocanic acid Un 1.0 None None None None Urocanic acid is a breakdown (deamination) product of histidine. In the liver, urocanic acid is an intermediate in the conversion of histidine to glutamic acid, whereas in the epidermis, it accumulates and may be both a UV protectant and an immunoregulator. Urocanic acid (UA) exists as a trans isomer (t-UA, approximately 30 mg/cm2) in the uppermost layer of the skin (stratum corneum). t-UA is formed as the cells of the second layer of skin become metabolically inactive. During this process, proteins and membranes degrade, histidine is released, and histidase (histidine ammonia lyase) catalyzes the deamination of histidine to form t-UA. t-UA accumulates in the epidermis until removal by either the monthly skin renewal cycle or sweat. Upon absorption of UV light, the naturally occurring t-UA isomerizes to its cis form, c-UA. Because DNA lesions (e.g., pyrimidine dimers) in the lower epidermis can result from UV-B absorption, initial research proposed that t-UA acted as a natural sunscreen absorbing UV-B in the stratum corneum before the damaging rays could penetrate into lower epidermal zones. Researchers have found that c-UA also suppresses contact hypersensitivity and delayed hypersensitivity, reduces the Langerhans cell count in the epidermis, prolongs skin-graft survival time, and affects natural killer cell activity. C6H6N2O2, Nicotinamide N-oxide None None None 195271.0 197099.0 193786.0 189997.0 181774.0 210126.0 197521.0 233995.0 197084.0 202197.0 201942.0 190939.0 192908.0 190399.0 187446.0 185601.0 197875.0 201301.0 195310.0 189647.0 196215.0 474416.0 202936.0 214281.0 186883.0 197182.0 186625.0 200676.0 196988.0 198335.0 186852.0 182669.0 195450.0 241253.0 206528.0 195427.0 195983.0 196200.0 202417.0 194395.0 191416.0 197627.0 137.0599096_MZ Tyrosol Un 1.0 None None None None Tyrosol is a phenolic compound present in two of the traditional components of the Mediterranean diet: wine and virgin olive oil. The presence of tyrosol has been described in red and white wines. Tyrosol is also present in vermouth and beer. Tyrosol has been shown to be able to exert antioxidant activity in vitro studies. Oxidation of low-density lipoprotein (LDL) appears to occur predominantly in arterial intimae in microdomains sequestered from antioxidants of plasma. The antioxidant content of the LDL particle is critical for its protection. The ability of tyrosol to bind human LDL has been reported. The bioavailability of tyrosol in humans from virgin olive oil in its natural form has been demonstrated. Urinary tyrosol increases, reaching a peak at 0-4 h after virgin olive oil administration. Men and women show a different pattern of urinary excretion of tyrosol. Moreover, tyrosol is absorbed in a dose-dependent manner after sustained and moderate doses of virgin olive oil. Tyrosol from wine or virgin olive oil could exert beneficial effects on human health in vivo if its biological properties are confirmed. (PMID 15134375). C8H10O2 None None None 31297.2 37323.8 39443.2 37704.6 44792.6 37841.3 35695.3 40755.6 36822.8 37892.8 44109.8 42304.2 28488.9 37295.6 41533.7 35503.3 40139.1 31190.9 32560.7 32815.5 32835.3 47480.3 36533.3 34918.9 34330.9 37152.9 37453.5 36602.6 36868.6 37709.1 30746.3 30528.3 40386.3 35818.4 36656.8 32250.8 34456.2 40810.9 33829.2 37256.1 27053.4 31956.6 137.0710963_MZ L-2,4-diaminobutyric acid Un 1.0 None None None None L-3-Amino-isobutanoic acid is a component of branched-chain amino acid biosynthesis and metabolism. It can also be used in pyrimidine metabolism. L-3-Amino-isobutanoic acid is produced from S-methylmalonate semialdehyde by the enzyme 4-aminobutyrate aminotransferase. C4H10N2O2, 2,4-Diaminobutyric acid None None None 8725.19 8866.87 9054.31 8348.33 9320.92 9338.97 8700.59 9646.45 8286.77 9010.77 9332.39 9008.12 7562.62 8524.11 8721.72 9309.28 9328.34 9040.45 8050.69 8308.14 8944.37 9817.95 8664.9 8884.96 8406.68 8804.83 8835.29 8348.88 8462.66 9001.72 8153.95 7965.57 8546.23 9127.7 8820.21 8421.94 8008.34 8679.06 8448.81 8296.87 7602.72 7993.7 138.0200779_MZ 3-Hydroxypicolinic acid Un 1.0 None None None None 3-Hydroxy picolinic acid is a picolinic acid derivative and is a member of the pyridine family. Picolinic acid is an isomer of nicotinic acid, which has the carboxyl side chain at the 3-position. It is a catabolite of the amino acid tryptophan. C6H5NO3, 4-Nitrophenol, 6-Hydroxynicotinic acid None None None 32430.2 26917.3 21643.9 29789.4 23731.9 26599.2 27022.6 29013.5 23086.3 27177.0 27411.4 17501.6 21020.5 29408.4 24564.0 20850.3 30133.3 29008.9 29815.5 28586.1 26693.5 18259.5 25721.1 31016.8 24925.4 18628.0 23803.2 24301.0 18119.5 32877.7 24881.3 23133.6 18051.5 26723.0 18150.5 30593.0 21624.6 16703.6 22443.5 27834.4 27052.3 27343.8 138.0558958_MZ 3,4-Dihydroxybenzylamine Un 1.0 None None None None 3,4-Dihydroxybenzylamine is an alternative substrates for dopamine that is a member of the catecholamine family in the brain, and is a precursor to epinephrine and norepinephrine. Catecholamines contain a catechol group, and are derived from the amino acid and tyrosine. They are produced mainly by the chromaffin cells of the adrenal medulla and the postganglionic fibers of the sympathetic nervous system. Catecholamine synthesis is inhibited by alpha-Methyltyrosine, by inhibiting tyrosine-3 monooxygenase.Wikipedia. C7H9NO2 None None None 16221.7 16329.7 18828.8 14167.9 15925.6 17126.0 22868.7 16216.5 18973.8 18165.6 15324.0 21496.3 14299.0 16404.5 18594.2 15338.9 19386.6 12062.8 13079.5 21901.9 16085.0 16933.2 14503.1 11788.8 15416.2 16221.5 17293.4 16328.8 12981.7 16563.8 18434.3 14624.3 14836.1 16999.6 17440.7 12875.6 14555.3 17622.2 10818.0 14563.9 16919.0 12395.2 138.0668098_MZ Histidinal Un 1.0 None None None None Histidinal is involved in the histidine biosynthesis I pathway. Histidinal is produced by the reaction between histidinol and NAD+, with NADH as a byproduct. The reaction is catalyzed by histidinol dehydrogenase. Histidinal reacts with NAD+ and H2O to produce L-histidine and NADH. Histidinol dehydrogenase catalyzes this reaction. C6H9N3O None None None 3236.81 3564.01 3975.44 3208.92 3836.58 3925.24 4252.61 3674.07 3686.28 3770.34 3872.64 4483.25 2826.38 3461.08 4071.24 3309.6 4094.91 2692.59 2852.64 3706.74 3259.72 3625.58 3210.33 2954.2 3248.79 3340.7 3769.85 3515.15 3015.0 3509.09 3283.02 2915.81 3352.07 3403.65 3599.25 2782.53 3086.59 3717.13 2703.06 3390.15 3089.97 2603.97 138.9792165_MZ Acetylphosphate Un 1.0 None None None None Acetylphosphate or actyl phosphate is a compound involved in taurine and hypotaurine metabolism as well as pyruvate metabolism. It is generated from sulfoacetaldehyde, converted to acetyl-CoA and acetate via phosphate acetyltransferase (EC:2.3.1.8) and acetate kinase (EC:2.7.2.1) respectively. It is also an intermediate in pyruvate metabolism. It is generated from pyruvate and the formation is catalyzed by pyruvate oxidase (EC:1.2.3.3). C2H5O5P, Phosphonoacetate None None None 37120.9 34985.9 38646.8 35608.5 35947.7 35948.4 38548.5 38022.1 39964.6 40265.1 38859.4 35935.8 42916.2 37894.3 43092.5 35780.1 39229.9 45236.7 41799.0 38489.0 38121.9 39150.1 39232.3 39536.8 40869.9 38848.6 41512.0 38103.5 38450.9 40594.2 35988.7 40007.9 36585.0 37706.2 43073.6 41219.7 39560.2 39957.8 43905.1 40384.6 42912.1 40602.8 139.9759985_MZ Carbamoylphosphate Un 1.0 None None None None Carbamoyl phosphate is a precursor of both arginine and pyrimidine biosynthesis. It is a labile and potentially toxic intermediate. Carbamoyl phosphate is a molecule that is involved in ridding the body of excess nitrogen in the urea cycle, and also in the synthesis of pyrimidines. It is produced from carbon dioxide, ammonia, and phosphate (from ATP) by the enzyme carbamoyl phosphate synthase. -- Wikipedia. CH4NO5P None None None 5128.7 5102.9 4634.08 5565.02 4885.46 5096.59 4903.08 5365.44 5137.25 5614.09 5168.64 4956.81 5544.28 5282.83 4873.67 4990.42 5779.52 5487.48 5223.83 5119.72 4812.98 5043.51 5149.71 5012.46 5311.12 5099.31 4956.0 5045.98 4977.68 5056.35 4822.83 5513.53 5106.48 5218.82 5025.89 5168.65 5368.41 5136.8 6248.79 5077.1 5118.64 4918.5 140.0118208_MZ O-Phosphoethanolamine Un 1.0 None None None None Phosphoethanolamine (PE) is a phosphomonoester metabolite of the phospholipid metabolism. PE is a precursor of phospholipid synthesis and a product of phospholipid breakdown. Phosphomonoesters are present at much higher levels in brain than in other organs. In developing brain, phosphomonoesters are normally elevated during the period of neuritic proliferation. This also coincides with the occurrence of normal programmed cell death and synaptic pruning in developing brain. These findings are consistent with the role of phosphomonoesters in membrane biosynthesis. PE shows a strong structural similarity to the inhibitory neurotransmitter, GABA, and the GABAB receptor partial agonist, 3-amino-propylphosphonic acid. PE is a phosphomonoester which is decreased in post-mortem Alzheimer's disease (AD) brain. (PMID: 7791524, 8588821, 11566853). C2H8NO4P None None None 60158.3 70886.8 64914.3 64351.1 62429.8 62196.1 62827.5 74226.4 63489.6 65947.6 61129.8 79361.9 64276.2 103525.0 73460.4 49044.4 67132.4 58345.5 57724.4 55985.3 84584.8 69399.9 69144.3 63964.3 55463.4 55003.1 67874.4 56484.4 60317.2 61353.6 49852.5 50652.9 69063.1 65914.5 77098.6 53103.1 62752.4 73442.6 47405.1 81248.2 41696.1 60798.1 140.0828828_MZ L-Histidinol Un 1.0 None None None None L-Histidinol, a structural analogue of the essential amino acid L-histidine, enhances the toxicity of a variety of anticancer drugs for many tumor cells of animal origin. (PMID 8297120). L-histidinol inhibits human Myristoyl- CoA:protein-myristoyltransferase (hNMT) (an essential eukaryotic enzyme that catalyzes the cotranslational transfer of myristate to the NH2-terminal glycine residue of a number of important proteins of diverse function). (PMID 9778369). C6H11N3O None None None 1470.12 1635.65 5494.49 1976.55 1866.12 1630.62 1625.98 2133.18 1893.57 1735.96 1935.22 1927.94 1357.82 1778.62 1823.36 1364.37 1944.48 1559.11 1489.39 1673.91 1517.86 3136.2 1555.19 1643.81 1575.16 4304.83 1789.91 3867.15 4408.91 2037.21 1706.85 1265.84 1597.72 1738.06 6468.33 1703.69 1478.42 1638.48 1655.08 1749.06 1448.48 1367.85 141.0196635_MZ cis-cis-Muconic acid Un 1.0 None None None None C6H6O4, Sumiki's acid, trans-trans-Muconic acid None None None 239664.0 236347.0 235405.0 231638.0 229426.0 231119.0 228254.0 240350.0 241450.0 245462.0 241302.0 234943.0 242384.0 238643.0 235405.0 211507.0 235785.0 249642.0 243623.0 239974.0 236114.0 247045.0 241835.0 242714.0 235359.0 238477.0 238000.0 239818.0 246892.0 240874.0 215837.0 210480.0 247514.0 249021.0 237144.0 237609.0 250305.0 241496.0 265490.0 243808.0 227193.0 241981.0 141.0296281_MZ 5-Hydroxymethyluracil Un 1.0 None None None None C5H6N2O3 None None None 70840.5 71769.8 71040.7 69812.7 69402.0 66864.1 67406.0 72440.0 71990.0 73575.0 69808.7 71732.1 63889.6 69682.9 68654.0 66727.4 65614.6 80590.2 71120.9 69814.2 70294.5 67938.0 67919.9 70879.7 68095.8 72002.8 67071.1 72915.8 73710.7 71981.3 66086.1 63840.4 72805.5 77061.2 70930.2 72805.5 72072.0 72618.1 79691.5 68397.4 64188.5 69399.1 141.0553976_MZ D-Threitol Un 1.0 None None None None D-Threitol can be regarded as the main end product of D-xylose metabolism in man. Threitol is a C4-polyol (tetritol); the total C4-polyol concentration of threitol decreases with age. Several inborn errors of metabolism with abnormal polyol concentrations in body fluids are known to date (such as pentosuria and galactosemia). Most of these defects can be diagnosed by the assessment of urinary concentrations of polyols. Several studies have revealed that urinary levels of some polyols may vary in diseases associated with carbohydrate metabolism derangements such as diabetes mellitus and uremia. The abnormal occurrence of various polyols in diseases with a specific enzyme deficiency such as pentosuria4 and galactosemias has also been reported. (PMID: 908147, 16435188, 14988808, Analytical Sciences (1990), 6(5), 657-66.). C4H10O4, Erythritol None None None 8149.96 9467.9 9933.22 9614.42 11229.0 9682.13 9505.57 10304.8 8797.47 9711.44 10489.8 10295.0 7333.88 9451.19 11076.3 9405.53 11278.1 7334.61 7814.29 8250.09 8398.26 9551.41 8970.75 9015.07 8708.39 9037.29 9955.78 9237.7 8529.6 9766.14 7350.62 8149.35 9299.22 8307.69 8800.42 8463.87 8183.22 9826.41 7749.98 9862.67 6172.45 7887.71 141.0918344_MZ 2-Octenoic acid Un 1.0 None None None None 2-Octenoic acid is a normal organic acid produced by hepatic microsomal oxidation of aliphatic aldehydes and is a metabolite naturally found in the urine and plasma. (PMID 1883862, 8087979, 4086594, 1417834, 6480773). C8H14O2, trans-2-Octenoic acid None None None 20979.2 27417.1 26130.7 26449.5 33186.9 31790.8 23550.8 21862.2 23379.3 25108.1 32646.8 26596.6 12847.7 29754.3 30388.3 22149.8 23424.6 12380.1 18471.6 17627.0 23678.7 22498.7 27011.1 24726.3 21560.9 22198.4 29229.5 21273.2 20953.6 28125.6 17448.6 20031.9 25874.2 19544.3 24418.0 20657.9 20324.7 25950.6 14847.5 26932.2 12495.7 17818.9 142.0508508_MZ Vinylacetylglycine Un 1.0 None None None None Vinylacetylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction:. acyl-CoA + glycine < -- > CoA + N-acylglycine. Vinylacetylglycine is a human metabolite that had been identified in a GC/MS urine screen. Increased amounts of this metabolite in the urine has been linked to a metabolomic disorder termed Isovaleric acidemia. (Gas-Chromatographic Method of Analysis for Urinary Organic Acids. I. Retention indices of 155 metaboically Important Compounds; Kay Tanaka, David G. Hine, Agnes West-Dull, and Theodore B. Lynn.). C6H9NO3 None None None 18694.8 10168.2 11830.7 21584.2 11519.5 13307.1 12496.6 13101.6 10868.3 9470.39 11852.3 17598.8 7690.87 10316.7 9896.3 15797.8 11095.4 11171.3 11895.4 11071.7 9573.28 13755.1 15836.7 9828.39 10693.5 10284.4 8919.2 14339.4 12318.7 13896.5 11553.3 11780.8 9223.62 10733.1 10817.8 11993.6 12326.0 11802.0 7786.01 12341.5 10070.7 9478.73 143.0349331_MZ 3-Hexenedioic acid Un 1.0 None None None None 3-Hexenedioic acid is a normal human unsaturated dicarboxylic acid metabolite with increased excretion in patients with Dicarboxylic aciduria caused by fatty acid metabolism disorders. (PMID 2614263, 7096501) The urinary excretion of 3-Hexenedioic acid is increased in conditions of augmented mobilization of fatty acids or inhibited fatty acid oxidation. (PMID 2001377). C6H8O4, 3-Methylglutaconic acid, (E)-2-Methylglutaconic acid, trans-2-Hexenedioic acid None None None 68275.3 59932.1 74798.0 46813.1 63101.2 91812.9 67967.8 51724.5 70893.5 82188.7 67209.3 73308.2 71657.3 57680.6 77887.1 70113.9 49008.7 93487.8 84171.5 76900.2 66333.5 76187.5 71460.6 67417.1 64355.4 62362.3 67630.9 75564.7 79505.5 81332.3 48631.3 58613.7 71070.9 61816.2 76463.7 88676.1 66048.5 71752.7 47735.5 82799.7 62195.4 66700.0 143.0712224_MZ 4-Hydroxycyclohexylcarboxylic acid Un 1.0 None None None None 4-Hydroxycyclohexylcarboxylic acid is a rare compound in urinary organic acid analysis. C7H12O3 None None None 18856.4 18924.1 32565.7 20527.9 24222.5 19499.1 29768.2 43321.2 15035.8 17405.9 18817.4 14238.3 21207.7 18432.5 32289.0 25857.3 61327.4 18449.8 17925.4 27029.4 17505.0 13886.7 17190.1 19140.7 20467.0 14011.2 25868.5 19412.0 13471.2 20566.7 18766.4 18732.1 14271.5 16033.8 15341.9 19217.3 14480.4 14654.5 18936.0 21449.0 13380.7 20688.2 143.1076499_MZ Caprylic acid Un 1.0 None None None None Caprylic acid is the common name for the eight-carbon straight chain fatty acid known by the systematic name octanoic acid. It is found naturally in coconuts and breast milk. It is an oily liquid with a slightly unpleasant rancid taste that is minimally soluble in water. Caprylic acid is used commercially in the production of esters used in perfumery and also in the manufacture of dyes. (wikipedia). C8H16O2, Valproic acid None None None 40470.3 42507.5 39240.5 43136.4 37511.0 41285.3 39813.4 44524.8 36110.3 39844.6 39074.9 33804.0 32015.0 40958.4 38876.1 32149.3 46069.4 48679.3 37205.9 37593.2 39407.1 34808.2 39125.6 49560.8 34628.5 37133.9 36815.3 40688.5 35482.8 43128.3 35874.8 31268.5 34024.1 39241.1 41195.7 44148.0 33847.3 32980.8 40868.0 41834.2 32782.1 42335.0 144.0301812_MZ 2-Keto-glutaramic acid Un 1.0 None None None None deaminated metabolite of glutamine in csf of patients with hepatic coma; intermediate in the detoxification of ammonia in brain; structure. C5H7NO4 None None None 5545.44 4898.67 5017.38 4289.56 5481.82 5383.5 4984.31 4999.48 4977.54 4547.14 5052.32 4234.32 4659.52 4900.66 4443.71 4999.88 4758.81 4625.3 3939.73 4788.27 5067.35 4201.57 5080.55 4561.1 4681.43 4830.97 4841.87 5038.17 5071.92 5469.45 5154.16 5167.38 4218.78 3985.19 4554.24 4446.54 3889.1 4432.61 3778.3 4474.57 4642.45 4209.59 144.0568800_MZ 5-Methylcytosine Un 1.0 None None None None 5-Methylcytosine is a methylated nucleotide base found in eukaryotic DNA. In animals, the DNA methylation of cytosine to form 5-methylcytosine is found primarily in the palindromic sequence CpG. In plants, the methylated sequence is CpNpGp, where N can be any base. -- Pubchem; 5-Methylcytosine is a methylated form of cytosine in which a methyl group is attached to carbon 5, altering its structure without altering its base-pairing properties. -- Wikipedia; 5-Methylcytosine is an epigenetic modification formed by the action of DNA methyltransferases. In bacteria, 5-methylcytosine can be found at a variety of sites, and is often used as a marker to protect DNA from being cut by native methylation-sensitive restriction enzymes. In plants, 5-methylcytosine occurs at both CpG and CpNpG sequences. In fungi and animals, 5-methylcytosine predominately occurs at CpG dinucleotides. Although most eukaryotes methylate only a small percentage of these sites, in vertebrates 70-80% of CpG cytosines are methylated. -- Wikipedia. C5H7N3O, 2-O-Methylcytosine None None None 6166.98 5544.19 6299.81 7918.89 4282.27 4947.01 6502.32 7495.36 4383.56 5465.72 6051.91 4998.21 4360.25 5061.82 5571.8 5373.84 5956.73 4891.79 3693.6 4641.14 4149.93 3794.85 4531.76 4595.27 4444.28 6646.62 4334.9 4620.2 4606.54 5227.89 5476.93 4450.75 3980.51 4624.66 3822.17 4408.97 4310.83 4131.06 3530.68 5229.15 4921.36 4777.37 144.0666377_MZ Allysine Un 1.0 None None None None Allysine is a derivative of Lysine, used in the production of elastin and collagen. It is produced by the actions of the enzyme lysyl oxidase in the extracellular matrix and is essential in the crosslink formation that stabilizes collagen and elastin. C6H11NO3, 4-Acetamidobutanoic acid, 2-Keto-6-aminocaproate, (S)-5-Amino-3-oxohexanoate None None None 72604.6 54927.6 62033.7 122633.0 78685.3 61823.8 69297.1 46463.0 65831.6 70142.0 59576.8 63880.4 51125.7 70320.3 67277.8 77153.3 82212.4 87866.4 56390.1 35840.9 61145.5 38784.5 72450.5 47727.6 71412.1 39515.8 51883.8 63355.5 63892.5 58141.9 100826.0 81241.9 41455.2 43458.6 62697.2 59087.5 54257.6 60251.6 36318.5 58572.2 64233.5 51768.6 144.1029393_MZ 3-Dehydroxycarnitine Un 1.0 None None None None 3-Dehydroxycarnitine is an acylcarnitine. Numerous disorders have been described that lead to disturbances in energy production and in intermediary metabolism in the organism which are characterized by the production and excretion of unusual acylcarnitines. A mutation in the gene coding for carnitine-acylcarnitine translocase or the OCTN2 transporter aetiologically causes a carnitine deficiency that results in poor intestinal absorption of dietary L-carnitine, its impaired reabsorption by the kidney and, consequently, in increased urinary loss of L-carnitine. Determination of the qualitative pattern of acylcarnitines can be of diagnostic and therapeutic importance. The betaine structure of carnitine requires special analytical procedures for recording. The ionic nature of L-carnitine causes a high water solubility which decreases with increasing chain length of the ester group in the acylcarnitines. Therefore, the distribution of L-carnitine and acylcarnitines in various organs is defined by their function and their physico-chemical properties as well. High performance liquid chromatography (HPLC) permits screening for free and total carnitine, as well as complete quantitative acylcarnitine determination, including the long-chain acylcarnitine profile. (PMID: 17508264, Monatshefte fuer Chemie (2005), 136(8), 1279-1291., Int J Mass Spectrom. 1999;188:39-52.). C7H15NO2 None None None 4349.46 3150.22 3450.35 5716.46 10044.3 4611.63 2558.69 8390.18 5232.52 3377.59 9698.97 10344.9 4307.76 9272.38 4308.21 2966.11 10324.7 6983.61 4859.23 3706.8 4685.15 5386.86 3234.14 12696.1 2873.03 13824.5 7675.65 9766.77 7108.55 6809.91 3368.34 4060.99 3055.24 3398.9 10993.4 6885.43 4854.89 10063.0 2588.21 10079.2 4981.17 2524.95 145.0141831_MZ Oxoglutaric acid Un 1.0 None None None None Alpha-ketoglutaric acid is an important biological compound and is a key intermediate in the Krebs cycle. Alpha-ketoglutaric acid occurs naturally within cells. One of its functions is to combine with ammonia to form glutamic acid and then glutamine. Another function is to combine with nitrogen released in the cell, therefore preventing nitrogen overload. (wikipedia). C5H6O5 None None None 21809.4 53904.8 48181.8 89735.7 40889.5 39107.9 49229.9 40575.2 53318.2 57452.1 45176.7 102652.0 24010.4 42085.0 52387.7 41101.6 55556.7 20475.3 31405.8 37530.2 37892.5 70984.9 36644.9 38993.7 40732.5 84600.1 55106.7 33308.9 51669.5 32466.2 55635.6 50767.1 100982.0 37744.7 65898.3 41333.7 47072.4 79142.6 34429.4 44925.5 37806.7 30022.8 145.0504303_MZ Adipic acid Un 1.0 None None None None Adipic acid is an important inudstrial dicarboxylic acid with about 2.5 billion kilograms produced per year. It is used mainly in the production of nylon. It occurs relatively rarely in nature. It has a tart taste and is also used as an additive and gelling agent in jello or gelatins. It is also used in some calcium carbonate antacids to make them tart. Adipic acid has also been incorporated into controlled-release formulation matrix tablets to obtain pH-independent release for both weakly basic and weakly acidic drugs. Adipic acid in the urine and in the blood is typically exogenous in origin and is a good biomarker of jello consumption. In fact, a condition known as adipic aciduria is actually an artifact of jello consumption (PMID: 1779643). However, certain disorders (such as diabetes and glutaric aciduria type I.) can lead to elevated levels of adipic acid snd other dicarboxcylic acids (such as suberic acid) in urine (PMID: 17520433; PMID: 6778884). C6H10O4, 2-Methylglutaric acid, Methylglutaric acid, Monomethyl glutaric acid, 2,2-Dimethylsuccinic acid, Solerol, (S)-2-Aceto-2-hydroxybutanoic acid None None None 55398.3 43018.4 45075.7 61629.7 34756.3 44257.2 37521.5 70762.6 40180.7 44088.9 46772.3 42063.8 27822.6 42314.8 41111.6 50800.8 42940.2 36651.8 35265.3 34432.5 41922.2 35326.7 40870.9 37579.2 40916.5 40748.9 43806.3 48132.1 30092.4 55928.4 56073.9 50657.4 37508.8 42181.2 38919.6 44872.6 40133.6 32858.6 27148.1 43545.4 39112.5 43595.9 145.0619989_MZ L-Glutamine Un 1.0 None None None None Glutamine (Gln) is one of the 20 amino acids encoded by the standard genetic code. Its side chain is an amide; it is formed by replacing a side-chain hydroxyl of glutamic acid with an amine functional group. glutamine is found in foods high in proteins, such as fish, red meat, beans, and dairy products. glutamine is a supplement that is used in weightlifting, bodybuilding, endurance and other sports, as well as by those who suffer from muscular cramps or pain particularly elderly people. The main use of glutamine within the diet of either group is as a means of replenishing the body's stores of amino acids that have been used during exercise or everyday activities. Studies which are looking into problems with excessive consumption of glutamine thus far have proved inconclusive. However, normal supplementation is healthy mainly because glutamine is supposed to be supplemented after prolonged periods of exercise (for example, a workout or exercise in which amino acids are required for use) and replenishes amino acid stores; this being the main reason glutamine is recommended during fasting or for people who suffer from physical trauma, immune deficiencies, or cancer. There is a significant body of evidence that links glutamine-enriched diets with intestinal effects; aiding maintenance of gut barrier function, intestinal cell proliferation and differentiation, as well as generally reducing septic morbidity and the symptoms of Irritable Bowel Syndrome. The reason for such cleansing properties is thought to stem from the fact that the intestinal extraction rate of glutamine is higher than that for other amino acids, and is therefore thought to be the most viable option when attempting to alleviate conditions relating to the gastrointestinal tract. These conditions were discovered after comparing plasma concentration within the gut between glutamine-enriched and non glutamine-enriched diets. However, even though glutamine is thought to have cleansing properties and effects, it is unknown to what extent glutamine has clinical benefits, due to the varied concentrations of glutamine in varieties of food. It is also known that glutamine has various effects in reducing healing time after operations. Hospital waiting times after abdominal surgery are reduced by providing parenteral nutrition regimens containing amounts of glutamine to patients. Clinical trials have revealed that patients on supplementation regimes containing glutamine have improved nitrogen balances, generation of cysteinyl-leukotrienes from polymorphonuclear neutrophil granulocytes and improved lymphocyte recovery and intestinal permeability (in postoperative patients) - in comparison to those who had no glutamine within their dietary regime; all without any side-effects. (http://en.wikipedia.org/wiki/glutamine). C5H10N2O3, Ureidoisobutyric acid, Alanylglycine None None None 2794680.0 2597640.0 2479770.0 2212360.0 2204760.0 2457400.0 1870380.0 2853480.0 1977610.0 1927960.0 2845360.0 2941010.0 2403490.0 2349580.0 2291430.0 2881670.0 1740070.0 2307800.0 2807780.0 2199840.0 3005980.0 2599010.0 1822110.0 2641430.0 1724270.0 2828100.0 2168180.0 2315360.0 2327020.0 2174760.0 1919840.0 2391310.0 2457220.0 1890910.0 3063520.0 3401580.0 2006210.0 1996810.0 1836530.0 2246020.0 2479480.0 2874160.0 145.0981660_MZ L-Lysine Un 1.0 None None None None L-lysine is an essential amino acid. Normal requirements for lysine have been found to be about 8 g per day or 12 mg/kg in adults. Children and infants need more- 44 mg/kg per day for an eleven to-twelve-year old, and 97 mg/kg per day for three-to six-month old. Lysine is highly concentrated in muscle compared to most other amino acids. Lysine is high in foods such as wheat germ, cottage cheese and chicken. Of meat products, wild game and pork have the highest concentration of lysine. Fruits and vegetables contain little lysine, except avocados. Normal lysine metabolism is dependent upon many nutrients including niacin, vitamin B6, riboflavin, vitamin C, glutamic acid and iron. Excess arginine antagonizes lysine. Several inborn errors of lysine metabolism are known. Most are marked by mental retardation with occasional diverse symptoms such as absence of secondary sex characteristics, undescended testes, abnormal facial structure, anemia, obesity, enlarged liver and spleen, and eye muscle imbalance. Lysine also may be a useful adjunct in the treatment of osteoporosis. Although high protein diets result in loss of large amounts of calcium in urine, so does lysine deficiency. Lysine may be an adjunct therapy because it reduces calcium losses in urine. Lysine deficiency also may result in immunodeficiency. Requirements for this amino acid are probably increased by stress. Lysine toxicity has not occurred with oral doses in humans. Lysine dosages are presently too small and may fail to reach the concentrations necessary to prove potential therapeutic applications. Lysine metabolites, amino caproic acid and carnitine have already shown their therapeutic potential. Thirty grams daily of amino caproic acid has been used as an initial daily dose in treating blood clotting disorders, indicating that the proper doses of lysine, its precursor, have yet to be used in medicine. Low lysine levels have been found in patients with Parkinson's, hypothyroidism, kidney disease, asthma and depression. The exact significance of these levels is unclear, yet lysine therapy can normalize the level and has been associated with improvement of some patients with these conditions. Abnormally elevated hydroxylysines have been found in virtually all chronic degenerative diseases and coumadin therapy. The levels of this stress marker may be improved by high doses of vitamin C. Lysine is particularly useful in therapy for marasmus (wasting) and herpes simplex. It stops the growth of herpes simplex in culture, and has helped to reduce the number and occurrence of cold sores in clinical studies. Dosing has not been adequately studied, but beneficial clinical effects occur in doses ranging from 100 mg to 4 g a day. Higher doses may also be useful, and toxicity has not been reported in doses as high as 8 g per day. Diets high in lysine and low in arginine can be useful in the prevention and treatment of herpes. Some researchers think herpes simplex virus is involved in many other diseases related to cranial nerves such as migraines, Bell's palsy and Meniere's disease. Herpes blister fluid will produce fatal encephalitis in the rabbit. (http://www.dcnutrition.com). C6H14N2O2, (3S)-3,6-Diaminohexanoate, (3S,5S)-3,5-Diaminohexanoate None None None 471829.0 443819.0 435464.0 385415.0 472822.0 498043.0 435338.0 372661.0 427539.0 323573.0 479935.0 482089.0 439454.0 352758.0 421925.0 617262.0 491066.0 340077.0 382336.0 414526.0 469056.0 486002.0 487178.0 427158.0 363283.0 419059.0 446959.0 427206.0 495547.0 469271.0 437871.0 460638.0 345104.0 351710.0 622161.0 464522.0 437879.0 496178.0 341972.0 450238.0 374335.0 402419.0 146.0254799_MZ Indole-5,6-quinone Un 1.0 None None None None Indole-5,6-quinone is involved in the tyrosine metabolism pathway. More specifically, indole-5,6-quinone is an intermediate in the production of melanin. Indole-5,6-quinone is produced from 5,6-dihydroxyindole by tyrosinase [EC:1.14.18.1]. C8H5NO2 None None None 30141.7 27756.4 27539.3 25015.9 25335.4 28683.1 26089.6 28903.2 26174.6 25580.2 27212.9 28153.1 27417.3 29178.9 25890.6 25624.6 27138.3 30136.5 26339.5 29273.9 27305.9 26735.5 26234.0 27155.2 26648.0 25932.5 25735.9 28894.3 28779.6 29318.4 23297.4 24157.7 27031.1 25945.0 30440.4 27395.4 25869.7 27071.8 28096.9 26857.1 25143.2 27104.7 146.0459018_MZ L-Glutamic acid Un 1.0 None None None None Glutamic acid (Glu), also referred to as glutamate (the anion), is one of the 20 proteinogenic amino acids. It is not among the essential amino acids. Glutamate is a key molecule in cellular metabolism. In humans, dietary proteins are broken down by digestion into amino acids, which serves as metabolic fuel or other functional roles in the body. Glutamate is the most abundant fast excitatory neurotransmitter in the mammalian nervous system. At chemical synapses, glutamate is stored in vesicles. Nerve impulses trigger release of glutamate from the pre-synaptic cell. In the opposing post-synaptic cell, glutamate receptors, such as the NMDA receptor, bind glutamate and are activated. Because of its role in synaptic plasticity, it is believed that glutamic acid is involved in cognitive functions like learning and memory in the brain. Glutamate transporters are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, they can work in reverse and excess glutamate can accumulate outside cells. This process causes calcium ions to enter cells via NMDA receptor channels, leading to neuronal damage and eventual cell death, and is called excitotoxicity. The mechanisms of cell death include: * Damage to mitochondria from excessively high intracellular Ca2+. * Glu/Ca2+-mediated promotion of transcription factors for pro-apoptotic genes, or downregulation of transcription factors for anti-apoptotic genes. Excitotoxicity due to glutamate occurs as part of the ischemic cascade and is associated with stroke and diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimer's disease. glutamic acid has been implicated in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart, and this firing pattern is similar to what is known as paroxysmal depolarizing shift in epileptic attacks. This change in the resting membrane potential at seizure foci could cause spontaneous opening of voltage activated calcium channels, leading to glutamic acid release and further depolarization. (http://en.wikipedia.org/wiki/Glutamic_acid). C5H9NO4, N-Methyl-D-aspartic acid, N-Acetylserine, O-Acetylserine, L-4-Hydroxyglutamate semialdehyde None None None 978099.0 1001870.0 1083730.0 797091.0 995060.0 553586.0 786832.0 1667710.0 730252.0 740384.0 948051.0 823866.0 987254.0 1264990.0 1168870.0 548824.0 1026540.0 1030090.0 724802.0 676312.0 959167.0 871114.0 814080.0 897531.0 1253090.0 799331.0 783332.0 885305.0 1230580.0 773072.0 952306.0 858336.0 916770.0 575532.0 1241520.0 723569.0 870090.0 1029740.0 1000510.0 1065870.0 1390550.0 896399.0 147.0298102_MZ D-2-Hydroxyglutaric acid Un 1.0 None None None None D-xylonolactone is a lactone derivative of xylonic acid. It is an intermediate in the pentose and glucuronate interconversion pathway and can be formed from either D-xylonic acid or D-xylose. D-xylose is a simple 5 carbon sugar that is found in a variety of edible plants. It is also frequently used in intestinal absorption tests to help diagnose problems that prevent the small intestine from absorbing nutrients in food. Xylose is also the first saccharide added to the serine or threonine in the proteoglycan type O-glycosylation and so it is the first saccharide in biosynthetic pathways of most anionic polysaccharides such as heparan sulfate and chondroitin sulfate. D-xylose is normally easily absorbed by the intestines where it can be converted to D-xylonolactone by intestinal D-xylose 1-dehydrogenase (EC 1.1.1.175). C5H8O5, Citramalic acid, 3-Hydroxyglutaric acid, D-Xylono-1,5-lactone, L-2-Hydroxyglutaric acid, Ribonolactone None None None 159750.0 105717.0 196665.0 249216.0 151096.0 174888.0 152128.0 94264.5 145542.0 154047.0 160374.0 103805.0 85663.3 180046.0 128730.0 69105.3 101397.0 67257.0 120741.0 109783.0 146870.0 130623.0 115409.0 111110.0 95199.0 85682.3 110115.0 127673.0 108549.0 141671.0 121190.0 115148.0 91868.8 81238.3 136485.0 140149.0 134114.0 105173.0 78604.0 130385.0 61697.8 115351.0 147.0662557_MZ Mevalonic acid Un 1.0 None None None None Mevalonic acid is a key organic compound in biochemistry. It is a precursor in the biosynthetic pathway, known as the HMG-CoA reductase pathway, that produces terpenes and steroids. Mevalonate is produced by NADPH from 3-hydroxy-3-methylglutaryl CoA via reduction. This reaction occurs in the cytosol. It is the committed step in cholesterol synthesis, -- Wikipedia The production of mevalonic acid (MVA) by the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase, is the rate-limiting step in the biosynthesis of cholesterol. (Jemal et. al, Rapid Communications in Mass Spectrometry, 2003, 17:1715) Plasma concentrations and urinary excretion of MVA are decreased by HMG-CoA reductase inhibitor drugs such as pravastatin, simvastatin and atorvastatin. Naoumova RP, Marais AD, Mountney J, Firth JC, Rendell NB, Taylor GW, Thompson GR. Atherosclerosis 1996; 119: 203. C6H12O4, (R) 2,3-Dihydroxy-3-methylvalerate None None None 46697.8 35154.3 33875.8 33521.2 31524.3 40220.1 27861.2 40306.9 28603.4 35534.7 43420.1 36684.9 29030.3 44866.2 32673.0 36807.9 27759.2 31424.0 33691.7 27608.8 40412.4 33393.6 34847.9 35508.1 28453.5 34313.7 30992.2 32114.8 31964.5 52873.0 29691.7 35406.8 31818.2 26526.2 36764.2 40254.2 28184.1 29474.9 24802.5 32658.2 30268.2 35125.7 147.1177137_MZ Octanal Un 1.0 None None None None Octanal is a substrate for Fatty aldehyde dehydrogenase and Alcohol dehydrogenase. C8H16O None None None 1157.95 1561.33 1477.92 1548.32 1945.41 1630.94 1304.01 1237.02 1441.6 1354.41 1831.86 1784.63 1049.84 1350.56 1658.31 1333.34 1506.45 935.847 1074.4 1203.23 1198.02 1523.23 1723.92 1294.49 1339.54 1533.33 1523.0 1307.17 1405.73 1604.99 1138.09 1202.06 1656.68 1185.93 1475.02 1322.34 1146.43 1666.17 947.263 1514.61 941.261 1066.17 148.0438526_MZ L-Methionine Un 1.0 None None None None Methionine is a dietary indispensable amino acid required for normal growth and development of humans, other mammals, and avian species. In addition to being a substrate for protein synthesis, it is an intermediate in transmethylation reactions, serving as the major methyl group donor in vivo, including the methyl groups for DNA and RNA intermediates. Methionine is a methyl acceptor for 5-methyltetrahydrofolate-homocysteine methyl transferase (methionine synthase), the only reaction that allows for the recycling of this form of folate, and is also a methyl acceptor for the catabolism of betaine. Methionine is also required for synthesis of cysteine. Methionine is accepted as the metabolic precursor for cysteine. Only the sulfur atom from methionine is transferred to cysteine; the carbon skeleton of cysteine is donated by serine. (PMID 16702340). The adequacy range of dietary requirements of specific amino acids in disease states is difficult to determine. Requirements may not be similar in disease with regard to protein synthesis. Requirements for this purpose can be assessed only when such a function can be measured and related to clinical outcome. There is apparent consensus concerning normal sulfur amino acid (SAA) requirements. WHO recommendations amount to 13 mg/kg per 24 h in healthy adults. This amount is roughly doubled in artificial nutrition regimens. In disease or after trauma, requirements may be altered for methionine, cysteine, and taurine. Although in specific cases of congenital enzyme deficiency, prematurity, or diminished liver function, hypermethionemia or hyperhomocysteinemia may occur, SAA supplementation can be considered safe in amounts exceeding 2-3 times the minimal recommended daily intake. Apart from some very specific indications (e.g., acetaminophen poisoning) the usefulness of SAA supplementation is not yet established.(PMID 16702341). Methionine is known to exacerbate psychopathological symptoms in schizophrenic patients, there is no evidence of similar effects in healthy subjects. The role of methionine as a precursor of homocysteine is the most notable cause for concern. A loading dose of methionine (0.1 g/kg) has been given, and the resultant acute increase in plasma homocysteine has been used as an index of the susceptibility to cardiovascular disease. Although this procedure results in vascular dysfunction, this is acute and unlikely to result in permanent damage. However, a 10-fold larger dose, given mistakenly, resulted in death. Longer-term studies in adults have indicated no adverse consequences of moderate fluctuations in dietary methionine intake, but intakes higher than 5 times normal resulted in elevated homocysteine levels. These effects of methionine on homocysteine and vascular function are moderated by supplements of vitamins B-6, B-12, C, and folic acid. In infants, methionine intakes of 2 to 5 times normal resulted in impaired growth and extremely high plasma methionine levels, but no adverse long-term consequences were observed. (PMID 16702346). C5H11NO2S None None None 30120.6 48139.9 40688.6 25913.8 30585.0 34636.1 31381.2 23844.4 32184.0 30184.7 31314.8 36032.4 39386.9 30543.7 29881.6 29914.2 37465.4 28063.6 38745.7 30314.2 33039.8 29441.3 27646.2 33259.7 26954.6 24156.5 38269.7 29073.9 31768.0 32666.2 26021.5 25532.0 27095.0 27549.3 48858.3 31347.3 27806.7 35204.8 24061.2 28943.6 22740.2 26657.8 148.0626493_MZ 6-Methyladenine Un 1.0 None None None None 6-Methyladenine is a methylated adenine residue. The formation of internal 6-methyladenine (m6A) residues in eucaryotic messenger RNA (mRNA) is a postsynthetic modification in which S-adenosyl-L-methionine (SAM) serves as the methyl donor. 6-Methyladenine residues have also been localized to heterogeneous nuclear RNA (HnRNA), and for the most part these residues are conserved during mRNA processing. Although the biological significance of internal adenine methylation in eucaryotic mRNA remains unclear, a great deal of research has indicated that this modification may be required for mRNA transport to the cytoplasm, the selection of splice sites or other RNA processing reactions. The presence of m6A residues increases the in vitro translation efficiency of dihydrofolate reductase; an inhibition of m6A residues in dihydrofolate reductase transcripts significantly alters their rate of translation. m6A is found in many human fluids: oviductal fluid, blood plasma and urine. (PMID: 1551452, 8925412, 10481270, 16083005, 16684535, 3506820, 3728186). C6H7N5, 3-Methyladenine, 1-Methyladenine, 7-Methyladenine None None None 9396.05 8912.98 9294.52 8661.41 8906.67 8588.54 8925.05 9216.79 13649.1 8420.5 8910.26 9197.7 8086.95 9426.45 8235.86 8677.92 8615.34 7499.24 8223.7 8563.99 8267.14 8407.95 8928.29 8541.09 9522.22 8535.48 8528.43 8554.96 10060.3 9468.49 11042.2 9811.79 11656.0 8938.44 10274.6 8624.11 7907.02 8682.22 9417.04 8583.93 8243.13 8147.14 149.0456494_MZ D-Ribose Un 1.0 None None None None D-ribose is commonly referred to simply as ribose, a five-carbon sugar found in all living cells. Ribose is not an essential nutrient because it can be synthesized by almost every tissue in the body from other substances, such as glucose. It is vital for life as a component of DNA, RNA, ATP, ADP, and AMP. In nature, small amounts of ribose can be found in ripe fruits and vegetables. Brewer's yeast, which has a high concentration of RNA, is another rich source of ribose. D-ribose is also a component of many so-called energy drinks and antiaging products available on the market today. Ribose is a structural component of ATP, which is the primary energy source for exercising muscle. The adenosine component is an adenine base attached to the five-carbon sugar ribose. ATP provides energy to working muscles by releasing a phosphate group, hence becoming ADP, which in turn may release a phosphate group, then becoming AMP. During intense muscular activity, the total amount of ATP available is quickly depleted. In an effort to correct this imbalance, AMP is broken down in the muscle and secreted from the cell. Once the breakdown products of AMP are released from the cell, the energy potential (TAN pool) of the muscle is reduced and ATP must then be reformed using ribose. Ribose helps restore the level of adenine nucleotides by bypassing the rate-limiting step in the de novo (oxidative pentose phosphate) pathway, which regenerates 5-phosphoribosyl-l-pyrophosphate (PRPP), the essential precursor for ATP. If ribose is not readily available to a cell, glucose may be converted to ribose. Ribose supplementation has been shown to increase the rate of ATP resynthesis following intense exercise. The use of ribose in men with severe coronary artery disease resulted in improved exercise tolerance. Hence, there is interest in the potential of ribose supplements to boost muscular performance in athletic activities. (PMID: 17618002, Curr Sports Med Rep. 2007 Jul;6(4):254-7.). C5H10O5, D-Xylose, 2-Deoxyribonic acid, D-Ribulose, L-Arabinose, L-Threo-2-pentulose, D-Xylulose, L-Ribulose, Beta-D-ribopyranose, Arabinofuranose None None None 17178.2 14957.7 18021.9 12036.5 12936.1 17907.3 13071.1 12349.4 13772.4 14640.0 12848.5 14362.0 14350.0 16218.1 13904.7 18889.0 15200.4 14916.6 13746.3 14312.3 15177.3 13393.7 12936.9 13800.9 12778.6 13595.8 14896.5 13798.4 15327.9 18872.7 13787.4 14171.1 12835.9 12011.8 17991.3 18165.1 13492.2 11858.5 9079.45 13838.5 11978.6 12386.7 149.0586698_MZ Hydrocinnamic acid Un 1.0 None None None None Hydrocinnamic acid is an analogue of phenylalanine. It is a substrate of the enzyme oxidoreductases [EC 1.14.12.-] in the pathway phenylalanine metabolism (KEGG). C9H10O2, 3-Methylphenylacetic acid, 4-Coumaryl alcohol, 2-Phenylpropionate None None None 13124.9 15018.9 16117.4 13013.9 16455.1 15307.2 15955.9 16761.5 12426.0 14743.7 16537.7 16270.8 10917.3 14370.7 18107.1 15525.1 20960.1 8723.63 11330.1 12617.0 11790.2 13278.7 12899.8 13173.4 13562.0 14834.8 14218.2 14201.4 13033.1 15395.2 11029.1 11980.9 16136.3 11217.6 14072.2 10749.1 12023.4 15689.1 12031.8 15858.8 8722.38 11383.6 149.0970810_MZ (+)-(S)-Carvone Un 1.0 None None None None Carvone is a volatile terpenoid. Carvone is found in many essential oils and is very abundant in the seeds of caraway (Carum carvi). Carvone is occasionally found as a component of biological fluids in normal individuals. Caraway was used for medicinal purposes by the ancient Romans, but carvone was probably not isolated as a pure compound until Varrentrapp obtained it in1841. (PMID: 5556886, 2477620, Wikipedia). C10H14O None None None 10307.1 12340.4 13214.2 11739.6 15105.1 12789.5 12057.6 13136.5 11767.7 11568.8 14886.5 13600.5 8651.94 12554.2 13927.7 11251.0 14183.8 8076.57 9949.46 10779.5 11318.1 11905.7 12222.1 10919.1 11321.5 11571.7 13611.5 11335.6 11650.6 13037.7 9562.04 9777.67 13913.7 10030.0 11191.9 9847.94 10503.1 13022.0 9674.82 12486.1 8182.31 9888.71 150.0901321_MZ N-Methylphenylethanolamine Un 1.0 None None None None N-Methylphenylethanolamine is an intermediate in the metabolism of Tyrosine. It is a substrate for Phenylethanolamine N-methyltransferase. C9H13NO None None None 1526.54 1431.75 1286.66 1471.79 1320.49 1543.69 1475.45 1555.49 1437.83 1474.29 1547.24 1230.13 1669.43 1470.83 1467.26 1560.46 1982.62 1603.43 1404.64 1356.64 1281.98 1674.23 1512.21 1526.41 1522.21 1489.23 1633.38 1257.57 1511.97 1642.4 1262.28 1353.32 1375.14 1536.25 1520.89 1661.66 1381.51 1359.97 1581.2 1510.7 1382.98 1400.03 151.0260914_MZ Xanthine Un 1.0 None None None None Xanthine is a purine base found in most body tissues and fluids, certain plants, and some urinary calculi. It is an intermediate in the degradation of adenosine monophosphate to uric acid, being formed by oxidation of hypoxanthine. The methylated xanthine compounds caffeine, theobromine, and theophylline and their derivatives are used in medicine for their bronchodilator effects. (Dorland, 28th ed.). C5H4N4O2, 6,8-Dihydroxypurine None None None 168059.0 168978.0 198256.0 292360.0 192779.0 450393.0 291786.0 147218.0 293668.0 523654.0 224584.0 449208.0 391432.0 211097.0 332514.0 400751.0 180362.0 651314.0 367192.0 298621.0 246864.0 280512.0 318819.0 206005.0 315575.0 290132.0 287852.0 404224.0 318525.0 374886.0 178963.0 561823.0 256098.0 188836.0 340420.0 428934.0 302079.0 231813.0 280374.0 444474.0 354613.0 334149.0 151.0764184_MZ Hydroxyisocaproic acid Un 1.0 None None None None Hydroxyisocaproic acid is an end product of leucine metabolism in human tissues such as muscle and connective tissue. It belongs to 2-hydroxycarboxylic acid group of amino acid metabolites (PMID 6434570 ). Hydroxyisocaproic acid functions as an ‰ÛÏanti-catabolite‰Û and is widely used in the body building community. Chronic alpha-hydroxyisocaproic acid treatment of rats has been shown to improve muscle recovery after immobilization-induced atrophy (PMID: 23757407). Additionally, a 4-week hydroxyisocaproic acid supplementation of 1.5 g a day was shown to lead to increases in muscle mass during an intensive training period among soccer athletes (PMID: 20051111). Hydroxyisocaproic acid has also shown some potential as a topical antibiotic (PMID: 22483561). Elevated levels of 2-hydroxyisocaproic acid have been found in the urine of patients with dihydrolipoyl dehydrogenase (E3) deficiency (PMID: 6688766). Hydroxyisocaproic acid is also elevated in Maple Syrup urine disease and has been shown to accelerate lipid peroxidation. It may also be an indicator of oxidative stress (PMID: 11894849). C6H12O3, 2-Hydroxy-3-methylpentanoic acid, (5R)-5-Hydroxyhexanoic acid, 5-Hydroxyhexanoic acid, D-Leucic acid, Leucinic acid, 2-Hydroxycaproic acid, 2-Ethyl-2-Hydroxybutyric acid, (R)-3-Hydroxyhexanoic acid, 6-Hydroxyhexanoic acid None None None 10929.6 15937.5 17929.2 16822.9 22385.5 18260.0 16965.1 17768.0 15422.9 17338.1 20607.3 19431.1 9964.2 16974.5 20800.6 15224.2 19445.9 12042.5 12922.3 13571.6 12676.0 15387.7 15067.7 12915.6 14700.7 15444.8 17731.8 15535.3 13907.9 16239.7 11476.8 12510.6 16678.3 12338.6 14676.5 12943.7 12679.9 16814.0 10039.3 16425.3 9180.1 11448.9 151.1128141_MZ Alpha-Pinene-oxide Un 1.0 None None None None Alpha-pinene oxide is cheap monoterpene, which is important compound for the fragnance industry. Biocatalytic method is used to convert monoterpenes into terpenoids. The biotransformation of alpha-pinene oxide using resting cells of Pseudomonas fluorescens NCIMB 11671 produces isonovalal (cis-2-methyl-5-isopropylhexa-2,5-dienal), which is a fragrance. However, this biotransformation has technical problems including the following: alpha-pinene oxide undergoes autoxidation in water and light; it is hydrophobic and relatively toxic to the biocatalyst; and it suffers from product inhibition. the influence of other terpene byproducts on the flux of alpha-pinene oxide was investigated and found to decrease the flux into the organic phase by up to 10%. (PMID: 16321051). C10H16O, (-)-trans-Carveol, Perillyl alcohol None None None 13867.4 16067.1 14581.2 12772.9 17106.1 17869.2 14522.7 14179.3 12445.8 13336.2 19754.2 17623.4 6010.55 14849.0 15893.0 15349.4 19743.1 6050.18 10254.3 11109.7 12566.4 11297.5 15341.3 11878.0 12917.6 12431.0 16802.2 11850.9 10834.4 15681.9 11983.1 10624.3 14125.9 11506.4 12925.5 10391.7 10626.8 13383.2 7080.57 13341.1 8218.41 8709.27 152.0828162_MZ N-Acetylhistamine Un 1.0 None None None None N-Acetylhistamine is a 4-(beta-Acetylaminoethyl)imidazole that is an intermediate in Histidine metabolism. It is generated from Histamine via the enzyme Transferases (EC 2.3.1.-). Histamine is an amine derived by enzymatic decarboxylation of histidine. It is a powerful stimulant of gastric secretion, a constrictor of bronchial smooth muscle, a vasodilator, and also a centrally acting neurotransmitter. C7H11N3O None None None 4392.55 4827.89 4548.74 4441.2 4799.68 4580.62 3498.32 3948.25 5459.08 3690.14 4776.19 4987.08 2723.18 5390.38 4086.87 6288.59 4051.68 3641.97 2868.91 2950.44 3593.43 4107.57 3798.71 5585.22 4284.08 3397.27 4498.81 4283.31 4420.44 4408.42 3524.12 3828.19 3912.94 3476.3 4234.91 3821.82 3507.82 4297.83 3494.92 3742.79 3191.58 3147.53 153.0185447_MZ Gentisic acid Un 1.0 None None None None Gentisic acid is a dihydroxybenzoic acid. It is a crystalline powder that forms monoclinic prism in water solution. Gentisic acid is an active metabolite of salicylic acid degradation. There is an increasing amount of evidence indicating that gentisic acid has a broad spectrum of biological activity, such as anti-inflammatory, antirheumatic and antioxidant properties. Gentisic acid is also a byproduct of tyrosine and benzoate metabolism. C7H6O4, 2-Pyrocatechuic acid, Protocatechuic acid, 3,5-Dihydroxyphenylbenzoic acid None None None 28206.4 22916.4 26801.5 20694.0 22214.9 34838.6 24369.7 21982.2 24115.8 32228.5 23995.2 24457.5 30910.5 24648.5 26047.6 27866.2 19071.3 36715.0 27226.3 29789.8 23313.3 28042.2 29812.7 23582.3 25086.8 22253.1 22773.1 27356.5 27584.6 30225.7 20558.1 24302.7 25195.2 23549.1 26931.7 29983.9 22008.1 22949.5 19202.4 29037.5 25365.0 23891.8 153.0554354_MZ Hydroxytyrosol Un 1.0 None None None None Hydroxytyrosol is a polyphenol extracted from virgin olive oil and a natural antioxidant. It has a protective effect in preventing protein damage induced by ultraviolet radiation (PMID: 15749387). Research results suggest that Hydroxytyrosol could exert its antioxidant effect by scavenging hydrogen peroxide but not superoxide anion released during the respiratory burst(PMID: 15476671). C8H10O3 None None None 13800.1 15525.9 17290.5 14150.6 19942.5 17875.2 16611.9 17032.2 14113.8 15379.0 18409.3 16402.2 14301.1 16222.4 18200.4 17617.5 17039.8 14211.1 12997.7 14810.7 14013.9 13988.1 14711.1 13288.3 14726.2 14339.9 18360.4 15509.9 13313.0 15446.1 13252.0 13121.2 15395.7 11450.5 14010.8 12834.2 12336.6 15432.8 10844.1 15495.3 11750.9 12909.7 153.0668990_MZ L-Canaline Un 1.0 None None None None Canavanine reacts with water to produce L-canaline and urea. The reaction is catalyzed by arginase. L-canaline reacts with carbamoyl-phosphate to produce O-ureidohomoserine and phosphate. The reaction is catalyzed by ornithine carbamoyltransferase. C4H10N2O3 None None None 47626.7 34786.6 29003.0 17800.8 29983.9 39986.5 39710.3 34595.4 15500.5 20450.7 22857.4 12182.1 61839.2 22136.7 21741.9 55128.1 25384.8 61808.3 36400.5 46655.7 45580.3 11068.0 28819.6 33432.2 36416.2 18580.4 45673.7 32422.7 19371.7 24658.6 43632.2 32840.1 16395.1 23278.5 15973.7 32504.7 21357.0 12489.7 21293.0 26284.2 48869.7 44505.9 154.0621843_MZ L-Histidine Un 1.0 None None None None Histidine is an alpha-amino acid with an imidazole functional group. It is one of the 22 proteinogenic amino acids. Histidine was first isolated by German physician Albrecht Kossel in 1896. Histidine is an essential amino acid in humans and other mammals. It was initially thought that it was only essential for infants, but longer-term studies established that it is also essential for adults. Infants four to six months old require 33 mg/kg of histidine. It is not clear how adults make small amounts of histidine, and dietary sources probably account for most of the histidine in the body. Histidine is a precursor for histamine and carnosine biosynthesis. Inborn errors of histidine metabolism exist and are marked by increased histidine levels in the blood. Elevated blood histidine is accompanied by a wide range of symptoms, from mental and physical retardation to poor intellectual functioning, emotional instability, tremor, ataxia and psychosis. Histidine and other imidazole compounds have anti-oxidant, anti-inflammatory and anti-secretory properties (PMID: 9605177). The efficacy of L-histidine in protecting inflamed tissue is attributed to the capacity of the imidazole ring to scavenge reactive oxygen species (ROS) generated by cells during acute inflammatory response (PMID: 9605177). Histidine, when administered in therapeutic quantities is able to inhibit cytokines and growth factors involved in cell and tissue damage (US patent 6150392). Histidine in medical therapies has its most promising trials in rheumatoid arthritis where up to 4.5 g daily have been used effectively in severely affected patients. Arthritis patients have been found to have low serum histidine levels, apparently because of very rapid removal of histidine from their blood (PMID: 1079527). Other patients besides arthritis patients that have been found to be low in serum histidine are those with chronic renal failure. Urinary levels of histidine are reduced in pediatric patients with pneumonia. (PMID: 2084459). Asthma patients exhibit increased serum levels of histidine over normal controls (PMID: 23517038). Serum histidine levels are lower and are negatively associated with inflammation and oxidative stress in obese women (PMID: 23361591). Histidine supplementation has been shown to reduce insulin resistance, reduce BMI and fat mass and suppress inflammation and oxidative stress in obese women with metabolic syndrome. Histidine appears to suppress pro-inflammatory cytokine expression, possibly via the NF-ë¼B pathway, in adipocytes (PMID: 23361591). Low plasma concentrations of histidine are associated with protein-energy wasting, inflammation, oxidative stress, and greater mortality in chronic kidney disease patients (PMID: 18541578). Histidine may have many other possible functions because it is the precursor of the ubiquitous neurohormone-neurotransmitter histamine. Histidine increases histamine in the blood and probably in the brain. Low blood histamine with low serum histidine occurs in rheumatoid arthritis patients. Low blood histamine also occurs in some manic, schizophrenic, high copper and hyperactive groups of psychiatric patients. Histidine is a useful therapy in all patients with low histamine levels. (http://www.dcnutrition.com ). C6H9N3O2 None None None 859968.0 791697.0 796032.0 578514.0 687780.0 1084030.0 624402.0 661104.0 665057.0 509179.0 745787.0 688655.0 581157.0 689362.0 669352.0 1667160.0 607564.0 550232.0 531968.0 694282.0 693207.0 588464.0 699714.0 763950.0 712595.0 565008.0 646864.0 653380.0 837350.0 805150.0 913155.0 1180040.0 531158.0 564621.0 762628.0 688207.0 524804.0 683200.0 449811.0 673949.0 603014.0 612225.0 154.9750286_MZ Phosphoglycolic acid Un 1.0 None None None None Phosphoglycolic acid is a substrate for triose-phosphate isomerase. C2H5O6P None None None 35252.0 45875.2 35789.0 13534.9 41496.6 39374.4 35381.2 42717.3 43238.9 31685.1 40108.9 48252.5 29950.5 29400.9 37593.9 29758.9 26717.5 44213.9 35943.2 34864.8 41658.2 38770.4 35374.1 43434.3 28200.1 39372.0 39203.0 43854.8 36533.9 33209.4 28753.4 27787.6 38277.7 33294.6 44444.6 40165.1 35049.3 40231.6 23302.9 46283.4 27437.2 39784.4 155.0462603_MZ Imidazolelactic acid Un 1.0 None None None None Imidazolelactic acid is the component of normal human urine. (PMID: 5856262). histidine loading causes an increase in the excretion of imidazolelactic acid. (PMID: 6021220). During pregnancy the values for imidazolelactic acid in urine is increased 3-fold. An interaction of allergic reactions and anomalies in the metabolism of the sex hormones are considered to form the basis of the pregnancy-specific illnesses that were studied. (PMID: 5789877). Urinary excretion of imidazolelactic acid is also an indication for folic acid and vitamin B12 deficiency. (PMID: 4645251). C6H8N2O3, 5-Hydroxymethyl-4-methyluracil, 4-Imidazolone-5-propionic acid None None None 29323.6 33586.9 36338.6 48676.4 22695.6 56267.8 23808.8 37899.0 24278.4 20328.0 31638.5 28847.6 22707.2 30147.0 20156.0 76905.7 19298.2 19467.0 17053.2 21505.9 29731.9 23202.9 30297.8 29636.0 26252.9 13485.6 24170.5 24717.1 34516.1 44929.5 42407.6 52301.2 28037.5 36717.0 32489.8 35303.0 27923.9 24460.0 15885.7 18669.0 16827.5 23816.6 155.1076649_MZ 4-Hydroxynonenal Un 1.0 None None None None 4-Hydroxynonenal (HNE), one of the major end products of lipid peroxidation, has been shown to be involved in signal transduction and available evidence suggests that it can affect cell cycle events in a concentration-dependent manner. glutathione S-transferases (GSTs) can modulate the intracellular concentrations of HNE by affecting its generation during lipid peroxidation by reducing hydroperoxides and also by converting it into a glutathione conjugate. Overexpression of the Alpha class GSTs in cells leads to lower steady-state levels of HNE, and these cells acquire resistance to apoptosis induced by lipid peroxidation-causing agents such as H(2)O(2), UVA, superoxide anion, and pro-oxidant xenobiotics, suggesting that signaling for apoptosis by these agents is transduced through HNE. Cells with the capacity to exclude HNE from the intracellular environment at a faster rate are relatively more resistant to apoptosis caused by H(2)O(2), UVA, superoxide anion, and pro-oxidant xenobiotics as well as by HNE, suggesting that HNE may be a common denominator in mechanisms of apoptosis caused by oxidative stress. Transfection of adherent cells with HNE-metabolizing GSTs leads to transformation of these cells due to depletion of HNE. (PMID 15288119). C9H16O2 None None None 38126.7 50307.6 52254.2 51826.9 68800.2 66079.0 50499.8 47961.4 45103.6 47336.7 67617.6 52997.7 25575.8 60287.3 62261.7 41337.4 56933.8 21764.3 35094.2 35659.7 44798.5 43404.7 56824.4 48914.0 38247.1 41664.4 58252.9 39236.2 41071.9 52601.7 33941.7 36173.4 51527.6 35949.5 49227.7 36399.8 35964.0 53116.5 27318.3 49456.0 20394.8 33193.3 156.0300928_MZ 2-Aminomuconic acid Un 1.0 None None None None 2-Aminomuconic acid is a product of the Tryptophan metabolism degradation pathway (kinurenine pathway), in a reaction catabolized by the enzyme aminocarboxymuconate semialdehyde decarboxylase [EC:4.1.1.45]. The kynurenine pathway is the major route of L-tryptophan degradation in mammals. (BioCyc). C6H7NO4 None None None 8920.62 9290.58 14867.9 58624.6 18509.3 15223.0 23031.4 18809.8 18271.3 13453.5 31302.2 12596.8 8523.02 11515.2 20131.2 10353.1 18513.0 7171.74 17415.8 8370.94 11073.4 10874.9 19323.8 25154.5 10927.6 12835.9 27045.7 16209.9 8593.58 10188.6 9395.17 12596.3 6392.28 16723.5 10444.3 18121.2 12274.2 16748.9 5246.13 20585.7 5307.49 19483.9 156.0665716_MZ Tiglylglycine Un 1.0 None None None None Tiglylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction:. acyl-CoA + glycine < -- > CoA + N-acylglycine. Tiglylglycine is an intermediate product of the catabolism of isoleucine. An elevated level of tiglylglycine is identified in urine of patients with beta-ketothiolase deficiency or with disorders of propionate metabolism (PMID 7923765). C7H11NO3, 3-Methylcrotonylglycine None None None 17324.0 16167.6 16674.7 32086.6 17862.0 21948.9 17220.3 22304.8 16236.0 14418.2 21026.5 20700.3 10392.1 15195.5 15436.1 22638.0 19857.5 13145.6 17991.4 14090.4 15298.9 21551.7 27218.0 18668.9 14914.5 14053.1 14899.1 21046.5 19017.9 19140.7 18938.7 22284.9 10893.9 16284.9 17964.6 19326.4 16300.5 20522.3 10210.8 21073.4 13897.4 13754.1 157.0366638_MZ Allantoin Un 1.0 None None None None Allantoin is a diureide of glyoxylic acid with the chemical formula C4H6N4O3. It is also called 5-ureidohydantoin, glyoxyldiureide, and 5-ureidohydantoin. It is a product of oxidation of uric acid. It is a product of purine metabolism in most mammals except higher apes, and it is present in their urine. In humans, uric acid is excreted instead of allantoin. The presence of allantoin in the urine can be an indication of microbial overgrowth or it can be created via non-enzymatic means through high levels of reactive oxygen species. In this regard Allantoin is sometimes used as a marker of oxidative stress. Allantoin can be isolated from cow urine or as a botanical extract of the comfrey plant. It has long been used for its healing, soothing, and anti-irritating properties. Allantoin helps to heal wounds and skin irritations and stimulates the growth of healthy tissue. Allantoin can be found in anti-acne products, sun care products, and clarifying lotions because of its ability to help heal minor wounds and promote healthy skin. Allantoin is frequently present in toothpaste, mouthwash, and other oral hygiene products as well as shampoos, lipsticks, various cosmetic lotions and creams and other cosmetic and pharmaceutical products. C4H6N4O3 None None None 27708.4 27581.4 27716.8 29934.6 36517.3 36178.2 29036.1 29797.1 33747.8 31255.4 27832.1 36552.3 32598.8 37355.7 36821.1 35734.1 28977.4 26458.5 32193.3 27976.8 29550.4 35954.5 35357.6 35049.1 31873.3 27789.2 32623.0 33203.6 42443.7 29584.7 23168.3 35010.9 30598.8 26954.3 36292.1 36398.1 32809.6 34946.2 20746.0 42295.7 25635.5 32269.5 157.0505864_MZ Isopropylmaleate Un 1.0 None None None None Isopropylmaleate is found in the leucine biosynthesis pathway. 2-Isopropylmalate reversibly breaks down to form isopropylmaleate and H2O. The reaction is catalyzed by 3-isopropylmalate dehydratase. C7H10O4, Succinylacetone None None None 14556.6 15128.0 25683.9 20067.2 21248.7 16713.2 26355.4 29959.0 15919.7 17012.9 17644.2 15080.8 17428.1 17358.4 24798.5 20089.2 41359.5 11453.9 15184.0 19364.3 14348.4 15017.9 19943.6 15086.6 17922.0 14967.9 21310.1 17827.7 14624.7 18529.8 15977.8 16144.2 14222.5 13444.9 15499.5 16067.5 14400.2 14979.6 14171.4 20358.3 10737.3 16626.7 157.0869040_MZ 3-Oxooctanoic acid Un 1.0 None None None None 3-Oxo-Octanoic acid is fatty acid formed by the action of acid synthases from acetyl-CoA and malonyl-CoA precursors. It is involved in the fatty acid biosynthesis. Specifically, it is the product of reaction between malonic acid and three enzymes; beta-ketoacyl-acyl-carrier- protein synthase, fatty-acid Synthase and beta-ketoacyl -acyl-carrier- protein synthase II. C8H14O3, cis-4-Hydroxycyclohexylacetic acid, trans-4-Hydroxycyclohexylacetic acid, Alpha-Ketooctanoic acid None None None 23514.7 25821.1 24058.9 24546.9 26254.1 25418.5 25497.0 28122.6 20989.0 23380.0 25814.8 21136.9 17897.8 26787.3 28209.1 21190.5 29851.9 23152.2 20764.8 23154.8 24034.7 20408.5 24811.6 27611.6 22106.7 20426.4 26237.4 23698.2 19219.8 26490.8 19424.6 20459.3 20678.0 23282.8 22402.3 24831.3 19870.6 22534.3 20328.8 24313.3 17394.4 21444.2 157.1232740_MZ Oenanthic ether Un 1.0 None None None None Oenanthic ether is an odorous substance (ester) (PMID 15474656) present in human sweat (PMID 8887339). C9H18O2, Pelargonic acid None None None 127561.0 129540.0 108763.0 116425.0 104364.0 127547.0 120559.0 135499.0 109820.0 116258.0 106048.0 91158.8 102606.0 129754.0 117674.0 91496.6 143450.0 119103.0 116873.0 112087.0 124611.0 100209.0 120072.0 154120.0 104384.0 98391.1 106351.0 115842.0 98739.6 133005.0 98871.2 86442.3 93281.1 114880.0 112194.0 118847.0 104839.0 90148.8 129206.0 120643.0 84940.9 121863.0 158.0821713_MZ 2-Methylbutyrylglycine Un 1.0 None None None None 2-Methylbutyrylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction:. acyl-CoA + glycine < -- > CoA + N-acylglycine. The isolated excretion of high levels of 2-methylbutyrylglycine (2-MBG) is the hallmark of short/branched-chain acyl-CoA dehydrogenase deficiency or SBCADD (PMID:15615815). The disorder is also called 2-methylbutyryl-CoA dehydrogenase deficiency (PMID: 17883863) and has been associated with autism and mental retardation. SBCADD is a recently described autosomal recessive disorder caused by a defect in the degradation pathway of L- isoleucine leading to increased urinary excretion of 2-methylbutyryl glycine. The enzymatic defect results from disruption of the SBCAD gene. Deficiency of SBCAD leads to accumulation of its substrate, 2-methylbutyryl-CoA within the mitochondrion. This substance is transesterified with glycine by the mitochondrial enzyme acyl-CoA glycine-N-acyltransferase (glycine-N-acylase) to form 2-methylbutyryl glycine. Affected patients can be divided into two categories. The first category consists of infants detected by newborn screening programmes. These infants are treated with diet and remain without clinical symptoms. In the second category affected patients are diagnosed because they presented clinically with seizures and psychomotor delay and have increased urinary excretion of 2-methylbutyryl glycine (PMID: 17883863). 2-methylbutyrylglycine has also been found in the urine of patients with propionyl-CoA carboxylase deficiency after consuming isoleucine. (PMID: 630060). 2-methylbutyrylglycine is also elevated in the urine of patients with glutaric aciduria II and ethylmalonic encephalopathy. C7H13NO3, Isovalerylglycine, Valerylglycine, N-Acetylvaline, 3-Dehydrocarnitine, 5-Acetamidovalerate None None None 22611.7 18440.7 17361.0 44703.5 15182.4 22602.2 21029.5 26768.0 18409.6 21391.3 18908.1 32836.6 12610.6 24230.1 13573.0 30469.9 26820.4 30585.5 23276.5 15031.7 15099.3 14974.7 24758.5 21923.4 20880.3 14908.5 16385.4 24231.1 18865.5 22390.0 45809.4 32022.5 12708.1 19414.7 14666.2 21359.5 19310.0 14743.7 11907.1 19715.5 20244.2 17219.7 158.1186864_MZ DL-2-Aminooctanoic acid Un 1.0 None None None None alpha-Aminooctanoic acid is an amino compound found occasionally in human urine. (PMID: 13447222). alpha-Aminooctanoic acid has been found in one case in the milk of a lactating mother at the 144th day of lactation. (Science and Culture (1960), 26 186-7.). C8H17NO2 None None None 2392.36 2202.65 2800.63 3037.78 2285.03 2517.42 2259.27 2720.94 2450.47 2700.8 3194.38 3221.76 2089.38 2549.78 2234.16 2480.83 2646.42 2873.37 1709.7 2444.97 2583.25 2020.67 2514.73 2436.57 1868.08 2363.44 1796.85 2788.65 2090.02 3085.39 2078.67 1989.14 2062.79 1806.88 2812.83 2598.75 1949.94 1836.81 1185.45 2295.54 1991.92 1921.02 159.0300131_MZ Oxoadipic acid Un 1.0 None None None None 2-Oxoadipic acid is produced from lysine in the cytosol of cells via the saccharopine and the pipecolic acid pathways. Catabolites of hydroxylysine and tryptophan enter these pathways as 2-aminoadipic- -semialdehyde and 2-oxoadipate, respectively. In the matrix of mitochondria, 2-oxoadipate is decarboxylated to glutaryl-CoA by the 2-oxoadipate dehydrogenase complex and then converted to acetyl-CoA. 2-Oxoadipic aciduria is an in-born error of metabolism of lysine, tryptophan, and hydroxylysine, in which abnormal quantities of 2-aminoadipic acid are found in body fluids along with 2-oxoadipic acid. Patients with 2-Oxoadipic acidemias are mentally retarded with hypotonia or seizures. 2-Oxoadipic Aciduria can occur in patients with Kearns-Sayre Syndrome, a progressive disorder with onset prior to 20 years of age in which multiple organ systems are affected, including progressive external ophthalmoplegia, retinopathy, and the age of onset, and these are associated classically with abnormalities in cardiac conduction, cerebellar signs, and elevated cerebrospinal fluid protein. (PMID: 10655159, 16183823, 11083877). C6H8O5, 3-Oxoadipic acid None None None 11902.7 9025.05 10791.3 10837.2 10043.6 11075.3 9806.07 10861.4 8997.7 9522.28 9976.65 10142.5 8387.22 12350.5 11601.0 11009.4 10178.2 9378.36 9362.36 9269.15 9426.06 9285.22 9634.67 10573.8 9054.76 8837.34 11066.0 9181.28 9947.74 11461.8 9132.97 9417.81 8049.16 9504.32 9293.47 10143.2 8477.46 9016.06 8008.39 9592.81 7726.66 9730.1 159.0564295_MZ Methylimidazoleacetic acid Un 1.0 None None None None Methylimidazoleacetic acid is the main metabolite of histamine. This end product of histamine catabolism is formed by N-methylation in the imidazole ring to methylhistamine by histamine methyltransferase (EC 2.1.1.8) and a subsequent oxidative deamination in the side chain by type B monoamine oxidase (EC 1.4.3.4). From studies is known that as much as 70 to 80 percent of the histamine metabolized in the body is excreted in the urine as Methylimidazoleacetic acid. Thus, urinary Methylimidazoleacetic acid being the major and specific histamine metabolite is a clear marker of any changes in histamine metabolism in the body. The urinary excretion of methylimidazoleacetic acid is considered a reliable indicator of histamine turnover rate in the body. The excretion of Methylimidazoleacetic acid is higher in men than women however; this gender difference is abolished when corrected for creatinine excretion. A possible explanation is that basal histamine turnover is related to body size. There is no significant difference in Methylimidazoleacetic acid excretion between smokers and non-smokers when analysing absolute values (mg/24 h). When using Methylimidazoleacetic acid values corrected for creatinine excretion female smokers have significantly higher Methylimidazoleacetic acid excretion compared to nonsmokers. (PMID: 11411609, 7130180, 10350179, 10202992). C6H8N2O2, 1,3-Dimethyluracil, Imidazolepropionic acid, Pi-Methylimidazoleacetic acid None None None 1862.52 1810.39 2430.36 2211.66 2497.63 2132.1 2422.24 2132.5 2403.87 2132.73 2447.44 2027.61 1851.44 1996.98 2756.68 2015.98 2391.98 1361.32 2027.51 1971.65 1805.99 2106.7 2011.19 1662.31 2259.07 2489.35 2553.26 2009.94 1912.1 1915.92 1940.55 2241.37 1941.22 1981.38 1868.15 1667.89 2111.63 2162.29 2000.7 2214.21 2120.09 2197.75 159.0662113_MZ 3-Methyladipic acid Un 1.0 None None None None 3-Methyladipic acid is a metabolite of the catabolism of phytanic acid. Patients with adult Refsums disease (ARD) are unable to detoxify phytanic acid by alpha-oxidation, and so the w-oxidation pathway is the only metabolic pathway available for phytanic acid degradation. This pathway produces 3-methyladipic acid as the final metabolite, which is excreted in the urine (Wanders et al. 2001). Activity of the w-oxidation pathway is approximately doubled in ARD patients compared with normal individuals (PMID: 11948235). C7H12O4, Pimelic acid, 3,3-Dimethylglutaric acid None None None 22300.3 20931.2 21551.3 21511.8 18108.8 18263.9 19546.3 29958.9 13218.3 15404.2 14479.3 12347.1 12096.3 19028.9 21923.9 17554.9 35919.5 10667.4 12612.7 15960.8 16404.8 9808.7 13468.4 22712.6 15860.4 10669.3 18475.0 14023.5 9572.77 22996.4 13518.1 13670.7 9207.13 17651.7 11144.6 18663.4 12621.8 8594.08 11757.6 18480.9 9049.37 18733.2 159.0780279_MZ D-Alanyl-D-alanine Un 1.0 None None None None The ATP-dependent carboxylate-amine/thiol ligase superfamily is known to contain enzymes catalyzing the formation of various types of peptide, one of which is d-alanyl-d-alanine.(PMID: 16030213). The glycopeptide antibiotic vancomycin acts by binding to the D-alanyl-D-alanine terminus of the cell wall precursor lipid II in the cytoplasmic membrane.(PMID: 17418637). D-alanine-D-alanine ligase from Thermotoga maritima ATCC 43589 (TmDdl) was a useful biocatalyst for synthesizing D-amino acid dipeptides.D-Alanine-D-alanine ligase (Ddl) catalyzes the biosynthesis of an essential bacterial peptidoglycan precursor D-alanyl-D-alanine and it represents an important target for development of new antibacterial drugs. (PMID: 17267218). C6H12N2O3 None None None 8414.44 7022.91 8075.88 7823.27 7288.13 7520.78 6462.15 9131.82 6987.84 5662.33 6740.91 7157.14 4748.0 8074.91 7844.06 6835.13 7121.04 5055.4 4709.12 5318.33 5634.55 6983.33 5329.27 6955.5 6184.13 6786.04 6540.52 7232.56 7561.53 7385.56 5519.4 6544.8 5522.66 5625.61 8507.93 7383.72 6870.91 6213.39 5120.68 7284.48 5022.48 6490.24 159.1025125_MZ 7-Hydroxyoctanoic acid Un 1.0 None None None None 7-Hydroxyoctanoic acid is a normal metabolite of medium-chain fatty acid oxidation, and is excreted in the urine as 7-hydroxyoctanoyl-beta-D-glucuronide (PMID 8799296), and have been found slightly elevated in the urine of persons with abnormal fatty acid metabolism (PMID 2094705). C8H16O3, Hydroxyoctanoic acid, 3-Hydroxyoctanoic acid, (R)-2-Hydroxycaprylic acid, (R)-3-Hydroxyoctanoic acid None None None 10582.9 9621.84 6684.94 10517.4 7941.72 9414.46 8019.25 9404.84 7896.73 8992.71 8225.59 6185.69 6290.05 9549.93 8528.56 7289.3 8295.5 7759.97 8155.94 7507.68 9169.94 6111.91 9152.38 10697.3 7724.28 6803.22 7393.33 7301.21 6172.44 10686.5 6646.43 6517.13 5843.81 8292.42 6525.99 10627.0 7461.37 6394.33 6484.09 9254.18 7103.81 8711.92 159.1138446_MZ N(6)-Methyllysine None None None None None None N(6)-Methyllysine is a naturally occurring amino acid found in human biofluids. N-monomethyl-lysine is generated by metabolic transmethylation of endogenous lysine. Lysine methylation displays the highest degree of complexity among known covalent histone modifications, with each site of methylation regulating the association of different effector molecules. The versatility of lysine methylation marks is perhaps best exemplified by modifications implicated in transcriptional regulation as well as being required for double-strand break repair in several organisms. Identification of the numerous biological functions encoded by histone lysine methylation is a major area of research interest, as these mechanisms are intimately associated with cellular senescence, genomic instability, and leukemogenesis. While multiple sites of lysine methylation have been linked with gene activation, each modification is distributed to unique positions across the active gene. (PMID: 17030614, 1122639, 15756599, 3111294). C7H16N2O2, Isoputreanine; N6-Methyl-L-lysine; Methyllysine None None None 7125.16 3359.86 2971.02 9046.55 6645.71 3250.46 2946.82 4653.24 5832.08 5376.3 2924.39 3319.1 3955.9 5571.01 6261.97 2917.97 7299.0 2129.6 6493.14 2900.37 7385.12 7709.71 7324.85 4256.01 6551.46 7915.58 3122.66 2235.52 2991.16 3420.46 6227.04 5182.84 2777.69 6552.5 9328.35 6334.48 6468.93 7688.8 4365.14 7729.29 2334.18 2628.51 160.0401699_MZ 4,6-Dihydroxyquinoline Un 1.0 None None None None 4,6-Dihydroxyquinoline is the product of the conversion of 5-hydroxykynurenamine by the enzyme monoamine oxidase, both metabolites from the 5-hydroxytryptophan metabolism. (PMIDs 7160021, 312499). C9H7NO2, 2-Indolecarboxylic acid, Indole-3-carboxylic acid None None None 9064.64 10364.6 11011.0 9017.24 8062.49 11807.2 8305.85 8737.76 7400.15 9369.33 7838.94 9396.06 10370.0 10791.8 7702.23 13293.1 11400.0 10307.6 7062.27 10958.3 10959.9 8271.76 8772.17 9905.53 9100.92 7591.45 8692.81 10217.9 10469.0 14254.8 11000.9 10215.9 7165.47 8152.65 7405.75 9298.89 6845.31 8132.56 6527.9 8543.31 7437.21 8443.64 160.0614417_MZ Aminoadipic acid Un 1.0 None None None None Aminoadipic acid (2-aminoadipate) is a metabolite in the principal biochemical pathway of lysine. It is an intermediate in the metabolism (i.e. breakdown or degradation) of lysine and saccharopine.(Wikipedia). It antagonizes neuroexcitatory activity modulated by the glutamate receptor, N-methyl-D-aspartate; (NMDA). Aminoadipic has also been shown to inhibit the production of kynurenic acid in brain tissue slices (PMID: 8566117). Kynurenic acid is a broad spectrum excitatory amino acid receptor antagonist. Recent studies have shown that aminoadipic acid is elevated in prostate biopsy tissues from prostate cancer patients (PMID: 23737455). Mutations in DHTKD1 (dehydrogenase E1 and transketolase domain-containing protein 1) have been shown to cause human 2-aminoadipic and 2-oxoadipic aciduria via impaired turnover of decarboxylation 2-oxoadipate to glutaryl-CoA, which is the last step in the lysine degradation pathway (PMID: 23141293). Aging, diabetes, sepsis and renal failure are known to catalyze the oxidation of lysyl residues to 2-aminoadipic acid in human skin collagen and potentially other tissues (PMID: 18448817). Proteolytic breakdown of these tissues can lead to the release of free 2-aminoadipic acid. Studies in rats indicate that aminoadipic acid (along with the 3 branched chain amino acid ‰ÛÒ Leu, Val and Ile) levels are elevated in the pre-diabetic phase and so aminoadipic acid may serve as a predictive biomarker for the development of diabetes. (PMID: 15389298). Long-term hyperglycemia of endothelial cells leads to elevated levels of aminoadipate which is though to be a sign of lysine breakdown through oxidative stress and reactive oxygen species (ROS) (PMID: 21961526). 2-aminoadipate is a potential small-molecule marker of oxidative stress (PMID: 21647514) C6H11NO4 None None None 63463.8 28180.8 43618.1 59059.4 44820.8 31882.9 37711.8 46806.5 50486.6 23263.1 29003.1 63809.8 16513.8 33562.4 32355.0 63789.8 23993.4 43339.6 20861.1 34639.1 24028.0 37162.1 41816.9 26147.3 41550.9 25993.9 22181.8 44832.8 51942.8 53798.8 53324.9 40237.0 28394.8 32629.2 34640.0 25448.5 33471.5 31708.1 28163.9 32105.8 26851.1 23187.9 160.8906630_MZ Phosphoroselenoic acid Un 1.0 None None None None Phosphoroselenoic acid, H3SePO3, is the activated selenium donor compound required for the biosynthesis of selenocysteyl-tRNA, the precursor of specific selenocysteine residues in bacterial and mammalian selenoproteins. Selenocysteine is the 21st amino acid, because Sec has a specific tRNA and codon UGA, and shares a major stop codon UGA. A number of enzymes have selenocysteine, residues and in some cases at their active sites. Proteins containing the 21st amino acid, selenocysteine (Sec), have been described in all three domains of life. (PMID: 18156471). H3O3PSe None None None 889.616 1000.75 1138.37 685.998 1299.0 1131.78 1772.7 1179.46 1319.9 1003.56 933.366 1323.99 1322.86 870.058 1102.77 879.707 1538.75 983.149 1167.4 1522.52 1106.99 968.357 1058.89 819.089 1067.19 1156.55 1237.32 1257.85 814.454 826.768 1522.64 960.162 1003.25 1194.06 1042.56 856.421 1247.1 1551.81 1147.83 800.229 1334.49 921.53 161.0455326_MZ 2-Hydroxyadipic acid Un 1.0 None None None None 2-Hydroxyadipic acid is a hydroxy-dicarboxylic acid formed by the reduction of 2-ketoadipic acid. Deficiency of 2-ketoadipic dehydrogenase causes 2-ketoadipic acidemia (OMIM 245130), a condition characterized by accumulation and excretion of 2-hydroxyadipic acid (with 2-ketoadipic and 2-aminoadipic) probably without adverse phenotypic effects.(OMMBID - The Metabolic and Molecular Bases of Inherited Disease, CH.95). A method involving derivatization and combined gas chromatography--mass spectrometry has been recently developed to separate the enantiomers of 3-hydroxyadipic acid (PMID: 3980660). It has been shown that 3-hydroxyadipic acid excreted in urine consists of at least 95% of the L-enantiomer. This finding supports the hypothesis that dicarboxylic acids are degraded by ordinary beta-oxidation, and indicates that adipic acid may be converted into succinic acid. (PMID: 3980660). C6H10O5, 3-Hydroxyadipic acid, 3-Hydroxymethylglutaric acid, 2(R)-Hydroxyadipic acid, Levoglucosan None None None 124466.0 120214.0 156325.0 182829.0 125223.0 146978.0 129459.0 117912.0 124812.0 146552.0 125789.0 129537.0 134656.0 136361.0 133951.0 134698.0 132093.0 123750.0 151119.0 140028.0 136451.0 129126.0 131703.0 118927.0 102007.0 106834.0 159895.0 147582.0 145614.0 137875.0 126857.0 106152.0 92124.3 120146.0 145222.0 156992.0 118119.0 121784.0 75009.0 149884.0 133239.0 115817.0 162.0226501_MZ Acetylcysteine Un 1.0 None None None None Acetylcysteine is the N-acetyl derivative of the amino acid L-cysteine, and is a precursor in the formation of the antioxidant glutathione in the body. The thiol (sulfhydryl) group confers antioxidant effects and is able to reduce free radicals. wikipedia. It is used as a mucolytic agent to reduce the viscosity of mucous secretions. It has also been shown to have antiviral effects in patients with HIV due to inhibition of viral stimulation by reactive oxygen intermediates. -- Pubchem. Acetylcysteine is a pharmacological agent used in the management of paracetamol overdose. For these indications, acetylcysteine is available under the trade names Mucomyst (Bristol-Myers Squibb) and Parvolex (GSK.-- Wikipedia. C5H9NO3S None None None 21649.5 20237.7 14173.7 18617.9 20174.2 23046.6 18299.1 16909.2 10241.8 16795.0 16880.5 11329.4 14744.8 20276.0 16850.9 17583.0 17634.1 16998.4 20562.0 68826.5 15612.9 10220.4 17529.5 16466.2 16328.8 10940.8 22596.9 14417.7 10767.7 20770.3 88920.7 16374.4 9379.6 57710.3 11267.0 22356.4 10085.0 9837.86 20795.5 20064.5 103354.0 18343.4 162.0772529_MZ Bicine Un 1.0 None None None None Bicine is a general purpose buffer for biological research. Its applications include: tissue culture,phosphorylation and photophosphorylation, fixative transmission electron microscopy, protein synthesis and preventing binding to non-receptor materials. It is a degradation product of alkanolamine and alkylalkanolamine solutions. C6H13NO4 None None None 4758.09 3618.09 3740.79 3614.33 3989.89 4469.07 4442.84 4244.91 4552.18 3772.06 3963.0 3664.37 3562.98 4365.89 4116.44 4370.83 5657.1 3207.3 4114.63 4366.85 4334.5 3341.86 4467.75 4051.34 4187.8 3693.41 4046.66 4470.95 3517.22 4281.26 5522.76 4020.78 3560.16 4834.08 3661.85 4390.64 3251.91 3154.56 2910.25 4034.94 4782.93 3753.99 162.8905400_MZ Molybdate Un 1.0 None None None None Molybdate is involved in the molybdenum cofactor biosynthesis pathway. Molybdate reacts with molybdopterin-AMP to produce molybdenum cofactor, AMP, and H2O. H2MoO4 None None None 1633.54 1846.74 1983.37 1747.0 1902.2 2096.71 2684.18 1916.64 2086.0 1908.2 1801.13 2196.3 2267.25 1687.35 2029.36 2038.24 2297.52 1758.1 2081.12 2214.48 1646.82 1708.48 1898.59 1434.42 1988.57 1838.43 2074.77 1845.87 1681.82 1713.41 2246.37 1758.1 1999.02 1998.68 1389.72 1588.26 1949.65 2430.62 1872.39 1679.21 2410.36 1939.25 163.0389740_MZ Phenylpyruvic acid Un 1.0 None None None None Phenylpyruvic acid is a keto-acid that is an intermediate or catabolic byproduct of phenylalanine metabolism. It has a slight honey-like odor. Levels of phenylpyruvate are normally very low in blood or urine. High levels of phenylpyruvic acid can be found in the urine of individuals with phenylketonuria (PKU). PKU is due to lack of the enzyme phenylalanine hydroxylase (PAH), so that phenylalanine is converted not to tyrosine but to phenylpyruvic acid. In particular, excessive phenylalanine can be metabolized into phenylketones through, a transaminase pathway route involving glutamate. Metabolites of this transamination reaction include phenylacetate, phenylpyruvate and phenethylamine. In persons with PKU, dietary phenylalanine either accumulates in the body or some of it is converted to phenylpyruvic acid. Individuals with PKU tend to excrete large quantities of phenylpyruvate, phenylacetate and phenyllactate, along with phenylalanine, in their urine. If untreated, mental retardation effects and microcephaly are evident by the first year along with other symptoms which include: unusual irritability, epileptic seizures and skin lesions. Hyperactivity, EEG abnormalities and seizures, and severe learning disabilities are major clinical problems later in life. A musty or mousy odor of skin, hair, sweat and urine (due to phenylacetate accumulation); and a tendency to hypopigmentation and eczema are also observed. The neural-development effects of PKU are primarily due to the disruption of neurotransmitter synthesis. In particular, phenylalanine is a large, neutral amino acid which moves across the blood-brain barrier (BBB) via the large neutral amino acid transporter (LNAAT). Excessive phenylalanine in the blood saturates the transporter. Thus, excessive levels of phenylalanine significantly decrease the levels of other LNAAs in the brain. But since these amino acids are required for protein and neurotransmitter synthesis, phenylalanine accumulation disrupts brain development, leading to mental retardation. C9H8O3, m-Coumaric acid, 4-Hydroxycinnamic acid, 2-Hydroxycinnamic acid, Enol-phenylpyruvate None None None 15382.5 16354.5 17209.9 15535.6 17579.4 17853.9 15441.1 16383.8 16329.6 16972.4 16858.1 18677.1 14901.7 17385.6 16405.3 14948.6 17213.2 16961.0 16864.5 15978.1 15198.8 17775.0 16124.3 15888.4 15587.7 16235.5 16767.7 16769.0 16593.4 19830.0 13814.8 12899.4 18321.1 17164.2 17647.8 15941.1 16818.2 17574.0 18666.6 16604.8 13391.0 14629.7 163.0611330_MZ L-Fucose Un 1.0 None None None None Fucose is a hexose deoxy sugar with the chemical formula C6H12O5. L-fucose (6-deoxy-L-galactose) is a monosaccharide that is a common component of many N- and O-linked glycans and glycolipids produced by mammalian cells. It is the fundamental sub-unit of the fucoidan polysaccharide. As a free sugar, L-fucose is normally found at very low levels in mammals. It is unique in that it is the only levorotatory sugar synthesized and utilized by mammals. Fucose polymers are synthesized by fucosyltransferases. All fucosyltransferases utilize a nucleotide-activated form of fucose, GDP-fucose, as a fucose donor in the construction of fucosylated oligosaccharides. The ABO blood group antigens are among the most well known fucosylated glycans. The alpha-1->3 linked core fucose is a suspected carbohydrate antigen for IgE-mediated allergy. Two structural features distinguish fucose from other six-carbon sugars present in mammals: the lack of a hydroxyl group on the carbon at the 6-position (C-6) and the L-configuration. In fucose-containing glycan structures, fucosylated glycans, fucose can exist as a terminal modification or serve as an attachment point for adding other sugars. Fucose is metabolized by an enzyme called alpha-fucosidase. Fucose is secreted in urine when the liver is damaged. Free L-fucose in serum and urine can be used as a marker for cancer, cirrhosis, alcoholic liver disease and gastric ulcers (PMID: 2311216) (PMID: 8488966). Elevated levels of serum fucose have been reported in breast cancer, ovarian cancer, lung cancer, liver cancer, diabetes and cardiovascular disease. It has been shown that feeding rats a diet high in L-fucose induces neuropathy similar to that seen in diabetics. C6H12O5, Rhamnose, 1,5-Anhydrosorbitol, Beta-D-Fucose, L-Rhamnulose, 2-Deoxygalactopyranose None None None 89038.5 102321.0 72232.7 60954.6 81171.5 101728.0 40591.6 32808.4 94694.5 89225.6 81092.3 82420.7 84429.3 105668.0 98514.9 108875.0 76221.7 84061.5 65562.9 39889.4 87846.2 83115.9 61738.0 107192.0 95095.1 34544.7 84421.3 87784.0 59510.6 65112.7 43884.6 72549.6 96638.2 96326.5 54825.8 72660.3 91631.4 49919.0 21975.0 92956.1 50172.7 62920.5 163.0768772_MZ 2-Phenylbutyric acid Un 1.0 None None None None 2-Phenylbutyric acid is used as an anticholesteremic. C10H12O2, Benzenebutanoic acid, 3-Phenylbutyric acid, Isoeugenol, Eugenol None None None 22069.1 28438.4 46327.6 31834.6 41471.7 35183.1 28378.2 26129.9 36809.6 31789.3 40139.4 44497.2 18276.3 29710.5 40130.1 32029.9 33726.3 35354.2 35226.8 33566.9 28924.8 47071.8 36786.5 37825.3 33010.2 51125.2 36762.5 41164.0 50671.5 24099.6 26687.9 28675.8 41900.8 37686.2 64600.7 29296.3 37764.6 37027.6 29850.2 36855.1 33552.6 38962.1 164.0386237_MZ Methionine sulfoxide Un 1.0 None None None None Methionine sulfoxide is an oxidation product of methionine with reactive oxygen species via 2-electron-dependent mechanism. Such oxidants can be generated from activated neutrophils; therefore, methionine sulfoxide can be regarded as a biomarker of oxidative stress in vivo. (PMID 12576054). C5H11NO3S None None None 7238.29 7759.39 7175.63 7306.9 7632.88 7398.22 8211.55 7074.54 6883.67 8121.21 6273.9 7645.11 5033.21 7206.75 7809.56 8285.56 8013.53 7154.73 7785.72 6380.97 6411.9 6535.31 6918.44 6821.82 6822.62 7226.79 7914.59 6793.65 7128.65 7785.67 6947.23 6847.95 6897.59 7627.07 9516.87 7000.21 7021.48 7602.37 6309.7 6164.49 6138.96 6148.99 164.0580482_MZ 3-Methylguanine Un 1.0 None None None None 3-Methylguanine is a methylated purine base. Methylated purine bases are known to be present in normal urine and to change under pathological conditions, in particular in the development of leukemia, tumors and immunodeficiency, by the altered turnover of nucleic acids typical of these diseases. (PMID 9069642). C6H7N5O, 7-Methylguanine, 1-Methylguanine, N2-Methylguanine None None None 6877.65 8678.93 10168.6 8266.01 6551.78 7546.52 6778.4 6610.66 11784.2 6860.26 7114.81 12306.0 6795.1 6663.7 6565.44 7665.6 8420.17 5630.66 6911.88 8426.87 8209.4 8509.9 8169.66 8200.45 7579.08 8013.25 8265.35 7944.21 9768.32 6991.23 11585.6 8312.47 11276.3 8643.25 9029.36 6658.55 7451.68 8902.51 5678.71 7220.1 7722.34 6724.7 164.0715830_MZ L-Phenylalanine Un 1.0 None None None None Phenylalanine is an essential amino acid and the precursor for the amino acid tyrosine. Like tyrosine, it is the precursor of catecholamines in the body (tyramine, dopamine, epinephrine and norepinephrine). The psychotropic drugs (mescaline, morphine, codeine, and papaverine) also have phenylalanine as a constituent. Phenylalanine is a precursor of the neurotransmitters called catecholamines, which are adrenalin-like substances. Phenylalanine is highly concentrated in the human brain and plasma. Normal metabolism of phenylalanine requires biopterin, iron, niacin, vitamin B6, copper and vitamin C. An average adult ingests 5 g of phenylalanine per day and may optimally need up to 8 g daily. Phenylalanine is highly concentrated in high protein foods, such as meat, cottage cheese and wheat germ. A new dietary source of phenylalanine is artificial sweeteners containing aspartame. Aspartame appears to be nutritious except in hot beverages; however, it should be avoided by phenylketonurics and pregnant women. Phenylketonurics, who have a genetic error of phenylalanine metabolism, have elevated serum plasma levels of phenylalanine up to 400 times normal. Mild phenylketonuria can be an unsuspected cause of hyperactivity, learning problems, and other developmental problems in children. Phenylalanine can be an effective pain reliever. Its use in premenstrual syndrome and Parkinson's may enhance the effects of acupuncture and electric transcutaneous nerve stimulation (TENS). Phenylalanine and tyrosine, like L-dopa, produce a catecholamine effect. Phenylalanine is better absorbed than tyrosine and may cause fewer headaches. Low phenylalanine diets have been prescribed for certain cancers with mixed results. Some tumors use more phenylalanine (particularly melatonin-producing tumors called melanoma). One strategy is to exclude this amino acid from the diet, i.e., a Phenylketonuria (PKU) diet (compliance is a difficult issue; it is hard to quantify and is under-researched). The other strategy is just to increase phenylalanine's competing amino acids, i.e., tryptophan, valine, isoleucine and leucine, but not tyrosine. (http://www.dcnutrition.com). C9H11NO2, 3-Pyridinebutanoic acid, Benzocaine, Norsalsolinol None None None 214945.0 182207.0 239323.0 117857.0 196046.0 283952.0 184736.0 172078.0 244397.0 189289.0 159116.0 275638.0 239529.0 214877.0 200680.0 221876.0 154917.0 217941.0 207644.0 233636.0 192318.0 240798.0 201649.0 186628.0 173485.0 185463.0 231780.0 220987.0 261012.0 212400.0 131888.0 146547.0 245514.0 157855.0 288592.0 247966.0 190838.0 202492.0 122691.0 216129.0 163889.0 180224.0 164.1074926_MZ Pseudoephedrine Un 1.0 None None None None Pseudoephedrine (commonly abbreviated as PSE) is a sympathomimetic amine commonly used as a decongestant. The salts pseudoephedrine hydrochloride and pseudoephedrine sulfate are found in many over-the-counter preparations either as single ingredient preparations, or more commonly in combination with antihistamines, paracetamol and/or ibuprofen. Consumers often refer to it by a product which contains pseudoephedrine, such as Sudafed, the trademark for a common brand of pseudoephedrine hydrochloride in North America; Pseudoephedrine is a phenethylamine, and an isomer of ephedrine. Pseudoephedrine is the International Nonproprietary Name (INN) of the (1S,2S)- diastereomer of ephedrine (which has 1R,2S- configuration). Other names are (+)-pseudoephedrine and D-pseudoephedrine. (Reynolds, 1989) (-)-(1R,2R)-Pseudoephedrine is not used clinically, since it is associated with greater central nervous system (CNS) stimulatory effects. (+)-(1S,2S)-Pseudoephedrine is a less-potent CNS stimulant, yet it retains its efficacy as a decongestant. -- Wikipedia; Pseudoephedrine is a sympathomimetic amine - that is, its principal mechanism of action relies on its indirect action on the adrenergic receptor system. While it may have weak agonist activity at adrenergic receptors, the principal mechanism is to displace noradrenaline from storage vesicles in presynaptic neurons. The displaced noradrenaline is released into the neuronal synapse where it is free to activate the aforementioned postsynaptic adrenergic receptors. -- Wikipedia; Pseudoephedrine is a phenethylamine, and an isomer of ephedrine. Pseudoephedrine is the International Nonproprietary Name (INN) of the (1S,2S)- diastereomer of ephedrine (which has 1R,2S- configuration). Other names are (+)-pseudoephedrine and D-pseudoephedrine (Reynolds, 1989). The enantiomer (-)-(1R,2R)-Pseudoephedrine has fewer side-effects, fewer central nervous system (CNS) stimulatory effects, does not reduce to d-methamphetamine, yet retains its efficacy as a decongestant.[citation needed] However, the patent holder for (-)-Pseudoephedrine (Pfizer/Warner-Lambert) has not yet sought or received government approval for its sale to the public.(US Patent 6,495,529); Treatment for urinary incontinence is an unlabeled use for these medications. Unlabeled use means doctors can use the medication to treat a condition other than that for which it was first approved by the U.S. Food and Drug Administration (FDA). These medications are approved by the FDA for the treatment of nasal congestion caused by colds or allergies. However it has also been succesful in treating stress incontinence by increasing the pressure (tension) exerted by the muscles of the bladder neck and the urethra, which helps retain the urine within the bladder; An alpha and beta adrenergic agonist that may also enhance release of norepinephrine. It has been used in the treatment of several disorders including asthma, heart failure, rhinitis, and urinary incontinence, and for its central nervous system stimulatory effects in the treatment of narcolepsy and depression. It has become less extensively used with the advent of more selective agonists; Pseudoephedrine is a sympathomimetic amine commonly used as a decongestant. The salts pseudoephedrine hydrochloride and pseudoephedrine sulfate are found in many over-the-counter preparations either as single-ingredient preparations, or more commonly in combination with antihistamines, paracetamol and/or ibuprofen. It is often referred to by consumers as Sudafed, which is the trademark for a common brand of pseudoephedrine hydrochloride. -- Wikipedia; Pseudoephedrine is a sympathomimetic amine - that is, its principal mechanism of action relies on its indirect action on the adrenergic receptor system. While it may have weak agonist activity at alpha and beta adrenergic receptors, the principal mechanism is to displace noradrenaline from storage vesicles in presynaptic neurons. The displaced noradrenaline is released into the neuronal synapse where it is free to activate the aforementioned postsynaptic adrenergic receptors. C10H15NO, Hordenine None None None 3862.52 3498.43 3895.55 3160.16 3484.53 4854.81 3445.8 3321.99 3807.96 3413.21 3407.67 4101.65 3590.37 4294.77 3653.4 3387.67 3228.03 3534.47 3306.57 3611.18 3718.49 3594.58 3883.06 3801.13 3217.17 3208.9 3794.48 3559.06 3675.18 4235.58 2743.23 2818.59 3718.72 3169.73 4194.35 3920.26 3357.68 3541.54 2753.39 3729.47 2715.48 3260.91 165.0191732_MZ Benzoquinoneacetic acid Un 1.0 None None None None Benzoquinoneacetic acid is an oxidized phase of the oxidation-reduction system homogentisic-benzoquinoneacetic acid. This compound is secreted in large quantities in the urine of patients suffering from cyanosis. Cyanosis is the bluish coloration of the skin due to the presence of deoxygenated hemoglobin in blood vessels near the skin surface. (Ella H. Fishberg, J. Biol. Chem., Jan 1948; 172: 155 - 163; Wikipedia). C8H6O4 None None None 47367.3 46477.1 43174.0 48848.9 43791.0 52270.9 52463.6 65822.4 38685.4 50541.9 48973.4 37621.6 41420.2 46241.3 45056.2 37382.2 54603.6 57794.2 47877.0 48943.0 45883.4 34886.2 48365.7 52949.6 50661.0 46695.5 42125.7 51406.3 35409.9 49535.4 41772.1 35122.2 35817.9 45387.6 34118.4 49409.4 38874.0 32714.8 45132.4 47444.3 48403.3 48405.0 165.0404476_MZ Ribonic acid Un 1.0 None None None None Ribonic acid is a product of the enzyme ribose 1-dehydrogenase (NADP+) [EC 1.1.1.115] (KEGG). C5H10O6, Arabinonic acid None None None 145078.0 111859.0 141085.0 82029.1 96899.6 127447.0 95206.0 94281.1 105154.0 113616.0 103421.0 109393.0 84163.4 128157.0 132754.0 107349.0 92651.1 87488.3 97516.7 87943.8 119329.0 101161.0 91877.9 112724.0 88792.3 99521.0 119544.0 95725.5 93889.6 156101.0 96558.1 79194.4 89579.2 86999.5 119938.0 122103.0 85220.4 94899.4 62115.6 94906.4 76916.2 84061.3 166.0180421_MZ Homocysteinesulfinic acid Un 1.0 None None None None Homocysteinesulfinic acid, is involved in many metabolic pathways including trans-sulfuration in cysteine synthesis, re-methylation in methionine synthesis,. trans-methylation of DNA, proteins, and lipids, and biosynthesis of small hormonal and neuronal signaling molecules. C4H9NO4S None None None 955508.0 840097.0 1405400.0 1082820.0 1283170.0 1126270.0 744047.0 715629.0 1870950.0 1126820.0 1698060.0 1485640.0 840964.0 1015380.0 1159030.0 724992.0 1167590.0 885229.0 1017750.0 686137.0 1318670.0 1754940.0 1086700.0 1297020.0 843800.0 1183330.0 1139700.0 1101900.0 1296250.0 866435.0 707038.0 770261.0 2051330.0 971841.0 1719790.0 2126710.0 1269250.0 1439210.0 468282.0 1754040.0 492228.0 1186650.0 166.9751266_MZ Phosphoenolpyruvic acid Un 1.0 None None None None Phosphoenolpyruvate (PEP) is an important chemical compound in biochemistry. It has a high energy phosphate bond, and is involved in glycolysis and gluconeogenesis. In glycolysis, PEP is formed by the action of the enzyme enolase on 2-phosphoglycerate. Metabolism of PEP to pyruvate by pyruvate kinase (PK) generates 1 molecule of adenosine triphosphate (ATP) via substrate-level phosphorylation. ATP is one of the major currencies of chemical energy within cells. In gluconeogenesis, PEP is formed from the decarboxylation of oxaloacetate and hydrolysis of 1 guanosine triphosphate molecule. This reaction is catalyzed by the enzyme phosphoenolpyruvate carboxykinase (PEPCK). This reaction is a rate-limiting step in gluconeogenesis. (wikipedia). C3H5O6P None None None 4524.86 5279.73 5645.73 4193.05 6461.42 5126.83 6220.15 5939.9 5576.09 5056.82 5000.53 5549.18 4699.59 6017.25 6187.55 4722.77 6566.2 4078.92 4929.63 6547.37 5026.76 5061.53 4556.08 4436.97 6102.39 4693.39 6562.79 4337.04 4329.03 5114.64 6624.48 4691.62 5836.0 5404.02 4936.12 3809.62 5303.84 5018.67 3794.28 4623.32 5049.15 4279.7 167.0209758_MZ Uric acid Un 1.0 None None None None Uric acid is a heterocyclic purine derivative that is the final oxidation product of purine metabolism. It is produced by the enzyme xanthine oxidase, which oxidizes oxypurines such as xanthine into uric acid. In most mammals, except humans and higher primates, the enzyme uricase further oxidizes uric acid to allantoin. Uric acid is also the end product of nitrogen metabolism in birds and reptiles. In such species, it is excreted in feces as a dry mass. Humans produce only small quantities of uric acid with excess accumulation leading to a type of arthritis known as gout. The loss of uricase in higher primates parallels the similar loss of the ability to synthesize ascorbic acid vitamin C. This may be because in higher primates uric acid partially replaces ascorbic acid. C5H4N4O3 None None None 328154.0 257322.0 340000.0 160836.0 291133.0 429194.0 341821.0 300773.0 220227.0 357908.0 339462.0 282195.0 391617.0 365274.0 296009.0 385570.0 329285.0 460577.0 347089.0 303216.0 408244.0 204582.0 422890.0 355103.0 226417.0 309451.0 372821.0 391033.0 176553.0 334370.0 276318.0 312114.0 285021.0 141111.0 192675.0 449810.0 158923.0 174242.0 193536.0 333444.0 285879.0 385259.0 167.0966406_MZ Nornicotine Un 1.0 None None None None Nornicotine is an alkaloid extracted from tobacco and related to nicotine but having a lower toxicity: used as an agricultural and horticultural insecticide. C9H12N2 None None None 2404.87 2536.67 2743.44 2364.13 2952.75 3038.05 2515.62 2823.5 2101.01 2517.28 2973.0 2728.79 2194.45 2634.03 2753.54 2980.4 2871.14 2844.68 2560.2 2443.74 2766.17 2184.35 2644.87 2592.03 2212.14 2575.95 2793.3 2758.4 2174.75 2530.55 2242.74 2293.24 2536.89 1951.61 2393.8 2842.8 1949.13 2307.91 1798.74 2386.17 2149.04 2552.44 167.1077452_MZ trans-4,5-epoxy-2(E)-decenal Un 1.0 None None None None Polyunsaturated fatty acids such as arachidonate and linoeate, while essential to health maintenance, are subject to random peroxidation by ambient oxygen, resulting in fragmented and reactive decomposition products. One prominent autoxidation product of either trilinolein or arachidonic acid is trans-4,5-epoxy-2(E)-decenal. This aldehyde is responsible for a pungent metallic flavor of decomposed lipids, with a detection threshold of 1.5 pg/l in air.1 trans-4,5-epoxy-2(E)-Decenal also reacts with nucleophiles (lysine amino groups) on proteins, leading to loss of cell function and viability.2 This reactive aldehyde is therefore a useful tool in elucidating the effects of peroxidative damage in experimental models. C10H16O2 None None None 33532.2 40559.7 29558.2 26473.2 38713.4 44452.8 33220.7 31014.7 27080.4 31546.7 47009.9 37350.8 12244.8 35512.8 33999.7 35758.1 42437.1 11325.6 21458.3 23558.6 30651.0 23467.8 34638.0 27214.6 26531.1 24029.6 39569.6 26330.3 20345.0 40085.4 25527.9 22251.3 29231.4 28617.7 26328.9 23730.4 21638.0 28598.7 11410.6 28062.1 15828.0 17247.4 167.9979939_MZ Cysteic acid Un 1.0 None None None None C3H7NO5S None None None 4043.65 3624.29 5384.63 4062.49 4839.98 4213.54 4349.5 4325.76 4541.51 4184.67 4701.03 4195.78 4096.16 4913.64 4185.9 3000.17 4932.47 5298.63 5260.01 4308.65 4939.15 4990.85 4081.31 4616.23 4434.86 4530.43 3866.66 5018.79 5037.4 4604.37 3520.49 3246.76 5708.88 4887.37 4153.37 4605.63 5096.68 4185.42 4738.15 4193.78 4465.73 4083.55 168.0666064_MZ Pyridoxine Un 1.0 None None None None The 4-methanol form of vitamin B6 which is converted to pyridoxal phosphate which is a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. Although pyridoxine and Vitamin B6 are still frequently used as synonyms, especially by medical researchers, this practice is erroneous and sometimes misleading (EE Snell; Ann NY Acad Sci, vol 585 pg 1, 1990). Pyridoxine is one of the compounds that can be called vitamin B6. Pyridoxine assists in the balancing of sodium and potassium as well as promoting red blood cell production. It is linked to cancer immunity and helps fight the formation of homocysteine. It has been suggested that Pyridoxine might help children with learning difficulties, and may also prevent dandruff, eczema, and psoriasis. In addition, pyridoxine can help balance hormonal changes in women and aid in immune system. Lack of pyridoxine may cause anemia, nerve damage, seizures, skin problems, and sores in the mouth. -- Wikipedia Deficiency, though rare because of widespread distribution in foods, leads to the development of peripheral neuritis in adults and affects the central nervous system in children (DOSE - 3rd edition). C8H11NO3, Norepinephrine, 6-Hydroxydopamine, 5-Hydroxydopamine None None None 15223.4 13683.4 16130.9 16042.1 10425.7 12989.8 10965.0 11433.5 13500.6 11880.1 11279.6 9679.3 15597.3 17929.1 11195.7 13434.5 13599.3 16179.9 13666.9 14881.8 15566.8 11849.8 11064.5 12623.3 13683.7 9207.4 9568.05 11723.1 15170.6 19913.4 11463.5 10306.9 13105.9 10016.7 18292.1 15563.5 15799.7 15720.5 12790.5 12441.8 11599.2 9245.24 168.0778102_MZ 1-Methylhistidine Un 1.0 None None None None One-methylhistidine (1-MHis) is derived mainly from the anserine of dietary flesh sources, especially poultry. The enzyme, carnosinase, splits anserine into b-alanine and 1-MHis. High levels of 1-MHis tend to inhibit the enzyme carnosinase and increase anserine levels. Conversely, genetic variants with deficient carnosinase activity in plasma show increased 1-MHis excretions when they consume a high meat diet. Reduced serum carnosinase activity is also found in patients with Parkinson's disease and multiple sclerosis and patients following a cerebrovascular accident. Vitamin E deficiency can lead to 1-methylhistidinuria from increased oxidative effects in skeletal muscle. C7H11N3O2, 3-Methylhistidine None None None 15682.7 17726.8 24593.8 24069.3 23615.7 22288.6 24248.4 29913.6 18757.2 17927.3 23247.7 21514.4 18333.3 18044.8 19977.9 17491.8 20124.5 13869.8 16357.6 18674.7 31172.7 23285.2 21892.6 18434.8 21873.0 26031.6 16658.9 17148.3 22723.2 18838.6 20636.2 18382.5 22620.7 20733.8 25562.4 18414.8 17992.1 23199.1 15322.6 25469.3 15967.6 22846.7 169.0079240_MZ Diethylthiophosphate Un 1.0 None None None None Diethylthiophosphate is the most frequent metabolite of organophosphorus (OP) found in urine (PMID 15050412). Organophosphorus compounds are widely used as pesticides because of easy degradation in the environment. Acute OP intoxication results from blockage of the decomposition of synaptic acetylcholine because the pesticide covalently binds to chlolinesterase (PMID 11991535). Chronic exposure to POs has neurological sequelae as well (PMID 8179040) and data suggests that OP exposure alters sperm chromatin condensation (PMID 15050412). C4H11O3PS None None None 13697.1 9873.63 13361.8 18655.5 10821.2 13553.6 10631.1 9955.59 10081.5 12841.7 12018.9 10938.7 11065.4 13289.9 8266.51 18238.4 14007.2 11279.7 13568.7 10028.9 9045.45 10932.5 12431.9 11876.1 12562.4 12055.8 12173.8 14443.3 10707.1 11009.0 17757.0 12823.0 11733.2 10431.7 11954.1 12286.2 10149.7 12177.2 6284.99 11449.7 15776.2 10617.1 169.0304572_MZ Phenylglyoxylic acid Un 1.0 None None None None Phenylglyoxylic acid is one of the major urinary metabolites of toluene, o-, m- and p-xylenes, styrene and ethylbenzene. (PMID 3782394). For the biological monitoring of workers exposure to solvent used in industry, its concentration is measured in human urine samples. (PMID 2739101). C8H6O3 None None None 14949.6 13907.4 15380.6 15268.7 13869.3 11284.8 12353.0 19902.5 10886.2 14763.5 14381.4 12126.2 15364.0 18084.9 16856.0 11941.2 15618.3 17151.6 12446.1 11600.3 13341.0 13073.0 13504.5 14291.8 17569.2 13065.9 11805.4 14793.7 16806.0 12791.9 14152.1 16103.7 14651.2 10083.9 16348.7 12571.8 12815.8 14038.9 15456.2 15493.7 20594.2 13652.2 169.1232940_MZ cis-4-Decenoic acid Un 1.0 None None None None 4-Decenoic acid (and other intermediates of unsaturated fatty acid oxidation) has been found in increased amounts in liver, skeletal muscle and heart obtained post mortem from patients with medium-chain acyl-CoA dehydrogenase deficiency (MCADD), multiple acyl-CoA dehydrogenase deficiency (MADD) and very long-chain acyl-CoA dehydrogenase deficiency (VLCADD) (PMID 11486898). C10H18O2, trans-Dec-2-enoic acid, 8-Methylnonenoate None None None 21499.0 25077.1 16880.1 20979.7 20749.5 25300.2 20133.7 20097.6 18202.1 19549.0 25789.2 23784.2 9792.95 19673.4 19158.0 21886.5 25604.2 11669.5 14466.4 15070.0 20342.6 14616.0 21730.1 18854.4 16720.0 14521.9 22692.6 17756.2 13532.0 23462.2 16228.4 14728.8 15599.3 17761.9 17426.2 16512.3 15694.4 15744.2 9647.01 17066.0 10016.5 12930.2 170.0454569_MZ Tetrahydrodipicolinate Un 1.0 None None None None Tetrahydrodipicolinate, converted from L-aspartate, is an important intermediate in lysine biosynthesis pathway. Several pathways are now recognized in bacteria, most algae, fungi and higher plants for the biosynthesis of lysine. They are divided into two groups - the diaminopimelate (DAP) pathways, and the α-aminoadipate (AAA) pathways. In the pathways that belong to the DAP group, lysine is produced from aspartate (along with methionine, threonine and isoleucine). All of these pathways share the upper segments, which include the four steps required for conversion of L-aspartate to tetrahydrodipicolinate. They also share the last step, which is the conversion of the intermediate meso-diaminopimelate (D,L-DAP, or meso-DAP) to lysine. However, these pathways differ in the routes leading from tetrahydrodipicolinate to meso-diaminopimelate. The four variations include: (I) the succinylase variant, which involves succinylated intermediates. In this route tetrahydrodipicolinate is coverted to meso-diaminopimelate in four enzymatic steps; (II) the acetylase variant, which involves acetylated intermediates. This route also involves four enzymatic steps for the conversion of tetrahydrodipicolinate to meso-diaminopimelate; (III) the dehydrogenase variant, in which tetrahydrodipicolinate is converted to meso-diaminopimelate in a single enzymatic step; (IV) the diaminopimelate-aminotransferase variant, in which tetrahydrodipicolinate is converted to meso-diaminopimelate in two steps. In addition to lysine, the pathways in this group also produce meso-DAP, which is an important metabolite on its own. C7H9NO4 None None None 32647.1 30199.0 32955.5 27909.1 39789.6 37310.1 31319.5 23770.0 34710.1 30633.6 30064.5 26019.2 30431.3 31269.5 39098.5 38821.1 40291.6 38229.3 26676.0 28271.6 27242.9 27238.6 33000.4 27680.2 35512.3 20913.1 26124.2 32804.2 40143.8 32780.8 26990.1 35205.1 24587.6 20248.7 35086.9 29723.6 23440.4 35030.6 19926.2 32801.2 28800.3 23380.9 170.1183614_MZ Gabapentin Un 1.0 None None None None C9H17NO2 None None None 3783.57 3919.64 3834.25 3820.91 3643.5 3481.21 4500.18 4768.49 3536.88 3825.14 4103.28 3490.17 3804.11 3989.69 3739.18 3318.49 4531.86 5871.83 3468.66 4631.9 3700.12 3416.53 3704.75 4018.92 3778.68 3438.26 3767.26 4050.08 3262.31 4105.87 3655.89 3307.74 3517.53 4516.55 3435.85 4036.26 3145.47 3725.71 3692.63 3923.15 3908.26 3590.6 171.0065094_MZ Glycerol 3-phosphate Un 1.0 None None None None Glycerol 3-phosphate is a chemical intermediate in the glycolysis metabolic pathway. It is commonly confused with the similarly named glycerate 3-phosphate or glyceraldehyde 3-phosphate. Glycerol 3-phosphate is produced from glycerol, the triose sugar backbone of triglycerides and glycerophospholipids, by the enzyme glycerol kinase. Glycerol 3-phospate may then be converted by dehydrogenation to dihydroxyacetone phosphate (DHAP) by the enzyme glycerol-3-phosphate dehydrogenase. DHAP can then be rearranged into glyceraldehyde 3-phosphate (GA3P) by triose phosphate isomerase (TIM), and feed into glycolysis. The glycerol 3-phosphate shuttle is used to rapidly regenerate NAD+ in the brain and skeletal muscle cells of mammals (wikipedia). C3H9O6P, Beta-Glycerophosphoric acid None None None 3013320.0 2891910.0 2655580.0 1325250.0 2510510.0 3178220.0 2819140.0 2687830.0 2664650.0 2587050.0 2882450.0 2704630.0 2307510.0 2184690.0 2685260.0 2627550.0 1606360.0 2879400.0 2623760.0 2456540.0 3198460.0 2319530.0 2569800.0 3242160.0 2264670.0 3248330.0 2347340.0 2550050.0 2645810.0 2650490.0 2610830.0 2183300.0 2636130.0 1966960.0 2168260.0 3384690.0 2773600.0 2523720.0 1141130.0 2970950.0 2582790.0 2818030.0 171.1390527_MZ Capric acid Un 1.0 None None None None Capric acid is a member of the series of fatty acids found in oils and animal fats. The names of Caproic, Caprylic, and Capric acids are all derived from the word caper (Latin: 'goat'). These are colorless light yellowish transparent oily liquids with unconfortable smells. These are used in organic synthesis, manufacture of perfume, medicine, lubricating grease, rubber and dye.(ChemicalLAND21). C10H20O2 None None None 60294.7 62764.5 55517.4 50498.2 53684.7 66680.4 66711.4 72072.1 50940.8 57411.9 53902.3 49972.5 48254.3 59569.0 59375.0 49455.4 77368.5 66141.5 60508.2 63387.7 62256.1 48322.5 57776.5 75957.2 54057.4 48556.7 55660.8 64577.6 50326.1 61240.7 51635.2 45400.7 45614.7 57687.3 58209.8 59925.3 50885.7 47787.9 52970.4 62896.2 45414.1 60236.5 172.0980498_MZ Hexanoylglycine Un 1.0 None None None None Hexanoylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction:acyl-CoA + glycine < -- > CoA + N-acylglycineHexanoylglycine is a fatty acid metabolite, it appears in the urine of patients with hereditary medium-chain acyl-CoA dehydrogenase (MCAD) deficiency (PMID 2775902). C8H15NO3, Isovalerylalanine, Isovalerylsarcosine None None None 68220.7 51672.0 55426.3 75178.2 75258.3 58741.7 47140.0 43874.1 60173.4 53045.2 53210.2 97811.3 53628.7 53610.2 36834.9 109126.0 36569.8 67800.5 40163.6 49102.3 42430.8 40287.6 40790.0 46226.2 49263.6 34931.4 36997.4 51765.2 65769.5 49351.7 41621.4 51862.8 45821.6 40536.2 31423.9 63674.0 35937.5 59720.0 18070.3 42683.8 44797.6 38601.2 173.0087921_MZ Dehydroascorbic acid Un 1.0 None None None None Dehydroascorbic acid is the oxidized form of vitamin C. Reduced Vitamin C concentrations in the brain exceed those in blood by 10 fold. Dehydroascorbic acid readily enters the brain and is retained in the brain tissue in the form of ascorbic acid (ascorbic acid is not able to cross the blood-brain barrier). Therefore, transport of dehydroascorbic acid by the Glucose Transporter 1 (GLUT1, Glucose transporters are integral membrane glycoproteins involved in transporting glucose into most cells. GLUT1 is a major glucose transporter in the mammalian blood-brain barrier. It is present at high levels in primate erythrocytes and brain endothelial cells.) is a mechanism by which the brain acquires vitamin C. (OMIM 138140). C6H6O6, cis-Aconitic acid, trans-Aconitic acid None None None 76089.3 81797.4 93391.3 79091.3 135083.0 124923.0 157262.0 92514.7 95664.2 102304.0 94654.3 104934.0 129133.0 103618.0 108925.0 168953.0 112935.0 91029.4 125344.0 199213.0 78752.0 79439.2 102427.0 76880.9 108462.0 99619.3 132444.0 86297.3 84463.4 102690.0 164223.0 178695.0 101611.0 90708.5 73234.9 79037.0 79295.1 85289.9 82079.8 86359.3 234273.0 87393.9 173.0455782_MZ 2-Isopropyl-3-oxosuccinate Un 1.0 None None None None 2-Isopropyl-3-oxosuccinate is an intermediate in leucine biosynthesis and can be generated from (2R,3S)-3-Isopropylmalate. It is the third step in leucine biosynthesis after the fork from valine synthesis. It is an oxidative decarboxylation. Leucine biosynthesis involves a five-step conversion process starting with the valine precursor 2-keto-isovalerate. The final step in this pathway is catalyzed by two transaminases of broad specificity, Branched-chain amino acid transferase (IlvE) and Tyrosine aminotransferase (TyrB). In this pathway 2-Isopropyl-3-oxosuccinate is converted to 4-Methyl-2-oxopentanoate via spontaneous reaction.(BioCyc). C7H10O5, Shikimic acid None None None 15105.4 13513.9 39138.9 18181.3 25429.7 14290.9 30204.3 52939.4 11447.2 13748.8 14182.3 12161.9 18823.4 15748.2 43501.6 32760.5 80793.8 13578.8 17636.2 28647.8 12412.5 10956.8 13399.8 13645.9 21219.9 12185.3 30431.0 16401.1 11008.7 17909.5 19493.9 20585.7 10809.4 10830.7 11554.7 19096.4 11139.2 11616.9 16701.7 22104.1 11560.1 21919.6 173.0566678_MZ N-Acetylasparagine Un 1.0 None None None None N-Acetylasparagine is produced by degradation of asparagine and identified in human urine. C6H10N2O4, Formiminoglutamic acid None None None 27411.7 28341.5 26085.1 25206.8 30754.3 26671.2 19967.4 24942.8 28901.1 19635.8 23958.3 26068.7 16019.1 23067.7 25573.3 47674.6 27575.5 19375.5 17692.7 18355.0 21881.0 19360.7 20505.7 19229.0 23118.1 14234.4 25969.0 21914.4 27010.2 27812.4 21502.4 24527.4 16119.8 16488.5 20333.2 24550.5 17488.0 21394.1 14400.4 19303.6 15724.6 16596.4 173.0818531_MZ Suberic acid Un 1.0 None None None None Suberic acid, also octanedioic acid, is a dicarboxylic acid, with formula C6H12(COOH)2. It is present in the urine of patients with Fatty Acid Oxidation Disorders (PMID 10404733). A metabolic breakdown product derived from oleic acid. Elevated levels of this unstaruated dicarboxylic acid are found in individuals with dicarboxylic acid and medium-chain acyl-CoA dehydrogenase deficiency (MCAD). C8H14O4, Ethyladipic acid None None None 56642.6 54452.1 29494.2 59596.6 26613.7 36517.0 28149.6 37952.6 33762.4 35531.5 30923.7 21280.2 19358.4 45223.3 31147.2 32152.1 41661.7 22173.7 25407.8 24563.4 48602.1 19268.8 31627.5 61538.0 33630.9 20963.8 26930.2 24962.6 19710.4 63833.9 22995.0 28424.3 18054.6 35908.3 24577.3 54083.0 33847.4 18416.1 21917.2 46804.3 18728.3 38512.5 173.0933320_MZ N-Acetylornithine Un 1.0 None None None None N-Acetylornithine is a minor components of deproteinized blood plasma of human blood. Human blood plasma contains a variable amount of acetylornithine, averaging 1.1 +/- 0.4 mumol/l (range 0.8--0.2 mumol/l). Urine contains a very small amount of acetylornithine, approximately 1 nmol/mg creatinine (1 mumol/day). (PMID: 508804). C7H14N2O3 None None None 23852.6 20913.2 17335.3 29599.1 15617.4 21585.7 15787.8 19561.5 18687.8 15293.1 20412.2 17333.7 11518.1 18225.3 15139.2 23524.5 20709.7 12229.4 13343.7 13370.0 22776.2 18245.8 18493.6 18999.4 16867.2 15726.8 19219.0 18293.2 19596.5 26862.3 19263.7 17978.4 14225.7 15750.2 27519.3 22402.8 19368.0 15895.8 8813.63 19494.4 11067.9 16322.2 173.1042000_MZ L-Arginine Un 1.0 None None None None Arginine is an essential amino acid that is physiologically active in the L-form. In mammals, arginine is formally classified as a semiessential or conditionally essential amino acid, depending on the developmental stage and health status of the individual. Infants are unable to effectively synthesize arginine, making it nutritionally essential for infants. Adults, however, are able to synthesize arginine in the urea cycle. Arginine can be considered to be a basic amino acid as the part of the side chain nearest to the backbone is long, carbon-containing and hydrophobic, whereas the end of the side chain is a complex guanidinium group. With a pKa of 12.48, the guanidinium group is positively charged in neutral, acidic and even most basic environments. Because of the conjugation between the double bond and the nitrogen lone pairs, the positive charge is delocalized. This group is able to form multiple H-bonds. L-arginine is an amino acid that has numerous functions in the body. It helps dispose of ammonia, is used to make compounds such as nitric oxide, creatine, L-glutamate, L-proline, and it can be converted to glucose and glycogen if needed. In large doses, L-arginine also stimulates the release of hormones growth hormone and prolactin. Arginine is a known inducer of mTOR (mammalian target of rapamycin) and is responsible for inducing protein synthesis through the mTOR pathway. mTOR inhibition by rapamycin partially reduces arginine-induced protein synthesis PMID: 20841502. Catabolic disease states such as sepsis, injury, and cancer cause an increase in arginine utilization, which can exceed normal body production, leading to arginine depletion. Arginine also activates AMP kinase (AMPK) which then stimulates skeletal muscle fatty acid oxidation and muscle glucose uptake, thereby increasing insulin secretion by pancreatic beta-cells. PMID: 21311355 Arginine is found in plant and animal proteins, such as dairy products, meat, poultry, fish, and nuts. The ratio of L-arginine to lysine is also important - soy and other plant proteins have more L-arginine than animal sources of protein. C6H14N4O2 None None None 19824.6 15205.2 14977.3 13471.3 19333.9 20205.0 15453.7 17103.5 13599.8 13484.7 13789.8 16806.9 18386.0 18450.4 14548.5 21006.3 12450.0 17271.0 24741.7 16574.0 14946.9 10334.5 14388.7 15699.9 12543.6 12326.7 26805.1 15379.8 11722.8 21199.8 13497.0 15356.5 11597.1 10483.3 14640.6 24821.3 9522.79 11394.9 9625.34 12832.2 13515.3 18305.0 174.0163787_MZ Monodehydroascorbate Un 1.0 None None None None C6H7O6 None None None 15958.1 25429.4 21135.3 25579.0 25117.7 18892.6 24496.0 22704.8 15779.2 16540.9 18063.4 19470.7 27347.9 15793.8 22498.3 29535.4 23561.0 26487.9 22889.0 24031.7 22333.2 16526.9 20291.6 24513.7 24617.8 21968.0 28679.1 18572.8 23483.9 12706.5 31312.3 33508.3 21187.7 18581.3 20190.2 23633.2 16578.9 17813.7 17521.9 22564.6 27104.2 23934.4 174.0407174_MZ N-Acetyl-L-aspartic acid Un 1.0 None None None None N-Acetylaspartic acid is a derivative of aspartic acid. It is the second most concentrated molecule in the brain after the amino acid glutamate. It is synthesized in neurons from the amino acid aspartate and acetyl coenzyme A. The various functions served by N-acetylaspartic acid are still under investigation, but the primary proposed functions include:. 1) A neuronal osmolyte that is involved in fluid balance in the brain 2) A source of acetate for lipid and myelin synthesis in oligodendrocytes, the glial cells that myelinate neuronal axons 3) A precursor for the synthesis of the important neuronal dipeptide N-acetylaspartylglutamate 4)N-Acetylaspartic acid may also be involved in energy production from the amino acid glutamate in neuronal mitochondria. C6H9NO5, N-Formyl-L-glutamic acid None None None 35072.2 21422.2 36836.2 30581.8 28545.0 45980.7 36243.5 32454.9 27537.2 28914.3 24832.1 31901.0 45336.4 112421.0 34368.0 31838.0 31464.7 23183.6 26548.8 32736.1 35385.4 23691.0 32063.9 26036.4 26394.3 24163.3 38214.5 29687.6 29728.4 36555.5 27143.1 26986.5 20886.5 21610.0 27225.9 21666.9 22519.4 30046.6 22798.0 29392.1 26187.1 30162.1 174.0769717_MZ N-Carboxyethyl-g-aminobutyric acid Un 1.0 None None None None Induces formation of Epstein Barr Virus lymphocytes immediately following infection. (282990). C7H13NO4 None None None 9193.51 7719.6 8456.76 12282.3 7429.05 8354.47 8675.03 10826.4 8538.85 7535.19 9275.66 10919.5 4776.39 8199.82 7304.38 9771.33 9421.94 5355.43 6530.31 5989.05 6723.83 7964.7 9820.09 7336.42 7151.14 6463.07 7640.48 8527.72 7783.48 9996.58 9324.48 9431.06 5636.15 7703.03 7009.9 7770.21 7133.23 8091.68 3911.34 7751.43 6005.23 6566.05 174.0883657_MZ Citrulline Un 1.0 None None None None Citrulline is an amino acid made from ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from arginine as a by-product of the reaction catalyzed by NOS family (NOS; EC 1.14.13.39). In this reaction arginine is first oxidized into N-hydroxyl-arginine, which is then further oxidized to citrulline concomitant with the release of nitric oxide. EC 1.14.13.39). Citrulline's name is derived from citrullus, the Latin word for watermelon, from which it was first isolated. C6H13N3O3, Argininic acid None None None 22015.5 15862.9 12807.4 14656.7 10973.5 21210.0 14668.2 15478.8 11938.7 15101.9 14805.4 10496.3 8559.16 19572.8 12564.6 21000.5 17567.2 11984.7 11268.7 11751.4 16683.8 10567.9 12737.5 16501.9 14090.1 8996.71 14778.3 12819.8 11359.3 24984.9 17027.5 19303.1 9493.02 12230.7 15364.0 17985.7 14687.4 11018.6 9735.41 14130.9 9209.54 14284.3 175.0248617_MZ D-Glucurono-6,3-lactone Un 1.0 None None None None D-glucurono-6,3-lactone participates in ascorbate and aldarate metabolism. D-glucurono-6,3-lactone is produced by the reaction between D-glucaric acid and the enzyme, aldehyde dehydrogenase (NAD+) [EC: 1.2.1.3]. C6H8O6, Ascorbic acid None None None 6199540.0 12577000.0 8889230.0 14256400.0 11961600.0 5934200.0 10022600.0 11203200.0 6153510.0 5949820.0 6798550.0 6565130.0 14336100.0 6025660.0 10039400.0 11205100.0 11950600.0 11865100.0 11776400.0 9740680.0 9513220.0 6191030.0 8931500.0 12637100.0 11961300.0 10598600.0 15214000.0 8064710.0 11657300.0 2640230.0 13375600.0 14477600.0 9465240.0 9088470.0 7996210.0 10650700.0 7646210.0 6287700.0 9524930.0 10927100.0 12971100.0 13229600.0 177.0919694_MZ 5-Phenylvaleric acid Un 1.0 None None None None 5-Phenylvaleric acid is a Pentanoic acid of bacterial origin, occasionally found in human biofluids. (PMID 9389332). C11H14O2 None None None 11040.4 15396.4 17135.1 16555.0 22488.3 16030.6 16063.2 17531.6 14640.1 14952.8 20529.7 18349.5 9124.33 16205.9 19839.5 14380.3 19185.3 9829.47 12906.6 13418.4 12111.5 14800.0 14880.3 12748.0 14248.2 14974.5 17090.9 14685.4 13640.2 14907.4 11551.7 11636.0 16889.0 11704.8 13435.7 11673.8 12562.4 17159.0 9752.72 16374.0 9584.42 11896.7 178.0509898_MZ Hippuric acid Un 1.0 None None None None Hippuric acid is an acyl glycine formed by the conjugation of benzoic aicd with glycine. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction: acyl-CoA + glycine < -- > CoA + N-acylglycine. Hippuric acid is a normal component of urine and is typically increased with increased consumption of phenolic compounds (tea, wine, fruit juices). These phenols are converted to benzoic acid which is then converted to hippuric acid and excreted in the urine. Hippuric acid is the most frequently used biomarker in the biological monitoring of occupational exposure to toluene. This product of solvent biotransformation may be also found in the urine of individuals who have not been exposed to the solvent. A smaller fraction of the absorbed toluene is oxidized to aromatic compounds including ortho-cresol, which is not found significantly in the urine of nonexposed individuals. The concentration of hippuric acid in the urine of individuals exposed to a low toluene concentration does not differ from that of individuals not exposed to the solvent. This has led to the conclusion that hippuric acid should not be utilized in the biological monitoring of occupational exposure to low levels of toluene in the air. Protein-bound organic acids such as hippuric acid are markedly accumulated in uremic plasma and produce defective protein binding of drugs. (PMID: 9120876, 8734460). C9H9NO3, 3-Succinoylpyridine, Adrenochrome None None None 21723.9 16760.7 17809.8 19204.4 9683.16 10009.7 11490.9 25502.5 12482.3 10471.3 10646.5 48523.8 24458.2 8428.99 8212.97 13146.2 13947.7 30773.2 12305.1 17560.0 10057.5 11993.4 13864.1 10441.5 8871.28 11619.7 14155.6 17424.6 15240.8 16320.7 18603.1 9404.14 7194.49 22149.7 11897.8 11990.3 12437.8 8170.29 5056.24 14221.8 14837.1 9100.91 178.0719700_MZ Fructosamine Un 1.0 None None None None Fructosamine is a compound which can be considered as the result of a reaction between fructose and ammonia or an amine (with a molecule of water being released). A fructosamine is also formed when carbonyl group of glucose reacts with an amino group of a protein, as the double bond to oxygen moves from the end carbon atom to the next carbon atom and water is released. Fructosamines formed from blood proteins such as serum albumin are known as Glycated Serum Protein (GSP) or Glycated Albumin, and are used to identify the plasma glucose concentration over time and so assess diabetic control. (wikipedia). Glucose molecules are joined to protein molecules to form stable ketoamines, or fructosamines, through glycation, a nonenzymatic mechanism involving a labile Schiff base intermediate and the Amadori rearrangement. The amount of fructosamine in serum is increased in diabetes mellitus owing to the abnormally high concentration of sugar in blood. The concentration of fructosamine in serum thus reflects the degree of glycemic control attained by the diabetic patient and is useful in monitoring the effectiveness of therapy in diabetes over a period of several weeks, in a manner analogous to the determination of glycated hemoglobin. Of the analytical approaches used to measure fructosamine, affinity chromatography with m-aminophenylboronic acid and the nitroblue tetrazolium reduction method appear to be the most practical means for clinical chemists to assay fructosamine quickly, economically, and accurately. Fructosamine values can readily distinguish normal individuals and diabetic patients in good glycemic control from diabetics in poor control. Unlike glycated hemoglobin, which reflects the average blood sugar concentration over the past six to eight weeks, fructosamine reflects the average blood sugar concentration over the past two to three weeks. Thus a clinical advantage is that fructosamine responds more quickly to changes in therapy, thereby allowing for improved glycemic control. Fructosamine is used in conjunction with determinations of blood sugar and (or) of glycated hemoglobin, or by itself, the fructosamine assay can provide clinically useful information for the detection and control of diabetes. (PMID: 3319287). C6H13NO5, Glucosamine None None None 5566.03 4062.61 3054.97 3310.11 4672.52 4018.48 3645.34 3911.97 9006.73 3099.98 3154.11 4192.64 3166.89 4009.13 3540.11 4081.63 3456.45 3220.27 5298.25 3815.18 3375.0 2966.35 3705.79 3380.55 4861.66 3684.18 6615.26 3442.77 3727.49 4976.79 7997.71 5263.36 5619.27 5070.7 3087.63 6245.06 3071.23 2328.05 5032.94 3886.84 4409.66 2777.57 178.0862658_MZ (R)-Salsolinol Un 1.0 None None None None Salsolinol is an endogenous catechol isoquinoline detected in humans. Salsolinol was detected in urine of parkinsonian patients administered with L-DOPA. This finding stimulated the studies on Salsolinol derivatives in the brain, and gave new aspects of the endogenous alkaloids, which had been considered to occur only in plants. In normal non-alcoholic subjects and alcoholics, Salsolinol and O-methylated Salsolinol were found in urine, cerebrospinal fluid and brains. Salsolinol has an asymmetric center at first position and exists as (R)- and (S)enantiomer. The (R)enantiomer of Salsolinol is predominant in urine from healthy volunteers. Only the (R)enantiomers of Salsolinol and N-methylated Salsolinol occur in the human brain, cerebrospinal fluid (CSF) and intraventricular fluid (IVF), and the (S)enantiomers were not detected. (R)salsolinol synthase catalyzes the enantio-selective synthesis of (R)Salsolinol and 1-carboxyl(R)Salsolinol from dopamine with acetaldehyde or pyruvic acid. The N-methylation of (R)salsolinol into N-methylsalsolinol (NMSal) is catalyzed by two N-methyltransferases with different optimum pH, at pH 7.0 and 8.4. NM(R)Salsolinol is enzymatically oxidized into 1,2-dimethyl-6,7-dihydroxyisoquinolinium ion (DMDHIQ+) by an oxidase sensitive to semicarbaside and also non-enzymatically by autoxidation. NM(R)Salsolinol and its precursor, dopamine, were found to occur selectively in the nigro-striatum, whereas (R)Salsolinol distributes uniformly among the brain regions. (PMID 14697894). C10H13NO2, 2(N)-Methyl-norsalsolinol None None None 5649.59 5001.1 5263.32 5229.39 4959.08 5259.55 5003.57 5547.61 6136.02 5229.79 5273.97 5749.23 5404.31 5319.29 5263.09 5304.98 5636.23 5399.41 5545.39 5403.9 5190.07 5430.14 4952.17 5090.86 5236.71 4847.79 5821.77 5129.31 5518.58 5878.77 5244.73 4644.64 5637.84 5686.89 5323.24 5199.06 5019.44 5302.73 6044.31 5400.76 5176.18 5219.22 179.0463023_MZ Nicotinuric acid Un 1.0 None None None None Nicotinuric acid is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction:. acyl-CoA + glycine < -- > CoA + N-acylglycine. Nicotinuric acid is the major detoxification product of nicotinic acid. It may serve as a simple quantitative index of hepatic biotransformation of nicotinic acid.(PMID: 3243933). C8H8N2O3 None None None 44150.1 32463.8 26883.9 17918.3 25951.1 36952.3 37366.3 33002.9 15188.8 20852.9 22237.3 12458.6 51674.5 22457.4 19815.0 48860.7 24511.8 52904.8 29220.6 40647.8 41777.3 11466.4 26597.9 32474.5 33188.5 17842.8 35653.5 30586.5 18437.0 24440.5 40994.9 30701.0 15865.5 22906.6 16039.1 28868.1 19730.9 12886.4 19607.2 24462.9 43872.1 38593.9 179.0559938_MZ D-Glucose Un 1.0 None None None None Glucose is a monosaccharide containing six carbon atoms and an aldehyde group and is therefore referred to as an aldohexose. The glucose molecule can exist in an open-chain (acyclic) and ring (cyclic) form, the latter being the result of an intramolecular reaction between the aldehyde C atom and the C-5 hydroxyl group to form an intramolecular hemiacetal. In water solution both forms are in equilibrium and at pH 7 the cyclic one is the predominant. Glucose is a primary source of energy for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. In animals glucose arises from the breakdown of glycogen in a process known as glycogenolysis. Glucose is synthesized in the liver and kidneys from non-carbohydrate intermediates, such as pyruvate and glycerol, by a process known as gluconeogenesis. C6H12O6, D-Galactose, D-Mannose, Myoinositol, 3-Deoxyarabinohexonic acid, Beta-D-Glucose, D-Fructose, Allose, L-Sorbose, Alpha-D-Glucose, Beta-D-Galactose None None None 394617.0 356028.0 419557.0 301400.0 355532.0 487091.0 390512.0 373900.0 402089.0 359281.0 344790.0 430650.0 392673.0 377841.0 376431.0 437917.0 337462.0 392082.0 402514.0 411676.0 457216.0 452996.0 451088.0 392034.0 356233.0 356041.0 476538.0 404976.0 433858.0 414515.0 338516.0 394828.0 328971.0 326635.0 489375.0 442423.0 361636.0 457564.0 263752.0 471652.0 338422.0 348193.0 180.0666970_MZ L-Tyrosine Un 1.0 None None None None Tyrosine is an essential amino acid that readily passes the blood-brain barrier. Once in the brain, it is a precursor for the neurotransmitters dopamine, norepinephrine and epinephrine, better known as adrenalin. These neurotransmitters are an important part of the body's sympathetic nervous system, and their concentrations in the body and brain are directly dependent upon dietary tyrosine. Tyrosine is not found in large concentrations throughout the body, probably because it is rapidly metabolized. Folic acid, copper and vitamin C are cofactor nutrients of these reactions. Tyrosine is also the precursor for hormones, thyroid, catecholestrogens and the major human pigment, melanin. Tyrosine is an important amino acid in many proteins, peptides and even enkephalins, the body's natural pain reliever. Valine and other branched amino acids, and possibly tryptophan and phenylalanine may reduce tyrosine absorption. A number of genetic errors of tyrosine metabolism occur. Most common is the increased amount of tyrosine in the blood of premature infants, which is marked by decreased motor activity, lethargy and poor feeding. Infection and intellectual deficits may occur. Vitamin C supplements reverse the disease. Some adults also develop elevated tyrosine in their blood. This indicates a need for more vitamin C. More tyrosine is needed under stress, and tyrosine supplements prevent the stress-induced depletion of norepinephrine and can cure biochemical depression. However, tyrosine may not be good for psychosis. Many antipsychotic medications apparently function by inhibiting tyrosine metabolism. L-dopa, which is directly used in Parkinson's, is made from tyrosine. Tyrosine, the nutrient, can be used as an adjunct in the treatment of Parkinson's. Peripheral metabolism of tyrosine necessitates large doses of tyrosine, however, compared to L-dopa. (http://www.dcnutrition.com). C9H11NO3, 4-Hydroxy-4-(3-pyridyl)-butanoic acid, L-Threo-3-Phenylserine, Beta-Tyrosine, o-Tyrosine None None None 190014.0 175133.0 171171.0 73883.6 134654.0 236821.0 137104.0 141911.0 136517.0 150301.0 127425.0 172813.0 182408.0 161384.0 152019.0 209004.0 121609.0 168602.0 159938.0 181402.0 156985.0 162919.0 142838.0 150053.0 128717.0 120537.0 160485.0 154215.0 198948.0 180079.0 108617.0 134047.0 141539.0 109423.0 208804.0 165528.0 126122.0 160994.0 98100.9 159282.0 113505.0 124767.0 180.1035825_MZ L-Carnitine Un 1.0 None None None None Carnitine is not an essential amino acid; it can be synthesized in the body. However, it is so important in providing energy to muscles including the heart-that some researchers are now recommending carnitine supplements in the diet, particularly for people who do not consume much red meat, the main food source for carnitine. Carnitine has been described as a vitamin, an amino acid, or a metabimin, i.e., an essential metabolite. Like the B vitamins, carnitine contains nitrogen and is very soluble in water, and to some researchers carnitine is a vitamin (Liebovitz 1984). It was found that an animal (yellow mealworm) could not grow without carnitine in its diet. However, as it turned out, almost all other animals, including humans, do make their own carnitine; thus, it is no longer considered a vitamin. Nevertheless, in certain circumstances-such as deficiencies of methionine, lysine or vitamin C or kidney dialysis--carnitine shortages develop. Under these conditions, carnitine must be absorbed from food, and for this reason it is sometimes referred to as a metabimin or a conditionally essential metabolite. Like the other amino acids used or manufactured by the body, carnitine is an amine. But like choline, which is sometimes considered to be a B vitamin, carnitine is also an alcohol (specifically, a trimethylated carboxy-alcohol). Thus, carnitine is an unusual amino acid and has different functions than most other amino acids, which are most usually employed by the body in the construction of protein. Carnitine is an essential factor in fatty acid metabolism in mammals. It's most important known metabolic function is to transport fat into the mitochondria of muscle cells, including those in the heart, for oxidation. This is how the heart gets most of its energy. In humans, about 25% of carnitine is synthesized in the liver, kidney and brain from the amino acids lysine and methionine. Most of the carnitine in the body comes from dietary sources such as red meat and dairy products. Inborn errors of carnitine metabolism can lead to brain deterioration like that of Reye's syndrome, gradually worsening muscle weakness, Duchenne-like muscular dystrophy and extreme muscle weakness with fat accumulation in muscles. Borurn et al. (1979) describe carnitine as an essential nutrient for pre-term babies, certain types (non-ketotic) of hypoglycemics, kidney dialysis patients, cirrhosis, and in kwashiorkor, type IV hyperlipidemia, heart muscle disease (cardiomyopathy), and propionic or organic aciduria (acid urine resulting from genetic or other anomalies). In all these conditions and the inborn errors of carnitine metabolism, carnitine is essential to life and carnitine supplements are valuable. carnitine therapy may also be useful in a wide variety of clinical conditions. carnitine supplementation has improved some patients who have angina secondary to coronary artery disease. It may be worth a trial in any form of hyperlipidemia or muscle weakness. carnitine supplements may be useful in many forms of toxic or metabolic liver disease and in cases of heart muscle disease. Hearts undergoing severe arrhythmia quickly deplete their stores of carnitine. Athletes, particularly in Europe, have used carnitine supplements for improved endurance. carnitine may improve muscle building by improving fat utilization and may even be useful in treating obesity. carnitine joins a long list of nutrients which may be of value in treating pregnant women, hypothyroid individuals, and male infertility due to low motility of sperm. Even the Physician's Desk Reference gives indication for carnitine supplements as improving the tolerance of ischemic heart disease, myocardial insufficiencies, and type IV hyperlipoproteinemia. carnitine deficiency is noted in abnormal liver function, renal dialysis patients, and severe to moderate muscular weakness with associated anorexia. (http://www.dcnutrition.com). C7H15NO3 None None None 4930.53 4801.46 5081.02 4492.59 4784.57 4985.26 4299.33 5171.67 4924.41 4511.64 4566.54 4867.74 5166.92 4863.35 4778.8 4560.8 4443.31 5273.69 4270.75 4901.25 5140.37 4887.31 4847.27 4893.67 4191.04 4205.22 4600.42 4716.13 4989.51 5179.61 3567.11 3761.44 4905.68 4166.53 5601.51 4771.57 4037.01 4757.49 4057.47 4697.07 3992.81 4116.81 181.0515113_MZ Homovanillic acid Un 1.0 None None None None Homovanillic acid is a dopamine metabolite occurring in human biofluids. A high proportion of patients with neuroblastoma excrete increased amounts of it in their urine. Homovanillic acid is a major catecholamine metabolite. It is used as a reagent to detect oxidative enzymes.(Wikipedia). C9H10O4, Isohomovanillic acid, 3,4-Dihydroxyhydrocinnamic acid, Hydroxyphenyllactic acid, 3-(3-hydroxyphenyl)-3-hydroxypropanoic acid, 3-Methoxy-4-hydroxyphenylglycolaldehyde None None None 40197.4 40190.5 36098.9 35827.9 36057.2 52458.9 38891.0 32560.8 34779.8 34964.9 34322.1 37829.7 25544.5 39065.0 31920.9 47798.1 33590.8 39243.0 32381.5 31630.6 35923.8 30978.1 35159.8 36206.1 33158.2 29926.1 37603.3 36136.4 33994.0 49294.5 32092.1 33027.2 34517.3 31632.5 31196.7 41098.9 32020.1 30945.7 24359.1 32326.8 26951.8 31036.8 181.0713942_MZ Sorbitol Un 1.0 None None None None Sorbitol is a polyhydric alcohol with about half the sweetness of sucrose. Sorbitol occurs naturally and is also produced synthetically from glucose. It was formerly used as a diuretic and may still be used as a laxative and in irrigating solutions for some surgical procedures. It is also used in many manufacturing processes, as a pharmaceutical aid, and in several research applications. Ascorbic acid fermentation; in solution form for moisture-conditioning of cosmetic creams and lotions, toothpaste, tobacco, gelatin; bodying agent for paper, textiles, and liquid pharmaceuticals; softener for candy; sugar crystallization inhibitor; surfactants; urethane resins and rigid foams; plasticizer, stabilizer for vinyl resins; food additive (sweetener, humectant, emulsifier, thickener, anticaking agent); dietary supplement. (Hawley's Condensed Chemical Dictionary) Biological Source: Occurs widely in plants ranging from algae to the higher orders. Fruits of the plant family Rosaceae, which include apples, pears, cherries, apricots, contain appreciable amounts. Rich sources are the fruits of the Sorbus and Crataegus species Use/Importance: Used for manufacturing of sorbose, propylene glycol, ascorbic acid, resins, plasticizers and as antifreeze mixtures with glycerol or glycol. Tablet diluent, sweetening agent and humectant, other food uses. Sorbitol is used in photometric determination of Ru(VI) and Ru(VIII); in acid-base titration of borate (Dictionary of Organic Compounds). C6H14O6, Galactitol, Mannitol, L-Iditol None None None 45066.1 42602.2 47333.3 28192.8 43595.3 58177.4 37574.0 59805.0 39019.7 42930.5 36871.0 45849.3 43955.8 44886.2 43036.3 48046.8 39310.3 59654.2 49887.4 97802.2 40833.6 40100.4 41836.6 40271.3 38638.5 38496.8 41194.5 44094.5 44821.8 46850.1 68580.1 38336.4 37797.4 48705.0 45651.6 48286.3 37065.0 36135.6 30031.3 44233.7 76319.4 37862.3 182.0120396_MZ L-Homocysteic acid Un 1.0 None None None None Short-term incubation of lymphocytes with homocysteine or its oxidation product homocysteinic acid increased the formation of reactive oxygen species and cell necrosis. C4H9NO5S None None None 26906.8 24751.3 20078.0 31267.7 24056.9 25315.0 25858.8 31083.1 20266.9 27205.6 26423.9 14599.7 21610.7 32154.2 26074.6 21711.3 33532.7 26387.6 26611.9 28906.2 27719.8 15789.2 23606.0 29192.5 21993.7 13869.4 23134.6 19906.3 13586.2 29600.0 27627.7 23043.8 13230.7 26095.8 15732.1 25935.8 18967.4 15496.5 18905.8 27254.9 29241.8 27604.0 182.0446311_MZ 4-Pyridoxic acid Un 1.0 None None None None 4-Pyridoxic acid is the catabolic product of vitamin B6 (also known as pyridoxine, pyridoxal and pyradoxamine) which is excreted in the urine. Urinary levels of 4-pyridoxic acid are lower in females than in males and will be reduced in persons with riboflavin deficiency. 4-Pyridoxic acid is formed by the action of aldehyde oxidase I (an endogenous enzyme) and by microbial enzymes (pyridoxal 4-dehydrogenase), an NAD-dependent aldehyde dehydrogenase. 4-pyridoxic acid can be further broken down by the gut microflora via 4-pyridoxic acid dehydrogenase. This enzyme catalyzes the four electron oxidation of 4-pyridoxic acid to 3-hydroxy-2-methylpyridine-4,5-dicarboxylate, using nicotinamide adenine dinucleotide as a cofactor. C8H9NO4 None None None 26640.0 14756.4 16992.1 8858.96 16180.3 22498.7 15107.2 14679.2 14470.8 15644.3 13265.3 17888.9 14119.8 13145.5 15688.2 24119.5 10417.0 26914.3 13895.0 22197.6 15046.6 15707.7 16103.3 13764.7 16609.8 14073.2 10792.1 18593.9 19220.8 23086.4 18538.6 14847.4 12261.5 14094.1 16951.7 13250.8 11628.9 14354.9 12665.4 16865.3 14583.4 13306.3 182.9704421_MZ Phosphohydroxypyruvic acid Un 1.0 None None None None Phosphohydroxypyruvic acid is a prduct of both enzyme phosphoglycerate dehydrogenase [EC 1.1.1.95] and phosphoserine transaminase [EC 2.6.1.52] in glycine, serine and threonine metabolism pathway (KEGG). C3H5O7P None None None 14102.2 13128.7 13385.3 18541.9 13098.5 17805.1 13617.8 10430.3 13698.7 18525.2 14071.6 13119.9 20806.9 14209.9 15689.0 21088.6 11519.7 20835.0 17601.6 16248.4 12457.9 15800.7 14929.1 13547.5 15720.1 13314.4 13219.5 16431.7 14584.7 15058.6 14402.7 22610.7 16367.5 14444.5 14291.5 17222.4 14112.1 14148.8 12944.1 16265.2 17296.7 14781.1 183.0663014_MZ Phosphorylcholine Un 1.0 None None None None Phosphorylcholine is a small haptenic molecule, is found in a wide variety of organisms. Human hepatic tumors undergo an elevation in the concentration of phosphorylcholine as the principal metabolic change is observed (PMID: 11076016). Phosphorylcholine is the precursor metabolite of choline in the glycine, serine and threonine metabolism pathways (KEGG, map00260) and in intermediate between choline and cytidine-diphosphate choline in the glycerophospholipid metabolism pathway (KEGG, map00564). C5H15NO4P, Vanylglycol None None None 11958.0 13984.5 14917.3 13389.4 16558.7 13785.2 13291.5 15881.5 12220.6 12723.9 15306.3 13821.4 9376.97 14934.4 16668.3 13806.0 20639.1 8846.13 10799.2 10947.8 11486.0 11909.4 12414.1 12919.0 12554.4 10625.7 14020.5 12080.5 10657.1 14322.1 9814.47 10370.3 11904.3 11136.0 11387.9 11233.8 10719.2 11821.0 8675.36 13811.7 7769.09 10998.8 184.0017390_MZ Phosphoserine Un 1.0 None None None None The phosphoric acid ester of serine. As a constituent (residue) of proteins, its side chain can undergo O-linked glycosylation. This might be important in explaining some of the devastating consequences of diabetes. It is one of three amino acid residues that are commonly phosphorylated by kinases during cell signalling in eukaryotes. Phosphorylated serine residues are often referred to as phosphoserine. Serine proteases are a common type of protease. Serine, organic compound, one of the 20 amino acids commonly found in animal proteins. Only the L-stereoisomer appears in mammalian protein. It is not essential to the human diet, since it can be synthesized in the body from other metabolites, including glycine. Serine was first obtained from silk protein, a particularly rich source, in 1865. Its name is derived from the Latin for silk, sericum. Serine's structure was established in 1902. C3H8NO6P, DL-O-Phosphoserine None None None 162460.0 167757.0 175831.0 100726.0 150874.0 82552.7 125008.0 293153.0 120480.0 100974.0 162575.0 143045.0 134303.0 182424.0 170601.0 64950.8 163482.0 152906.0 100603.0 103392.0 157551.0 142331.0 126301.0 153795.0 167486.0 131102.0 121435.0 136891.0 202573.0 119176.0 133134.0 95940.3 145565.0 89478.3 209330.0 109899.0 130498.0 170847.0 146501.0 182363.0 164337.0 139205.0 184.0979742_MZ Pseudoecgonine Un 1.0 None None None None Pseudoecgonine is a metabolic byproduct of cocaine. Cocaine is extensively metabolized in the liver, with only about 1% excreted unchanged in the urine. The metabolism is dominated by hydrolytic ester cleavage, so the eliminated metabolites consist mostly of benzoylecgonine, the major metabolite, and in lesser amounts ecgonine methyl ester and ecgonine. Pseudoecgonine is a steroisomer of ecgonine and may be conjugated to CoA to form Pseudoecgonyl-CoA through the action of gut microlfora (PMID: 8572717). C9H15NO3, Ecgonine None None None 4977.61 4331.99 4795.49 5755.85 4512.17 5199.4 5683.03 4894.38 4004.5 4041.44 4586.89 4069.15 3905.8 4596.32 4274.48 5274.73 4822.24 4110.02 4441.62 3949.51 3971.88 4115.71 5913.98 5195.0 4361.06 4166.63 4396.74 4544.15 4006.2 5387.41 4324.84 4355.44 3759.7 4148.8 3874.73 4739.67 3960.35 3830.07 2999.5 4631.7 3701.41 3954.49 184.9857957_MZ 2-Phosphoglyceric acid Un 1.0 None None None None 2-Phosphoglyceric acid (2PGA) is a glyceric acid which serves as the substrate in the ninth step of glycolysis. It is catalyzed by enolase into phosphoenolpyruvate (PEP), the penultimate step in the conversion of glucose to pyruvate. Enolase catalyzes the beta-elimination reaction in a stepwise manner wherein OH- is eliminated from C3 of a discrete carbanion (enolate) intermediate. This intermediate is created by removal of the proton from C2 of 2PGA by a base in the active site. (PMID: 8994873, Wikipedia). C3H7O7P, 3-Phosphoglyceric acid, 2-Phospho-D-glyceric acid None None None 19003.9 25638.9 19184.1 11715.8 25891.0 18668.8 24727.6 23042.2 24343.7 17953.5 19758.6 22428.1 13054.4 22199.9 22939.9 19698.7 31708.1 13149.4 18311.8 21090.5 18245.0 19140.6 16957.1 16249.3 23928.3 15592.9 26976.6 16345.1 12111.7 18737.3 30240.5 21659.6 17527.1 23229.7 17874.0 13421.8 22482.4 21907.3 10875.6 15706.1 16251.4 14836.1 185.1182547_MZ 3-Oxodecanoic acid Un 1.0 None None None None In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. 3-Oxodecanoic acid is an intermediate in fatty acid biosynthesis. Specifically, 3-Oxodecanoic acid is converted from Malonic acid via three enzymes; 3-oxoacyl-[acyl-carrier-protein] synthase, fatty-acid Synthase and beta-ketoacyl -acyl-carrier-protein synthase II. (EC:2.3.1.41, E.C: 2.3.1.85, 2.3.1.179). C10H18O3 None None None 18468.2 18382.5 21002.5 18721.5 18550.3 18216.8 20447.7 27216.8 14648.9 17224.9 18880.3 15173.6 12825.6 17919.1 20707.8 17344.6 32534.2 16475.3 15311.9 18726.2 17657.4 13956.0 17794.7 18881.7 16875.7 14827.9 19170.8 16665.7 14460.1 20056.5 15652.0 14801.2 13951.6 16269.0 15524.7 17984.9 13988.7 14198.6 14783.2 17793.5 13533.1 16244.4 185.1546716_MZ 4,6-Dimethylnonanoic acid Un 1.0 None None None None 4,6-Dimethylnonanoic acid is produced in the peroxisomes from pristanic acid (where undergoes three cycles of β-oxidation) and then exported to the mitochondria or hydrolyzed by an acyl-CoA thioesterase and transported to the mitochondrion, followed by reactivation to its CoA-ester inside the mitochondria for full oxidation to CO2 and H2O. (PMID: 11785945). C11H22O2, Undecanoic acid None None None 29868.0 29545.3 26980.1 22490.3 25338.2 31372.0 30748.4 36712.5 21672.2 25498.4 22382.3 20799.8 23451.5 29889.5 26658.9 23299.9 46074.2 29063.8 26121.4 30433.3 26534.9 20298.2 26785.7 34040.4 21340.4 18617.5 24990.6 24823.2 18777.3 30935.2 23625.3 20936.5 18559.5 25049.6 21884.9 26183.4 20458.8 18530.9 23577.5 27270.3 20089.9 24695.1 186.0771354_MZ 2-Keto-6-acetamidocaproate Un 1.0 None None None None 2-Keto-6-acetamidocaproate is an intermediate in lysine degradation. It can be generated from N6-acetyl-L-lysine. N-acetyl-lysine is an acetylated amino acid. Post-translational lysine-acetylation is one of two major modifications of lysine residues in various proteins. Acetylation of specific lysine residues in the N-terminal domains of core histones is a biochemical marker of active genes. Acetylation is now known to play a major role in eukaryotic transcription. Specifically, acetyltransferase enzymes that act on particular lysine side chains of histones and other proteins are intimately involved in transcriptional activation. N6-acetyl-L-lysine can be converted to 2-Keto-6-acetamidocaproate via the enzyme N6-acetyllysine aminotransferase and then 2-keto-6-acetamidocaproate can be reduced enzymatically to 5-acetamidovalerate. C8H13NO4 None None None 6432.07 5434.59 6371.38 9936.92 5110.21 6063.18 7342.86 7446.83 5281.15 5494.83 5869.94 8770.56 5019.81 4794.76 4672.52 6091.14 7717.48 5605.15 4766.22 5504.23 5340.18 4503.72 5945.12 5837.81 4753.69 4434.18 5853.63 6510.15 4665.12 6703.81 5801.6 5042.25 3539.65 5806.04 4662.01 5635.23 5024.57 4947.37 3547.79 5669.55 4911.84 5188.06 186.1135939_MZ N-Heptanoylglycine Un 1.0 None None None None N-Heptanoylglycine is an acylglycine with C-7 fatty acid group as the acyl moiety. Acylglycines 1 possess a common amidoacetic acid moiety and are normally minor metabolites of fatty acids. Elevated levels of certain acylglycines appear in the urine and blood of patients with various fatty acid oxidation disorders. They are normally produced through the action of glycine N-acyltransferase which is an enzyme that catalyzes the chemical reaction: acyl-CoA + glycine ↔ CoA + N-acylglycine. C9H17NO3 None None None 15348.8 15131.5 13819.8 17921.0 9200.82 11379.1 21993.5 17314.1 10908.3 11083.8 10289.0 7503.47 14132.5 13343.1 10715.8 9707.92 22790.3 17310.4 11406.2 15208.5 11853.5 6366.04 11125.5 17562.3 11397.2 8029.5 9098.48 12922.4 6914.08 16526.3 14734.4 9393.85 6118.28 16316.5 7242.47 16180.5 10702.4 6526.38 7800.08 14931.4 19983.1 12850.1 187.0071900_MZ p-Cresol sulfate Un 1.0 None None None None p-Cresol sulfate is a microbial metabolite that is found in urine and likely derives from secondary metabolism of p-cresol. It appears to be elevated in the urine of individuals with progressive multiple sclerosis (PMID: 10775436). p-Cresol sulfate is the major component of urinary MBPLM (myelin basic protein-like material). p-Cresol sulfate is a small protein-bound molecule that is poorly cleared with dialysis and is often considered to be a uremic toxin. Uremic toxins include low-molecular-weight compounds such as indoxyl sulfate, p-cresol sulfate, 3-carboxy-4-methyl-5-propyl-2-furanpropionic acid and asymmetric dimethylarginine (PMID: 18941347). It has also been linked to cardiovascular disease and oxidative injury. C7H8O4S None None None 20359.1 18205.9 20800.9 17219.2 19853.9 28089.7 4308.08 24635.5 16930.6 8280.86 4245.09 26679.8 17109.6 15518.0 36942.0 25698.3 4429.94 19371.2 6018.41 13336.6 4194.81 21177.5 21426.1 16118.0 6996.69 17630.1 18175.3 13398.6 41386.1 17656.4 46915.6 8236.56 16821.0 13345.2 27526.4 5875.83 14599.9 3959.16 20521.2 31724.8 14907.5 11883.5 187.0723352_MZ N-Acetylglutamine Un 1.0 None None None None N-Acetylglutamine (GIcNAc) is a modified amino acid (an acetylated analogue of glutamine), a metabolite present in normal human urine. The decomposition products of GIcNAc have been identified by NMR and HPLC-MS as N-acetyl-L-glutamic acid, N-(2,6-dioxo-3-piperidinyl) acetamide, pyroglutamic acid, glutamic acid, and glutamine. GIcNAc is used for parenteral nutrition as a source of glutamine, since glutamine is too unstable, but GIcNAc is very stable. In patients treated with aminoglycosides and/or glycopeptides, elevation GIcNAc in urine suggests renal tubular injury. High amounts of N-acetylated amino acids (i.e.: N-Acetylglutamine) were detected patient with aminoacylase I deficiency (EC 3.5.1.14, a homodimeric zinc-binding metalloenzyme located in the cytosol), a novel inborn error of metabolism. (PMID: 15331932, 11312773, 7952062, 2569664, 16274666). C7H12N2O4, L-glycyl-L-hydroxyproline None None None 256963.0 245873.0 268463.0 396594.0 372140.0 214097.0 120072.0 240143.0 286367.0 225231.0 301979.0 353737.0 220444.0 244428.0 234258.0 434693.0 204181.0 144854.0 188411.0 147119.0 228082.0 259931.0 174814.0 193880.0 217674.0 214090.0 182534.0 210768.0 294420.0 159190.0 210699.0 356730.0 222666.0 208941.0 202656.0 369751.0 150309.0 289403.0 141079.0 200726.0 193939.0 165560.0 187.0976612_MZ Nonate Un 1.0 None None None None Nonic acid or the anion, nonate, is a derivative of succinic acid, which is a dicarboxylic acid. The anion, succinate, is a component of the citric acid cycle capable of donating electrons to the electron transfer chain. Succinate dehydrogenase (SDH) plays an important role in the mitochondria, being both part of the respiratory chain and the Krebs cycle. SDH with a covalently attached FAD prosthetic group, binds enzyme substrates (succinate and fumarate) and physiological regulators (oxaloacetate and ATP). Oxidizing succinate links SDH to the fast-cycling Krebs cycle portion where it participates in the breakdown of acetyl-CoA throughout the whole Krebs cycle. The succinate can readily be imported into the mitochondrial matrix by the n-butylmalonate- (or phenylsuccinate-) sensitive dicarboxylate carrier in exchange with inorganic phosphate or another organic acid, e. g. malate. (PMID 16143825) Mutations in the four genes encoding the subunits of the mitochondrial respiratory chain succinate dehydrogenase are associated with a wide spectrum of clinical presentations (i.e.: Huntington's disease. (PMID 11803021). C9H16O4, Azelaic acid None None None 161578.0 159265.0 59376.1 185190.0 66688.4 89927.8 56506.3 72149.8 102491.0 91265.4 89784.8 50938.2 43101.3 123259.0 73636.6 68020.5 74369.9 39250.0 62648.2 48111.6 140835.0 51338.6 84730.4 200254.0 86144.6 49307.1 55828.7 52579.1 46593.4 172375.0 48398.4 74177.7 43432.9 98980.4 53557.1 175116.0 93326.3 47990.4 45365.3 144458.0 46023.7 112150.0 188.0002991_MZ Lanthionine ketimine Un 1.0 None None None None Lanthionine ketimine binds specifically and with high affinity to brain membranes and belong to a class of endogenous sulfur-containing cyclic products provided with a possible neurochemical function (PMID 1761027). C6H7NO4S None None None 26423.0 19481.8 27346.7 25481.2 20618.7 30593.4 11581.7 15328.0 41902.7 28830.6 36390.0 30937.7 13334.2 25451.3 21821.0 20898.4 21697.4 24825.5 17056.3 17747.2 27652.6 41736.2 26489.1 33616.9 16059.5 23862.8 16280.0 26613.7 32990.1 24234.1 13093.4 17699.8 47086.9 24332.9 44586.3 61613.4 28312.2 32182.0 12567.1 44530.5 6969.08 25690.2 188.0564272_MZ Glutarylglycine Un 1.0 None None None None Glutarylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction:. acyl-CoA + glycine < -- > CoA + N-acylglycine. Glutarylglycine is involved in lysine metabolism. An elevated level of glutarylglycine occurs in patients with glutaric acidemia type II, which is an autosomal recessive inborn error of metabolism due to a mitochondrial respiratory electron chain transport defect. (http://www.pediatricneuro.com/alfonso/pg75.htm). C7H11NO5, N-Acetylglutamic acid None None None 761038.0 677638.0 802293.0 871859.0 1216520.0 614961.0 818580.0 537578.0 965512.0 696576.0 720727.0 594996.0 713284.0 815538.0 1028080.0 868634.0 1327530.0 847159.0 501702.0 439287.0 661598.0 476716.0 819711.0 544774.0 949417.0 366895.0 696512.0 790186.0 988722.0 615357.0 670074.0 975492.0 508869.0 385758.0 895605.0 655860.0 501952.0 875288.0 453306.0 719491.0 793954.0 521426.0 189.0404287_MZ 3-Dehydroquinate Un 1.0 None None None None In most organisms, 3-dehydroquinate is synthesized from D-erythrose-4-phosphate in two steps. However, the genomes of the archaea contain no orthologs for the genes that encode these first two steps. Instead, archaeabacteria appear to utilize an alternative pathway in which 3-dehydroquinate is synthesized from 6-deoxy-5-ketofructose-1-phosphate and L-aspartate-semialdehyde. These two compounds are first condensed to form 2-amino-3,7-dideoxy-D-threo-hept-6-ulosonate, which cyclizes to 3-dehydroquinate. From 3-dehydroquinate and on to chorismate, the archaeal pathway appears to be identical to the bacterial pathway. C7H10O6 None None None 53692.5 57963.7 49775.4 101518.0 52287.8 52205.3 48982.3 62646.0 35396.4 49070.5 56466.2 36982.8 44030.1 68804.7 60707.1 65915.8 58490.8 50967.1 36508.8 34909.9 67983.7 30592.7 43015.7 50007.6 55932.8 38835.6 55779.3 32627.3 41837.2 66121.4 57839.9 65893.1 43010.4 38245.4 61217.8 54506.7 38121.6 31993.8 44276.6 43556.0 42718.6 57024.7 189.0760509_MZ 3-Hydroxysuberic acid Un 1.0 None None None None 3-Hydroxysuberic acid is a metabolite derived from the w-oxidation of 3-hydroxy fatty acids and the subsequent beta-oxidation of longer-chain 3-hydroxy dicarboxylic acids (PMID 2001377). It has been found increased in ketoaciduria (PMID 1591279). C8H14O5 None None None 19575.0 18386.0 19353.7 26145.9 22618.2 17431.6 17304.7 18268.2 17683.1 17001.8 18389.2 16729.5 13828.9 18848.8 21458.1 21365.3 27334.7 14729.4 13685.7 13140.1 16906.9 12755.4 17783.7 15950.5 17650.1 11613.3 17646.5 15783.4 16160.5 19682.8 16076.9 19437.2 11797.4 13709.5 16710.6 17212.0 12049.9 15790.1 12122.7 16862.9 13665.6 13811.3 190.0540451_MZ N-Acetyl-L-methionine Un 1.0 None None None None N-acetyl-L-methionine is nutritionally and metabolically equivalent to L-methionine. Methionine is a dietary indispensable amino acid required for normal growth and development of humans, other mammals, and avian species. In addition to being a substrate for protein synthesis, it is an intermediate in transmethylation reactions, serving as the major methyl group donor in vivo, including the methyl groups for DNA and RNA intermediates. Methionine is a methyl acceptor for 5-methyltetrahydrofolate-homocysteine methyl transferase (methionine synthase), the only reaction that allows for the recycling of this form of folate, and is also a methyl acceptor for the catabolism of betaine. Methionine is also required for synthesis of cysteine. Methionine is accepted as the metabolic precursor for cysteine. Only the sulfur atom from methionine is transferred to cysteine; the carbon skeleton of cysteine is donated by serine. (PMID 16702340). The adequacy range of dietary requirements of specific amino acids in disease states is difficult to determine. Requirements may not be similar in disease with regard to protein synthesis. Requirements for this purpose can be assessed only when such a function can be measured and related to clinical outcome. There is apparent consensus concerning normal sulfur amino acid (SAA) requirements. WHO recommendations amount to 13 mg/kg per 24 h in healthy adults. This amount is roughly doubled in artificial nutrition regimens. In disease or after trauma, requirements may be altered for methionine, cysteine, and taurine. Although in specific cases of congenital enzyme deficiency, prematurity, or diminished liver function, hypermethionemia or hyperhomocysteinemia may occur, SAA supplementation can be considered safe in amounts exceeding 2-3 times the minimal recommended daily intake. Apart from some very specific indications (e.g., acetaminophen poisoning) the usefulness of SAA supplementation is not yet established.(PMID 16702341). Methionine is known to exacerbate psychopathological symptoms in schizophrenic patients, there is no evidence of similar effects in healthy subjects. The role of methionine as a precursor of homocysteine is the most notable cause for concern. A loading dose of methionine (0.1 g/kg) has been given, and the resultant acute increase in plasma homocysteine has been used as an index of the susceptibility to cardiovascular disease. Although this procedure results in vascular dysfunction, this is acute and unlikely to result in permanent damage. However, a 10-fold larger dose, given mistakenly, resulted in death. Longer-term studies in adults have indicated no adverse consequences of moderate fluctuations in dietary methionine intake, but intakes higher than 5 times normal resulted in elevated homocysteine levels. These effects of methionine on homocysteine and vascular function are moderated by supplements of vitamins B-6, B-12, C, and folic acid. In infants, methionine intakes of 2 to 5 times normal resulted in impaired growth and extremely high plasma methionine levels, but no adverse long-term consequences were observed. (PMID 16702346). C7H13NO3S None None None 19092.5 11968.4 16745.4 14049.3 16251.4 12362.7 11427.8 11175.3 14943.4 12700.6 11303.0 20262.7 17213.9 21645.7 10623.0 20638.7 11269.6 14710.0 9149.73 11187.6 11301.1 13724.0 10210.1 10432.8 12974.0 11418.9 10600.9 14688.2 15797.5 12831.4 11181.3 14962.6 14462.6 10859.7 12082.2 15371.6 9766.82 12650.4 7768.48 10155.9 11904.6 10107.2 190.0887455_MZ 5-Methoxytryptophol Un 1.0 None None None None 5-Methoxytryptophol is synthesized by the pineal gland. Daily rhythms in pineal methoxyindole metabolism have been described in rodents and humans (5-Methoxytryptophol levels are coincident with serotonin levels in rodents pineal) and 5-Methoxytryptophol at its highest during the daylight hours and fall markedly soon after the onset of darkness, coincident with increases in the levels of pineal melatonin and the activities of pineal serotonin-N-acetyltransferase (EC 2.3.1.87, SNAT) and hydroxyindole-O-methyltransferase (EC 2.1.1.4, HIOMT). The fact that the levels of 5-methoxytryptophol and melatonin vary in parallel suggests that the major factor generating the methoxyindole rhythms is not SNAT activity, but perhaps a change in the availability (for metabolism) of stored serotonin. When the onset of darkness is delayed by 12 hours, human 5-methoxytryptophol (and melatonin) rhythms usually require 3 or 4 days to adjust to the new lighting regimen. Environmental factors, other than light, that activate the sympathetic nervous system or cause epinephrine to be secreted from the adrenal medulla (e.g., the stress of immobilization; insulin-induced hypoglycemia) can override the inhibitory effects of light and accelerate melatonin synthesis. Rhythms in 5-methoxytryptophol (and melatonin) synthesis apparently persist among animals placed in environments of continuous darkness; the source of the cyclic signal (mediated by the pineal sympathetic nerves) has not yet been identified. Preliminary evidence suggests that levels of a peptide hormone, arginine vasotocin, in rat pineal and sera also exhibit daily rhythms and are increased by norepinephrine. The circadian rhythm of melatonin secretion is generated in the suprachiasmatic nucleus. Sleep disruption, nightly restlessness, sundowning, and other circadian disturbances are frequently seen in Alzheimer's disease patients. Changes in the suprachiasmatic nucleus and pineal gland are thought to be the biological basis for these behavioral disturbances. (PMID 288858, 2245336). C11H13NO2 None None None 2789.4 2554.89 2767.08 3006.62 3082.55 2823.5 2597.16 2709.72 3515.29 2493.16 2791.74 2974.4 2100.88 2769.67 2868.31 3347.04 2927.99 2198.36 2212.76 2393.93 2614.33 2757.17 2739.35 2506.5 2587.31 2507.28 2497.05 2627.56 2928.91 2946.86 2845.89 2820.22 2805.15 2347.22 2913.48 2741.46 2314.93 2698.52 2008.48 2692.16 2214.41 2397.24 191.0198938_MZ Citric acid Un 1.0 None None None None Citric acid (citrate) is a weak acid that is formed in the tricarboxylic acid cycle or that may be introduced with diet. The evaluation of plasma citric acid is scarcely used in the diagnosis of human diseases. On the contrary urinary citrate excretion is a common tool in the differential diagnosis of kidney stones, renal tubular acidosis and it plays also a role in bone diseases. The importance of hypocitraturia should be considered with regard to bone mass, urine crystallization and urolithiasis. (PMID 12957820) The secretory epithelial cells of the prostate gland of humans and other animals posses a unique citrate-related metabolic pathway regulated by testosterone and prolactin. This specialized hormone-regulated metabolic activity is responsible for the major prostate function of the production and secretion of extraordinarily high levels of citrate. The key regulatory enzymes directly associated with citrate production in the prostate cells are mitochondrial aspartate aminotransferase, pyruvate dehydrogenase, and mitochondrial aconitase. testosterone and prolactin are involved in the regulation of the corresponding genes associated with these enzymes. The regulatory regions of these genes contain the necessary response elements that confer the ability of both hormones to control gene transcription. Protein kinase c (PKC) is the signaling pathway for the prolactin regulation of the metabolic genes in prostate cells. testosterone and prolactin regulation of these metabolic genes (which are constitutively expressed in all mammalian cells) is specific for these citrate-producing cells. (PMID 12198595) Citric acid is found in citrus fruits, most concentrated in lemons and limes, where it can comprise as much as 8% of the dry weight of the fruit. Citric acid is a natural preservative and is also used to add an acidic (sour) taste to foods and soft drinks. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability. Intolerance to citric acid in the diet is known to exist. Little information is available as the condition appears to be rare, but like other types of food intolerance it is often described as a pseudo-allergic reaction. C6H8O7, Isocitric acid, D-threo-Isocitric acid, Diketogulonic acid, 2,3-Diketo-L-gulonate None None None 535214.0 486728.0 797276.0 344270.0 969567.0 536521.0 897593.0 847194.0 974096.0 712363.0 717733.0 786369.0 686613.0 1152630.0 946144.0 239732.0 918833.0 380291.0 612418.0 602880.0 634786.0 695595.0 550256.0 602192.0 795023.0 731496.0 1120920.0 512178.0 555790.0 663147.0 500824.0 297017.0 735454.0 631914.0 667356.0 378814.0 797916.0 843802.0 506760.0 629936.0 600410.0 597657.0 192.0669062_MZ Methylhippuric acid Un 1.0 None None None None Methylhippuric acid is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction:. acyl-CoA + glycine < -- > CoA + N-acylglycine. Methylhippuric acid is a metabolite of xylene which is an aromatic hydrocarbon widely used as a solvant. It'e level can be measured in urine of workers exposed to xylene (PMID 8689499). C10H11NO3, Phenylacetylglycine, 2-Methylhippuric acid, m-Methylhippuric acid, p-Methylhippuric acid None None None 10273.7 12756.5 11457.3 9249.43 11387.3 13067.4 11367.0 22732.8 14114.6 10667.9 12677.1 16908.1 10491.8 11379.9 14789.7 16613.0 22885.5 9542.34 8681.94 10254.7 14795.6 17691.1 13546.2 14773.2 9151.89 13693.6 14091.9 14156.4 18117.3 15827.5 18951.8 13446.3 9491.99 11297.2 15166.8 14171.9 11391.9 11570.8 8870.0 12188.5 10364.8 12711.6 193.0353390_MZ D-Glucuronic acid Un 1.0 None None None None Glucuronic acid is a carboxylic acid that has the structure of a glucose molecule that has had its sixth carbon atom (of six total) oxidized. The salts of glucuronic acid are known as glucuronates. Glucuronic acid is highly soluble in water. In humans, glucuronic acid is often linked to toxic or poisonous substances to allow for subsequent elimination, and to hormones to allow for easier transport. These linkages involve O-glycosidic bonds. The process is known as glucuronidation, and the resulting substances are known as glucuronides (or glucuronosides). Glucuronidation uses UDP-glucuronic acid (glucuronic acid linked via a glycosidic bond to uridine diphosphate) as an intermediate. UDP-glucuronic acid is formed in the liver of all animals. C6H10O7, Galacturonic acid, Iduronic acid, Pectic acid, Pectin, 3-Dehydro-L-gulonate, 5-Keto-D-gluconate, 2-Keto-L-gluconate None None None 134198.0 123890.0 140062.0 105157.0 83004.4 115633.0 144604.0 111095.0 102812.0 99988.3 117571.0 117048.0 79975.2 104855.0 96122.5 65412.0 78927.7 42552.5 51514.5 91799.2 96583.8 107935.0 79258.7 103129.0 103386.0 145598.0 93414.3 71207.2 81385.9 94508.0 99215.8 60017.1 88836.5 91558.3 126304.0 82098.9 97300.6 103391.0 62620.9 93375.3 77842.2 87790.4 193.0713540_MZ Caffeine Un 1.0 None None None None Caffeine is the most widely consumed psychostimulant drug in the world that mostly is consumed in the form of coffee. Whether caffeine and/or coffee consumption contribute to the development of cardiovascular disease (CVD), the single leading cause of death in the US, is unclear. The literature indicates a strong relationship between boiled, unfiltered coffee consumption and elevated cholesterol levels; however, there is a critical gap in the literature regarding the effects of coffee or caffeine consumption on fibrinogen or CRP, which is an independent predictor of CVD risk. Available studies are limited by small samples sizes, inclusion of only men (or few women) and unrepresented age or ethnic groups. There is a critical need for controlled laboratory and epidemiological studies that include fibrinogen and CRP markers of CVD risk before conclusions can be drawn regarding the health effects of caffeine and/or coffee in a normal, healthy population of men and women. (PMID: 16856769 ). The relationship between caffeine consumption and various illnesses such as cardiovascular disease and cancer remains equivocal. Prudence might dictate that pregnant women and chronically ill individuals exercise restraint in their use of caffeine, although research suggests relatively low or nonexistent levels of risk associated with moderate caffeine consumption. (PMID: 7844249). There is extensive evidence that caffeine at dietary doses increases blood pressure (BP). However, concern that the drug may contribute to cardiovascular disease appears to have been dampened by (1) the belief that habitual use leads to the development of tolerance, and (2) confusion regarding relevant epidemiologic findings. When considered comprehensively, findings from experimental and epidemiologic studies converge to show that BP remains reactive to the pressor effects of caffeine in the diet. Overall, the impact of dietary caffeine on population BP levels is likely to be modest, probably in the region of 4/2 mm Hg. At these levels, however, population studies of BP indicate that caffeine use could account for premature deaths in the region of 14% for coronary heart disease and 20% for stroke. (PMID: 14747639). Caffeine is a purine alkaloid that occurs naturally in coffee beans. At intake levels associated with coffee consumption, caffeine appears to exert most of its biological effects through the antagonism of the A1 and A2A subtypes of the adenosine receptor. Adenosine is an endogenous neuromodulator with mostly inhibitory effects, and adenosine antagonism by caffeine results in effects that are generally stimulatory. Some physiological effects associated with caffeine administration include central nervous system stimulation, acute elevation of blood pressure, increased metabolic rate, and diuresis. Caffeine is rapidly and almost completely absorbed in the stomach and small intestine and distributed to all tissues, including the brain. Caffeine metabolism occurs primarily in the liver, where the activity of the cytochrome P450 isoform CYP1A2 accounts for almost 95% of the primary metabolism of caffeine. CYP1A2-catalyzed 3-demethylation of caffeine results in the formation of 1,7-dimethylxanthine (paraxanthine). Paraxanthine may be demethylated by CYP1A2 to form 1-methylxanthine, which may be oxidized to 1-methyluric acid by xanthine oxidase. Paraxanthine may also be hydroxylated by CYP2A6 to form 1,7-dimethyluric acid, or acetylated by N-acetyltransferase 2 (NAT2) to form 5-acetylamino-6-formylamino-3-methyluracil, an unstable compound that may be deformylated nonenzymatically to form 5-acetylamino-6-amino-3-methyluracil. Caffeine concentrations in coffee beverages can be quite variable. A standard cup of coffee is often assumed to provide 100 mg of caffeine, but a recent analysis of 14 different specialty coffees purchased at coffee shops in the US found that the amount of caffeine in 8 oz (=240 ml) of brewed coffee ranged from 72 to 130 mg.Caffeine in espresso coffees ranged from 58 to 76 mg in a single shot. (PMID 16507475). Caffeine is a member of the methylxanthine family of drugs, and is the most widely consumed behaviourally active substance in the western world. A number of in vitro and in vivo studies have demonstrated that caffeine modulates both innate and adaptive immune responses. For instance studies indicate that caffeine and its major metabolite paraxanthine suppress neutrophil and monocyte chemotaxis, and also suppress production of the pro-inflammatory cytokine tumor necrosis factor (TNF) alpha from human blood. Caffeine has also been reported to suppress human lymphocyte function as indicated by reduced T-cell proliferation and impaired production of Th1 (interleukin [IL]-2 and interferon [IFN]-gamma), Th2 (IL-4, IL-5) and Th3 (IL-10) cytokines. Studies also indicate that caffeine suppresses antibody production. The evidence suggests that at least some of the immunomodulatory actions of caffeine are mediated via inhibition of cyclic adenosine monophosphate (cAMP)-phosphodiesterase (PDE), and consequential increase in intracellular cAMP concentrations. Overall, these studies indicate that caffeine, like other members of the methylxanthine family, is largely anti-inflammatory in nature, and based on the pharmacokinetics of caffeine, many of its immunomodulatory effects occur at concentrations that are relevant to normal human consumption. (PMID 16540173). C8H10N4O2 None None None 20252.0 19676.9 22420.7 18822.3 16865.0 18071.0 39157.5 34576.1 10640.4 15961.5 14464.4 6695.95 25841.8 17154.6 21645.4 16518.0 47263.5 28351.5 19086.4 30168.1 18286.0 7275.5 14289.9 22017.4 15783.6 6927.3 20206.7 19755.4 6502.99 20262.5 26743.4 14517.5 5508.35 22644.6 6972.94 19834.7 11328.6 5493.49 12136.5 20698.4 34350.3 20344.9 193.1345051_MZ Ne,Ne dimethyllysine Un 1.0 None None None None Ne,Ne dimethyllysine is an intermediate in lysine degradation. Ne,Ne dimethyllysine a methylated form of lysine found in histones that contributes to gene regulation. C8H18N2O2 None None None 2295.51 3845.09 4071.4 4039.91 6095.72 4708.51 3504.15 3299.85 4053.31 4154.77 6220.81 4954.9 1682.54 4813.08 5050.74 3337.62 2835.75 1408.97 2739.79 2643.41 3152.23 3943.51 4185.8 2643.8 3598.25 3936.55 4491.88 3482.14 3723.31 4226.89 2522.98 2801.91 5122.02 2732.03 3791.49 2692.87 3115.56 5074.25 2103.9 4154.14 1835.09 2311.88 195.0511479_MZ Galactonic acid Un 1.0 None None None None Galactonate is increased in red blood cells of galactosemic patients, due to a galactose-1-phosphate uridyltransferase (GALT) deficiency ((PMID 14680973, OMMBID: The Metabolic and Molecular Bases of Inherited Disease, Ch.72). C6H12O7, Gluconic acid, Gulonic acid None None None 5390180.0 5896680.0 6511970.0 6764130.0 5555500.0 6261890.0 5578290.0 5084020.0 6468210.0 4873700.0 4430570.0 6932900.0 2833610.0 4907500.0 5949620.0 4096810.0 3093480.0 5337150.0 4657710.0 4695170.0 4246340.0 5234330.0 3923950.0 5093320.0 4900760.0 4830300.0 4734610.0 4545810.0 5828240.0 4183740.0 4245400.0 3483690.0 4012260.0 5403820.0 5628360.0 4976550.0 4632130.0 4501420.0 3268280.0 4806820.0 3950810.0 4148110.0 195.9897093_MZ Selenomethionine Un 1.0 None None None None Selenomethionine is an amino acid containing selenium that cannot be synthesized by higher animals, but can be obtained from plant material. Selenomethionine is the major seleno-compound in cereal grains (wheat grain, maize and rice), soybeans and enriched yeast. Seleno-compounds present in plants may have a profound effect upon the health of animals and human subjects. It is now known that the total Se content cannot be used as an indication of its efficacy, but knowledge of individual selenocompounds is necessary to fully assess the significance. Thus, speciation of the seleno-compounds has moved to the forefront. Since animals and man are dependent upon plants for their nutritional requirements, this makes the types of seleno-compounds in plants even more critical. Se enters the food chain through incorporation into plant proteins, mostly as selenocysteine and selenomethionine at normal Se levels. There are two possible pathways for the catabolism of selenomethionine. One is the transsulfuration pathway via selenocystathionine to produce selenocysteine, which in turn is degraded to H2Se by the enzyme b-lyase. The other pathway is the transamination-decarboxylation pathway. It was estimated that 90% of methionine is metabolized through this pathway and thus could be also the major route for selenomethionine catabolism. (PMID: 14748935, Br J Nutr. 2004 Jan;91(1):11-28.). C5H11NO2Se None None None 9134.66 10140.4 9052.49 14694.1 8240.85 8029.26 7982.65 9010.31 11250.8 8696.49 9955.52 10027.4 6273.26 11372.3 7687.99 8501.77 8949.75 6382.18 7496.39 8058.91 8217.95 10466.8 8800.65 9570.03 6745.93 8374.95 7229.38 8883.88 7640.12 10786.3 7800.15 8272.94 8715.11 9564.38 10733.4 8979.27 9809.79 11575.9 6958.51 9654.83 6143.36 8215.64 196.9846799_MZ Dihydroxyacetone Phosphate Acyl Ester Un 1.0 None None None None 1-acylglycerone 3-phosphate is found in the glycerophospholipid metabolism and ether lipid metabolism pathways. In the glycerophospholipid metabolism pathway, 1-acylglycerone 3-phosphate is created from glycerone phosphate, a reaction catalyzed by glyceronephosphate O-acyltransferase [EC:2.3.1.42]. 1-acylglycerone 3-phosphate is then converted to 1-acyl-sn-3-glycercol-phosphate or enters ether lipid metabolism. The conversion to 1-acyl-sn-3-glycercol-phosphate is catalyzed by 1-acylglycerone phosphate reductase [EC:1.1.1.101]. Within the ether lipid metabolism pathway, 1-acylglycerone 3-phosphate is converted to 1-alkyl-glycerone-3-phosphate through the action of alkyldihydroxyacetonephosphate synthase [EC:2.5.1.26]. C4H7O7P None None None 31806.3 27170.6 32437.3 21488.9 33425.8 24737.5 31882.7 42649.9 32229.2 28243.8 34494.9 34173.8 31227.1 28642.4 35198.2 29734.5 31768.7 25144.4 32503.1 31254.1 33015.7 37773.8 30909.4 34921.3 32506.9 31041.8 31284.4 32160.7 30765.8 27380.1 32011.1 34801.5 30453.5 29592.0 31552.4 27973.1 31654.7 38124.3 30351.8 35130.6 26561.5 30147.1 197.1545285_MZ trans-Dodec-2-enoic acid Un 1.0 None None None None Trans-Dodec-2-enoic acid is an intermediate in fatty acid biosynthesis. Specifically, trans-Dodec-2-enoic acid is converted from (R)-3-Hydroxydodecanoic acid via two enzymes; fatty-acid Synthase and 3-Hydroxypalmitoyl- [acyl-carrier-protein] dehydratase (EC: 2.3.1.85 and EC: 4.2.1.61). C12H22O2, 5-Dodecenoic acid None None None 27966.3 26821.5 19573.1 24915.8 21502.6 30599.5 28690.7 27978.9 18240.6 24582.6 21413.7 16092.1 19669.3 27968.7 21603.7 20285.0 35276.9 23493.7 21974.1 23918.7 25662.8 15898.1 26823.0 30703.8 17360.7 14965.6 19810.0 21054.9 15563.7 29718.8 19184.6 19030.7 14309.5 20701.4 19475.6 22593.7 16455.2 14522.3 18291.1 24059.6 17427.2 21421.1 198.0220038_MZ O-Phosphohomoserine Un 1.0 None None None None O-phosphohomoserine is a naturally occurring analogue of phosphonate amino acids. O-phosphohomoserine has been found in trace amounts in shotgun-metabolomics analysis in mouse tissue extracts, and is the substrate of a threonine analog enzyme in murine species. O-phosphohomoserine, an analogue of the excitatory amino acid antagonist 2-amino-phosphonovalerate is an N-methyl-D-aspartate (NMDA) antagonist. (PMID: 3528930, 17034760, 17665876). C4H10NO6P, O-Phosphothreonine None None None 10095.2 5514.24 6303.23 3877.67 6274.05 6109.47 5592.48 7160.38 5881.41 5084.16 5645.85 7810.72 4272.87 5480.47 5926.03 6431.82 4272.44 6126.3 4924.82 7531.37 4982.22 6710.91 5548.92 5821.22 5659.17 5074.8 5021.9 5782.29 6863.94 7352.65 6462.81 4318.01 5736.63 4953.74 6028.93 5576.65 4691.25 5770.73 4038.42 6524.3 4648.63 4700.69 198.0388248_MZ Isoxanthopterin Un 1.0 None None None None Isoxanthopterin is a pteridine normally present in plasma, urine, and other bodily fluids also vary from normal concentrations in some disease states and also have diagnostic value. Pteridines' urinary concentrations seem to vary independently from each other and from normal values to yield a pattern of excreted pteridines that is diagnostic for different species, tissues, and tumor types. Intravenous or intramuscular administration of isoxanthopterin inhibits the growth rates of animal tumor models. Pteridin derivatives are a family of organic compound with very similar chemical structures which play an important biochemistry role. Pteridines metabolism and its regulation in normal and pathological conditions have not been extensively investigated due to the difficulty of their quantification. A significant decrease of isoxanthopterin has been determined in cancer patients. (PMID 15837549, 9800651). Xanthine dehydrogenase (XDH) is the enzymes responsible for the conversion of xanthine to uric acid. It requires the presence of the molybdenum cofactor for its proper functioning. XDH is reported to have additional functions, i.e., the conversion of pterin to isoxanthopterin, one of the steps the degradation pathway of 5,6,7,8-tetrahydrobiopterin (BH4). Isoxanthopterin is very low in some cases of hereditary xanthinuria (OMIM 278300) and molybdenum cofactor deficiency (OMIM 252150). (PMID: 8812740). C6H5N5O2 None None None 5028.44 4340.96 4622.7 5004.25 4372.23 5259.04 4474.89 4674.23 4336.41 4781.89 4951.67 4645.89 3495.46 4807.73 4850.08 4728.21 3760.92 4025.99 4483.76 5406.8 4044.45 4012.5 4506.39 4968.21 4110.72 3496.84 4304.86 4172.97 4241.27 5025.4 5215.49 4620.75 3587.24 4147.89 4072.97 4917.32 3661.3 4576.63 2910.74 4921.08 4115.32 4027.38 198.1133260_MZ Ecgonine methyl ester Un 1.0 None None None None Ecgonine methyl ester is a major metabolite of cocaine. It is generally not measured by HPLC because it is poorly detectable by UV, and its water solubility makes recovery from urine difficult. Using modified solid-phase extraction procedures, recoveries of 85% for ecgonine methyl ester could be obtained from urine. (PMID:1298401). C10H17NO3 None None None 7255.11 7976.33 6985.85 10336.3 6359.78 7692.33 7651.39 9525.2 6779.47 6842.22 9492.69 9645.25 6493.95 8082.79 6229.71 8340.3 8618.77 7928.36 6274.63 6062.63 8821.8 7469.83 8038.38 8346.32 8286.61 5997.58 6978.11 7762.43 7513.04 9455.29 7505.39 7222.0 5656.83 7507.75 7228.39 9288.67 6551.56 8028.68 4586.16 7297.9 6101.48 6504.45 199.0019137_MZ D-Erythrose 4-phosphate Un 1.0 None None None None D-Erythrose 4-phosphate is a phosphorylated derivative of erythrose that serves as an important intermediate in the pentose phosphate pathway. It is also used in phenylalanine, tyrosine and tryptophan biosynthesis, and it plays a role in vitamin B6 metabolism (KEGG). C4H9O7P None None None 36155.4 33314.3 39701.2 29668.9 34802.4 37400.1 37900.7 36623.7 43736.9 36528.7 37170.1 38925.2 38631.7 36254.7 40016.4 28637.5 36093.2 43072.6 38348.8 35051.7 37563.8 44454.7 35951.0 39922.3 36073.0 37968.9 35725.0 38013.9 36764.0 41940.8 28043.2 29696.8 43447.7 35400.9 40973.3 41773.3 39271.2 40223.0 37423.6 38720.6 34396.7 36071.3 199.0877249_MZ 5-Hydroxykynurenamine Un 1.0 None None None None 5-Hydroxykynurenamine is an intermediate in the tryptophan metabolic pathway [Kegg: C05638]. It is generated from 5-hydroxykynurenine via the enzyme DOPA decarboxylase. C9H12N2O2, Tyrosinamide None None None 4085.81 4029.2 3979.01 3046.68 3694.37 4520.81 4465.69 4964.98 3159.73 3493.47 3681.69 3172.48 4355.42 3411.39 3770.0 5398.78 5178.74 4056.37 3394.96 4515.81 3774.42 2861.76 3845.84 3682.33 3569.61 3347.9 3963.67 3661.5 3163.31 4315.72 3975.29 3898.97 2833.46 3154.79 3191.66 3419.77 2859.99 3069.97 2650.67 3647.02 3314.43 3513.94 199.0974615_MZ cis-4-Decenedioic acid Un 1.0 None None None None cis-4-Decenedioic acid is an unsaturated dicarboxylic acid. Its level increases in patients with medium chain acyl-CoA dehydrogenase deficiency, which is a disorder of fatty acid oxidation. C10H16O4, cis-4-Decenedioic acid, cis-5-Decenedioic acid None None None 23878.1 22686.3 31409.8 23677.4 28773.9 27462.5 28376.1 40203.4 18571.5 22209.8 25901.2 20535.6 16708.4 26780.3 32991.1 25447.2 54562.5 14566.1 17673.1 24222.3 20363.3 17024.1 22039.9 21405.6 21637.2 16961.7 28121.3 20372.5 15625.2 29019.5 19309.6 18034.7 18330.6 17553.6 17814.3 19049.3 16502.4 18779.1 16491.4 24020.5 13669.2 17961.0 199.1703053_MZ Dodecanoic acid Un 1.0 None None None None Lauric acid, or dodecanoic acid is the main fatty acid in coconut oil and in palm kernel oil, and is believed to have antimicrobial properties. It is a white, powdery solid with a faint odor of bay oil. Lauric acid, although slightly irritating to mucous membranes, has a very low toxicity and so is used in many soaps and shampoos. C12H24O2 None None None 227955.0 197012.0 223850.0 175977.0 170984.0 214356.0 408793.0 372896.0 120007.0 189141.0 147567.0 81061.3 253816.0 199194.0 204156.0 139416.0 514935.0 372662.0 199896.0 350290.0 181211.0 82950.8 168592.0 236727.0 151987.0 73730.2 168045.0 283755.0 71939.9 225575.0 255463.0 134780.0 73252.9 262172.0 85856.9 206396.0 116186.0 77785.6 142872.0 200692.0 309537.0 199092.0 199.9691094_MZ Cysteine-S-sulfate Un 1.0 None None None None Cysteine-S-sulfate (SSC) is produced by reaction of inorganic sulfite and cystine by a yet unknown pathway and is a very potent NMDA-receptor agonist. Electrophysiological studies have shown that SSC displays depolarizing properties similar to glutamate. Patients affected with either Molybdenum cofactor deficiency (MOCOD, an autosomal recessive disease that leads to a combined deficiency of the enzymes sulphite oxidase, an enzyme that catalyzes the conversion of sulfite to inorganic sulfate, xanthine dehydrogenase and aldehyde oxidase) or isolated sulphite oxidase deficiency (ISOD, an extremely rare autosomal recessive disorder with identical clinical manifestations to MOCOD) excrete elevated levels of SSC. This rare disorder is associated with brain damage (seizures, spastic quadriplegia, and cerebral atrophy), mental retardation, dislocated ocular lenses, blindness, and excretion in the urine of abnormally large amounts of SSC, sulfite, and thiosulfate but no inorganic sulfate. (PMID: 17764028, 15558695). C3H7NO5S2 None None None 1183.78 1358.53 1243.38 2313.4 1699.48 1569.95 1621.1 1409.85 1526.12 1880.91 1390.91 1293.78 1511.11 1782.21 2495.65 2177.7 1368.39 1180.04 1419.98 1224.35 1400.93 1352.86 1526.19 1261.88 1346.22 1196.12 1588.07 1314.9 1220.49 1480.39 1683.58 2202.46 1334.21 1412.93 1780.0 1172.72 1352.78 1530.88 1274.22 1573.55 1405.02 1296.37 200.1291653_MZ Capryloylglycine Un 1.0 None None None None Capryloylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction:. acyl-CoA + glycine < -- > CoA + N-acylglycine. A complex of amino acid protein that helps kill microbes, and protects skin from water loss. C10H19NO3, Valproylglycine None None None 12591.8 8458.07 14203.8 24780.7 7010.42 12861.0 16683.9 14360.0 7672.08 14131.9 10896.3 9463.12 9838.19 13008.9 7631.39 8977.26 17194.3 9732.07 7550.75 13865.0 14215.9 8110.25 13093.2 12605.0 10639.0 10103.5 6132.34 13220.3 8519.34 14705.6 12557.4 9818.58 8983.26 10413.6 11101.2 14050.8 8927.54 7935.65 4724.04 10589.4 9775.36 10787.5 201.1130602_MZ Sebacic acid Un 1.0 None None None None Sebacic acid is a saturated, straight-chain naturally occurring dicarboxylic acid with 10 carbon atoms. Sebacic acid is a normal urinary acid. In patients with multiple acyl-CoA-dehydrogenase deficiency (MADD) or glutaric aciduria type II (GAII) are a group of metabolic disorders due to deficiency of either electron transfer flavoprotein or electron transfer flavoprotein ubiquinone oxidoreductase, biochemical data shows an increase in urine sebacic acid excretion. Sebacic acid is a white flake or powdered crystal slightly soluble in water that has been proposed as an alternative energy substrate in total parenteral nutrition. Sebacic Acid was named from the Latin sebaceus (tallow candle) or sebum (tallow) in reference to its use in the manufacture of candles. Sebacic Acid and its derivatives such as azelaic acid have a variety of industrial uses as plasticizers, lubricants, hydraulic fluids, cosmetics, candles, etc. It is used in the synthesis of polyamide and alkyd resins. It is also used as an intermediate for aromatics, antiseptics and painting materials. (PMID: 10556649, 1738216, 8442769, 12706375). C10H18O4 None None None 41461.1 38736.8 30374.3 58900.9 34432.3 40904.7 33029.0 49963.7 24763.3 37322.7 35966.2 16879.5 18126.2 38558.7 39355.2 32747.7 55290.2 15017.4 32811.1 28397.1 37782.7 14830.8 34968.5 44618.2 33622.7 18939.1 36581.0 22488.9 14668.6 44762.4 23878.9 27009.0 13028.5 27837.4 18655.5 38935.0 23271.1 13409.1 22672.1 36416.9 14809.0 36404.4 202.1083944_MZ L-Acetylcarnitine Un 1.0 None None None None L-Acetylcarnitine is an acetic acid ester of carnitine that facilitates movement of acetyl CoA into the matrices of mammalian mitochondria during the oxidation of fatty acids. In addition to his metabolic role, acetyl-L-carnitine (ALC) posses unique neuroprotective, neuromodulatory, and neurotrophic properties this may play an important role in counteracting various disease processes. (PubMed ID 15363640). C9H17NO4 None None None 13487.3 11084.6 11264.9 8950.37 12478.9 22531.8 12352.7 10979.2 12257.9 10945.0 10387.6 15575.2 11634.2 11148.5 9978.97 31759.9 8724.48 21077.6 12931.0 16336.0 10431.5 11677.1 15088.3 12649.1 11067.4 13785.2 9399.64 14852.8 12405.7 16021.9 12775.5 19002.8 12863.4 10054.9 9751.5 13549.2 10359.7 9587.21 5744.84 11731.6 14109.7 10404.9 203.0673519_MZ 5-L-Glutamylglycine Un 1.0 None None None None 5-L-glutamylglycine is one of the dipeptides that is commonly produced from polypeptides by the action of the enzyme dipeptidyl peptidase. Dietary proteins are digested to dipeptides and amino acids, and the dipeptides are absorbed more rapidly than the amino acids, because their uptake involves a separate mechanism. Dipeptides activate G-cells found in the stomach to secrete gastrin. 5-L-glutamylglycine is an excitatory amino acid receptor antagonist with a structure similar to gamma-aminobutyric acid (GABA). (PMID: 6146532). C7H12N2O5, L-beta-aspartyl-L-alanine None None None 25951.6 24980.4 24771.0 24683.4 21052.8 26163.3 22485.6 35790.8 21162.8 20882.8 21582.1 23403.2 17351.1 23230.1 19107.1 23738.9 20754.7 15828.0 18598.7 20070.2 21455.8 22151.5 19584.5 24020.3 21253.1 29841.0 22929.0 21968.3 26950.6 22852.3 22014.1 22293.9 19211.9 20836.2 23919.5 22979.1 21514.5 20801.2 13863.7 22695.7 16689.7 19580.8 203.0824159_MZ Tryptophan Un 1.0 None None None None Tryptophan is an essential amino acid which is the precursor of serotonin. Serotonin is a brain neurotransmitter, platelet clotting factor and neurohormone found in organs throughout the body. Metabolism of tryptophan to serotonin requires nutrients such as vitamin B6, niacin and glutathione. Niacin is an important metabolite of tryptophan. High corn or other tryptophan-deficient diets can cause pellagra, which is a niacin-tryptophan deficiency disease with symptoms of dermatitis, diarrhea and dementia. Inborn errors of tryptophan metabolism exist where a tumor (carcinoid) makes excess serotonin. Hartnup's disease is a disease where tryptophan and other amino acids are not absorbed properly. Tryptophan supplements may be useful in each condition, in carcinoid replacing the over-metabolized nutrient and in Hartnup's supplementing a malabsorbed nutrient. Some disorders of excess tryptophan in the blood may contribute to mental retardation. Assessment of tryptophan deficiency is done through studying excretion of tryptophan metabolites in the urine or blood. Blood may be the most sensitive test because the amino acid tryptophan is transported in a unique way. Increased urination of tryptophan fragments correlates with increased tryptophan degradation, which occurs with oral contraception, depression, mental retardation, hypertension and anxiety states. The requirement for tryptophan and protein decreases with age. Adults' minimum daily requirement is 3 mg/kg/day or about 200 mg a day. This may be an underestimation, for there are 400 mg of tryptophan in just a cup of wheat germ. A cup of low fat cottage cheese contains 300 mg of tryptophan and chicken and turkey contain up to 600 mg per pound. (http://www.dcnutrition.com). C11H12N2O2 None None None 92860.0 84804.1 91825.8 54861.6 79476.7 107966.0 73100.5 73057.1 91478.5 80481.5 72269.7 109229.0 95934.6 91965.1 87872.7 90114.3 66564.0 90266.3 87372.9 94036.7 92596.3 91348.7 75654.3 82323.4 71289.2 75815.9 93627.7 83253.5 92971.1 81074.2 63215.2 69439.0 96529.5 76204.9 113970.0 92431.5 78801.3 82571.9 57464.4 85178.2 70392.6 76035.1 204.0668516_MZ Indolelactic acid Un 1.0 None None None None Indolelactic acid is a tryptophan metabolite found in human plasma and serum and normal urine. Tryptophan is metabolized by two major pathways in humans, either through kynurenine or via a series of indoles, and some of its metabolites are known to be biologically active. Indolelactic acid is present in various amounts, significantly higher in umbilical foetal plasma than in maternal plasma in the protein-bound form. (PMID 2361979, 1400722, 3597614, 11060358, 1400722). C11H11NO3, 5-Methoxyindoleacetate, Cinnamoylglycine None None None 35916.9 16801.2 25749.6 11830.2 8216.52 8239.09 14462.3 16295.0 11190.4 6145.62 5885.35 18318.5 24539.1 7900.1 8015.93 12325.0 17440.1 29780.9 10761.3 21054.9 8864.95 14649.6 6201.54 11573.2 7922.91 11973.5 9903.58 20801.8 10697.0 10554.5 20977.7 7612.39 4681.08 16363.3 10739.3 10527.1 18816.7 5155.63 4839.15 13551.7 15497.1 7755.83 204.1242579_MZ Pantothenol Un 1.0 None None None None In cosmetics, panthenol is a humectant, emollient and moisturizer. It binds to hair follicles readily and is a frequent component of shampoos and hair conditioners (in concentrations of 0.1-1%). It coats the hair and seals its surface, lubricating follicles and making strands appear shiny. Panthenol is the alcohol analog of pantothenic acid (vitamin B5), and is thus the provitamin of B5. In organisms it is quickly oxidized to pantothenate. Panthenol is a viscous transparent liquid at room temperature, but salts of pantothenic acid (for example sodium pantothenate) are powders (typically white). It is well soluble in water, alcohol and propylene glycol, soluble in ether and chloroform, and slightly soluble in glycerin. C9H19NO4 None None None 2187.25 2241.66 2032.95 2375.88 2321.33 2124.57 2513.2 2569.99 2148.75 2263.18 2145.17 2873.2 1962.06 2510.25 2301.67 1521.21 2591.69 2272.72 2065.85 2222.38 2573.05 1861.95 2382.97 2445.27 2375.77 3124.27 1669.55 2650.56 1727.14 2498.25 1615.52 1483.41 2040.4 2691.39 1756.97 2108.37 1709.37 1834.94 1474.07 1848.64 2359.34 1779.47 204.9915304_MZ 2-Phosphoglyceric acid Un 1.0 None None None None 2-Phosphoglyceric acid (2PGA) is a glyceric acid which serves as the substrate in the ninth step of glycolysis. It is catalyzed by enolase into phosphoenolpyruvate (PEP), the penultimate step in the conversion of glucose to pyruvate. Enolase catalyzes the beta-elimination reaction in a stepwise manner wherein OH- is eliminated from C3 of a discrete carbanion (enolate) intermediate. This intermediate is created by removal of the proton from C2 of 2PGA by a base in the active site. (PMID: 8994873, Wikipedia). C3H7O7P, 2-Phospho-D-glyceric acid, 3-Phosphoglyceric acid None None None 5540.04 5309.51 5825.42 6084.71 5309.02 5866.75 5500.43 5222.58 6381.16 6592.52 5378.78 6916.24 4790.64 5462.05 5606.36 5942.96 5321.79 6152.32 5553.61 5383.74 5500.81 6595.49 5588.33 5433.14 5411.18 6385.6 4995.72 6247.01 6954.2 5799.35 5637.56 5841.3 6625.47 5475.85 7042.28 6092.7 6096.93 6501.72 5228.41 5743.22 5367.83 5419.95 205.0353814_MZ (R)-lipoic acid Un 1.0 None None None None Lipoic acid is a vitamin-like antioxidant that acts as a free-radical scavenger. Alpha-lipoic acid is also known as thioctic acid. It is a naturally occurring compound that is synthesized by both plants and animals. Lipoic acid contains two thiol groups which may be either oxidized or reduced. The reduced form is known as dihydrolipoic acid (DHLA). Lipoic acid (Delta E= -0.288) is therefore capable of thiol-disulfide exchange, giving it antioxidant activity. Lipoate is a critical cofactor for aerobic metabolism, participating in the transfer of acyl or methylamine groups via the 2-Oxoacid dehydrogenase (2-OADH) or alpha-ketoglutarate dehydrogenase complex. This enzyme catalyzes the conversion of alpha-ketoglutarate to succinyl CoA. This activity results in the catabolism of the branched chain amino acids (leucine, isoleucine and valine). Lipoic acid also participates in the glycine cleavage system(GCV). The glycine cleavage system is a multi-enzyme complex that catalyzes the oxidation of glycine to form 5,10 methylene tetrahydrofolate, an important cofactor in nucleic acid synthesis. Since Lipoic acid is an essential cofactor for many enzyme complexes, it is essential for aerobic life as we know it. This system is used by many organisms and plays a crucial role in the photosynthetic carbon cycle. Lipoic acid was first postulated to be an effective antioxidant when it was found it prevented vitamin C and vitamin E deficiency. It is able to scavenge reactive oxygen species and reduce other metabolites, such as glutathione or vitamins, maintaining a healthy cellular redox state. Lipoic acid has been shown in cell culture experiments to increase cellular uptake of glucose by recruiting the glucose transporter GLUT4 to the cell membrane, suggesting its use in diabetes. Studies of rat aging have suggested that the use of L-carnitine and lipoic acid results in improved memory performance and delayed structural mitochondrial decay. As a result, it may be helpful for people with Alzheimer's disease or Parkinson's disease. -- Wikipedia. C8H14O2S2, 2-Methylcitric acid, Homocitric acid, Methylisocitric acid None None None 23826.2 35182.5 40407.8 51675.3 34294.6 31001.1 44246.9 37685.1 34868.8 27436.4 38374.0 51955.5 37678.4 35901.8 31469.4 13441.4 26638.9 20325.7 39449.8 29153.2 26845.6 27855.8 33895.6 27900.9 30252.3 27772.8 32077.0 32165.6 23255.5 24950.8 14770.1 18811.2 31314.9 19746.1 20877.9 37256.1 38114.1 40053.0 15272.7 33242.3 21742.7 33503.7 205.1232469_MZ Ibuprofen Un 1.0 None None None None Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID) widely marketed under various trademarks including Act-3, Advil, Brufen, Motrin, Nuprin, and Nurofen. It is used for relief of symptoms of arthritis, primary dysmenorrhoea, and fever; Ibuprofen is an NSAID which is believed to work through inhibition of cyclooxygenase (COX), thus inhibiting prostaglandin synthesis. There are at least 2 variations of cyclooxygenase (COX-1 and COX-2), ibuprofen inhibits both COX-1 and COX-2. It appears that its analgesic, antipyretic, and anti-inflammatory activity are achieved principally through COX-2 inhibition; whereas COX-1 inhibition is responsible for its unwanted effects on platelet aggregation and the GI mucosa. As with other NSAIDs, ibuprofen inhibits platelet aggregation, but is not used therapeutically for this action since it is a minor and reversible effect. -- Wikipedia. C13H18O2 None None None 15988.5 32790.2 44658.3 36886.4 72244.6 53435.0 30595.0 21667.1 45347.1 43325.3 68284.5 53960.5 6954.1 45615.1 50275.0 28744.8 15840.9 4700.57 29006.9 15723.1 25163.5 44749.8 45690.2 27277.1 34178.4 50034.7 47639.7 30944.8 43092.8 38798.7 20968.3 21154.0 63961.1 22515.4 42386.0 22452.7 36092.1 56668.9 18529.6 41833.1 8888.38 18085.3 206.0593336_MZ Indoleacrylic acid Un 1.0 None None None None Indoleacrylic acid is a natural auxin from lentil roots. Inhibits the growth of mycelia of Neurospora crassa and causes the cells to accumulate indoleglycerol phosphate. C11H9NO2 None None None 13425.5 12235.5 14083.8 13648.0 12644.0 16086.1 12098.3 10747.4 12832.7 13551.5 12225.8 14292.8 14556.2 14551.8 12731.0 16418.4 12109.6 12417.9 13091.7 12495.2 13142.0 13663.8 13294.3 12639.7 11587.2 12509.1 14088.7 13449.6 15045.3 13899.6 10534.7 12851.3 13004.1 11219.8 15729.9 14942.1 11900.4 12127.2 9465.11 13296.2 12352.2 12342.3 206.0821217_MZ Phenylpropionylglycine Un 1.0 None None None None Phenylpropionylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction:acyl-CoA + glycine < -- > CoA + N-acylglycineThe detection of phenylpropionylglycine in urine after an oral load of phenylpropionic acid can be used to diagnose deficiency of medium-chain acyl-CoA dehydrogenase, a frequent and treatable metabolic defect. (PMID 9234867). C11H13NO3, N-Acetyl-L-phenylalanine, 3-Phenylpropionylglycine None None None 25076.2 21795.7 23598.8 20779.8 29578.0 22779.6 17875.6 16273.4 35794.8 19126.9 28327.5 30049.4 14839.4 13259.7 26650.7 35775.0 20304.0 24873.1 18761.9 25029.2 21976.8 17906.7 22585.9 18564.1 16077.7 17298.2 26623.6 20440.1 21564.0 21922.5 22102.8 15362.8 20363.0 17735.0 23805.2 21456.2 16285.3 17726.4 11395.9 24552.3 20870.4 17868.4 207.1391422_MZ 3-Hydroxycapric acid Un 1.0 None None None None 3-hydroxycapric acid is a normally occurring carboxylic acid in human blood plasma. Medium- and long-chain 3-hydroxymonocarboxylic acids represent intermediates in the beta-oxidation of fatty acids. They accumulate in the plasma of patients with an inherited deficiency of long-chain 3-hydroxyacylCoA dehydrogenase [EC 1.1.1.35]. (PMID: 1912723). 3-hydroxyacyl-CoA dehydrogenase deficiency (HADH) has been described in diverse clinical cases: in cases of juvenile-onset recurrent myoglobinuria, hypoketotic hypoglycemic encephalopathy, in hypertrophic/dilatative cardiomyopathy, in sudden infant death, and in fulminant hepatic failure. (OMIM 231530). 3-hydroxycapric acid has some shape-transforming action on the membrane of intact human erythrocytes. (PMID: 7318031). C10H20O3, (R)-3-Hydroxydecanoic acid None None None 22443.2 24728.5 28561.9 21675.5 25408.3 28313.8 22743.9 21200.2 24511.0 22698.2 26916.2 23190.6 11463.3 26484.3 24090.9 16425.5 26851.8 13887.4 15396.7 16070.6 21099.3 25246.3 21998.2 22528.5 18369.8 24944.7 22294.3 25210.7 26217.0 26067.9 15735.7 14619.2 24090.7 22488.4 29355.9 17498.1 20774.4 21971.9 14641.6 21937.9 12207.4 15982.4 207.1492077_MZ N6_N6_N6-Trimethyl-L-lysine Un 1.0 None None None None N6,N6,N6-Trimethyl-L-lysine is a methylated derivative of the amino acid lysine. It is a component of histone proteins, a precursor of carnitine and a coenzyme of fatty acid oxidation. N6,N6,N6-Trimethyl-L-lysine residues are found in a number of proteins and are generated by the action of S-adenosyl-L-methionine on exposed lysine residues. When trimethyllysine is released from cognate proteins via proteolysis, it serves as a precursor for carnitine biosynthesis. Mitochondrial 6-N-trimethyllysine dioxygenase converts 6-N-trimethyllysine to 3-hydroxy-6-N-trimethyllysine as the first step for carnitine biosynthesis. Because the subsequent carnitine biosynthesis enzymes are cytosolic, 3-hydroxy-6-N-trimethyllysine must be transported out of the mitochondria by a putative mitochondrial 6-N-trimethyllysine/3-hydroxy-6-N-trimethyllysine transporter system. Plasma -N-trimethyllysine concentrations are significantly lower in systemic carnitine deficiency patients compared to normal individuals, but no significant difference in urinary -N-trimethyllysine excretion is seen between the two groups. C9H20N2O2 None None None 3647.51 3852.86 4523.37 3467.4 3950.78 4292.48 3637.01 3438.59 3980.54 3576.2 4155.92 3746.39 1996.19 4166.98 4095.74 2583.74 4444.25 2451.99 2706.08 2700.33 3524.42 4106.18 3652.57 3676.7 3165.04 3942.65 3537.88 4026.64 4073.0 4239.43 2637.97 2383.89 3826.3 3581.42 4563.14 2992.14 3374.44 3580.65 2602.08 3690.22 2225.61 2765.99 208.0526838_MZ Hydroxyphenylacetylglycine Un 1.0 None None None None Hydroxyphenylacetylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction:. acyl-CoA + glycine < -- > CoA + N-acylglycine. Hydroxyphenylacetylglycine is an endogenous human metabolite. It can be originated from the metabolism of tyramine, itself is a monoamine compound derived from the amino acid tyrosine. Hydroxyphenylacetylglycine can also be derived from the metabolism of 3,4-dihydroxyphenylalanine (L-DOPA). In the metabolism of tyrosine, this compound is involved in the reaction Hydroxyphenylacetyl-CoA + Glycine <=> Hydroxyphenylacetylglycine + CoA, catalyzed by acyltransferase enzymes (EC 2.3.1.-). Hydroxyphenylacetylglycine has been identified in human biofluids. (PMID: 14201174, 912020, 716472, 7096501, 7438429, 7438430). C10H11NO4 None None None 5876.41 4830.28 5060.08 4156.67 4429.94 5380.51 4724.64 4362.34 4159.39 4854.46 4359.27 4390.09 4777.35 4836.8 4698.23 4434.65 4535.9 5083.01 4455.01 5217.49 4819.54 4518.76 4772.54 4698.45 4039.67 3748.92 4693.09 4320.17 4653.3 5896.97 4490.83 3893.8 4169.36 4017.23 4161.83 4827.08 3920.23 3966.09 3247.2 5197.86 4532.59 4601.08 209.0461009_MZ Vanilpyruvic acid Un 1.0 None None None None Vanilpyruvic acid is a catecholamine metabolite and precursor to vanilactic acid. Accumulation in urine is indicative of Aromatic L-aminoacid decarboxylase deficiency (PMID 16288991). C10H10O5 None None None 22368.4 19317.9 19610.6 22140.8 20649.2 21862.3 23072.3 25471.0 14774.2 25992.0 23198.2 14879.0 19176.1 20552.5 21529.0 22336.2 29799.0 26089.2 21769.5 19999.4 19533.4 13363.1 21512.5 21211.5 17585.1 15565.1 21770.1 19757.6 13146.5 22316.4 18708.2 21137.1 12590.1 15899.0 15181.8 25105.0 14229.7 12482.0 15018.1 18782.0 24843.8 22789.6 210.0283355_MZ Phosphocreatine Un 1.0 None None None None Phosphocreatine undergoes irreversible cyclization and dehydration to form creatinine at a fractional rate of 0.026 per day, thus forming approximately 2 g creatinine/day in an adult male. This is the amount of creatine that must be provided either from dietary sources or by endogenous synthesis to maintain the body pool of (creatine and) phosphocreatine. Creatine is an amino acid that plays a vital role as phosphocreatine in regenerating adenosine triphosphate in skeletal muscle to energize muscle contraction. Creatine is phosphorylated to phosphocreatine in muscle in a reaction that is catalyzed by the enzyme creatine kinase. This enzyme is in highest concentration in muscle and nerve. Oral administration increases muscle stores. During the past decade, creatine has assumed prominence as an ergogenic (and legal) aid for professional and elite athletes. Most (~ 95%) of the total body creatine-phosphocreatine pool is in muscle (more in skeletal muscle than in smooth muscle) and amounts to 120 g (or 925 mmol) in a 70 kg adult male. Approximately 60-67% of the content in resting muscle is in the phosphorylated form. This generates enough ATP at the myofibrillar apparatus to power about 4 seconds of muscle contraction in exercise. Phosphocreatine reacts with ADP to yield ATP and creatine; the reversible reaction is catalyzed by creatine kinase. phosphocreatine is the chief store of high-energy phosphates in muscle. Thus, this reaction, which permits the rephosphorylation of ADP to ATP, is the immediate source of energy in muscle contraction. During rest, metabolic processes regenerate phosphocreatine stores. In normal muscle, ATP that is broken down to ADP is immediately rephosphorylated to ATP. Thus, phosphocreatine serves as a reservoir of ATP-synthesizing potential. phosphocreatine is the only fuel available to precipitously regenerate ATP during episodes of rapid fluctuations in demand. The availability of phosphocreatine likely limits muscle performance during brief, high-power exercise, i.e., maximal exercise of short duration. With near maximal isometric contraction, the rate of utilization of phosphocreatine declines after 1-2 seconds of contraction, prior to the glycolysis peak at approximately 3 seconds. (PMID: 10079702, Nutr Rev. 1999 Feb;57(2):45-50.). C4H10N3O5P None None None 9237.13 8828.26 9454.21 10239.3 7863.31 9744.2 8229.38 10785.3 7124.39 8601.79 9258.9 6381.23 9907.85 11671.6 10724.6 11246.8 10119.0 8797.51 8540.21 9688.93 9656.05 7612.85 7833.44 8542.81 9665.43 8983.58 7684.62 7956.81 9235.87 11080.1 8847.48 10306.9 7622.27 7294.32 9729.73 8273.89 8682.31 8613.06 8997.88 8843.74 11193.8 7783.16 211.0600907_MZ Vanillactic acid Un 1.0 None None None None Vanillactic acid is an acidic catecholamine metabolite present in normal human urine (PMID 7524950), in normal human CSF (PMID 7914240), and increased in the CSF of newborns with neonatal epileptic encephalopathy mimicking aromatic L-amino acid decarboxylase deficiency (PMID 12200739). C10H12O5 None None None 11372.2 11105.6 13088.9 13758.5 14073.0 14349.6 15960.4 18061.7 9488.21 12563.2 13431.8 8236.42 10110.4 13302.8 15697.7 12454.1 22965.2 9212.0 12476.8 12416.0 13596.6 7554.25 11962.9 13188.1 12441.3 7355.39 13644.0 9797.83 7113.81 13185.5 10354.2 11388.1 6507.35 8883.63 8396.37 12727.5 7840.42 7083.52 8366.38 11921.7 8672.52 11914.1 212.0021517_MZ Indoxyl sulfate Un 1.0 None None None None Indoxyl sulfate is a dietary protein metabolite, and also the metabolite of the common amino acid tryptophan. Indoxyl sulfate is a circulating uremic toxin stimulating glomerular sclerosis and interstitial fibrosis. Indoxyl sulfate is one of the well known substances of a group of protein-bound uremic retention solutes. Indoxyl sulfate increases the rate of progression of renal failure. In plasma, indoxyl sulfate is a protein-bound uremic solute that induces endothelial dysfunction by inhibiting endothelial proliferation and migration in vitro. Some studies suggest that indoxyl sulfate is also involved in oxidative stress. In hemodialyzed patients, serum levels of indoxyl sulfate are associated with levels of pentosidine, a marker of carbonyl and oxidative stress; in vitro, indoxyl sulfate increases reactive oxygen species (ROS) production in tubular cells, and increases NAD(P)H oxidase activity in endothelial cells. Indoxyl sulfate impairs osteoblst function and induces abnormalities of bone turnover. Indoxyl sulfate strongly decreases the levels of glutathione, one of the most active antioxidant systems of the cell. (PMID: 10681668, 14681860, 17471003, 17403109). C8H7NO4S None None None 19167.5 16731.0 20025.0 17930.2 21265.3 18339.0 15530.1 31667.3 16811.5 16402.3 16349.3 29957.4 19077.8 16407.4 27388.1 26529.1 26518.7 18064.6 13610.7 18087.8 19043.0 17666.1 20689.6 19908.8 16476.5 14409.9 16548.8 13733.9 21300.2 25783.0 23948.9 21948.0 12205.3 14885.3 18062.7 21412.5 14390.6 12687.6 11480.4 20173.9 13921.2 14971.9 213.1495889_MZ 3-Oxododecanoic acid Un 1.0 None None None None 3-Oxo-Dodecanoic acid is an intermediate in fatty acid biosynthesis. Specifically, 3-Oxo-Dodecanoic acid is converted form Malonic acid via three enzymes; 3-oxoacyl-[acyl-carrier-protein] synthase, fatty-acid Synthase and beta-ketoacyl -acyl-carrier-protein synthase II. (EC:2.3.1.41, E.C: 2.3.1.85, 2.3.1.179). C12H22O3 None None None 20588.6 18726.6 35943.9 20169.0 23099.8 18468.8 31762.6 52751.3 14640.2 17858.7 18028.2 13822.5 20103.7 19896.4 31121.6 22011.1 77222.1 18167.2 18752.6 31843.7 17387.7 13617.6 19559.8 19757.0 19895.2 12579.2 24654.5 19592.0 13317.6 21591.6 19650.1 15525.7 11555.5 16399.9 14065.4 19028.0 13009.6 14869.8 18812.1 21479.1 16797.2 19250.2 213.1857325_MZ Tridecanoic acid Un 1.0 None None None None Tridecanoic acid is a short-chain fatty acid. C13H26O2 None None None 37203.4 34731.9 36900.2 25547.4 29787.6 36662.3 37537.4 49277.9 27220.3 31347.7 28381.6 25217.6 31128.8 34603.3 34029.8 27288.1 65082.3 35846.6 31298.5 39456.8 31922.5 25283.9 32683.6 42115.2 26901.4 23555.5 29307.2 31997.0 23121.4 38185.3 27293.7 25125.1 23664.7 32136.7 26038.8 31297.7 24785.1 24649.2 29871.6 33867.9 23957.0 30279.5 213.9645405_MZ Platinum Un 1.0 None None None None Platinum is a rare, dense, malleable, ductile, precious, gray-white transition metal, that is highly resistant to corrosion. Platinum is used in catalytic converters, laboratory equipment, electrical contacts and electrodes, platinum resistance thermometers, dentistry equipment, and jewelry. Pt None None None 3937.02 3730.9 3026.03 3743.21 3271.66 3884.08 4310.67 4667.03 3068.44 3733.26 4240.29 2788.53 3764.51 4128.02 4360.95 4587.67 3772.29 2772.34 3807.47 3581.81 3507.73 2903.31 4923.56 4662.69 3832.34 3101.9 2963.07 3557.02 2907.01 3969.26 3717.85 5160.29 3042.56 3111.15 3774.08 3693.31 3115.37 3524.93 2839.57 4206.76 3841.2 3927.0 214.0485168_MZ Glycerylphosphorylethanolamine Un 1.0 None None None None Glycerylphosphorylethanolamine is a membrane breakdown product resulting from the cleavage of the lipid group from glycerophosphoethanlomine fatty acids (i.e. phosphatidylethanolamine). It acts as a growth stimulant for hepatocytes. C5H14NO6P None None None 244505.0 457421.0 227442.0 317005.0 310346.0 449689.0 323071.0 479972.0 430025.0 507061.0 367666.0 765463.0 183781.0 381421.0 535942.0 566332.0 191055.0 188841.0 350773.0 610305.0 435155.0 625666.0 393132.0 300713.0 278547.0 345712.0 263083.0 211160.0 460857.0 237194.0 521060.0 302710.0 519440.0 174080.0 374932.0 281927.0 288154.0 476626.0 232629.0 618880.0 193396.0 258750.0 214.1081036_MZ Propenoylcarnitine Un 1.0 None None None None none C10H17NO4 None None None 4941.91 5497.49 5302.98 13581.2 5814.15 5501.35 7512.71 8084.81 6109.09 6313.5 7469.25 9033.18 5004.88 5467.78 5889.68 5944.6 7970.08 3915.37 5441.38 5184.71 5422.15 4872.16 7020.57 6552.68 4788.25 4815.03 7074.13 5453.69 4558.82 5551.15 6290.9 4844.32 3995.55 6082.82 5090.35 5827.36 4426.39 5487.21 3053.4 7456.88 4050.23 6107.28 214.1450536_MZ N-Nonanoylglycine Un 1.0 None None None None N-Nonanoylglycine is an acylglycine with C-9 fatty acid group as the acyl moiety. Acylglycines 1 possess a common amidoacetic acid moiety and are normally minor metabolites of fatty acids. Elevated levels of certain acylglycines appear in the urine and blood of patients with various fatty acid oxidation disorders. They are normally produced through the action of glycine N-acyltransferase which is an enzyme that catalyzes the chemical reaction: acyl-CoA + glycine ↔ CoA + N-acylglycine. C11H21NO3 None None None 9023.94 7355.92 8921.8 6425.65 4637.36 6337.66 13845.6 11055.5 4478.82 5529.13 6682.03 3168.22 10071.2 7217.38 5707.05 5025.42 15400.5 9617.44 4962.81 9953.94 6030.15 3749.29 11673.9 9074.2 5005.53 4147.09 5065.67 7892.27 3607.15 8768.32 8870.28 5324.85 3253.08 8821.37 4540.83 6153.4 5071.19 3844.48 4612.85 6014.28 12127.7 5838.55 215.1287446_MZ Undecanedioic acid Un 1.0 None None None None Undecanedioic acid has been found in parts of human aortas with advanced atherosclerotic lesions associated with intercellular matrix macromolecules and specifically with elastin, and may be the result of an increased hydrolysis of esters and (or) a decreased esterification. (PMID: 131675). Undecanedioic acid has been found (among other unusual dicarboxylic acids) in the urine from patients under hopantenate therapy during episodes of Reye's-like syndrome. (PMID: 2331533). C11H20O4 None None None 98559.4 94921.6 19345.7 97453.5 79982.7 118539.0 19346.4 56153.7 50113.3 107879.0 94433.3 10449.9 11375.9 103855.0 88665.0 72111.2 33562.4 11083.0 101250.0 40394.7 108016.0 14058.2 93295.1 128108.0 77643.7 13004.7 84808.2 15761.6 11597.1 106576.0 36279.9 71635.9 8745.17 46571.4 14081.8 96136.8 47796.8 8626.78 49931.7 95949.3 12684.6 102342.0 216.0257699_MZ 3-Hydroxy-2-methylpyridine-4,5-dicarboxylate Un 1.0 None None None None 3-Hydroxy-2-methylpyridine-4,5-dicarboxylate is an intermediate in vitamin B6 metabolism(KEGG ID C04604). It is the third to last step in the synthesis of succinate semialdehyde, which is an intermediate in butanoate metabolism. 3-Hydroxy-2-methylpyridine-4,5-dicarboxylate is generated from 2-Methyl-3-hydroxy-5-formylpyridine-4-carboxylate and is then converted to 3-hydroxy-2-methylpyridine-5-carboxylate. C8H7NO5 None None None 7843.57 8353.6 7858.34 5023.68 6593.08 11017.6 6575.23 6921.25 6426.84 7523.11 6826.5 8879.67 5512.85 6577.16 6936.42 10793.9 5955.78 6263.34 6158.7 7365.23 6528.21 8179.37 7112.93 8000.08 5890.16 8104.11 6495.73 7313.18 8058.81 9048.71 8244.12 8351.15 6746.13 6831.95 9211.88 7510.27 6538.06 8344.88 6065.23 7065.22 5359.14 5944.89 216.0987188_MZ N-a-Acetylcitrulline Un 1.0 None None None None N-a-Acetylcitrulline is an N-acetylated metabolite of citrulline that is part of the arginine biosynthetic pathway. Arginine biosynthesis is notable for its complexity and variability at the genetic level, and by its connection with several other pathways, such as pyrimidine and polyamine biosynthesis, and certain degradative pathways. The initial steps of the arginine biosynthetic pathways proceed via N-acetylated intermediates. The presumed reason for this is that the acetylation prevents the spontaneous cyclization of glutamate derivatives, which leads to proline biosynthesis. N-acetyl-L-ornithine can be transcarbamylated directly by the enzyme acetylornithine transcarbamylase, resulting in N-acetyl-L-citrulline. The enzyme acetylornithine deacetylase can accept N-acetyl-L-citrulline as a substrate, and can deacetylate it into citrulline. N-a-Acetylcitrulline is found in cases of deficiency of the urea cycle enzyme argininosuccinate synthase (EC 6.3.4.5) that leads to increased concentrations of citrulline and N-acetylcitrulline in the urine. (PMID: 14633929). C8H15N3O4 None None None 35045.2 33691.1 32691.4 64295.4 20376.5 31405.8 22842.5 29686.4 33751.3 16981.5 22293.1 33875.9 15774.7 26621.0 26307.1 37392.1 29702.8 15667.3 19997.5 18991.2 33319.3 33441.4 23206.1 22253.5 33584.2 19079.7 27578.1 24587.2 38986.5 42696.4 35629.6 24009.4 16645.3 23425.4 62849.7 31610.7 39487.3 35757.9 19401.7 26931.9 11756.5 21546.4 216.1338168_MZ Gamma-glutamyl-L-putrescine Un 1.0 None None None None Gamma-glutamyl-L-putrescine is involved in the putrescine II degradation pathway. γ-glutamyl-L-putrescine reacts with H2O and O2 to produce γ-glutamyl-γ-aminobutyraldehyde, H2O2, and NH4+. γ-glutamyl-L-putrescine is formed from an ATP-driven reaction between putrescine, L-glutamate. C9H19N3O3 None None None 15615.8 16528.6 8673.82 19104.6 14461.2 18866.1 6578.92 10754.9 15549.0 16418.5 15490.6 10744.4 4952.7 16509.5 15932.6 14449.1 8231.02 3237.14 15424.9 7104.84 15757.6 14572.3 15576.8 18342.1 14334.7 7781.32 13846.9 9277.36 13246.5 16560.0 8848.26 13365.8 6204.01 11615.5 15438.8 18061.4 14464.7 9571.77 10625.0 20121.2 3646.31 16471.9 216.1681098_MZ Deoxyhypusine Un 1.0 None None None None Deoxyhypusine is an amino acid derivative of the unusual amino acid known as hypusine. It is a substrate of Deoxyhypusine synthase which catalyzes the cleavage of the polyamine spermidine and transfer of its 4-aminobutyl moiety to the ε-amino group of one specific lysine residue of the eIF-5A precursor to form deoxyhypusine and 1,3-diaminopropane. By the addition of a hydroxyl group to the deoxyhypusine residue deoxyhypusine hydroxylase mediates the formation of hypusine. (Wikipedia). C10H23N3O2 None None None 1959.08 1822.29 1682.52 1991.01 1685.13 1723.04 2453.1 2472.19 1441.77 1581.98 1677.86 1426.85 1914.7 1808.82 1764.32 1400.33 2708.47 1430.0 1614.78 1984.82 1645.9 1373.49 1741.76 2042.61 1427.84 1207.13 1376.8 1694.2 1336.91 1969.55 1554.24 1182.58 1055.26 1588.84 1691.44 1974.99 1237.52 1524.04 1499.8 2009.05 1595.36 1659.94 218.1035646_MZ Pantothenic acid Un 1.0 None None None None Pantothenic acid, also called vitamin B5, is a water-soluble vitamin required to sustain life. Pantothenic acid is needed to form coenzyme-A (CoA), and is thus critical in the metabolism and synthesis of carbohydrates, proteins, and fats. Its name is derived from the Greek pantothen meaning from everywhere and small quantities of pantothenic acid are found in nearly every food, with high amounts in whole grain cereals, legumes, eggs, meat, and royal jelly. C9H17NO5 None None None 132592.0 172548.0 219666.0 274222.0 170348.0 166040.0 170600.0 138916.0 211706.0 154567.0 158791.0 196832.0 107945.0 215208.0 179940.0 223608.0 155759.0 118629.0 145785.0 157528.0 248697.0 166761.0 283079.0 149707.0 212374.0 192664.0 167850.0 172050.0 199029.0 241216.0 249462.0 249393.0 143341.0 136878.0 216605.0 110000.0 156329.0 207625.0 125743.0 196593.0 144662.0 138961.0 219.0855881_MZ 1-Hydroxypyrene Un 1.0 None None None None 1-Hydroxypyrene is a metabolite of the noncarcinogen pyrene found in urine that is always a component of PAH mixtures. 1-hydroxypyrene is an accepted biomarker of carcinogenic Polycyclic aromatic hydrocarbons (PAH) dose(PMID: 15159317). PAH are a diverse group of environmental carcinogens formed during the incomplete combustion of organic matter. PAHs are believed to play an important role as causes of human cancer, particularly in certain occupational settings and in cigarette smokers. (PMID: 15247141). C16H12O None None None 9774.84 8908.66 14396.0 10652.8 9996.91 8963.82 10566.4 18036.8 8032.6 8540.43 8800.52 7587.24 6035.33 9660.64 14708.6 11174.0 22550.2 6827.54 8558.19 9601.45 8130.08 7688.69 7986.3 9310.64 8462.87 7510.88 10420.3 8573.7 6612.06 10674.2 7792.5 9059.62 7010.13 7328.55 7637.89 9975.79 7092.7 6981.98 6944.6 10693.7 5179.9 8932.25 220.0283729_MZ S-(3-oxo-3-carboxy-n-propyl)cysteine Un 1.0 None None None None S-(3-oxo-3-carboxy-n-propyl)cysteine is a cystathionine metabolite found in the urine of cystathioninuria patients; has a priming effect on 02- generation in human neutrophils (Biochemical and Biophysical Research Communications. Volume 269, Issue 2 , 16 March 2000, Pages 297-301 ). C7H11NO5S None None None 9708.83 9099.2 10364.4 10594.0 12419.8 10876.6 10873.7 8342.95 10181.9 9982.21 8978.96 9449.64 7756.94 9873.8 12261.7 10780.1 9674.68 10910.4 13202.6 17577.1 9756.81 9437.55 10245.8 10095.3 13056.3 8944.01 12354.4 8578.16 9885.41 10479.4 16765.1 9627.85 10595.1 14699.1 9033.42 10830.9 10356.7 9826.04 7747.34 10151.5 21464.2 9521.05 220.0825181_MZ N-Acetylgalactosamine Un 1.0 None None None None Acetylgalactosamine is an important constituent of brain heteropolysaccharides (glycoproteins). The concentration of the N-acetylgalactosamine-containing glycoproteins in the 3-year-old cerebral gray matter from human brain is 7-15 times greater than in 8-year old tissue and 15-30 times greater than in 72-year-old tissue. (PMID 1207868). Acetylgalactosamine patterns of the composition of the soluble glycoproteins from endoscopic mucosal biopsies tends to decrease in the tumor area in cancer of the stomach (compared with the antrum and corpus of control stomachs). (PMID: 7151277). Chondroitin 6-sulfotransferase (C6ST) is the key enzyme in the biosynthesis of chondroitin 6-sulfate, a glycosaminoglycan implicated in chondrogenesis, neoplasia, atherosclerosis, and other processes. C6ST catalyzes the transfer of sulfate from 3'-phosphoadenosine 5'-phosphosulfate to carbon 6 of the N- Acetylgalactosamine residues of chondroitin. (PMID: 9639683). C8H15NO6, N-Acetylmannosamine None None None 20354.8 23100.3 26691.7 34246.1 28540.0 23108.3 19645.5 25218.9 26689.8 20801.6 32329.5 25760.1 27182.1 20832.8 27999.7 24225.1 23898.0 22584.5 22651.7 23578.6 27112.6 20732.8 28788.8 26360.2 18689.8 24982.7 21455.3 25467.4 21340.0 28100.1 20080.2 28558.4 17079.8 22629.9 22346.6 36028.2 17673.9 28499.8 15801.7 30041.6 17459.0 19101.3 220.1198058_MZ Dihydrozeatin Un 1.0 None None None None Dihydrozeatin is an intermediate in Zeatin biosynthesis. It is converted from dihydrozeatin riboside and is then converted to dihydrozeatin-O-glucoside via the enzyme glycosyltransferases (EC 2.4.1.- ). C10H15N5O None None None 1251.35 1332.11 1473.15 1538.77 1431.72 1354.8 1346.1 1397.57 1376.83 1217.92 1442.21 1199.65 1277.89 1440.02 1473.59 1434.34 1550.81 945.591 1170.31 1289.42 1372.34 1329.16 1588.42 1354.46 1379.54 1197.03 1364.92 1356.01 1276.8 1545.3 1365.24 1313.08 1189.96 1132.96 1342.55 1344.39 1057.06 1363.22 994.795 1455.92 1045.52 1158.94 221.0667396_MZ Ethyl glucuronide Un 1.0 None None None None Ethyl glucuronide is a natural human metabolite of Ethanol generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys. C8H14O7 None None None 596843.0 565290.0 769149.0 581724.0 298092.0 490602.0 908348.0 749347.0 584313.0 558100.0 528509.0 994357.0 272570.0 206143.0 520819.0 246587.0 447130.0 212127.0 266131.0 627653.0 542676.0 430446.0 322987.0 430604.0 518491.0 765971.0 488994.0 444236.0 452380.0 603946.0 542118.0 399590.0 398636.0 445417.0 376824.0 309211.0 547839.0 586598.0 110482.0 507312.0 354643.0 497042.0 222.0433147_MZ 4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid Un 1.0 None None None None 4-(2 Amino-3-hydroxyphenyl)-2,4-dioxobutanoate is found in the tryptophan metabolic pathway and is an intermediate in tryptophan degradation [Kegg: C05645]. More specifically it is an intermediate in the conversion of 3-hydroxy-L-kynurenine to xanthurenate. The conversion is catalyzed by kynurenine aminotransferase (EC 2.6.1.7). C10H9NO5 None None None 8854.07 12859.1 10802.5 8953.84 7978.27 11613.3 8071.2 8641.95 8897.64 8993.13 9874.78 10302.0 5909.34 9942.41 8092.4 12069.5 11241.9 7829.52 7745.19 7580.34 12158.1 9125.93 9588.58 8497.02 8511.08 7948.23 8466.5 9783.61 9740.58 12017.8 10189.9 9468.64 6977.71 9676.65 11385.2 8834.31 9475.86 8827.62 5185.28 8503.53 6406.46 6955.95 223.0714806_MZ Hydroxykynurenine Un 1.0 None None None None Hydroxykynurenine is a free radical generator and a bioprecursor quinolinic acid which is a endogenous excitotoxin (PMID 16697652). It is a product of enzyme kynurenine 3-monooxygenase in the tryptophan catabolism pathway (Reactome http://www.reactome.org). C10H12N2O4, L-3-Hydroxykynurenine, 5-Hydroxykynurenine None None None 16419.4 14928.8 18684.2 15733.2 10864.1 14713.3 20589.3 17309.0 14970.4 13943.1 14816.8 20767.2 9389.81 9620.09 13805.9 10490.0 13564.2 8962.42 9970.64 15574.3 15171.6 11780.8 11387.9 13085.8 13709.0 17653.0 12967.2 12801.5 12850.3 16757.4 14395.5 12412.6 10978.4 12200.8 11823.3 11555.6 13478.2 14259.4 5548.72 13947.5 11226.0 13140.1 223.1701557_MZ 5,8-Tetradecadienoic acid Un 1.0 None None None None 5,8-Tetradecadienoic acid is an intermediate of unsaturated fatty acid oxidation. An increase of 5,8-Tetradecadienoic acid in plasma is associated with acyl-CoA dehydrogenase deficiency disorders. (PMID 7586519). C14H24O2 None None None 6557.61 6662.79 6158.75 18882.0 7877.7 7010.68 8073.99 7109.7 6811.29 8739.05 9699.42 7056.3 4867.02 7909.3 7321.06 5451.79 7535.88 5820.59 5517.66 5295.3 6704.65 5680.57 8060.45 7546.27 6701.08 6868.29 6765.83 7236.31 7029.03 7264.41 5878.52 5594.03 6578.82 5978.61 9853.96 7512.3 5525.8 8135.25 5905.1 7323.35 6246.53 7021.44 224.0577845_MZ Lipoamide Un 1.0 None None None None Lipoamide is the oxidized form of glutathione. (PMID:8957191). Lipoamide is a trivial name for 6,8-dithiooctanoic amide. It is 6,8-dithiooctanoic acid's functional form where the carboxyl group is attached to protein (or any other amine) by an amide linkage (containing -NH2) to an amino group. Lipoamide forms a thioester bond, oxidizing the disulfide bond, with acetaldehyde (pyruvate after it has been decarboxylated). It then transfers the acetaldehyde group to CoA which can then continue in the TCA cycle. (Wikipedia). Lipoamide is an intermediate in glycolysis/gluconeogenesis, citrate cycle (TCA cycle), alanine, aspartate and pyruvate metabolism, and valine, leucine and isoleucine degradation (KEGG:C00248). It is generated from dihydrolipoamide via the enzyme dihydrolipoamide dehydrogenase (EC:1.8.1.4) and then converted to S-glutaryl-dihydrolipoamide via the enzyme oxoglutarate dehydrogenase (EC:1.2.4.2). C8H15NOS2 None None None 9238.69 8117.96 9216.84 9823.77 9068.38 9374.79 10651.4 8165.61 8584.82 8782.43 8685.73 9869.82 6848.7 8807.83 8930.27 9263.39 11488.6 7071.37 8244.01 8196.16 9030.17 8514.28 9025.28 8783.09 7621.36 7514.7 8586.64 8490.08 7332.17 10423.2 9016.77 8763.46 7137.14 7671.48 7942.88 8460.03 6879.1 8066.52 5679.26 8245.77 7741.08 7172.94 225.0632346_MZ 5-Acetylamino-6-formylamino-3-methyluracil Un 1.0 None None None None 5-Acetylamino-6-formylamino-3-methyluracil participates in Caffeine metabolism. 5-Acetylamino-6-formylamino-3-methyluracil is converted from paraxanthine via arylamine N-acetyltransferase [EC:2.3.1.5]. C8H10N4O4 None None None 18550.0 17122.6 17296.0 15859.3 15182.4 21917.3 16393.3 15115.7 16007.0 17889.8 15862.3 18686.0 21602.9 18699.0 16891.8 22338.3 13652.0 17196.8 16690.4 16839.8 18154.4 15400.2 15545.4 16413.8 14325.1 13894.1 16114.6 16136.6 16885.2 17953.4 14570.3 18013.3 15945.7 15336.5 19675.0 19266.8 14152.2 15005.1 12286.4 16581.0 16159.8 16104.9 225.0994027_MZ Carnosine Un 1.0 None None None None Carnosine (beta-alanyl-L-histidine) is found exclusively in animal tissues. It is a dipeptide of the amino acids beta-alanine and histidine. Carnosine has the potential to suppress many of the biochemical changes (e.g., protein oxidation, glycation, AGE formation, and cross-linking) that accompany aging and associated pathologies (PMID 16804013). It is highly concentrated in muscle and brain tissues. Some autistics patients take it as a dietary supplement, and attribute an improvement in their condition to it. Supplemental carnosine may increase corticosterone levels. This may explain the hyperactivity seen in autistic subjects at higher doses. Carnosine also exhibits some antioxidant effects. The antioxidant mechanism of carnosine is attributed to its chelating effect against metal ions, superoxide dismutase (SOD)-like activity, ROS and free radicals scavenging ability (PMID 16406688). C9H14N4O3, (6R)-6-(L-Erythro-1,2-Dihydroxypropyl)-5,6,7,8-tetrahydro-4a-hydroxypterin None None None 5876.89 5540.74 11597.4 7975.77 5044.08 6378.17 5912.66 5141.41 5769.11 4692.52 5318.01 6017.73 4115.83 5833.75 5948.49 7233.23 5382.94 3473.7 4699.91 4255.98 6085.86 7563.89 5046.26 4612.07 5231.3 8966.88 5582.66 9537.43 10372.7 10161.4 5286.87 5674.46 3662.97 4944.02 22354.0 5753.82 5473.5 4774.19 4352.54 5428.38 3381.01 4943.22 226.0122417_MZ L-Glutamic acid 5-phosphate Un 1.0 None None None None L-Glutamic acid 5-phosphate is an intermediate in the urea cycle and the metabolism of amino groups. It is a substrate of aldehyde dehydrogenase 18 family, member A1 [EC:2.7.2.11 1.2.1.41] (KEGG)In citrulline biosynthesis, it is a substrate of the enzyme glutamate-5-semialdehyde dehydrogenase [EC 1.2.1.41] and in proline synthesis it is a substrate of the enzyme Glutamate 5-kinase [EC 2.7.2.11] (BioCyc). C5H10NO7P None None None 23142.4 23055.5 24175.6 21009.4 35931.9 18468.2 26201.1 23932.2 27824.7 16823.4 24208.5 20787.0 21530.3 22993.5 27484.8 21731.5 34617.2 25169.0 16848.9 18756.0 21301.5 17089.9 22567.1 20407.9 25427.1 15261.6 23933.9 23193.9 26720.8 19393.6 21971.3 22485.6 20813.4 15335.1 25609.5 19547.1 17395.0 27096.4 15455.1 23521.5 22278.9 18034.1 226.0836025_MZ Deoxycytidine Un 1.0 None None None None Deoxycytidine is one of the principal nucleosides of DNA composed of cytosine and deoxyribose. A nucleoside consists of only a pentose sugar linked to a purine or pyrimidine base, without a phosphate group. When N1 is linked to the C1 of deoxyribose, deoxynucleosides and nucleotides are formed from cytosine and deoxyribose; deoxycytidine monophosphate (dCMP), deoxycytidine diphosphate (dCDP), deoxycytidine triphosphate (dCTP). CTP is the source of the cytidine in RNA (ribonucleic acid) and deoxycytidine triphosphate (dCTP) is the source of the deoxycytidine in DNA (deoxyribonucleic acid). C9H13N3O4 None None None 11986.5 12149.5 11592.9 7336.74 9011.96 13380.3 9431.01 10942.4 8246.61 8268.59 9037.54 10683.5 7496.16 11110.7 9530.79 14850.3 9810.71 8421.64 8310.42 9576.65 10273.5 10672.7 8444.26 11535.5 8540.27 10351.7 9840.84 9484.68 11198.0 11767.7 11969.4 10482.2 9815.67 8674.6 12659.6 9817.66 9582.3 10537.4 9906.63 8744.12 8610.64 8613.12 227.0788118_MZ L-Kynurenine Un 1.0 None None None None Kynurenine is a metabolite of the amino acid tryptophan used in the production of niacin. L-kynurenine is a central compound of the pathway of tryptophan metabolism pathway since it can change to the neuroprotective agent kynurenic acid or to the neurotoxic agent quinolinic acid. The break-up of these endogenous compounds' balance can be observable in many disorders. It can occur in neurodegenerative disorders, such as Parkinson's disease, Huntington's and Alzheimer's disease, in stroke, in epilepsy, in multiple sclerosis, in amyotrophic lateral sclerosis, and in mental failures, such as schizophrenia and depression. C10H12N2O3, Formyl-5-hydroxykynurenamine None None None 3465.1 2655.96 2869.5 2303.35 2429.27 3524.82 3023.24 2612.71 2418.14 2960.87 3141.64 2450.44 2046.24 2575.29 3550.13 8737.34 2171.9 3107.64 2763.3 2229.21 3012.44 2561.65 2611.01 2599.0 3155.32 3508.57 2757.92 2675.13 2900.91 4222.75 16170.2 3969.5 2530.49 2187.75 2957.44 3053.85 2152.64 2487.55 3269.28 2846.51 2135.39 2671.66 227.1039470_MZ Prolylhydroxyproline Un 1.0 None None None None Prolylhydroxyproline is a dipeptide. Prolylhydroxyproline is a marker of bone collagen degradation, showing high sensitivity for the diagnosis of osteoporosis. Prolylhydroxyproline has been suggested as a possible alternative to hydroxyproline determination in bone resorption studies. Prolylhydroxyproline is one of the iminodipeptides present in the urine of patients with prolidase deficiency. Prolidase (X-Pro dipeptidase EC 3.4. 13.9) splits iminodipeptides containing C-terminal proline or hydroxyproline (X-Pro or X-Hyp) to X+Pro or X+Hyp. Prolidase deficiency is a rare autosomal recessive disease characterized by chronic ulcerative dermatitis and mental retardation. These patients excrete large amounts of iminodipeptides containing C-terminal proline in the urine due to hereditary prolidase deficiency. (PMID: 12636053, 11863289, 2387877, 1874885, 9586797). C10H16N2O4 None None None 11010.7 9867.98 12725.2 10069.7 11361.3 14083.4 12517.4 14717.0 8713.92 9799.72 9965.02 11122.8 8591.5 9979.47 10764.5 12591.5 14599.8 10440.7 12343.9 11768.1 9539.92 9382.81 11682.1 10384.1 9841.6 10452.7 12899.9 11850.5 10965.4 11847.3 10213.7 10398.9 8301.78 8699.33 10638.5 12541.6 8217.4 9548.41 9480.35 11092.5 9939.18 10396.0 227.1287627_MZ Traumatic acid Un 1.0 None None None None Traumatic acid is a monounsaturated dicarboxylic acid naturally ocurring in plants. The compound was first isolated from wounded bean plants by American chemists James English Jr. and James Frederick Bonner and Dutch scientist Aire Jan Haagen-Smit in 1939. Traumatic acid is a potent wound healing agent in plants (wound hormone) that stimulates cell division near a trauma site to form a protective callus and to heal the damaged tissue. It may also act as a growth hormone, especially in inferior plants (e.g. algae). Traumatic acid is biosynthesized in plants by non-enzimatic oxidation of traumatin (12-oxo-trans-10-dodecanoic acid), another wound hormone. At normal conditions, traumatic acid is a solid, crystalized, water insoluble substance. C12H20O4 None None None 21554.5 23380.8 30960.6 27106.3 32416.0 30624.2 31592.7 38880.0 18512.1 23676.7 29623.7 19864.9 16698.9 28594.7 32315.2 25953.7 49664.7 11250.9 18890.4 22806.2 20573.5 15495.9 25500.4 22080.4 23495.9 18419.1 30213.4 19998.1 15053.3 27353.8 19029.8 19555.2 18716.5 16912.4 17868.5 19570.8 15245.0 18885.6 15176.9 25189.8 13694.8 18366.4 227.1396677_MZ L-leucyl-L-proline Un 1.0 None None None None L-leucyl-l-proline is a proteolytic breakdown product of larger proteins. It belongs to the family of Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. It is found in urine (PMID: 3782411). C11H20N2O3, L-isoleucyl-L-proline None None None 8697.7 9253.17 10351.0 9730.19 10429.3 11149.4 9724.39 10059.2 8288.73 8120.54 10117.3 10056.0 7002.96 9113.83 9184.55 10059.0 11608.9 5064.38 7844.22 8032.6 8432.78 8410.75 9395.92 8433.07 8212.48 8260.5 10383.0 8838.51 8694.55 8598.48 8580.3 7643.67 8319.41 7042.83 10671.8 9692.55 7234.69 8780.47 5055.77 9714.83 5950.65 7766.87 227.2014931_MZ Myristic acid Un 1.0 None None None None Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. It is used to synthesize flavor and as an ingredient in soaps and cosmetics. (From Dorland, 28th ed). Myristic acid is also commonly added to a penultimate nitrogen terminus glycine in receptor-associated kinases to confer the membrane localisation of the enzyme. this is achieved by the myristic acid having a high enough hydrophobicity to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of the eukaryotic cell.(wikipedia). C14H28O2, 2_6_10-Trimethylundecanoic acid None None None 275146.0 272584.0 242714.0 236968.0 230918.0 293243.0 284611.0 317534.0 246571.0 280658.0 265767.0 251965.0 271370.0 281265.0 257101.0 206644.0 297799.0 400616.0 239696.0 315742.0 253721.0 230719.0 255022.0 300513.0 241113.0 226890.0 215611.0 311850.0 224006.0 285349.0 215148.0 196847.0 253122.0 256265.0 220444.0 290608.0 216108.0 250533.0 252796.0 255052.0 243740.0 270504.0 228.0834021_MZ Ergothioneine Un 1.0 None None None None Ergothioneine is a naturally occurring metabolite of histidine that has antioxidant properties. -- Pubchem. Ergothioneine is a product of plant origin that accumulates in animal tissues. Ergothioneine is biosynthesized exclusively by fungi and mycobacteria and is captured by plants through their roots. As an ingredient of human food, ET is distributed very unevenly. By far, the highest levels of Ergothioneine have been found in mushrooms (0.1-1 mg/g dried material). Ergothioneine is rapidly cleared from the circulation and then avidly retained with minimal metabolism: the whole-body half-life of ingested Ergothioneine in rats is 1 month. The content of Ergothioneine varies greatly among tissues and is strongly dependent on its dietary level. In addition to erythrocytes and bone marrow, high Ergothioneine levels have also been found in seminal fluid. The precise physiological role of ET has remained elusive since its discovery in 1909. It is known that Ergothioneine is a powerful scavenger of hydroxyl radicals and an inhibitor of iron or copper ion-dependent generation of hydroxyl radicals from hydrogen peroxide (H2O2). A specific ergothioneine transporter has recently been identified (gene symbol SLC22A4 - PMID: 15795384). Ergothioneine appears to play a pivotal protective role in monocytes, because the occurrence of rheumatoid arthritis and Crohn's disease has very recently been linked to variant ergothioneine transporter genes (PMID: 15795384). SLC22A4 is highly expressed in the kidney, where it is thought to aid in active secretion of organic cations, and may facilitate the active reabsorption of ergothioneine. C9H15N3O2S None None None 20521.0 16456.6 18858.4 28510.3 14181.8 21454.3 15541.8 14684.8 12798.9 15739.3 18711.8 16483.0 13895.8 20428.4 11348.5 25107.1 19917.7 13638.9 17858.6 13487.6 10782.0 12461.3 19626.6 18776.9 15641.0 14991.0 20679.1 19854.4 12300.3 17581.5 21393.4 14717.3 11820.8 13162.3 15627.1 20153.5 10551.5 15331.3 3192.54 16554.7 21744.5 13441.6 228.1244212_MZ Butenylcarnitine Un 1.0 None None None None none C11H19NO4 None None None 7076.68 7386.3 5871.31 9397.39 5034.35 7461.92 7014.06 6857.84 3969.83 6254.13 7964.67 4121.99 6976.76 5570.1 4429.52 8231.73 6185.37 7422.83 5271.3 6090.86 7350.96 3168.07 7275.25 6666.93 5384.46 4178.04 7011.18 5687.45 4987.01 6861.7 8318.16 6827.09 3390.59 5696.71 4684.68 6920.14 5144.74 4148.99 3188.52 5141.73 6091.66 6425.4 228.1604245_MZ N-Decanoylglycine Un 1.0 None None None None N-Decanoylglycine is an acylglycine with C-10 fatty acid group as the acyl moiety. Acylglycines 1 possess a common amidoacetic acid moiety and are normally minor metabolites of fatty acids. Elevated levels of certain acylglycines appear in the urine and blood of patients with various fatty acid oxidation disorders. They are normally produced through the action of glycine N-acyltransferase which is an enzyme that catalyzes the chemical reaction: acyl-CoA + glycine ↔ CoA + N-acylglycine. C12H23NO3 None None None 13334.7 8561.34 12727.0 10402.4 4927.43 8897.51 20949.2 15871.7 4691.01 5992.93 11838.1 3500.07 16191.6 9916.84 5926.73 5332.91 24009.0 11823.9 4888.6 13286.0 7169.48 3130.98 17870.4 13528.9 6099.27 4843.04 5788.14 10477.5 3742.55 11415.7 14085.3 7679.83 3113.9 12395.3 5624.33 6796.56 4687.36 3889.87 4495.47 7563.76 16754.4 7314.72 229.0116768_MZ D-Ribulose 5-phosphate Un 1.0 None None None None D-Ribulose 5-phosphate is a metabolite in the Pentose phosphate pathway, Pentose and glucuronate interconversions, and in the Riboflavin metabolism (KEGG). C5H11O8P, Xylulose 5-phosphate, Ribose 1-phosphate, D-Ribose 5-phosphate, D-Xylulose 1-phosphate, D-Arabinose 5-phosphate, Beta-L-arabinose 1-phosphate None None None 152056.0 143281.0 172880.0 117676.0 181449.0 226350.0 217687.0 131370.0 196033.0 202756.0 176436.0 204597.0 201773.0 144850.0 213238.0 177432.0 168002.0 245795.0 236376.0 178040.0 188128.0 155707.0 189392.0 174852.0 176791.0 171881.0 206740.0 198360.0 165626.0 218315.0 134663.0 178302.0 150118.0 137434.0 171167.0 237943.0 177062.0 162448.0 145727.0 214283.0 206208.0 216172.0 229.0718180_MZ Sedoheptulose Un 1.0 None None None None Sedoheptulose is a ketoheptose, a monosaccharide with seven carbon atoms and a ketone functional group. It is one of the few heptoses found in nature. Sedoheptulose is a seven-carbon ketose sugar originally found in Sedum spectabile, a common perennial garden plant. Later it was shown to be widely distributed in the plants of the Crassulaceae family. The Crassulaceae, or orpine family, is a family of dicotyledons. They store water in their succulent leaves. They are found worldwide, but mostly occur in the Northern Hemisphere and southern Africa, typically in dry and/or cold areas where water may be scarce. The family includes about 1,400 species in 33 genera. As a result, this sugar is often found to be part of the human diet. This sugar, D-sedoheptulose (I), is a significant intermediary compound in the cyclic regeneration of D-ribulose. It also plays an important role as a transitory compound in the cyclic regeneration of D-ribulose for carbon dioxide fixation in plant photosynthesis. -- www.accessscience.com. C7H14O7 None None None 11535.7 10658.7 21287.1 14155.2 14346.8 12807.0 17201.9 25558.6 9065.64 10765.9 10643.9 9889.31 11697.8 10675.0 21998.4 20072.1 38694.3 9050.67 10602.0 16021.4 9873.03 8992.8 10975.1 10370.1 13023.2 9276.02 15234.7 12115.0 9489.16 13208.2 13680.7 15296.7 8061.83 8392.91 10205.7 12138.6 9162.94 9147.46 9779.77 13496.9 8806.64 11990.3 229.1441637_MZ Dodecanedioic acid Un 1.0 None None None None Dodecanedioic acid is a dicarboxylic acid which is water soluble and involves in a metabolic pathway intermediate to those of lipids and carbohydrates. (PMID 9591306). Dodecanedioid acid is an indicator of hepatic carnitine palmitoyltransferase I (CPT IA) deficiency. CPT IA deficiency is characterized by hypoketotic dicarboxylic aciduria with high urinary levels of dodecanedioic acid. This C12 dicarboxylic aciduria suggests that carnitine palmitoyltransferase I may play a role in the uptake of long-chain dicarboxylic acids by mitochondria after their initial shortening by beta-oxidation in peroxisomes. (PMID: 16146704). C12H22O4 None None None 27368.3 24773.5 23430.8 25089.4 21405.9 22927.1 24875.1 35518.4 15744.5 21178.1 20851.5 10416.6 15943.2 24635.5 25956.7 21491.9 48417.8 12000.0 19514.9 21687.2 24203.5 10179.8 21325.7 28856.5 21280.1 11194.2 22542.7 15033.4 9871.54 29622.7 17152.2 17742.2 9180.86 16912.0 11715.6 25499.0 14984.3 9353.23 16940.3 25010.0 12807.1 22419.7 230.0641579_MZ N2-Succinyl-L-glutamic acid 5-semialdehyde Un 1.0 None None None None N2-Succinyl-L-glutamic acid 5-semialdehyde is a substrate for Succinate semialdehyde dehydrogenase (mitochondrial) and Ornithine aminotransferase (mitochondrial). C9H13NO6 None None None 4732.52 4186.16 4556.04 4059.75 4121.92 6343.8 4388.96 4374.43 4198.76 4321.99 4348.25 4171.39 3871.79 4611.86 4669.09 7373.69 3845.27 3929.56 4099.81 4777.33 4063.07 4075.51 4884.37 4709.13 4209.52 3855.21 4315.64 4305.34 4269.44 5819.92 4916.3 5592.0 4122.0 3636.47 4309.15 4458.2 3790.31 4048.39 3075.52 4682.43 3617.44 3638.81 230.0832054_MZ 3-Methoxytyrosine Un 1.0 None None None None 3-Methoxytyrosine is one of the main biochemical markers for Aromatic L-amino acid decarboxylase (AADC, EC 4.1.1.28) deficiency, an inborn error of metabolism that affects serotonin and dopamine biosynthesis. Patients are usually detected in infancy due to developmental delay, hypotonia, and extrapyramidal movements. Diagnosis is based on an abnormal neurotransmitter metabolite profile in CSF and reduced AADC activity in plasma. 3-methoxytyrosine is elevated in CSF, plasma, and urine. (PMID 1357595, 1281049, 16288991). C10H13NO4, Methyldopa None None None 4480.24 4540.44 4451.46 3971.39 4183.27 5033.92 4121.14 4108.9 3646.61 3547.96 3936.06 3647.86 3433.8 4465.94 4078.5 5271.83 5281.86 3705.19 4135.8 3588.38 4426.78 3455.88 4231.73 4435.16 3666.55 3397.47 4109.58 3916.81 3380.95 4942.02 4179.03 4143.37 3057.66 3205.7 3858.72 4506.31 3013.52 3106.29 2431.53 3993.85 3712.21 3701.75 230.1505597_MZ Gamma-Aminobutyryl-lysine Un 1.0 None None None None g-Aminobutyryl-lysine is a dipeptide present in human brain. This dipeptide occurs in much higher concentrations in human brain than in the brains of lower mammals. (PMID 5559257 ). Adult brain and cerebrospinal fluid a-(g-aminobutyryl)-lysine levels and adult brain homocarnosine levels are higher than those found in children. (PMID 5031796 ). C10H21N3O3 None None None 10223.1 14067.9 11623.0 13949.3 13414.6 11331.3 13038.6 12020.0 10597.9 13095.4 11988.0 10424.0 8503.78 10945.2 13218.6 13003.4 14864.9 8849.09 10371.8 10296.0 13893.8 10747.2 12251.4 12499.5 12965.6 10952.4 14959.5 9427.87 9943.14 12143.1 10992.1 11906.3 9083.94 10896.6 15298.1 10474.4 10046.0 10588.9 7964.71 12199.5 10309.7 10791.2 231.0987029_MZ 4-(Glutamylamino) butanoate Un 1.0 None None None None 4-(Glutamylamino) butanoate is a polyamine that is an intermediate in putrescine degradation II. Polyamines (the most common of which are putrescine , spermidine , and spermine ), a group of positively charged small molecules present in virtually all living organisms, have been implicated in many biological processes, including binding to nucleic acids, stabilizing membranes, and stimulating several enzymes. Although polyamines are clearly necessary for optimal cell growth, a surplus of polyamines can cause inhibition of growth and protein synthesis, and thus a balance is desired between the production and breakdown of polyamines. In putrescine degradation II, 4-(Glutamylamino) butanoate is a substrate for gamma-glutamyl-gamma-aminobutyrate hydrolase (puuD) and can be generated from the hydrolysis of gamma-glutamyl-gamma-aminobutyraldehyde. C9H16N2O5, N2-Succinyl-L-ornithine None None None 19220.2 21781.0 29074.5 45619.3 25266.9 24141.4 23323.8 38411.7 23040.3 23040.7 29986.2 27710.8 15687.8 25393.0 31439.9 20658.7 30585.4 10122.4 17940.0 17895.4 24827.4 23294.7 30262.5 22582.4 24384.4 32745.6 23206.7 21136.3 27325.6 21522.1 26558.9 28090.3 18337.9 24468.9 27678.7 24779.0 27426.0 27064.1 14806.9 30335.9 12624.9 19732.9 231.1369919_MZ Spermic acid 2 Un 1.0 None None None None Spermic acid 2 is a diamide which is identified as urinary metabolites. of putrescine and spermine, and was subsequently identified and quantified. in urines of healthy persons and cancer patients. C10H20N2O4 None None None 15767.2 20027.6 19190.7 21334.6 22380.2 20489.4 15146.6 15820.4 18785.0 16861.4 23742.0 21584.7 9616.38 22499.6 20321.3 16672.5 17075.7 7204.28 13300.4 10699.4 18799.9 19707.7 18423.8 15734.5 16480.7 19891.9 19558.3 17925.5 18376.2 17837.8 15989.3 15407.8 18220.6 13782.9 21237.8 17592.3 15525.7 20643.1 8609.86 19417.7 8195.61 13709.2 232.1189017_MZ Hydroxypropionylcarnitine Un 1.0 None None None None none C10H19NO5 None None None 3950.0 3593.98 4871.25 16363.0 5838.51 4604.19 8032.8 7352.09 5772.69 5522.11 7777.03 4208.85 3280.27 4140.51 5753.56 4330.77 11031.4 2923.88 4201.29 3410.86 4230.04 3190.11 7092.73 4994.79 4222.38 3714.65 6608.18 4337.82 3444.76 4456.33 5680.75 5099.21 2987.45 5375.6 5383.22 4675.43 3734.32 5084.24 2291.91 6704.87 2920.28 4551.91 232.1725326_MZ Hypusine Un 1.0 None None None None Hypusine is formed in eIF-5A by post-translational modification of one of the lysyl residues. There are two reactions and two enzymes involved:; Hypusine is an unusual amino acid found in all eukaryotes and in some archaea, but not in bacteria. The only known protein containing hypusine is eukaryotic translation initiation factor 5A (eIF-5A) and a similar protein found in archaebacteria. In human, two isoforms of eIF-5A have been described: eIF-5A-1 and eIF-5A-2. They are coded by two different genes. This protein is involved in protein biosynthesis and promotes the formation of the first peptide bond. The region surrounding the hypusine residue is highly conserved among the eukaryotes and is essential to the function of eIF-5A. Thus, hypusine and eIF-5A appear to be vital for the viability and proliferation of eukaryotic cells. C10H23N3O3 None None None 1291.46 1029.07 1003.4 985.189 1020.84 1518.28 1023.71 1070.4 1152.21 917.259 1163.84 1200.2 456.732 1041.38 2103.17 950.249 1152.94 1203.82 973.277 1276.82 1121.22 1069.49 1162.81 1354.7 1298.86 1127.43 1224.57 1599.73 1020.49 1435.3 1257.12 1100.45 1149.84 1471.65 1266.55 988.053 1104.86 1194.44 818.734 1192.01 840.563 1088.55 234.0801193_MZ Kinetin Un 1.0 None None None None Kinetin can react with UDP-D-glucose to produce kinetin-7-N-glucoside or kinetin-9-N-glucoside, with UDP as a byproduct. The reaction is catalyzed by UDP glycosyltransferase. Kinetin is a hormone derived from plants. C10H9N5O None None None 4488.64 5054.53 6059.09 6395.03 4385.8 5218.42 4607.39 4127.54 4277.25 4481.02 4960.76 5000.81 3662.99 4687.66 4924.95 4922.23 5447.96 3373.69 4203.83 3550.31 4853.26 4094.97 5418.21 5065.26 3991.04 4127.66 4747.51 4631.21 3965.6 5358.77 4388.13 4232.99 3107.29 3884.47 4519.02 4336.39 3954.73 4205.24 2881.6 4666.43 3245.5 3775.35 235.1698149_MZ Capsidiol Un 1.0 None None None None Capsidiol is a phytoalexin, a natural fungicide present in pepper. (PMID: 10335386). Capsidiol shows bacteriostatic properties in vitro against Helicobacter pylori with a minimum inhibitory concentration (MIC) of 200 microg/mL. (PMID: 17002415). Capsidiol is a bicyclic, dihydroxylated sesquiterpene produced by several solanaceous species in response to a variety of environmental stimuli. It is the primary antimicrobial compound produced by Nicotiana tabacum in response to fungal elicitation, and it is formed via the isoprenoid pathway from 5-epi-aristolochene. (PMID: 11556809). C15H24O2 None None None 7107.02 7023.83 7564.32 7030.11 7591.31 8043.59 7763.57 7359.09 7141.94 7981.39 8386.79 7281.92 6054.72 8157.89 7796.1 6196.66 7835.48 5950.67 6868.71 7326.88 7093.8 6885.02 8045.88 6720.15 6919.3 6646.91 7316.11 7272.58 7125.32 7581.63 6578.67 5376.9 7265.17 7067.06 6891.37 6623.68 6635.57 6991.32 7500.44 7008.25 6536.77 6454.46 236.0774460_MZ Biopterin Un 1.0 None None None None Biopterin concentrations in cerebrospinal fluid from patients with Parkinson's disease, in which the nigrostriatal dopamine neurons degenerate, are lower than those from age-matched older controls. In hereditary progressive dystonia/DOPA-responsive dystonia, which is a dopamine deficiency caused by mutations in GTP cyclohydrolase I without neuronal cell death (Segawa's disease), neopterin and biopterin in cerebrospinal fluid decrease in parallel owing to the decreased activity in GTP cyclohydrolase I. GTP cyclohydrolase I (EC 3.5.4.16) is an enzyme that is part of the folate and biopterin biosynthesis pathways. It is responsible for the hydrolysis of guanosine triphosphate (GTP) to form 7,8-dihydroneopterin 3'-triphosphate. (Pteridines (1999), 10(1), 5-13.) Lowered levels of urinary biopterin concomitant with elevated serum phenylalanine concentration occur in a variant type of hyperphenylalaninemia caused by a deficiency of tetrahydrobiopterin (BH4), the obligatory cofactor for phenylalanine hydroxylase. The most frequent form of this cofactor deficiency is due to lack of 6-pyruvoyl-tetrahydropterin synthase (PTPS) activity, the second enzyme in the biosynthetic pathway for BH4. (PMID 8178819) The hepatic phenylalanine hydroxylating system consists of 3 essential components, phenylalanine hydroxylase, dihydropteridine reductase, and the nonprotein coenzyme, tetrahydrobiopterin. The reductase and the pterin coenzyme are also essential components of the tyrosine and tryptophan hydroxylating systems. There are 3 distinct forms of phenylketonuria or hyperphenylalaninemia, each caused by lack of 1 of these essential components. The variant forms of the disease that are caused by the lack of dihydropteridine reductase or tetrahydrobiopterin are characterized by severe neurol. deterioration, impaired functioning of tyrosine and tryptophan hydroxylases, and the resultant deficiency of tyrosine- and tryptophan-derived monoamine neurotransmitters in brain. (PMID 3930837). C9H11N5O3, Sepiapterin, D-Biopterin, Orinapterin, Dyspropterin, Primapterin, 8-[(aminomethyl)sulfanyl]-6-sulfanyloctanoic acid None None None 10534.6 8843.85 8485.46 8723.89 7968.48 10629.1 9464.14 7759.09 16892.6 8871.13 9569.76 8855.29 7330.23 11696.1 8550.15 8873.42 8922.5 5765.33 7199.05 6455.99 9380.78 8389.0 9960.21 8786.12 7301.43 7941.41 7790.59 8953.18 9127.71 9583.97 11786.5 10771.8 10998.5 8979.16 9495.17 9259.99 7307.54 8064.94 5043.58 8396.23 6725.07 7297.58 236.9869282_MZ 5-Sulfosalicylic acid Un 1.0 None None None None 5-Sulfosalicylic acid is a derivative of salicylic acid, a common anti-inflammatory drug. Sulfosalicylic acid is used in urine tests to determine urine protein content. The chemical causes the precipitation of dissolved proteins, which is measured from the degree of turbidity. It is also used for integral colour anodizing. -Wikipedia. C7H6O6S None None None 16770.2 17098.1 20183.2 15161.1 18617.0 13518.7 17433.0 19826.1 17444.0 15607.9 15941.0 16078.7 20378.7 14092.4 18421.7 12934.5 19617.1 27372.9 25026.1 19256.0 19516.3 18740.4 16114.0 22623.8 22473.0 19804.3 19519.6 16453.9 19619.8 13522.7 15516.8 14884.6 28847.1 22375.2 14718.2 18187.0 23981.1 17509.6 23556.7 19623.1 16689.9 22460.6 238.0945466_MZ Dihydrobiopterin Un 1.0 None None None None Dihydrobiopterin (BH2) is an oxidation product of tetrahydrobiopterin. Tetrahydrobiopterin is a natural occurring cofactor of the aromatic amino acid hydroxylase and is involved in the synthesis of tyrosine and the neurotransmitters dopamine and serotonin. Tetrahydrobiopterin is also essential for nitric oxide synthase catalyzed oxidation of L-arginine to L-citrulline and nitric oxide. C9H13N5O3, 6-Lactoyltetrahydropterin, 4a-Carbinolamine tetrahydrobiopterin, 1-hydroxy-2-Oxopropyl tetrahydropterin None None None 8429.07 5918.51 5276.51 6286.78 5334.44 8950.47 6324.68 5797.81 4143.23 5368.94 6873.45 4746.97 6042.35 6234.24 6198.46 7378.08 5284.93 5706.52 5363.31 13569.4 6625.05 3709.94 7937.08 5564.93 5500.86 7126.03 6123.42 5682.87 3884.2 6282.14 13302.9 5968.67 3302.68 7329.11 5364.19 6511.25 4081.41 3351.3 3304.39 5470.66 13531.3 5798.97 239.1150588_MZ Anserine Un 1.0 None None None None This dipeptide is normally absent from human tissues and body fluids, and its appearance there is an artifact of diet (Proc Soc Pediatr Res 134, 1967.) and serum carnosinase deficiency. (OMIM 212200) Anserine is present in the skeletal muscle of birds and certain species of mammals, notably the rabbit, rat, and whale, contains anserine. (Proc Soc Pediatr Res 134, 1967) The methyl group of anserine is added to carnosine by the enzyme S-adenosylmethionine: carnosine N-methyltransferase. (J Biol Chem 237:1207, 1962.). C10H16N4O3, Homocarnosine, Balenine None None None 10291.1 7720.25 23476.3 10422.8 6761.78 9248.54 9021.75 8416.36 7147.8 6648.48 9213.32 10157.0 6948.01 8468.13 8670.35 12864.8 8577.43 4375.17 6279.8 7837.95 12417.4 12523.3 7740.33 7213.08 6681.9 16297.3 8122.5 14533.8 17324.7 28963.6 9504.37 7846.07 6412.35 8312.07 39860.5 6885.4 6688.9 7245.29 6960.9 7284.06 6890.82 7082.58 241.0125901_MZ Inositol cyclic phosphate Un 1.0 None None None None Inositol cyclic phosphate is a substrate for Annexin A3. C6H11O8P None None None 40509.3 43912.3 39862.4 43379.5 35788.1 43741.1 40929.6 45607.7 41653.0 44830.7 53744.6 46341.8 37729.4 36836.2 42213.8 58795.5 33421.1 43722.4 40053.8 38842.0 47652.4 41026.7 32982.3 38763.0 45194.6 37370.3 44719.5 37296.8 37253.5 36833.2 49594.6 54749.0 45467.7 37485.0 53070.8 48984.3 40039.7 45826.7 26333.1 42959.2 42838.4 43467.7 241.1805457_MZ 3-Oxotetradecanoic acid Un 1.0 None None None None 3-Oxo-tetradecanoic acid is an intermediate in fatty acid biosynthesis. Specifically, 3-Oxo-tetradecanoic acid is converted from Malonic acid via three enzymes; 3-oxoacyl-[acyl-carrier-protein] synthase, fatty-acid Synthase and beta-ketoacyl -acyl-carrier-protein synthase II. (EC:2.3.1.41, E.C: 2.3.1.85, 2.3.1.179). In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. C14H26O3 None None None 12478.1 11954.1 16304.1 14211.1 13479.9 11614.3 15853.4 23657.0 10544.3 12063.3 11047.6 11367.3 11858.0 12451.2 15308.0 10885.7 31186.8 10340.6 10736.4 15474.0 11419.5 10412.5 12533.4 13150.0 12097.6 9662.46 12240.8 12457.6 9977.75 13665.4 9926.73 8672.73 8784.92 11299.2 10958.4 12501.9 9497.33 11742.3 11564.8 12922.7 9165.94 11766.8 241.2169386_MZ Pentadecanoic acid Un 1.0 None None None None Pentadecanoic acid is a fatty acid of exogenous (primarily ruminant) origin. Many odd length long chain amino acids are derived from the consumption of dairy fats (milk and meat). Pentadecanoic acid constitutes 1.05% of milk fat and 0.43% of ruminant meat fat. The content of heptadecanoic acid in the subcutaneous adipose tissue of humans appears to be a good biological marker of long-term milk fat intake in free-living individuals in populations with high consumption of dairy products. (PMID 9701185; PMID 11238766). C15H30O2 None None None 138474.0 136860.0 116204.0 114554.0 117825.0 132284.0 136760.0 153073.0 115427.0 127092.0 128785.0 119043.0 122818.0 144764.0 119755.0 104281.0 149701.0 182498.0 113331.0 145734.0 126584.0 106820.0 123754.0 150510.0 114627.0 103382.0 109653.0 141176.0 103939.0 146119.0 107380.0 99962.2 116256.0 126097.0 103884.0 131680.0 99303.5 117123.0 121548.0 126831.0 101172.0 118518.0 242.1398431_MZ Tiglylcarnitine Un 1.0 None None None None Tiglylcarnitine is detected in the urinary organic acid and blood spot acylcarnitine profiles in patients with mitochondrial acetoacetyl-CoA thiolase (T2) deficiency -- an inborn error of metabolism affecting isoleucine and ketone bodies in the catabolic process. (PubMed ID 14518824 ). C12H21NO4 None None None 6905.08 8257.88 6214.75 11328.1 5582.36 7740.3 8382.98 11529.7 6298.32 7474.82 10801.0 7035.42 4015.56 8160.86 6051.46 8363.01 8052.9 4228.19 5720.06 6663.15 8357.05 6550.7 8865.7 6997.82 5870.33 5273.76 6870.42 5372.36 6520.83 10610.2 10246.3 8093.68 5532.58 6239.75 6410.7 7546.91 5176.6 5589.37 2873.79 7444.59 3882.7 5992.37 242.1758300_MZ N-Undecanoylglycine Un 1.0 None None None None N-Undecanoylglycine is an acylglycine with C-11 fatty acid group as the acyl moiety. Acylglycines 1 possess a common amidoacetic acid moiety and are normally minor metabolites of fatty acids. Elevated levels of certain acylglycines appear in the urine and blood of patients with various fatty acid oxidation disorders. They are normally produced through the action of glycine N-acyltransferase which is an enzyme that catalyzes the chemical reaction: acyl-CoA + glycine ↔ CoA + N-acylglycine. C13H25NO3 None None None 39200.7 20715.6 29826.0 13408.6 11555.1 31358.9 38228.0 37129.3 16199.1 22672.8 34943.4 8297.96 36487.0 28690.1 17703.2 11357.3 42694.8 22036.1 14326.3 25692.1 19828.4 13414.3 63254.4 42772.0 16294.3 20422.2 12317.4 32098.7 14607.3 32401.3 29261.0 21393.9 8178.31 30546.4 25534.3 18025.6 17492.4 11063.6 14323.0 17670.1 35152.3 18121.7 243.0275958_MZ Fucose 1-phosphate Un 1.0 None None None None Fucose-1-phosphate is an intermediate in the reversible synthesis of GDP-L-fucose, in a reaction catalyzed by the enzyme guanosine triphosphate fucose pyrophosphorylase (GFPP, E.C. 2.7.7.30). The reversible reaction is magnesium-dependent, although the enzyme is partially active when cobalt or manganese is substituted. The reaction is unusual in that, of the four canonical nucleoside triphosphates, only guanosine can be utilized efficiently to form a nucleotide-sugar. Free cytosolic fucose is phosphorylated by L-fucokinase (EC 2.7.1.52) to form fucose-1-phosphate in the salvage pathway of GDP-L-fucose. (PMID: 16185085, 14686921). C6H13O8P None None None 23349.7 20483.9 21356.3 13562.0 19463.7 27158.4 18870.6 17417.5 21158.5 23325.9 21283.0 22553.1 27130.7 22249.2 22546.6 25876.6 18493.0 32737.9 22822.8 22729.0 25518.7 22468.0 21423.0 23879.9 22744.8 19017.8 20915.2 24786.5 23762.2 25707.3 18767.1 21678.4 23914.1 18746.8 20057.0 26925.1 21353.9 20750.9 11549.1 24512.5 19371.6 21300.7 243.0620509_MZ Uridine Un 1.0 None None None None Uridine is a molecule (known as a nucleoside) that is formed when uracil is attached to a ribose ring (also known as a ribofuranose) via a b-N1-glycosidic bond. (Wikipedia). C9H12N2O6, Pseudouridine None None None 160976.0 172497.0 217489.0 224158.0 173922.0 315654.0 214866.0 143473.0 231888.0 338174.0 136934.0 263549.0 314006.0 174631.0 233698.0 378330.0 151156.0 577263.0 281348.0 238329.0 140403.0 203354.0 220033.0 165215.0 205296.0 231813.0 188337.0 327985.0 277245.0 269186.0 122474.0 286093.0 243721.0 185749.0 261183.0 280846.0 214664.0 175540.0 257297.0 261899.0 254815.0 234043.0 243.1597131_MZ 1,11-Undecanedicarboxylic acid Un 1.0 None None None None Undecanedicarboxylic acid is an unusual odd-numbered dicarboxylic acid that appears in the urines of children with neonatal adrenoleukodystrophy and Zellweger syndrome, as an additional marker of these peroxisomal disorders. (PMID: 2943344). C13H24O4 None None None 16434.1 15224.9 20056.7 15178.0 15787.8 15770.0 17796.9 30395.7 9735.08 13789.7 15174.2 7528.1 11705.4 14772.2 20798.5 17348.0 43535.3 8168.94 13261.4 17316.9 13929.1 6642.96 14554.6 16844.7 14568.5 7710.14 17464.6 10989.2 6575.05 18622.4 11916.1 12264.9 6259.57 9641.49 7256.28 16426.0 9109.05 6493.56 11749.2 15666.7 8506.28 14408.8 243.1962963_MZ (R)-3-Hydroxy-tetradecanoic acid Un 1.0 None None None None (R)-3-Hydroxy-tetradecanoic acid is an intermediate in fatty acid biosynthesis. Specifically, (R)-3-Hydroxy-tetradecanoic acid is converted from 3-Oxo-tetradecanoic acid via fatty-acid Synthase and 3-oxoacyl- [acyl-carrier-protein] reductase. (EC: 2.3.1.85 and EC:2.3.1.41). C14H28O3, 2-Hydroxymyristic acid None None None 8444.29 7449.49 7986.13 7992.16 7104.19 7578.96 9020.43 10703.1 6544.39 7553.29 7494.0 6755.01 6617.52 9980.77 7420.47 5871.6 12085.4 6986.85 6738.19 7887.53 6982.95 5928.16 8873.82 8099.64 7188.89 6314.32 6503.99 7897.91 5911.43 9064.2 5807.13 5222.3 5279.43 6702.17 6504.29 8023.37 5551.41 6830.65 6220.77 7294.11 6342.69 7327.98 243.2228163_MZ N1-Acetylspermine Un 1.0 None None None None C12H28N4O None None None 2018.8 2031.83 1985.71 1664.95 1714.02 1835.24 2353.34 2564.26 1740.24 1832.92 1913.52 1593.91 1977.2 2323.5 1746.42 1483.41 2660.12 3163.75 1784.61 2330.77 1860.92 1495.96 1871.51 2177.53 1602.22 1737.18 1574.34 2494.04 1471.33 2136.45 1671.05 1361.03 1501.39 1938.19 1469.2 1988.26 1425.18 1670.14 1737.1 1915.83 1803.55 1875.78 245.1143129_MZ L-beta-aspartyl-L-leucine Un 1.0 None None None None L-beta-aspartyl-l-leucine is a proteolytic breakdown product of larger proteins. It belongs to the family of N-acyl-alpha Amino Acids and Derivatives. These are compounds containing an alpha amino acid which bears an acyl group at his terminal nitrogen atom. It is found in urine (PMID: 3782411). C10H18N2O5, L-gamma-glutamyl-L-valine None None None 29379.2 31679.5 32828.2 30117.2 44274.1 36127.4 28561.9 53612.1 24412.1 27530.5 34684.9 33420.9 18732.0 30113.2 33022.4 32614.6 28230.7 20245.7 20999.9 24717.2 27633.2 31225.5 26992.7 30996.4 30247.8 43360.4 28807.9 27385.0 38210.5 28267.4 25848.6 27866.3 27604.4 23050.1 36473.7 29792.3 26571.0 29188.8 16802.9 33771.5 20160.4 27580.7 245.1366589_MZ 3-Hydroxydodecanedioic acid Un 1.0 None None None None 3-Hydroxydecanedioic acid appears in the urine of children affected with peroxisomal disorders. Peroxisomal biogenesis disorders (PBDs) are characterized by generalized peroxisomal dysfunction due to defective assembly of the organelle and include the Zellweger, neonatal adrenoleukodystrophy and infantile Refsum phenotypes (PMID 10896310). C12H22O5 None None None 18309.9 17372.0 12088.1 18693.8 24102.0 21687.8 12766.7 27262.4 10645.8 17731.5 20397.4 8371.29 7775.84 20195.9 21993.4 17951.4 18557.7 9822.12 15708.5 16236.2 17039.1 8311.15 17225.0 19787.8 15211.7 10796.3 16829.3 9511.3 8777.97 19867.1 15685.2 14405.6 7334.8 10387.4 10570.2 17450.8 9722.22 7651.09 10203.7 17193.2 11065.8 18175.7 246.0979813_MZ Malonylcarnitine Un 1.0 None None None None Malonylcarnitine is a metabolite that accumulates with specific disruption of fatty-acid oxidation caused by impaired entry of long-chain acylcarnitine esters into the mitochondria and failure of the mitochondrial respiratory chain at complex 11 and malonyl-CoA decarboxylase (EC 4.1.1.9) deficiency (OMIM 248360). Malonylcarnitine has also been found to accumulate in some newborns with medium-chain acyl-CoA dehydrogenase (EC 1.3.99.3) deficiency (OMIM 201450). (PMID 11558490, 15303003, 12651823). C10H17NO6 None None None 5957.89 10032.0 12494.4 54313.4 21520.9 14035.9 24036.5 24093.9 21738.7 15600.9 23168.3 16029.9 4294.52 10267.3 20628.2 9319.82 26689.7 3381.88 11623.9 5519.64 9279.0 8681.19 30065.8 16383.3 9810.98 9867.47 22304.6 12801.3 7796.42 8929.83 13928.3 11035.0 6312.87 14027.0 11170.0 14431.9 9809.93 18258.1 4014.42 24658.8 3950.85 13010.5 247.1335890_MZ Gamma-CEHC Un 1.0 None None None None Gamma-CEHC is metabolites of Vitamin E. smokers has significantly higher excretion of urinary gamma-CEHC that's why they require more vitamin E compared to non-smokers.Cigarette smoking is associated with increased oxidative stress and increased risk of degenerative disease. As the major lipophilic antioxidant, requirements for vitamin E may be higher in smokers due to increased utilisation.(PMID:15493460). C15H20O3 None None None 12137.7 18847.9 19965.4 19908.6 30544.3 21780.6 15240.8 13680.8 19419.1 19089.5 28130.9 25751.1 5523.81 22347.6 22750.7 15605.6 11618.8 5442.28 11820.6 10967.6 14709.4 19185.8 18391.7 14710.3 16338.7 19718.8 20665.1 15730.1 18171.6 20777.2 10912.8 11881.7 24852.5 12149.1 18779.8 13220.7 15459.0 24121.7 7142.6 18986.2 6993.96 10009.1 249.0548396_MZ Gamma-Glutamylcysteine Un 1.0 None None None None G-Glutamylcysteine is a product of enzyme glutamate-cysteine ligase [EC 6.3.2.2] and a substrate of enzyme glutathione synthase [EC 6.3.2.3] in glutamate metabolism pathway (KEGG). C8H14N2O5S None None None 14574.4 12437.0 14925.3 12484.2 18533.0 15044.8 16428.0 13268.3 10382.3 12020.8 11197.5 8897.16 28739.5 10469.2 14262.8 19461.5 14207.2 26021.4 15150.0 17273.8 15267.9 7956.86 13847.5 12636.4 20394.7 10738.6 19874.6 14686.5 11543.3 10413.2 18191.7 18271.9 9485.96 11301.0 9609.5 12723.1 12226.9 8648.56 11415.1 14113.9 27005.2 15673.2 249.1134579_MZ Ubiquinone Q1 Un 1.0 None None None None Ubiquinone-1 is a member of the chemical class known as Polyprenylbenzoquinones. These are compounds containing a polyisoprene chain attached to a quinone at the second ring position. Ubiquione-1 has just 1 isoprene unit. Normally in humans it has 10. Ubiquinone-1 is an intermediate in the synthesis of Ubiquionone 10, which is also called Coenzyme Q (CoQ). CoQ is found in the membranes of endoplasmic reticulum, peroxisomes, lysosomes, vesicles and notably the inner membrane of the mitochondrion where it is an important part of the electron transport chain; there it passes reducing equivalents to acceptors such as Coenzyme Q : cytochrome c - oxidoreductase. CoQ is also essential in the formation of the apoptosome along with other adapter proteins. The loss of trophic factors activates pro-apoptotic enzymes, causing the breakdown of mitochondria. Because of its ability to transfer electrons and therefore act as an antioxidant, Coenzyme Q has become a valued dietary supplement. CoQ10 has been widely used for the treatment of heart disease (especially heart failure), gum diseases, and also breast cancer. The benzoquinone portion of Coenzyme Q10 is synthesized from amino acids, while the isoprene sidechain is synthesized from acetyl CoA through the mevalonate pathway. The mevalonate pathway is used for the first steps of cholesterol biosynthesis. C14H18O4 None None None 8613.75 10798.3 11880.4 11529.0 14206.3 13277.4 11482.9 12667.4 9174.15 10458.8 14527.6 11086.5 6197.43 12465.6 13366.3 10716.6 20368.8 5815.47 7607.26 8901.48 9661.3 8517.02 11713.7 10176.0 9433.88 8331.09 11091.8 8880.71 8134.42 12400.4 8508.13 8886.62 8993.95 7185.36 9010.92 8832.1 7318.41 9279.61 5666.55 10924.0 6272.4 8054.79 250.0945053_MZ Deoxyadenosine Un 1.0 None None None None Deoxyadenosine is a derivative of nucleoside adenosine. It is comprised of adenine attached to a deoxyribose moiety via a N9-glycosidic bond. Deoxyribose differs from ribose by the absence of oxygen in the 3' position of its ribose ring. Deoxyadenosine is a critical component of DNA. C10H13N5O3, 5'-Deoxyadenosine None None None 7781.99 8146.78 8337.7 5449.26 6954.0 10994.7 7507.77 7011.81 7212.15 5234.22 8102.13 8021.31 6211.05 7041.82 7547.84 6815.3 6397.44 5746.77 5674.24 5863.15 7508.24 8234.19 8207.05 9127.3 5480.97 7323.25 6423.17 11308.8 7990.03 7412.48 6167.22 6106.5 6015.02 6368.69 11888.2 8579.91 5756.73 7045.27 4929.86 7506.68 5604.56 6880.06 250.1100887_MZ Isovalerylglutamic acid Un 1.0 None None None None Isovalerylglutamic acid is an unusual mtabolite that has been found in the urine of patients with Isovaleric Acidemia due to Isovaleryl-CoA Dehydrogenase Deficiency (OMMBID: The Metabolic and Molecular Bases of Inherited Disease, Ch.93: Branched Chain Organic Acidurias). and in Multiple acyl-Co A dehydrogenation deficiency (MADD) (PMID 6862997). C10H17NO5, Suberylglycine None None None 3842.58 3875.41 4151.95 5559.06 3971.34 4576.54 4135.61 3695.05 3721.81 3324.07 3967.2 3956.93 3174.37 4021.48 3894.28 3511.66 4342.05 3290.86 3089.72 3072.08 4007.45 3233.7 4144.74 4035.36 3462.71 3498.13 3498.17 4054.92 2998.93 4110.39 3420.38 3251.89 2955.43 3350.52 4270.43 3795.41 3356.64 3299.32 2376.53 3803.46 3135.09 3488.56 250.1449057_MZ Isobutyryl-L-carnitine Un 1.0 None None None None Isobutyryl-L-carnitine is a product of the acyl-CoA dehydrogenases (ACADs), which are a group of mitochondrial enzymes involved in the metabolism of fatty acids or branched-chain amino acids. (OMIM 600301 ). C11H21NO4, Butyrylcarnitine None None None 8097.98 8510.49 7747.8 8682.75 6447.61 8979.73 7643.48 7487.1 7207.25 7048.16 10259.6 7691.41 5091.93 8760.02 6269.26 6844.82 9172.73 7905.42 5706.58 7316.09 7902.81 7426.32 8870.68 9717.43 6451.66 7214.9 6519.41 9132.01 6981.09 11573.7 6981.91 6066.35 7446.32 6890.48 8429.82 9346.92 7265.19 8860.56 4871.95 8331.63 6459.29 7247.22 251.2013910_MZ 7_10-Hexadecadienoic acid Un 1.0 None None None None C16H28O2, 7Z_10Z-Hexadecadienoic acid None None None 8610.2 7438.46 7452.5 19440.7 9371.83 12433.8 13573.6 9844.31 9168.03 9823.1 8556.19 7216.7 8845.32 10175.1 13501.0 5736.57 10324.7 14106.9 11139.7 10365.0 8311.64 6060.43 9142.76 9568.28 8854.46 6886.83 9400.2 10986.2 6442.5 9572.97 8393.78 6181.54 7269.38 8044.24 6862.23 13395.8 7065.64 7662.02 7759.91 9068.09 13026.5 14078.6 252.0859938_MZ N-Acetylvanilalanine Un 1.0 None None None None N-acetylvanilalanine is a catecholamine metabolite. Its accumulation is indicative of aromatic L-amino acid decarboxylase deficiency (PMID: 16288991). C12H15NO5 None None None 5317.31 5073.24 5048.49 5802.97 4682.4 7159.9 5932.34 4740.9 4711.5 4971.71 4267.0 5851.49 3656.46 5290.64 4973.14 7069.54 5435.97 4697.74 5062.19 5673.64 4602.36 4701.74 5500.19 4866.47 4697.38 4328.77 4616.54 5107.35 4181.47 6511.44 5467.15 5715.89 4217.83 4571.91 4491.4 4788.57 4639.89 4630.3 2984.32 4654.69 4810.05 4535.7 253.0509421_MZ 5-L-Glutamyl-taurine Un 1.0 None None None None 5-L-Glutamyl-taurine is an intermediate in Taurine and hypotaurine metabolism. 5-L-Glutamyl-taurine is produced from Taurine via the enzyme gamma-glutamyltranspeptidase (EC 2.3.2.2). C7H14N2O6S, Daidzein None None None 24470.4 18603.5 22974.1 18812.3 17591.6 20341.3 17494.9 19188.8 15637.7 18760.4 18576.8 19823.0 13928.1 19101.4 18220.8 16796.5 18618.9 16723.3 15709.9 15780.2 18690.7 17792.5 17155.2 17102.5 18954.8 21389.2 19128.4 16959.7 18836.6 24460.9 17778.1 14855.8 15477.6 16668.9 17092.7 17108.4 17547.7 15527.3 13317.1 18033.4 17575.4 16045.0 253.1274942_MZ Homoanserine Un 1.0 None None None None Homoanserine (N-(4-Aminobutyryl)-L-histidine) is a dipeptide identified in the brain and muscles of mammals. (PMID 3780724, 6078589) It has been found that homoanserine is not merely deposited in skeletal muscles but that is actively synthesized by muscle cells in culture. (PMID 8307008). C11H18N4O3 None None None 4628.97 4367.7 5431.69 4513.69 4446.88 4830.32 4280.8 5291.6 4111.26 4122.0 4094.62 4146.9 3009.81 4862.89 5150.66 4896.19 6550.75 2574.74 3586.02 4133.96 3886.69 4643.23 3933.5 3635.59 4201.93 4745.65 4701.8 5801.48 4988.24 4557.54 3909.53 3933.58 3322.76 3684.05 7139.6 4593.07 3465.83 3363.0 3236.74 4597.08 3075.15 3475.22 253.2172565_MZ Palmitoleic acid Un 1.0 None None None None fatty acids, Monounsaturated. Palmitoleic acid, or 9-hexadecenoic acid, is an unsaturated fatty acid that is a common constituent of the glycerides of human adipose tissue. Present in all tissues, generally found in higher concentrations in the liver. Macadamia oil (Macadamia integrifolia) and Sea Buckthorn oil (Hippophae rhamnoides) are botanical sources of palmitoleic acid, containing 22 and 40% respectively. -- Wikipedia. C16H30O2, Hypogeic acid, Trans-Hexa-dec-2-enoic acid, Palmitelaidic acid None None None 214194.0 105940.0 143823.0 173812.0 221206.0 383439.0 320844.0 220614.0 187296.0 184448.0 180355.0 121435.0 463014.0 309522.0 349531.0 115376.0 115933.0 756360.0 223652.0 264242.0 168793.0 122463.0 134784.0 284176.0 215985.0 169342.0 153505.0 236360.0 141344.0 165585.0 165689.0 109496.0 213270.0 145914.0 102983.0 452225.0 166425.0 129738.0 163206.0 167784.0 699235.0 488766.0 255.1096877_MZ 2-(3-Carboxy-3-aminopropyl)-L-histidine Un 1.0 None None None None 2-(3-Carboxy-3-aminopropyl)-L-histidine is an unusual amino acid that results from the post-translational modification of histidine in certain proteins. In particular, it is a post-translational derivative of histidine that exists in protein synthesis elongation factor 2 (EF2) at the site of diphtheria toxin-catalyzed ADP-ribosylation of elongation factor 2. It is a precursor for diphthamide. This compound is a substrate for the enzyme diphthine synthase (EC 2.1.1.98). This enzyme catalyzes the chemical reaction: S-adenosyl-L-methionine + 2-(3-carboxy-3-aminopropyl)-L-histidine = S-adenosyl-L-homocysteine + 2-[3-carboxy-3-(methylammonio)propyl]-L-histidine. C10H16N4O4 None None None 4600.68 5059.53 6085.56 6000.67 6248.36 6125.6 6204.16 6993.96 5760.67 5168.6 4858.01 5697.15 4180.83 5355.49 6870.11 6919.35 7020.67 3012.32 4654.06 5280.81 4596.55 4926.31 5096.56 4198.48 6354.71 6067.34 6573.7 6302.23 5161.01 5032.33 5844.23 5884.83 4794.52 4572.08 7365.54 5223.86 4799.95 5407.97 3822.12 5256.32 4857.33 4396.45 255.2331709_MZ Palmitic acid Un 1.0 None None None None Palmitic acid, or hexadecanoic acid is one of the most common saturated fatty acids found in animals and plants, a saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids.(wikipedia) Biological Source: Occurs in the form of esters (glycerides) in oils and fats of vegetable and animal origin. Usually obtained from palm oil. Widely distributed in plants Use/Importance:. Palmitic acid is used in determination of water hardness Biological Use/Importance: Active ingredient of *Levovist*TM, used in echo enhancement in sonographic Doppler B-mode imaging. Ultrasound contrast medium (Dictionary of Organic Compounds). C16H32O2, Trimethyltridecanoic acid None None None 8352060.0 8212690.0 6822230.0 7186410.0 7294970.0 8017060.0 9546060.0 9334480.0 7740920.0 7576190.0 8417650.0 8388740.0 8843820.0 8693140.0 6719960.0 6191140.0 8517090.0 13491000.0 6849520.0 9827910.0 7169650.0 6076700.0 7882080.0 8495480.0 7099020.0 6565320.0 6264310.0 9944260.0 6191910.0 8268340.0 6653370.0 5755280.0 7854160.0 7138510.0 5760670.0 8057920.0 6426700.0 7532030.0 7502060.0 7266160.0 7943740.0 7908080.0 256.0946105_MZ Glycerophosphocholine Un 1.0 None None None None Glycerophosphorylcholine (GPC) is a choline derivative and one of the two major forms of choline storage (along with phosphocholine) in the cytosol. Glycerophosphorylcholine is also one of the four major organic osmolytes in renal medullary cells, changing their intracellular osmolyte concentration in parallel with extracellular tonicity during cellular osmoadaptation. As an osmolyte, Glycerophosphorylcholine counteracts the effects of urea on enzymes and other macromolecules. Kidneys (especially medullar cells), which are exposed under normal physiological conditions to widely fluctuating extracellular solute concentrations, respond to hypertonic stress by accumulating the organic osmolytes glycerophosphorylcholine (GPC), betaine, myo-inositol, sorbitol and free amino acids. Increased intracellular contents of these osmolytes are achieved by a combination of increased uptake (myo-inositol and betaine) and synthesis (sorbitol, GPC), decreased degradation (GPC) and reduced osmolyte release. GPC is formed in the breakdown of phosphatidylcholine (PtC). This pathway is active in many body tissues, including mammary tissue. C10H15N3O5, 5-Methylcytidine None None None 26697.8 33280.0 25249.3 21310.0 32246.0 35676.8 29004.0 51237.0 34287.4 33636.0 34377.1 37610.3 22108.9 33927.4 37725.2 38828.3 25453.5 25816.6 32295.5 40695.1 34773.9 42517.8 29326.1 30652.1 25239.1 32270.8 25949.0 23564.9 34195.5 28541.9 34337.3 26445.4 41514.9 21558.7 32054.0 32734.8 22223.3 33209.0 18467.4 40590.9 22809.5 25787.6 256.1561330_MZ 2-Hexenoylcarnitine Un 1.0 None None None None C13H23NO4 None None None 3620.44 3614.77 3753.71 4085.49 2381.52 3788.76 4166.03 4526.54 2837.84 3158.32 4266.71 2841.97 2729.59 3962.73 2722.17 3245.03 5105.83 2338.33 2586.87 3117.01 3299.72 2282.24 4489.89 3898.98 2783.03 2052.67 3222.96 2919.11 2639.89 4594.78 4840.48 3560.08 1766.2 3616.36 3107.99 3112.92 2924.62 2308.68 1986.29 2859.89 2639.74 2863.06 257.1754043_MZ Tetradecanedioic acid Un 1.0 None None None None Tetradecanedioic acid is a C14 dicarboxylic acid. C14H26O4 None None None 10283.0 9792.39 12024.7 16049.5 8805.12 9620.46 11479.8 16777.2 6013.07 8483.07 11023.3 5375.21 4720.61 9024.63 11035.2 9797.01 25585.7 6294.54 6986.53 9927.74 8594.58 3851.16 8575.88 10121.1 8823.53 5414.9 9815.32 7957.13 5590.8 11166.4 7920.43 7006.4 4282.53 7173.75 8135.76 10284.2 5612.82 4127.9 7576.75 8547.67 5570.49 9184.17 258.0388297_MZ Glucosamine 6-phosphate Un 1.0 None None None None Glucosamine 6-phosphate is normally produced in endothelial cells via the de novo glucosamine synthesis by the enzyme fructose-6-phosphate amidotransferase and the modulation of this pathway by hyperglycemia and glutamine. glutamine-fructose-6-phosphate amidotransferase (GFAT) catalyzes the first committed step in the pathway for biosynthesis of hexosamines in mammals. A member of the N-terminal nucleophile class of amidotransferases, GFAT transfers the amino group from the L-glutamine amide to D-fructose 6-phosphate, producing glutamic acid and glucosamine 6-phosphate. As glucosamine inhibits endothelial nitric oxide synthesis it has important implications for impaired endothelium-dependent relaxation and vascular dysfunction in diabetes mellitus. (PMID 11270676, 11842094). C6H14NO8P, Glucosamine-1P None None None 9425.28 11965.0 11891.6 8293.16 9630.39 12306.4 8250.72 8256.68 8118.44 8967.45 9141.08 12575.6 7463.66 11696.6 10227.9 11716.6 10031.7 9531.05 10025.6 8935.2 11170.3 9129.35 9616.78 10520.3 8798.66 8217.49 12292.4 8427.84 9313.96 9229.08 9007.43 8309.78 7142.76 7915.39 10037.3 9302.06 9257.21 9710.42 6035.88 10227.2 7628.51 8116.36 258.1064468_MZ Bupropion Un 1.0 None None None None Bupropion is a selective catecholamine (norepinephrine and dopamine) reuptake inhibitor. It has only a small effect on serotonin reuptake. It does not inhibit MAO. The antidepressant effect of bupropion is considered to be mediated by its dopaminergic and noradrenergic action. Bupropion has also been shown to act as a competitive alpha-3-beta-4- nicotinic antagonist, the alpha-3-beta-4-antagonism has been shown to interrupt addiction in studies of other drugs such as ibogaine. This alpha-3-beta-4-antagonism correlates quite well with the observed effect of interrupting addiction. A unicyclic, aminoketone antidepressant. The mechanism of its therapeutic actions is not well understood, but it does appear to block dopamine uptake. The hydrochloride is available as an aid to smoking cessation treatment; Bupropion is a selective catecholamine (norepinephrine and dopamine) reuptake inhibitor. It has only a small effect on serotonin reuptake. It does not inhibit MAO. The antidepressant effect of bupropion is considered to be mediated by its dopaminergic and noradrenergic action. Bupropion has also been shown to act as a competitive alpha-3-beta-4-nicotinic antagonist, the alpha-3-beta-4-antagonism has been shown to interrupt addiction in studies of other drugs such as ibogaine. This alpha-3-beta-4-antagonism correlates quite well with the observed effect of interrupting addiction. Bupropion (amfebutamone) (brand names Wellbutrin and Zyban) is an antidepressant of the aminoketone class, chemically unrelated to tricyclics or selective serotonin reuptake inhibitors (SSRIs). It is similar in structure to the stimulant cathinone, and to phenethylamines in general. It is a chemical derivative of diethylpropion, an amphetamine-like substance used as an anorectic. Bupropion is both a dopamine reuptake inhibitor and a norepinephrine reuptake inhibitor. It is often used as a smoking cessation aid. C13H18ClNO None None None 7034.32 7750.18 7991.61 8936.62 8159.52 7293.55 7720.95 9101.37 5976.77 6726.0 7512.66 5955.51 5499.02 7844.03 8799.78 8111.67 12123.0 3424.19 5551.03 6232.2 6763.24 5562.72 6979.66 7509.73 6433.44 5711.37 7277.6 6086.41 5216.56 8607.99 5846.01 6568.74 5258.27 4779.81 5647.63 7467.42 5039.14 5487.65 4166.82 8401.62 3770.6 6192.73 259.0226300_MZ Fructose 6-phosphate Un 1.0 None None None None Fructose 6-phosphate is an important intermediate in the Carbohydrates pathway. The interconversion of glucose-6-phosphate and fructose-6-phosphate, the second step of the Embden-Meyerhof glycolytic pathway, is catalyzed by the enzyme phosphoglucose isomerase (PGI). In gluconeogenesis, fructose-6-phosphate is the immediate precursor of glucose-6-phosphate (wikipedia). C6H13O9P, Myo-inositol 1-phosphate, Galactose 1-phosphate, Dolichyl phosphate D-mannose, Fructose 1-phosphate, Mannose 6-phosphate, D-Myo-inositol 4-phosphate, Glucose 6-phosphate, Glucose 1-phosphate, Inositol phosphate, Beta-D-Glucose 6-phosphate, Beta-D-Fructose 6-phosphate, D-Tagatose 1-phosphate, D-Mannose 1-phosphate, Sorbose 1-phosphate, Beta-D-Fructose 2-phosphate, 1D-myo-Inositol 3-phosphate, D-Tagatose 6-phosphate None None None 891039.0 706481.0 1137470.0 294535.0 872288.0 875094.0 1075100.0 932670.0 1176370.0 777329.0 915046.0 1034450.0 1258810.0 764265.0 1270540.0 730218.0 897330.0 1275940.0 1122200.0 827701.0 953383.0 1066980.0 841427.0 971064.0 1009100.0 983456.0 1042110.0 908971.0 1004830.0 1106040.0 651213.0 729184.0 984952.0 734616.0 1219720.0 1154700.0 1036650.0 1256660.0 856260.0 1105890.0 1108800.0 1015530.0 259.1299543_MZ L-gamma-glutamyl-L-leucine Un 1.0 None None None None L-gamma-glutamyl-l-leucine is a proteolytic breakdown product of larger proteins. It belongs to the family of N-acyl-alpha Amino Acids and Derivatives. These are compounds containing an alpha amino acid which bears an acyl group at his terminal nitrogen atom. It is found in urine (PMID: 3782411). C11H20N2O5, L-gamma-glutamyl-L-isoleucine None None None 28016.3 29625.8 26885.5 25772.1 22712.5 30754.9 24387.1 37823.0 19682.4 20594.3 25531.0 25292.2 18248.7 25484.1 23285.5 28534.6 26945.5 20781.0 20055.6 20823.6 25572.7 23002.5 23121.4 26579.1 24436.8 30176.4 23317.3 23389.2 33355.4 24794.6 25791.0 25925.6 18079.3 21939.6 29565.8 27168.8 23369.8 24256.7 15856.0 28549.1 18287.8 21016.6 259.2430367_MZ Palmitaldehyde Un 1.0 None None None None C16H32O None None None 2075.89 1928.12 1933.71 2113.26 2297.32 2421.25 3195.55 2501.35 2197.09 1606.76 2124.85 2380.79 2756.47 2386.76 1805.71 1673.12 3303.66 4188.64 1727.05 3132.62 1781.55 1494.92 2327.41 1820.87 2259.28 1625.12 1538.61 2732.37 1367.76 2097.26 2754.85 1633.12 1880.95 1691.13 1141.27 2643.93 1753.95 2464.87 1768.32 1951.37 3064.05 2167.2 261.0072591_MZ Homovanillic acid sulfate Un 1.0 None None None None Homovanillic acid sulfate is a component of olive oil and is a major catecholamine metabolite.It is used as a reagent to detect oxidative enzymes, and is associated with dopamine levels in the brain. In psychiatry and neuroscience, brain and cerebrospinal fluid levels of homovanillic acid (HVA) are measured as a marker of metabolic stress caused by 2-deoxy-D-glucose. HVA presence supports a diagnosis of neuroblastoma and malignant pheochromocytoma. (Wikipedia). C9H10O7S None None None 27772.5 22016.8 36364.5 18290.0 25972.5 23327.9 25079.9 22471.5 32760.3 23779.5 23392.6 31653.0 20291.2 22065.8 25596.0 13534.7 22788.8 46320.9 35363.4 28151.4 22437.3 28713.6 20868.6 27184.5 31004.0 22890.6 20631.3 24583.2 25182.2 29105.0 15755.4 10882.4 39939.0 32356.5 18855.8 23592.8 36097.6 24719.1 26065.9 25505.5 19316.8 24385.9 261.0725101_MZ L-beta-aspartyl-L-glutamic acid Un 1.0 None None None None C9H14N2O7 None None None 12821.1 12358.2 14154.6 11788.2 12533.9 13751.3 13460.2 15030.4 11598.5 11074.4 12171.2 12522.4 11813.7 14288.2 13489.3 12502.1 13216.4 10632.8 12215.1 12787.2 13123.2 11022.4 11738.9 11719.7 12963.9 12028.0 14925.1 11850.1 10932.4 12370.6 12554.4 11140.0 10825.3 10445.0 11798.8 12217.2 11613.8 11441.4 9264.53 11439.5 11298.7 12079.7 264.9505318_MZ 2,3-Diphosphoglyceric acid Un 1.0 None None None None 2,3-Bisphosphoglycerate (2,3-BPG, also known as 2,3-diphosphoglycerate or 2,3-DPG) is a three carbon isomer of the glycolytic intermediate 1,3-bisphosphoglycerate and is present at high levels in the human red blood cell (RBC; erythrocyte)--at the same molar concentration as hemoglobin. It is notable because it binds to deoxygenated hemoglobin in RBCs. In doing so, it allosterically upregulates the ability of RBCs to release oxygen near tissues that need it most. Its function was discovered in 1967 by Reinhold Benesch and Ruth Benesch. C3H8O10P2, Glyceric acid 1,3-biphosphate None None None 5933.58 6677.95 6927.33 7155.71 8570.14 7609.0 9393.8 7705.39 6565.69 10107.8 6012.91 7351.29 7700.22 6883.53 10364.5 9931.15 7588.31 5977.92 6984.13 12902.8 6273.1 5783.09 5819.81 6155.74 9401.24 5816.98 9773.14 6073.11 5434.04 5878.25 10401.6 11852.3 7110.43 7181.41 6257.82 5720.54 6246.49 6334.08 7044.36 6283.02 9451.85 5669.71 265.0826160_MZ 5,6-Dihydrouridine Un 1.0 None None None None Dihydrouridine is a pyrimidine which is the result of adding two hydrogen atoms to a uridine. Dihydrouridine is found only in tRNA molecules. An inhibitor of nucleotide metabolism. C9H14N2O6, L-alpha-Aspartyl-L-hydroxyproline None None None 11864.6 14981.8 20181.8 12396.3 15607.6 16434.8 18347.0 9052.34 14887.8 13161.3 15261.7 20995.2 10940.2 13663.3 14756.8 19418.0 17778.6 7387.14 16232.5 17172.2 15984.2 12696.9 19687.2 16848.1 14745.0 11474.0 23848.7 11692.7 15816.7 14988.7 22752.5 16239.9 13816.4 13109.4 13425.7 9307.0 10766.0 15735.4 7529.53 12695.8 14484.9 11660.8 266.0563814_MZ 2-Amino-4-oxo-6-(1',2'-dioxoprolyl)-7,8-dihydroxypteridine Un 1.0 None None None None This compound It is a byproduct of 6-pyruvoyltetrahydropterin synthase (EC 4.2.3.12), and associated with 6-Pyruvoyltetrahydropterin synthase deficiency (an autosomal recessive disorder that causes malignant hyperphenylalaninemia due to tetrahydrobiopterin deficiency). (Wikipedia). C9H9N5O5 None None None 10020.1 7335.78 6975.13 6634.93 6471.43 9065.24 7710.4 7793.21 4968.72 6036.64 6479.2 5297.4 8208.02 6617.42 5742.45 10679.8 6832.78 9286.62 6760.21 10112.5 8348.22 4690.98 7091.37 7512.2 7046.95 5570.37 7644.13 7040.11 5790.37 7088.16 11248.1 6936.99 4815.21 6133.99 6282.94 7187.74 5142.48 5771.05 4200.89 6953.12 10836.0 7380.06 266.0891179_MZ Adenosine Un 1.0 None None None None Adenosine is a nucleoside that is composed of adenine and d-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. For instance, adenosine plays an important role in energy transfer - as adenosine triphosphate (ATP) and adenosine diphosphate (ADP). It also plays a role in signal transduction as cyclic adenosine monophosphate, cAMP. Adenosine itself is both a neurotransmitter and potent vasodilator. When administered intravenously, adenosine causes transient heart block in the AV node. Because of the effects of adenosine on AV node-dependent supraventricular tachycardia, adenosine is considered a class V antiarrhythmic agent. C10H13N5O4, Deoxyguanosine, Neuraminic acid None None None 17105.5 20243.3 18532.1 24096.1 21511.3 20469.4 21686.4 16611.0 21721.8 20333.7 20592.1 21980.1 18760.1 20339.9 28161.6 21220.4 22651.8 27411.6 23504.1 21029.5 20847.0 22784.9 19057.8 22209.6 22642.7 22374.6 27879.0 27262.7 30593.3 24778.8 19231.7 22818.8 20611.7 19080.0 44883.7 20598.0 26125.4 21628.2 37172.3 21163.8 20793.1 19922.6 266.1327759_MZ Hydroxybutyrylcarnitine Un 1.0 None None None None C11H21NO5 None None None 7775.94 2516.69 2716.26 3229.61 2230.29 4486.91 2601.58 2728.35 2190.73 3514.91 3963.98 2131.09 1688.75 7100.55 2414.35 2533.36 2818.82 2200.72 2336.71 4224.72 3431.47 2916.89 4053.81 3361.83 2478.03 2666.06 2600.83 2412.44 2500.42 8734.67 4109.41 2251.7 2158.83 2980.8 2513.57 2841.14 2782.7 2153.58 1726.51 2467.96 3613.63 2459.32 267.0734580_MZ Inosine Un 1.0 None None None None Inosine is a purine nucleoside that has hypoxanthine linked by the N9 nitrogen to the C1 carbon of ribose. It is an intermediate in the degradation of purines and purine nucleosides to uric acid and in pathways of purine salvage. It also occurs in the anticodon of certain transfer RNA molecules. (Dorland, 28th ed). C10H12N4O5, Allopurinol riboside, Arabinosylhypoxanthine None None None 529905.0 391010.0 447951.0 496637.0 506930.0 1435800.0 900236.0 340878.0 805286.0 1578710.0 743898.0 1615600.0 847124.0 580942.0 1063880.0 1036970.0 401432.0 1953260.0 1237260.0 772012.0 763761.0 640724.0 783590.0 625213.0 880305.0 895105.0 930008.0 1159910.0 843973.0 1371360.0 506414.0 1460660.0 667328.0 505427.0 849399.0 1748260.0 870379.0 604041.0 790641.0 1384770.0 1245530.0 1182130.0 267.1068861_MZ 6-Hydroxymelatonin Un 1.0 None None None None Melatonin is a hormone that is metabolized by cytochrome P450 (CYP) 1A2 to its main primary metabolite 6-hydroxymelatonin. (PMID 11452239). C13H16N2O3 None None None 38784.6 19211.8 27040.4 25861.5 23207.8 71881.3 44809.7 19211.5 35322.7 74036.8 36495.0 75146.8 40693.7 25369.8 52040.6 51677.7 19419.1 79375.6 52691.6 38481.9 33525.9 27292.1 43775.9 32532.6 48632.9 42153.0 41487.3 54997.0 38254.4 74948.2 25051.1 72595.9 30881.0 23005.4 40129.8 77574.2 38967.5 30327.0 35074.7 66706.3 55425.2 56187.9 267.2697431_MZ Stearaldehyde Un 1.0 None None None None Stearaldehyde or octadecanal is a normal long chain fatty aldehyde that can be found in total lipid extracts of muscle tissue. Stearaldehyde can also be found in the plasma of patients with Sjogren-Larsson syndrome. Sjogren-Larsson syndrome (SLS) is an autosomal recessively inherited neurocutaneous disorder caused by a deficiency of the microsomal enzyme fatty aldehyde dehydrogenase (FALDH). (PMID 14564703, 11408337). Octadecanal is often used as the substrate of choice to test FALDH activity in patients suspected of having Sjogren-Larsson syndrome. C18H36O None None None 2180.47 2315.73 2176.17 1954.74 2267.93 2355.63 2538.43 2458.26 2179.01 1994.0 2334.72 2456.66 1824.68 2353.69 2174.21 2026.03 2118.53 2966.94 1940.94 2407.12 2092.19 2033.75 2100.94 2371.12 2064.65 2052.82 1936.95 2541.43 2086.69 2462.11 2069.16 1732.11 2228.41 2084.59 2306.28 2268.47 2142.99 2016.65 2255.35 2206.21 2219.79 2316.36 269.2119761_MZ 3-Oxohexadecanoic acid Un 1.0 None None None None 3-Oxo-hexadecanoic acid is an intermediate in fatty acid biosynthesis. Specifically, 3-Oxo-hexadecanoic acid is converted from Malonic acid via three enzymes; 3-oxoacyl-[acyl-carrier-protein] synthase, fatty-acid Synthase and beta-ketoacyl -acyl-carrier-protein synthase II. (EC:2.3.1.41, E.C: 2.3.1.85, 2.3.1.179). C16H30O3 None None None 79599.1 76584.6 82139.1 67385.7 68915.9 72748.1 79695.4 109506.0 67421.9 65760.2 76530.6 57282.5 55969.4 80826.1 74327.8 55877.9 150150.0 68488.5 61062.6 81425.5 74914.4 52428.8 74673.0 84750.4 62229.2 54891.4 66420.0 72298.6 49403.8 87862.9 51688.9 48540.1 53718.6 61282.7 54679.7 71230.3 53752.6 54035.1 58698.2 72606.9 46244.5 63515.8 269.2480955_MZ Heptadecanoic acid Un 1.0 None None None None Heptadecanoic acid is a fatty acid of exogenous (primarily ruminant) origin. Many odd length long chain amino acids are derived from the consumption of dairy fats (milk and meat). Heptadecanoic acid constitutes 0.61% of milk fat and 0.83% of ruminant meat fat. The content of heptadecanoic acid in the subcutaneous adipose tissue of humans appears to be a good biological marker of long-term milk fat intake in free-living individuals in populations with high consumption of dairy products. (PMID 9701185). C17H34O2 None None None 180186.0 194555.0 172648.0 173111.0 173066.0 173585.0 184767.0 210431.0 167866.0 181427.0 201550.0 184420.0 160908.0 186804.0 161604.0 160838.0 199747.0 271070.0 155087.0 208944.0 174095.0 154441.0 173994.0 190266.0 171536.0 160673.0 161963.0 208503.0 158831.0 190670.0 156495.0 152096.0 175896.0 181465.0 155490.0 190423.0 141190.0 179456.0 175259.0 168735.0 139178.0 165495.0 270.1835173_MZ Dextromethorphan Un 1.0 None None None None Dextromethorphan is an antitussive drug that is found in many over-the-counter cold and cough preparations, usually in the form of dextromethorphan hydrobromide. Dextromethorphan is a salt of the methyl ether dextrorotatory isomer of levorphanol, a narcotic analgesic. Dextromethorphan occurs as white crystals, is sparingly soluble in water, and freely soluble in alcohol. The drug is dextrorotatory in water (at 20 degrees Celsius, Sodium D-line) with a specific rotation of +27.6 degrees. Following oral administration, dextromethorphan is rapidly absorbed from the gastrointestinal tract, where it enters the bloodstream and crosses the blood-brain barrier. Dextromethorphan shows high affinity binding to several regions of the brain, including the medullary cough center. The first-pass through the hepatic portal vein results in some of the drug being metabolized into an active metabolite of dextromethorphan, dextrorphan, the 3-hydroxy derivative of dextromethorphan. The therapeutic activity of dextromethorphan is believed to be caused by both the drug and this metabolite. Dextromethorphan is predominantly metabolized by the liver, by various hepatic enzymes. Through various pathways, the drug undergoes (O-demethylation (which produces dextrorphan), N-demethylation, and partial conjugation with glucuronic acid and sulfate ions. The inactive metabolite (+)-3-hydroxy-N-methylmorphinan is formed as a product of DXM metabolism by these pathways. One well known metabolic catalyst involved is a specific cytochrome P450 enzyme known as 2D6, or CYP2D6. A significant portion of the population has a functional deficiency in this enzyme (and are known as poor CYP2D6 metabolizers). As CYP2D6 is the primary metabolic pathway in the inactivation of dextromethorphan, the duration of action and effects of dextromethorphan are significantly increased in such poor metabolizers. Deaths and hospitalizations have been reported in recreational use by poor CYP2D6 metabolizers. -- Wikipedia. This compound is an NMDA receptor antagonist (receptors, N-methyl-D-aspartate) and acts as a non-competitive channel blocker. It is also used to study the involvement of glutamate receptors in neurotoxicity. [PubChem] C18H25NO None None None 2692.34 2472.01 2824.71 3811.22 2720.3 3185.46 3356.38 5029.0 1996.86 2539.37 3083.17 2715.5 1394.49 2547.88 3157.49 2311.19 5483.0 1685.57 2639.8 3000.79 2578.56 2278.66 3027.03 2677.05 3103.08 3791.82 2720.66 2940.65 1983.86 3480.19 2622.83 2978.62 1919.65 2547.95 2854.89 3028.05 2143.39 1993.03 1723.54 2490.0 2040.16 2201.21 270.2072284_MZ Tridecanoylglycine Un 1.0 None None None None Tridecanoylglycine is an acylglycine with C-13 fatty acid group as the acyl moiety. Acylglycines 1 possess a common amidoacetic acid moiety and are normally minor metabolites of fatty acids. Elevated levels of certain acylglycines appear in the urine and blood of patients with various fatty acid oxidation disorders. They are normally produced through the action of glycine N-acyltransferase which is an enzyme that catalyzes the chemical reaction: acyl-CoA + glycine ↔ CoA + N-acylglycine. C15H29NO3 None None None 51149.4 48569.9 24618.1 52668.6 46739.0 53233.2 53008.5 50609.5 23289.5 53494.5 60589.3 5355.24 30511.6 101123.0 43604.5 35398.5 57700.1 38156.3 51717.1 45526.9 48560.7 5362.65 48730.7 63031.4 40223.1 6324.52 42128.7 33636.8 4522.08 52948.5 38383.3 34971.4 3044.0 37904.7 4875.19 69978.9 22229.8 4406.28 34062.3 50147.3 46454.9 53276.3 271.0783155_MZ Deoxyinosine Un 1.0 None None None None Deoxyinosine is a nucleoside that is formed when hypoxanthine is attached to a deoxyribose ring (also known as a ribofuranose) via a beta-N9-glycosidic bond. Deoxyinosine is found in DNA while Inosine is found in RNA. Inosine is a nucleic acid important for RNA editing. Adenosine deaminase (ADA) catalyzes the conversion of adenosine and deoxyadenosine to inosine and deoxyinosine, respectively. ADA-deficient individuals suffer from severe combined immunodeficiency (SCID) and are unable to produce significant numbers of mature T or B lymphocytes. This occurs as a consequence of the accumulation of ADA substrates or their metabolites. Inosine is also an intermediate in a chain of purine nucleotides reactions required for muscle movements. C10H12N4O4 None None None 8005.77 7010.88 12551.1 12098.8 11236.2 9305.07 9788.56 11787.9 6857.39 7864.49 8834.62 7330.61 6951.95 9542.55 12305.8 11267.9 19101.7 4700.4 8080.07 8245.65 8530.36 7251.27 8332.22 6985.32 8472.95 7449.51 10442.5 8104.44 6361.65 9764.15 8646.3 9156.38 6313.8 6161.69 7267.94 8230.39 6412.0 6840.01 5369.39 8055.65 7236.7 7258.23 271.1726068_MZ Estradiol Un 1.0 None None None None Estradiol is the most potent form of mammalian estrogenic steroids. Estradiol is produced in the ovaries. The ovary requires both luteinizing hormone (LH) and follicle-stimulating hormone (FSH) to produce sex steroids. LH stimulates the cells surrounding the follicle to produce progesterone and androgens. The androgens diffuse across the basement membrane to the granulosa cell layer, where, under the action of FSH, they are aromatized to estrogens, mainly estradiol. The ovary shows cyclical activity, unlike the testis that is maintained in a more or less constant state of activity. Hormone secretions vary according to the phase of the menstrual cycle. In the developing follicle LH receptors (LH-R) are only located on the thecal cells and FSH receptors (FSHR) on the granulosa cells. The dominant pre-ovulatory follicle develops LH-Rs on the granulosa cells prior to the LH surge. Thecal cells of the preovulatory follicle also develop the capacity to synthesize estradiol and this persists when the thecal cells become incorporated into the corpus luteum. After ovulation, the empty follicle is remodelled and plays an important role in the second half or luteal phase of the menstrual cycle. This phase is dominated by progesterone and, to a lesser extent, estradiol secretion by the corpus luteum. estradiol is also synthesized locally from cholesterol through testosterone in the hippocampus and acts rapidly to modulate neuronal synaptic plasticity. Localization of estrogen receptor alpha (ERalpha) in spines in addition to nuclei of principal neurons implies that synaptic ERalpha is responsible for rapid modulation of synaptic plasticity by endogenous estradiol. estradiol is a potent endogenous antioxidant which suppresses hepatic fibrosis in animal models, and attenuates induction of redox sensitive transcription factors, hepatocyte apoptosis and hepatic stellate cells activation by inhibiting a generation of reactive oxygen species in primary cultures. This suggests that the greater progression of hepatic fibrosis and hepatocellular carcinoma in men and postmenopausal women may be due, at least in part, to lower production of estradiol and a reduced response to the action of estradiol. estradiol has been reported to induce the production of interferon (INF)-gamma in lymphocytes, and augments an antigen-specific primary antibody response in human peripheral blood mononuclear cells. IFN-gamma is a potent cytokine with immunomodulatory and antiproliferative properties. Therefore, female subjects, particularly before menopause, may produce antibodies against hepatitis B virus e antigen and hepatitis B virus surface antigen at a higher frequency than males with chronic hepatitis B virus infection. The estradiol-Dihydrotestosterone model of prostate cancer (PC) proposes that the first step in the development of most PC and breast cancer (BC) occurs when aromatase converts testosterone to estradiol. (PMID: 17708600, 17678531, 17644764). C18H24O2 None None None 4597.55 5123.06 4157.52 7606.67 5768.72 5200.26 5072.14 6199.19 4412.24 4462.54 5648.64 3692.9 4617.94 4901.01 5079.49 4753.07 9072.8 2011.37 5353.53 4639.47 4008.55 3102.03 4956.59 4403.19 8401.16 3299.42 4972.19 3793.81 2859.63 5924.34 6582.13 5945.18 2994.85 4476.44 3226.79 4258.79 3572.97 3749.66 7232.17 4877.64 8181.71 5057.42 271.2275128_MZ (R)-3-Hydroxy-hexadecanoic acid Un 1.0 None None None None (R)-3-Hydroxy-hexadecanoic acid is an intermediate in fatty acid biosynthesis. Specifically, (R)-3-Hydroxy-hexadecanoic acid is converted from 3-Oxo-tetradecanoic acid via fatty-acid Synthase and 3-oxoacyl- [acyl-carrier-protein] reductase. (EC: 2.3.1.85 and EC: 2.3.1.41). C16H32O3 None None None 48204.8 45506.7 39161.2 40647.0 41602.6 46900.0 47019.6 50807.3 37825.3 41630.0 45603.9 37113.8 30971.1 51051.7 40754.7 33360.6 61013.9 39889.6 37855.1 40831.4 43743.6 29645.0 44697.5 48629.8 35650.2 33562.1 36498.0 43343.8 29412.3 53075.7 32124.0 29259.7 29956.3 36137.9 33478.0 40541.6 31724.0 30697.1 34580.6 41021.3 29727.4 36664.6 272.1872802_MZ Heptanoylcarnitine Un 1.0 None None None None C14H27NO4 None None None 3391.98 3139.02 3198.18 6639.24 2729.54 3601.84 4582.34 5737.45 2792.87 2417.99 4016.07 3096.77 3306.17 3958.42 2723.58 3600.43 5007.97 2458.4 3263.0 3039.31 3228.51 2660.56 4878.44 3172.37 3272.01 2788.78 2837.63 3863.36 2336.61 3883.58 3190.09 4318.67 1966.07 3245.28 2588.44 3547.5 2704.4 3542.97 1767.33 3385.23 2664.02 3296.64 273.1699087_MZ 3-Hydroxytetradecanedioic acid Un 1.0 None None None None 3-Hydroxytetradecanedioic acid is an unusual 3-hydroxydicarboxylic acid human metabolite found occasionally in urine. (PMID 2925825) High levels of 3-Hydroxytetradecanedioic acid (and other 3-hydroxydicarboxylic acids) were detected in the urine of a patient with 3-hydroxydicarboxylic aciduria (PMID 1507493), due to acute intoxication associated with hopantenate occurs owing to pantothenic acid deficiency or the inhibition of CoA-requiring reactions during stress, i.e., infection, prolonged fasting, or malnutrition (PMID 2026687), and in a patient with thanatophoric dysplasia due to enhanced but incomplete oxidation of fatty acid, a consequence of a heterozygous point mutation, S249C in the fibroblast growth factor receptor 3 gene. (PMID 11879084). C14H26O5 None None None 7211.96 8887.97 7269.28 8177.53 6092.2 7788.7 6752.49 9810.3 4431.24 6762.73 6288.49 4628.73 4358.81 7328.74 7505.45 8548.04 14497.7 4468.63 5090.36 7789.39 5698.08 3763.6 6245.23 5568.6 6181.83 4376.45 6921.76 5063.04 4499.8 9385.63 6222.06 5465.06 3262.05 5676.58 5761.87 5897.03 4172.12 3537.89 4413.21 5659.52 4390.0 5657.29 273.1867969_MZ Nandrolone Un 1.0 None None None None Nandrolone is a C18 steroid with androgenic and anabolic properties. It is generally prepared from alkyl ethers of estradiol to resemble testosterone but less one carbon at the 19 position. -- Pubchem; Nandrolone is an anabolic steroid occurring naturally in the human body, albeit in small quantities. Nandrolone is most commonly sold commercially as its decanoate ester (Deca-Durabolin) and less commonly as a phenylpropionate ester (Durabolin). Nandrolone use is indirectly detectable in urine tests by testing for the presence of 19-norandrosterone, a metabolism product of this molecule. The International Olympic Committee has set a limit of 2 ng per ml of urine as the upper limit, beyond which an athlete is suspected of doping. -- Wikipedia. C18H26O2 None None None 7077.03 7513.58 6051.66 6842.51 6426.44 6860.2 6630.79 7088.32 7368.69 6419.32 7189.93 7382.68 4968.25 7247.77 7230.58 6447.54 8626.57 4399.08 5795.27 6434.5 5734.19 5273.03 7358.51 5779.98 6672.74 5555.56 6395.7 5981.4 4830.35 7288.83 6001.91 4902.05 5483.54 5677.73 4941.96 5630.14 5519.27 5491.38 5521.66 5841.18 4814.83 5143.08 274.1042245_MZ Gamma-Glutamylglutamine Un 1.0 None None None None gamma-Glutamylglutamine has been identified in plasma and cerebrospinal fluid from hyperammonaemic patients. C10H17N3O6, Norophthalmic acid None None None 13461.5 14984.7 15105.5 11326.3 12438.3 22637.8 13167.3 27855.8 13568.2 10911.2 11480.8 14141.0 9406.43 15409.1 16981.7 14461.6 17102.2 9181.98 10542.0 10851.3 13312.9 12353.4 12338.8 13233.1 11152.3 15693.3 13636.4 11433.2 13122.8 13739.0 13463.2 10947.5 9889.98 11192.4 12294.3 14765.8 11581.5 11392.2 6881.56 11624.1 9180.39 11129.1 275.0171116_MZ 6-Phosphogluconic acid Un 1.0 None None None None Intermediate in the Pentose phosphate pathway (KEGG). C6H13O10P None None None 24517.1 16760.1 29482.7 13076.8 34189.9 20492.1 28334.4 24855.1 30509.2 20412.0 24361.0 24073.1 22696.7 26023.6 34973.4 12746.6 28268.2 26420.4 34497.3 28541.2 24584.7 28353.2 19883.0 25374.9 35442.0 22156.2 28852.3 19198.0 19634.7 29417.4 18412.8 14597.6 42221.3 25125.7 17568.9 16640.4 32992.6 31480.5 21611.8 21824.1 21947.7 20708.8 275.0922980_MZ Gamma Glutamylglutamic acid Un 1.0 None None None None Gamma Glutamylglutamic acid is made of two glutamic acid molecules. Glutamic acid (Glu), also referred to as glutamate (the anion), is one of the 20 proteinogenic amino acids. It is not among the essential amino acids. Glutamate is a key molecule in cellular metabolism. In humans, dietary proteins are broken down by digestion into amino acids, which serves as metabolic fuel or other functional roles in the body. Glutamate is the most abundant fast excitatory neurotransmitter in the mammalian nervous system. At chemical synapses, glutamate is stored in vesicles. Nerve impulses trigger release of glutamate from the pre-synaptic cell. In the opposing post-synaptic cell, glutamate receptors, such as the NMDA receptor, bind glutamate and are activated. Because of its role in synaptic plasticity, it is believed that glutamic acid is involved in cognitive functions like learning and memory in the brain. Glutamate transporters are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, they can work in reverse and excess glutamate can accumulate outside cells. This process causes calcium ions to enter cells via NMDA receptor channels, leading to neuronal damage and eventual cell death, and is called excitotoxicity. The mechanisms of cell death include: * Damage to mitochondria from excessively high intracellular Ca2+. * Glu/Ca2+-mediated promotion of transcription factors for pro-apoptotic genes, or downregulation of transcription factors for anti-apoptotic genes. Excitotoxicity due to glutamate occurs as part of the ischemic cascade and is associated with stroke and diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimer's disease. glutamic acid has been implicated in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart, and this firing pattern is similar to what is known as paroxysmal depolarizing shift in epileptic attacks. This change in the resting membrane potential at seizure foci could cause spontaneous opening of voltage activated calcium channels, leading to glutamic acid release and further depolarization. (http://en.wikipedia.org/wiki/Glutamic_acid). C10H16N2O7 None None None 8349.31 9078.34 9871.69 9698.49 13499.9 10914.6 11636.7 10233.9 7716.49 8576.51 9964.7 8078.19 5940.8 10022.8 14306.4 10805.1 10485.6 6136.9 8205.89 8435.57 8205.64 6551.53 8008.34 8307.4 9290.29 6862.05 11092.8 7783.58 6654.54 10544.4 8832.56 8931.85 6192.34 6641.43 6936.05 8417.29 6250.69 7010.84 4932.58 8812.73 6838.07 7017.31 275.1249174_MZ Saccharopine Un 1.0 None None None None Saccharopine is an intermediate in the degradation of lysine, formed by condensation of lysine and alpha-ketoglutarate. The saccharopine pathway is the main route for lysine degradation in mammal and its first two reactions are catalyzed by enzymatic activities known as lysine-oxoglutarate reductase (LOR) and saccharopine dehydrogenase (SDH), which reside on a single bifunctional polypeptide (EC EC 1.5.1.8, LOR/SDH). The reactions involved by saccharopine dehydrogenases have a very strict substrate specificity for L-lysine, 2-oxoglutarate and NADPH. LOR/SDH has been detected in a number of mammalian tissues, mainly in the liver and kidney, contributing not only to the general nitrogen balance in the organism but also to the controlled conversion of lysine into ketone bodies. A tetrameric form has also been observed in human liver and placenta. LOR activity has also been detected in brain mitochondria during embryonic development, and this opens the question of whether the degradation of lysine has any functional significance during brain development and puts a new focus on the nutritional requirements for lysine in gestation and infancy. Finally, LOR and/or SDH deficiencies seem to be involved in a human autosomic genetic disorder known as familial hyperlysinemia, which is characterized by serious defects in the functioning of the nervous system, and characterized by deficiency in lysine-ketoglutarate reductase, saccharopine dehydrogenase, and saccharopine oxidoreductase activities. Saccharopinuria (high amounts of saccharopine in the urine) and saccharopinemia (an excess of saccharopine in the blood) are conditions present in some inherited disorders of lysine degradation. (PMID: 463877, 10567240, 10772957, 4809305). C11H20N2O6 None None None 14180.0 29983.5 22061.6 27566.9 19202.9 23938.5 20820.8 25811.4 17943.6 12858.4 17644.9 40074.5 7515.71 16128.0 21660.5 28281.1 18892.8 26902.6 8411.85 19299.3 12393.9 14047.3 14171.7 16007.4 24146.4 12537.9 27029.1 18123.0 19707.5 25961.2 27946.2 14570.6 22292.9 17514.5 19502.9 13756.0 18717.0 22714.9 18235.4 15399.1 15222.7 9609.02 275.2010857_MZ Stearidonic acid Un 1.0 None None None None Stearidonic acid is found in dietary plant oils which are metabolized to longer-chain, more unsaturated (n-3) PUFA. These oils appear to possess hypotriglyceridemic properties typically associated with fish oils.(PMID: 15173404). Stearidonic acid may be used as a precursor to increase the EPA content of human lipids and that combinations of gamma-linolenic acid and stearidonic acid eicosapentaenoic acid can be used to manipulate the fatty acid compositions of lipid pools in subtle ways. Such effects may offer new strategies for manipulation of cell composition in order to influence cellular responses and functions in desirable ways. (PMID: 15120716). C18H28O2, 19-Norandrosterone, 19-Nor-5-androstenediol, 19-Noretiocholanolone None None None 6088.47 6983.02 5507.83 15684.9 7077.89 8583.08 7569.62 6002.56 7261.21 7520.6 7800.21 7948.88 4627.93 6782.01 7979.32 5859.08 8880.83 5594.9 8375.52 6499.26 6218.38 4715.92 7128.6 6067.67 5978.73 5406.0 7022.18 6929.09 4291.58 7985.1 5986.43 4890.99 5207.62 6249.33 5392.72 6695.55 4939.18 6142.37 4269.85 6614.66 5269.27 5873.07 275.2374322_MZ 5a-Androstan-3b-ol Un 1.0 None None None None C19H32O None None None 1386.01 1321.47 1145.99 1481.24 1331.76 1346.38 1554.31 1483.27 1343.21 1252.91 1473.81 1545.16 1714.16 1497.79 1253.4 1148.2 1272.02 2140.1 1161.34 1700.55 1312.99 1259.67 1331.43 1446.79 1274.87 1240.32 1249.88 1614.54 1133.99 1342.26 1290.26 1091.41 1300.94 1355.74 1206.53 1422.17 1138.66 1413.91 1230.23 1342.67 1566.02 1412.83 276.9040357_MZ PPPi Un 1.0 None None None None H5O10P3 None None None 12344.3 13141.8 12996.7 12914.1 13096.0 12716.4 12809.2 13385.3 14152.8 14101.0 12770.3 13547.5 13690.1 12327.0 13445.1 11241.7 13538.9 15675.7 14642.2 13955.1 12372.3 13569.4 13225.7 13395.3 13627.2 13088.0 13124.0 13830.7 14535.6 13516.3 11445.3 11281.4 14042.4 15199.4 13938.6 13790.0 14265.3 13657.4 18152.6 13626.9 11924.4 13465.7 277.1440343_MZ Alpha-CEHC Un 1.0 None None None None 2,5,7,8-tetramethyl-2-(2'-carboxyethyl)-6-hydroxychroman (alpha-CEHC) has been identified as a major water-soluble metabolite of vitamin E, which circulates in the blood and is excreted with the urine. (PMID 12420750). C16H22O4, Monoethylhexyl phthalic acid None None None 17833.2 17841.5 16597.6 18514.9 20081.3 22289.6 24762.6 21492.4 12673.1 18684.2 20034.1 12409.9 12420.9 20346.0 21210.4 17355.7 28003.1 16337.2 17122.3 19913.6 16638.2 9733.34 17161.2 18175.1 15976.8 10139.4 17750.6 15776.3 9217.68 21484.7 15942.2 14256.3 10764.6 14690.2 10091.7 15874.7 9970.17 9714.03 10087.0 17582.8 18097.3 15522.1 277.1551852_MZ Leucyl-phenylalanine Un 1.0 None None None None Leucyl-phenylalanine (leu-phe) is a peptide made of leucine and phenylalanine molecules. They are an essential amino acids. C15H22N2O3 None None None 7807.91 7856.14 8547.89 7009.97 8435.17 7562.6 6770.59 7045.62 9304.13 6693.4 8258.84 8875.73 4812.42 8678.73 8043.07 6422.6 8219.04 4965.47 5558.64 6002.29 7096.69 9911.36 6469.57 8073.5 6444.63 9287.53 6665.01 11004.6 11148.7 7180.95 6032.65 5616.54 6381.21 5466.42 10601.1 9086.41 6283.2 6187.47 4968.92 9286.0 4563.09 7129.57 277.2169946_MZ Alpha-Linolenic acid Un 1.0 None None None None Alpha-linolenic acid (ALA) is a polyunsaturated fatty acid (PUFA). It is a member of the group of essential fatty acids called omega-3 fatty acids. Alpha-linolenic acid, in particular, is not synthesized by mammals and therefore is an essential dietary requirement for all mammals. Certain nuts (English walnuts) and vegetable oils (canola, soybean, flaxseed/linseed, olive) are particularly rich in alpha-linolenic acid (ALA). Omega-3 fatty acids get their name based on the location of one of their first double bond. In all omega-3 fatty acids, the first double bond is located between the third and fourth carbon atom counting from the methyl end of the fatty acid (n-3). Although humans and other mammals can synthesize saturated and some monounsaturated fatty acids from carbon groups in carbohydrates and proteins, they lack the enzymes necessary to insert a cis double bond at the n-6 or the n-3 position of a fatty acid. Omega-3 fatty acids like a-linolenic acid are important structural components of cell membranes. When incorporated into phospholipids, they affect cell membrane properties such as fluidity, flexibility, permeability and the activity of membrane bound enzymes. Omega-3 fatty acids can modulate the expression of a number of genes, including those involved with fatty acid metabolism and inflammation. Alpha linolenic acid and other omega 3 fatty acids may regulate gene expression by interacting with specific transcription factors, including peroxisome proliferator activated receptors (PPARs) and liver X receptors (LXRs). C18H30O2, Gamma-Linolenic acid None None None 39456.1 37960.8 33107.9 111530.0 40854.7 80766.2 93133.7 50024.6 57953.5 51994.4 41511.3 41932.1 47101.0 58641.8 61405.5 33333.7 63795.4 76358.0 77026.9 64062.3 39996.9 25553.7 46752.2 42240.7 43811.7 30726.0 41767.6 60888.7 26621.9 58231.9 50031.3 25353.6 35144.0 40128.6 21633.8 78375.2 33079.2 39106.3 30678.4 44746.0 79482.3 71699.9 279.2329303_MZ Linoleic acid Un 1.0 None None None None Linoleic acid is a doubly unsaturated fatty acid, also known as an omega-6 fatty acid, occurring widely in plant glycosides. In this particular polyunsaturated fatty acid (PUFA), the first double bond is located between the sixth and seventh carbon atom from the methyl end of the fatty acid (n-6). Linoleic acid is an essential fatty acid in human nutrition because it cannot be synthesized by humans. It is used in the biosynthesis of prostaglandins (via arachidonic acid) and cell membranes. (From Stedman, 26th ed). C18H32O2, Bovinic acid, 9E,11E-Octadecadienoic acid, 10E,12Z-Octadecadienoic acid, Linoelaidic acid None None None 638872.0 588143.0 554130.0 1065320.0 688682.0 1195630.0 1472740.0 910809.0 787920.0 647272.0 640259.0 758791.0 1021150.0 1015920.0 929421.0 479065.0 999356.0 1547800.0 838979.0 1270650.0 603922.0 396019.0 746569.0 722053.0 807670.0 477946.0 577590.0 1097540.0 447421.0 778984.0 1003900.0 406006.0 697344.0 586176.0 296063.0 1165560.0 566879.0 789855.0 681613.0 620024.0 1581170.0 1102160.0 280.0852147_MZ 4-Hydroxyphenylacetylglutamine Un 1.0 None None None None 4-Hydroxyphenylacetylglutamine is involved in tyrosine and phenylalanine metabolism. C13H15NO6 None None None 3917.01 4039.95 4639.56 5050.82 4252.66 4688.57 4274.58 4035.73 3918.96 3952.09 3821.27 3845.33 3568.59 3936.47 4198.61 4423.88 5161.73 4115.65 4139.65 3867.06 4144.93 3415.59 4187.48 3910.77 3861.36 3931.55 4510.26 4004.19 3807.53 5008.02 3858.22 4102.41 3656.17 3840.3 4408.77 4627.01 3939.86 3512.08 2763.27 3852.48 3299.38 3436.68 280.1030489_MZ 1-Methyladenosine Un 1.0 None None None None 1-methyladenosine is one of the modified nucleosides, the levels of which are elevated in urine of patients with malignant tumors. Examination of expression of 1-methyladenosine is expected to be useful for the histological diagnosis of intraocular tumors. (PMID 8434538). C11H15N5O4, N6-Methyladenosine, 2'-O-Methyladenosine, 3'-O-Methyladenosine None None None 6761.31 7680.4 8495.25 6986.92 7275.5 8469.83 7445.65 6276.54 8318.27 6379.86 7564.76 7754.38 5524.89 6709.28 6507.45 6824.49 6312.35 4786.34 7438.71 5627.49 7520.59 7090.11 7746.11 8527.34 5621.33 7251.94 7357.0 8123.34 7983.58 7746.59 6089.39 6212.04 7250.16 6621.59 9433.91 10497.6 6004.25 6404.94 4115.89 7241.35 4858.66 5851.4 280.1265649_MZ Gamma glutamyl ornithine Un 1.0 None None None None Gamma glutamyl ornithine is found in human urine. - PubMed reference: 1148212. Gamma-glutamylornithine has been identified in urine from patients with the HHH syndrome (hyperornithinemia, hyperammonemia and homocitrullinuria) and with gyrate atrophy associated with hyperornithinemia. The amount of gamma-glutamylornithine excreted was 10-15 times higher than that excreted in normal subjects. - PubMed reference: 6547887. C10H19N3O5, Aspartylysine, Alpha-Aspartyl-lysine None None None 7230.51 5601.92 6397.58 6631.29 7174.9 7818.53 5214.99 4980.77 7023.29 6953.72 7627.79 7265.11 2539.56 8400.15 8072.54 4711.69 6360.57 2437.26 4121.02 3870.29 5284.64 6350.01 7435.03 6132.39 4488.1 5289.67 5972.97 5801.05 4916.43 9601.2 4166.7 4386.93 6028.69 4092.98 6907.74 4888.68 5502.04 6951.58 2901.99 6576.05 2981.25 3657.55 281.2486907_MZ Oleic acid Un 1.0 None None None None Oleic acid is an unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed) Biological Source: Major constituent of plant oils e.g. olive oil (about 80%), almond oil (about 80%) and many others, mainly as glyceride. Constituent of tall oil and present in fruits Use/Importance: Food additive. Oleic acid is used in manufacturing of surfactants, soaps, plasticizers. Emulsifying agent in foods and pharmaceuticals. Biological Use/Importance: Skin penetrant. Herbicide, insecticide, fungicide (Dictionary of Organic Compounds). Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colourless oil, although commercial samples may be yellowish. In chemical terms, oleic acid is classified as a monounsaturated omega-9 fatty acid. It has the formula CH3(CH2)7CH=CH(CH2)7COOH. The term oleic means related to, or derived from, oil or olive, the oil that is predominantly composed of oleic acid. (Wiki). C18H34O2, Elaidic acid, Vaccenic acid None None None 1263480.0 639767.0 829106.0 849762.0 1348280.0 2113640.0 1902250.0 1495400.0 1066550.0 1070450.0 1016610.0 953212.0 2444830.0 2066090.0 1903210.0 582517.0 621087.0 3776220.0 1069100.0 2112790.0 945841.0 733750.0 812035.0 1485940.0 1238580.0 1069590.0 808158.0 1710830.0 843911.0 755014.0 998947.0 619759.0 1633130.0 846964.0 581580.0 2201450.0 1053610.0 855437.0 1250510.0 921273.0 3279010.0 2608500.0 283.0679885_MZ Xanthosine Un 1.0 None None None None Xanthosine is produced by guanine-free mutants of bacteria e.g. Bacillus subtilis, Aerobacter aerogenes. Also reported from seeds of Trifolium alexandrinum Physical Description: Prismatic cryst. (H2O) (Chemnetbase) The deamination product of guanosine. Xanthosine monophosphate is an intermediate in purine metabolism, formed from IMP, and forming GMP.(Wikipedia). Xanthylic acid can be used in quantitative measurements of the Inosine monophosphate dehydrogenase enzyme activities in purine metabolism, as recommended to ensure optimal thiopurine therapy for children with acute lymphoblastic leukaemia (ALL). (PMID: 16725387). C10H12N4O6 None None None 46608.7 41580.1 31515.3 18659.5 29846.1 113623.0 50732.8 22928.5 59442.5 80595.5 55968.3 77749.4 62278.4 44429.6 50114.7 121415.0 20216.6 166004.0 114104.0 44414.0 62323.7 49363.0 96222.8 56531.0 38617.2 61170.9 43132.5 73506.3 42456.5 85511.3 34300.3 68216.0 39797.9 33259.6 38022.5 136435.0 52333.5 37561.7 22979.3 102011.0 67740.4 76108.2 283.0821277_MZ p-Cresol glucuronide Un 1.0 None None None None p-Cresol glucuronide is a glucuronide derivative a p-Cresol that is typically excreted in the urine. P-Cresol (the precursor of p-cresol sulfate (PCS) and p-cresol glucuronide (PCG)) is mainly generated as an end product of tyrosine biotransformation by anaerobic intestinal bacteria. During passage through the colonic mucosa and liver, sulfatation and glucuronidation generates p-Cresol sulfate (as the most preponderant metabolite) and p-Cresol glucuronide (at markedly lower concentrations) (PMID: 23826225). Cresols are known as methylphenols. Cresols are used to dissolve other chemicals, such as disinfectants and deodorizers. They are also used to make specific chemicals that kill insect pests. Cresol solutions are used as household cleaners and disinfectants such as Lysol. Cresol solutions can also be found in photographic developers. In the past, cresol solutions have been used as antiseptics in surgery, but they have been largely displaced in this role by less toxic compounds. Cresols are found in many foods and in wood and tobacco smoke, crude oil, coal tar, and in brown mixtures such as creosote, cresolene and cresylic acids, which are wood preservatives. Microbes in the soil and water produce cresols when they break down materials in the environment. Most exposures to cresols are at very low levels that are not harmful. When cresols are breathed, ingested, or applied to the skin at very high levels, they can be very harmful. Effects observed in people include irritation and burning of skin, eyes, mouth, and throat; abdominal pain and vomiting. Cresols are also a chemical component found in Sharpie Markers. P-cresol is a major component in pig odor. C13H16O7 None None None 23961.7 27183.2 25152.1 29184.9 23197.0 36480.7 17061.9 20666.8 19205.0 22741.0 17391.3 37668.9 19585.2 19520.2 35895.2 52591.1 18159.9 37021.6 26849.4 20763.1 16935.9 19089.1 29528.7 23317.4 16790.5 23170.3 23391.6 26369.3 30179.4 38114.6 47619.6 23715.1 17750.0 23602.4 23376.7 29051.2 20691.5 11351.6 14656.4 34284.3 25860.6 24471.3 283.2641168_MZ Stearic acid Un 1.0 None None None None Stearic acid, also called octadecanoic acid, is one of the useful types of saturated fatty acids that comes from many animal and vegetable fats and oils. It is a waxy solid, and its chemical formula is CH3(CH2)16COOH. Its name comes from the Greek word stear, which means tallow. Its IUPAC name is octadecanoic acid. -- Wikipedia. C18H36O2 None None None 8937440.0 9803980.0 8350100.0 8576700.0 8763890.0 7829240.0 9543260.0 10639700.0 8431670.0 8802610.0 10226000.0 9248230.0 8431240.0 9340930.0 7351990.0 7861470.0 9615680.0 14468000.0 7588620.0 10401200.0 8619590.0 7531790.0 8649140.0 9352820.0 8416670.0 7995000.0 7740130.0 10686800.0 7677600.0 9472950.0 7731840.0 7474370.0 8828550.0 9014580.0 7585930.0 9261560.0 7067220.0 8961050.0 8891030.0 8384640.0 6870380.0 8178640.0 284.0305575_MZ 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine Un 1.0 None None None None 2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine is an intermediate in purine metabolism. The enzyme phosphoribosylformylglycinamidine synthase [EC:6.3.5.3] catalyzes the production of this metabolite from N2-formyl-N1-(5-phospho-D-ribosyl)glycinamide. C6H12N3O8P None None None 5546.85 4944.68 6214.69 4792.99 5298.48 7503.73 5456.67 4084.68 7007.47 6112.15 5316.56 6384.79 6623.88 5246.34 6389.15 6754.27 4341.07 8088.19 7158.76 6398.75 5306.09 7062.74 5806.97 5428.05 5266.73 5522.83 5592.18 6242.8 6829.24 6273.69 4158.46 5643.65 6751.76 5219.41 7406.23 6575.91 6610.76 6939.7 4320.16 6517.48 5118.8 5396.48 285.2031695_MZ Hexadecanedioic acid Un 1.0 None None None None Hexadecanedioic acid is activated by mitochondrial and microsomal fractions in liver (PMID 4372285). It has an antitumor activity (PMID 14987827). C16H30O4 None None None 10439.6 10695.2 14477.4 10396.4 10845.4 10779.1 14124.6 24322.2 7420.21 9444.6 9323.44 6324.14 6976.06 10936.8 14891.8 11151.1 37763.4 8186.5 9743.72 13413.9 9661.32 4759.96 9227.95 10126.6 10794.2 6806.77 12201.2 9743.63 5861.9 12575.6 9286.13 8118.2 5508.51 7822.6 6933.85 10472.2 6349.0 5002.99 7632.29 9137.09 7243.58 8614.39 286.2019460_MZ L-Octanoylcarnitine Un 1.0 None None None None L-Octanoylcarnitine is the physiologically active form of octanoylcarnitine. (PMID 11274033). Octanoylcarnitine is detected in medium-chain acyl-CoA dehydrogenase (MCAD) deficiency. MCAD is characterized by intolerance to prolonged fasting, recurrent episodes of hypoglycemic coma with medium-chain dicarboxylic aciduria, impaired ketogenesis, and low plasma and tissue carnitine levels. (OMIM 201450). C15H29NO4 None None None 4483.97 4294.08 3976.49 5030.28 3605.16 4461.4 7313.88 6083.65 3199.14 4218.52 4274.14 1380.32 4370.04 5694.45 4278.68 4006.91 9296.44 5201.86 3684.92 4929.64 3978.51 2067.99 3736.15 4756.08 3552.48 1570.14 3378.97 3982.53 1748.49 4846.2 4377.68 3657.75 2472.2 4145.98 2734.63 6163.78 2438.27 1130.85 2620.82 4894.92 5965.2 4430.78 287.2410166_MZ All-trans-13,14-dihydroretinol Un 1.0 None None None None All-trans-13,14-dihydroretinol is involved in the retinol metabolism pathway. In this pathway, all-trans-13,14-dihydroretinol and an acceptor molecule is reversibly converted to retinol (vitamin A) plus reduced acceptor via the enzyme all-trans-retinol 13,14-reductase (EC 1.3.99.23). (KEGG). C20H32O None None None 1562.27 1022.63 3141.89 1200.98 1783.73 1206.33 7747.81 5697.75 872.55 981.339 1154.17 1021.84 4944.03 1857.07 1619.58 1040.88 7323.32 7680.0 1267.44 6140.63 1011.75 682.057 1031.34 1260.78 1376.48 889.332 1384.69 3219.65 709.536 1143.11 3586.94 755.732 1432.01 2989.11 692.453 1411.95 981.021 945.658 1457.65 1355.37 6846.42 1791.49 288.1200573_MZ Ophthalmic acid Un 1.0 None None None None Ophthalmic acid is an analogue of glutathione isolated from crystalline lens. C11H19N3O6 None None None 134409.0 111969.0 149645.0 254280.0 54106.7 76641.2 107784.0 214542.0 71109.0 117888.0 166427.0 110583.0 66952.5 110263.0 103847.0 73170.1 62618.0 46438.5 30495.4 47759.0 45605.5 66558.2 67588.3 68493.1 65655.8 258309.0 63423.6 51943.8 100605.0 72642.0 91440.1 61656.2 65367.1 67085.1 64188.6 66636.2 80566.0 64782.6 42396.4 111219.0 53123.7 85084.5 289.0325359_MZ D-Sedoheptulose 7-phosphate Un 1.0 None None None None D-Sedoheptulose 7-phosphate is an intermediate of the Pentose phosphate pathway (PPP) that has two functions: the generation of NADPH for reductive syntheses and oxidative stress responses within cells, and the formation of ribose residues for nucleotide and nucleic acid biosynthesis. (PMID 16055050)It is formed by transketolase and acted upon (degraded) by transaldolase. Sedoheptulose 7-phosphate can be increased in the blood of patients affected with a transaldolase deficiency (TALDO1; EC 2.2.1.2). (PMID 12881455) Sedoheptulose is a ketoheptose, a monosaccharide with seven carbon atoms and a ketone functional group. It is one of the few heptoses found in nature. (wikipedia). C7H15O10P None None None 110242.0 73633.1 131000.0 40017.0 102704.0 84362.8 142749.0 89690.7 131153.0 85360.7 110750.0 86316.3 154822.0 95015.8 158256.0 51536.0 116018.0 132348.0 143078.0 85756.3 112332.0 103356.0 109154.0 119478.0 124064.0 106820.0 125476.0 103905.0 109458.0 98646.4 55224.9 59001.7 93359.1 75808.2 158756.0 136687.0 113244.0 148027.0 121561.0 127244.0 133261.0 119704.0 290.1297087_MZ S-(2-Methylbutanoyl)-dihydrolipoamide Un 1.0 None None None None S-(2-Methylbutanoyl)-dihydrolipoamide-E is an intermediate in isoleucine degradation. S-(2-Methylbutanoyl)-dihydrolipoamide is normally conjugated to a lysine residue of the methylpropanoyltransferase enzyme (E stands for enzyme). The structure shown here is the free form. Specifically S-(2-Methylbutanoyl)-dihydrolipoamide-E is the 2-methylbutanoyl thioester of the reduced lipoyllysine residue in dihydrolipoyllysine-residue (2-methylpropanoyl)transferase. C13H25NO2S2, S-(3-Methylbutanoyl)-dihydrolipoamide-E None None None 5991.4 6043.1 6997.26 8220.48 4922.77 5992.15 5620.55 10492.0 3735.19 5393.34 5791.4 5053.76 3193.98 5480.38 8172.42 6619.15 13578.5 3359.57 4127.39 4483.88 4162.71 3597.75 4698.2 4354.55 4265.16 5350.62 5165.32 3774.0 3670.65 6660.75 4930.36 4856.57 2862.07 3500.0 4165.97 5079.5 3637.15 3315.32 3118.57 5987.89 2663.65 5077.47 293.0098705_MZ D-Glucuronic acid 1-phosphate Un 1.0 None None None None D-Glucuronic acid 1-phosphate is an end product of the UDP-glucuronic acid pathway. Formation of free glucuronic acid from UDP-glucuronic acid can be considered as the first step in the synthesis of vitamin C, a pathway that occurs in most vertebrates, although not in guinea pigs and primates, including humans. Free glucuronic acid can also be converted to pentose phosphate intermediates via the 'pentose pathway'. The latter is interrupted in subjects with pentosuria, who have a deficiency in l-xylulose reductase (EC 1.1.1.10, an enzyme that belongs to the short-chain dehydrogenase/reductase family) and excrete abnormal amounts of l-xylulose. Some xenobiotics stimulate the formation of vitamin C in animals and enhance the excretion of l-xylulose in humans with pentosuria and have shown that aminopyrine, metyrapone and other xenobiotics cause an almost instantaneous increase in the conversion of UDP-glucuronic acid to glucuronic acid. It is usually stated that glucuronic acid formation from UDP-glucuronic acid is the result of two successive reactions comprising the hydrolysis of UDP-glucuronic acid to glucuronic acid 1-phosphate and UMP by nucleotide pyrophosphatase (E-NPP3, EC 3.6.1.9), followed by dephosphorylation of glucuronic acid 1-phosphate. Glucuronidation is responsible for conjugating potentially toxic lipophilic compounds with glucuronic acid, thereby producing molecules with greater aqueous solubility that is excreted more readily into urine and bile. The rate at which any compound may be glucuronidated depends on the concentration and activity of the UDP-glucuronosyltransferases as well as the concentration of the cofactor UDP-glucuronic acid. UDP-glucuronic acid is formed after oxidation of UDP-glucose by UDP-glucose dehydrogenase (UGDH, EC 1.1.1.22) with NAD as the electron acceptor. UDP-glucuronic acid may then be either used as the glucuronic acid donor for xenobiotic conjugation reactions by UDPglucuronosyltransferases (GlcAT-P, EC 2.4.1.17), or degraded to D-glucuronic acid 1-phosphate after the phosphodiester bond is cleaved by E-NPP3. E-NPP3 is the same enzyme that further reduces D-Glucuronic acid 1-phosphate to free D-glucuronic acid. Decreases in UDP-glucuronic acid concentration may be due to reduced availability of UDP-glucose or decreased UGDH activity or to increased activities of GlcAT-P or E-NPP3. Exposure to volatile anesthetics reduces hepatic UDP-glucuronic acid concentrations, and alters the rate of conjugation of compounds such as acetaminophen, bilirubin, diethylstilbestrol, iopanoic acid and valproic acid in a non-sex-dependent fashion in experimental mice. The depletion of UDP-glucuronic acid by anesthetics is caused by altered activity of microsomal E-NPP3. (PMID: 2167093, 16689937, 1276). C6H11O10P None None None 18533.9 19174.5 19221.7 20392.3 18639.8 19618.7 20089.4 19460.3 18971.3 21192.8 21227.3 18896.4 21015.5 21749.9 21383.8 28154.0 20178.9 18999.7 22134.2 17773.8 18593.8 19665.7 16140.9 19224.7 23692.0 17884.8 20144.4 17301.7 15254.8 22916.0 21508.8 28477.6 24193.1 18692.6 19705.9 17403.8 22234.8 21647.2 15741.8 16226.4 21461.4 19032.4 293.2114691_MZ 17-Hydroxylinolenic acid Un 1.0 None None None None 17-hydroxylinolenic acid participates in alpha- Linolenic acid metabolism. 17-hydroxylinolenic acid is produced from alpha linolenic acid. Alpha-Linolenic acid is an organic compound found in many common vegetable oils. Systematically, it is named all-cis-9,12,15-octadecatrienoic acid.[1] In physiological literature, it is given the name 18:3 (n−3). Alpha-linolenic acid is a carboxylic acid with an 18-carbon chain and three cis double bonds. The first double bond is located at the third carbon from the n end. Thus, α-linolenic acid is a polyunsaturated n−3 (omega-3) fatty acid. It is an isomer of γ-linolenic acid, a polyunsaturated n−6 (omega-6) fatty acid.(Wikipedia). C18H30O3, 13-OxoODE, 9-OxoODE, A-12(13)-EpODE, 13-HOTE, 15(16)-EpODE, 9(10)-EpODE, 9-HOTE None None None 23378.1 30163.3 26988.2 57018.4 55934.6 57794.4 44739.9 27235.1 32793.1 37039.8 37491.2 36875.8 12923.9 43958.1 45451.0 42391.1 26314.0 15677.3 28114.7 23038.5 29126.1 23064.0 35308.2 28053.0 35205.4 25356.4 49059.9 29050.1 22331.9 35118.4 29867.4 24648.2 31780.9 27957.9 23468.2 24642.5 20907.6 46591.0 13216.4 34753.9 18365.1 21632.0 294.0505206_MZ 5-Aminoimidazole ribonucleotide Un 1.0 None None None None 5-aminoimidazole ribonucleotide (AIR), is an intermediate of purine nucleotide biosynthesis. It is also the precursor to 4-amino-2-methyl-5-hydroxymethylpyrimidine (HMP), the first product of pyrimidine biosynthesis. This reaction is mediated by the enzyme HMP-P kinase (ThiD). HMP is a precursor of thiamine phosphate (TMP), and subsequently to thiamine pyrophosphate (TPP). TPP is an essential cofactor in all living systems that plays a central role in metabolism. (PMID: 15326535). 5-Aminoimidazole ribonucleotide is a substrate for a number of proteins including: Scaffold attachment factor B2, Multifunctional protein ADE2, Pulmonary surfactant-associated protein B, Tumor necrosis factor receptor superfamily member 25, Pulmonary surfactant-associated protein C, Serine/threonine-protein kinase Chk1, Vinexin, Trifunctional purine biosynthetic protein adenosine-3, Antileukoproteinase 1 and Scaffold attachment factor B. C8H14N3O7P None None None 13317.2 12895.8 13652.0 12166.3 12691.3 12292.9 10495.7 13104.7 9805.79 10095.1 12761.2 12920.1 12506.9 14455.0 11755.3 10871.5 12722.3 10943.3 12410.9 10947.1 14648.6 13195.6 11574.9 12614.9 10876.5 12604.3 10805.6 11994.2 12587.9 12931.6 11675.3 10310.3 11347.4 10023.3 13855.9 12852.7 11390.0 12205.0 9562.21 12125.3 13177.3 12346.9 295.2273297_MZ Alpha-dimorphecolic acid Un 1.0 None None None None Alpha-dimorphecolic acid or 9(S)-HODE is an endogenous fatty acid (PPAR)gamma agonist synthesized in the body from linoleic acid. Alpha-dimorphecolic acid activates peroxisomal proliferator-activated receptor-gamma (PPAR)gamma in human endothelial cells increasing plasminogen activator inhibitor type-1 expression. Plasminogen activator inhibitor type-1 (PAI-1) is a major physiological inhibitor of fibrinolysis, with its plasma levels correlating with the risk for myocardial infarction and venous thrombosis. The regulation of PAI-1 transcription by endothelial cells (ECs), a major source of PAI-1, remains incompletely understood. Adipocytes also produce PAI-1, suggesting possible common regulatory pathways between adipocytes and ECs. Peroxisomal proliferator-activated receptor-gamma (PPAR)gamma is a ligand-activated transcription factor that regulates gene expression in response to various mediators such as 15-deoxy-Delta12, 14-prostaglandin J2 (15d-PGJ2) and oxidized linoleic acid (9- and 13-HODE). Alpha-dimorphecolic acid is a ligand of the G protein-coupled receptor G2A. (PMID: 10073956, 16647253, 16236715). C18H32O3, 13S-hydroxyoctadecadienoic acid, 9,10-Epoxyoctadecenoic acid, 12,13-EpOME, 9-HODE None None None 28660.5 32034.7 31682.1 42233.9 37624.6 55180.1 47138.7 36693.7 31038.6 34189.2 33854.4 27293.6 22548.2 42592.4 40076.8 30289.9 46427.5 28961.6 33618.1 32415.9 32950.6 22899.3 35203.2 33245.1 31363.1 25737.9 34171.9 33300.2 23200.4 37839.5 28361.4 24185.7 24915.8 42128.1 23731.0 35761.3 23085.5 29880.7 21728.1 31908.1 27976.0 34214.4 296.0819301_MZ 5'-Methylthioadenosine Un 1.0 None None None None 5'-Methylthioadenosine (MTA) is a naturally occurring sulfur-containing nucleoside present in all mammalian tissues. It is produced from S-adenosylmethionine mainly through the polyamine biosynthetic pathway, where it behaves as a powerful inhibitory product. MTA is metabolized solely by MTA-phosphorylase, to yield 5-methylthioribose-1-phosphate and adenine, a crucial step in the methionine and purine salvage pathways, respectively. Evidence suggests that MTA can affect cellular processes in many ways. For instance, MTA has been shown to influence regulation of gene expression, proliferation, differentiation and apoptosis (PMID 15313459). 5-Methylthioadenosine can be found in human urine. Elevated excretion appears in children with severe combined immunodeficiency syndrome (PMID 3987052). C11H15N5O3S None None None 14626.5 14366.2 15180.4 11162.3 13103.0 16364.5 16440.4 15399.1 15688.3 10703.5 12199.0 15886.0 12363.9 12908.2 13191.5 15517.5 16020.0 12839.4 11137.3 13668.2 13350.6 13818.9 14666.4 13738.8 13199.5 13365.9 14219.9 13365.1 14124.8 14591.0 13995.9 12164.4 13413.4 12162.5 14702.6 12643.5 14357.6 15458.7 7912.29 12365.7 11564.3 12128.0 296.2626939_MZ Palmitoleoyl Ethanolamide Un 1.0 None None None None C18H35NO2 None None None 5325.68 5588.32 5550.39 5348.58 5848.38 5582.41 6386.01 6659.15 5103.67 5828.99 6362.95 5669.66 5078.95 6155.01 5448.7 5084.03 6543.62 8066.02 4849.29 6255.65 5366.66 4879.53 5368.57 5834.92 5566.57 4892.43 4922.59 6511.96 5153.04 5673.14 5220.26 4647.65 5659.64 5907.36 4742.84 6082.62 4413.11 5441.95 6418.14 5654.65 4805.36 5749.08 297.2428533_MZ 3-Oxooctadecanoic acid Un 1.0 None None None None 3-Oxo-Octadecanoic acid is an intermediate in fatty acid biosynthesis. Specifically, 3-Oxo-Octadecanoic acid is converted from Malonic acid via the enzyme, beta-ketoacyl -acyl-carrier-protein synthase II. (E.C: 2.3.1.179). In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. C18H34O3 None None None 101428.0 100573.0 122783.0 96574.6 103879.0 103006.0 107574.0 164267.0 90059.1 98413.9 105001.0 87430.8 79006.9 108400.0 108542.0 85904.7 211442.0 113406.0 85465.1 124413.0 95167.5 74112.5 96629.8 102064.0 93481.9 80273.1 94256.0 102267.0 76551.4 108393.0 78327.9 77028.1 83638.2 96394.8 75221.4 101837.0 74031.0 82348.8 92567.4 94831.4 68358.0 93610.4 297.2789497_MZ Nonadecanoic acid Un 1.0 None None None None Nonadecanoic acid is an odd-numbered long chain fatty acid, likely derived from bacterial or plant sources. Nonadecanoic acid has been found in ox fats and vegetable oils. It is also used by certain insects as a phermone. C19H38O2, Pristanic acid, Tuberculostearic acid None None None 34364.2 37029.9 33444.8 33555.0 34706.3 31733.9 35712.8 42195.3 31850.5 33271.8 36984.8 33954.9 33198.2 36501.3 30358.5 30493.7 42423.0 50224.3 29587.1 40141.7 32621.6 29156.8 33021.7 34767.5 32817.8 31128.7 31668.3 38913.4 29238.3 37018.5 30324.0 29119.7 33119.4 33950.1 29147.9 35605.6 27185.5 33332.2 33101.2 32589.0 26994.3 31084.2 299.2583926_MZ (R)-3-Hydroxy-Octadecanoic acid Un 1.0 None None None None (R)-3-Hydroxy-Octadecanoic acid is an intermediate in fatty acid biosynthesis. Specifically, (R)-3-Hydroxy-Octadecanoic acid is converted from 3-Oxo-Octadecanoic acid via 3-oxoacyl- [acyl-carrier-protein] reductase. (EC: 1.1.1.100). C18H36O3 None None None 41063.1 40447.0 38497.0 36835.9 36975.6 35832.6 37601.2 47698.0 32587.0 38960.4 41371.9 34909.6 31241.1 43484.7 36177.6 30184.7 57382.3 40811.3 33506.7 39511.6 35725.5 27962.3 38406.5 38591.6 32695.6 29158.0 32678.9 37526.9 27548.1 43667.8 28774.4 28378.2 29886.2 33994.6 27724.0 36446.4 27807.7 30542.0 33613.1 36123.9 26457.9 33673.9 300.0397208_MZ N-Acetylgalactosamine 4-sulphate Un 1.0 None None None None Also known as GalNAc4S, this molecule is a key component of dermatan, keratan and chondroitin sulfate. It is also a substrate for the enzyme N-acteylgalactosamine-4-sulphate transferase. This molecule is found in elevated concentrations in the urine of patients suffering from muchopolysaccharidosis type III, IV and VI. Levels are typically 300-400 times normal values. GalNAc4S is thought to be derived from the action of beta-N-acetylhexosaminidase on sulphated GlcNAc or GalNAc residues at the non-reducing end of keratan sulphate, dermatan sulphate or chondroitin sulphate. C8H15NO9S, N-Acetylglucosamine 6-sulfate, N-Acetylgalactosamine 6-sulfate None None None 78022.4 73069.0 91240.1 80649.2 99273.6 77292.5 81040.3 83897.5 68294.9 67444.2 67637.4 78061.7 92514.1 72251.1 98466.9 47696.2 104876.0 66618.4 100210.0 72935.5 115411.0 82389.4 99697.9 81755.5 78216.8 84814.2 99368.5 75002.0 85000.6 47998.7 65657.4 66041.2 82286.3 81847.4 82165.4 82044.8 84833.9 68420.3 50455.1 98543.6 65489.3 93110.5 301.0945731_MZ 1-Methylinosine Un 1.0 None None None None Modified nucleotide found at position 37 in tRNA 3' to the anticodon of eukaryotic tRNA. Shown that sequences are forced to adopt a hairpin conformation if one of the central 6 nt is replaced by the corresponding methylated nucleotide, such as 1-methylguanosine. In Vivo synthesis: Inosine-37 in tRNA is synthesised by a hydrolytic deamination-type reaction, catalysed by distinct tRNA:adenosine deaminases. C11H14N4O5 None None None 8056.03 7265.88 10214.2 7254.53 8500.91 8930.33 9875.89 12397.3 6154.14 7207.13 7422.06 6207.15 8677.64 7683.75 12836.1 9548.47 15771.9 8387.65 7802.54 12111.9 7139.47 6062.73 7158.28 7788.32 7978.05 6223.81 9122.01 7940.03 6103.16 9406.67 7195.26 7756.34 5306.29 6306.24 6606.21 8345.12 5945.11 6074.92 6764.4 9272.96 7232.32 8048.86 301.1866549_MZ 2-Methoxyestradiol Un 1.0 None None None None 2-Methoxyestradiol (2ME2) is a drug that prevents the formation of new blood vessels that tumors need in order to grow (angiogenesis). It is derived from estrogen, although it binds poorly to known estrogen receptors, and belongs to the family of drugs called angiogenesis inhibitors. It has undergone Phase 1 clinical trials against breast cancers. Preclinical models also suggest that 2ME2 could also be effective against inflammatory diseases such as rheumatoid arthritis. The CAS name for 2ME2 is (17 beta)-2-methoxyestra-1,3,5(10)-triene-3,17-diol. It also acts as a vasodilator. C19H26O3, 2-Hydroxyestradiol-3-methyl ether, 19-Hydroxyandrost-4-ene-3,17-dione, 7a-Hydroxyandrost-4-ene-3,17-dione, 11b-Hydroxyandrost-4-ene-3,17-dione, 16a-Hydroxyandrost-4-ene-3,17-dione, 4-methoxy-17beta-estradiol None None None 5843.02 4571.1 4142.1 4862.14 4086.48 5100.46 4471.15 4942.31 3903.03 4665.22 4652.85 4017.83 2551.53 4903.19 4583.39 4074.14 5814.67 2363.25 3352.29 3480.62 4651.99 3336.52 4581.38 4757.85 3677.67 3454.22 4045.41 3561.23 3428.32 6219.84 3698.42 3529.88 3159.44 3737.08 4095.94 4262.41 3729.59 3559.07 2545.08 4075.22 2809.49 3494.29 301.2167328_MZ Retinyl ester Un 1.0 None None None None Retinyl ester is a substrate for Lecithin retinol acyltransferase and Retinal pigment epithelium-specific 65 kDa protein. C20H30O2, Eicosapentaenoic acid None None None 16518.2 15889.2 15881.8 23137.2 20303.1 20906.5 29087.3 17299.4 24048.1 16422.0 18135.5 16837.0 21001.0 18388.9 17796.9 13681.9 31148.0 29646.4 21798.2 21229.5 16191.1 13647.0 17373.2 15737.2 22872.9 17873.2 17422.0 22815.7 13341.0 20097.6 23904.9 14388.9 16366.3 18161.7 12602.0 26180.8 15665.7 20388.8 16796.8 17494.4 31472.6 20394.1 303.0838623_MZ N-Acetylaspartylglutamic acid Un 1.0 None None None None N-Acetylaspartylglutamate (NAAG) is a neuropeptide found in millimolar concentrations in brain that is localized to subpopulations of glutamatergic, cholinergic, GABAergic, and noradrenergic neuronal systems. NAAG is released upon depolarization by a Ca(2+)-dependent process and is an agonist at mGluR3 receptors and an antagonist at NMDA receptors. NAAG is catabolized to N-acetylaspartate and glutamate primarily by glutamate carboxypeptidase II, which is expressed on the extracellular surface of astrocytes. The levels of NAAG and the activity of carboxypeptidase II are altered in a regionally specific fashion in several neuropsychiatric disorders. (PMID 9361299). N-Acetylaspartylglutamic acid (NAAG) is a purported precursor of N-Acetylaspartic acid (NAA) and is present at about one-tenth of the concentration of NAA in the brain. NAAG has been reported to activate N-methyl- D-aspartic acid (NMDA) receptors in neurons. Previous immunohistochemical studies in the vertebrate central nervous system (CNS) have suggested that NAAG is exclusively localized to neurons. Recent evidence, however, indicates that NAAG might also be localized to nonneuronal cells within the CNS. Only traces of NAA and NAAG are detectable in other tissues. Some compounds can change levels of NAA and NAAG in the brain. For example, methylphenidante increases the levels of NAA and NAAG in the cerebral cortex; amphetamine also increases NAA concentration in a mature brain by 26%, raising the possibility that other neurochemical systems might be involved in the clinical effects of stimulants. (PMID: 10603234). C11H16N2O8 None None None 8484.55 8293.44 8248.22 10904.7 8192.79 10406.8 8740.65 8971.53 7347.03 10012.3 8924.45 8230.72 6308.61 8486.22 11682.0 12885.4 8048.25 7131.34 8350.4 6990.18 8515.83 6862.39 9038.74 8382.37 10771.9 7569.22 10094.5 7781.87 7318.84 11431.3 8374.56 16062.3 5378.34 6243.57 10819.5 8662.25 6859.74 6420.7 8349.13 8569.09 6941.97 8400.51 303.2325397_MZ Arachidonic acid Un 1.0 None None None None Arachidonic acid is a polyunsaturated, essential fatty acid. It is found in animal and human fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides. It is formed by the synthesis from dietary linoleic acid. Arachidonic acid mediates inflammation and the functioning of several organs and systems either directly or upon its conversion into eicosanoids. Arachidonic acid in cell membrane phospholipids is the substrate for the synthesis of a range of biologically active compounds (eicosanoids) including prostaglandins, thromboxanes, and leukotrienes. These compounds can act as mediators in their own right and can also act as regulators of other processes, such as platelet aggregation, blood clotting, smooth muscle contraction, leukocyte chemotaxis, inflammatory cytokine production, and immune function. Arachidonic acid can be metabolized by cytochrome p450 (CYP450) enzymes to 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acids (EETs), their corresponding dihydroxyeicosa-trienoic acids (DHETs), and 20-hydroxyeicosatetraenoic acid (20-HETE). The production of kidney CYP450 arachidonic acid metabolites is altered in diabetes, pregnancy, hepatorenal syndrome, and in various models of hypertension, and it is likely that changes in this system contribute to the abnormalities in renal function that are associated with many of these conditions. Phospholipase A2 (PLA2) catalyzes the hydrolysis of the sn-2 position of membrane glycerophospholipids to liberate arachidonic acid (PMID: 12736897, 12736897, 12700820, 12570747, 12432908). C20H32O2, Cis-8,11,14,17-Eicosatetraenoic acid, Mesterolone None None None 277504.0 239678.0 318579.0 325891.0 375770.0 429890.0 540748.0 423205.0 379212.0 210968.0 278392.0 321856.0 462648.0 379128.0 310413.0 204160.0 635562.0 587229.0 277678.0 546249.0 247501.0 217555.0 365039.0 260045.0 368014.0 234931.0 198299.0 380198.0 201090.0 372848.0 515550.0 243872.0 275628.0 255711.0 143732.0 475229.0 234236.0 438728.0 291820.0 290099.0 645435.0 294829.0 305.0448170_MZ Luteolin Un 1.0 None None None None Luteolin is a naturally occurring flavonoid. (PMID: 17168665). The flavonoids are polyphenolic compounds found as integral components of the human diet. They are universally present as constituents of flowering plants, particularly of food plants. The flavonoids are phenyl substituted chromones (benzopyran derivatives) consisting of a 15-carbon basic skeleton (C6-C3-C6), composed of a chroman (C6-C3) nucleus (the benzo ring A and the heterocyclic ring C), also shared by the tocopherols, with a phenyl (the aromatic ring B) substitution usually at the 2-position. Different substitutions can typically occur in the rings, A and B. Several plants and spices containing flavonoid derivatives have found application as disease preventive and therapeutic agents in traditional medicine in Asia for thousands of years. The selection of a particular food plant, plant tissue or herb for its potential health benefits appears to mirror its flavonoid composition. The much lower risk of colon, prostate and breast cancers in Asians, who consume more vegetables, fruits and tea than populations in the Western hemisphere do, raises the question of whether flavonoid components mediate the protective effects of diets rich in these foodstuffs by acting as natural chemopreventive and anticancer agents. An impressive body of information exists on the antitumoral action of plant flavonoids. In vitro work has concentrated on the direct and indirect actions of flavonoids on tumor cells, and has found a variety of anticancer effects such as cell growth and kinase activity inhibition, apoptosis induction, suppression of the secretion of matrix metalloproteinases and of tumor invasive behavior. Furthermore, some studies have reported the impairment of in vivo angiogenesis by dietary flavonoids. Experimental animal studies indicate that certain dietary flavonoids possess antitumoral activity. The hydroxylation pattern of the B ring of the flavones and flavonols, such as luteolin seems to critically influence their activities, especially the inhibition of protein kinase activity and antiproliferation. The different mechanisms underlying the potential anticancer action of plant flavonoids await further elucidation. Certain dietary flavonols and flavones targeting cell surface signal transduction enzymes, such as protein tyrosine and focal adhesion kinases, and the processes of angiogenesis appear to be promising candidates as anticancer agents. Further in vivo studies of these bioactive constituents is deemed necessary in order to develop flavonoid-based anticancer strategies. In view of the increasing interest in the association between dietary flavonoids and cancer initiation and progression, this important field is likely to witness expanded effort and to attract and stimulate further vigorous investigations. (PMID: 16097445). C15H10O6, Kaempferol None None None 262285.0 144310.0 87061.9 54102.0 70640.3 231062.0 94827.3 82444.7 39084.2 227472.0 229852.0 30558.0 48166.7 165066.0 64803.8 87500.0 43367.9 108505.0 69894.6 74096.5 212133.0 22274.8 131679.0 99836.7 125594.0 49705.7 113764.0 62651.6 50056.6 223126.0 90283.7 74206.2 33963.6 76549.4 34356.7 141641.0 42778.2 33839.1 47735.5 121201.0 80952.9 93581.5 305.2126137_MZ 5-Androstene-3b,16b,17a-triol Un 1.0 None None None None 5-Androstene-3b,16b,17a-triol is an steroid found in the urine of human pregnancy (PMID 4452739), in the urine of newborns and infants (PMID 5126818), and in the mono- and disulfate fractions of human bile. (PMID 5410667). C19H30O3, 5-Androstene-3b,16a,17a-triol, 5-Androstenetriol, 11-Hydroxyandrosterone, 16-alpha-Hydroxyandrosterone, 5-Androstene-3alpha-16b,17b-triol None None None 22989.2 19964.3 17649.7 19650.6 22098.1 26026.2 44733.7 29726.1 12785.5 21638.4 21190.0 7904.07 30036.1 18669.9 19684.5 20131.9 38318.0 33612.6 23866.1 31387.2 16373.1 6397.56 21819.3 20638.1 19980.6 8270.24 21123.2 21175.0 7359.83 20709.1 26576.0 16600.5 7124.24 20591.3 9264.54 17801.4 12108.3 9058.03 16797.1 20961.4 36002.4 21158.3 305.2479220_MZ 8,11,14-Eicosatrienoic acid Un 1.0 None None None None 8,11,14-Eicosatrienoic acid is a 20-carbon-chain omega-6 fatty acid, unsaturated at positions 8, 11, and 14. It differs from arachidonic acid (5,8,11,14-eicosatetraenoic acid) only at position 5. 8,11,14-Eicosatrienoic acid is also known as Dihomo-gamma-linolenic acid (DGLA). In physiological literature, it is given the name 20:3(n-6). DGLA is the elongation product of the 18 carbon gamma-linolenic acid (GLA). DGLA can be converted into prostaglandin E1 (PGE1). PGE1 inhibits platelet aggregation and also exerts a vasodilatory effect. DGLA competes with arachadonic acid for COX and lipoxygenase, inhibiting the production of arachadonic acid's eicosanoids. C20H34O2, 5,8,11-Eicosatrienoic acid None None None 43905.1 27316.8 30794.5 27452.8 47421.7 29679.5 73489.9 50899.0 40802.6 29882.5 29968.1 31312.8 61402.9 61640.3 46941.3 28162.4 50638.6 98248.3 33939.8 91653.4 29744.7 25781.9 32627.5 38099.4 49805.8 30172.7 29510.5 58316.3 31646.2 37327.0 52964.7 24623.9 50193.7 30722.9 19312.9 64812.5 34782.7 46865.3 42109.8 31185.0 119346.0 61087.9 306.0767338_MZ Glutathione Un 1.0 None None None None Glutathione is a compound synthesized from cysteine, perhaps the most important member of the body's toxic waste disposal team. Like cysteine, glutathione contains the crucial thiol (-SH) group that makes it an effective antioxidant. There are virtually no living organisms on this planet-animal or plant whose cells don't contain some glutathione. Scientists have speculated that glutathione was essential to the very development of life on earth. glutathione has many roles; in none does it act alone. It is a coenzyme in various enzymatic reactions. The most important of these are redox reactions, in which the thiol grouping on the cysteine portion of cell membranes protects against peroxidation; and conjugation reactions, in which glutathione (especially in the liver) binds with toxic chemicals in order to detoxify them. glutathione is also important in red and white blood cell formation and throughout the immune system. glutathione's clinical uses include the prevention of oxygen toxicity in hyperbaric oxygen therapy, treatment of lead and other heavy metal poisoning, lowering of the toxicity of chemotherapy and radiation in cancer treatments, and reversal of cataracts. (http://www.dcnutrition.com/AminoAcids/) glutathione participates in leukotriene synthesis and is a cofactor for the enzyme glutathione peroxidase. It is also important as a hydrophilic molecule that is added to lipophilic toxins and waste in the liver during biotransformation before they can become part of the bile. glutathione is also needed for the detoxification of methylglyoxal, a toxin produced as a by-product of metabolism. This detoxification reaction is carried out by the glyoxalase system. Glyoxalase I (EC 4.4.1.5) catalyzes the conversion of methylglyoxal and reduced glutathione to S-D-Lactoyl-glutathione. Glyoxalase II (EC 3.1.2.6) catalyzes the hydrolysis of S-D-Lactoyl-glutathione to glutathione and D-lactate. GSH is known as a substrate in both conjugation reactions and reduction reactions, catalyzed by glutathione S-transferase enzymes in cytosol, microsomes, and mitochondria. However, it is also capable of participating in non-enzymatic conjugation with some chemicals, as in the case of n-acetyl-p-benzoquinone imine (NAPQI), the reactive cytochrome P450-reactive metabolite formed by acetaminophen, that becomes toxic when GSH is depleted by an overdose (of acetaminophen). glutathione in this capacity binds to NAPQI as a suicide substrate and in the process detoxifies it, taking the place of cellular protein thiol groups which would otherwise be covalently modified; when all GSH has been spent, NAPQI begins to react with the cellular proteins, killing the cells in the process. The preferred treatment for an overdose of this painkiller is the administration (usually in atomized form) of N-acetylcysteine, which is used by cells to replace spent GSSG and renew the usable GSH pool. (http://en.wikipedia.org/wiki/glutathione). C10H17N3O6S None None None 10148800.0 6752320.0 5268480.0 2592580.0 5279120.0 8400920.0 9173980.0 6740010.0 2015130.0 3434420.0 3758420.0 716714.0 14176800.0 3376070.0 2956230.0 12706000.0 4461490.0 13689800.0 6710450.0 10229900.0 9343880.0 478836.0 5815220.0 6450600.0 7583100.0 2789600.0 7757110.0 6611670.0 2727300.0 4138080.0 9851900.0 7127420.0 2130200.0 4201400.0 1469760.0 5993880.0 3190160.0 955165.0 3546430.0 4783850.0 11762200.0 9573820.0 307.0008112_MZ (S)-5-Diphosphomevalonic acid Un 1.0 None None None None 5-pyrophosphomevalonate is a metabolic intermediate in the mevalonate pathway, catalyzed by the enzyme phosphomevalonate kinase from 5-phosphomevalonate. (wikipedia). C6H14O10P2, (R)-Mevalonic acid-5-pyrophosphate None None None 6124.68 5527.89 6271.37 5203.76 5745.23 6094.54 5332.55 6412.02 5715.13 5459.74 6111.16 7364.32 5919.99 5646.76 5634.56 5894.17 4832.89 6742.54 6612.17 5676.66 6082.36 6614.6 5384.03 6322.01 5157.17 6890.17 5448.17 6376.43 6494.45 5637.04 5165.51 5084.45 6567.44 5547.86 6883.26 6724.72 5886.85 5695.76 5637.26 5897.28 5561.95 6359.66 307.2639191_MZ Eicosadienoic acid Un 1.0 None None None None Eicosadienoic acid is an omega 6 fatty acid found in human milk (PMID: 15256803). Omega-6 fatty acids) are a family of unsaturated fatty acids which have in common a carbon-carbon double bond in the n−6 position; that is, the sixth bond from the end of the fatty acid. The biological effects of the omega−6 fatty acids are largely mediated by their conversion to n-6 eicosanoids that bind to diverse receptors found in every tissue of the body. C20H36O2 None None None 15116.3 13163.5 13877.3 11643.4 18410.8 11015.6 24410.8 24115.9 14795.8 15614.4 12477.6 14775.4 21807.2 34036.4 22029.7 10972.8 17342.4 34218.1 14666.9 34081.1 12733.3 9951.91 12781.8 16190.1 18559.2 12961.0 12427.0 25941.5 12040.2 14938.5 17784.7 8943.54 25960.0 13922.9 8671.46 23500.5 15582.7 15708.0 18308.5 13239.1 29000.8 29202.4 309.0777575_MZ Catechin Un 1.0 None None None None Catechin is an antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms. -- Pubchem. C15H14O6, Epicatechin None None None 58059.5 38415.4 33971.3 24429.6 32671.7 51722.6 49703.1 39043.8 17476.9 25111.0 25407.3 12471.6 77503.8 24511.1 22772.2 74541.5 29710.6 73398.3 37428.8 56166.7 56131.2 9187.62 36417.8 37667.5 44380.5 19581.9 44202.4 39677.5 21020.5 33852.2 55750.6 41901.3 16301.8 25972.9 17046.6 38523.7 23604.4 13055.1 22475.2 29632.1 61040.7 50749.2 309.1179448_MZ Pentaporphyrin I Un 1.0 None None None None Pentaporphyrin I is a porphyrin intermediate detected in liver, kidney and erythrocytes (PubMed ID 8803328 ). C20H14N4 None None None 10557.7 8622.58 8056.18 8379.95 7782.51 11991.2 9343.75 7834.41 6572.49 7826.65 7246.03 7406.83 5419.56 8073.45 7944.78 11578.3 9146.13 6227.47 6094.53 6210.32 9046.03 5385.02 10580.7 7310.0 7814.99 5469.82 7854.7 7480.86 5916.52 11434.9 7463.09 6942.24 5519.34 5721.61 8674.84 8136.62 6909.22 6488.79 5055.04 6957.99 5448.68 6042.74 309.2223859_MZ Androsterone Un 1.0 None None None None Androsterone is an inactive breakdown metabolite of testosterone, the product of a reaction mediated by the enzyme oxidative 17beta-hydroxysteroid dehydrogenase (EC 1.1.1.51, 17beta-HSD). Androsterone is also can be metabolized from other adrenal androgens such as dehydroepiandrosterone, dihydrotestosterone or androstenedione, and is considered an inactive end product; however, it can be a physiological effector in its own right. Androsterone might be converted back to dihydrotestosterone. Humans (and other primates) are unique among mammals in having high levels of circulating androsterone glucuronide, a process that is the major role uridine-diphospho-glucuronosyltransferase (EC 2.4.1.17, UGT) enzymes for glucuronidation of steroid metabolism in humans. Conjugation of androsterone is a pathway found in all vertebrates and is widely recognized that the liver is a major site of glucuronidation; however it is now clear that extrahepatic tissues are also involved in the conjugation of compounds to which these tissues are exposed. High levels of androsterone glucuronide found in the human prostate, breast cyst fluid and ovary follicular fluid suggest that glucuronidation of 5alpha-reduced C19 steroids occurs in these tissues as well. In doping control, the ratio of androsterone/etiocholanone provides valuable information that allows the assignment of a urine specimen to a particular person or the identification of urine samples with identical steroid profiles; this is particularly important to detect attempts of urine manipulation including urine alteration and substitution. (PMID: 9188497, 17017935, 14643063, 12943709, 9699884, 17260133). C19H30O2, Epiandrosterone, Etiocholanolone, Epietiocholanolone, Dihydrotestosterone, Androst-5-ene-3b,17b-diol, 4-Androstenediol, 5b-Dihydrotestosterone None None None 35474.4 12836.1 14895.5 14120.8 24450.1 16291.4 34182.8 52238.1 15868.3 13964.1 21959.9 13271.3 60556.3 23223.9 12061.2 11222.6 15030.3 145097.0 11331.2 37890.7 12582.1 8382.75 16733.2 32934.7 18663.7 13082.8 10713.6 43887.9 14628.9 14946.4 18988.4 13016.9 22988.3 12551.0 8800.56 26750.7 16087.9 17111.4 25639.5 20872.8 54015.2 42107.6 309.2793365_MZ Eicosenoic acid Un 1.0 None None None None Eicosenoic acid is an monounsaturated omega-9 fatty acid found in a variety of plant oils. It is also found in the red cell membrane with increased concentrations in children with regressive autism (16581239). C20H38O2 None None None 29928.2 18250.5 23215.0 20602.9 39869.5 53407.4 41527.8 40588.5 23627.4 25804.4 24095.6 21976.7 64534.9 73421.8 44442.9 17549.3 19448.6 80262.4 23311.8 57388.6 23888.6 19879.9 22297.1 35600.1 38885.9 26553.8 23170.0 48043.4 25964.5 22345.6 24571.6 14949.1 51226.4 24303.8 17591.1 49182.0 29506.3 22802.3 37048.1 24076.9 76936.6 61753.0 310.0307626_MZ Parathion Un 1.0 None None None None Parathion is a highly toxic cholinesterase inhibitor that is used as an acaricide and as an insecticide. C10H14NO5PS None None None 20745.4 17616.0 40134.5 29902.1 30487.1 16556.4 39986.6 25522.4 42021.5 15798.6 27228.7 37050.9 34230.0 16888.4 33432.4 15402.6 22723.6 22515.1 25751.5 27833.8 23602.2 42079.3 16908.1 20318.9 22502.3 42764.0 23632.4 28363.8 30177.1 15100.2 22914.9 14908.8 30022.3 28728.9 27520.3 23984.6 28496.5 33953.2 24089.7 29440.2 33910.0 36001.7 310.0745752_MZ Hawkinsin Un 1.0 None None None None Hawkinsin is a sulfur amino acid identified as (2-l-cystein-S-yl, 4-dihydroxycyclohex-5-en-1-yl)acetic acid. Patients with hawkinsinuria excrete this metabolite in their urine throughout their life, although symptoms of metabolic acidosis and tyrosinemia improve in the first year of life. Alterations in the structure and activity of 4-hydroxyphenylpyruvic acid dioxygenase are causally related to two different metabolic disorders, tyrosinemia type III and hawkinsinuria. (PMID 11073718). C11H17NO6S None None None 14330.2 11229.5 10492.7 8138.7 9143.65 13505.8 12603.1 10776.1 6494.54 7764.56 8645.28 6374.49 15806.9 7598.78 7911.74 16758.4 8474.67 17259.0 10005.5 13474.3 13047.9 5302.66 9627.43 10401.3 10698.9 7362.66 11834.9 10608.3 7740.15 9592.74 13654.4 11239.5 6784.14 8366.27 6860.45 10821.0 7599.61 6142.75 6306.3 8752.2 14125.2 12294.3 311.0120824_MZ Gamma-Glutamyl-Se-methylselenocysteine Un 1.0 None None None None gamma-Glutamyl-Se-methylselenocysteine is an intermediate in selenoamino acid metabolism(KEGG ID C05695). It is generated from Se-methyl-selenocysteine via the enzyme gamma-glutamyltranspeptidase [EC:2.3.2.2]. C9H16N2O5Se None None None 7255.12 7941.41 9129.02 5068.55 8720.83 6297.89 7143.95 8382.22 7503.31 6478.99 8111.83 8865.64 7427.09 8116.38 8342.63 5530.65 7576.3 6789.37 8032.14 6348.72 8472.86 8941.65 6995.39 8071.93 7241.96 8373.7 7537.54 7381.63 8894.28 6187.26 6827.44 5742.65 7899.69 5796.05 10128.3 6897.1 7911.5 9440.05 6666.0 8241.42 8595.82 7433.91 311.2221503_MZ 13-L-Hydroperoxylinoleic acid Un 1.0 None None None None 13-L-Hydroperoxylinoleic acid (13(S)-HPODE) is one of the primary products of the major polyunsaturated fatty acids (linoleic acid and arachidonic acid) from the 15-1ipoxygenase pathway (EC: 1.13.11.31). 13(S)-HPODE is a rather unstable metabolite and is rapidly metabolized to more stable secondary products such as diverse forms of hydroxy fatty acids (via reduction of the hydroperoxy group), alkoxy radicals (via homolytic cleavage of the peroxy group), forms of dihydro(pero)xy fatty acids (via lipoxygenase-catalysed double and triple oxygenation), or epoxy leukotrienes (via a hydrogen abstraction from a doubly allylic methylene group and a homolytic cleavage of the hydroperoxy group). (PMID 9082450). C18H32O4, 8(R)-Hydroperoxylinoleic acid, 9(S)-HPODE, 12,13-DiHODE, 15,16-DiHODE, 9,10-DiHODE None None None 25749.2 24184.0 29345.3 28424.5 28971.8 35851.0 34134.1 37663.6 20302.5 24242.3 25223.4 16583.6 16683.4 29378.3 33112.0 26162.2 50241.6 20161.9 22673.2 27221.1 24231.8 14680.7 25204.6 26838.1 24507.1 16710.7 28832.1 21484.0 14101.5 30867.0 21223.2 19272.3 15095.5 23782.5 15981.0 25841.0 14975.1 17770.2 17715.2 25274.3 18424.0 22998.0 313.0451047_MZ 5'-Phosphoribosyl-N-formylglycinamide Un 1.0 None None None None 5'-Phosphoribosyl-N-formylglycineamide (also known as FGAR or N-Formyl-GAR) is a substrate for Phosphoribosylformylglycinamidine synthase. It is involved in aminoimidazole ribonucleotide biosynthesis and plays a vital role in purine metabolism as well as the conversion of glutamine to glutamate. 5'-Phosphoribosyl-N-formylglycineamide is described as a glycinamide ribonucleotide having a phosphate group at the 5-position and a formyl group on the glycine nitrogen. C8H15N2O9P None None None 5757.2 5038.06 5469.37 5099.94 4845.08 7629.87 4877.75 5040.42 4692.78 5111.78 4981.5 5343.74 4145.68 5255.43 5449.07 7878.79 4449.11 4810.65 4881.0 5383.79 5063.8 5649.13 4944.63 5300.69 4781.88 5347.99 5090.59 5168.15 5257.31 6459.06 5269.38 6814.63 4715.95 4222.29 6248.79 5289.27 4380.07 5064.95 3447.84 5238.2 4914.86 4586.86 313.2378371_MZ 12_13-DHOME Un 1.0 None None None None 12,13-DHOME is the epoxide hydrolase metabolite of the leukotoxin12,13-EpOME. 12,13-EpOMEs act as a protoxin, with the corresponding epoxide hydrolase 12,13-DiHOME specifically exerting toxicity. Both the EpOME and the DiHOME are shown to have neutrophil chemotactic activity. 12,13-DiHOME suppress the neutrophil respiratory burst by a mechanism distinct from that of respiratory burst inhibitors such as cyclosporin H or lipoxin A4,which inhibit multiple aspects of neutrophil activation. 12,13-DHOME is a derivative of linoleic acid diol that have been reported to be toxic in human's tissue preparations. 12,13-DHOME is a naturally occurring proliferator-activated receptor (PPAR) gamma2 ligand, which stimulates adipocytes and inhibits osteoblast differentiation. (PMID: 17435320, 12021203, 12127265). C18H34O4, 9_10-DHOME None None None 24099.1 24306.7 26925.6 23426.6 25973.1 25388.1 24951.3 35301.1 18289.8 21431.8 23631.1 18407.8 12995.2 26433.5 27865.7 24689.2 51024.1 17000.4 19508.5 23609.2 21566.1 13521.4 22707.4 22113.0 21585.8 15556.4 25521.1 20939.0 12935.9 26321.5 17471.4 17130.7 14533.1 20475.4 14527.3 21250.3 14434.8 14318.8 15497.0 22120.0 14545.6 19373.1 315.2533388_MZ Monoacylglyceride(0:0/15:0/0:0) Un 1.0 None None None None MG(0:0/15:0/0:0) is a monoacylglyceride. A monoglyceride, more correctly known as a monoacylglycerol, is a glyceride consisting of one fatty acid chain covalently bonded to a glycerol molecule through an ester linkage. Monoacylglycerol can be broadly divided into two groups; 1-monoacylglycerols (or 3-monoacylglycerols) and 2-monoacylglycerols, depending on the position of the ester bond on the glycerol moiety. Normally the 1-/3-isomers are not distinguished from each other and are termed 'alpha-monoacylglycerols', while the 2-isomers are beta-monoacylglycerols. Monoacylglycerols are formed biochemically via release of a fatty acid from diacylglycerol by diacylglycerol lipase or hormone sensitive lipase. Monoacylglycerols are broken down by monoacylglycerol lipase. They tend to be minor components only of most plant and animal tissues, and indeed would not be expected to accumulate because their strong detergent properties would have a disruptive effect on membranes. 2-Monoacylglycerols are a major end product of the intestinal digestion of dietary fats in animals via the enzyme pancreatic lipase. They are taken up directly by the intestinal cells and converted to triacylglycerols via the monoacylglycerol pathway before being transported in lymph to the liver. Mono- and Diglycerides are commonly added to commercial food products in small quantities. They act as emulsifiers, helping to mix ingredients such as oil and water that would not otherwise blend well. C18H36O4, Monoacylglyceride(15:0/0:0/0:0) None None None 17476.1 15953.8 7206.34 16340.1 7694.73 10873.3 7491.49 8871.12 11751.1 10700.8 9990.44 5358.71 4902.01 15097.3 8275.52 6598.29 10750.3 6450.21 9478.58 6660.75 14806.8 5233.98 10695.1 17536.9 9445.54 5144.79 7411.8 6502.86 4766.91 18382.8 5506.66 7478.94 5398.58 10685.8 5450.15 16423.9 8709.98 4720.16 6228.8 14897.0 5952.6 11712.1 317.0580974_MZ Melanin Un 1.0 None None None None Dermal melanin is produced by melanocytes, which are found in the stratum basale of the epidermis. Although human beings generally possess a similar concentration of melanocytes in their skin, the melanocytes in some individuals and races more frequently or less frequently express the melanin-producing genes, thereby conferring a greater or lesser concentration of skin melanin. Some individual animals and humans have no or very little melanin in their bodies, which is a condition known as albinism. Higher eumelanin levels also can be a disadvantage, however, beyond a higher disposition toward vitamin D deficiency. Dark skin is a complicating factor in the laser removal of port-wine stains. Effective in treating fair skin, lasers generally are less successful in removing port-wine stains in Asians and people of African descent. Higher concentrations of melanin in darker-skinned individuals simply diffuse and absorb the laser radiation, inhibiting light absorption by the targeted tissue. Melanin similarly can complicate laser treatment of other dermatological conditions in people with darker skin. Under the microscope melanin is brown, non-refractile and finely granular with individual granules having a diameter of less than 800 nanometers. This differentiates melanin from common blood breakdown pigments which are larger, chunky and refractile and range in color from green to yellow or red-brown. In heavily pigmented lesions, dense aggregates of melanin can obscure histologic detail. A dilute solution of potassium permanganate is an effective melanin bleach. Pigments causing darkness in skin, hair, feathers, etc. They are irregular polymeric structures and are divided into three groups: allomelanins in the plant kingdom and eumelanins and phaeomelanins in the animal kingdom. Because melanin is an aggregate of smaller component molecules, there are a number of different types of melanin with differing proportions and bonding patterns of these component molecules. Both pheomelanin and eumelanin are found in human skin and hair, but eumelanin is the most abundant melanin in humans, as well as the form most likely to be deficient in albinism. Freckles and moles are formed where there is a localized concentration of melanin in the skin. They are highly associated with pale skin. Melanin is a biopolymer and a neuropeptide. In the early 1970s, John McGinness, Peter Corry, and Peter Proctor reported that melanin is a high-conductivity organic semiconductor (Science, vol 183, 853-855 (1974)). Studies revealed that melanin acted as a voltage-controlled solid-state threshold switch. Further, it emitting a flash of light electroluminescence when it switched. C18H10N2O4 None None None 67550.5 70245.7 66805.5 50067.9 39595.5 69482.8 45767.2 57418.4 43141.9 52586.8 46822.5 67261.5 31157.4 73533.7 47449.4 60378.3 44507.0 38395.1 43985.6 43142.1 56217.1 63909.8 37923.1 66391.6 39469.3 65966.6 49517.0 53049.0 71548.7 66628.6 69083.2 58164.7 62623.0 49428.0 82952.0 56060.9 63381.2 65216.3 50714.6 42780.0 52107.1 44199.2 317.1750355_MZ Ubiquinone Q2 Un 1.0 None None None None Ubiquinone-2 is a member of the chemical class known as Polyprenylbenzoquinones. These are compounds containing a polyisoprene chain attached to a quinone at the second ring position. Ubiquione-2 has just 2 isoprene units. Normally in humans it has 10. Ubiquinone-2 is an intermediate in the synthesis of Ubiquionone 10. Ubiquionone is involved in cellular respiration. It is fat-soluble and is therefore mobile in cellular membranes; it plays a unique role in the electron transport chain (ETC). In the inner bacterial membrane, electrons from NADH and succinate pass through the ETC to the oxygen, which is then reduced to water. The transfer of electrons through ETC results in the pumping of H+ across the membrane creating a proton gradient across the membrane, which is used by ATP synthase (located on the membrane) to generate ATP. C19H26O4 None None None 14637.1 15678.5 10446.9 7363.38 6395.77 11817.8 6974.94 7573.06 5328.98 6019.19 9715.03 7571.39 6241.39 7935.32 6940.27 10633.9 10764.4 11481.7 5084.55 11453.6 5606.53 4769.93 6082.38 5694.62 6458.36 5307.24 9401.56 6467.96 5762.02 11882.4 6521.89 5075.56 5504.52 5533.49 6156.04 5753.21 5083.91 4787.49 3422.47 6218.23 10778.5 5432.25 317.2114055_MZ 5-HEPE Un 1.0 None None None None 5-HEPE is a major eicosanoid formed from eicosapentaenoic acid (EPA). 5-HEPE is produced in human neutrophils. The eicosanoids are a diverse family of molecules that have powerful effects on cell function. They are best known as intercellular messengers, having autocrine and paracrine effects following their secretion from the cells that synthesize them. The diversity of possible products that can be synthesized from eicosatrienoic acid is due, in part to the variety of enzymes that can act on it. Studies have placed many, but not all, of these enzymes at or inside the nucleus. In some cases, the nuclear import or export of eicosatrienoic acid-processing enzymes is highly regulated. Furthermore, nuclear receptors that are activated by specific eicosanoids are known to exist. (PMID: 8847485, 15896193). C20H30O3, Leukotriene A4, 12-HEPE, 14,15-EpETE, 15-HEPE, 15-KETE, 17,18-EpETE, 5-KETE, 12-KETE None None None 9557.46 14449.9 14209.1 19576.4 27616.5 24292.8 18151.1 11618.0 17906.2 14076.8 20558.7 18563.9 5723.46 19087.6 18595.7 18388.3 12307.5 7160.8 12654.7 11546.8 14900.0 13673.7 18564.5 12074.5 19306.2 14239.8 16600.4 12857.1 11396.5 17366.8 17011.2 13130.1 17902.5 10215.9 11724.9 14180.2 11271.3 25065.7 6491.41 15644.7 9504.68 9461.06 317.2473804_MZ Allopregnanolone Un 1.0 None None None None Allopregnanolone is a neuroactive metabolite of progesterone and a barbiturate-like modulator of central gamma-aminobutyric acid receptors that modify a range of behaviors, including the stress response. is a steroid created in the body when progesterone, the female sex hormone, is metabolized. Typically, THP (allopregnanolone) is released in the brain in response to stress, and quiets the neural system within 30 minutes of escalation. This steroid hormone has recently been found to be responsible for the extreme mood swings found in teenagers. In adults and pre-pubescent chlidren THP normally helps soothe the activity of brain cells by binding to GABA receptors that inhibit accelerating electrical activity. However, in pubescent teenagers THP actually becomes a GABA receptor antagonist. GABA (gamma-aminobutyric acid) is the primary inhibitory neurotransmitter in the brain with most sedatives (tranquilizers, anesthetics and alcohol) acting on the GABA receptor. C21H34O2, Alloepipregnanolone, 3a-Hydroxy-5b-pregnane-20-one, Epimetendiol, Epipregnanolone None None None 2727.65 2983.96 2589.67 2752.42 3220.44 2689.78 3140.21 3180.7 2895.55 3064.39 3175.05 3074.79 2761.66 3045.69 3241.73 2811.61 2955.31 3820.51 2439.13 3312.75 2483.26 2277.11 2794.21 3116.92 2999.5 2490.88 2829.47 3726.09 2344.21 3022.95 2882.27 2704.76 3051.16 2906.71 2416.96 2738.24 2160.18 2923.09 2465.15 2788.73 2496.41 2889.78 319.2274040_MZ 5,6-Epoxy-8,11,14-eicosatrienoic acid Un 1.0 None None None None 5,6-Epoxy-8,11,14-eicosatrienoic acid is an Epoxyeicosatrienoic acid (EET), a metabolite of arachidonic acid. The epoxyeicosatrienoic acids (EETs) are endogenous lipid mediators produced by P450 epoxygenases and metabolized through multiple pathways including soluble epoxide hydrolase (sEH). The cytochrome P-450 (P450) monooxygenase pathway includes enzymes of the CYP1A, CYP2B, CYP2C, CYP2E, and CYP2J subfamilies that catalyze the formation of four regioisomeric products, 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid. EETs are produced in brain and perform important biological functions, including protection from ischemic injury. Both light flashes and direct glial stimulation produce vasodilatation mediated by EETs. EETs may be involved in the development of hypertension and endothelial dysfunction in DOCA-salt rats, but not in excessive collagen deposition or electrophysiological abnormalities. EETs have vasodilator and natriuretic effect. Blockade of EET formation is associated with salt-sensitive hypertension. (PMID: 17494091, 17468203, 17434916, 17406062, 17361113). C20H32O3, 8,9-Epoxyeicosatrienoic acid, 14R,15S-EpETrE, Hydroxyeicosatetraenoic acid, 15(S)-HETE, 14,15-Epoxy-5,8,11-eicosatrienoic acid, 11,12-Epoxyeicosatrienoic acid, 8-HETE, 16(R)-HETE, 11(R)-HETE, 20-Hydroxyeicosatetraenoic acid, 12-HETE, 18-Hydroxyarachidonic acid, 9-HETE, 11,12-EpETrE, 5-HETE, 19(S)-HETE None None None 11790.4 11959.5 12151.5 15202.1 15849.7 19026.4 18220.5 14089.5 17548.1 13294.5 14556.9 12591.1 11507.8 15752.4 14317.4 12996.6 15736.7 14498.9 11315.8 14073.4 12181.9 9385.18 14621.4 12048.1 13873.9 10508.7 12088.6 12990.7 9578.44 15551.0 13419.1 11459.5 12751.9 10520.6 10212.7 13591.3 10283.3 14243.8 8913.89 12577.7 13797.2 12483.6 320.2591420_MZ Alpha-Linolenoyl ethanolamide Un 1.0 None None None None C20H35NO2 None None None 1471.68 1557.59 1355.47 1568.91 1536.82 1178.41 1369.32 1631.85 1381.12 1361.35 1619.49 1453.49 1521.49 1460.51 1258.64 1302.56 1399.56 2036.85 1138.68 1660.71 1252.66 1194.41 1502.01 1564.43 1308.28 1236.86 1305.07 1726.82 1353.9 1603.27 1369.17 1381.32 1403.83 1428.74 1215.88 1575.39 1088.62 1570.53 1418.66 1535.65 1092.73 1332.89 321.0040401_MZ Ellagic acid Un 1.0 None None None None Ellagic acid is a Polyphenol compound found in numerous fruits and vegetables, including, raspberries; strawberries; cranberries; walnuts; pecans; pomegranates; and other plant foods. It is often regarded as an antioxidant. Ellagic Acid Clinical Tests on cultured human cells also show that Ellagic acid prevents the destruction of the p53 gene by cancer cells. Additional studies suggest that one of the mechanisms by which Ellagic acid inhibits mutagenesis and carcinogenesis is by forming adducts with DNA, thus masking binding sites to be occupied by the mutagen or carcinogen. C14H6O8 None None None 22313.7 23320.5 22521.6 24333.9 23712.0 22857.5 24335.4 22948.3 22595.5 24690.5 23865.1 22600.8 22738.8 23847.8 23865.1 26003.4 23830.3 24633.8 22454.7 23088.4 21446.6 22349.7 23028.9 21982.0 23711.4 23351.5 22717.8 23553.5 22449.1 23084.9 23337.5 26499.3 23622.2 22112.1 21893.7 22438.8 21750.4 23263.4 22166.9 22855.8 23776.7 22188.2 321.0165792_MZ Cyanidin Un 1.0 None None None None Cyanidin, or flavan-3-ol, is a natural organic compound which is classified as a flavonoid and an anthocyanin. It is a pigment found in many redberries including but not limited to bilberry, blackberry, blueberry, cherry, cranberry, elderberry, hawthorn, loganberry and raspberry. It can also be found in other fruits such as apples and plums. The highest concentrations of cyanidin are found in the skin of the fruit. Recently, the biosynthesis of cyanidin 3-O-glucoside in Escherichia coli was demonstrated. -- Wikipedia. C15H11ClO6 None None None 12101.0 12458.7 12711.4 13055.6 11731.7 12704.1 12446.5 11814.5 12936.2 13572.8 11918.0 13880.9 13491.0 11908.6 12600.3 13671.6 11703.5 14116.5 12520.0 12931.7 11493.6 12974.7 12064.7 11788.8 11974.8 13348.5 12234.7 12964.6 13171.9 13073.0 12644.1 13418.3 13354.2 11951.4 12919.5 12725.2 12417.0 13301.5 11576.0 12519.4 12468.7 12235.9 322.0450008_MZ Cytidine monophosphate Un 1.0 None None None None Cytidine monophosphate, also known as 5'-cytidylic acid and abbreviated CMP, is a nucleotide. It is an ester of phosphoric acid with the nucleoside cytidine. CMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase cytosine. Cytidine monophosphate (CMP) is derived from cytidine triphosphate (CTP) with subsequent loss of two phosphates. The synthesis of the pyrimidines CTP and UTP occurs in the cytoplasm and starts with the formation of carbamoyl phosphate from glutamine and CO2. Next, aspartate undergoes a condensation reaction with carbamoyl-phosphate to form orotic acid. In a subsequent cyclization reaction, the enzyme Aspartate carbamoyltransferase forms N-carbamoyl-aspartate which is converted into dihydroorotic acid by Dihydroorotase. The latter is converted to orotate by Dihydroorotate oxidase. Orotate is covalently linked with a phosphorylated ribosyl unit with Orotate phosphoribosyltransferase (aka PRPP transferase) catalyzing reaction, yielding orotidine monophosphate (OMP). Orotidine-5-phosphate is decarboxylated by Orotidine-5'-phosphate decarboxylase to form uridine monophosphate (UMP). UMP is phosphorylated by two kinases to uridine triphosphate (UTP) via two sequential reactions with ATP. CTP is subsequently formed by amination of UTP by the catalytic activity of CTP synthetase. Cytosine monophosphate (CMP) and uridine monophosphate (UMP) have been prescribed for the treatment of neuromuscular affections in humans. Patients treated with CMP/UMP recover from altered neurological functions. Additionally, the administration of CMP/UMP appears to favour the entry of glucose in the muscle and CMP/UMP may be important in maintaining the level of hepatic glycogen constant during exercise. [PMID:18663991]. C9H14N3O8P, Cytidine 2'-phosphate None None None 97975.6 86276.8 86844.1 77285.1 65737.3 59494.5 80350.9 69476.5 62004.4 59219.7 60113.2 73523.9 72251.1 82632.5 63389.7 70591.1 70581.1 73734.5 56712.1 63051.2 73963.9 66826.6 57034.9 84069.5 74142.4 64681.7 85572.5 55886.6 63922.6 81553.0 72629.4 56842.6 56672.7 52191.4 77135.5 67541.1 71925.8 68955.9 42076.0 58025.0 75159.1 71865.4 323.0279275_MZ Uridine 5'-monophosphate Un 1.0 None None None None 5'-Uridylic acid. A uracil nucleotide containing one phosphate group esterified to the sugar moiety in the 2', 3' or 5' position. Uridine 5'-monophosphate is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside uridine. UMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase uracil. (Wikipedia). C9H13N2O9P, Pseudouridine 5'-phosphate, Uridine 2'-phosphate None None None 762350.0 733684.0 1129280.0 1053560.0 995684.0 601730.0 1060770.0 788837.0 898762.0 681094.0 649145.0 785009.0 741569.0 523765.0 964575.0 497517.0 837296.0 606208.0 716946.0 739572.0 752271.0 855344.0 750100.0 687718.0 946020.0 982081.0 861606.0 696837.0 927811.0 651649.0 598452.0 480214.0 692925.0 715191.0 941800.0 783919.0 969264.0 887962.0 658675.0 777665.0 840386.0 783845.0 323.1274791_MZ DHAP(10:0) Un 1.0 None None None None DHAP(10:0) is the decanoyl derivative of Dihydroxyacetone phosphate. It is also known as an alkyl-DHAP. This compound is formed by decanoic acid reacting with DHAP. Alkyl-DHAPs are intermediates in the synthesis of ether phospholipids. The initial steps of ether phospholipid biosynthesis take place in peroxisomes. Alkyl-dihydroxyacetonephosphate synthase is the peroxisomal enzyme that actually introduces the ether linkage. Levels of Alkyl-DHAP have been found to be strongly reduced in human fibroblasts derived from Zellweger syndrome and rhizomelic chondrodysplasia punctata patients. Four other enzymes are known to be involved in the metabolism of acyl-DHAP and alkyl-DHAP. These include: acyl-DHAP/alkyl-DHAP oxidoreductase, DHAP acyltransferase, alkyl-DHAP phosphohydrolase, and a dinitrofluorobenzene-insensitive acyl-DHAP acylhydrolase. Dihydroxyacetone phosphate (DHAP) is a biochemical compound primarily involved in the glycolysis metabolic pathway. DHAP is also the product of the dehydrogenation of L-glycerol-3-phosphate which is part of the entry of glycerol (sourced from triglycerides) into the glycolytic pathway. Conversely, reduction of glycolysis-derived DHAP to L-glycerol-3-phosphate provides adipose cells with the activated glycerol backbone they require to synthesize new triglycerides. Both reactions are catalyzed by the enzyme glycerol 3-phosphate dehydrogenase with NAD+/NADH as cofactor. DHAP may be referred to as glycerone phosphate in older texts. C13H25O7P None None None 7248.76 4926.75 5972.77 7281.5 6294.71 6653.42 5593.61 5848.38 5146.55 5581.56 5519.96 4501.11 3242.28 5835.51 6942.8 6652.71 6563.07 3836.92 4749.33 5480.92 5192.0 4791.59 5657.93 4863.28 5975.34 4575.32 5884.37 4488.84 4282.9 7653.16 5756.77 5753.7 3260.09 5040.05 5518.29 5117.35 5828.69 4100.06 4689.16 5155.77 4822.87 4690.21 323.2039252_MZ 3a,16b-Dihydroxyandrostenone Un 1.0 None None None None 3a,16b-Dihydroxyandrostenone is an unusual steroid found in the urinary excretion of a subject having a virilizing malignant adrenocortical tumor; apparent 21-steroid hydroxylase deficiency is discussed at the light of these results and of the hormonogenesis enzymatic induction of the tumour biopsy. (PMID 198067). C19H28O3, 16-Oxoandrostenediol, 3a,16a-Dihydroxyandrostenone, 16a-Hydroxydehydroisoandrosterone, 3a,16-Dihydroxyandrostenone, 7a-Hydroxytestosterone, 7a-Hydroxydehydroepiandrosterone, 7b-Hydroxydehydroepiandrosterone, 11-Ketoetiocholanolone, 6beta-Hydroxytestosterone, 19-Hydroxytestosterone, 11beta-Hydroxytestosterone, 2beta-Hydroxytestosterone None None None 3020.56 3089.25 3009.16 3363.33 3144.83 3654.15 3477.8 3776.72 2642.63 2888.01 3576.75 2374.89 2429.6 3478.81 3299.56 3114.07 4481.22 3013.55 2332.21 3377.05 2917.95 1997.11 3281.21 3018.79 2970.62 2125.3 3415.35 3054.71 2166.24 3828.82 2995.64 2397.26 2266.85 2465.04 2273.13 2818.43 2226.08 2045.1 2011.89 2880.36 2563.98 2575.19 324.0927807_MZ N-Glycolylneuraminic acid Un 1.0 None None None None N-Glycolylneuraminic acid (Neu5Gc) is a widely expressed sialic acid found in most mammalian cells. Although humans are genetically deficient in producing Neu5Gc, small amounts are present in human cells and biofluids. Humans cannot synthesize Neu5Gc because the human gene CMAH is irreversibly mutated, though it is found in apes. This loss of the CMAH gene was estimated to have occurred two to three million years ago, just before the emergence of the genus Homo. A dietary origin of Neu5Gc was suggested by human volunteer studies. These trace amounts of Neu5Gc were determined to come from the consumption of animals in the human diet (i.e. red meats such as lamb, pork, and beef). Neu5Gc can also be found in dairy products, but to a lesser extent. Neu5Gc is not found in poultry and is found in only trace amounts in fish (Wikipedia). C11H19NO10 None None None 99861.6 54669.1 73657.2 49692.1 41329.0 98893.5 85466.5 64141.4 42937.7 80415.9 72972.5 132532.0 59123.4 232774.0 43202.1 43465.8 61820.3 51071.5 40664.7 38863.6 51169.9 66242.3 68023.7 67624.2 57629.7 39561.3 53100.5 53798.8 72969.3 46660.1 59392.4 55449.9 33510.1 51444.8 49344.4 65709.6 64812.6 74102.0 29513.4 67965.6 40316.2 70924.1 324.1713886_MZ 5'-Carboxy-gama-chromanol Un 1.0 None None None None C18H25O4 None None None 3520.04 3739.86 3536.97 3737.86 4129.26 4541.94 3996.5 3755.18 3243.81 3863.1 4065.77 4021.4 3129.84 5061.16 4041.37 3374.82 3724.23 3112.74 3042.55 3273.79 3481.21 3188.38 4057.91 4029.94 3494.73 3556.86 3852.3 3878.75 2791.44 4013.06 3093.96 3199.51 3106.04 3110.6 3477.35 3601.92 3213.82 3403.22 2098.85 3839.69 2852.09 2962.24 324.2913362_MZ N-Oleoylethanolamine Un 1.0 None None None None N-Oleoylethanolamine (NOE or OEA) is a N-acylethanolamine. N-acylethanolamines (NAEs) constitute a class of lipid compounds naturally present in both animal and plant membranes as constituents of the membrane-bound phospholipid, N-acylphosphatidylethanolamine (NAPE). NAPE is composed of a third fatty acid moiety linked to the amino head group of the commonly occurring membrane phospholipid, phosphatidylethanolamine. NAEs are released from NAPE by phospholipase D-type hydrolases in response to a variety of stimuli. Transient NAE release and accumulation has been attributed a variety of biological activities, including neurotransmission, membrane protection, and immunomodulation in animals. N-oleoylethanolamine is an inhibitor of the sphingolipid signaling pathway, via specific ceramidase inhibition (ceramidase converts ceramide to sphingosine). N-oleoylethanolamine blocks the effects of TNF- and arachidonic acid on intracellular Ca concentration. (PMID: 12692337, 12056855, 12560208, 11997249). N-oleoyl ethanolamine is related to the endocannabinoid anandamide. Endocannabinoids signal through cannabinoid receptors (also stimulated by the active ingredient of cannabis) but although related in structure, synthesis and degradation to anandamide, NOE cannot be considered an endocannabinoid as it does not activate the cannabinoid receptors. Most of the reported responses to NOE can be attributed to activation of peroxisome proliferator-activated receptor-alpha (PPAR-alpha). Administration of NOE inhibits body weight gain in rats. In adipocytes and hepatocytes, NOE inhibits mitogenic and metabolic signaling by the insulin receptor and produces glucose intolerance. It also inhibits gastric emptying, which might act together with the sensory neuronal signals to achieve satiety. NOE is permanently elevated in diabetic obese patients. NOE also reduces visceral and inflammatory responses through a PPAR-alpha-activation independent mechanism (PMID: 17449181). NOE has been shown to be an antagonist of TRVP1 (the transient receptor potential vanilloid type 1 receptor). Overall, NOE has beneficial effects on health by inducing food intake control, lipid beta-oxidation, body weight loss and analgesic effects (PMID: 18704536). C20H39NO2 None None None 1872.44 1866.8 1611.09 1768.75 1774.36 1519.18 2193.66 2173.48 1615.71 1621.94 1949.26 1977.1 2021.22 1956.8 1542.22 1414.98 2302.73 2852.65 1624.87 2331.37 1721.76 1380.93 1728.07 1761.84 1716.43 1547.73 1633.79 2394.45 1495.35 1775.16 1611.73 1415.64 1543.24 1922.85 1375.52 1633.58 1489.8 1710.06 1786.49 1770.3 1961.3 1606.93 325.0220285_MZ Uridine 2',3'-cyclic phosphate Un 1.0 None None None None Uridine 2',3'-cyclic phosphate is a cyclic nucleotide. A cyclic nucleotide is any nucleotide in which the phosphate group is bonded to two of the sugar's hydroxyl groups, forming a cyclical or ring structure. Cyclic phosphates are commonly found at the 3' end of mRNAs and other small RNAs. Uridine 2',3'-cyclic phosphate is a substrate for the enzyme 2',3'-cyclic nucleotide-3'-phosphodiesterase (CNPase, EC 3.1.4.37) which hydrolyses it to Uridine 2'-phosphate. CNPase is a unique RNase in that it only cleaves nucleoside 2',3'-cyclic phosphates and not the RNA internucleotide linkage, like other RNases such as RNase A and RNase T1. C9H11N2O8P None None None 15547.4 14555.1 16955.4 14834.5 16005.6 16023.1 14519.7 14616.7 19403.7 15274.3 18380.6 18165.9 13272.4 15341.7 16297.3 16077.4 15058.6 14212.9 15063.2 14193.5 16747.2 19711.6 15756.2 17518.8 14835.8 17325.4 16358.4 15590.5 18659.7 15393.4 13714.1 15802.3 19504.4 14779.2 21772.2 21665.3 17425.2 18587.3 13462.8 20072.9 13534.2 16159.5 326.1668426_MZ Zolpidem Un 1.0 None None None None Zolpidem (sold under the brand names Ambien, Ambien CR, Stilnox, and Sublinox) is a prescription medication used for the treatment of insomnia, as well as some brain disorders. It is a short-acting nonbenzodiazepine hypnotic of the imidazopyridine class that potentiates gamma-aminobutyric acid (GABA), an inhibitory neurotransmitter, by binding to GABAA receptors at the same location as benzodiazepines. It works quickly (usually within 15 minutes) and has a short half-life (two to three hours). Zolpidem has not adequately demonstrated effectiveness in maintaining sleep (unless delivered in a controlled-release form); however, it is effective in initiating sleep. Some users take zolpidem recreationally for these side effects. However, it may be less common than benzodiazepine abuse. Zolpidem can become addictive if taken for extended periods of time, due to dependence on its ability to put one to sleep or to the euphoria it can sometimes produce. C19H21N3O None None None 4974.28 4640.15 5085.25 4140.56 4505.38 6683.54 4925.55 5604.39 4346.02 4407.85 4600.78 4329.9 3808.21 4239.68 5472.73 9445.33 7140.48 4061.01 3990.57 4873.28 4483.98 3972.16 4630.05 4764.93 4286.6 3835.85 4726.94 4411.3 4337.52 5502.68 5127.81 7182.25 3380.79 3470.19 4314.93 5172.32 3725.53 4027.29 2696.38 4884.42 3467.51 3895.25 327.2327102_MZ Docosahexaenoic acid Un 1.0 None None None None Docosahexaenoic acid (DHA) is an omega-3 essential fatty acid. Chemically, DHA is a carboxylic acid with a 22-carbon chain and six cis double bonds with the first double bond is located at the third carbon from the omega end. DHA is most often found in fish oil. It is a major fatty acid in sperm and brain phospholipids, especially in the retina. Dietary DHA can reduce the level of blood triglycerides in humans, which may reduce the risk of heart disease. (wikipedia). C22H32O2 None None None 235223.0 236636.0 218559.0 310283.0 344980.0 266137.0 519303.0 546894.0 345635.0 150284.0 222118.0 262489.0 554225.0 268380.0 250454.0 157351.0 670494.0 810901.0 227971.0 563991.0 177117.0 189688.0 279674.0 236772.0 315177.0 218931.0 132784.0 397511.0 164558.0 322189.0 425801.0 171105.0 239066.0 257162.0 94733.0 408900.0 226880.0 400987.0 304290.0 251683.0 619648.0 283444.0 328.0483929_MZ Cyclic AMP Un 1.0 None None None None Cyclic AMP is an adenine nucleotide containing one phosphate group which is esterified to both the 3'- and 5'-positions of the sugar moiety. It is a second messenger and a key intracellular regulator, functioning as a mediator of activity for a number of hormones, including epinephrine, glucagon, and ACTH. cAMP is synthesized from ATP by adenylate cyclase. Adenylate cyclase is located at the cell membranes. Adenylate cyclase is activated by the hormones glucagon and adrenaline and by G protein. Liver adenylate cyclase responds more strongly to glucagon, and muscle adenylate cyclase responds more strongly to adrenaline. cAMP decomposition into AMP is catalyzed by the enzyme phosphodiesterase. C10H12N5O6P, Adenosine 2',3'-cyclic phosphate None None None 186735.0 141074.0 117864.0 109588.0 112667.0 192305.0 148990.0 154563.0 74850.5 81227.4 113909.0 55951.1 393089.0 140363.0 85286.2 159315.0 106098.0 226444.0 131020.0 202184.0 153084.0 59560.1 118760.0 127836.0 151739.0 82631.3 146315.0 133028.0 88986.6 110414.0 164197.0 167763.0 87891.3 91127.1 84045.3 137230.0 103610.0 69267.3 123919.0 134121.0 237264.0 204190.0 328.2123871_MZ 6-Keto-decanoylcarnitine Un 1.0 None None None None C17H31NO5 None None None 13463.0 2950.78 2306.49 3113.45 2123.56 8890.54 2875.69 3193.33 2232.2 8132.95 6084.83 1787.66 2321.26 12664.9 2122.74 2139.46 3742.66 2547.86 1956.26 2638.58 5474.13 1833.44 6252.95 5032.81 2441.07 2004.81 2307.81 2422.46 1759.87 21749.3 2145.84 2207.41 1568.13 2371.21 1870.51 2972.76 1960.91 1679.79 1853.74 2881.77 2215.01 2370.15 328.9832435_MZ Ribose 1,5-bisphosphate Un 1.0 None None None None Ribose 1,5-bisphosphate (Rib-1,5-P2), a newly discovered activator of phosphofructokinase. It forms rapidly during the initiation of glycolytic flux and disappears within 20 s/ Ribose 1,5-bisphosphate is a potent regulator of the fructose 6-phosphate/fructose 1,6-bisphosphate cycle in the liver. Ribose 1,5-bisphosphate is a substrate for Ribose 1,5-bisphosphate phosphokinase (EC 2.7.4.23), an enzyme that catalyzes the chemical reaction. ATP + ribose 1,5-bisphosphate <-> ADP + 5-phospho-alpha-D-ribose 1-diphosphate. C5H12O11P2 None None None 15746.9 16122.6 17487.9 20268.1 19598.2 16524.6 16795.6 16594.9 16363.2 17010.8 17992.3 17195.6 17427.1 17753.5 17962.4 19907.8 16560.2 17210.5 16884.3 15443.0 16753.6 16706.0 16068.4 16404.4 15647.3 18299.4 17546.9 16970.2 15576.3 16176.7 17617.8 20066.6 16789.9 15439.2 17588.9 17604.2 15984.9 16392.8 13667.2 16152.0 18182.0 17566.9 329.0295809_MZ Inosine 2',3'-cyclic phosphate Un 1.0 None None None None Inosine-2',3'-cyclic phosphate is a cyclic nucleotide. A cyclic nucleotide is any nucleotide in which the phosphate group is bonded to two of the sugar's hydroxyl groups, forming a cyclical or ring structure. 2',3' cyclic IMP is a substrate for 2',3'-cyclic-nucleotide 3'-phosphodiesterase (EC 3.1.4.37). This enzyme (also called CNP) catalyzes the chemical reaction: nucleoside 2',3'-cyclic phosphate + H2O <-> nucleoside 2'-phosphate. CNP is a myelin-associated enzyme that makes up 4% of total CNS myelin protein, and is thought to undergo significant age-associated changes. The absence of CNP causes axonal swelling and neuronal degeneration. The biological role of cyclic 2',3' monophosphates is not clear, although it is thought to have something to do with neuronal stasis or development. C10H11N4O7P None None None 12763.7 17070.0 14793.2 8269.22 10758.5 17983.0 9761.41 10036.4 10698.9 12971.9 11877.6 13021.9 9900.36 10287.0 10657.9 13320.1 9622.72 17634.9 13948.8 10612.2 14349.0 15775.4 11899.6 13293.4 11989.7 12829.9 10372.7 13261.4 16790.2 14643.0 11923.4 12348.2 14107.8 13801.4 14778.6 12461.4 14646.6 11931.6 9615.15 11240.3 8802.63 10533.6 329.1597973_MZ Picrocrocin Un 1.0 None None None None Picrocrocin is a glycoside formed from glucose and safranal. It is found in the spice saffron, which comes from the crocus flower. Picrocrocin has a bitter taste and is the chemical most responsible for the taste of saffron. It is believed that picrocrocin is a degradation product of the carotenoid zeaxanthin (Wikipedia). C16H26O7 None None None 13802.4 12774.3 18178.7 15016.6 13748.0 13231.5 14017.7 24836.3 8416.87 10953.0 10610.6 7909.58 9592.07 12162.1 19554.4 18382.9 38840.4 7741.07 10354.1 15136.7 10847.8 6590.75 10558.8 11748.7 12232.8 7236.83 15291.3 9946.05 7039.58 16611.1 12490.2 12428.8 6152.18 8125.63 8029.31 12954.1 7061.13 6856.52 8943.31 13748.3 7006.4 12372.6 329.2333228_MZ 9_10_13-TriHOME Un 1.0 None None None None 9,10,13-TriHOME is a trihydroxyoctadecenoic acid metabolite of linoleic acid, one of the major fatty acids found in lipids. Vascular tissue converts various polyunsaturated fatty acids to monohydroxy and trihydroxy metabolites derived from hydroperoxides which may be involved in regulating prostaglandin synthesis. C18H34O5, 9_12_13-TriHOME None None None 15618.5 12905.0 12577.8 15450.7 15564.8 15875.0 22163.1 21332.3 16459.1 12537.8 12361.3 9946.71 13754.1 15302.5 14442.4 11983.5 26789.0 23124.0 14922.5 19662.7 15137.1 9314.54 15738.7 14082.3 15534.2 10655.6 10502.1 15354.2 9005.51 16446.0 15474.7 10137.7 10516.1 17248.2 8205.24 18097.2 11593.7 13964.1 10681.8 13689.3 18421.1 16492.6 329.2479124_MZ Docosapentaenoic acid Un 1.0 None None None None Docosapentaenoic acid (also known as clupanodonic acid) is an essential omega-3 fatty acid (EFA) which is prevalent in fish oils. Docosapentaenoic acid, commonly called DPA, is an intermediary between eicosapentaenoic acid (EPA, 20:5 ω-3) and docosahexaenoic acid (DHA, 22:6 ω-3). Seal oil is a rich source. There are three functions of docosapentaenoic acid. The most important is as part of phospholipids in all animal cellular membranes: a deficiency of docosapentaenoic acid leads to faulty membranes being formed. A second is in the transport and oxidation of cholesterol: clupanodonic acid tends to lower plasma cholesterol. A third function is as a precursor of prostanoids which are only formed from docosapentaenoic acid. Deficiency of this in experimental animals causes lesions mainly attributable to faulty cellular membranes: sudden failure of growth, lesions of skin and kidney and connective tissue, erythrocyte fragility, impaired fertility, uncoupling of oxidation and phosphorylation. In man pure deficiency of docosapentaenoic acid has been studied particularly in persons fed intravenously. A relative deficiency (that is, a low ratio in the body of docosapentaenoic to long-chain saturated fatty acids and isomers of docosapentaenoate) is common on Western diets and plays an important part in the causation of atherosclerosis, coronary thrombosis, multiple sclerosis, the triopathy of diabetes mellitus, hypertension and certain forms of malignant disease. Various factors affect the dietary requirement of docosapentaenoic acid. (PMID: 6469703). C22H34O2, 4_7_10_13_16-Docosapentaenoic acid None None None 30044.2 25156.9 30178.5 31245.5 32470.1 20493.2 60739.8 70228.9 36590.5 23383.3 23219.7 30182.4 43486.5 41234.1 27309.0 16123.2 47342.9 83796.1 28423.5 71434.4 22251.3 17755.9 28580.4 34079.1 30538.9 20869.2 19855.0 53493.5 17977.2 37225.2 36392.2 17470.1 38537.6 28312.9 12473.1 38360.8 25940.8 36763.5 43770.3 28983.5 57367.6 47255.7 331.2636078_MZ Adrenic acid Un 1.0 None None None None Adrenic acid, which is a prostacyclin inhibitor, appears to be potential prothrombotic agent. (PMID 1642692). C22H36O2 None None None 13847.7 12705.2 14419.7 11278.3 18612.4 8704.68 27552.0 27896.6 16421.7 14491.9 11145.5 14628.8 21463.0 29765.9 19959.7 7646.53 18362.8 37052.6 13586.1 36606.0 13064.4 8423.45 13639.5 15750.3 15877.3 11494.8 9292.34 29709.8 9348.27 15558.2 15341.2 8372.71 27230.3 11326.7 7886.6 19123.4 14324.4 19498.5 24854.2 16727.2 23251.7 29441.4 333.0588962_MZ 1-(sn-Glycero-3-phospho)-1D-myo-inositol Un 1.0 None None None None 1-(sn-Glycero-3-phospho)-1D-myo-inositol or glycerophosphoinositol is produced through deacylation by phospholipase B of the essential phospholipid phosphatidylinositol. Glycerophosphoinositols are ubiquitous phosphoinositide metabolites involved in the control of several cell functions. They exert their actions both intracellularly and by rapidly equilibrating across the plasma membrane. Their transport is mediated by the Glut2 transporter, the human ortholog of GIT1 (PMID: 17141226). Glycerophosphoinositol is a substrate for glycerophosphoinositol inositolphosphodiesterase (EC 3.1.4.43) and is involved in the following reaction: 1-(sn-glycero-3-phospho)-1D-myo-inositol + H2O = glycerol + 1D-myo-inositol 1-phosphate. It is also a substrate for glycerophosphoinositol glycerophosphodiesterase (EC 3.1.4.44) which catalyzes the chemical reaction:. 1-(sn-glycero-3-phospho)-1D-myo-inositol + H2O = myo-inositol + sn-glycerol 3-phosphate. C9H19O11P None None None 66852.2 93428.3 82097.5 77256.4 121520.0 94274.0 70974.8 81678.9 81238.1 77369.8 70073.3 102899.0 72277.4 80954.9 88031.0 99707.1 103574.0 86443.6 92083.6 75072.6 70627.6 83825.1 104965.0 72253.6 85374.1 67253.3 118302.0 60994.3 71170.7 58549.5 82367.2 82762.5 70974.6 65738.4 78776.1 85301.9 90378.2 88524.0 34662.7 105654.0 75645.8 71495.1 333.2036844_MZ Prostaglandin A2 Un 1.0 None None None None C20H30O4, Leukotriene B5, Delta-12-Prostaglandin J2, 15-Keto-13_14-dihydroprostaglandin A2, 12-Keto-leukotriene B4, Prostaglandin B2, Prostaglandin J2 None None None 17883.1 19091.5 16837.0 21959.8 17437.2 19761.2 18377.2 18654.5 17075.7 14661.3 18926.7 17903.9 16592.2 18939.6 19138.1 20205.9 20525.5 18860.6 14108.9 21622.0 17000.9 14374.9 16860.5 18418.5 17235.8 15975.5 17420.9 17672.6 14565.9 19811.8 17282.5 14519.7 15943.5 15266.1 14705.8 17292.4 14392.5 15191.7 10500.8 18754.3 18374.2 16496.3 334.1248001_MZ Aspartylglycosamine Un 1.0 None None None None Large amount of aspartylglycosamine appears in patients with aspartylglycosaminuria, which is a metabolic disorder associated with decreased activity of aspartylglycosamine amido hydrolase. C12H21N3O8 None None None 15958.2 18928.4 15219.5 14702.1 14438.6 22255.0 14525.0 14215.4 16400.0 12883.4 18700.3 18721.6 10528.5 15558.1 19190.6 34802.3 13889.5 14800.8 13467.5 12618.1 14886.4 12123.7 15362.6 13361.2 13390.9 10819.1 17310.4 14866.9 13499.6 15850.8 18799.5 24124.8 10715.0 12145.3 15745.3 14102.3 11054.5 12669.6 9349.09 14788.6 13977.8 13008.1 335.2220820_MZ 11(R)-HPETE Un 1.0 None None None None 11R-HPETE is a hydroperoxyeicosatetraenoic acid eicosanoid derived from arachidonic acid. 11R-HPETE is formed from arachidonic acid in the prostaglandin endoperoxide H synthase-1 cyclooxygenase site. 11R-HPETE has been described in other mammalian tissues (rat, sheep). There are two distinct isozymes of prostaglandin H synthase (PGHS), the key enzyme in prostaglandin biosynthesis; PGHS-1 is generally considered to play a housekeeping role, whereas PGHS-2 has been linked to various pathological processes. Both PGHS isozymes have two catalytic activities; they are a cyclooxygenase activity that converts arachidonic acid (AA) to prostaglandin G2 (PGG2) and a peroxidase activity that catalyzes the transformation of PGG2 to prostaglandin H2. Oxygenase activity is completely abolished in aspirin-treated PGHS-1 (ASA-PGHS-1), whereas aspirin-treated PGHS-2 (ASA-PGHS-2) still catalyzes formation of 11(R)-HPETE. (PMID: 12664566, 15292194, 15964853, 12167656). C20H32O4, 11H-14_15-EETA, 12(R)-HPETE, 12(S)-Leukotriene B4, Hepoxilin A3, Prostaglandin A1, 8-iso-PGA1 None None None 13038.5 12015.8 12117.6 18305.1 16950.5 15184.7 15076.7 10957.1 13276.0 11358.1 13821.9 12411.1 8254.16 13584.3 19751.4 17424.4 14682.6 10664.5 10281.2 14578.3 12246.1 11522.5 13587.0 13330.5 15685.8 12364.6 12825.9 11284.2 11451.4 13952.8 13356.1 10891.2 20579.7 9482.04 10838.8 12218.2 10473.2 10978.9 7457.28 13604.2 13018.3 13867.2 337.2373758_MZ 8_9-DiHETrE Un 1.0 None None None None 8,9-DiHETrE is a Cytochrome P450 (P450) eicosanoid. Eicosanoids generated from arachidonic acid (AA) metabolism by cytochrome P450 (P450) enzymes are important autocrine and paracrine factors that have diverse biological functions. P450 eicosanoids are involved in the regulation of vascular tone, renal tubular transport, cardiac contractility, cellular proliferation, and inflammation. P450converts AA to 8,9- dihydroxyeicosatrienoic acid. This enzymatic pathway was first described in liver; however, it is now clear that AA can be metabolized by P450 in many tissues including the pituitary gland, eye, kidney, adrenal gland, and blood vessels. (PMID: 17431031, 11700990). C20H34O4, 14_15-DiHETrE, 12-Keto-tetrahydro-leukotriene B4, 11_12-DiHETrE None None None 11626.7 9580.68 11274.4 9959.06 10100.6 15081.6 14706.8 13049.1 8651.29 10951.0 10246.9 8385.33 11120.4 10804.9 11817.2 11386.5 18571.5 16406.1 10368.5 14014.8 8840.63 6528.17 10314.2 10818.3 11003.8 8231.64 10592.4 12136.7 6984.39 11106.6 10803.8 9323.52 7621.57 9400.06 7712.31 10351.5 7074.07 7263.53 7783.47 10917.9 14059.6 10468.8 337.3105385_MZ Cetoleic acid Un 1.0 None None None None Cetoleic acid is a poly-unsaturated fatty acid. Source: fish oils and rapeseed. Found as a lipid membrane component. C22H42O2, Erucic acid None None None 4907.79 4294.22 5769.13 3703.3 5030.02 6025.09 5914.35 6976.82 4154.02 3567.5 4840.95 4779.03 7707.47 8536.52 4709.32 3649.56 4528.77 12139.3 4163.26 8345.93 3952.56 3276.63 4327.79 6089.4 7420.42 4756.92 4180.38 7980.44 5305.55 4503.96 4287.55 3048.77 6281.25 4674.53 3131.57 5879.18 5006.78 4164.74 7625.51 4204.33 10365.2 5937.49 338.2746820_MZ Oleoyl glycine Un 1.0 None None None None N-oleoyl glycine is an acylglycine with oleoic acid (C18:1(9Z))moiety attached to glycine molecule. It is reported to be preferentially produced by human glycine N-acyltransferase-like 2 (hGLYATL2), a member of a gene family of 4 putative glycine conjugating enzymes, synthesizes various N-acyl glycines. Recombinantly expressed hGLYATL2 efficiently conjugated oleoyl-CoA, arachidonoyl-CoA, and other medium- and long-chain acyl-CoAs to glycine. The enzyme was specific for glycine as an acceptor molecule. C20H37NO3 None None None 1269.22 1167.49 1290.77 1347.76 990.567 1314.96 1395.3 1885.45 966.414 1034.26 1246.58 1030.87 914.936 1254.63 1182.07 1122.73 2238.45 1313.64 955.689 1365.94 1064.6 812.308 1000.84 1102.76 962.372 987.818 1107.32 1216.28 719.565 1268.42 1009.84 1011.96 844.137 908.896 846.772 1169.52 847.596 859.517 938.426 1138.37 986.911 898.815 338.9882089_MZ D-Fructose 2,6-bisphosphate Un 1.0 None None None None D-Fructose 2,6-bisphosphate is a regulatory molecule controlling the activity of the enzyme Phosphofructokinase-1 or PFK1 (in mammals). PFK1, in turn, is the key regulatory enzyme in the central metabolic pathway Glycolysis. D-Fructose 2,6-bisphosphate has the effect of increasing the activity of PFK1, thus increasing the rate at which the principle food molecule glucose is broken down. At the same time, this regulatory molecule also inhibits the opposing enzyme (FBPase1) in the reverse pathway (gluconeogenesis) so that the synthesis of glucose is not taking place in the same cell where glucose is being broken down (which would be wasteful) (Wikipedia). C6H14O12P2, 1D-Myo-inositol 1,4-bisphosphate, Alpha-D-Glucose 1,6-bisphosphate, 1D-Myo-inositol 1,3-bisphosphate, 1D-Myo-inositol 3,4-bisphosphate, D-Tagatose 1,6-bisphosphate None None None 17838.5 18953.4 21523.9 8131.02 20643.7 20937.2 29596.6 41961.8 18529.2 15187.4 17951.5 29733.8 20937.9 21380.4 18892.5 30286.4 25109.3 18425.4 17775.8 34613.8 18539.3 14334.7 19296.8 17166.8 19815.8 23716.9 27998.1 15085.8 12337.6 27300.4 48138.0 21136.6 23026.6 21714.2 12344.9 12509.6 12524.1 18705.0 10436.7 14952.2 35331.3 15246.4 341.1083159_MZ D-Maltose Un 1.0 None None None None Maltose, or malt sugar, is a primary disaccharide in the human diet formed from two units of glucose joined with an alpha (1->4) linkage. It is the second member of an important biochemical series of glucose chains. The addition of another glucose unit yields maltotriose, Further additions will produce dextrins, also called maltodextrins, and eventually starch. Maltose can be broken down into two glucose molecules by hydrolysis in living organisms. At the surface of the small intestine, the brush border enzymes maltase, breaks down maltose. (PMID: 14522745). C12H22O11, Melibiose, Cellobiose, Alpha-Lactose, Sucrose, Lactulose, Trehalose, Isomaltose, Galactinol, 3-b-Galactopyranosyl glucose, Epimelibiose, Turanose, Kojibiose None None None 50025.4 51859.0 58917.6 29896.0 31340.6 57139.5 44388.8 40035.7 52543.2 70023.1 50853.6 53732.9 50206.7 52575.0 55499.9 61609.2 29203.8 45236.1 84218.9 55393.8 60236.9 62511.9 70792.6 52928.3 38578.2 45700.8 83442.3 62605.0 84797.7 136682.0 57281.9 41515.3 38929.4 81246.5 69071.3 77372.5 49329.4 54962.1 34748.2 59829.7 55519.6 51047.8 341.1962063_MZ 2_3-Dinor-6-keto-prostaglandin F1 a Un 1.0 None None None None 2,3-dinor-6-keto-prostaglandin F1 alpha is a major urinary prostacyclin metabolite, and is significantly higher in 9 patients with severe atherosclerosis and evidence of platelet activation. Prostacyclin is a potent vasodilator and platelet inhibitor produced by vascular endothelium. Endogenous production of prostacyclin under physiologic conditions is extremely low, far below the capacity of vascular tissue to generate this substance in response to stimulation in vitro. This may reflect a low frequency or intensity of stimulation of prostacyclin production. PGI2 synthase (PGIS), a catalyst of PGI2 formation from prostaglandin H2, is widely distributed and predominantly found in vascular endothelial and smooth muscle cells. PGI2 plays an important cardioprotective role increasingly appreciated in recent years in light of adverse effects of COX-2 inhibitors in clinical trials. This cardioprotection is thought to be mediated, in part, by prostacyclin inhibition of platelet aggregation. Multiple lines of evidence suggest that prostacyclin additionally protects from cardiovascular disease by pleiotropic effects on vascular smooth muscle. PGI2 inhibits proliferation of cultured vascular SMCs by inhibiting cell cycle progression from G1 to S phase. (PMID: 6231483, 7000774, 6231483, 16303599, 16533160, 17073611, 17164138)Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways. C18H30O6, 2_3-Dinor-TXB2 None None None 22462.4 22585.8 24568.0 23718.5 21216.4 23001.3 24202.6 29358.1 18773.6 22836.8 23795.5 20988.6 19759.5 21767.6 25950.8 23485.7 37395.2 22933.1 19515.0 23815.2 21844.3 16373.4 23814.2 23233.3 21544.8 17654.4 22256.2 22283.1 16347.7 24175.2 20302.4 19338.5 16795.8 18301.7 17665.9 22416.5 16700.0 17636.1 17797.4 22009.4 18071.2 20610.0 342.9987868_MZ Fructose 1_6-bisphosphate Un 1.0 None None None None C6H14O11P2 None None None 12777.9 11653.7 14540.3 10235.5 12969.2 11838.3 14940.3 15183.2 13117.2 12824.2 13859.3 14333.9 14345.9 12426.4 14349.1 11524.8 15606.6 20434.6 14721.2 15192.4 12686.6 13011.9 11689.3 13030.6 13431.0 12770.4 12221.4 14233.7 13080.9 13860.8 11873.4 11458.4 15547.2 14789.2 12770.5 13417.3 14170.1 13790.9 15577.4 13819.2 13205.0 12666.0 343.1150853_MZ Dolichyl diphosphate Un 1.0 None None None None The glycosylation of asparagine residues in proteins is known to occur by transfer from a dolichyl diphosphate oligosaccharide containing glucose. The addition of all three glucoses to the dolichyl diphosphate oligosaccharide occur with dolichyl phosphate glucose as donor.(http://www.blackwell-synergy.com/links/doi/10.1111/j.1432-1033.1980.tb04498.x/abs/). C12H26O7P2 None None None 12033.8 6934.53 8198.99 7139.3 8268.34 9457.22 7655.61 7355.69 6396.32 8551.22 8527.54 7513.22 5706.58 10058.8 8975.64 8657.11 7581.42 6086.46 7967.48 9920.14 8710.62 7136.51 9011.38 7756.34 6378.06 6904.78 9094.15 6992.78 7597.74 14005.8 9571.29 6939.66 5583.29 7691.29 7968.17 7778.44 6122.02 6574.08 4452.03 7662.2 8239.5 6480.15 343.1933046_MZ 11-Dehydrocorticosterone Un 1.0 None None None None 11-Dehydrocorticosterone is a mineral corticosteroid. The conversion of inactive 11-ketoglucocorticoids such as 11-dehydrocorticosterone) into active 11b-hydroxyglucocorticoids (such as corticosterone) is catalyzed by 11beta-hydroxysteroid dehydrogenase (11b-HSD1, EC 1.1.1.146), which is expressed in many tissues and plays an important role in metabolically relevant tissues such as the liver, adipose tissue, skeletal muscles and possibly kidney. Chronically elevated local glucocorticoid action as a result of increased 11beta-HSD1 activity rather than elevated systemic glucocorticoid levels has been associated with metabolic syndrome, which is characterized by obesity, insulin resistance, type 2 diabetes and cardiovascular complications. Recent studies indicate that compounds inhibiting 11beta-HSD1 activity ameliorate the adverse effects of excessive glucocorticoid concentrations on metabolic processes, providing promising opportunities for the development of therapeutic interventions. 11-dehydrocorticosterone and corticosterone display antinatriuretic activity, although 11-dehydrocorticosterone is generally a more potent sodium retainer than corticosterone. (PMID: 17584152, Endocr Metab Immune Disord Drug Targets. 2007 Jun;7(2):125-40.). C21H28O4, Formebolone, 19-Oxo-deoxycorticosterone None None None 5444.57 6188.57 5379.52 6027.79 6274.12 5551.22 5698.28 5756.05 6193.15 5659.65 5405.17 4254.54 3333.17 6040.54 5880.16 4624.78 7134.99 3657.74 4120.06 5336.51 4990.58 4016.62 5006.94 5415.25 5392.11 4554.68 5457.76 5125.29 3982.18 6359.44 4751.61 4252.5 3896.92 4895.44 5008.75 6453.6 4007.87 3781.83 3039.89 5345.19 4504.67 4673.55 346.0560069_MZ Adenosine monophosphate Un 1.0 None None None None Adenosine monophosphate, also known as 5'-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. AMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase adenine. AMP can be produced during ATP synthesis by the enzyme adenylate kinase. AMP has recently been approved as a 'Bitter Blocker' additive to foodstuffs. When AMP is added to bitter foods or foods with a bitter aftertaste it makes them seem 'sweeter'. This potentially makes lower calorie food products more palatable. C10H14N5O7P, 2'-Deoxyguanosine 5'-monophosphate, 3'-AMP, Adenosine 2'-phosphate None None None 4525220.0 5663200.0 6964280.0 7351880.0 6780120.0 5033340.0 7255170.0 5627420.0 6639580.0 5869590.0 4637940.0 5519860.0 6720780.0 4152000.0 7511080.0 4128310.0 6105590.0 5762460.0 6359130.0 5097420.0 5758710.0 6363720.0 5783390.0 5351280.0 6292710.0 5826440.0 6775420.0 5395010.0 6621910.0 5347230.0 4169000.0 3789580.0 5092320.0 5573420.0 8503940.0 5527730.0 6266780.0 6835500.0 4972090.0 6112680.0 5929060.0 6048960.0 347.0398567_MZ Inosine 2'-phosphate Un 1.0 None None None None Inosine 2'-phosphate is an inosine nucleotide containing a pyrophosphate group esterified to C2 of the sugar moiety. Inosine 2'-phosphate is a product of 2',3'-cyclic-nucleotide 3'-phosphodiesterase (EC 3.1.4.37). This enzyme (also called CNP) catalyzes the chemical reaction: nucleoside 2',3'-cyclic phosphate + H2O <-> nucleoside 2'-phosphate. 2',3'-cyclic nucleotide 3'-phosphodiesterase is a myelin-associated enzyme that makes up 4% of total CNS myelin protein, and is thought to undergo significant age-associated changes. The absence of CNP causes axonal swelling and neuronal degeneration. C10H13N4O8P, Inosinic acid None None None 407066.0 197742.0 228143.0 186521.0 183370.0 400131.0 261192.0 194598.0 233516.0 430226.0 530243.0 383621.0 346791.0 316558.0 228204.0 137663.0 179720.0 239759.0 404513.0 226897.0 543322.0 222142.0 349572.0 349966.0 249084.0 379961.0 282962.0 282728.0 179551.0 370044.0 287716.0 285472.0 185586.0 234496.0 258770.0 733555.0 285789.0 253889.0 129330.0 579942.0 353351.0 590211.0 349.2743612_MZ Monoacylglyceride(0:0/16:0/0:0) Un 1.0 None None None None MG(0:0/16:0/0:0) is a monoacylglyceride. A monoglyceride, more correctly known as a monoacylglycerol, is a glyceride consisting of one fatty acid chain covalently bonded to a glycerol molecule through an ester linkage. Monoacylglycerol can be broadly divided into two groups; 1-monoacylglycerols (or 3-monoacylglycerols) and 2-monoacylglycerols, depending on the position of the ester bond on the glycerol moiety. Normally the 1-/3-isomers are not distinguished from each other and are termed 'alpha-monoacylglycerols', while the 2-isomers are beta-monoacylglycerols. Monoacylglycerols are formed biochemically via release of a fatty acid from diacylglycerol by diacylglycerol lipase or hormone sensitive lipase. Monoacylglycerols are broken down by monoacylglycerol lipase. They tend to be minor components only of most plant and animal tissues, and indeed would not be expected to accumulate because their strong detergent properties would have a disruptive effect on membranes. 2-Monoacylglycerols are a major end product of the intestinal digestion of dietary fats in animals via the enzyme pancreatic lipase. They are taken up directly by the intestinal cells and converted to triacylglycerols via the monoacylglycerol pathway before being transported in lymph to the liver. Mono- and Diglycerides are commonly added to commercial food products in small quantities. They act as emulsifiers, helping to mix ingredients such as oil and water that would not otherwise blend well. C19H38O4, Monoacylglyceride(16:0/0:0/0:0) None None None 12437.0 10069.2 11600.6 10014.6 11966.1 14182.0 13831.9 13788.7 10853.5 14876.2 14324.2 10703.0 13846.8 14788.5 12458.1 9752.28 18437.7 24366.1 13092.4 15152.9 10999.2 9595.94 15569.7 13717.9 12036.9 10335.6 10540.6 15250.9 9577.55 10700.4 11481.3 8997.7 11823.5 9416.96 9478.04 16985.6 11324.8 9857.14 13169.0 10526.6 19871.1 19403.7 351.1253258_MZ Estradiol-17beta 3-sulfate Un 1.0 None None None None The estrogen patch is a delivery system for estradiol used as hormone replacement therapy to treat the symptoms of menopause, such as hot flashes and vaginal dryness, and to prevent osteoporosis. Originally marketed as Vivelle(Novartis), it was discontinued in 2003 and reintroduced in a smaller form as Vivelle-Dot. Although the estrogen is given transdermally rather than in the standard oral tablets, the estrogen patch carries similar risks and benefits as more conventional forms of estrogen-only hormone replacement therapy. C18H24O5S None None None 10271.4 9068.15 8504.88 9874.81 8718.44 16228.0 8403.42 7995.58 6509.62 12239.9 12641.3 9416.11 4349.94 9109.56 10187.6 14685.6 9616.4 4088.32 6678.24 5682.09 9739.04 6093.23 11451.4 8368.61 8446.8 6083.81 8692.82 7026.31 7479.23 11551.7 9478.87 15187.7 5818.3 6578.02 8392.49 7916.06 6484.9 8001.34 4006.27 7482.46 4465.96 5949.8 351.1974291_MZ 11b-Hydroxyprogesterone Un 1.0 None None None None 11beta-Hydroxyprogesterone is a normal human metabolite. Plasma 11beta-Hydroxyprogesterone concentrations does not vary significantly as a function of age, sex, or phase of the menstrual cycle, in contrast to 17-hydroxyprogesterone. Increased plasma 11beta-Hydroxyprogesterone levels in late-onset adrenal 21-hydroxylase deficiency suggest a mild defect of the mineralocorticoid pathway. 21-hydroxylase deficiency (OMIM 201910) is probably the most frequent (if not the most frequent) autosomal recessive genetic disease, occurring in almost 1% of Caucasians and about 3% of Ashkenazi Jews. 21-hydroxylase deficiency is unusual among genetic diseases in that approximately 95% of the mutant alleles have apparently been generated by recombination between a normally active gene (CYP21) and a closely linked pseudogene (CYP21P). There are 4 recognized clinical forms of congenital adrenal hyperplasia, the majority of cases being associated with 21-hydroxylase deficiency: salt-wasting (SW), simple virilizing (SV), nonclassic (NC) late-onset (also called attenuated and acquired), and cryptic. (PMID: 3546944, 2537337). 11beta-hydroxyprogesterone acts as a mineralocorticoid agonist in stimulating Na+ absorption in mammalian principal cortical collecting duct cells.It activates the transiently expressed hMR in COS-7 cells in a dose-dependent manner (ED(50): 10(-8) M) and, like aldosterone, stimulated Ams I(sc) in mpkCCD(cl4) cells. Docking 11OHP within the hMR-ligand-binding domain homology model revealed that the agonist activity of 11OHP is caused by contacts between its 11 beta-hydroxyl group and Asn770. Furthermore, 11OHP was unable to activate the mutant hMR/N770A, in which Ala is substituted for Asn at position 770. These findings demonstrate that in the absence of the 21-hydroxyl group, the 11 beta-hydroxyl group can produce the contact with the hMR-Asn770 required for the hMR activation leading to stimulated Na(+) absorption. C20H28O4, Carnosic acid None None None 5391.08 4795.76 4158.69 4910.08 4551.52 6007.25 5720.19 5182.17 3979.91 4644.86 5195.13 3593.75 3136.79 5166.07 5264.7 4832.73 6166.68 4359.04 4283.8 5277.53 4082.44 3110.22 4911.77 4627.44 4683.89 3285.24 5320.5 3919.13 3065.96 6012.64 4371.15 3784.61 3375.05 3771.21 3298.76 4704.2 2788.11 2981.86 2798.75 4614.91 4760.95 4519.45 351.2538336_MZ Monoacylglyceride with formula C21H36O4 Un 1.0 None None None None MG(0:0/18:3(6Z,9Z,12Z)/0:0) is a monoacylglyceride. A monoglyceride, more correctly known as a monoacylglycerol, is a glyceride consisting of one fatty acid chain covalently bonded to a glycerol molecule through an ester linkage. Monoacylglycerol can be broadly divided into two groups; 1-monoacylglycerols (or 3-monoacylglycerols) and 2-monoacylglycerols, depending on the position of the ester bond on the glycerol moiety. Normally the 1-/3-isomers are not distinguished from each other and are termed 'alpha-monoacylglycerols', while the 2-isomers are beta-monoacylglycerols. Monoacylglycerols are formed biochemically via release of a fatty acid from diacylglycerol by diacylglycerol lipase or hormone sensitive lipase. Monoacylglycerols are broken down by monoacylglycerol lipase. They tend to be minor components only of most plant and animal tissues, and indeed would not be expected to accumulate because their strong detergent properties would have a disruptive effect on membranes. 2-Monoacylglycerols are a major end product of the intestinal digestion of dietary fats in animals via the enzyme pancreatic lipase. They are taken up directly by the intestinal cells and converted to triacylglycerols via the monoacylglycerol pathway before being transported in lymph to the liver. Mono- and Diglycerides are commonly added to commercial food products in small quantities. They act as emulsifiers, helping to mix ingredients such as oil and water that would not otherwise blend well. C21H36O4 None None None 9328.84 8136.13 5431.04 8581.81 8597.51 9460.01 7170.65 8681.1 6824.36 9936.8 9239.1 3367.8 5130.03 9384.28 8897.72 8110.46 12419.4 8936.18 8631.89 9076.78 8516.14 3710.55 9043.16 9350.08 8874.52 3745.43 8094.73 5952.73 3895.93 9819.46 6414.87 6954.47 4109.89 6395.6 3121.43 8252.41 5781.98 2679.5 6122.25 8449.59 7065.62 10023.0 352.1154679_MZ Protopine Un 1.0 None None None None Protopine is a benzylisoquinoline alkaloid occurring in opium poppies and other plants of the family papaveraceae. It has been found to inhibit histamine H1 receptors and platelet aggregation, and acts as an opioid analgesic. C20H19NO5 None None None 9886.39 8617.27 10225.5 12231.1 9126.29 13075.1 7334.13 5451.89 7069.72 12112.0 10112.4 9455.75 4747.78 9555.23 7974.34 8282.94 7345.27 4127.02 7063.28 5808.93 8974.5 6717.0 9827.72 7875.38 6351.2 7463.79 7170.7 6571.64 6928.95 11486.8 6687.27 7509.25 6280.53 6276.55 8735.19 7528.05 6933.01 7443.73 3914.03 7694.43 4543.64 6064.88 353.3417156_MZ Tricosanoic acid Un 1.0 None None None None Tricosanoic acid is found in different plant oils and extracts such as the Brazilian peppertree, but it can also be produced in the human body. It has shown to be a hair growth stimulant. C23H46O2 None None None 11011.7 11515.7 10117.7 10099.6 10740.6 9373.63 11471.8 12969.6 10124.1 10723.8 11456.1 10624.5 11122.7 11448.7 9457.32 9301.48 12688.8 15458.6 9705.19 12521.0 9330.21 9109.79 10093.9 11179.7 10491.0 9555.87 9661.4 12750.9 9159.78 11907.4 9703.52 8803.59 10108.1 10557.7 9390.11 10763.8 8781.28 10313.5 11014.8 10343.5 9112.71 9620.7 354.0604072_MZ Dihydroneopterin phosphate Un 1.0 None None None None Dihydroneopterin phosphate is involved in the folate biosynthesis pathway. Dihydroneopterin phosphate is produced from 2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine. triphosphate by [E3.6.1.-]. Dihydroneopterin phosphate is then converted to Dihydroneopterin by [E3.6.1.-]. C9H14N5O7P None None None 11514.4 13228.7 11827.5 8467.77 11109.6 13953.6 19205.1 17364.6 18552.2 10214.9 11381.2 20527.4 8980.27 13659.6 15041.9 11190.1 17077.6 8905.84 13022.1 14535.2 10493.5 20225.3 14675.6 13007.3 10973.5 11592.2 12235.3 10336.5 11825.0 12220.8 11645.1 9250.66 19699.9 12404.6 12285.2 9543.74 15825.1 18685.6 8395.52 13594.7 8658.76 10271.8 354.1320383_MZ Aspartylglycosamine Un 1.0 None None None None Large amount of aspartylglycosamine appears in patients with aspartylglycosaminuria, which is a metabolic disorder associated with decreased activity of aspartylglycosamine amido hydrolase. C12H21N3O8 None None None 5716.47 6855.8 6847.77 6837.05 7125.1 7637.47 5850.03 5745.94 5794.44 6498.15 6953.78 7011.04 3396.11 6835.48 7040.67 6688.85 6900.32 4421.87 5849.15 5107.69 6067.85 6035.06 6767.79 6280.7 5756.06 5968.77 6581.02 5781.48 5654.94 6916.87 5464.58 5538.27 5997.4 5244.66 6651.67 5791.65 5387.5 6376.78 4370.95 6265.13 4418.83 5157.48 355.2840925_MZ Monoacylglyceride with formula C21H40O4 Un 1.0 None None None None MG(0:0/18:1(11Z)/0:0) is a monoacylglyceride. A monoglyceride, more correctly known as a monoacylglycerol, is a glyceride consisting of one fatty acid chain covalently bonded to a glycerol molecule through an ester linkage. Monoacylglycerol can be broadly divided into two groups; 1-monoacylglycerols (or 3-monoacylglycerols) and 2-monoacylglycerols, depending on the position of the ester bond on the glycerol moiety. Normally the 1-/3-isomers are not distinguished from each other and are termed 'alpha-monoacylglycerols', while the 2-isomers are beta-monoacylglycerols. Monoacylglycerols are formed biochemically via release of a fatty acid from diacylglycerol by diacylglycerol lipase or hormone sensitive lipase. Monoacylglycerols are broken down by monoacylglycerol lipase. They tend to be minor components only of most plant and animal tissues, and indeed would not be expected to accumulate because their strong detergent properties would have a disruptive effect on membranes. 2-Monoacylglycerols are a major end product of the intestinal digestion of dietary fats in animals via the enzyme pancreatic lipase. They are taken up directly by the intestinal cells and converted to triacylglycerols via the monoacylglycerol pathway before being transported in lymph to the liver. Mono- and Diglycerides are commonly added to commercial food products in small quantities. They act as emulsifiers, helping to mix ingredients such as oil and water that would not otherwise blend well. C21H40O4 None None None 5827.83 5313.43 9360.19 5399.89 6458.21 6185.76 7789.03 14059.0 4600.88 4898.37 5515.58 4031.3 6358.67 5987.61 9127.12 6734.61 21512.6 7179.29 5051.64 9448.72 4738.09 3703.42 4825.13 5382.77 5812.71 4165.69 6666.87 6128.82 3663.16 6075.73 5726.64 4730.38 4253.92 4274.66 3905.74 5871.44 4163.95 3973.4 6322.91 5982.41 5865.74 6325.33 356.0917985_MZ S-(Hydroxymethyl)glutathione Un 1.0 None None None None S-Hydroxymethylglutathione is a critical component of the binding site for activating fatty acids in glutathione-dependent formaldehyde dehydrogenase activity. (OMIM 103710). formaldehyde dehydrogenase (FDH; EC 1.2.1.1), a widely occurring enzyme catalyzes the oxidation of S-hydroxymethylglutathione into S-formylglutathione in the presence of NAD (PubMed ID 2806555). C11H19N3O7S None None None 15899.7 14679.9 16060.3 10190.9 12863.1 19654.4 13208.3 14132.2 9439.64 13772.0 11232.9 17793.5 10239.0 10787.3 13256.2 14989.6 11194.3 11592.0 11572.0 16817.6 16812.2 11828.6 10687.1 14309.1 12508.5 14079.1 10012.3 12332.6 15405.7 15345.0 15115.1 11642.8 13855.4 12680.7 13560.9 14692.3 10582.7 12211.6 9182.56 11660.2 11081.3 10970.5 357.0806379_MZ N1-(5-Phospho-a-D-ribosyl)-5,6-dimethylbenzimidazole Un 1.0 None None None None N1-(5-Phospho-alpha-D-ribosyl)-5,6-dimethylbenzimidazole (or alpha-ribazole-5'-Phosphate) is an intermediate in Riboflavin metabolism. In particular, alpha-Ribazole 5'-phosphate is converted from Dimethylbenzimidazole via the enzyme nicotinate-nucleotide-dimethylbenzimidazole. phosphoribosyltransferase (EC 2.4.2.21). It is then converted to alpha-Ribazole via the enzyme (EC 3.1.3.-). C14H19N2O7P None None None 9755.92 9518.89 10510.7 12439.6 12683.6 11117.8 11071.1 11699.2 8839.17 10693.6 9779.29 10616.5 9773.42 8821.84 12700.3 12915.9 10913.9 9821.4 13048.1 11518.8 9129.13 7576.89 9993.35 8737.76 12107.5 8347.75 15738.9 7958.66 8062.43 9848.07 11810.2 9941.02 9529.03 10247.7 8161.95 9067.39 8417.52 8350.71 6126.7 9295.58 14537.8 10135.8 357.1411889_MZ Nicotine glucuronide Un 1.0 None None None None Nicotine glucuronidation results in an N-quaternary glucuronide in humans. This reaction is catalyzed by uridine diphosphate-glucuronosyltransferase (UGT) enzyme(s) producing (S)-nicotine-N-beta-glucuronide (Nicotine-Gluc). About 3-5% of nicotine is converted to Nicotine-Gluc and excreted in urine in humans. C16H22N2O6 None None None 8245.0 6830.63 11355.6 10816.7 10023.6 9264.0 9948.36 9070.83 8106.65 7528.67 9046.09 9399.33 12633.7 8701.92 8936.75 9358.78 9094.13 7908.98 8765.15 9408.33 10165.4 8389.85 8474.89 8828.42 9084.09 7269.36 9386.19 7626.33 9414.93 8177.97 9106.41 7977.63 8972.34 7153.46 8323.32 12433.2 6637.25 8116.56 4826.7 9090.45 11157.9 9127.76 357.1726817_MZ Malabaricone C Un 1.0 None None None None Malabaricone C is an antimicrobial resorcinol found in nutmeg, the dried seed covers of Myristica fragrans and Myristica malabarica (rampatri). This Compound exhibits strong antifungal and antibacterial activity. (PMID 1955885, 10501006). Malabaricone C a diarylnonanoid, shows strong scavenging activity. (PMID 16104820). C21H26O5 None None None 7803.66 7362.66 7939.99 9168.5 10009.1 9399.59 9364.45 8312.41 8708.56 7310.02 9023.66 7816.32 6176.66 9048.77 9899.76 9261.77 11136.5 5256.07 8344.17 7301.96 7525.42 7208.96 8618.18 8424.91 8248.36 6313.7 12163.6 6846.57 6398.17 9448.39 7906.33 8355.98 6956.83 5806.4 7146.45 9069.27 6340.24 7207.38 3415.99 9180.22 7872.73 8149.08 357.2638236_MZ 13,14-Dihydro PGF-1a Un 1.0 None None None None 13,14-Dihydro PGF-1alpha is a prostanoid. Prostanoids is a term that collectively describes prostaglandins, prostacyclines and thromboxanes. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2). The reaction product of COX is the unstable endoperoxide prostaglandin H (PGH) that is further transformed into the individual prostanoids by a series of specific prostanoid synthases. Prostanoids are local-acting mediators formed and inactivated within the same or neighbouring cells prior to their release into circulation as inactive metabolites (15-keto- and 13,14-dihydroketo metabolites). Non-enzymatic peroxidation of arachidonic acid and other fatty acids in vivo can result in prostaglandin-like substances isomeric to the COX-derived prostaglandins that are termed isoprostanes. Prostanoids take part in many physiological and pathophysiological processes in practically every organ, tissue and cell, including the vascular, renal, gastrointestinal and reproductive systems. Their activities are mediated through prostanoid-specific receptors and intracellular signalling pathways, whilst their biosynthesis and action are blocked by nonsteroidal antiinflammatory drugs (NSAID). Isoprostanes are considered to be reliable markers of oxidant stress status and have been linked to inflammation, ischaemia-reperfusion, diabetes, cardiovascular disease, reproductive disorders and diabetes. (PMID: 16986207). C20H38O5 None None None 7849.09 4970.81 7227.92 4337.88 3956.52 6910.06 5206.98 6891.74 3598.25 4337.02 5768.48 3377.19 4418.42 5550.16 5419.17 5988.01 12976.9 5561.3 4098.26 7047.64 4794.41 3140.37 4577.68 5435.75 5940.01 5070.43 5180.3 4967.77 3484.34 7428.15 5476.02 3928.76 3449.26 3824.31 4275.62 4441.74 4159.44 2691.59 2951.19 4625.79 6770.37 4859.87 358.0480605_MZ 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate Un 1.0 None None None None 5-amino-1-(5-phospho-D-ribosyl) imidazole-4-carboxylate is an intermediate in purine metabolism. 5-amino-1-(5-phospho-D-ribosyl) imidazole-4-carboxylate is converted from aminoimidazole ribotide via phosphoribosylaminoimidazole carboxylase [EC: 4.1.1.21]. C9H14N3O9P, N5-Carboxyaminoimidazole ribonucleotide None None None 17782.0 17595.1 15659.6 9916.55 11496.0 15310.4 13861.4 16386.5 9969.14 8595.31 15243.1 11843.6 13644.6 14247.4 10702.5 15272.0 8853.2 19311.2 10469.0 14525.2 18716.4 11573.8 9628.56 16246.5 11397.3 11129.2 14293.3 13564.1 18123.9 14918.5 14364.6 10038.2 12052.1 9163.35 16242.0 14400.7 10572.4 10967.1 10048.1 14021.4 13480.6 15226.7 358.1292158_MZ 5-Hydroxytryptophol glucuronide Un 1.0 None None None None 5-Hydroxytryptophol glucuronide (GTOL) is the major excretion form of 5-hydroxytryptophol (5-HTOL), a minor serotonin metabolite under normal conditions. Because the concentration of 5-HTOL is markedly increased following consumption of alcohol, measurement of 5-HTOL is used as a sensitive biomarker for detection of recent alcohol intake. PMID: 15664340. 5-Hydroxytryptophol glucuronide provided higher diagnostic specificity and sensitivity than 5-hydroxytryptophol. PMID: 17112495. C16H21NO7 None None None 6570.62 6197.32 11615.0 8266.49 7417.24 8368.14 8155.14 7061.25 6441.51 6764.39 6979.06 8720.8 7109.95 6510.54 7442.06 7237.12 7633.48 6023.83 7006.04 8401.98 8546.4 7431.71 7716.53 7028.48 7519.77 6908.96 7594.83 6158.21 8249.73 7523.9 7351.11 6423.65 7686.95 5583.35 8718.43 9160.78 5679.44 7790.94 4922.91 7105.78 6715.41 6386.51 358.1909470_MZ 19-oic-deoxycorticosterone Un 1.0 None None None None 19-hydroxydeoxycorticosterone (19,21-dihydroxy-4-pregnen-3,20-dione), 19-oxo-deoxycorticosterone (21-hydroxy-4-pregnen-3,19,20-trione), and 19-oic-deoxycorticosterone (19-oic-21-hydroxy-4-pregnen-3,20-dione)are formed from precursor deoxycorticosterone by adrenal glands obtained from intact rats and from rats undergoing adrenal regeneration.rat adrenals have the enzymes required to convert deoxycorticosterone to 19-hydroxydeoxycorticosterone, 19-oxo-deoxycorticosterone, and 19-oic-deoxycorticosterone; however, rat adrenals do not convert deoxycorticosterone or any of the oxygenated metabolites to 19-nor-deoxycorticosterone (21-hydroxy-19-nor-4-pregnen-3,20-dione). It is possible, however, that 19-nor-deoxycorticosterone is formed at peripheral sites from the oxygenated deoxycorticosterone precursors. C21H27O5 None None None 5125.05 5040.07 5487.96 6396.67 4435.04 5430.54 5363.77 5449.89 5659.55 4693.65 5216.2 5500.36 3639.92 5281.46 5076.22 4727.26 7065.29 3051.46 4028.93 4660.71 5123.16 4093.55 4970.86 5226.92 4408.98 4351.69 4906.29 4671.91 4014.39 5723.32 4432.63 4264.35 3577.18 3718.74 5023.71 5356.1 4318.14 4102.26 3600.3 4935.09 3442.79 4715.19 358.2257003_MZ Kinetensin 1-3 Un 1.0 None None None None Kinetensin 1-3 is a fraction of Kinetensin with only Ile-Ala-Arg peptide chain. Kinetensin is a nonapeptide, originally isolated from pepsin-treated plasma that shares some sequence homology with the C-terminal end of neurotensin, serum albumin and angiotensin. It is a potent histamine releaser in rodents and may serve as an inflammatory mediator. C15H31N6O4 None None None 2877.48 2527.04 2615.43 3089.63 2268.1 2543.09 3750.33 3638.56 2256.05 2238.86 2248.17 1810.84 2314.16 2581.12 2721.17 2467.37 5124.32 2827.45 2063.27 3104.2 2322.33 1509.29 2352.89 2706.89 2514.89 2154.67 2330.48 2977.85 1515.85 3107.61 2683.98 2111.86 1545.35 2376.38 1697.11 2647.77 1566.01 1453.72 1458.85 2445.9 2967.25 2288.81 361.2034545_MZ Cortisol Un 1.0 None None None None Cortisol is a corticosteroid hormone produced by the adrenal cortex that is involved in the response to stress; The main glucocorticoid secreted by the adrenal cortex. Its synthetic counterpart is used, either as an injection or topically, in the treatment of inflammation, allergy, collagen diseases, asthma, adrenocortical deficiency, shock, and some neoplastic conditions. As an oral or injectable drug, cortisol is also known as hydrocortisone. It is used as an immunosuppressive drug, given by injection in the treatment of severe allergic reactions such as anaphylaxis and angioedema, in place of prednisolone in patients who need steroid treatment but cannot take oral medication, and peri-operatively in patients on long-term steroid treatment to prevent an Addisonian crisis. Cortisol or Hydrocortisone is a corticosteroid hormone produced by the adrenal cortex that is involved in the response to stress. It increases blood pressure, blood sugar levels, may cause infertility in women, and suppresses the immune system. Its synthetic counterpart (hydrocortisone) is used, either as an injection or topically, in the treatment of inflammation, allergy, collagen diseases, asthma, adrenocortical deficiency, shock, and some neoplastic conditions. Cortisol is synthesized from pregnenolone. The amount of cortisol present in the serum undergoes diurnal variation, with the highest levels present in the early morning, and lower levels in the evening, several hours after the onset of sleep. Cortisol is a corticosteroid hormone produced by the adrenal cortex that is involved in the response to stress; it increases blood pressure, blood sugar levels, may cause infertility in women, and suppresses the immune system. Synthetic cortisol, also known as hydrocortisone, is used as a drug mainly to fight allergies and inflammation; it increases blood pressure, blood sugar levels, may cause infertility in women, and suppresses the immune system. Synthetic cortisol, also known as hydrocortisone, is used as a drug mainly to fight allergies and inflammation. C21H30O5, 18-Hydroxycorticosterone, 17a,21-Dihydroxy-5b-pregnane-3,11,20-trione None None None 35176.1 11771.8 15507.3 26037.5 76876.2 43709.2 37153.1 29632.6 68889.4 28581.2 29004.0 22458.4 10417.1 16210.4 55151.0 40759.8 19440.7 22505.8 12993.5 29797.9 23194.4 25789.3 11484.8 12972.4 15882.6 25804.7 18474.4 21598.6 21726.6 17253.1 14450.4 10545.9 46723.7 12188.1 26733.4 35694.7 8998.66 22169.2 10568.8 19338.5 31854.2 30046.0 361.3106681_MZ Monoacylglyceride Phosphate with formula C21H42O3 Un 1.0 None None None None 1-(1Z-octadecenyl)-sn-glycerol is an ether lipid. Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. C21H42O3 None None None 987.924 1099.34 950.291 1090.18 1290.64 1118.78 1093.48 1157.9 1095.59 1054.25 1282.06 1360.43 862.205 1341.33 1118.44 1025.24 1120.18 1307.08 907.29 1090.77 1138.98 963.624 1219.82 1090.12 1036.37 1163.99 994.252 1338.33 1023.87 1193.17 864.403 767.543 1236.07 969.687 1010.91 1017.69 990.466 1178.66 1011.45 1089.2 743.807 978.508 362.0497559_MZ Guanosine monophosphate Un 1.0 None None None None Guanosine 5'-monophosphate. A guanine nucleotide containing one phosphate group esterified to the sugar moiety and found widely in nature. C10H14N5O8P, 8-Oxo-dGMP None None None 239162.0 234255.0 342466.0 409191.0 353182.0 235333.0 390642.0 284236.0 392546.0 285606.0 231346.0 282367.0 366557.0 233195.0 389302.0 182613.0 329528.0 292697.0 344314.0 268893.0 259370.0 334407.0 314079.0 222765.0 409048.0 339883.0 330980.0 263165.0 311955.0 236864.0 220272.0 198578.0 250674.0 317867.0 330237.0 272131.0 421605.0 325381.0 275533.0 308205.0 370841.0 300648.0 363.0331970_MZ Xanthylic acid Un 1.0 None None None None Xanthylic acid is an important metabolic intermediate in the Purine Metabolism, and is a product or substrate of the enzymes Inosine monophosphate dehydrogenase (EC 1.1.1.205), Hypoxanthine phosphoribosyltransferase (EC 2.4.2.8), Xanthine phosphoribosyltransferase (EC 2.4.2.22), 5'-Ribonucleotide phosphohydrolase (EC 3.1.3.5), Ap4A hydrolase (EC 3.6.1.17), Nucleoside-triphosphate diphosphatase (EC 3.6.1.19), Phosphoribosylamine-glycine ligase (EC 6.3.4.1), and glutamine amidotransferase (EC 6.3.5.2). (KEGG) Xanthylic acid can also be used in quantitative measurements of the Inosine monophosphate dehydrogenase enzyme activities in purine metabolism. This measurement is important for optimal thiopurine therapy for children with acute lymphoblastic leukaemia (ALL). (PMID: 16725387). C10H13N4O9P None None None 7556.03 9095.84 9252.13 5127.92 8453.41 9467.02 8803.06 7907.95 8971.72 8295.37 8490.93 9950.6 6230.71 8381.59 9713.8 6521.39 6335.67 6826.55 8166.73 7493.43 8105.77 9075.35 7678.08 8486.15 8018.88 9983.7 8580.71 7469.94 8865.2 10165.7 7023.05 5658.0 9447.4 6510.34 8805.67 7583.82 9660.16 9155.89 5541.32 7958.84 6524.1 6862.37 363.1804711_MZ 12-oxo-10,11-dihydro-20-COOH-LTB4 Un 1.0 None None None None 12-oxo-10,11-dihydro-20-COOH-LTB4 is formed when leukotriene B4 (LTB4) is metabolized by beta-oxidation. LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by w-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the w-carboxy position and after CoA ester formation. (PMID: 8632343, 9667737). Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways. C20H28O6 None None None 20890.8 12006.6 18854.2 9306.36 9125.82 16877.3 11346.9 10599.2 7788.6 10070.8 10783.1 10449.3 11219.2 12607.2 10545.9 14417.7 18150.9 16008.9 7948.23 19713.8 9082.65 8676.13 9075.99 9821.82 12323.7 11283.3 11782.0 11072.4 12594.4 16625.8 9906.66 7947.16 9512.65 8280.71 10758.3 9491.9 10593.9 7412.22 3895.91 9515.22 17001.4 9326.43 363.2370483_MZ 16(17)-EpDPE Un 1.0 None None None None 16(17)-EpETE is the DHA homolog of 14(15)-EpETrE, derived via epoxidation of the 16,17-double bond of docosahexaenoic acid (DHA). The EDHF (endothelium-derived hyperpolarizing factor) activity of 16(17)-EpDPE has not yet been determined. The epoxygenase metabolites of DHA have also been detected in a murine inflammation model (PMID: 12391014). EDHF is an unidentified mediator released from vascular endothelial cells in response to acetylcholine and bradykinin which is distinct from the NOS- (nitric oxide) and COX-derived (prostacyclin) vasodilators (PMID: 9504399, 10519554). Cytochrome P450 (CYP450) metabolism of polyunsaturated fatty acids produces epoxides such as 14(15)-EpETrE which are prime candidates for the actual active mediator (PMID: 9401962). However, the CYP450 metabolites of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) have been little studied relative to arachidonate epoxygenase metabolites. C22H32O3, 17-HDoHE None None None 5196.69 5687.69 4836.42 6001.26 5966.78 4521.96 6214.95 6069.8 6122.75 5061.3 5401.72 6407.2 4301.15 5738.89 5003.73 4003.97 8316.1 5520.97 3867.68 5922.27 4790.43 4281.33 5468.58 5237.8 4645.06 4774.96 4383.06 5875.55 4202.85 5442.22 4555.74 3658.22 5385.46 4280.49 4536.03 4963.23 4205.59 5005.31 3671.63 4897.43 5051.03 5644.29 363.2891464_MZ 2-Arachidonyl Glycerol ether Un 1.0 None None None None C23H40O3 None None None 2403.86 2274.73 1718.36 1683.63 1644.86 2726.73 2402.2 2819.87 1721.75 1908.68 2213.01 1855.08 1286.99 2111.01 2516.23 2058.21 4157.32 2138.23 1704.53 2472.04 1999.44 1380.92 1924.08 2232.95 1855.13 1364.31 1828.34 2503.16 1455.17 2610.67 1898.98 1679.23 1672.21 2652.91 1537.05 1987.75 1425.11 1259.48 1652.78 1756.4 1616.11 1881.93 363.3263954_MZ Monoacylglyceride with formula C21H44O3 Un 1.0 None None None None C21H44O3 None None None 1789.47 1738.98 1280.93 1355.3 1234.08 1212.45 1523.45 1698.09 1304.27 1489.85 1568.36 1535.83 1514.97 1861.37 995.378 1468.69 2064.22 1761.7 1087.62 1651.35 1408.59 1122.42 1483.65 1376.87 1148.7 1363.84 1105.8 2007.6 1180.24 1508.25 1150.53 816.843 1511.11 1310.85 1434.93 1375.3 1245.84 1311.57 1361.48 1280.81 1193.1 1338.36 365.1956454_MZ 20-Carboxyleukotriene B4 Un 1.0 None None None None 20-Carboxyleukotriene B4 is an omega-oxidized metabolite of leukotriene B4 (LTB4). Neutrophil microsomes are known to oxidize 20-hydroxy-LTB4 (20-OH-LTB4) to its 20-oxo and 20-carboxy derivatives in the presence of NADPH. This activity has been ascribed to LTB4 omega-hydroxylase (cytochrome P-450LTB omega). Leukotriene B4 release from polymorphonuclear granulocytes of severely burned patients was reduced as compared to healthy donor cells. This decrease is due to an enhanced conversion of LTB4 into the 20-hydroxy- and 20-carboxy-metabolites and further to a decreased LTB4-synthesis. LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by w-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the w-carboxy position and after CoA ester formation. Other specific pathways of leukotriene metabolism include the 12-hydroxydehydrogenase/ 15-oxo-prostaglandin-13-reductase that form a series of conjugated diene metabolites that have been observed to be excreted into human urine. Metabolism of LTC4 occurs by sequential peptide cleavage reactions involving a gamma-glutamyl transpeptidase that forms LTD4 (leukotriene D4) and a membrane-bound dipeptidase that converts LTD4 into LTE4 (leukotriene E4) before w-oxidation. These metabolic transformations of the primary leukotrienes are critical for termination of their biological activity, and defects in expression of participating enzymes may be involved in specific genetic disease. (PMID 17623009, 7633595, 2155225, 3039534)Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways. C20H30O6, 20-COOH-10_11-dihydro-LTB4 None None None 15242.0 13848.3 15877.8 14826.6 12315.6 17230.8 15518.9 14025.6 11371.5 11784.6 14156.4 13154.2 9536.7 13859.6 17502.4 16725.2 23674.1 10393.5 9851.47 17577.8 12800.3 11737.9 12747.1 16372.5 15643.2 11493.3 16887.9 12833.1 13112.4 16237.8 13681.1 9849.25 12118.9 10341.1 12692.1 11929.8 9614.48 10680.5 5876.01 13836.6 15447.1 14143.0 365.2328890_MZ Tetrahydrocortisol Un 1.0 None None None None Tetrahydrocortisol is the most powerful natural angiostatic steroid. It is involved in C21-Steroid hormone metabolism pathway (KEGG). C21H34O5, 3b-Allotetrahydrocortisol, 5a-Tetrahydrocortisol, Cortolone, Beta-Cortolone None None None 14645.8 12522.8 14772.0 15926.8 48903.8 10986.1 27843.0 17307.2 44157.0 23499.0 11275.7 13259.6 15506.0 20054.0 30704.6 15015.5 24423.9 30588.9 14074.0 38096.7 18862.3 19790.6 15821.3 19279.0 19233.7 17283.6 19926.8 16715.7 20383.8 17726.1 18550.5 12081.1 37910.2 11325.3 24740.2 20573.5 10663.9 12679.7 10718.2 21781.6 36188.8 32599.2 365.3417249_MZ Nervonic acid Un 1.0 None None None None Nervonic acid is a long chain unsaturated fatty acid that is enriched in sphingomyelin. It consists of choline, sphingosine, phosphoric acid, and fatty acid. Nervonic acid may enhance the brain functions and prevent demyelination (Chemical Land21). Research shows that there is negative relationship between nervonic acid and obesity-related risk factors (PMID: 16394593). Demyelination in adrenoleukodystrophy (ALD) is associated with an accumulation of very long chain saturated fatty acids stemming from a genetic defect in the peroxisomal beta oxidation system responsible for the chain shortening of these fatty acids. Sphingolipids from post mortem ALD brain have decreased levels of nervonic acid, 24:1(n-9), and increased levels of stearic acid, 18:0. (PMID: 8072429). C24H46O2 None None None 4797.04 4316.41 4385.94 4845.04 5005.02 3806.94 5754.93 6554.03 4665.37 4180.38 4852.86 4891.03 6691.27 8085.0 3766.21 3658.12 6403.57 7727.69 3659.97 5677.75 4164.37 3328.17 5256.23 4239.19 4977.16 5419.86 4023.5 5795.23 3266.4 4405.3 4183.29 3273.31 5130.43 3715.42 3301.57 4101.71 4514.7 4404.2 4660.09 4070.02 5820.97 4772.48 366.2638242_MZ 3_ 5-Tetradecadiencarnitine Un 1.0 None None None None C21H37NO4 None None None 1763.94 1808.11 1346.39 1011.26 2083.78 2455.59 1816.13 2054.59 1907.71 1790.54 1574.89 1495.03 1558.5 1721.39 2001.98 1960.39 2405.41 2349.32 1426.54 2590.33 1385.08 1404.4 1771.32 1785.69 1563.5 1306.04 1257.17 2012.36 1397.56 2210.4 1710.56 1451.91 1531.58 1392.12 1266.11 1708.71 1239.46 1374.71 993.35 1652.9 1584.17 1584.71 367.0176252_MZ Orotidylic acid Un 1.0 None None None None Orotidylic acid (OMP), is a pyrimidine nucleotide which is the last intermediate in the biosynthesis of uridine monophosphate. Decarboxylation by Orotidylate decarboxylase affords Uridine 5'-phosphate which is the route to Uridine and its derivatives de novo and consequently one of the most important processes in nucleic acid synthesis (Dictionary of Organic Compounds). In humans, the enzyme UMP synthase converts OMP into uridine 5'- monophosphate. If UMP synthase is defective, orotic aciduria can result. (Wikipedia). C10H13N2O11P None None None 43229.9 31633.3 23518.0 19262.9 22023.8 39285.6 35034.8 29993.4 13971.0 21364.6 21571.5 13185.4 51442.8 21479.8 18017.3 57230.7 21844.1 52973.8 25388.9 41937.0 37520.2 11211.9 25964.1 29451.1 29513.9 18422.1 32261.8 30754.0 18689.7 22783.3 40895.6 34593.9 15086.5 21133.8 17479.0 28733.9 17682.0 13726.6 18429.0 24635.0 41757.6 36184.8 367.1038923_MZ Riboflavin reduced Un 1.0 None None None None Riboflavin reduced is an intermediate in the metabolism of Porphyrin and chlorophyll. It is a substrate for Flavin reductase. C15H16N4O6 None None None 16820.4 13845.6 19689.6 7729.55 8602.65 35827.1 11327.9 7407.72 10872.7 21082.0 14997.4 13869.6 11871.5 11395.9 14250.4 29324.5 8109.76 10522.8 10568.2 12532.2 14388.4 21186.2 16546.1 13418.2 10199.0 13729.6 10066.7 16865.2 24784.5 17557.9 9448.18 18915.3 8203.45 8554.31 27461.1 18839.5 9369.69 9858.8 9999.99 14235.6 7628.73 11201.4 367.2119523_MZ 19-Hydroxy-PGE2 Un 1.0 None None None None 19-Hydroxy-PGE2 is a derivative of PGE2. Both 19-Hydroxy-PGE1 and 19-hydroxy-PGE2 are formed from PGE1 and PGE2 by prostaglandin 19-hydroxylase, a cytochrome P-450 enzyme, in seminal vesicles (PMID: 3196735). 19-Hydroxy-PGE2 is a selective prostanoid EP2-receptor agonist; it doesn't stimulate FP-receptors, and is devoid of activity on thromboxane A2, prostaglandin D2 and prostacyclin sensitive receptors. 19-OH PGE2 is formed in large quantities from PGE2 in human seminal plasma. PGE2 is the most common and most biologically active of the mammalian prostaglandins. It has important effects in labour and also stimulates osteoblasts to release factors which stimulate bone resorption by osteoclasts (a type of bone cell that removes bone tissue by removing the bone's mineralized matrix). (PMID: 16978535, 8248550, 817207). Dinoprostone is a naturally occurring prostaglandin E2 (PGE2) and the most common and most biologically active of the mammalian prostaglandins. It has important effects in labour and also stimulates osteoblasts to release factors which stimulate bone resorption by osteoclasts (a type of bone cell that removes bone tissue by removing the bone's mineralized matrix). PGE2 has been shown to increase vasodilation and cAMP production, to enhance the effects of bradykinin and histamine, to induce uterine contractions and to activate platelet aggregation. PGE2 is also responsible for maintaining the open passageway of the fetal ductus arteriosus; decreasing T-cell proliferation and lymphocyte migration and activating the secretion of IL-1alpha and IL-2. PGE2 exhibits both pro- and anti-inflammatory effects, particularly on dendritic cells (DC). Depending on the nature of maturation signals, PGE2 has different and sometimes opposite effects on DC biology. PGE2 exerts an inhibitory action, reducing the maturation of DC and their ability to present antigen. PGE2 has also been shown to stimulate DC and promote IL-12 production when given in combination with TNF-alpha. PGE2 is an environmentally bioactive substance. Its action is prolonged and sustained by other factors especially IL-10. It modulates the activities of professional DC by acting on their differentiation, maturation and their ability to secrete cytokines. PGE2 is a potent inducer of IL-10 in bone marrow-derived DC (BM-DC), and PGE2-induced IL-10 is a key regulator of the BM-DC pro-inflammatory phenotype. (PMID: 16978535)Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways. C20H32O6, 6,15-Diketo,13,14-dihydro-PGF1a, Prostaglandin G2, 20-Hydroxy-PGE2, 6-Ketoprostaglandin E1, 11-Dehydro-thromboxane B2, Thromboxane B3, 5(6)-Epoxy Prostaglandin E1 None None None 14479.5 12421.2 21086.5 15964.5 15700.0 20596.5 18741.8 15716.7 11859.1 13745.9 16327.3 17200.0 13805.6 14996.6 17911.3 19768.4 24555.8 15577.1 10285.7 22820.6 13260.0 11818.2 15917.2 14008.4 19581.2 12498.4 16095.9 13170.9 16471.3 16607.6 16342.9 11858.8 15205.5 12616.8 12391.5 12007.1 12719.5 15695.5 6588.66 16823.8 26972.3 12289.9 367.3572055_MZ Tetracosanoic acid Un 1.0 None None None None Lignoceric acid, also tetracosanoic acid, is a normal carboxylic acid, a very long chain fatty acid (VLCFA). Very long chain fatty acids (VLCFAs) are exclusively oxidized in peroxisomes and their levels are significantly increased in tissues of patients with peroxisomal disorders. (PMID 15565636). C24H48O2 None None None 25739.1 29166.8 24073.5 25703.5 25591.6 22610.6 28457.7 31534.4 23222.2 24546.0 28421.9 26134.3 26143.9 28089.3 22420.9 22976.5 28916.2 43893.4 23127.5 30844.5 23314.7 22267.2 24293.3 26946.2 25067.7 23661.4 22932.4 31028.9 22529.6 28738.4 23760.2 22017.8 25160.2 26385.7 22642.2 25845.4 21153.3 25795.2 27041.5 25216.5 21896.2 24317.8 369.2064388_MZ Prostaglandin E3 Un 1.0 None None None None Prostaglandin E3 is from the cyclooxygenase metabolism of eicosapentaenoic acid.Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways. C20H30O5, 8-iso-15-keto-PGE2, Prostaglandin D3, 15-Keto-prostaglandin E2, Resolvin E1 None None None 11984.1 13389.2 12225.6 15755.7 13916.8 13888.0 26443.1 17403.6 8683.81 14220.7 15900.9 3649.02 10137.4 17380.1 13688.9 12297.0 18971.5 7784.4 10965.6 19241.8 10399.4 3459.88 14285.5 9606.52 15058.8 3481.13 11450.8 8641.66 3168.99 16006.4 14726.7 12173.7 3050.31 12731.0 3390.44 11030.3 6870.46 2847.37 5488.11 12017.7 11094.1 9281.18 371.0322032_MZ Petunidin Un 1.0 None None None None Petunidin is an anthocyanin. Anthocyanins are water soluble pigments belonging to the flavonoids compound family involved in nature in a wide range of functions such as flowers, fruits, and seeds pigmentation to attract pollinators, to disperse seeds, to protect against UV light damage, and in plant defense to protect against pathogen attack. Because anthocyanins impart much of the color and flavor of fruits and vegetables, they are usually components of the human diet and are not only considered exclusively as food products but also as therapeutic agents; in fact, anthocyanins have been suggested to protect against oxidative stress, coronary heart diseases, certain cancers, and other age-related diseases. At least part of these presumed health-promoting features can be attributed to the antioxidant properties of these compounds whose chemical structure appears ideal for free radical scavenging. (PMID: 16277406). C16H13ClO7 None None None 8498.26 7650.6 8372.0 6524.68 7882.38 10788.8 8493.42 7231.49 7610.94 8859.59 7554.08 8388.47 9459.24 7180.98 8303.4 11680.1 8018.76 10305.4 8997.51 8528.69 8414.38 8453.01 8057.46 8060.77 7966.98 8693.96 8300.16 8229.52 7885.21 9187.28 8644.37 9156.3 7829.3 7252.28 8514.02 10122.5 7795.69 8178.1 5737.44 8720.12 8893.6 8583.2 373.2013602_MZ 11beta,20-Dihydroxy-3-oxopregn-4-en-21-oic acid Un 1.0 None None None None 11b,20-dihydroxy-3-oxopregn-4-en-21-oic acid or DHOPA is a major metabolite of corticosterone that is typically elevated in the liver. The in vivo conversion of corticosterone to DHOPA is thought to proceed via the aldehyde intermediate 11b-hydroxy-3,20-dioxopregn-4-en-21-al. Cytochrome P450 3A4 (CYP3A4), is known to convert corticosterone to the gem-diol form of the aldehyde. Because CYP3A4 is highly abundant in the liver, the conversion of corticosterone to its aldehyde presumably occurs readily, and the formation of DHOPA by isomerization of the aldehyde. DHOPA has also been identified as a biomarker that is elevated (50 X) in animals that have been treated with PPARalpha agonists. Peroxisome proliferator-activated receptor alpha (PPARalpha) is a nuclear receptor with manifold effects on intermediary metabolism (PMID: 17550978). C22H30O5 None None None 9735.07 15932.9 13092.5 17749.2 19457.2 19246.0 18816.6 12735.6 14405.9 14448.9 19956.2 14112.5 5179.8 17019.4 17011.8 15353.9 12852.8 4208.23 10143.3 13160.9 12526.6 10683.9 14897.0 10718.6 13998.8 10359.0 13634.9 10459.4 8558.65 16393.7 13356.6 12880.4 10243.8 10953.6 9589.1 13116.8 8610.65 12585.5 4885.74 14379.3 7771.14 9435.47 373.2754081_MZ 3b-Hydroxy-5-cholenoic acid Un 1.0 None None None None 3b-Hydroxy-5-cholenoic acid is a monohydroxy bile acid of endogenous origin. It is found in biologic fluids beginning in fetal life. (PMID 5567561; 4803245; 93138) Large amounts of 3 beta-hydroxy-5-cholenoic acid could be found in children with the syndrome of hepatic ductular hypoplasia (PMID 3987031). C24H38O3 None None None 10616.0 7376.54 7974.77 13719.8 8107.79 80838.5 36456.5 13230.9 17571.0 17521.1 9826.1 9082.37 7628.01 24655.6 56817.7 11078.9 10429.1 11751.1 28300.4 22793.9 10717.7 8721.48 10034.3 9832.86 9476.93 9937.44 9318.25 12631.6 9608.94 11103.6 14685.3 4721.66 8902.39 6562.92 7266.36 39557.6 7439.64 8672.16 5387.37 10530.2 45765.6 36698.1 374.2620036_MZ 6,9,12,15,18,21-Tetracosahexaenoic acid Un 1.0 None None None None 6,9,12,15,18,21-Tetracosahexaenoic acid (24:6n-3) is one of the n-3 PUFA and is a very long chain fatty acid. Distribution of 24:6n-3 in marine organisms was investigated by several researchers. Takagi et al. reported relatively high contents of 24:6n-3 in sea lilies and brittle stars (4–10% of total fatty acids). High 24:6n-3 content was also found in marine coelenterates. In some edible fishes, 24:6n-3 was detected at significant levels (0–10% of total fatty acids).The existence of 24:6n-3 in mammalian tissues was reported with other very long chain fatty acids in the spermatozoa,the retina, and the brain. Voss et al. reported that 24:6n-3 is formed as an intermediate in the metabolic pathway from 20:5n-3 to 22:6n-3 in rat liver. Even though 24:6n-3 is a PUFA existing in fish and mammalian species, physiological functions of 24:6n-3 have not been studied. As functions to be studied, anti-inflammatory and antiallergic. effects of 24:6n-3 are noteworthy because these events are known to be closely related to the unsaturated fatty acid metabolism such as in the arachidonic acid cascade, and 20:5n-3 and 22:6n-3 were reported to suppress inflammatory actions by influencing arachidonic acid metabolism.s24:6n-3 could inhibit the antigen-stimulated production of LT-related compounds as well as other n-3 polyunsaturated fatty acids (PUFA) such as eicosapentaenoic. acid (20:5n-3) and docosahexaenoic acid (22:6n-3), which are major n-3 PUFA in fish oils; 24:6n-3 was also shown to reduce the histamine content in MC/9 cells at 25 uM (27% reduction from the control), and the effect was diminished with increase of the fatty acid concentration (up to 100 uM). These two n-3 PUFA, 20:5n-3 and 22:6n-3, also reduced the histamine content (16 and 20% reduction at 25 μM, respectively), whereas arachidonic acid (20:4n-6) increased it (18% increase at 25 μM). C24H35O2 None None None 6403.73 2554.56 5628.95 2606.98 2193.75 7568.27 5894.26 2839.62 2810.1 2539.39 4371.77 3879.1 3313.56 5201.7 2831.4 3459.6 6770.67 5005.8 3190.87 4733.44 4167.7 6357.79 6987.36 4562.37 6280.61 7587.39 4046.27 3993.61 5584.33 4706.77 7767.29 2578.08 4471.86 3139.59 4994.87 3901.97 2979.83 3802.73 621.945 4580.39 11285.7 5111.85 375.1301259_MZ Riboflavin Un 1.0 None None None None Riboflavin or vitamin B2 is an easily absorbed, water-soluble micronutrient with a key role in maintaining human health. Like the other B vitamins, it supports energy production by aiding in the metabolizing of fats, carbohydrates, and proteins. Vitamin B2 is also required for red blood cell formation and respiration, antibody production, and for regulating human growth and reproduction. It is essential for healthy skin, nails, hair growth and general good health, including regulating thyroid activity. Riboflavin is found in milk, eggs, malted barley, liver, kidney, heart, and leafy vegetables. Riboflavin is yellow or orange-yellow in color and in addition to being used as a food coloring it is also used to fortify some foods. It can be found in baby foods, breakfast cereals, sauces, processed cheese, fruit drinks and vitamin-enriched milk products. The richest natural source is yeast. It occurs in the free form only in the retina of the eye, in whey, and in urine; its principal forms in tissues and cells are as flavin mononucleotide and flavin adenine dinucleotide. C17H20N4O6 None None None 6047.45 5530.25 6953.03 6709.64 6174.64 7129.22 6562.17 6652.8 4900.78 6724.26 5383.0 5876.73 4292.23 5273.09 7406.61 8488.18 8667.0 4035.2 5906.18 5876.77 5207.08 4544.42 6852.86 5096.61 5958.67 4631.59 6918.75 5803.91 5259.6 6830.99 6162.53 8150.81 4589.79 4596.41 5538.92 5242.02 4576.4 5900.75 3271.56 6331.15 5420.77 4900.28 375.2191795_MZ Resolvin D2 Un 1.0 None None None None Resolvin D2 is an autacoid resolvin. Autacoids are chemical mediators including the families of resolvins and protectins, defined by their potent bioactions and novel chemical structures. The bioactive local mediators, or autacoids, that require enzymatic generation from the omega-3 essential fatty acid EPA were first identified in resolving inflammatory exudates in vivo and carry potent stereoselective biological actions. Resolvins of the E (RvE) series are derived from eicosapentaenoic acid (EPA). Those derived from docosahexaenoic acid (DHA) were termed resolvins of the D series, for example resolvin D1 (RvD1).Resolvins and protectins have specific stereoselective actions which evoke biological actions in the nanogram range in vivo and are natural exudate products. Resolvins and protectins as distinct chemical families join the lipoxins as potent agonists of endogenous anti-inflammation and are proresolving chemical mediators of interest in human disease as potential new approaches to treatment. The term resolvins (resolution-phase interaction products) was first introduced to signify that these new structures were endogenous mediators, biosynthesized in the resolution phase of inflammatory exudates, possessing very potent anti-inflammatory and immunoregulatory actions. These actions include reducing neutrophil traffic, regulating cytokine and reactive oxygen species, and lowering the magnitude of the response. In recent years, investigators have recognized inflammation as playing a key role in many prevalent diseases not previously considered to be of inflammatory etiology. These include Alzheimer's disease, cardiovascular disease, and cancer, which now join those well-appreciated inflammatory disorders such as arthritis and periodontal disease. Identifying the molecular mechanism(s) that underlie the many reports of the benefits of dietary omega-3 PUFAs remains an important challenge for nutrition and medicine. Thus, that these new mediator families, resolvins and protectins, are biosynthesized from EPA and DHA, act locally, and possess potent, novel bioactions is of interest to researchers. (PMID: 17090225). C22H32O5, Resolvin D1, 11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid None None None 7581.66 9717.4 8031.16 12722.8 9199.68 12582.0 9347.57 8676.15 8816.34 8035.43 10574.9 9817.55 3534.34 8511.71 9924.39 9437.5 9255.84 5151.3 6075.19 7172.84 8252.23 6191.84 8649.95 8806.99 7593.99 7315.62 8861.1 6316.93 6054.19 10121.8 8008.54 7467.71 7555.83 6879.39 7165.61 8003.59 6211.95 7476.13 5234.35 8184.67 5317.92 7543.69 375.2910198_MZ Allolithocholic acid Un 1.0 None None None None Allolithocholic acid is a bile acid present in normal serum and feces, with a tendency to be at higher concentrations in patients with colon cancer, particularly in men (PMID 16548228). A bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487, 16037564, 12576301, 11907135). C24H40O3, Isoallolithocholic acid, Isolithocholic acid, Lithocholic acid, 12b-Hydroxy-5b-cholanoic acid, 7a-Hydroxy-5b-cholanic acid None None None 13703.4 9230.09 9923.62 10600.3 17058.9 122766.0 24900.5 14965.0 20991.9 24416.2 15525.3 9857.69 16527.6 41090.5 86816.0 10452.4 9656.32 27240.9 27262.8 32374.7 14153.5 10576.4 11357.9 17327.5 14040.3 11934.0 12327.0 17040.8 10757.4 11741.9 14953.0 7357.01 18186.0 9337.58 7736.89 65409.5 12489.4 9922.25 12139.5 12567.5 71376.7 59988.0 376.1168964_MZ Kinetin-7-N-glucoside Un 1.0 None None None None Kinetin-7-N-glucoside is the product of the reaction between kinetin and UDP-D-glucose, with UDP as a co-product. The reaction is catalyzed by a UDP glycosyltransferase. C16H19N5O6, Kinetin-9-N-glucoside None None None 19799.3 22652.6 46981.7 18913.1 30323.1 24966.7 26670.5 28229.6 16841.2 17154.1 18544.3 44925.9 24653.8 19147.6 31343.4 44974.4 23492.3 30531.7 31015.4 23854.1 18019.0 26713.8 16343.0 19062.9 25090.8 31145.4 39334.8 30485.0 23414.5 18459.3 33609.5 27142.6 33324.0 19883.0 35234.9 18961.4 18022.1 30610.3 14929.4 23026.5 19402.3 22217.0 377.1374727_MZ 2-Phenylaminoadenosine Un 1.0 None None None None Selective A2 adenosine receptor agonist; potent coronary vasodilator; weak inhibitor of adenosine uptake by rat cerebral cortical synaptosomes; used as a vasodilator agent; is a potent anti-inflammatory agent, acting at its four G protein coupled receptors. Topical treatment of adenosine to foot wounds in diabetes mellitus has been shown in lab animals to drastically increase tissue repair and reconstruction. Topical administration of adenosine for use in wound healing deficiencies and diabetes mellitus in humans is currently under clinical investigation. Adenosine is a nucleoside comprised of adenine attached to a ribose (ribofuranose) moiety via a beta-N9-glycosidic bond. C16H18N6O4 None None None 12180.2 7311.21 14888.2 14489.1 7015.51 14261.3 10652.1 14456.8 6647.96 11917.8 7481.91 9384.89 10661.7 8745.81 9977.71 12418.6 14973.0 5608.38 11483.7 10176.6 11931.2 9691.71 12322.8 10455.4 11604.5 10811.5 8410.56 11292.6 11445.5 14331.1 15289.6 14228.3 9272.13 9868.22 13147.6 17109.3 10399.7 11354.5 5899.46 11848.9 6156.1 9898.26 377.1958660_MZ 18-Hydroxycortisol Un 1.0 None None None None 18-Hydroxycortisol is a derivative of cortIsolated It may be synthesized by zona fasciculata 11-beta hydroxylase in normal human adrenal cortex. (PMID 15356073; 1751390) Overproduction of 18-hydroxycortisol is an aid in the detection of Glucocorticoid-remediable aldosteronism which is an inherited form of mineralocorticoid excess associated with moderate overproduction of aldosterone, in which biochemical and clinical remission is dramatically induced by small amounts of glucocorticoids.(PMID: 1879399). C21H30O6 None None None 33166.5 21626.3 29268.9 17886.3 19120.0 28662.8 22958.3 18906.9 17131.9 20015.9 18450.1 17942.4 20987.7 22095.0 21566.6 20128.9 29373.2 30856.4 15937.5 40095.6 17731.8 19831.2 17120.1 19593.3 20714.9 18939.6 19934.7 23285.9 20233.4 26897.8 17283.4 15547.0 23813.3 17112.3 18363.9 21036.4 16723.6 12958.0 10651.4 17579.2 33409.7 19524.4 377.3038769_MZ Monoacylglyceride with formula C21H42O4 Un 1.0 None None None None MG(0:0/18:0/0:0) is a monoacylglyceride. A monoglyceride, more correctly known as a monoacylglycerol, is a glyceride consisting of one fatty acid chain covalently bonded to a glycerol molecule through an ester linkage. Monoacylglycerol can be broadly divided into two groups; 1-monoacylglycerols (or 3-monoacylglycerols) and 2-monoacylglycerols, depending on the position of the ester bond on the glycerol moiety. Normally the 1-/3-isomers are not distinguished from each other and are termed 'alpha-monoacylglycerols', while the 2-isomers are beta-monoacylglycerols. Monoacylglycerols are formed biochemically via release of a fatty acid from diacylglycerol by diacylglycerol lipase or hormone sensitive lipase. Monoacylglycerols are broken down by monoacylglycerol lipase. They tend to be minor components only of most plant and animal tissues, and indeed would not be expected to accumulate because their strong detergent properties would have a disruptive effect on membranes. 2-Monoacylglycerols are a major end product of the intestinal digestion of dietary fats in animals via the enzyme pancreatic lipase. They are taken up directly by the intestinal cells and converted to triacylglycerols via the monoacylglycerol pathway before being transported in lymph to the liver. Mono- and Diglycerides are commonly added to commercial food products in small quantities. They act as emulsifiers, helping to mix ingredients such as oil and water that would not otherwise blend well. C21H42O4 None None None 16097.4 16483.1 10748.9 9591.53 11549.2 18311.9 12684.6 11224.6 12205.6 14554.8 20492.3 18541.3 6993.33 15082.3 11901.0 12426.8 14307.9 8290.76 10424.8 10666.6 13949.7 10352.9 16058.9 12348.4 11692.8 10960.5 11943.4 13784.8 9161.9 16165.2 10909.1 8291.94 11337.5 10039.6 10530.9 10984.3 11651.7 11447.4 9457.98 9925.18 10517.4 10149.0 378.0968719_MZ S-Lactoylglutathione Un 1.0 None None None None S-Lactoylglutathione is a substrate of lactoylglutathione lyase [EC 4.4.1.5] in pyruvate metabolism (KEGG). Another enzyme, glyoxalase I, synthesizes this compound by converting methylglyoxal and reduced glutathione to S-lactoylglutathione. S-D-lactoylglutathione can be hydrolysed by thiolesterases to reduced glutathione and D-lactate but also converted to N-D-lactoylcysteinylglycine and N-D-lactoylcysteine by gamma-glutamyl transferase and dipeptidase (PMID: 8632674). S-lactoylglutathione has also been shown to modulate microtubule assembly (PMID: 690442). C13H21N3O8S None None None 27351.8 28933.0 33942.4 21718.7 57440.2 33826.3 41250.0 49760.4 29805.2 29120.9 21864.3 25170.1 44537.2 22377.3 43692.6 68178.0 20641.3 54172.6 47457.2 62908.0 34435.5 15420.7 23347.5 24813.8 54911.3 27163.3 71325.7 29524.0 24120.3 31882.1 70294.9 44769.8 52484.9 26239.8 22850.5 38221.3 19823.2 23341.3 20931.1 30968.4 92315.8 40398.3 378.2139603_MZ Donepezil Un 1.0 None None None None Donepezil, marketed under the trade name Aricept (Eisai), is a centrally acting reversible acetyl cholinesterase inhibitor. Its main therapeutic use is in the treatment of Alzheimer's disease where it is used to increase cortical acetylcholine. It has an oral bioavailability of 100% and easily crosses the blood-brain barrier. Because it has a half life of about 70 hours, it can be taken once a day. Initial dose is 5 mg per day, which can be increased to 10 mg per day after an adjustment period of at least 4 weeks. Donepezil is a centrally acting reversible acetyl cholinesterase inhibitor. Its main therapeutic use is in the treatment of Alzheimer's disease where it is used to increase cortical acetylcholine. It is well absorbed in the gut with an oral bioavailability of 100% and easily crosses the blood-brain barrier. Because it has a half life of about 70 hours, it can be taken once a day. Currently, there is no definitive proof that use of donepezil or other similar agents alters the course or progression of Alzheimer's disease. However, 6-12 month controlled studies have shown modest benefits in cognition and/or behavior. Pilot studies have reported that donepezil therapy may potentially have effects on markers of disease progression, such as hippocampal volume. Therefore, many neurologists, psychiatrists, and primary care physicians use donepezil in patients with Alzheimer's disease. In 2005, the UK National Institute for Clinical Excellence (NICE) withdrew its recommendation for use of the drug for mild-to-moderate AD, on the basis that there is no significant improvement in functional outcome; Currently, there is no definitive proof that use of donepezil or other similar agents alters the course or progression of Alzheimer's disease. However, 6-12 month controlled studies have shown modest benefits in cognition and/or behavior. Pilot studies have reported that donepezil therapy may potentially have effects on markers of disease progression, such as hippocampal volume. Therefore, many neurologists, psychiatrists, and primary care physicians use donepezil in patients with Alzheimer's disease. In 2005, the UK National Institute for Clinical Excellence (NICE) withdrew its recommendation for use of the drug for mild-to-moderate AD, on the basis that there is no significant improvement in functional outcome; of quality of life or of behavioral symptoms. However, NICE revised its guidelines to suggest that donepezil be used in moderate stage patients for whom the evidence is strongest. While the drug is currently indicated for mild to moderate Alzheimer's, there is also evidence from 2 trials that it may be effective for moderate to severe disease. An example of this is a Karolinska Institute paper published in The Lancet in early 2006, which states that donepezil improves cognitive function even in patients with severe Alzheimer's disease symptoms. of quality of life or of behavioral symptoms. However, NICE revised its guidelines to suggest that donepezil be used in moderate stage patients for whom the evidence is strongest. While the drug is currently indicated for mild to moderate Alzheimer's, there is also evidence from 2 trials that it may be effective for moderate to severe disease. An example of this is a Karolinska Institute paper published in The Lancet in early 2006, which states that donepezil improves cognitive function even in patients with severe Alzheimer's disease symptoms. C24H29NO3 None None None 4243.2 3460.46 2248.72 3309.42 2106.27 3129.16 2441.1 2072.96 2678.22 2577.32 2442.02 1993.82 1696.56 3328.71 2205.56 2431.28 2850.25 2101.26 1731.41 2782.71 2860.95 1881.29 2440.23 3765.77 2438.76 1762.8 2007.56 2303.62 1856.62 4325.01 2052.4 2258.59 1650.8 2268.5 1905.18 3501.65 2212.38 1516.6 1175.98 3100.82 2397.09 2509.04 378.2359582_MZ Sphingosine 1-phosphate Un 1.0 None None None None Sphingosine 1-phosphate (S1P) is a phosphorylated sphingolipid metabolite with potent bioactive actions in the Sphingolipid metabolism, Calcium signaling pathway and Neuroactive ligand-receptor interaction. Generated by sphingosine kinases and ceramide kinase, S1P control numerous aspects of cell physiology, including cell survival and mammalian inflammatory responses. S1P is involved in cyclooxygenase-2 induction (COX-2), and regulate production of eicosanoids (important inflammatory mediators). S1P functions mainly via G-protein-coupled receptors and probably also has intracellular targets. (PMID 16219683). C18H38NO5P None None None 3066.45 2851.27 2688.94 3779.29 2573.53 3118.49 2927.97 3049.03 3035.08 2126.49 2845.89 3414.25 2428.68 2918.16 2996.52 2450.12 3334.13 2246.76 1848.03 2700.61 2803.85 2100.89 2532.35 2802.57 2858.5 2649.72 2567.46 2780.23 2180.59 2905.52 2837.98 2370.56 2376.37 2481.5 2365.42 2435.35 2291.37 2431.53 1611.26 2818.83 2441.09 2569.19 379.0826881_MZ Rosmarinic acid Un 1.0 None None None None Rosmarinic acid is an ester of caffeic acid and 3,4-dihydroxyphenyllactic acid. It is commonly found in species of the Boraginaceae and the subfamily Nepetoideae of the Lamiaceae. It is a red-orange powder that is slightly soluble in water, but well soluble is most organic solvents. Rosmarinic acid is one of the polyphenolic substances contained in culinary herbs such as perilla (Perilla frutescens L.), rosemary (Rosmarinus officinalis L.), sage (Salvia officinalis L.), mint (Mentha arvense L.), and basil (Ocimum basilicum L.). These herbs are commonly grown in the garden as kitchen herbs, and while used to add flavor in cooking, are also known to have several potent physiological effects. (PMID: 12482446, 15120569). C18H16O8 None None None 23519.4 22744.7 25305.3 29177.5 17185.1 36479.5 23527.2 14971.8 22206.7 64298.1 23677.3 24012.8 37988.5 29516.4 33053.5 75527.1 14059.3 29328.0 38297.4 33331.3 26536.4 25963.5 28701.6 21343.0 25119.5 24885.3 42536.3 35401.0 40525.4 39139.2 34576.3 63027.4 16675.4 23729.5 37869.1 49412.4 19888.1 21858.9 17693.7 30261.0 41452.3 26111.0 379.2489123_MZ Bisnorcholic acid Un 1.0 None None None None Bisnorcholic acid is one of a number of short side bile acids found in the urine from patients with cerebrotendinous xanthomatosis (CTX). The presence these short side bile acids in urine of the CTX patients suggests that bile alcohols may be further degraded to these bile acids. (PMID: 2079611). C22H36O5 None None None 10173.2 8529.39 8315.88 8278.03 8306.55 12175.3 9970.19 13806.7 8411.3 7886.34 9828.71 7777.04 6889.67 11257.7 11580.1 9484.92 12460.1 9671.31 7961.65 10878.8 8884.91 6828.18 9403.88 10203.8 9513.46 7390.64 9372.6 10160.5 8104.22 10795.7 8967.86 7788.11 7677.56 8436.8 7175.72 7707.06 6608.21 7291.5 7498.81 9324.35 7037.3 9547.59 380.2473955_MZ Sphinganine 1-phosphate Un 1.0 None None None None Sphinganine 1-phosphate is an intermediate in the metabolism of Glycosphingolipids and sphingolipids. It is a substrate for Sphingosine kinase 1, Lipid phosphate phosphohydrolase 2, Sphingosine kinase 2, Sphingosine-1-phosphate lyase 1, Lipid phosphate phosphohydrolase 1 and Lipid phosphate phosphohydrolase 3. C18H40NO5P None None None 2432.5 2155.81 2535.4 2776.22 2215.36 2855.62 3673.44 4223.66 1710.35 2032.65 2742.18 1820.71 2329.05 3119.84 3005.44 2320.08 5186.33 2893.84 1818.12 3162.28 2149.8 1382.78 2793.13 3031.32 2202.85 1656.0 2152.79 2972.73 1910.45 3386.72 2634.58 1789.29 1753.95 2714.68 1648.73 2252.1 1547.01 1521.49 1890.26 2397.72 2870.15 2435.09 381.1552403_MZ 1-(alpha-Methyl-4-(2-methylpropyl)benzeneacetate)-beta-D-Glucopyranuronic acid Un 1.0 None None None None Ibuprofen acyl glucuronide is a natural human metabolite of Ibuprofen generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys. C19H26O8 None None None 5619.31 6458.74 7656.71 6611.17 6987.93 7454.18 7673.52 9115.9 5088.11 6664.94 6282.04 5526.81 4784.27 6774.89 8772.06 8497.15 13702.0 4620.77 6009.54 7328.11 6035.16 4974.4 6204.06 6008.9 6153.25 4448.65 6840.06 5394.83 4433.55 7005.7 6680.75 6449.52 4816.68 4672.6 5558.74 6349.74 4373.79 4973.89 4230.07 6958.97 5133.16 5780.29 381.3001176_MZ Monoacylglyceride with formula C23H42O4 Un 1.0 None None None None C23H42O4 None None None 2501.01 2540.64 3818.41 2420.56 3021.59 2467.33 2846.24 5647.66 1960.97 2382.59 2713.56 2294.03 1812.29 2692.46 3691.85 3157.3 8086.07 3295.81 1848.53 3823.93 2037.32 1920.8 2090.47 2413.17 2655.24 2033.29 3263.79 2814.81 2191.71 2828.98 2254.18 2342.14 1993.49 2233.05 2223.67 2476.12 1656.18 2291.09 2439.4 2709.55 1472.67 2150.16 381.3726447_MZ Pentacosanoic acid Un 1.0 None None None None C25H50O2 None None None 9560.38 10699.6 9308.7 9863.02 9961.14 8593.93 10682.4 13131.1 9036.43 9669.87 10300.6 9878.7 9707.04 10602.3 8686.23 8749.73 11985.9 16106.2 8571.17 11517.6 8770.26 8047.12 9097.29 10505.4 9532.56 8741.18 8767.78 11705.9 8376.22 10390.3 9108.52 7949.04 9353.81 10091.1 9157.43 10013.0 7797.16 9558.44 10119.8 9185.81 8396.48 9154.96 382.1005898_MZ Succinyladenosine Un 1.0 None None None None Succinyladenosine (SAdo) is one of the dephosphorylated enzyme substrate that accumulates in body fluids of patients with adenylosuccinate lyase (ADSL) deficiency, the other being 5-amino-4-imidazole-N-succinocarboxamide riboside (SAICAr). ADSL is an inherited metabolic disease characterized by various degrees of psychomotor retardation. (PMID 15902552). The severity of the clinical presentation correlates with a low S-Ado/SAICAr ratio in body fluids. (PMID: 15571235). Normally Succinyladenosine is not found in blood or CSF but may be detected in trace amounts in urine. (OMIM 103050). C14H17N5O8 None None None 27543.4 23512.9 28740.6 15818.5 28405.1 27706.0 21306.5 27091.5 25601.0 24438.2 22873.0 31840.2 22734.1 27128.5 32962.7 26119.1 19486.5 24752.6 26510.5 23274.2 26801.9 35628.1 27670.2 27125.1 24424.5 29227.3 25169.0 29896.8 35480.0 22242.2 16298.3 25639.6 20813.2 20543.7 40261.1 25093.2 24002.7 26047.4 21284.9 38203.6 18142.6 25208.3 382.1341321_MZ N-Acetyllactosamine Un 1.0 None None None None N-Acetyllactosamine is an intermediate in the biosynthesis of Keratan sulfate and the biosynthesis of N-Glycan. It is a substrate for Beta-1,4-galactosyltransferase 4, Beta-1,4-galactosyltransferase 2, Beta-1,4-galactosyltransferase 1, Beta-1,4-galactosyltransferase 3 and CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,6-sialyltransferase. C14H25NO11, Beta-1,4-mannose-N-acetylglucosamine, Lacto-N-biose I, Poly-N-acetyllactosamine None None None 4554.1 4529.19 5267.29 4356.13 5239.01 5791.12 4571.72 4471.08 4909.11 5085.88 4980.59 5468.34 4054.02 5155.99 5875.49 5312.9 4301.99 3866.97 4652.09 4558.86 5022.05 5457.96 5259.63 4788.86 4114.07 4596.26 4722.42 4535.89 5170.17 4997.06 4258.92 4126.39 4812.67 3918.85 5897.02 4758.12 4005.6 4907.59 4423.63 5796.26 3427.44 4013.64 382.1566239_MZ Quetiapine Un 1.0 None None None None The most common side effect is sedation, and is prescribed specifically for this effect in patients with sleep disorders. Seroquel will put the patient into a drowsy state, and will help the patient fall asleep. It is one of the most sedating of all anti psychotic drugs, rivaling even the most sedating older antipsychotics. Many prescriptions call for the entire dose to be taken before bedtime because of its sedative effects. Although quetiapine is approved by the FDA for the treatment of schizophrenia and bipolar disorder, it is frequently prescribed for off-label purposes including insomnia or the treatment of anxiety disorders. Due to its sedative side effects, reports of quetiapine abuse (sometimes by insufflating crushed tablets) have emerged in medical literature; Quetiapine belongs to a series of neuroleptics known as atypical antipsychotics, which have become increasingly popular alternatives to typical antipsychotics such as haloperidol. Quetiapine HAS approvals for the treatment of schizophrenia and acute mania in bipolar disorder. It is also used off-label to treat other disorders, such as post-traumatic stress disorder, alcoholism, obsessive compulsive disorder, anxiety disorders, hallucinations in Parkinson's disease patients using ropinirole, and as a sedative for those with sleep disorders. The most common side effect is sedation, and is prescribed specifically for this effect in patients with sleep disorders. Seroquel will put the patient into a drowsy state, and will help the patient fall asleep. It is one of the most sedating of all anti psychotic drugs, rivaling even the most sedating older antipsychotics. Many prescriptions call for the entire dose to be taken before bedtime because of its sedative effects. Although quetiapine is approved by the FDA for the treatment of schizophrenia and bipolar disorder, it is frequently prescribed for off-label purposes including insomnia or the treatment of anxiety disorders. Due to its sedative side effects, reports of quetiapine abuse (sometimes by insufflating crushed tablets) have emerged in medical literature; for the same reason, abuse of other antipsychotics, such as chlorpromazine (Thorazine), may occur as well, but research related to the abuse of typical antipsychotics is limited. for the same reason, abuse of other antipsychotics, such as chlorpromazine (Thorazine), may occur as well, but research related to the abuse of typical antipsychotics is limited. C21H25N3O2S None None None 2472.0 2582.49 2742.04 2644.19 2665.38 3349.21 2840.58 2852.9 2351.43 2598.38 2505.77 2319.72 2014.44 2880.8 3242.68 3259.44 3877.66 1753.7 2288.37 2544.98 2572.34 2361.52 2847.77 2709.67 2237.08 2005.16 2546.32 2438.15 2145.19 3155.0 2374.52 2491.68 1650.7 1872.02 2706.23 2687.69 1926.15 2066.38 2307.63 2749.29 1815.79 2165.62 382.1900141_MZ Isopentenyladenine-9-N-glucoside Un 1.0 None None None None Isopentenyladenine-9-N-glucoside is produced when isopentenyladenine and UDP-D-glucose react, with UDP as a byproduct. The reaction is catalyzed by UDP glycosyltransferases. C17H25N5O4 None None None 3240.83 3101.54 3137.88 3588.26 3595.53 5587.96 4223.37 3520.93 7149.6 7295.88 3230.66 2939.97 1675.4 6368.35 6400.44 4128.89 4397.8 1852.74 2643.65 3797.34 3150.48 2553.93 3192.91 3150.18 2920.51 2620.15 3190.07 2696.45 2524.25 3700.35 3066.97 2997.39 2478.85 2271.09 2935.02 4118.95 2092.78 2961.37 1583.26 3198.01 2918.7 3845.5 383.1165895_MZ S-Adenosylhomocysteine Un 1.0 None None None None S-Adenosylhomocysteine (AdoHcy) is the immediate precursor of all of the homocysteine produced in the body. The reaction is catalyzed by S-adenosylhomocysteine hydrolase and is reversible with the equilibrium favoring formation of AdoHcy. In vivo, the reaction is driven in the direction of homocysteine formation by the action of the enzyme adenosine deaminase, which converts the second product of the S-adenosylhomocysteine hydrolase reaction, adenosine, to inosine. Except for methyl transfer from betaine and from methylcobalamin in the methionine synthase reaction, AdoHcy is the product of all methylation reactions that involve S-adenosylmethionine (AdoMet) as the methyl donor. Methylation is significant in epigenetic regulation of protein expression via DNA and histone methylation. The inhibition of these AdoMet-mediated processes by AdoHcy is a proven mechanism for metabolic alteration. Because the conversion of AdoHcy to homocysteine is reversible, with the equilibrium favoring the formation of AdoHcy, increases in plasma homocysteine are accompanied by an elevation of AdoHcy in most cases. Disturbances in the transmethylation pathway indicated by abnormal S-adenosylmethionine, S-adenosylhomocysteine or their ratio have been reported in many neurodegenerative diseases, such as dementia, depression or Parkinson's disease. (PMID: 18065573, 17892439). C14H20N6O5S None None None 134684.0 179144.0 149457.0 159315.0 139328.0 169839.0 128472.0 125415.0 145252.0 147222.0 180403.0 137102.0 124108.0 140116.0 155442.0 198445.0 121488.0 140956.0 189648.0 118563.0 176914.0 163324.0 145646.0 152337.0 137113.0 128205.0 174113.0 137513.0 174644.0 176473.0 141201.0 141855.0 102950.0 118746.0 166779.0 186081.0 136080.0 154134.0 77471.9 195004.0 124873.0 147333.0 383.3151382_MZ Monoacylglyceride with formula C23H44O4 Un 1.0 None None None None MG(0:0/20:1(11Z)/0:0) is a monoacylglyceride. A monoglyceride, more correctly known as a monoacylglycerol, is a glyceride consisting of one fatty acid chain covalently bonded to a glycerol molecule through an ester linkage. Monoacylglycerol can be broadly divided into two groups; 1-monoacylglycerols (or 3-monoacylglycerols) and 2-monoacylglycerols, depending on the position of the ester bond on the glycerol moiety. Normally the 1-/3-isomers are not distinguished from each other and are termed 'alpha-monoacylglycerols', while the 2-isomers are beta-monoacylglycerols. Monoacylglycerols are formed biochemically via release of a fatty acid from diacylglycerol by diacylglycerol lipase or hormone sensitive lipase. Monoacylglycerols are broken down by monoacylglycerol lipase. They tend to be minor components only of most plant and animal tissues, and indeed would not be expected to accumulate because their strong detergent properties would have a disruptive effect on membranes. 2-Monoacylglycerols are a major end product of the intestinal digestion of dietary fats in animals via the enzyme pancreatic lipase. They are taken up directly by the intestinal cells and converted to triacylglycerols via the monoacylglycerol pathway before being transported in lymph to the liver. Mono- and Diglycerides are commonly added to commercial food products in small quantities. They act as emulsifiers, helping to mix ingredients such as oil and water that would not otherwise blend well. C23H44O4 None None None 6134.43 5950.23 7072.47 5790.84 6160.98 5049.32 6197.12 10001.6 5240.08 5383.72 6074.65 5327.71 5562.28 6007.62 6488.85 5569.51 12938.8 7839.86 5053.31 8100.66 5374.62 4627.49 5613.46 6478.14 5815.13 5132.71 6080.78 6885.63 4863.2 5841.33 5499.32 5093.91 4979.71 5443.19 5043.04 5628.57 4657.12 4976.17 6581.91 5903.4 4940.88 5671.84 386.0157422_MZ dCDP Un 1.0 None None None None dCDP is a substrate for Uridine-cytidine kinase 1, Nucleoside diphosphate kinase (mitochondrial), Nucleoside diphosphate kinase homolog 5, Ribonucleoside-diphosphate reductase large subunit, Nucleoside diphosphate kinase A, Nucleoside diphosphate kinase 7, Ribonucleoside-diphosphate reductase M2 chain, Nucleoside diphosphate kinase B, Nucleoside diphosphate kinase 3, Nucleoside diphosphate kinase 6 and UMP-CMP kinase. C9H15N3O10P2 None None None 39696.7 43186.5 33593.4 38557.7 35595.7 45334.4 42736.1 34795.6 32623.2 36510.6 36178.0 30050.6 55980.4 30175.2 33372.9 140438.0 32120.0 52871.4 34188.6 42611.2 37667.2 29989.6 35278.5 39351.1 52311.9 28773.3 40133.4 39669.7 33827.3 30724.6 53533.9 99861.3 31781.3 32527.1 40197.3 43836.4 30392.2 30982.5 24377.9 39658.0 59978.0 43419.5 387.0727512_MZ Dopaxanthin quinone Un 1.0 None None None None Dopaxanthin quinone is produced by the reaction between dopaxanthin and oxygen, with water as a byproduct. A tyrosinase precursor enzyme catalyzes the reaction. C18H16N2O8 None None None 4022.03 4086.67 5030.68 3530.09 4428.1 5070.1 4879.89 4242.0 4275.56 4160.08 4028.28 4592.42 3439.94 3876.94 5165.82 4310.59 3922.54 4284.24 4227.63 4517.22 3682.33 4178.9 3623.18 4055.76 4152.86 3737.9 4586.61 3905.63 3932.72 4889.21 3719.55 3180.45 4157.13 3709.15 4480.09 4210.67 3827.29 3951.73 3313.15 3929.69 3587.2 3561.24 389.1809847_MZ Androsterone sulfate Un 1.0 None None None None Androsterone sulfate (Andros-S) is the most abundant 5 alpha-reduced androgen metabolite in serum (PMID 8380602). Androsterone sulfate is clinically recognized as one of the major androgen metabolites found in urine. It is a cognate substrate for human dehydroepiandrosterone sulfotransferase, which catalyzes the transfer of the sulfonate group from 3'-phosphoadenosine-5'-phosphosulfate to dehydroepiandrosterone (DHEA) (PMID 14573603). C19H30O5S, Etiocholanolone sulfate, 5a-Dihydrotestosterone sulfate None None None 23585.9 23171.6 8427.48 28481.7 7381.06 13677.2 7092.3 8835.08 13214.6 12714.8 10856.7 6441.84 4493.35 18637.4 10341.5 9541.35 12155.2 4428.19 6381.64 7304.57 18991.9 6085.19 11517.8 26223.7 11945.4 6055.1 8149.54 6598.2 5392.89 28589.2 7092.94 10147.3 4633.08 11451.0 7148.14 22967.1 11299.8 5000.63 4592.62 20425.5 4451.88 14992.3 390.2199962_MZ 9'-carboxy-gama-tocotrienol Un 1.0 None None None None 9'-carboxy-r-tocotrienol is a dehydrogenation carboxylate product of 9'-hydroxy-r-tocotrienol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate. Gamma-tocotrienol targets cancer cells by inhibiting Id1, a key cancer-promoting protein. Gamma-tocotrienol was shown to trigger cell apoptosis and well as anti-proliferation of cancer cells. This mechanism was also observed in separate prostate cancer and melanoma cell line studies. C23H31O4 None None None 3730.94 3491.57 2509.57 4058.78 2487.32 3336.89 2900.43 2832.04 2778.06 2893.47 2784.74 2179.37 1910.97 3646.53 2890.63 2819.6 3650.22 2110.53 2227.75 2672.18 2857.6 1873.41 2841.95 3381.33 2894.12 1995.81 2639.09 2416.93 1915.64 4203.75 2739.51 2450.15 1667.14 2562.21 2189.52 3312.04 2338.89 1803.8 1735.34 3058.7 2433.65 2723.1 390.3090546_MZ Tetradecanoylcarnitine Un 1.0 None None None None Tetradecanoylcarnitine is a human carnitine involved in b-oxidation of long-chain fatty acids (PMID: 16425363). C21H41NO4 None None None 964.164 702.895 596.404 836.25 412.701 870.525 576.955 653.932 666.847 535.326 598.746 590.996 761.986 672.021 1417.99 703.327 668.85 1035.5 553.784 862.431 889.973 419.406 707.463 1083.77 728.596 672.178 680.674 880.487 661.209 1036.48 785.961 888.924 605.653 861.054 552.49 595.053 619.095 579.745 875.595 767.279 412.938 792.904 391.2853342_MZ 3b,12a-Dihydroxy-5a-cholanoic acid Un 1.0 None None None None 3b,12a-Dihydroxy-5a-cholanoic acid is a bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. C24H40O4, 3b,7a-Dihydroxy-5b-cholanoic acid, 3a,7a-Dihydroxycholanoic acid, 3a,12b-Dihydroxy-5b-cholanoic acid, 3b,12a-Dihydroxy-5b-cholanoic acid, Allodeoxycholic acid, Allochenodeoxycholic acid, Chenodeoxycholic acid, Deoxycholic acid, Isohyodeoxycholic acid, Isoursodeoxycholic acid, Hyodeoxycholic acid, Murocholic acid, Ursodeoxycholic acid, 7b,12a-Dihydroxycholanoic acid, 7a,12b-dihydroxy-5b-Cholan-24-oic acid, Isodeoxycholic acid, 3b,12b-Dihydroxy-5b-cholanoic acid None None None 213710.0 9615.18 11565.0 7069.49 7738.99 107672.0 9619.45 8548.82 4106.96 81837.4 62336.3 9297.17 5663.01 176445.0 10685.4 7288.75 9119.01 11158.9 9425.16 91640.3 59824.3 5484.68 61003.9 47302.2 8244.12 8436.07 8412.48 8356.38 6987.75 305740.0 73700.0 11806.8 5771.68 34085.5 5972.66 9101.8 4620.15 5122.58 9338.71 8732.38 76517.4 11367.4 393.1136604_MZ Portulacaxanthin II Un 1.0 None None None None Portulacaxanthin II is involved in betaxanthin biosynthesis (via dopaxanthin) pathway. This pathway demonstrates the formation of betaxanthins such as portulacaxanthin II and dopaxanthin by means of non-enzymatic condensation from the amino acids L-tyrosine and L-DOPA, respectively. Tyrosinases have been described as capable to use those betaxanthins [ GandiaHerr05a ] as substrates for further metabolization. C18H18N2O7 None None None 5623.19 5306.42 7619.61 5495.24 7410.5 6926.62 7244.29 6686.58 4900.23 5884.14 6138.84 5849.18 5222.0 5213.65 7357.9 8448.6 6525.92 5760.92 6701.11 6193.11 6054.74 4264.53 5678.36 5354.67 6659.33 5524.83 8266.43 5893.98 5049.84 5739.64 6996.16 6407.15 4782.44 4763.83 5458.96 5892.0 5433.1 4857.13 3759.25 5646.34 5339.48 6390.53 393.2449060_MZ Calcitroic acid Un 1.0 None None None None Calcitroic acid (1 alpha-hydroxy-23 carboxy-24,25,26,27-tetranorvitamin D(3)) is a metabolite of 1 alpha, 25-dihydroxyvitamin D(3) (calcitriol). It is soluble in water, and is excreted in urine. This deactivation process involves a series of oxidation reactions at C24 and C23 leading to side-chain cleavage and, ultimately, formation of the calcitroic acid. This deactivation involves the loss of carbons 24, 25, 26, and 27 and the oxidation of carbon 23 to a carboxylic acid. Calcitroic acid is also a major terminal product for the deactivation of 1α,25-dihydroxyvitamin D2. Both the kidney and the intestine metabolize 1,25-dihydroxyvitamin D3 through the C-24 oxidation pathway according to the following steps: 1,25-dihydroxyvitamin D3----1,24,25-trihydroxyvitamin D3----1,25-dihydroxy-24-oxovitamin D3-----1,23,25-trihydroxy-24-oxovitamin D3 (PMID: 2719932). The C-24 oxidation pathway leading to the formation of calcitroic acid has been reported to be present in bone cells, but the C-23 oxidation pathway leading to the formation of 1 alpha, 25-(OH)2D3-26,23-lactone has not been described in bone cells, even though 1 alpha, 25-(OH)2D3-26,23-lactone is noted to have a significant effect on bone formation. (PMID: 7664636). C23H34O4, LysoPhosphatidic Acid (P-16:0e/0:0) None None None 3332.51 2949.01 2597.85 2586.85 2729.74 3751.93 2968.12 3411.08 2637.54 4236.98 3376.83 2300.26 2265.74 2899.49 3103.78 3054.05 5493.02 4067.85 2967.3 3269.35 2597.39 1823.58 3479.34 2772.54 2636.6 2018.77 3000.76 2849.18 1760.38 3678.44 2686.75 2453.25 1706.66 1942.92 2125.46 3816.57 1857.36 1841.51 2080.09 2611.97 3183.1 3571.25 394.2930328_MZ 9,12-Hexadecadienoylcarnitine Un 1.0 None None None None 9,12-Hexadecadienoylcarnitine is an acylcarnitine with C16:2 fatty acid moiety. Acylcarnitine useful in the diagnosis of fatty acid oxidation disorders and differentiation between biochemical phenotypes of medium-chain acyl-CoA dehydrogenase (MCAD) deficiency deficiencyoxidation disorders.(PMID: 12385891). C23H41NO4 None None None 2355.83 1311.49 983.682 630.267 1032.88 2409.96 1254.46 1947.99 821.936 1326.67 1375.34 929.786 1292.32 2438.95 1128.2 1735.8 1459.52 1447.88 1061.16 2136.08 1169.18 863.073 1583.36 1558.04 1045.48 1081.06 816.402 1344.97 1097.37 3038.07 1628.96 1075.29 681.213 1202.8 819.946 1013.73 630.92 1073.73 901.141 1148.24 1279.5 1178.92 395.3883296_MZ Hexacosanoic acid Un 1.0 None None None None X-linked adrenoleukodystrophy (X-ALD) is a peroxisomal disorder biochemically characterized by the accumulation of very long chain fatty acids (VLCFA), particularly hexacosanoic acid (C(26:0)) and tetracosanoic acid (C(24:0)), in tissues and biological fluids. (PMID 16750542). C26H52O2 None None None 10147.7 11671.1 9805.7 10220.9 10715.5 8835.94 11379.6 13067.6 9551.23 10492.0 11151.3 10669.7 11073.6 11040.9 8991.78 9483.65 11624.1 17822.2 9382.95 12379.3 9488.22 9329.05 9123.88 10964.7 10070.3 9270.22 9399.46 12263.9 9053.37 11447.7 9470.49 8535.48 10236.5 11083.9 9923.94 10796.3 8313.08 10660.4 11205.3 10120.5 8556.04 10040.0 396.2833685_MZ PGD2 ethanolamide Un 1.0 None None None None C22H39NO5, PGF2a ethanolamide None None None 1227.37 1180.94 1023.33 978.643 1097.82 1522.56 1138.87 1795.36 914.605 1042.23 1135.91 1013.72 610.773 1283.61 1229.18 1560.28 2159.82 1267.86 981.873 1448.65 927.397 705.211 1045.69 1040.38 1070.06 913.869 1146.14 1269.91 653.552 1300.81 1230.48 1012.4 654.595 923.055 804.442 1121.4 729.44 538.378 725.273 1085.14 755.148 983.003 401.1287529_MZ Farnesyl pyrophosphate Un 1.0 None None None None Farnesyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. -- Wikipedia. C15H28O7P2 None None None 11157.2 9609.8 12962.8 6615.85 7014.95 14175.9 13521.6 8465.29 10359.6 11075.1 9077.38 14177.2 6163.67 6410.62 10817.9 7860.18 7572.02 6314.91 6766.99 12369.7 9730.39 8573.47 8023.7 8862.51 9073.54 10378.5 9119.21 8230.83 8289.72 10608.9 7806.94 7709.54 7314.52 6638.67 8379.25 8385.99 7961.7 9321.19 5055.05 10470.4 6834.7 8536.71 401.3414379_MZ (24R)-Cholest-5-ene-3-beta_24-diol Un 1.0 None None None None (24R)-Cholest-5-ene-3-beta,24-diol or 24(R)-Hydroxycholesterol is a hydroxysterol. It is a substrate for Cytochrome P450 39A1 (EC 1.14.13.99), which is primarily a liver-specific enzyme. It is involved in the following reaction: (24R)-cholest-5-ene-3-beta,24-diol + NADPH + O(2) = (24R)-cholest-5-ene-3-beta,7-alpha,24-triol + NADP(+) + H(2)O. 24(R)-Hydroxycholesterol is an intermediate in bile acid metabolism. The majority of circulating 24-hydroxycholesterol in humans is made in the brain and is increased in serum of Alzheimer patients. 24(S)-Hydroxycholesterol is generally more abundant in human tissues than 24(R)-Hydroxycholesterol. It has also been shown that 24(R) and 24(S)-Hydroxycholesterols are substrates for hepatic cholesterol 7-a hydroxylase (CYP7A), leading to the production of 7-alpha hydroxylated bile acids. C27H46O2, 20alpha-Hydroxycholesterol, 22b-Hydroxycholesterol, 4b-Hydroxycholesterol, 7a-Hydroxycholesterol, Delta-Tocopherol None None None 1986.66 1413.88 1455.82 1419.15 2012.03 1314.3 1469.15 1646.41 1524.99 1451.63 1648.77 1744.77 1457.41 2389.49 1647.87 1321.01 1465.57 1819.49 1090.18 1513.98 1577.97 1572.45 1560.83 1273.73 1395.26 1548.01 1052.76 2085.52 1815.46 1534.55 1158.07 1264.33 2160.39 1246.03 1408.54 1453.84 1496.54 1660.27 1287.49 1455.53 1452.16 1375.29 403.3573722_MZ 3a,7a-Dihydroxy-5b-cholestane Un 1.0 None None None None 3alpha,7alpha-Dihydroxy-5beta-cholestane is an intermediate in bile acid synthesis. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487, 16037564, 12576301, 11907135). C27H48O2 None None None 2193.03 910.619 775.502 699.241 455.038 928.237 394.481 449.682 446.166 798.12 752.988 520.137 557.697 794.603 421.801 649.828 1141.59 925.888 415.382 946.407 996.565 415.29 599.723 488.023 491.596 403.482 339.335 714.198 417.792 1134.66 322.366 469.212 491.67 619.926 586.199 415.768 1368.24 475.359 338.263 494.271 504.059 478.632 405.2638321_MZ 3-Oxocholic acid Un 1.0 None None None None 3-Oxocholic acid is a bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. C24H38O5, 3_7-Dihydroxy-12-oxocholanoic acid, 7-Ketodeoxycholic acid None None None 32268.0 21793.2 24758.7 22893.0 24845.5 23256.9 38424.5 111480.0 21611.2 19486.3 31556.0 25478.6 31111.7 28400.4 24606.1 19791.7 32798.1 28048.1 23751.4 31027.6 25241.4 15469.5 25098.6 37554.0 31516.6 24067.2 24305.4 27405.6 23238.5 25930.5 29496.9 21898.5 22508.5 21219.0 17779.9 20139.4 19989.7 23017.5 26519.1 24910.1 38779.6 39089.0 405.2997744_MZ Monoacylglyceride with formula C25H42O4 Un 1.0 None None None None MG(0:0/22:4(7Z,10Z,13Z,16Z)/0:0) is a monoacylglyceride. A monoglyceride, more correctly known as a monoacylglycerol, is a glyceride consisting of one fatty acid chain covalently bonded to a glycerol molecule through an ester linkage. Monoacylglycerol can be broadly divided into two groups; 1-monoacylglycerols (or 3-monoacylglycerols) and 2-monoacylglycerols, depending on the position of the ester bond on the glycerol moiety. Normally the 1-/3-isomers are not distinguished from each other and are termed 'alpha-monoacylglycerols', while the 2-isomers are beta-monoacylglycerols. Monoacylglycerols are formed biochemically via release of a fatty acid from diacylglycerol by diacylglycerol lipase or hormone sensitive lipase. Monoacylglycerols are broken down by monoacylglycerol lipase. They tend to be minor components only of most plant and animal tissues, and indeed would not be expected to accumulate because their strong detergent properties would have a disruptive effect on membranes. 2-Monoacylglycerols are a major end product of the intestinal digestion of dietary fats in animals via the enzyme pancreatic lipase. They are taken up directly by the intestinal cells and converted to triacylglycerols via the monoacylglycerol pathway before being transported in lymph to the liver. Mono- and Diglycerides are commonly added to commercial food products in small quantities. They act as emulsifiers, helping to mix ingredients such as oil and water that would not otherwise blend well. C25H42O4, Monoacylglyceride(22:4(7Z_10Z_13Z_16Z)/0:0/0:0) None None None 7602.81 9410.19 4884.27 6396.13 7254.52 10762.8 6995.35 10237.4 6704.18 6136.16 9606.58 9256.06 3087.7 6796.7 7031.52 9791.6 7074.35 3529.69 5066.4 5283.05 7059.85 3700.65 7443.21 7131.51 7005.03 4654.78 7847.72 6454.22 3433.2 8954.76 7435.92 6128.9 5028.03 4843.98 4223.68 5007.72 4876.14 5406.9 3002.27 6110.21 3653.08 4870.38 406.2232946_MZ Neurotensin 11-13 Un 1.0 None None None None C21H33N3O5 None None None 5227.76 5648.23 4569.8 5028.87 4608.98 5700.44 4933.36 5239.18 4947.51 5030.25 4975.78 4846.32 4934.45 5907.68 4851.49 5012.32 6052.55 4949.91 4834.77 4898.61 4646.28 4551.1 5334.48 5280.72 5071.27 4636.55 4596.69 5107.42 4364.72 5969.46 4409.41 4434.71 4285.08 4773.13 4566.96 5081.33 4239.49 4232.89 5024.89 4949.15 3858.79 4683.36 407.2421776_MZ 5,6-Dihydroxyprostaglandin F1a Un 1.0 None None None None Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways. C20H36O7 None None None 4393.76 3946.41 3876.3 4416.46 4277.59 5314.85 4129.32 5613.53 3418.54 4074.16 4990.87 2983.09 3167.49 4885.3 5195.28 4767.32 6622.35 4807.01 3778.03 5071.5 4114.15 2618.88 4604.06 4551.62 4500.86 3013.0 4741.62 4799.17 2884.46 5233.61 4225.7 3614.23 2636.21 3189.59 2910.03 4240.29 2580.32 2590.03 2839.28 4599.46 4819.56 4575.71 407.2792793_MZ Cholic acid Un 1.0 None None None None Cholic acid is a major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487, 16037564, 12576301, 11907135). C24H40O5, Muricholic acid, Allocholic acid, Ursocholic acid, 1b_3a_12a-Trihydroxy-5b-cholanoic acid, 3a_6b_7b-Trihydroxy-5b-cholanoic acid, 6a_12a-Dihydroxylithocholic acid None None None 66806.6 34712.4 78101.8 27516.7 15003.5 52395.6 63239.1 128416.0 20732.3 31085.2 68127.0 36571.1 12152.1 132089.0 56999.9 25559.2 77271.4 46533.2 92934.4 44986.8 49956.2 16176.9 31988.9 130838.0 120755.0 24805.3 58888.7 32004.4 73314.0 65825.9 52335.4 28480.2 17611.9 35505.0 91303.1 21199.4 30500.6 35031.8 60692.0 44313.5 159676.0 135461.0 409.2350740_MZ LPA with formula C19H39O7P Un 1.0 None None None None LPA(0:0/16:0) is a lysophosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. Lysophosphatidic acids can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. Fatty acids containing 16 and 18 carbons are the most common. Lysophosphatidic acid is the simplest possible glycerophospholipid. It is the biosynthetic precursor of phosphatidic acid. Although it is present at very low levels only in animal tissues, it is extremely important biologically, influencing many biochemical processes. In particular, lysophosphatidic acid is an intercellular lipid mediator with growth factor-like activities, and is rapidly produced and released from activated platelets to influence target cells. 1-Palmitoyl lysophosphatidic acid is the major component of lysophosphatidic acid (LPA) in plasma, and is in a reduced ratio in individuals with gynecological cancers (PMID 11585410). LPA is a pluripotent lipid mediator controlling growth, motility, and differentiation, that has a strong influence on the chemotaxis and ultrastructure of human neutrophils (PMID 7416233). In serum and plasma, LPA is mainly converted from lysophospholipids, whereas in platelets and some cancer cells it is converted from phosphatidic acid. In each pathway, at least two phospholipase activities are required: phospholipase A1 (PLA1)/PLA2 plus lysophospholipase D (lysoPLD) activities are involved in the first pathway and phospholipase D (PLD) plus PLA1/PLA2 activities are involved in the second pathway. (PMID 15271293). C19H39O7P None None None 17043.4 20457.9 21446.0 21398.5 26258.5 23039.6 24317.2 22623.7 22758.9 22429.9 27514.1 29045.4 20258.1 22806.2 22498.8 19008.5 22596.8 29257.3 16140.5 25426.8 18603.0 19945.4 22372.7 16467.7 22231.3 21193.2 20035.1 25605.0 20399.3 21589.6 25257.0 21690.5 26394.8 16121.7 16489.5 19051.5 17343.8 25128.4 13199.3 21634.2 24834.3 17575.7 409.3098877_MZ Gama-Tocotrienol Un 1.0 None None None None gamma-tocotrienol targets cancer cells by inhibiting Id1, a key cancer-promoting protein. Gamma-tocotrienol was shown to trigger cell apoptosis and well as anti-proliferation of cancer cells. This mechanism was also observed in separate prostate cancer and melanoma cell line studies. C28H42O2 None None None 5537.68 4261.43 4722.38 3976.33 3505.2 2680.71 7399.38 8457.27 2610.57 3092.8 3557.84 2612.99 6800.62 3875.07 3569.82 3577.42 10207.3 12543.5 4366.98 8823.16 3976.11 1717.72 3655.34 5336.51 3884.55 2120.19 3441.79 8618.4 2466.04 3880.14 6947.55 3563.83 2330.28 4304.35 2116.75 4328.7 2213.32 1890.66 4544.34 4158.77 9962.51 5535.77 409.3308885_MZ Monoacylglyceride with formula C25H46O4 Un 1.0 None None None None C25H46O4 None None None 2782.33 2815.62 3784.07 2651.09 2730.56 2218.73 3104.61 5855.65 2103.44 2385.22 2766.31 2209.36 2781.22 2886.12 3169.41 2929.81 7628.25 4544.64 2274.66 4542.06 2257.63 1844.73 2298.63 2651.19 2735.13 1894.76 3013.38 3467.95 1921.33 2789.24 3018.44 2336.98 2062.49 2475.31 1998.35 2595.99 1714.12 2079.68 2861.65 2660.39 2705.42 2548.2 409.4036512_MZ Heptacosanoic acid Un 1.0 None None None None Heptacosanoic acid is a fatty acid found in follicular casts (the abnormal impactation of a sebaceous follicle) implicated as the preclinical lesion of acne vulgaris. (PMID: 2940302). Heptacosanoic acid is one of the fatty acids found that contribute to a significant increase in the microviscosity of erythrocyte membranes in patients affected with adrenoleukodystrophy (ALD) and adrenomyeloneuropathy (AMN). (PMID: 6874949). Heptacosanoic acid has been found in the adrenal cortex and brain, in adrenoleukodystrophy and Zellweger syndrome in humans. (PMID: 3806133). Heptacosanoic acid has been found in blood and tissues of patients with different genetic peroxisomal disorder (Refsum's disease, X-linked adrenoleukodystrophy, neonatal adrenoleukodystrophy or Zellweger syndrome). (PMID: 2474624). C27H54O2 None None None 6276.22 5849.47 4562.4 4471.88 5284.43 4907.71 6767.8 7559.16 4088.3 4853.32 4722.98 4567.41 6446.23 6206.65 4365.96 4719.91 8030.56 8291.08 4888.53 6502.86 4329.64 3143.28 5450.58 5354.14 4700.33 3495.93 4466.01 6599.73 3311.59 6084.75 5066.26 3779.95 4173.41 4522.38 3466.29 4716.05 3583.86 4030.68 5483.43 5047.42 4725.56 4452.9 410.1344667_MZ 13E-Tetranor-16-carboxy-LTE4 Un 1.0 None None None None 13E-tetranor-16-carboxy-LTE4 is a metabolite through lipid oxidation of Leukotriene E4 (LTE4).Leukotriene E4 (LTE4) is a cysteinyl leukotriene. Cysteinyl leukotrienes (CysLTs) are a family of potent inflammatory mediators that appear to contribute to the pathophysiologic features of allergic rhinitis. Nasal blockage induced by CysLTs is mainly due to dilatation of nasal blood vessels, which can be induced by the nitric oxide produced through CysLT1 receptor activation. LTE4, activate contractile and inflammatory processes via specific interaction with putative seven transmembrane-spanning receptors that couple to G proteins and subsequent intracellular signaling pathways. LTE4 is metabolized from leukotriene C4 in a reaction catalyzed by gamma-glutamyl transpeptidase and a particulate dipeptidase from kidney. (PMID: 12607939, 12432945, 6311078). Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways. C19H25NO7S None None None 3559.76 5234.23 4013.3 3840.96 5216.62 4913.99 3744.89 2370.77 3604.47 3124.66 3439.49 3230.85 2164.15 3562.45 5028.21 5745.29 3440.53 2800.51 3444.1 2946.09 4449.37 3007.99 3532.05 3291.37 4285.95 2921.83 4194.31 2948.65 2737.09 4492.0 3841.9 4460.86 2558.49 3213.54 3887.69 3327.71 3302.74 2547.6 2206.8 3923.23 2198.74 3677.08 411.3467855_MZ Monoacylglyceride with formula C25H48O4 Un 1.0 None None None None MG(0:0/22:1(13Z)/0:0) is a monoacylglyceride. A monoglyceride, more correctly known as a monoacylglycerol, is a glyceride consisting of one fatty acid chain covalently bonded to a glycerol molecule through an ester linkage. Monoacylglycerol can be broadly divided into two groups; 1-monoacylglycerols (or 3-monoacylglycerols) and 2-monoacylglycerols, depending on the position of the ester bond on the glycerol moiety. Normally the 1-/3-isomers are not distinguished from each other and are termed 'alpha-monoacylglycerols', while the 2-isomers are beta-monoacylglycerols. Monoacylglycerols are formed biochemically via release of a fatty acid from diacylglycerol by diacylglycerol lipase or hormone sensitive lipase. Monoacylglycerols are broken down by monoacylglycerol lipase. They tend to be minor components only of most plant and animal tissues, and indeed would not be expected to accumulate because their strong detergent properties would have a disruptive effect on membranes. 2-Monoacylglycerols are a major end product of the intestinal digestion of dietary fats in animals via the enzyme pancreatic lipase. They are taken up directly by the intestinal cells and converted to triacylglycerols via the monoacylglycerol pathway before being transported in lymph to the liver. Mono- and Diglycerides are commonly added to commercial food products in small quantities. They act as emulsifiers, helping to mix ingredients such as oil and water that would not otherwise blend well. C25H48O4 None None None 5675.96 5542.72 7889.84 5757.9 6082.32 4482.17 5888.9 10917.7 4847.66 5283.01 5729.37 5053.92 4680.96 5915.7 6622.08 5844.28 14667.1 6818.54 4790.59 8008.99 4631.58 4633.29 4866.82 5291.16 5752.89 5024.06 6061.87 6289.51 4537.56 5906.66 5356.68 5102.49 4960.25 5130.35 4830.34 5475.71 4539.91 4873.04 6260.55 5612.19 4279.25 5307.07 411.3606751_MZ 24-Methylenelophenol Un 1.0 None None None None C29H48O, 4_4-Dimethyl-5a-cholesta-8_24-dien-3-b-ol, Avenasterol, Delta7-Avenasterol, Stigmasterol None None None 2635.98 2693.26 2751.05 2607.45 2325.85 1878.74 2510.55 3792.66 2167.86 2387.14 2681.42 2815.59 2797.36 2611.68 2505.94 2208.23 4218.95 3767.25 2210.1 3445.78 2352.35 2303.08 2025.53 2487.31 2385.16 2395.98 2354.65 3077.8 2303.63 2610.29 2223.38 2280.73 2575.22 2586.13 2280.3 2502.52 1990.02 2456.19 2819.59 2579.12 1959.32 2371.86 416.3041499_MZ 11'-Carboxy-alpha-chromanol Un 1.0 None None None None 11'-carboxy-alpha-tocopherol is a dehydrogenation carboxylate product of 11'-hydroxy-a-tocopherol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate. The tocopherols ( a-tocopherol , b-tocopherol ,r-tocopherol and d-tocopherol ) and their corresponding tocotrienols are synthesized by plants and have vitamin E antixoidant activity (see pathway vitamin E biosynthesis ). They differ in the number and location of methyl groups on the chromanol ring. The naturally occurring form of a-tocopherol is (2R,4'R,8'R)-a-tocopherol (synonym (R,R,R)-a-tocopherol). Synthetic a-tocopherols are a racemic mixture of eight different R and S stereoisomers. Only the 2R forms are recognized as meeting human requirements. The in vivo function of vitamin E is to scavenge peroxyl radicals via its phenolic (chromanol) hydroxyl group, thus protecting lipids against free radical-catalyzed peroxidation. The tocopheryl radical formed can then be reduced by reductants such as L-ascorbate. Other major products of a-tocopherol oxidation include α-tocopherylquinone and epoxy-a-tocopherols. The metabolites a-tocopheronic acid and its lactone, known as the Simon metabolites, are generally believed to be artefacts. In addition to these oxidation products, the other major class of tocopherol metabolites is the carboxyethyl-hydroxychromans.These metabolites are produced in significant amounts in response to excess vitamin E ingestion. Vitamin E is fat-soluble and its utilization requires intestinal fat absorption mechanisms. It is secreted from the intestine into the lymphatic system in chylomicrons which subsequently enter the plasma. Lipolysis of these chylomicrons can result in delivery of vitamin E to tissues, transfer to high-density lipoproteins (and subsequently to other lipoproteins via the phospholipid exchange protein), or retention in chylomicron remnants. These remnants are taken up by the liver. Natural (R,R,R)-α-tocopherol and synthetic 2R-α-tocopherols are then preferentially secreted from the liver into plasma as a result of the specificity of the α-tocopherol transfer protein. This protein, along with the metabolism of excess vitamin E in the liver and excretion into urine and bile, mediate the supply of a-tocopherol in plasma and tissues. C26H41O4 None None None 761.827 622.727 754.714 684.876 759.901 648.877 712.063 795.697 629.812 650.794 692.646 588.617 467.915 774.879 721.391 482.777 1106.37 823.821 610.937 1103.94 588.729 630.763 653.033 758.31 634.099 651.0 766.977 865.007 727.957 765.915 677.373 334.517 571.11 692.659 538.885 796.179 570.615 493.801 885.438 775.66 643.695 683.222 417.3357561_MZ 17a_20a-Dihydroxycholesterol Un 1.0 None None None None 17alpha,20alpha-Dihydroxycholesterol is an intermediate in C21-Steroid hormone metabolism. 17alpha,20alpha-Dihydroxycholesterol is the 8th to last step in the synthesis of Cortolone and is converted from 20alpha-Hydroxycholesterol via the enzyme cytochrome P450 (EC 1.14.99.9). It is then converted to 17alpha-Hydroxypregnenolone via the enzyme cytochrome P450 (EC1.14.15.6). C27H46O3, 3a_7a-Dihydroxy-5b-cholestan-26-al, 7a_12a-Dihydroxy-5a-cholestan-3-one, 7-a_25-Dihydroxycholesterol None None None 2510.1 2408.01 2528.23 2402.23 3195.71 2994.37 2558.83 2278.92 2389.24 2454.34 3053.52 2877.9 1886.33 3222.62 3972.41 2010.92 2307.69 2670.53 1789.44 2749.31 2502.63 2512.46 2343.18 2655.15 2648.93 2680.72 2647.38 2898.73 2365.71 2990.51 2153.7 2274.9 2966.68 2198.2 2383.71 2136.32 2055.95 2827.81 2037.49 2551.18 1879.29 2017.82 418.3017303_MZ Stearidonyl carnitine Un 1.0 None None None None C25H41NO4 None None None 1532.81 1660.08 1220.88 1507.28 1159.81 1588.36 1260.87 1654.92 1258.7 1085.19 1458.36 1731.35 1140.64 1371.82 1732.7 1294.18 1583.53 1389.95 950.908 1486.63 1122.25 958.392 1473.29 1351.41 1428.31 1160.0 1072.95 1898.47 1078.51 1518.72 1572.75 1095.92 1027.57 1499.1 1094.51 1094.74 1090.49 1103.61 1040.95 1144.81 1105.2 1302.75 418.3330854_MZ L-Palmitoylcarnitine Un 1.0 None None None None L-Palmitoylcarnitine is a long-chain acyl fatty acid derivative ester of carnitine which facilitates the transfer of long-chain fatty acids from cytoplasm into mitochondria during the oxidation of fatty acids. L-palmitoylcarnitine, due to its amphipatic character is, like detergents, a surface-active molecule and by changing the membrane fluidity and surface charge can change activity of several enzymes and transporters localized in the membrane. L-palmitoylcarnitine has been also reported to change the activity of certain proteins. On the contrary to carnitine, palmitoylcarnitine was shown to stimulate the activity of caspases 3, 7 and 8 and the level of this long-chain acylcarnitine increased during apoptosis. Palmitoylcarnitine was also reported to diminish completely binding of phorbol esters, the protein kinase C activators and to decrease the autophosphorylation of the enzyme. Apart from these isoform nonspecific phenomena, palmitoylcarnitine was also shown to be responsible for retardation in cytoplasm of protein kinase C isoforms β and δ and, in the case of the latter one, to decrease its interaction with GAP-43. Some of the physico-chemical properties of palmitoylcarnitine may help to explain the need for coenzyme A-carnitine-coenzyme A acyl exchange during mitochondrial fatty acid import. The amphiphilic character of palmitoylcarnitine may also explain its proposed involvement in the pathogenesis of myocardial ischemia. L-Palmitoylcarnitine accumulates in ischemic myocardium and potentially contribute to myocardial damage through alterations in membrane molecular dynamics , one mechanism through which could play an important role in ischemic injury. Palmitoylcarnitine is characteristically elevated in carnitine palmitoyltransferase II deficiency, late-onset (OMIM 255110). (PMID 2540838, 15363641, 8706815). C23H45NO4 None None None 784.303 799.681 936.019 974.582 949.949 858.115 781.897 833.583 761.428 842.072 885.846 841.168 479.631 945.231 950.681 554.946 1016.25 1066.13 637.694 802.021 733.917 761.556 944.991 805.736 815.153 815.675 831.293 974.214 728.131 794.508 801.324 664.452 941.362 885.44 745.495 801.401 715.092 858.976 706.33 882.651 703.697 777.986 419.2556469_MZ Cyclic phosphatidic acid with formula C21H41O6P Un 1.0 None None None None cPA(18:0/0:0) is a cyclic phosphatidic acid or cyclic lysophosphatidic acid. It is a glycerophospholipid in which a cyclic phosphate moiety occupies two glycerol substitution sites. Lysophosphatidic acids can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1). Fatty acids containing 16 and 18 carbons are the most common. Cyclic phosphatidic acids have been detected in a wide range of organisms including humans, especially in the brain but also in serum (at a concentration of 10-7M). cPA's have a cyclic phosphate at the sn-2 and sn-3 positions of the glycerol carbons, and this structure is absolutely necessary for their activities. In particular, it is found in tissues subject to injury, and while it may have some similar signalling functions to lysophosphatidic acid per se, it also has some quite distinct biological activities. For example, cyclic phosphatidic acid is known to be a specific inhibitor of DNA polymerase alpha. It has an appreciable effect on the inhibition of cancer cell invasion and metastasis. C21H41O6P None None None 8157.61 8769.66 8231.09 8891.48 8885.91 8701.05 9415.73 9155.73 8507.27 7516.6 10497.0 10788.0 6782.97 9667.67 8088.36 7309.46 9444.08 7639.45 6165.22 8804.58 7901.5 6657.42 8552.87 7495.36 8674.55 8196.04 7644.73 9213.19 6768.85 8817.49 7998.56 7134.61 8523.28 6537.45 6298.7 7007.65 6933.41 8446.05 5669.64 8350.45 7524.45 6991.5 419.3522212_MZ 3 alpha_7 alpha_26-Trihydroxy-5beta-cholestane Un 1.0 None None None None 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane is found in the primary bile acid biosynthesis pathway. 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane is produced from 3 alpha,7 alpha-Dihydroxy-5beta-cholestane through the action of CYP27A (E1.14.13.15). 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane is then converted to 3 alpha,7 alpha-Dihydroxy-5beta-cholestan-26-al by CYP27A (E1.14.13.15). C27H48O3, 3b_5a_6b-Cholestanetriol, 5-b-Cholestane-3a _7a _12a-triol None None None 3454.47 4544.61 5645.73 4065.16 6110.85 3595.74 5258.49 2927.66 4516.13 4596.97 6939.38 7457.42 2675.12 5272.09 4554.05 2611.13 3291.4 3572.66 2961.71 4150.45 2889.9 4590.91 4264.5 3052.12 4847.39 5991.5 3407.41 4526.04 4524.57 4318.47 3225.19 3283.68 8065.56 3050.63 3331.11 3069.5 3851.92 8040.69 3382.66 3614.43 2984.57 3163.5 421.2748968_MZ 7b-Hydroxy-3-oxo-5b-cholanoic acid Un 1.0 None None None None 7b-Hydroxy-3-oxo-5b-cholanoic acid was one of the bile acids present in significant proportions during early gestation, identified in amniotic fluid. (PMID 2373959). A bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487, 16037564, 12576301, 11907135). C25H38O4, Monoacylglyceride with formula C25H38O4 None None None 4058.24 2986.9 2791.37 3007.74 3700.09 3396.8 4390.79 5389.86 3970.82 4055.6 3561.2 2868.74 3845.63 4620.12 5882.91 3255.7 4163.15 5965.2 4468.16 4986.02 3118.68 2212.55 3310.72 3650.23 3203.08 2884.8 3145.46 4413.16 3029.21 4068.46 3414.78 2615.1 2785.19 2588.51 2569.02 5839.1 2483.46 2844.09 2905.6 3372.4 6080.94 7403.38 423.2748684_MZ 1b-Hydroxycholic acid Un 1.0 None None None None 1b-Hydroxycholic acid is a C24 bile acid in the serum of healthy human fetuses, and an usual urinary bile acid in the neonatal and pediatric periods, also excreted in the urine of pregnant women. (PMID: 9483300, 10203155, 1400756). A bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487, 16037564, 12576301, 11907135). C24H40O6, 3a_4b_7a_12a-Tetrahydroxy-5b-cholanoic acid, 3a_6b_7b_12a-Tetrahydroxy-5b-cholanoic acid, 3b_4b_7a_12a-Tetrahydroxy-5b-cholanoic acid None None None 7840.26 3982.0 5889.89 4383.97 4183.71 11607.9 7551.77 17853.4 4944.66 4384.51 8110.75 4725.59 2434.87 24879.4 10010.4 6193.97 16056.0 4388.03 5756.81 7678.76 5884.76 2638.88 5562.4 8241.77 8489.42 4454.66 7150.58 5435.95 7026.8 8061.03 6836.63 4631.28 3438.87 4803.16 5862.9 4137.2 2837.09 4106.57 4407.46 6199.94 5035.75 8983.98 423.4191282_MZ Octacosanoic acid Un 1.0 None None None None Octacosanoic acid is a very-long-chain fatty acid found in human brain and visceral organs (PMID: 2474624). Octacosanoic acid is a higher aliphatic primary acids purified from sugar-cane (Saccharum officinarum L.) wax that has been shown to inhibit platelet aggregation induced ex vivo by addition of agonists to platelet-rich plasma (PRP) of rats, guinea pigs, and healthy human volunteers. (PMID: 5099499). Octacosanoic acid is formed from octacosanol via beta-oxidation. (PMID: 15847942). C28H56O2 None None None 4104.5 4340.5 3778.35 4021.15 4215.51 3495.26 4702.09 6271.36 3405.67 4090.68 4316.67 3679.38 4808.6 4438.49 3575.44 3871.8 6595.94 7065.08 3582.46 5432.0 3430.62 3095.5 3993.24 4344.9 4044.85 3432.38 3828.95 4928.63 3276.61 4613.06 3898.08 3671.06 3705.79 4135.69 3463.06 4113.42 3256.23 3652.87 4351.85 3742.94 3487.53 3859.78 424.1435932_MZ Hyaluronic acid Un 1.0 None None None None Hyaluronic acid (HA), is the most abundant glycosaminoglycan (GAG) in mammalian tissue. It is present in high concentrations in connective tissue, such as skin, vitreous humor, cartilage, and umbilical cord, but the largest single reservoir is the synovial fluid (SF) of the diarthrodial joints, where concentrations of 0.5-4 mg/mL are achieved. Hyaluronic acid, is the major hydrodynamic nonprotein component of joint SF. Its unique viscoelastic properties confer remarkable shock absorbing and lubricating abilities to SF, while its enormous macromolecular size and hydrophilicity serve to retain fluid in the joint cavity during articulation. HA restricts the entry of large plasma proteins and cells into SF but facilitates solute exchange between the synovial capillaries and cartilage and other joint tissues. In addition, HA can form a pericellular coat around cells, interact with proinflammatory mediators, and bind to cell receptors, such as cluster determinant (CD)44 and receptor for hyaluronate-mediated motility (RHAMM), where it modulates cell proliferation, migration, and gene expression. All these physicochemical and biologic properties of HA have been shown to be molecular weight (MW) dependent. The diverse physicochemical properties of HA arise from its unique macromolecular structure. The HA is an exceptionally long (3-30 μm) and unbranched nonsulfated GAG composed of repeating disaccharide units of N-acetylglucosamine, and glucuronic acid glycosidically linked through their respective 1-4 ring positions. Hydroxyl group oxygens at the glucuronyl-1 and glucosamine 3-positions are used for further polymerization of the HA disaccharide units to form chains that, when released from the cell plasma membrane, are of variable length and thus polydispersity. Despite the simplicity of the HA primary structure, this linear polyelectrolyte adopts complex conformations in solution, which engender it with diverse biologic properties. Within the joint cavity, HA molecules are predominately synthesized by the type B synovial cells. (PMID 12219318). C16H27NO12 None None None 6717.87 8027.24 5750.09 9143.64 6177.05 8268.61 8577.42 6919.1 6356.94 7628.69 6651.48 6921.49 7654.2 7800.86 6873.93 9754.5 8870.59 4824.42 6222.33 6631.56 6203.44 5257.63 6979.72 6188.43 7138.16 6169.36 6364.44 7327.6 4769.51 8102.13 8029.46 9268.39 4798.4 4696.96 5871.38 6106.66 5024.8 5358.3 4771.93 6303.16 5412.11 5670.75 424.3425552_MZ Oleoylcarnitine Un 1.0 None None None None Oleoylcarnitine is a long-chain acylcarnitine that accumulates during certain metabolic conditions, such as fasting (PMID: 15653102). C25H47NO4, Vaccenyl carnitine, Elaidic carnitine, 11Z-Octadecenylcarnitine None None None 572.816 398.54 526.201 528.864 389.819 328.205 470.271 706.526 296.873 525.185 425.801 304.915 523.634 578.467 440.788 418.735 921.734 686.427 354.051 618.986 321.998 287.152 393.641 458.662 502.841 415.721 360.938 623.486 386.281 471.348 351.294 461.564 519.85 389.038 345.984 440.902 301.122 342.523 424.246 514.771 433.734 472.84 426.0218464_MZ ADP Un 1.0 None None None None Adenosine diphosphate, abbreviated ADP, is a nucleotide. It is an ester of pyrophosphoric acid with the nucleotide adenine. ADP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase adenine. ADP is the product of ATP dephosphorylation by ATPases. ADP is converted back to ATP by ATP synthases. C10H15N5O10P2, Adenosine 3',5'-diphosphate, dGDP None None None 2197560.0 2754240.0 3294490.0 2047600.0 4097210.0 2620230.0 4590910.0 3785880.0 3307340.0 2172010.0 2876560.0 3043660.0 2703130.0 2373720.0 3818290.0 3016050.0 4614710.0 1580620.0 3174800.0 3168350.0 2800640.0 2437770.0 3041970.0 2336520.0 3439140.0 2493030.0 4153020.0 1936240.0 1800160.0 2293950.0 4272210.0 2711070.0 2878120.0 2450110.0 2097380.0 1693760.0 2778030.0 3510770.0 1571660.0 2055340.0 3153790.0 2358950.0 429.2115968_MZ Risperidone Un 1.0 None None None None Risperidone is an atypical antipsychotic medication approved in 1993. It is most often used to treat delusional psychosis (including schizophrenia), but risperidone (like other atypical antipsychotics) is also used to treat some forms of bipolar disorder, psychotic depression and Tourette syndrome. Generally lower doses are used for autistic spectrum disorders than are used for schizophrenia and other forms of psychosis; Risperidone is a very strong dopamine blocker (antagonist); Risperidone is a very strong dopamine blocker (antagonist); i.e., it inhibits functioning of postsynaptic dopamine receptors. An anxiolytic agent and a serotonin receptor agonist belonging to the azaspirodecanedione class of compounds. Its structure is unrelated to those of the benzodiazepines, but it has an efficacy comparable to diazepam; i.e., it inhibits functioning of postsynaptic dopamine receptors. Risperidone (Belivon, Rispen, Risperdal; in the United States) is an atypical antipsychotic medication. It was approved by the United States Food and Drug Administration (FDA) in 1993. It is most often used to treat delusional psychosis (including schizophrenia), but risperidone (like other atypical antipsychotics) is also used to treat some forms of bipolar disorder, psychotic depression and Tourette syndrome; risperidone has received approval from the Food and Drug Administration (FDA) for symptomatic treatment of irritability in autistic children and adolescents. Risperidone is now the most commonly prescribed antipsychotic medication in the United States. C23H27FN4O2 None None None 14157.4 19485.0 8123.56 20555.4 6922.29 10640.7 7502.68 7967.51 8613.25 11507.6 10237.8 5784.01 4063.06 11748.6 8662.8 9009.27 13837.6 4281.74 6696.29 7033.46 11786.8 5736.2 8848.41 14915.1 9261.89 4075.91 9388.53 5609.94 6074.4 17222.1 9270.15 9951.15 3887.52 8961.0 8777.67 15959.4 7433.72 4796.86 4100.6 13651.8 4651.47 12054.6 429.3359424_MZ 4alpha-carboxy-5alpha-cholesta-8-en-3beta-ol Un 1.0 None None None None C28H46O3 None None None 2023.45 1748.82 1700.84 1954.81 1882.88 1439.25 1982.81 1983.33 1510.76 1671.45 1871.88 1811.2 1939.38 1948.41 1586.62 1702.24 2191.45 2643.41 1448.05 2086.91 1609.99 1532.63 1623.01 2020.77 1844.54 1734.11 1506.86 2063.13 1608.71 1746.29 1767.67 1866.03 1834.07 1707.17 1749.8 1926.29 1422.64 1788.41 1959.38 1776.63 1610.57 1776.58 429.3730913_MZ Alpha-Tocopherol Un 1.0 None None None None Alpha-tocopherol is traditionally recognized as the most active form of vitamin E in humans, and is a powerful biological antioxidant. The measurement of vitamin E activity in international units (IU) was based on fertility enhancement by the prevention of spontaneous abortions in pregnant rats relative to alpha tocopherol. Natural vitamin E exists in eight different forms or isomers, four tocopherols and four tocotrienols. In foods, the most abundant sources of vitamin E are vegetable oils such as palm oil, sunflower, corn, soybean and olive oil. Nuts, sunflower seeds, and wheat germ are also good sources. --Wikipedia. C29H50O2 None None None 91370.5 41924.4 65695.4 20525.3 46441.5 4802.82 82996.5 60565.3 38773.0 20190.3 17905.5 58538.3 50267.1 29614.7 34489.8 23926.8 19828.4 266398.0 36009.9 167666.0 69763.3 69923.3 20132.9 132066.0 79658.8 106775.0 68173.9 95680.5 72426.7 10433.4 65318.6 64732.0 84214.9 50180.5 59312.7 36413.4 39454.0 47104.1 106757.0 41965.3 77522.6 79474.4 430.2953911_MZ 3-Hydroxyhexadecadienoylcarnitine Un 1.0 None None None None none C23H41NO5 None None None 1429.62 1363.17 1340.07 1375.46 1194.54 1428.56 1130.64 1174.78 1124.39 1110.86 1388.3 1139.42 776.247 1504.2 1114.24 1078.14 1666.33 1249.67 906.542 1318.46 1181.53 831.613 1290.57 1252.74 1128.74 1037.2 1041.79 1674.21 1087.19 1470.07 1233.47 782.846 981.294 1253.92 1114.6 1347.97 933.641 1043.51 862.645 1370.82 992.086 1134.65 431.3517954_MZ 13'-Hydroxy-gama-tocopherol Un 1.0 None None None None C28H48O3 None None None 1615.34 1763.78 1644.83 1718.89 1824.49 1409.77 1732.18 1690.71 1584.59 1582.84 2097.38 1918.55 1340.04 1979.44 1463.88 1523.85 1655.59 2297.91 1353.01 1700.7 1461.68 1640.15 1618.23 1715.59 1725.72 1790.63 1534.92 1893.93 1620.74 1764.16 1403.0 1403.66 2082.97 1464.35 1341.27 1519.12 1321.52 2072.44 1504.96 1652.89 1376.33 1384.69 433.2378993_MZ LysoPhosphatidylcholine with formula C21H39O7P Un 1.0 None None None None LPA(0:0/18:2(9Z,12Z)) is a lysophosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. Lysophosphatidic acids can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. Fatty acids containing 16 and 18 carbons are the most common. Lysophosphatidic acid is the simplest possible glycerophospholipid. It is the biosynthetic precursor of phosphatidic acid. Although it is present at very low levels only in animal tissues, it is extremely important biologically, influencing many biochemical processes. In particular, lysophosphatidic acid is an intercellular lipid mediator with growth factor-like activities, and is rapidly produced and released from activated platelets to influence target cells. 1-Palmitoyl lysophosphatidic acid is the major component of lysophosphatidic acid (LPA) in plasma, and is in a reduced ratio in individuals with gynecological cancers (PMID 11585410). LPA is a pluripotent lipid mediator controlling growth, motility, and differentiation, that has a strong influence on the chemotaxis and ultrastructure of human neutrophils (PMID 7416233). In serum and plasma, LPA is mainly converted from lysophospholipids, whereas in platelets and some cancer cells it is converted from phosphatidic acid. In each pathway, at least two phospholipase activities are required: phospholipase A1 (PLA1)/PLA2 plus lysophospholipase D (lysoPLD) activities are involved in the first pathway and phospholipase D (PLD) plus PLA1/PLA2 activities are involved in the second pathway. (PMID 15271293). C21H39O7P None None None 11777.1 10896.6 6747.31 12990.7 7383.51 9945.7 10011.3 9134.17 8827.22 8751.63 8828.58 6399.16 7302.07 10668.6 8153.58 7973.43 12339.5 8489.39 7624.77 8805.0 9094.67 5546.15 9379.04 11304.3 9299.86 6337.33 7619.21 7704.2 5218.6 13391.3 9162.24 8088.35 4899.56 8175.41 5632.34 11305.1 6946.43 5476.95 4619.85 9837.34 8645.23 9101.57 433.3312290_MZ 3a_7a_12a-Trihydroxy-5b-cholestan-26-al Un 1.0 None None None None 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestan-26-al is an intermediate in bile acid biosynthesis. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487, 16037564, 12576301, 11907135). 3a,7a,12a-trihydroxy-5b-cholestane-27-al is an enzymatically generated intermediate in the oxidation process of 5b-cholestane-3a,7a,12a,27-tetrol into 3a,7a,12a-trihydroxy-5b-cholestanoic acid in liver mitochondria. Mitochondrial sterol 27-hydroxylase (EC 1.14.13.60) appears to perform multiple monooxygenations in this conversion. (PMID: 8496170). C27H46O4, 3a_7a-Dihydroxycoprostanic acid None None None 4088.43 4145.71 3397.38 4108.86 4319.54 4924.45 3978.99 4202.6 3530.55 4175.27 4419.66 3846.6 2905.44 4423.49 4812.58 3848.74 4230.26 4750.56 3179.0 4590.78 3708.9 3474.58 3932.55 4000.44 4271.49 4200.4 4042.28 4627.72 3423.42 4339.21 3830.51 3735.1 3857.2 3620.01 3987.52 3509.73 3290.9 3727.83 3573.93 3796.01 3233.01 3522.18 434.3292828_MZ 2-Hydroxyhexadecanoylcarnitine Un 1.0 None None None None C23H45NO5, 3-Hydroxyhexadecanoylcarnitine None None None 1150.33 1018.54 1099.88 1145.79 1043.41 1328.47 1148.51 1082.11 886.871 1229.22 1039.69 1125.65 911.444 1005.83 1222.79 838.482 1009.85 1084.25 760.072 1135.47 991.198 853.811 1070.0 1061.53 1039.73 1210.95 856.453 1345.16 1064.73 1125.86 877.803 920.556 973.226 910.184 1063.64 952.747 983.81 919.295 1088.43 967.674 826.854 948.023 435.2494479_MZ DHAP(18:0) Un 1.0 None None None None DHAP(18:0) is the octadecanoyl derivative of dihydroxyacetone phosphate. It is also known as an alkyl-DHAP. This compound is formed by octadecanoic acid reacting with DHAP. Alkyl-DHAPs are intermediates in the synthesis of ether phospholipids. The initial steps of ether phospholipid biosynthesis take place in peroxisomes. Alkyl-dihydroxyacetonephosphate synthase is the peroxisomal enzyme that actually introduces the ether linkage. Levels of Alkyl-DHAP have been found to be strongly reduced in human fibroblasts derived from Zellweger syndrome and rhizomelic chondrodysplasia punctata patients. Four other enzymes are known to be involved in the metabolism of acyl-DHAP and alkyl-DHAP. These include: acyl-DHAP/alkyl-DHAP oxidoreductase, DHAP acyltransferase, alkyl-DHAP phosphohydrolase, and a dinitrofluorobenzene-insensitive acyl-DHAP acylhydrolase. Dihydroxyacetone phosphate (DHAP) is a biochemical compound primarily involved in the glycolysis metabolic pathway. DHAP is also the product of the dehydrogenation of L-glycerol-3-phosphate which is part of the entry of glycerol (sourced from triglycerides) into the glycolytic pathway. Conversely, reduction of glycolysis-derived DHAP to L-glycerol-3-phosphate provides adipose cells with the activated glycerol backbone they require to synthesize new triglycerides. Both reactions are catalyzed by the enzyme glycerol 3-phosphate dehydrogenase with NAD+/NADH as cofactor. DHAP may be referred to as glycerone phosphate in older texts. 1-Octadecyl-glycerone-3-phosphate is an intermediate in Ether lipid metabolism. DHAP(18:0) or 1-Octadecanoyl-glycerone-3-phosphate is the precursor to 1-Octadecyl-glycerone-3-phosphate DHAP(18:0e) which is generated via alkylglycerone phosphate synthase (EC: 2.5.1.26). Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. Ether lipids are called plasmalogens (1-O-1'-alkenyl-2-acylglycerophospholipids) if these are glycerol-containing phospholipids with an unsaturated O-(1-alkenyl) (vinyl ether) group at the first position on the glycerol chain. Plasmalogens as well as some 1-O-alkyl lipids are ubiquitous and sometimes major parts of the cell membranes in mammals and anaerobic bacteria. In archaea, ether lipids are the major polar lipids in the cell envelope and their abundance is one of the major characteristics that separate this group of prokaryotes from the bacteria. In these cells, diphytanylglycerolipids or bipolar macrocyclic tetraethers can form covalently linked 'bilayers'. (Wikipedia) C21H41O7P, Lysophosphatidic acid with formula C21H41O7P None None None 14072.6 15100.6 14253.4 15724.4 18941.4 16533.6 16837.4 19055.3 17787.2 14536.8 20047.3 20088.3 16492.2 18594.1 16057.4 13173.5 16329.0 19375.0 11281.7 17908.9 13575.4 13732.2 16662.7 13135.1 16416.7 17880.6 14930.0 18394.2 15018.4 14635.3 15572.1 13068.9 18196.3 12280.9 12431.7 15536.1 13177.9 17340.7 9173.39 16018.2 17261.7 14684.3 437.4354052_MZ Nonacosanoic acid Un 1.0 None None None None Nonacosanoic acid is a normal human fatty acid found in many tissues as constituents of cceramides (the major component of the stratum corneum) (PMID: 12190865), in lipids in normal brain white matter (PMID: 8515276), and the sebaceous follicle (PMID: 2940302). C29H58O2 None None None 2304.36 2139.42 1787.3 1744.99 2041.81 1814.55 2560.87 3019.47 1473.91 1828.15 1936.6 1916.34 2426.18 2457.59 1729.7 1797.09 3297.63 3177.49 1725.81 2645.71 1607.43 1178.3 2041.11 2013.59 1904.61 1424.02 1713.71 2490.32 1433.88 2395.99 2099.2 1700.34 1489.72 1684.1 1534.74 1823.05 1406.14 1636.59 2349.01 1841.97 2032.06 1749.84 440.1499424_MZ Folic acid Un 1.0 None None None None Folic acid is a member of the vitamin B family that stimulates the hematopoietic system. It is present in the liver and kidney and is found in mushrooms, spinach, yeast, green leaves, and grasses (poaceae). Folic acid, being biochemically inactive, is converted to tetrahydrofolic acid and methyltetrahydrofolate by dihydrofolate reductase. These folic acid congeners are transported across cells by receptor-mediated endocytosis where they are needed to maintain normal erythropoiesis, synthesize purine and thymidylate nucleic acids, interconvert amino acids, methylated tRNA, and generate and use formate. Folic acid is used in the treatment and prevention of folate deficiencies and megaloblastic anemia. C19H19N7O6 None None None 3936.39 3598.09 3521.22 3906.58 3695.96 5604.49 3851.5 3113.58 2961.38 3704.62 3762.98 3070.33 2253.81 4244.82 3731.15 5190.18 4032.63 2293.7 2905.13 3313.2 3493.43 2694.82 4169.69 3560.89 3347.38 2949.64 3819.98 3163.87 2743.61 4510.0 3575.99 4324.02 2637.38 2750.23 3673.55 3451.31 2610.0 2890.17 1988.73 3406.79 2463.23 2683.47 443.3517388_MZ 3-beta-Hydroxy-4-beta-methyl-5-alpha-cholest-7-ene-4-alpha-carboxylate Un 1.0 None None None None 3-beta-Hydroxy-4-beta-methyl-5-alpha-cholest-7-ene-4-alpha-carboxylate is a steroid biosynthesis intermediate. It is a substrate for sterol-4-alpha-carboxylate 3-dehydrogenase (EC 1.1.1.170) and participates in the following reaction: 3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carboxylate + NAD(P)+ = 4alpha-methyl-5alpha-cholest-7-en-3-one + CO2 + NAD(P)H. It is also produced by methylsterol hydroxylase. It participates in the following reaction: 3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carbaldehyde + NAD(P)H + H+ + O2 = 3beta-hydroxy-4beta-methyl-5alpha-cholest-7-ene-4alpha-carboxylate + NAD(P)+ + H2O. C29H48O3, 4alpha-carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol None None None 2654.31 2474.02 2527.5 2318.74 2462.32 1963.2 2666.95 2751.11 2242.16 2189.03 3041.79 2719.65 2483.29 2611.86 2283.71 1996.52 2583.84 3831.77 1985.9 3332.32 2220.43 2318.92 2341.91 2588.76 2664.89 2386.67 2259.27 3072.95 2411.75 2714.84 2296.97 2025.7 2834.64 2558.47 2122.28 2479.19 1975.25 2717.67 2704.35 2362.64 1994.84 2428.93 444.2502275_MZ Lysophosphatidylethanolamine with formula C19H40NO7P Un 1.0 None None None None LysoPE(0:0/14:0) is a lysophosphatidylethanolamine or a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylethanolamines (LPEs) can function as plant growth regulators with several diverse uses. (LPEs) are approved for outdoor agricultural use to accelerate ripening and improve the quality of fresh produce. They are also approved for indoor use to preserve stored crops and commercial cut flowers. As a breakdown product of phosphatidylethanolamine (PE), LPE is present in cells of all organisms. C19H40NO7P None None None 3273.88 3064.23 2605.93 3604.16 2490.59 3561.92 2756.25 2923.06 3017.62 2600.15 3633.29 2303.28 1642.67 4689.11 2814.93 2568.88 3559.79 2024.15 2248.5 2418.21 2998.74 2152.36 6096.67 3581.12 2887.85 2080.46 2717.43 2714.65 2028.74 3568.84 2537.19 2263.78 1764.63 2579.68 2361.14 3376.55 2244.73 1929.41 1438.2 3332.27 2512.53 3048.04 445.3678756_MZ 13'-hydroxy-alpha-tocopherol Un 1.0 None None None None 13'-hydroxy-alpha-tocopherol is the precursor in dehydrogenation to 13'-carboxy-alpha-tocopherol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate. The tocopherols ( a-tocopherol , b-tocopherol ,r-tocopherol and d-tocopherol ) and their corresponding tocotrienols are synthesized by plants and have vitamin E antixoidant activity (see pathway vitamin E biosynthesis ). They differ in the number and location of methyl groups on the chromanol ring. The naturally occurring form of a-tocopherol is (2R,4'R,8'R)-a-tocopherol (synonym (R,R,R)-a-tocopherol). Synthetic a-tocopherols are a racemic mixture of eight different R and S stereoisomers. Only the 2R forms are recognized as meeting human requirements. The in vivo function of vitamin E is to scavenge peroxyl radicals via its phenolic (chromanol) hydroxyl group, thus protecting lipids against free radical-catalyzed peroxidation. The tocopheryl radical formed can then be reduced by reductants such as L-ascorbate. Other major products of a-tocopherol oxidation include α-tocopherylquinone and epoxy-a-tocopherols. The metabolites a-tocopheronic acid and its lactone, known as the Simon metabolites, are generally believed to be artefacts. In addition to these oxidation products, the other major class of tocopherol metabolites is the carboxyethyl-hydroxychromans.These metabolites are produced in significant amounts in response to excess vitamin E ingestion. Vitamin E is fat-soluble and its utilization requires intestinal fat absorption mechanisms. It is secreted from the intestine into the lymphatic system in chylomicrons which subsequently enter the plasma. Lipolysis of these chylomicrons can result in delivery of vitamin E to tissues, transfer to high-density lipoproteins (and subsequently to other lipoproteins via the phospholipid exchange protein), or retention in chylomicron remnants. These remnants are taken up by the liver. Natural (R,R,R)-α-tocopherol and synthetic 2R-α-tocopherols are then preferentially secreted from the liver into plasma as a result of the specificity of the α-tocopherol transfer protein. This protein, along with the metabolism of excess vitamin E in the liver and excretion into urine and bile, mediate the supply of a-tocopherol in plasma and tissues. C29H50O3 None None None 7806.29 7303.45 10257.8 7108.96 10442.1 6407.01 11906.6 6802.42 8378.58 8499.5 9633.47 12800.7 6679.11 9416.34 7890.59 5701.46 6656.75 9689.88 7801.26 10351.5 6331.12 8929.82 7702.4 6769.91 11686.6 10899.0 7418.58 9869.48 8214.24 7317.89 6909.3 8062.86 15250.4 6222.47 6178.99 6365.92 7379.85 12572.9 14391.0 7247.94 6987.18 7258.37 446.0186989_MZ Adenosine phosphosulfate Un 1.0 None None None None Adenosine phosphosulfate (also known as APS) is the initial compound formed by the action of ATP sulfurylase (or PAPS synthetase) on sulfate ions after sulfate uptake. PAPS synthetase 1 is a bifunctional enzyme with both ATP sulfurylase and APS kinase activity, which mediates two steps in the sulfate activation pathway. The first step is the transfer of a sulfate group to ATP to yield adenosine 5'-phosphosulfate (APS), and the second step is the transfer of a phosphate group from ATP to APS yielding 3'-phosphoadenylylsulfate (PAPS). In mammals, PAPS is the sole source of sulfate; APS appears to be only an intermediate in the sulfate-activation pathway. C10H14N5O10PS None None None 6214.51 7482.7 6500.3 6357.88 6846.55 8078.82 7238.78 6472.59 6237.73 7187.0 6370.05 7073.16 7103.44 6573.71 7072.63 8864.48 6195.42 7425.76 7505.74 6333.73 6297.86 6254.92 6830.99 6137.99 6936.29 6698.78 7057.83 6796.75 6992.97 6977.65 6564.23 6941.27 6280.82 6109.85 7818.74 7098.05 6684.06 6894.74 5446.4 7152.75 6860.08 6655.39 446.0831902_MZ Se-Adenosylselenomethionine Un 1.0 None None None None Se-Adenosylselenomethionine is an intermediate in Selenoamino acid metabolism. Se-Adenosylselenomethionine is converted from Selenomethionine via the enzyme S-adenosylmethionine synthetase (EC 2.5.1.6). It is then. converted to Se-Adenosylselenohomocysteine via the enzyme Transferases (EC 2.1.1.-). C15H23N6O5Se None None None 4162.56 5876.77 4555.65 3535.19 4468.02 5035.16 4956.68 4247.28 4190.35 3933.63 4172.38 4644.55 4227.43 3944.44 4414.99 4590.75 4623.21 4447.48 4577.57 4468.49 5183.92 4357.73 4228.61 4408.52 4254.96 4099.82 5686.63 4126.19 3947.83 5290.6 4494.38 3641.06 3608.05 4073.47 4546.22 3914.82 4074.31 4266.79 2822.48 4390.81 3877.38 4160.28 447.2105927_MZ 17-alpha-estradiol-3-glucuronide Un 1.0 None None None None 17-alpha-estradiol-3-glucuronide is a natural human metabolite of 17alpha-estradiol generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys. C24H32O8, 17-beta-estradiol glucuronide, 2-Methoxyestrone 3-glucuronide None None None 8603.84 6648.72 5033.93 7737.12 5183.03 7884.84 5810.04 5534.11 5327.06 7287.6 6221.94 4752.72 3950.8 7625.2 6052.09 6620.11 7092.59 5215.43 4641.2 6162.22 5982.39 4384.27 6303.41 6820.3 5752.73 4330.29 5652.93 5260.96 4292.65 10319.8 5499.88 6321.91 4177.11 5500.48 5103.25 6077.69 4360.29 4213.52 4041.61 6133.98 5222.15 5320.28 447.4047491_MZ Tetrahymanol Un 1.0 None None None None Tetrahymanol is involved in the terpenoid biosynthesis pathway. Tetrahymanol is produced from squalene. C30H52O, 24_25-Dihydrolanosterol None None None 258.362 269.284 202.478 364.16 206.942 188.044 374.485 247.975 140.509 349.728 351.512 246.234 170.758 317.436 254.075 626.041 344.684 487.167 179.611 307.453 224.752 182.591 269.663 211.316 524.69 216.506 231.556 271.755 217.559 223.158 330.401 895.738 186.281 250.563 236.608 297.17 191.001 269.611 406.667 257.532 340.235 266.151 448.3065689_MZ Chenodeoxyglycocholic acid Un 1.0 None None None None Chenodeoxyglycocholic acid is a glycine conjugated bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487, 16037564, 12576301, 11907135). C26H43NO5, Glycoursodeoxycholic acid None None None 1900.28 1496.64 1507.03 1771.46 2305.15 1774.98 1895.64 2256.31 1564.61 1383.09 2009.39 2626.42 1202.39 1940.2 1817.4 1808.2 1761.38 1510.86 2836.84 1820.45 1714.78 1169.26 1729.79 1670.58 1823.93 1605.87 2823.71 1779.52 1448.23 1775.39 1864.88 1517.88 1340.94 1295.66 1806.57 1746.27 1277.36 1766.2 1315.79 1915.37 1379.57 2473.98 450.2577624_MZ Lysophosphatidylethanolamine with formula C21H42NO7P Un 1.0 None None None None LysoPE(0:0/16:1(9Z)) is a lysophosphatidylethanolamine or a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylethanolamines (LPEs) can function as plant growth regulators with several diverse uses. (LPEs) are approved for outdoor agricultural use to accelerate ripening and improve the quality of fresh produce. They are also approved for indoor use to preserve stored crops and commercial cut flowers. As a breakdown product of phosphatidylethanolamine (PE), LPE is present in cells of all organisms. C21H42NO7P None None None 5105.62 4748.34 3942.13 5625.1 6352.83 5682.03 5480.5 5313.04 7270.67 4203.41 5906.25 6144.58 2983.69 6615.54 5823.32 5197.54 7908.15 4490.96 5052.04 4226.0 4952.18 4616.82 5295.77 4978.31 5520.97 4851.35 5820.93 4375.11 3221.43 5964.33 6243.99 4829.39 4522.31 4729.11 3884.25 6856.75 4150.05 4833.55 2315.84 5058.95 4183.26 4182.06 451.2045854_MZ 20-Oxo-leukotriene E4 Un 1.0 None None None None 20-oxo-leukotriene E4 is a metabolite through lipid oxidation of Leukotriene E4 (LTE4).Leukotriene E4 (LTE4) is a cysteinyl leukotriene. Cysteinyl leukotrienes (CysLTs) are a family of potent inflammatory mediators that appear to contribute to the pathophysiologic features of allergic rhinitis. Nasal blockage induced by CysLTs is mainly due to dilatation of nasal blood vessels, which can be induced by the nitric oxide produced through CysLT1 receptor activation. LTE4, activate contractile and inflammatory processes via specific interaction with putative seven transmembrane-spanning receptors that couple to G proteins and subsequent intracellular signaling pathways. LTE4 is metabolized from leukotriene C4 in a reaction catalyzed by gamma-glutamyl transpeptidase and a particulate dipeptidase from kidney. (PMID: 12607939, 12432945, 6311078). Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways. C23H34NO6S None None None 3505.82 3640.6 3692.69 5363.36 4078.75 4734.57 4156.78 4279.97 3244.27 4409.64 3639.63 2770.55 2939.64 3826.21 4897.23 5726.95 5773.98 2766.98 3296.23 3786.22 3458.93 2570.22 3784.46 3628.68 3981.21 2621.83 4312.56 3218.18 2722.78 4208.97 4171.09 4933.94 2311.36 2864.42 3346.72 3772.54 2601.09 2384.94 2430.01 4185.13 3245.98 3577.72 454.3960844_MZ Arachidyl carnitine Un 1.0 None None None None Arachidyl carnitine is an acylcarnitine. Numerous disorders have been described that lead to disturbances in energy production and in intermediary metabolism in the organism which are characterized by the production and excretion of unusual acylcarnitines. A mutation in the gene coding for carnitine-acylcarnitine translocase or the OCTN2 transporter aetiologically causes a carnitine deficiency that results in poor intestinal absorption of dietary L-carnitine, its impaired reabsorption by the kidney and, consequently, in increased urinary loss of L-carnitine. Determination of the qualitative pattern of acylcarnitines can be of diagnostic and therapeutic importance. The betaine structure of carnitine requires special analytical procedures for recording. The ionic nature of L-carnitine causes a high water solubility which decreases with increasing chain length of the ester group in the acylcarnitines. Therefore, the distribution of L-carnitine and acylcarnitines in various organs is defined by their function and their physico-chemical properties as well. High performance liquid chromatography (HPLC) permits screening for free and total carnitine, as well as complete quantitative acylcarnitine determination, including the long-chain acylcarnitine profile. (PMID: 17508264, Monatshefte fuer Chemie (2005), 136(8), 1279-1291., Int J Mass Spectrom. 1999;188:39-52.). C27H53NO4 None None None 1289.67 1529.22 1810.74 1905.1 1428.46 1399.93 1601.57 2460.94 1455.56 1501.14 1585.49 1437.37 1340.17 1405.2 1702.72 2107.01 2920.48 1690.87 1327.64 1906.49 1278.81 1109.67 1469.12 1607.58 1733.6 1444.59 1511.4 1536.61 1215.55 1484.62 1874.76 2202.93 1291.41 1493.28 1367.79 1456.97 1282.52 1574.33 1782.68 1494.34 1406.16 1424.92 455.0899139_MZ Flavin Mononucleotide Un 1.0 None None None None Flavin mononucleotide (FMN), or riboflavin-5‰Û_-phosphate, is a biomolecule produced from riboflavin (vitamin B2) by the enzyme riboflavin kinase and functions as prosthetic group of various oxidoreductases including NADH dehydrogenase as well as cofactor in biological blue-light photo receptors. During the catalytic cycle, the reversible interconversion of oxidized (FMN), semiquinone (FMNH‰Û¢) and reduced (FMNH2) forms occurs in the various oxidoreductases. FMN is a stronger oxidizing agent than NAD and is particularly useful because it can take part in both one- and two-electron transfers. Flavin mononucleotide is also used as an orange-red food colour additive. It is the principal form in which riboflavin is found in cells and tissues. C17H21N4O9P None None None 15214.1 18524.0 17394.9 11864.9 20051.1 16489.6 19901.7 14261.4 17198.2 13480.7 13742.6 17279.4 16783.8 15401.1 16839.1 17761.4 19292.5 19749.6 17914.5 16074.8 16953.7 11325.6 16052.0 17202.1 19368.4 14306.1 22892.7 16712.3 14459.5 12899.8 17314.3 16132.9 19643.4 14458.8 16807.3 14863.9 15199.8 13412.3 9474.28 17490.2 22266.6 16176.3 460.3286873_MZ Galactosylsphingosine Un 1.0 None None None None C24H47NO7, Glucosylsphingosine None None None 12191.8 16366.8 12618.9 13444.5 13644.2 9830.81 13645.3 16446.3 12303.4 13094.6 16592.9 13861.6 12510.7 12976.7 10491.6 13627.6 12185.1 30116.6 9594.68 19115.0 12582.2 11533.6 10659.1 14302.7 12396.5 12195.2 11344.6 17839.4 11926.5 15450.0 12400.8 13279.1 13805.2 16442.0 13301.2 15816.9 8384.95 15693.5 13317.3 13093.3 9932.12 11912.2 462.0594119_MZ Chondroitin sulfate Un 1.0 None None None None C13H21NO15S None None None 7375.32 7860.48 14029.9 6233.37 23141.7 8845.06 17761.1 17245.8 13185.2 8511.38 8177.44 14024.6 16117.6 7969.26 20627.1 13783.5 20177.6 8933.26 14379.3 14541.5 10524.5 9128.26 11868.6 7448.45 17487.9 8980.12 19738.1 10825.1 7677.05 8233.54 13970.3 12807.0 9861.23 7792.79 8035.97 6424.59 9162.43 15743.5 13233.5 9188.3 19540.5 9982.21 463.2850229_MZ 1_25-Dihydroxyvitamin D3-26_23-lactone Un 1.0 None None None None C27H40O5 None None None 7759.65 6906.0 7428.81 6644.23 6663.11 7764.15 7416.55 7814.93 6535.15 5983.2 7670.14 8752.07 9445.01 7373.89 6007.27 6269.97 8752.82 10755.2 5253.31 8485.54 6450.97 6142.97 7618.99 5852.23 7253.32 6938.9 5999.24 8627.39 7821.88 6742.69 8410.02 6393.57 7203.71 5803.87 5715.03 7149.92 6115.22 7191.45 5223.92 6976.03 9672.3 6028.53 464.3003578_MZ 3a_7b_12a-Trihydroxyoxocholanyl-Glycine Un 1.0 None None None None 3a,7b,12a-Trihydroxyoxocholanyl-Glycine is an acyl glycine and a bile acid-glycine conjugate. It is a secondary bile acid produced by the action of enzymes existing in the microbial flora of the colonic environment. In hepatocytes, both primary and secondary bile acids undergo amino acid conjugation at the C-24 carboxylic acid on the side chain, and almost all bile acids in the bile duct therefore exist in a glycine conjugated form (PMID:16949895). 3a,7b,12a-Trihydroxyoxocholanyl-Glycine is a specific ketonic bile acid found in the urine of infants during the neonatal period. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. C26H43NO6, Glycocholic acid None None None 7845.59 4018.34 4291.3 7322.2 8343.47 8754.17 10262.7 10011.7 3041.15 4563.38 7831.73 11469.0 3853.3 7202.89 5324.23 3687.37 7712.61 4387.52 10552.3 8654.65 6737.06 6045.27 5830.38 6635.79 9382.62 3793.24 10680.0 4584.83 10235.5 8140.17 6716.08 4869.48 4176.4 2629.63 8286.53 6169.24 4393.78 6094.28 4467.5 11146.0 6870.6 14722.9 465.3034425_MZ Cholesterol sulfate Un 1.0 None None None None Cholesterol sulfate is a sterol sulfate in human plasma. It is a component of cell membrane and has a regulatory function. It has a stabilizing function on the membrane, supports platelet adhesion and involves in signal transduction. (PMID 12730293). C27H46O4S None None None 121562.0 141726.0 125329.0 108282.0 92401.0 122243.0 150511.0 73916.1 81145.5 99197.0 63773.3 235575.0 113828.0 100079.0 95943.8 111179.0 118082.0 157081.0 69469.1 158119.0 106488.0 95093.1 106410.0 88034.5 120002.0 154294.0 120383.0 187153.0 129718.0 129361.0 155335.0 136450.0 106193.0 64808.3 84487.2 100251.0 96314.4 117428.0 143222.0 90113.9 120873.0 76442.2 468.0680712_MZ 2-(a-Hydroxyethyl)thiamine diphosphate Un 1.0 None None None None C14H23N4O8P2S None None None 3182.12 3245.66 3229.1 2558.49 3381.1 3848.84 3437.81 3118.15 2806.43 3162.46 2796.92 3581.1 3558.64 2775.25 3429.09 4646.98 2808.69 3990.67 3336.23 3681.24 3053.08 2748.76 2950.62 2899.11 3155.41 2769.8 3698.13 3288.45 2863.62 3252.1 3406.12 3147.94 2945.09 2673.73 2878.83 3228.82 2850.91 3398.83 2385.61 3046.77 3850.35 3188.01 469.3519518_MZ Tricaprylic glyceride with formula C27H50O6 Un 1.0 None None None None TG(8:0/8:0/8:0) or tricaprylic glyceride is a trioctanoic acid triglyceride or medium chain triglyceride. Triglycerides (TGs) are also known as triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.e. fatty acid tri-esters of glycerol). TGs may be divided into three general types with respect to their acyl substituents. They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. TG(8:0/8:0/8:0), in particular, consists of one chain of octanoic acid at the C-1 position, one chain of octanoic acid at the C-2 position and one chain of octanoic acid at the C-3 position. TGs are the main constituent of vegetable oil and animal fats. TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) with the help of lipases and bile secretions, which can then move into blood vessels. The triglycerides are rebuilt in the blood from their fragments and become constituents of lipoproteins, which deliver the fatty acids to and from fat cells among other functions. Various tissues can release the free fatty acids and take them up as a source of energy. Fat cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain cannot utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when it is broken down. (www.cyberlipid.org, www.wikipedia.org)TAGs can serve as fatty acid stores in all cells, but primarily in adipocytes of adipose tissue. The major building block for the synthesis of triacylglycerides, in non-adipose tissue, is glycerol. Adipocytes lack glycerol kinase and so must use another route to TAG synthesis. Specifically, dihydroxyacetone phosphate (DHAP), which is produced during glycolysis, is the precursor for TAG synthesis in adipose tissue. DHAP can also serve as a TAG precursor in non-adipose tissues, but does so to a much lesser extent than glycerol. The use of DHAP for the TAG backbone depends on whether the synthesis of the TAGs occurs in the mitochondria and ER or the ER and the peroxisomes. The ER/mitochondria pathway requires the action of glycerol-3-phosphate dehydrogenase to convert DHAP to glycerol-3-phosphate. Glycerol-3-phosphate acyltransferase then esterifies a fatty acid to glycerol-3-phosphate thereby generating lysophosphatidic acid. The ER/peroxisome reaction pathway uses the peroxisomal enzyme DHAP acyltransferase to acylate DHAP to acyl-DHAP which is then reduced by acyl-DHAP reductase. The fatty acids that are incorporated into TAGs are activated to acyl-CoAs through the action of acyl-CoA synthetases. Two molecules of acyl-CoA are esterified to glycerol-3-phosphate to yield 1,2-diacylglycerol phosphate (also known as phosphatidic acid). The phosphate is then removed by phosphatidic acid phosphatase (PAP1), to generate 1,2-diacylglycerol. This diacylglycerol serves as the substrate for addition of the third fatty acid to make TAG. Intestinal monoacylglycerols, derived from dietary fats, can also serve as substrates for the synthesis of 1,2-diacylglycerols. C27H50O6 None None None 2725.73 2176.91 2703.72 2381.96 2375.91 2364.37 2473.81 4041.52 1870.69 2295.79 2518.3 1895.06 2139.52 2417.49 2785.91 2825.29 5016.86 2567.31 1720.19 3009.61 2131.93 1476.48 2276.32 2402.76 2375.86 1854.61 2297.5 2270.92 1779.02 2668.15 2615.79 2467.85 1821.57 2174.28 1830.9 2321.92 1653.38 1690.24 2153.22 2264.77 1679.08 2179.91 473.1877143_MZ Sildenafil Un 1.0 None None None None Sildenafil is a drug used to treat male erectile dysfunction (impotence) and pulmonary arterial hypertension (PAH), developed by the pharmaceutical company Pfizer. It was initially studied for use in hypertension (high blood pressure) and angina pectoris (a form of ischaemic cardiovascular disease). Phase I clinical trials under the direction of Ian Osterloh suggested that the drug had little effect on angina, but that it could induce marked penile erections; Sildenafil is a potent and selective inhibitor of cGMP specific phosphodiesterase type 5 (PDE5) which is responsible for degradation of cGMP in the corpus cavernosum. The molecular structure of sildenafil is similar to that of cGMP and acts as a competitive binding agent of PDE5 in the corpus cavernosum, resulting in more cGMP and better erections. Without sexual stimulation, and therefore lack of activation of the NO/cGMP system, sildenafil should not cause an erection. Other drugs that operate by the same mechanism include tadalafil (Cialis) and vardenafil (Levitra); Sildenafil citrate, sold under the names Viagra, Revatio and generically under various other names, is a drug used to treat male erectile dysfunction (impotence) and pulmonary arterial hypertension (PAH), developed by the pharmaceutical company Pfizer. Viagra pills are blue and diamond-shaped with the words 'Pfizer' on one side, and 'VGR xx' (where xx stands for '25', '50' or '100', the dose of that pill in milligrams) on the other. Its primary competitors on the market are tadalafil (Cialis), and vardenafil (Levitra). C22H30N6O4S None None None 3559.37 3437.77 3824.68 3759.39 3418.88 3640.96 3925.58 4461.03 2829.98 3377.62 3592.67 2979.6 3176.71 3514.58 3961.18 3580.1 5440.38 3496.16 3290.62 3406.83 3245.12 2608.37 3928.13 3977.7 3660.59 2833.89 4091.21 3592.92 2866.38 4491.75 3243.88 3077.19 2382.03 2772.28 2724.16 3549.26 2328.71 2237.83 2255.19 3407.98 3076.12 3535.36 473.2814184_MZ Verapamil Un 1.0 None None None None C27H38N2O4 None None None 100793.0 89392.9 79234.6 98053.6 102999.0 81029.2 129085.0 112708.0 94549.2 85509.9 121289.0 113721.0 133626.0 90868.7 67983.2 59046.6 123281.0 121063.0 71851.3 101101.0 81237.7 68807.1 99000.3 87619.0 83545.6 80746.1 62669.9 105723.0 75801.7 97001.4 73294.4 56457.6 117062.0 71010.0 68138.0 86354.4 65777.8 104366.0 78702.1 94023.5 103869.0 75001.8 473.3252732_MZ 27-Norcholestanehexol Un 1.0 None None None None 27-Norcholestanehexol is a bile alcohol. Bile alcohols have been found to be present as minor components in the bile and urine in healthy subjects. Bile alcohols are end products for cholesterol elimination as well as major biliary constituents; in mammals, cholesterol is metabolized by additional enzymes that ultimately transform it to bile acids. Bile alcohols are preferentially excreted as glucuronides into the urine, which constitute about 10% of total bile acids. The excretion of glucuronidated bile alcohols in urine is suggested to reflect an alternative metabolism of intermediates in the normal biosynthesis of bile acids. (PMID: 6548247, 11718684). C26H46O6 None None None 14912.2 10513.9 9289.26 6835.83 7339.27 11404.0 8549.45 12176.3 6545.9 8038.05 9433.93 9892.5 7131.21 7436.59 7732.78 15442.1 9325.38 7631.8 5244.79 10871.9 10726.8 6625.69 10008.2 11662.6 11286.1 8417.59 9181.51 11573.2 7036.63 15066.1 9035.69 5836.24 7982.65 7565.09 6940.11 6942.22 5704.13 5968.95 3462.32 8550.36 8193.38 7982.78 478.1847716_MZ 5-Methyltetrahydrofolic acid Un 1.0 None None None None 5 methyltetrahydrofolic acid (5-MTHF) is the most biologically active form of the B-vitamin known as folic acid, also known generically as folate. 5-MTHF functions, in concert with vitamin B12, as a methyl-group donor involved in the conversion of the amino acid homocysteine to methionine. Methyl (CH3) group donation is vital to many bodily processes, including serotonin, melatonin, and DNA synthesis. Therapeutically, 5-MTHF is instrumental in reducing homocysteine levels, preventing neural tube defects, and improving vascular endothelial function. Research on folate supplementation suggests it plays a key role in preventing cervical dysplasia and protecting against neoplasia in ulcerative colitis. Folic acid also shows promise as part of a nutritional protocol to treat vitiligo, and may reduce inflammation of the gingiva. Furthermore, certain neurological, cognitive, and psychiatric presentations may be secondary to folate deficiency. Such presentations include depression, peripheral neuropathy, myelopathy, restless legs syndrome, insomnia, dementia, forgetfulness, irritability, endogenous depression, organic psychosis, and schizophrenia-like syndromes. After ingestion, the process of conversion of folic acid to the metabolically active coenzyme forms is relatively complex. Synthesis of the active forms of folic acid requires several enzymes, adequate liver and intestinal function, and adequate supplies of riboflavin (B2), niacin (B3), pyridoxine (B6), zinc, vitamin C, and serine. After formation of the coenzyme forms of the vitamin in the liver, these metabolically active compounds are secreted into the small intestine with bile (the folate enterohepatic cycle), where they are reabsorbed and distributed to tissues throughout the body. Human pharmacokinetic studies indicate folic acid has high bioavailability, with large oral doses of folic acid substantially raising plasma levels in healthy subjects in a time and dose dependent manner. Red blood cells (RBCs) appear to be the storage depot for folic acid, as RBC levels remain elevated for periods in excess of 40 days following discontinuation of supplementation. Folic acid is poorly transported to the brain and rapidly cleared from the central nervous system. The primary methods of elimination of absorbed folic acid are fecal (through bile) and urinary. Despite the biochemical complexity of this process, evidence suggests oral supplementation with folic acid increases the body's pool of 5-MTHF in healthy individuals. However, enzyme defects, mal-absorption, digestive system pathology, and liver disease can result in impaired ability to activate folic acid. In fact, some individuals have a severe congenital deficiency of the enzyme Methyl tetrahydrofolate reductase (5-MTHFR), which is needed to convert folic acid to 5-MTHF. Milder forms of this enzyme defect likely interact with dietary folate status to determine risk for some disease conditions. In individuals with a genetic defect of this enzyme (whether mild or severe), supplementation with 5- MTHF might be preferable to folic acid supplementation. (PMID: 17176169). C20H25N7O6 None None None 16557.4 25703.2 34590.1 16252.6 44583.6 50453.1 23368.7 9178.9 13486.8 18078.2 32954.1 10657.1 6030.78 31378.4 44589.7 35779.6 14054.7 7681.07 17809.3 9175.16 27429.8 12836.9 34415.6 32906.7 22465.7 26961.9 54416.1 13012.9 23284.7 20545.0 18330.5 32333.2 19950.2 15364.3 22098.7 13712.0 13773.3 14053.6 7068.66 24350.9 6295.21 12392.2 478.2925340_MZ Lysophosphatidylethanolamine with formula C23H46NO7P Un 1.0 None None None None LysoPE(0:0/18:1(11Z)) is a lysophosphatidylethanolamine or a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylethanolamines (LPEs) can function as plant growth regulators with several diverse uses. (LPEs) are approved for outdoor agricultural use to accelerate ripening and improve the quality of fresh produce. They are also approved for indoor use to preserve stored crops and commercial cut flowers. As a breakdown product of phosphatidylethanolamine (PE), LPE is present in cells of all organisms. C23H46NO7P None None None 26196.9 32883.1 32730.9 44436.6 60956.2 38378.3 49944.2 47684.7 59699.9 27721.5 45401.5 61950.4 35705.0 43389.1 40042.2 38191.9 56659.9 38073.1 36680.6 48585.7 36582.9 47345.4 45512.5 35316.0 43296.7 48933.3 38899.0 39944.6 30589.4 33121.2 49851.2 39363.6 45194.3 35240.3 27826.3 58933.3 35974.3 59254.3 20724.6 42905.4 51642.2 32048.4 481.2422399_MZ 11-beta-hydroxyandrosterone-3-glucuronide Un 1.0 None None None None 11-beta-hydroxyandrosterone-3-glucuronide is a natural human metabolite of 11beta-hydroxyandrosterone generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys. C25H38O9 None None None 6082.1 5891.35 6728.34 6714.29 8215.41 7267.64 7207.98 8121.3 6030.68 5595.67 6492.97 6524.56 5132.33 6789.59 7197.27 7488.09 9583.24 4702.27 5435.26 6463.67 5475.11 4977.02 6644.88 5964.54 6879.43 5799.0 7188.33 5522.29 5183.67 6819.38 7031.81 6230.13 6003.17 5232.26 4972.33 5711.98 4998.79 5871.01 4353.43 6292.18 5950.06 5917.1 481.9773000_MZ Cytidine triphosphate Un 1.0 None None None None Cytidine 5'-(tetrahydrogen triphosphate) or CTP is a cytosine nucleotide containing three phosphate groups esterified to a ribose moiety at the 5' position. CTP is integral to the synthesis or mRNA, rRNA and tRNA through RNA polymerases. Cytidine triphosphate (CTP) is also critical to the synthesis of phosphatidylcholine via the enzyme CTP: phosphocholine cytidyltransferase. This reaction is the rate-limiting step in the synthesis of phosphatidylcholine. C9H16N3O14P3 None None None 29016.6 30417.4 31685.4 29230.5 34283.1 29935.3 37860.0 38368.0 31429.6 26979.9 30395.7 31294.5 29423.7 29285.7 33605.0 31210.3 34484.5 31969.0 30759.6 33803.6 31914.5 27091.7 30202.6 30025.5 32454.3 29630.1 34566.8 28789.9 28326.6 30218.5 36822.5 26309.8 29398.5 29714.2 31786.6 28345.1 28858.6 30879.6 23608.0 29879.4 30840.9 29832.2 482.9661752_MZ Uridine triphosphate Un 1.0 None None None None Uridine 5'-(tetrahydrogen triphosphate). A uracil nucleotide containing three phosphate groups esterified to the sugar moiety. Uridine triphosphate has the role of a source of energy or an activator of substrates in metabolic reactions, like that of adenosine triphosphate, but more specific. When Uridine triphosphate activates a substrate, UDP-substrate is usually formed and inorganic phosphate is released. (Wikipedia). C9H15N2O15P3 None None None 34381.2 38295.0 42212.6 21195.8 51828.4 34856.5 59862.0 60405.9 33132.6 24679.7 42445.2 45300.4 37449.3 41080.8 45738.2 42996.6 54377.0 23795.3 37673.5 54861.6 39019.0 25683.7 35933.5 34475.1 44925.3 37150.5 50072.8 25227.6 21267.7 35770.0 75111.3 32860.2 41335.2 35923.4 21408.4 26190.3 26998.8 38237.0 20260.0 30921.3 38954.8 35606.0 484.2714257_MZ LysoPhosphatidylcholine (14:1(9Z)) Un 1.0 None None None None LysoPC(14:1(9Z)) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(14:1(9Z)), in particular, consists of one chain of myristoleic acid at the C-1 position. The myristoleic acid moiety is derived from milk fats. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. In blood plasma significant amounts of lysophosphatidylcholine are formed by a specific enzyme system, lecithin:cholesterol acyltransferase (LCAT), which is secreted from the liver. The enzyme catalyzes the transfer of the fatty acids of position sn-2 of phosphatidylcholine to the free cholesterol in plasma, with formation of cholesterol esters and lysophosphatidylcholine. Lysophospholipids have a role in lipid signaling by acting on lysophospholipid receptors (LPL-R). LPL-R's are members of the G protein-coupled receptor family of integral membrane proteins. C22H44NO7P None None None 6664.61 4243.56 5410.59 5204.4 7176.07 6482.27 6443.03 6156.42 4750.13 4521.09 5796.43 7620.07 3694.61 8147.42 6563.91 5976.76 7041.88 6040.11 5531.28 6252.82 8680.51 5359.34 5455.99 5148.47 7975.59 5507.55 8175.84 5912.25 6587.62 7584.75 6666.3 4866.98 4948.4 3883.18 5066.28 5479.18 4733.8 6090.32 3815.4 6605.52 7499.49 10892.0 489.0175979_MZ 1-Phosphatidyl-1D-myo-inositol 3-phosphate Un 1.0 None None None None 1-Phosphatidyl-1D-myo-inositol 3-phosphate is a substrate for FYVE finger-containing phosphoinositide kinase and Neutrophil cytosol factor 4. C11H20O16P2 None None None 5504.97 7775.11 7099.32 9881.64 6890.64 7408.32 6688.9 5362.53 6556.8 7752.57 7099.13 7809.17 6236.27 6356.97 7967.91 7599.62 7174.96 5842.16 7310.16 5809.23 6621.55 7305.82 6695.65 6315.75 6837.06 7660.07 7839.1 6895.6 6713.59 6750.55 7195.75 9198.73 5897.96 6559.61 7818.55 6746.0 6904.13 7512.1 5042.72 7328.42 6571.4 6354.75 489.3219718_MZ Glycyrrhetinic acid Un 1.0 None None None None Glycyrrhetinic acid is a pentacyclic triterpenoid derivative of the beta-amyrin type obtained from the hydrolysis of glycyrrhizic acid, which was obtained from the herb liquorice. It is used in flavouring and it masks the bitter taste of drugs like aloe and quinine. It is effective in the treatment of peptic ulcer and also has expectorant (antitussive) properties (Chandler,1985). In glycyrrhetinic acid the functional group (R) is a hydroxyl group. Research in 2005 demonstrated that with a proper functional group a very effective glycyrrhetinic artificial sweetener can be obtained. When R is an anionic NHCO(CH2)CO2K side chain, the sweetening effect is found to 1200 times that of sugar (human sensory panel data). A shorter or longer spacer reduces the sweetening effect. One explanation is that the taste bud cell receptor has 1.3 nanometers (13 angstroms) available for docking with the sweetener molecule. In addition the sweetener molecule requires three proton donor positions of which two reside at the extremities to be able to interact efficiently with the receptor cavity (Wikipedia). C30H46O4 None None None 18683.2 7553.29 8218.38 7336.67 7466.25 13272.0 9097.76 13886.2 6781.19 10094.0 10625.4 6571.07 6273.75 13781.4 8812.75 11822.4 9701.18 7834.82 6318.28 10835.4 9302.38 4411.13 10254.4 10800.9 11129.9 10204.0 8130.67 10196.0 6899.09 20805.1 9227.91 6529.46 5530.53 8213.03 6478.05 7118.25 6506.46 5561.47 4177.62 8074.89 9081.32 8466.34 494.3231446_MZ LysoPhosphatidylcholine (16:0) Un 1.0 None None None None LysoPC(16:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(16:0), in particular, consists of one chain of palmitic acid at the C-1 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. In blood plasma significant amounts of lysophosphatidylcholine are formed by a specific enzyme system, lecithin:cholesterol acyltransferase (LCAT), which is secreted from the liver. The enzyme catalyzes the transfer of the fatty acids of position sn-2 of phosphatidylcholine to the free cholesterol in plasma, with formation of cholesterol esters and lysophosphatidylcholine. Lysophospholipids have a role in lipid signaling by acting on lysophospholipid receptors (LPL-R). LPL-R's are members of the G protein-coupled receptor family of integral membrane proteins. C24H50NO7P None None None 7680.18 9138.7 8184.23 8517.41 8810.91 9141.85 8985.48 9165.47 9578.87 7930.02 10622.9 12019.5 6512.66 8336.52 8171.76 7625.16 10161.0 9510.0 5998.1 9968.03 7983.03 8169.39 9810.25 6563.01 9377.37 9088.37 8417.08 10996.8 8486.86 9673.17 8622.47 6992.87 10864.8 7162.49 7116.1 8089.56 7082.45 10614.5 5314.18 8679.74 7056.01 7639.95 495.2662560_MZ APGPR Enterostatin Un 1.0 None None None None Enterostatin APGPR (Ala-Pro-Gly-Pro-Arg) is a pentapeptide released from procolipase during fat digestion. In addition to the pancreas, enterostatin-immunoreactive cells are also present in the antrum and proximal small intestine. Enterostatin selectively reduces fat intake, decreases insulin secretion, and also increases energy expenditure by activating brown adipose tissue during high-fat feeding. Enterostatins are pentapeptides derived from the NH2-terminus of procolipase after tryptic cleavage and belong to the family of gut-brain peptides. Enterostatin is generated by the action of trypsin on procolipase in the intestinal lumen. Its structure is highly conserved in evolution, with an amino acid sequence of XPXPR. Three enterostatin sequences, Val-Pro-Asp-Pro-Arg (VPDPR), Val-Pro-Gly-Pro-Arg (VPGPR), and Ala-Pro-Gly-Pro-Arg (APGPR), have been studied extensively and shown to be almost equally effective in their ability to decrease dietary fat preference. Enterostatins are selective inhibitors of appetite, particularly of fat intake. Hyperenterostatinemia in obesity is probably secondary to enterostatin resistance; therefore, the regulatory system is producing more enterostatin to counteract the resistance. This is very similar to hyperinsulinemia and hyperleptinemia in obesity. The diminution in the meal-induced secretion of enterostatin in obesity suggests a delay in the appearance of satiety, leading to increased caloric intake. In rats enterostatin decreases body weight by decreasing fat-calorie intake and increasing the sympathetic firing rate of the nerves in interscapular brown adipose tissue. Enterostatin levels are elevated in the plasma of obese women, and enterostatin secretion is diminished after satiety. Oral administration of enterostatin, however, has no effect on food intake, energy expenditure, or body weight in subjects with a preference for a high-fat diet experiencing a negative energy and fat balance, and the physiology of enterostatin in humans remains to be defined. (PMID: 10084574, 9526102, 8886249). C21H36N8O6 None None None 7649.32 7702.34 8848.31 9331.98 11148.3 8773.66 8599.62 7973.58 9968.24 6521.56 8241.92 9676.68 6546.51 9590.36 9823.34 8429.63 11655.3 5219.98 6145.66 9795.63 10128.8 8564.55 7700.99 7785.26 9449.9 8020.76 9053.39 7545.12 7455.45 9175.79 8283.8 6557.17 7037.35 5093.8 9050.26 6718.32 6666.16 8918.8 4992.33 8462.11 7303.43 8829.33 498.2885195_MZ Taurochenodesoxycholic acid Un 1.0 None None None None Taurochenodesoxycholic acid is a bile acid formed in the liver by conjugation of chenodeoxycholate with taurine, usually as the sodium salt. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487, 16037564, 12576301, 11907135). C26H45NO6S, Taurodeoxycholic acid, Tauroursodeoxycholic acid None None None 708443.0 319214.0 603888.0 590823.0 446204.0 367732.0 612180.0 450504.0 458448.0 396703.0 332863.0 962384.0 316549.0 505172.0 660135.0 762169.0 684949.0 429137.0 494306.0 605214.0 609611.0 376490.0 494727.0 505583.0 739805.0 454727.0 1292170.0 507254.0 552802.0 556620.0 553676.0 409735.0 418298.0 307309.0 588692.0 382119.0 395934.0 619812.0 343670.0 556052.0 617318.0 1296840.0 500.9876916_MZ Thymidine 5'-triphosphate Un 1.0 None None None None C10H17N2O14P3 None None None 6106.5 5959.52 5790.19 5844.73 5522.54 6158.67 5590.14 5521.1 6089.95 5474.22 6201.82 6354.41 5769.67 6390.22 5564.21 6121.2 5558.48 5919.45 5451.98 5839.18 6021.88 6083.66 5455.57 5688.52 5419.56 5664.8 5584.57 6071.15 5926.83 6412.52 5395.14 5914.85 5723.21 5427.28 6447.7 5820.46 5388.77 5846.36 4405.81 5931.42 5823.8 5356.48 503.1614319_MZ Maltotriose Un 1.0 None None None None Maltotriose is a common oligosaccharide metabolite found in human urine after maltose ingestion or infusion (PMID 6645121). Maltotriose is increased in Glycogen storage disease II (OMIM 232300) due to a mutation of the enzyme alpha-1,4-glucosidase (E.C. 3.2.1.20) (4286143). C18H32O16, Raffinose, Levan, 3-Galactosyllactose, Dextrin, 1-Kestose, Melezitose None None None 32340.9 42517.5 53105.9 16784.0 23212.9 41002.8 29884.3 20245.9 43115.3 56712.8 42083.0 42501.9 40672.4 39482.4 46149.7 50113.7 18415.8 33488.5 83819.8 37083.3 46745.3 62179.4 39326.4 39402.5 26659.2 37210.0 70783.4 51051.0 85976.7 64040.9 47751.2 30478.7 30930.2 34516.3 59726.1 71271.9 41250.0 53493.5 24021.0 57278.8 44300.4 41743.8 504.3081299_MZ Lysophosphatidylethanolamine with formula C25H48NO7P Un 1.0 None None None None LysoPE(0:0/20:2(11Z,14Z)) is a lysophosphatidylethanolamine or a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylethanolamines (LPEs) can function as plant growth regulators with several diverse uses. (LPEs) are approved for outdoor agricultural use to accelerate ripening and improve the quality of fresh produce. They are also approved for indoor use to preserve stored crops and commercial cut flowers. As a breakdown product of phosphatidylethanolamine (PE), LPE is present in cells of all organisms. C25H48NO7P None None None 20541.3 17228.4 15125.7 17555.7 12371.3 17042.4 16637.5 18124.6 20668.5 14565.9 20458.2 23796.9 14221.5 19658.1 10541.1 16327.0 21784.1 20661.5 14117.8 18135.0 17492.8 14277.4 18872.8 15467.6 18425.2 17781.1 16990.9 19569.3 15272.0 18438.4 19007.1 11088.1 17322.5 15364.3 13922.7 19232.9 15193.3 14657.9 8005.76 13772.0 14293.0 13050.8 505.9878006_MZ Adenosine triphosphate Un 1.0 None None None None Adenosine triphosphate (ATP) is a nucleotide consisting of a purine base (adenine) attached to the first carbon atom of ribose (a pentose sugar). Three phosphate groups are esterified at the fifth carbon atom of the ribose. ATP is incorporated into nucleic acids by polymerases in the processes of DNA replication and transcription. ATP contributes to cellular energy charge and participates in overall energy balance, maintaining cellular homeostasis. ATP can act as an extracellular signaling molecule via interactions with specific purinergic receptors to mediate a wide variety of processes as diverse as neurotransmission, inflammation, apoptosis, and bone remodelling. Extracellular ATP and its metabolite adenosine have also been shown to exert a variety of effects on nearly every cell type in human skin, and ATP seems to play a direct role in triggering skin inflammatory, regenerative, and fibrotic responses to mechanical injury, an indirect role in melanocyte proliferation and apoptosis, and a complex role in Langerhans cell-directed adaptive immunity. During exercise, intracellular homeostasis depends on the matching of adenosine triphosphate (ATP) supply and ATP demand. Metabolites play a useful role in communicating the extent of ATP demand to the metabolic supply pathways. Effects as different as proliferation or differentiation, chemotaxis, release of cytokines or lysosomal constituents, and generation of reactive oxygen or nitrogen species are elicited upon stimulation of blood cells with extracellular ATP. The increased concentration of adenosine triphosphate (ATP) in erythrocytes from patients with chronic renal failure (CRF) has been observed in many studies but the mechanism leading to these abnormalities still is controversial. (PMID: 15490415, 15129319, 14707763, 14696970, 11157473). C10H16N5O13P3, dGTP None None None 454839.0 547566.0 590429.0 258884.0 903816.0 494092.0 950275.0 1064990.0 630630.0 329804.0 655328.0 671755.0 477530.0 644906.0 780657.0 655520.0 1037390.0 271814.0 562205.0 781581.0 586559.0 375389.0 592803.0 448900.0 790586.0 528963.0 934394.0 302478.0 225277.0 482281.0 1345090.0 480645.0 734961.0 601166.0 237143.0 277206.0 496449.0 638889.0 249950.0 368979.0 653046.0 442483.0 506.9588020_MZ Inosine triphosphate Un 1.0 None None None None Inosine triphosphate (ITP) is an intermediate in the purine metabolism pathway. Relatively high levels of ITP in red cells are found in individuals as result of deficiency of inosine triphosphatase (EC 3.1.3.56, ITPase) ITPase is a cytosolic nucleoside triphosphate pyrophosphohydrolase specific for ITP catalysis to inosine monophosphate (IMP) and deoxy-inosine triphosphate (dITP) to deoxy-inosine monophosphate. ITPase deficiency is not associated with any defined pathology other than the characteristic and abnormal accumulation of ITP in red blood cells. Nevertheless, ITPase deficiency may have pharmacogenomic implications, and the abnormal metabolism of 6-mercaptopurine in ITPase-deficient patients may lead to thiopurine drug toxicity. ITPase's function is not clearly understood but possible roles for ITPase could be to prevent the accumulation of rogue nucleotides which would be otherwise incorporated into DNA and RNA, or compete with nucleotides such as GTP in signalling processes. (PMID : 170291, 1204209, 17113761, 17924837). C10H15N4O14P3 None None None 11846.1 12202.9 11971.7 13222.6 13000.7 13172.1 14790.0 14384.4 11978.9 10809.4 12327.6 11373.4 13372.3 12124.5 14347.0 18756.4 14376.2 10425.0 11483.4 13293.0 12476.6 10584.2 12656.9 10588.9 12918.8 11210.5 14583.3 10101.1 9778.21 11772.6 18694.5 17335.6 10118.3 10401.8 11058.2 10884.3 10384.6 12496.3 7164.28 10535.8 13645.8 11054.0 508.3394647_MZ Lysophosphatidylethanolamine with formula C25H52NO7P Un 1.0 None None None None C25H52NO7P None None None 69233.0 64482.4 79379.1 52620.8 72967.8 71765.2 71561.2 61671.8 67313.4 58169.1 85567.7 80808.9 89752.6 65579.7 55017.0 58109.3 68160.0 128275.0 61789.9 84594.8 59838.6 67304.1 74623.3 52338.1 73051.4 74935.7 55307.8 97161.4 77982.4 55077.6 72522.2 59640.2 88335.1 60147.2 52910.7 62212.5 59618.8 94593.9 53514.1 70344.9 93263.4 52733.8 509.4187751_MZ Diglyceride with formula C31H58O5 Un 1.0 None None None None DG(14:0/14:1(9Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(14:0/14:1(9Z)/0:0), in particular, consists of one chain of myristic acid at the C-1 position and one chain of myristoleic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the myristoleic acid moiety is derived from milk fats. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C31H58O5 None None None 1406.35 1243.44 2036.75 1232.43 1315.49 1371.39 2106.2 3903.45 852.324 996.575 1275.04 932.32 1494.7 1196.13 1819.58 1638.71 5209.77 1828.11 957.038 2742.09 1023.89 639.998 897.744 1161.07 1355.2 848.325 1473.9 2081.76 650.64 1405.11 1953.25 1360.11 725.759 1462.06 945.708 1030.37 655.731 708.986 1384.66 1200.57 1695.34 1019.01 511.4342933_MZ Diglyceride with formula C31H60O5 Un 1.0 None None None None DG(14:0/14:0/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(14:0/14:0/0:0), in particular, consists of two chains of myristic acid at the C-1 and C-2 positions. The myristic acid moieties are derived from nutmeg and butter. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol. Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C31H60O5 None None None 1041.58 1159.4 1427.07 1044.32 1023.29 781.188 1193.27 2132.71 787.2 831.114 1073.46 1273.6 491.362 1202.45 1104.48 1183.59 2851.46 1096.86 895.496 1390.74 911.753 692.038 1053.5 830.324 1140.05 716.361 1235.43 1175.72 675.086 1014.07 1507.2 1358.17 720.54 871.289 879.281 999.642 750.488 967.408 931.71 868.266 754.2 857.382 512.2676542_MZ Sulfolithocholylglycine Un 1.0 None None None None Sulfolithocholylglycine is an acyl glycine and a bile acid-glycine conjugate. It is a secondary bile acid produced by the action of enzymes existing in the microbial flora of the colonic environment. In hepatocytes, both primary and secondary bile acids undergo amino acid conjugation at the C-24 carboxylic acid on the side chain, and almost all bile acids in the bile duct therefore exist in a glycine conjugated form (PMID:16949895). Sulfolithocholylglycine is a sulfated bile acids which has a greater renal clearance rate than lithocholylglycine. C26H43NO7S None None None 419163.0 182900.0 443991.0 362101.0 211365.0 476389.0 482172.0 766036.0 227791.0 227908.0 344466.0 383262.0 162772.0 687049.0 381865.0 350563.0 516250.0 150987.0 545137.0 241674.0 536495.0 166860.0 308913.0 569004.0 973295.0 224624.0 1471260.0 370695.0 345329.0 496563.0 388724.0 243795.0 131208.0 204650.0 578865.0 174846.0 194855.0 515934.0 119404.0 420159.0 295984.0 1059330.0 514.2842602_MZ Taurocholic acid Un 1.0 None None None None Taurocholic acid is a bile acid and is the product of conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487 , 16037564 , 12576301 , 11907135 ) Taurocholic acid, as with all bile acids, acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and cholerectic (a bile purging agent). Hydrolysis of taurocholic acid yields taurine, a nonessential amino acid. Taurocholic acid is one of the main components of urinary nonsulfated bile acids in biliary atresia. Raised levels of the bile acid taurocholate in the fetal serum in obstetric cholestasis may result in the development of a fetal dysrhythmia and in sudden intra-uterine death. (PMID: 3944741 , 11256973 ). C26H45NO7S, Tauroursocholic acid, Taurallocholic acid, Tauro-b-muricholic acid, Taurohyocholate None None None 8419320.0 6035040.0 10462800.0 9695510.0 6850770.0 8143230.0 8965420.0 6801920.0 6625070.0 8442440.0 5719580.0 8847390.0 6411660.0 11855500.0 8409200.0 8605850.0 15537200.0 6855160.0 10562300.0 7575270.0 10068200.0 7306650.0 7728130.0 7598680.0 13429400.0 5677540.0 12255600.0 7576640.0 9701460.0 10073200.0 9288560.0 6098330.0 6696510.0 5841000.0 12203300.0 7630030.0 7991520.0 8448540.0 5767650.0 8973250.0 9133880.0 13509800.0 521.8847268_MZ Molybdopterin Un 1.0 None None None None Molybdenum cofactor is a cofactor required for the activity of enzymes such as sulfite oxidase, xanthine oxidoreductase, and aldehyde oxidase. It is a coordination complex formed between molybdopterin (which, despite the name, does not contain molybdenum) and an oxide of molybdenum. Molybdopterins, in turn, are synthesized from guanosine triphosphate. Molybdenum cofactor functions directly in ethylbenzene dehydrogenase, glyceraldehyde-3-phosphate ferredoxin oxidoreductase, and respiratory arsenate reductase. In animals and plants these enzymes use molybdenum bound at the active site in a tricyclic molybdenum cofactor. All molybdenum-using enzymes so far identified in nature use this cofactor The simplest structure of molybdopterin contains a pyranopterin coordinated to molybdenum. The pyranopterin structure is a fused ring system containing a pyran fused to pterin. In addition, the pyran ring is substituted with two thiols and an alkyl phosphate. In molybdopterin, the thiols coordinate to molybdenum. In some cases, the alkyl phosphate group is replaced by an alkyl diphosphate nucleotide. -- Wikipedia. C10H12MoN5O8PS2 None None None 2694.26 2759.69 2333.56 2941.98 2460.28 2794.47 2274.28 2730.36 2605.19 2495.34 2690.99 2520.07 2311.77 2543.83 2736.85 4620.78 2266.68 2440.36 2123.94 2610.55 2724.64 2398.17 2576.49 2594.69 2416.97 2452.67 2677.68 2660.99 2718.72 2611.36 3171.16 4367.85 2078.93 2080.49 3211.17 2788.97 2128.26 2524.72 1722.0 2774.07 2293.61 2423.51 521.9818654_MZ Guanosine triphosphate Un 1.0 None None None None Guanosine triphosphate (GTP) is a guanine nucleotide containing three phosphate groups esterified to the sugar moiety. GTP functions as a carrier of phosphates and pyrophosphates involved in channeling chemical energy into specific biosynthetic pathways. GTP activates the signal transducing G proteins which are involved in various cellular processes including proliferation, differentiation, and activation of several intracellular kinase cascades. Proliferation and apoptosis are regulated in part by the hydrolysis of GTP by small GTPases Ras and Rho. Another type of small GTPase, Rab, plays a role in the docking and fusion of vesicles and may also be involved in vesicle formation. In addition to its role in signal transduction, GTP also serves as an energy-rich precursor of mononucleotide units in the enzymatic biosynthesis of DNA and RNA. C10H16N5O14P3, 8-Oxo-dGTP None None None 25590.5 30201.9 35071.0 18000.9 49122.7 27490.2 59660.1 57544.6 31896.2 21585.1 32301.4 35921.9 34047.0 33700.8 43769.4 35051.0 61052.7 21695.0 33521.4 48102.3 28959.4 20336.5 31655.0 23659.7 44134.7 27693.5 55636.4 20266.5 15985.7 25665.0 75261.9 29489.0 41673.2 31297.4 16953.2 18280.3 24486.5 35934.1 20776.2 23755.3 44293.8 26452.9 522.3243148_MZ Lysophosphatidylethanolamine with formula C25H46NO7P Un 1.0 None None None None LysoPE(0:0/20:3(11Z,14Z,17Z)) or LPE(0:0/20:3(11Z,14Z,17Z)) is a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylethanolamines (LPEs) can function as plant growth regulators with several diverse uses. (LPEs) are approved for outdoor agricultural use to accelerate ripening and improve the quality of fresh produce. They are also approved for indoor use to preserve stored crops and commercial cut flowers. As a breakdown product of phosphatidylethanolamine (PE), LPE is present in cells of all organisms. C25H46NO7P None None None 3835.2 5837.65 3955.46 9256.3 6447.73 6027.64 5063.86 4396.0 5857.54 4404.28 4856.96 4872.34 4034.16 3952.43 5070.72 3862.31 4459.25 4639.64 3513.52 8054.26 3574.2 6745.63 4355.19 3253.89 6219.16 4516.63 4595.22 7295.51 3750.37 4685.63 5172.46 4532.73 4689.9 2751.99 6036.47 9623.88 4327.45 5229.36 4549.14 4630.68 3784.46 4339.71 523.4357061_MZ Diglyceride with formula C32H60O5 Un 1.0 None None None None DG(14:1(9Z)/15:0/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(14:1(9Z)/15:0/0:0), in particular, consists of one chain of myristoleic acid at the C-1 position and one chain of pentadecanoic acid at the C-2 position. The myristoleic acid moiety is derived from milk fats, while the pentadecanoic acid moiety is derived from dairy products and milk fat. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C32H60O5 None None None 1107.32 1099.27 1230.36 1114.57 816.859 1102.74 941.192 2007.14 810.864 755.104 1070.3 1006.02 427.902 1150.96 1200.52 1596.82 2547.52 1021.71 655.402 1405.61 871.855 644.965 798.46 931.045 1009.66 734.181 935.328 1130.72 640.818 1077.81 1462.76 1331.55 582.925 960.065 759.807 802.165 596.945 831.686 1048.17 861.757 622.082 745.069 525.9730762_MZ Phosphoadenosine phosphosulfate Un 1.0 None None None None 3'-Phosphoadenosine-5'-phosphosulfate. Key intermediate in the formation by living cells of sulfate esters of phenols, alcohols, steroids, sulfated polysaccharides, and simple esters, such as choline sulfate. It is formed from sulfate ion and ATP in a two-step process. This compound also is an important step in the process of sulfur fixation in plants and microorganisms. C10H15N5O13P2S None None None 9244.24 9827.18 10094.9 12393.3 10908.0 11241.9 11958.0 9472.7 10038.3 10900.7 9480.68 9771.94 12953.7 9307.81 13282.4 14300.9 10597.8 10906.3 11148.2 9865.06 9481.24 9467.84 10453.1 9083.58 10662.8 9924.59 11716.5 10185.9 10189.1 10715.6 10641.7 12577.2 8525.09 9162.32 12502.0 10759.1 9628.15 10710.4 9041.23 10984.6 12966.0 10682.6 526.2936608_MZ Lysophosphatidylethanolamine with formula C27H46NO7P Un 1.0 None None None None LysoPE(0:0/22:5(7Z,10Z,13Z,16Z,19Z)) is a lysophosphatidylethanolamine or a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylethanolamines (LPEs) can function as plant growth regulators with several diverse uses. (LPEs) are approved for outdoor agricultural use to accelerate ripening and improve the quality of fresh produce. They are also approved for indoor use to preserve stored crops and commercial cut flowers. As a breakdown product of phosphatidylethanolamine (PE), LPE is present in cells of all organisms. C27H46NO7P None None None 5171.85 5430.87 5144.86 6671.98 5146.27 6687.17 6973.62 6373.06 6610.49 5295.9 5852.68 7434.75 4353.83 7443.14 5154.43 5107.06 6826.68 4566.62 4767.02 7357.17 5154.89 4489.28 6138.73 4589.03 6333.14 5510.93 4719.74 5551.31 4389.0 6321.25 6736.13 4872.02 5064.09 4603.75 4272.41 5363.95 4936.43 5868.95 3077.27 5279.04 4952.18 5086.76 528.2631122_MZ Glycochenodeoxycholate-3-sulfate Un 1.0 None None None None Glycochenodeoxycholate-3-sulfate is a bile salt formed in the liver from chenodeoxycholate and glycine, usually as the sodium salt. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is a cholagogue and choleretic. C26H43NO8S, N-[(3a_5b_7a)-3-hydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-Glycine None None None 14359.4 9404.87 11172.8 11499.2 10850.9 14608.9 13172.1 18314.1 10747.9 11179.4 10892.0 11193.0 9667.6 22468.1 12012.3 11153.7 13709.2 9661.36 10462.2 11442.3 12699.6 8948.54 12596.0 10801.2 17814.6 9029.3 14039.2 10687.9 14148.9 16446.5 11086.3 8671.95 9029.66 8490.89 11594.1 10317.6 8798.86 11736.2 8895.96 12237.7 9589.58 15327.4 532.3451629_MZ Lysophosphatidylethanolamine with formula C27H52NO7P Un 1.0 None None None None C27H52NO7P None None None 3815.26 3106.57 2408.62 2775.7 2759.21 2827.97 3919.05 3773.03 2212.31 2108.58 2941.83 2057.59 5010.61 2884.67 2015.39 4005.03 3785.68 5697.44 2504.41 4095.88 3245.84 1417.04 2926.4 2719.36 3157.14 2048.22 2843.5 3555.2 1778.25 2755.25 4113.87 3383.87 1983.6 2418.19 1570.64 2831.57 1809.97 1810.34 2068.75 2608.23 4681.38 3179.65 536.3665487_MZ Lysophosphatidylethanolamine with formula C27H56NO7P Un 1.0 None None None None C27H56NO7P None None None 1931.92 2270.16 2045.1 1825.99 1657.15 2242.11 1410.47 1580.4 1651.7 1479.59 2284.99 2294.19 1633.17 2316.5 1416.51 2114.54 1927.66 2541.06 1488.12 2076.07 1821.37 1520.18 2040.81 1797.63 2248.5 1495.05 1903.71 2480.99 2105.34 2365.37 2038.7 1729.3 1881.06 1666.29 1359.23 1586.09 1698.8 2078.83 1026.67 1570.87 1797.75 1307.37 536.5034145_MZ N-Palmitoylsphingosine Un 1.0 None None None None N-Palmitoylsphingosine is a substrate for N-acylethanolamine-hydrolyzing acid amidase. C34H67NO3, Ceramide (d18:1/16:0) None None None 73306.5 25898.6 35505.5 46890.5 68550.5 20288.2 77950.9 68259.7 51490.8 33820.5 49687.7 46439.0 73637.7 48997.0 41577.7 27416.0 62863.7 113223.0 27218.2 59337.1 42031.8 29024.9 35346.2 37669.9 45398.7 63960.0 31655.0 60735.1 26818.4 29978.9 32177.7 17654.2 83850.9 23778.8 14340.6 37472.6 47621.2 48175.5 46814.7 36706.8 58336.5 59573.8 537.4508361_MZ Diglyceride with formula C33H62O5 Un 1.0 None None None None DG(14:0/16:1(9Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(14:0/16:1(9Z)/0:0), in particular, consists of one chain of myristic acid at the C-1 position and one chain of palmitoleic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the palmitoleic acid moiety is derived from animal fats and vegetable oils. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C33H62O5 None None None 773.469 588.309 857.65 494.495 516.04 493.155 485.313 1673.7 277.421 274.802 458.141 319.728 266.529 510.647 709.873 966.041 2274.13 640.792 383.215 955.895 354.794 291.873 479.961 545.958 480.51 326.726 564.235 614.454 332.913 502.324 870.984 676.757 190.421 429.331 400.153 378.079 290.862 234.778 442.92 531.234 288.424 401.918 537.8608254_MZ Molybdenum cofactor (sulfide) Un 1.0 None None None None Molybdenum cofactor reacts wtih L-cysteine to produce molybdenum cofactor (sulfide), L-alanine, and H2O. Molybdenum cofactor sulphurase catalyzes the reaction. C10H12MoN5O7PS3 None None None 2962.06 2699.56 2835.38 2949.92 1757.95 2205.26 3908.25 2881.28 1969.79 2077.26 2222.75 1575.43 3270.58 2266.01 2260.46 4145.34 5292.59 2962.62 2178.96 2960.28 2246.45 1613.63 2448.23 2368.68 2322.35 1570.36 2215.2 3234.32 1878.63 2338.89 2843.4 4782.34 1381.31 3099.84 2333.52 2707.18 1775.77 1670.72 1449.06 2459.91 3226.43 2508.38 538.3290939_MZ LysoPhosphatidylcholine (18:2(9Z,12Z)) Un 1.0 None None None None LysoPC(18:2(9Z,12Z)) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(18:2(9Z,12Z)), in particular, consists of one chain of linoleic acid at the C-1 position. The linoleic acid moiety is derived from seed oils. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. In blood plasma significant amounts of lysophosphatidylcholine are formed by a specific enzyme system, lecithin:cholesterol acyltransferase (LCAT), which is secreted from the liver. The enzyme catalyzes the transfer of the fatty acids of position sn-2 of phosphatidylcholine to the free cholesterol in plasma, with formation of cholesterol esters and lysophosphatidylcholine. Lysophospholipids have a role in lipid signaling by acting on lysophospholipid receptors (LPL-R). LPL-R's are members of the G protein-coupled receptor family of integral membrane proteins. C26H50NO7P None None None 13396.9 11445.2 10467.8 11946.0 8413.01 11444.9 11601.4 11666.0 13304.8 9386.44 13595.1 14537.6 9927.56 12831.2 7107.09 10654.4 13865.2 13092.0 9404.79 12825.9 11076.4 9522.33 12115.7 10305.0 12185.3 11770.5 11187.9 13471.6 10142.1 12508.3 12459.4 6688.28 11628.5 9764.42 10883.4 12661.0 9836.63 9674.31 6594.92 8774.59 8870.22 8874.39 539.4551266_MZ (9-cis,9'-cis)-7,7',8,8'-Tetrahydro-y,y-Carotene Un 1.0 None None None None (9-cis,9'-cis)-7,7',8,8'-tetrahydro-Carotene is a carotenoid found in human fluids. Carotenoids are isoprenoid molecules that are widespread in nature and are typically seen as pigments in fruits, flowers, birds and crustacea. Animals are unable to synthesise carotenoids de novo, and rely upon the diet as a source of these compounds. Over recent years there has been considerable interest in dietary carotenoids with respect to their potential in alleviating age-related diseases in humans. This attention has been mirrored by significant advances in cloning most of the carotenoid genes and in the genetic manipulation of crop plants with the intention of increasing levels in the diet. Studies have shown an inverse relationship between the consumption of certain fruits and vegetables and the risk of epithelial cancer. Since carotenoids are among the micronutrients found in cancer preventive foods, detailed qualitative and quantitative determination of these compounds, particularly in fruits and vegetables and in human plasma, have recently become increasingly important. (PMID: 1416048, 15003396). C40H60 None None None 807.706 821.043 633.74 816.86 777.306 818.418 928.511 1231.15 546.573 577.805 713.632 547.421 655.556 637.354 808.383 1470.13 1591.71 887.234 586.446 914.024 618.641 484.106 682.232 767.88 771.666 540.714 730.951 766.775 480.035 773.258 1394.84 1114.55 420.435 757.548 617.545 551.601 442.941 520.076 620.76 566.036 620.215 684.611 540.3449140_MZ Lysophospholipid with formula C26H54NO7P Un 1.0 None None None None LysoPC(18:1(11Z)) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(18:1(11Z)), in particular, consists of one chain of vaccenic acid at the C-1 position. The vaccenic acid moiety is derived from butter fat and animal fat. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. In blood plasma significant amounts of lysophosphatidylcholine are formed by a specific enzyme system, lecithin:cholesterol acyltransferase (LCAT), which is secreted from the liver. The enzyme catalyzes the transfer of the fatty acids of position sn-2 of phosphatidylcholine to the free cholesterol in plasma, with formation of cholesterol esters and lysophosphatidylcholine. Lysophospholipids have a role in lipid signaling by acting on lysophospholipid receptors (LPL-R). LPL-R's are members of the G protein-coupled receptor family of integral membrane proteins. C26H52NO7P None None None 10913.2 8327.91 9702.11 9654.12 15656.2 10169.3 10411.0 12513.2 13348.8 8400.85 12427.7 13627.6 15174.6 14048.7 9033.6 9191.04 10532.2 17341.5 9393.54 12696.8 9576.08 10992.9 11415.6 9505.68 11540.5 15266.5 11266.2 10578.2 10345.0 8645.59 9663.33 7680.09 14194.1 9783.95 8730.33 12115.1 9712.16 11635.4 6605.31 11167.1 13829.0 10508.2 541.2669930_MZ Cortolone-3-glucuronide Un 1.0 None None None None Cortolone-3-glucuronide is a natural human metabolite of cortolone generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys. C27H42O11 None None None 6272.17 3763.93 4405.44 4865.66 6505.86 4644.87 6084.75 5091.63 7122.4 5800.93 5327.13 4149.63 3077.74 4907.83 6840.27 8047.57 5705.06 3546.84 3793.06 5635.35 4813.28 3963.58 3994.32 4303.51 4833.13 4702.74 4979.68 3975.2 4530.04 5651.48 3919.59 3750.82 4349.01 3150.16 5141.28 6679.99 2888.51 3870.78 2565.39 5125.44 4476.33 6769.51 542.3606749_MZ Lysophospholipid with formula C28H54NO7P Un 1.0 None None None None LysoPC(0:0/18:0) or LPC(0:0/18:0) is a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. There is also a phospholipase A1, which is able to cleave the sn-1 ester bond. Lysophosphatidylcholine has pro-inflammatory properties in vitro and it is known to be a pathological component of oxidized lipoproteins (LDL) in plasma and of atherosclerotic lesions. Recently, it has been found to have some functions in cell signalling, and specific receptors (coupled to G proteins) have been identified. It activates the specific phospholipase C that releases diacylglycerols and inositol triphosphate with resultant increases in intracellular Ca2+ and activation of protein kinase C. It also activates the mitogen-activated protein kinase in certain cell types.LysoPC(0:0/18:0) has been shown to be protective against lethal sepsis in experimental animals by various mechanisms, including stimulation of neutrophils to eliminate invading pathogens through a peroxide-dependent reaction. C26H54NO7P None None None 37577.0 34381.8 43118.3 27734.9 38172.8 36483.9 37130.5 33472.4 36660.2 30523.3 46847.3 42553.5 52307.7 35691.3 29020.5 27048.1 37103.3 69587.9 33430.3 43712.1 32287.5 37722.5 39937.4 29074.7 38435.2 40713.9 29624.5 50633.8 41686.2 29192.3 35146.9 26495.1 49034.9 32199.5 27533.3 33226.2 33179.0 51558.4 31363.9 39546.1 42871.1 29339.6 544.2693225_MZ N-[(3a_5b_7a_12a)-3_12-dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-Glycine Un 1.0 None None None None N-[(3a,5b,7a,12a)-3,12-dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-Glycine is an acyl glycine and a sulfated bile acid-glycine conjugate. It is a secondary bile acid produced by the action of enzymes existing in the microbial flora of the colonic environment. In hepatocytes, both primary and secondary bile acids undergo amino acid conjugation at the C-24 carboxylic acid on the side chain, and almost all bile acids in the bile duct therefore exist in a glycine conjugated form (PMID:16949895). As a bile acid sulfate, N-[(3a,5b,7a,12a)-3,12-dihydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-Glycine is typically found in urine. These conjugates are formed as a part of detoxification of endogenous and exogenous components in the body (PMID:3584362). C26H43NO9S None None None 7841.13 7073.39 6087.46 9839.85 7612.79 7268.53 6288.3 6128.1 8628.31 8107.13 6990.68 8409.24 8302.45 8283.47 6423.33 6480.26 6337.06 10998.5 5876.62 7558.12 6837.19 5516.28 6763.77 7587.21 8399.21 6547.56 6012.25 6507.89 5885.11 8212.96 6322.48 7349.35 6688.51 6495.78 6406.05 7869.93 7927.44 5940.01 5558.75 7537.12 7258.1 7453.68 545.4548394_MZ Diglyceride with formula C32H62O5 Un 1.0 None None None None DG(14:0/15:0/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(14:0/15:0/0:0), in particular, consists of one chain of myristic acid at the C-1 position and one chain of pentadecanoic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the pentadecanoic acid moiety is derived from dairy products and milk fat. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C32H62O5 None None None 1449.08 1058.1 734.048 1668.55 1323.81 1101.88 1229.79 1258.45 1072.21 1185.6 1238.49 974.927 1010.19 1332.31 1201.25 1839.87 1370.73 1651.28 849.977 1029.42 879.263 757.409 1190.35 1189.4 1233.87 996.565 1059.41 1476.83 780.167 1004.71 1479.7 1797.23 872.696 1006.95 790.027 1040.96 847.676 936.617 1068.47 940.227 982.944 1208.02 546.0734726_MZ 3-carboxy-1-hydroxypropylthiamine diphosphate Un 1.0 None None None None 3-Carboxy-1-hydroxypropyl-ThPP is an intermediate in Citrate cycle (TCA cycle). 3-Carboxy-1-hydroxypropyl-ThPP is the second to last step in the synthesis of Succinyl-CoA and is converted from 2-Oxoglutarate via the enzyme 2-oxoglutarate dehydrogenase E1 component (EC.1.2.4.2). It is then converted to S-Succinyldihydrolipoamide-E via the enzyme 2-oxoglutarate dehydrogenase E1 component (EC.1.2.4.2). C16H25N4O10P2S None None None 24946.9 42338.4 45316.3 51119.2 72683.4 36189.4 48263.9 65515.0 51104.7 52182.7 50344.5 58645.1 21471.4 35927.3 87497.2 48166.9 70074.5 22315.2 47067.4 35593.4 35330.5 29405.6 36632.6 30071.2 53882.2 40586.6 76276.2 24367.8 20790.3 28698.0 68328.2 48668.6 57929.2 34651.8 29503.2 28461.0 39930.0 66531.4 23249.0 36917.9 50484.9 34040.7 546.3630356_MZ LysoPhosphatidylcholine (20:2(11Z,14Z)) Un 1.0 None None None None LysoPC(20:2(11Z,14Z)) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(20:2(11Z,14Z)), in particular, consists of one chain of eicosadienoic acid at the C-1 position. The eicosadienoic acid moiety is derived from fish oils and liver. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. In blood plasma significant amounts of lysophosphatidylcholine are formed by a specific enzyme system, lecithin:cholesterol acyltransferase (LCAT), which is secreted from the liver. The enzyme catalyzes the transfer of the fatty acids of position sn-2 of phosphatidylcholine to the free cholesterol in plasma, with formation of cholesterol esters and lysophosphatidylcholine. Lysophospholipids have a role in lipid signaling by acting on lysophospholipid receptors (LPL-R). LPL-R's are members of the G protein-coupled receptor family of integral membrane proteins. C28H54NO7P None None None 1596.85 1365.73 782.331 1184.74 556.097 1348.49 1382.55 872.943 553.744 497.363 769.132 421.951 1340.68 915.467 561.507 1363.2 968.938 1927.28 852.062 1618.37 1364.58 213.768 961.918 1273.86 1168.4 452.684 712.928 1111.49 430.092 1343.23 1522.44 1025.97 489.373 865.839 409.523 1050.84 510.541 323.653 1066.21 866.933 1754.95 1065.89 547.0311562_MZ UDP-4-dehydro-6-deoxy-D-glucose Un 1.0 None None None None UDP-4-dehydro-6-deoxy-D-glucose is synthesized from UDP-glucose through the enzyme UDP-glucose 4,6-dehydratase. C15H22N2O16P2 None None None 4107.2 4086.68 4925.02 4055.58 4297.45 4695.12 4215.69 3838.02 4484.43 4413.48 4148.32 5006.28 4604.68 4199.74 4721.87 4775.88 3492.32 4653.13 4674.86 4132.15 4741.67 4533.21 3990.55 4051.32 3846.5 4572.63 4473.49 4270.64 4975.49 4817.05 3884.73 3764.76 4231.24 3683.03 5571.59 4929.28 4270.54 4610.36 3148.88 4854.26 4565.55 4248.99 549.4104600_MZ 3-cis-Hydroxy-b,e-Caroten-3'-one Un 1.0 None None None None cis-3-hydroxy-b,e-Caroten-3'-one is a carotenoid found in human fluids. Carotenoids are isoprenoid molecules that are widespread in nature and are typically seen as pigments in fruits, flowers, birds and crustacea. Animals are unable to synthesise carotenoids de novo, and rely upon the diet as a source of these compounds. Over recent years there has been considerable interest in dietary carotenoids with respect to their potential in alleviating age-related diseases in humans. This attention has been mirrored by significant advances in cloning most of the carotenoid genes and in the genetic manipulation of crop plants with the intention of increasing levels in the diet. Studies have shown an inverse relationship between the consumption of certain fruits and vegetables and the risk of epithelial cancer. Since carotenoids are among the micronutrients found in cancer preventive foods, detailed qualitative and quantitative determination of these compounds, particularly in fruits and vegetables and in human plasma, have recently become increasingly important. (PMID: 1416048, 15003396). C40H54O None None None 1089.9 841.204 773.668 900.366 800.739 1195.81 915.881 1306.07 764.483 750.006 1081.76 938.883 572.198 1163.03 1321.84 1196.09 1484.74 702.632 479.913 1294.85 684.0 554.342 759.7 848.698 882.082 632.773 863.831 909.066 521.328 1264.83 1308.79 1144.81 729.736 980.828 754.845 641.416 530.985 678.771 665.786 831.273 707.863 757.967 551.3058019_MZ 5b-Cyprinol sulfate Un 1.0 None None None None 5b-Cyprinol sulfate is an intermediate in bile acid biosynthesis. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487, 16037564, 12576301, 11907135). C27H48O8S, Triterpenoid None None None 3106.69 2926.49 2886.19 3412.02 3699.67 4261.26 3019.8 2441.89 2817.69 3224.03 3764.06 3256.68 2599.66 3712.59 3410.19 2967.9 4543.19 2238.56 2434.21 2566.81 3058.63 2353.98 3317.09 3081.29 3355.82 2509.34 3775.04 2548.24 2412.63 3714.75 3110.27 2977.19 2345.86 2082.87 3045.1 2810.5 2133.34 2643.19 1386.89 3181.16 2475.7 2613.32 551.4667408_MZ Diglyceride with formula C34H64O5 Un 1.0 None None None None DG(15:0/16:1(9Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(15:0/16:1(9Z)/0:0), in particular, consists of one chain of pentadecanoic acid at the C-1 position and one chain of palmitoleic acid at the C-2 position. The pentadecanoic acid moiety is derived from dairy products and milk fat, while the palmitoleic acid moiety is derived from animal fats and vegetable oils. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C34H64O5 None None None 1256.27 1012.29 1288.58 1018.21 1333.19 1017.85 1267.64 2463.33 869.098 1027.32 1029.98 614.701 1057.81 1008.43 1438.11 1526.4 3360.92 952.093 652.655 1565.45 770.77 586.383 939.534 914.461 1122.23 811.573 1131.43 882.575 578.14 884.748 1427.7 1275.89 543.073 803.667 579.588 745.061 675.449 525.979 931.003 855.129 645.314 890.217 553.4456018_MZ Triglyceride with formula C33H62O6 Un 1.0 None None None None TG(10:0/10:0/10:0) or tricapric glyceride is a tridecanoic acid triglyceride or medium chain triglyceride. Triglycerides (TGs) are also known as triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.e. fatty acid tri-esters of glycerol). TGs may be divided into three general types with respect to their acyl substituents. They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. TG(10:0/10:0/10:0), in particular, consists of one chain of decanoic acid at the C-1 position, one chain of decanoic acid at the C-2 position and one chain of decanoic acid acid at the C-3 position. TGs are the main constituent of vegetable oil and animal fats. TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) with the help of lipases and bile secretions, which can then move into blood vessels. The triglycerides are rebuilt in the blood from their fragments and become constituents of lipoproteins, which deliver the fatty acids to and from fat cells among other functions. Various tissues can release the free fatty acids and take them up as a source of energy. Fat cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain cannot utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when it is broken down. (www.cyberlipid.org, www.wikipedia.org). TAGs can serve as fatty acid stores in all cells, but primarily in adipocytes of adipose tissue. The major building block for the synthesis of triacylglycerides, in non-adipose tissue, is glycerol. Adipocytes lack glycerol kinase and so must use another route to TAG synthesis. Specifically, dihydroxyacetone phosphate (DHAP), which is produced during glycolysis, is the precursor for TAG synthesis in adipose tissue. DHAP can also serve as a TAG precursor in non-adipose tissues, but does so to a much lesser extent than glycerol. The use of DHAP for the TAG backbone depends on whether the synthesis of the TAGs occurs in the mitochondria and ER or the ER and the peroxisomes. The ER/mitochondria pathway requires the action of glycerol-3-phosphate dehydrogenase to convert DHAP to glycerol-3-phosphate. Glycerol-3-phosphate acyltransferase then esterifies a fatty acid to glycerol-3-phosphate thereby generating lysophosphatidic acid. The ER/peroxisome reaction pathway uses the peroxisomal enzyme DHAP acyltransferase to acylate DHAP to acyl-DHAP which is then reduced by acyl-DHAP reductase. The fatty acids that are incorporated into TAGs are activated to acyl-CoAs through the action of acyl-CoA synthetases. Two molecules of acyl-CoA are esterified to glycerol-3-phosphate to yield 1,2-diacylglycerol phosphate (also known as phosphatidic acid). The phosphate is then removed by phosphatidic acid phosphatase (PAP1), to generate 1,2-diacylglycerol. This diacylglycerol serves as the substrate for addition of the third fatty acid to make TAG. Intestinal monoacylglycerols, derived from dietary fats, can also serve as substrates for the synthesis of 1,2-diacylglycerols. C33H62O6 None None None 1361.74 1264.97 1406.72 1421.36 1285.1 1335.33 1887.06 2258.63 847.358 1213.99 1309.25 779.95 1501.7 1391.17 1276.6 1607.73 2988.58 1968.23 966.894 1964.93 996.434 579.093 1131.76 1171.29 1124.99 708.203 1160.1 1538.51 444.306 1291.13 1802.06 1486.76 500.062 1205.96 870.147 1131.37 766.076 607.362 1189.65 1156.85 1483.45 1054.16 553.4808746_MZ Diglyceride with formula C34H66O5 Un 1.0 None None None None DG(15:0/16:0/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(15:0/16:0/0:0), in particular, consists of one chain of pentadecanoic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The pentadecanoic acid moiety is derived from dairy products and milk fat, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C34H66O5 None None None 957.945 954.704 1031.76 923.589 975.682 842.01 1223.38 1339.93 771.729 842.345 891.353 816.016 681.678 955.821 1036.46 1399.34 2155.01 866.08 638.147 1153.79 773.867 581.398 740.464 893.444 986.618 645.281 986.128 991.589 470.131 712.587 1365.01 1119.35 508.168 761.98 605.37 704.026 651.014 558.048 787.297 795.308 656.052 827.697 554.5135421_MZ Ceramide with formula C34H69NO4 Un 1.0 None None None None Cer(t18:0/16:0) belongs to the class of phytoceramides (N-Acyl-4-hydroxysphinganine), which are involved in sphingolipid metabolism. Phytoceramides are generated from dihydroceramides via the enzyme C4-hydroxylase [EC:1.14.-.-], and are then converted to phytosphingosine via the enzyme N-acylsphingosine amidohydrolase [EC:3.5.1.23]. C34H69NO4 None None None 1402.34 1090.48 1099.74 819.971 1033.52 619.341 1359.77 1500.03 869.449 632.58 1076.43 1795.48 667.358 1117.51 653.236 1302.81 1302.18 1435.05 902.596 1286.3 939.962 1044.37 1030.13 943.636 1032.05 1355.05 1047.18 1178.62 834.788 1104.73 676.171 446.535 1470.56 620.844 559.755 685.474 1136.59 1281.04 817.694 722.333 530.247 935.706 555.4389784_MZ B-Carotene Un 1.0 None None None None B-Carotene is a carotenoid that is a precursor of vitamin A. It is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (porphyria, erythropoietic). (From Reynolds JEF(Ed): Martindale: The Extra Pharmacopoeia (electronic version). Micromedex, Inc, Engewood, CO, 1995.) -- Pubchem; Carotene is an orange photosynthetic pigment important for photosynthesis. It is responsible for the orange colour of the carrot and many other fruits and vegetables. It contributes to photosynthesis by transmitting the light energy it absorbs to chlorophyll. Chemically, carotene is a terpene. It is the dimer of retinol (vitamin A) and comes in two primary forms: alpha- and beta-carotene. gamma-, delta- and epsilon-carotene also exist. Carotene can be stored in the liver and converted to vitamin A as needed. Beta-carotene is an anti-oxidant and such can be useful for curbing the excess of damaging free radicals in the body. However, the usefulness of beta-carotene as a dietary supplement (i.e. taken as a pill) is still subject to debate. Beta-carotene is fat-soluble, so a small amount of fat is needed to absorb it into the body. -- Wikipedia. C40H56, cis-y,y-Carotene, cis-b,b-Carotene, Lycopene, Alpha-Carotene None None None 5912.55 2961.79 2024.84 4244.73 4532.35 3439.06 2936.69 2719.06 4552.99 3819.66 2918.78 2878.15 1614.95 5167.15 4937.83 3594.44 4070.62 3628.29 2688.51 3121.0 3289.37 1436.77 3053.94 4162.94 3766.04 2305.72 3293.27 4509.41 1336.56 3176.85 4255.95 4199.64 1722.59 3891.27 1477.12 3060.99 2596.22 1678.96 1585.22 2442.39 1761.13 3407.57 558.5172847_MZ Ceramide with formula C34H69NO3 Un 1.0 None None None None Ceramides (N-acylsphingosine) are one of the hydrolysis byproducts of sphingomyelin by the enzyme sphingomyelinase (sphingomyelin phosphorylcholine phosphohydrolase E.C.3.1.4.12) which has been identified in the subcellular fractions of human epidermis (PMID 25935) and many other tissues. They can also be synthesized from serine and palmitate in a de novo pathway and are regarded as important cellular signals for inducing apoptosis (PMID 14998372). Is key in the biosynthesis of glycosphingolipids and gangliosides. C34H69NO3 None None None 1369.69 837.161 529.192 754.327 953.254 627.035 1251.49 1093.08 628.006 694.395 867.018 772.865 1176.48 786.387 599.951 1032.08 942.805 1671.19 527.395 1010.96 819.946 580.419 651.065 816.691 737.664 964.237 490.508 980.614 550.009 673.59 940.779 831.45 922.183 493.327 394.753 678.838 678.714 600.929 1021.32 588.774 751.579 970.192 559.4373913_MZ Diglyceride with formula C35H60O5 Un 1.0 None None None None DG(14:0/18:4(6Z,9Z,12Z,15Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(14:0/18:4(6Z,9Z,12Z,15Z)/0:0), in particular, consists of one chain of myristic acid at the C-1 position and one chain of stearidonic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the stearidonic acid moiety is derived from seed oils. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C35H60O5 None None None 1317.37 1122.49 957.557 1238.81 1166.7 1220.7 1398.67 1227.12 907.457 1008.07 1135.38 1044.38 854.871 1280.68 1042.97 1614.62 1418.61 1313.65 889.642 1200.89 1089.72 760.604 1296.71 1225.19 1142.74 772.815 976.629 1186.03 822.183 1090.18 1491.75 1573.69 705.866 1084.47 760.849 871.086 767.752 862.344 812.362 926.283 1239.86 992.841 559.4711639_MZ Diglyceride with formula C33H64O5 Un 1.0 None None None None DG(14:0/16:0/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(14:0/16:0/0:0), in particular, consists of one chain of myristic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C33H64O5 None None None 43872.3 11579.3 5356.64 20020.5 31890.4 17807.8 11363.8 6236.41 25033.2 23756.1 10280.9 6985.81 5152.53 33244.9 42710.8 15782.3 7587.55 27681.0 14466.0 13234.3 19707.3 3651.46 9796.58 28115.9 13281.8 8179.15 20052.1 24707.6 3242.73 12263.2 23825.9 27541.0 5004.26 21000.3 3931.69 12028.3 9041.33 3907.93 4691.14 9767.3 5100.66 24334.1 561.3779785_MZ Cholesterol glucuronide Un 1.0 None None None None Cholesterol glucuronide is a natural human metabolite of Cholesterol generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys. C33H54O7 None None None 2579.56 2211.63 1712.22 2380.75 2427.36 2233.11 2116.34 2005.49 2066.72 2041.87 2454.12 2269.1 2117.27 2707.4 1934.3 2260.89 2263.91 2648.03 1655.02 3710.22 1892.01 1536.95 2088.11 2178.52 2418.63 2084.63 1824.06 2194.88 1730.53 2935.58 2936.76 2336.1 2062.86 2227.71 1573.1 2206.67 1464.81 1566.99 1202.26 2087.35 2892.09 1921.01 561.4530314_MZ Diglyceride with formula C35H62O5 Un 1.0 None None None None DG(14:0/18:3(6Z,9Z,12Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(14:0/18:3(6Z,9Z,12Z)/0:0), in particular, consists of one chain of myristic acid at the C-1 position and one chain of g-linolenic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the g-linolenic acid moiety is derived from animal fats. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C35H62O5 None None None 1638.01 772.791 824.213 1532.52 1198.49 733.654 973.787 1586.16 1350.11 777.887 1017.27 1220.12 1058.86 942.638 948.812 1935.09 1441.19 1707.15 529.992 1270.32 757.579 860.775 782.422 954.442 854.347 1137.18 656.362 1122.54 1318.53 1192.37 1003.93 1378.17 1047.76 1147.25 650.961 603.603 696.835 744.229 667.196 793.333 1015.26 636.037 562.5191705_MZ Ceramide with formula C36H69NO3 Un 1.0 None None None None Ceramides (N-acylsphingosine) are one of the hydrolysis byproducts of sphingomyelin by the enzyme sphingomyelinase (sphingomyelin phosphorylcholine phosphohydrolase E.C.3.1.4.12) which has been identified in the subcellular fractions of human epidermis (PMID 25935) and many other tissues. They can also be synthesized from serine and palmitate in a de novo pathway and are regarded as important cellular signals for inducing apoptosis (PMID 14998372). Is key in the biosynthesis of glycosphingolipids and gangliosides. C36H69NO3 None None None 3004.27 1020.78 1706.85 2800.17 3193.11 1145.59 2925.17 1336.43 2743.99 2455.35 2533.13 1848.24 1681.06 2371.04 2895.26 1004.35 1819.19 3773.75 1490.4 2509.8 1506.04 1096.29 1699.0 2118.49 2065.82 2561.36 1899.73 2578.59 769.461 1502.82 1568.3 1592.18 2591.7 2683.19 930.359 1346.54 2139.28 3220.23 1864.18 1748.33 2260.93 2556.24 563.0660276_MZ dTDP-D-glucose Un 1.0 None None None None Deoxythymidine diphosphate-glucose is an intermediate in the nucleotide sugar metabolism pathway (KEGG). It is a substrate for the enzyme dTDP-D-glucose 4,6-dehydratase which catalyzes the reaction: dTDP-glucose = dTDP-4-dehydro-6-deoxy-D-glucose + H2O. C16H26N2O16P2, dTDP-D-galactose None None None 37891.9 42140.5 41802.9 34336.7 44499.2 38772.6 48156.6 49888.2 40819.5 32810.8 40990.3 46470.6 39434.0 38804.2 47259.1 44029.5 52542.2 32593.9 39982.0 36828.3 44644.5 33240.7 40044.9 39578.4 46665.3 38988.2 55180.5 34451.2 33519.4 34113.0 53160.0 39289.2 39990.7 33891.9 42818.6 32943.6 38599.7 45637.1 24093.4 37623.7 39199.7 38531.1 563.1116729_MZ Theaflavin Un 1.0 None None None None Theaflavins are polyphenols that are formed from catechins in tea leaves during the enzymatic oxidation (called fermentation by the tea trade) of tea leaves (Wikipedia). C29H24O12 None None None 2683.44 3100.71 3323.96 2547.66 2898.38 3301.15 3177.44 3234.9 3126.31 2903.9 2931.2 3640.55 2746.18 2912.88 3265.41 3406.54 3046.66 2657.9 3048.71 2878.16 3044.81 3195.94 2960.52 2900.72 2944.22 3159.97 3505.7 2977.61 3312.66 3428.39 3378.41 3105.28 3038.23 2599.83 3642.16 2961.82 2825.29 3535.33 1877.1 3011.65 2881.11 2604.03 563.4688423_MZ Diglyceride with formula C35H64O5 Un 1.0 None None None None DG(14:0/18:2(9Z,12Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(14:0/18:2(9Z,12Z)/0:0), in particular, consists of one chain of myristic acid at the C-1 position and one chain of linoleic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the linoleic acid moiety is derived from seed oils. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C35H64O5 None None None 629.892 502.744 500.719 569.886 501.14 505.027 618.448 1137.11 453.367 588.648 523.103 596.738 528.59 468.466 660.349 1101.87 1145.53 801.064 395.511 772.091 532.806 441.135 545.806 586.762 619.718 494.941 483.5 531.521 326.257 523.858 770.923 571.201 383.725 465.94 364.718 345.501 340.237 324.284 426.155 465.394 617.946 506.479 564.5354708_MZ Ceramide with formula C36H71NO3 Un 1.0 None None None None Ceramides (N-acylsphingosine) are one of the hydrolysis byproducts of sphingomyelin by the enzyme sphingomyelinase (sphingomyelin phosphorylcholine phosphohydrolase E.C.3.1.4.12) which has been identified in the subcellular fractions of human epidermis (PMID 25935) and many other tissues. They can also be synthesized from serine and palmitate in a de novo pathway and are regarded as important cellular signals for inducing apoptosis (PMID 14998372). Is key in the biosynthesis of glycosphingolipids and gangliosides. C36H71NO3 None None None 9699.25 3555.46 7259.01 9820.34 8277.07 2556.01 17100.8 8865.13 8358.96 7654.87 11165.5 8445.53 9223.57 6797.79 9243.19 2563.38 8260.76 16512.6 5784.26 10985.6 4813.55 3363.08 4383.81 6233.08 5911.77 11038.0 4956.44 9579.32 2011.52 5724.92 4388.94 3991.97 14117.7 7836.63 2545.06 3524.51 7413.29 9947.22 11065.0 5572.52 9276.05 9412.4 565.0468820_MZ Uridine diphosphate glucose Un 1.0 None None None None Uridine diphosphate glucose is a key intermediate in carbohydrate metabolism. Serves as a precursor of glycogen, can be metabolized into UDPgalactose and UDPglucuronic acid which can then be incorporated into polysaccharides as galactose and glucuronic acid. Also serves as a precursor of sucrose lipopolysaccharides, and glycosphingolipids. C15H24N2O17P2, Uridine diphosphategalactose None None None 669769.0 679294.0 625265.0 369492.0 669300.0 676578.0 883144.0 841303.0 545010.0 553420.0 688180.0 657588.0 859052.0 689133.0 655232.0 603759.0 841974.0 458911.0 757957.0 647028.0 735722.0 556801.0 493667.0 600657.0 753700.0 543212.0 891075.0 541958.0 394831.0 642888.0 872206.0 448803.0 681711.0 531546.0 678218.0 501928.0 558057.0 758620.0 349792.0 461566.0 747515.0 747695.0 565.4101875_MZ 3-Hydroxy-b_e-caroten-3'-one Un 1.0 None None None None 3-Hydroxy-caroten-3'-one is a carotenoid found in human fluids. Carotenoids are isoprenoid molecules that are widespread in nature and are typically seen as pigments in fruits, flowers, birds and crustacea. Animals are unable to synthesise carotenoids de novo, and rely upon the diet as a source of these compounds. Over recent years there has been considerable interest in dietary carotenoids with respect to their potential in alleviating age-related diseases in humans. This attention has been mirrored by significant advances in cloning most of the carotenoid genes and in the genetic manipulation of crop plants with the intention of increasing levels in the diet. Studies have shown an inverse relationship between the consumption of certain fruits and vegetables and the risk of epithelial cancer. Since carotenoids are among the micronutrients found in cancer preventive foods, detailed qualitative and quantitative determination of these compounds, particularly in fruits and vegetables and in human plasma, have recently become increasingly important. (PMID: 1416048, 15003396). C40H54O2 None None None 890.192 1064.03 843.68 861.425 888.252 1449.34 890.687 1469.02 841.016 799.661 956.567 755.973 428.462 909.313 1141.62 1229.48 2091.36 785.269 580.164 1205.94 670.649 509.479 915.441 743.706 903.754 534.532 807.824 890.445 462.148 1220.45 1123.62 921.576 582.713 808.991 612.392 731.69 532.977 567.732 725.815 835.678 791.907 705.694 567.2979874_MZ Protoporphyrinogen IX Un 1.0 None None None None Protoporphyrinogen IX is an intermediate in heme biosynthesis. It is a porphyrinogen in which 2 pyrrole rings each have one methyl and one propionate side chain and the other two pyrrole rings each have one methyl and one vinyl side chain. 15 isomers are possible but only one, type IX, occurs naturally. Protoporphyrinogen is produced by oxidative decarboxylation of coproporphyrinogen. C34H40N4O4 None None None 4309.07 4365.89 4521.57 4781.01 3674.05 6725.72 3392.57 2759.09 2649.66 3493.68 4838.8 6223.8 3196.53 5330.39 3388.26 3733.98 7585.97 2396.83 3423.04 3466.59 4236.89 2694.37 4049.16 4369.47 4584.19 2419.16 4888.21 3552.35 2566.05 4940.66 5282.67 2852.55 1877.82 2451.42 6726.71 2807.23 3626.16 2926.36 1445.36 3281.7 2998.84 4147.47 568.3522274_MZ Lysophospholipid with formula C30H52NO7P Un 1.0 None None None None LysoPC(22:5(4Z,7Z,10Z,13Z,16Z)) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(22:5(4Z,7Z,10Z,13Z,16Z)), in particular, consists of one chain of docosapentaenoic acid at the C-1 position. The docosapentaenoic acid moiety is derived from animal fats and brain. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. In blood plasma significant amounts of lysophosphatidylcholine are formed by a specific enzyme system, lecithin:cholesterol acyltransferase (LCAT), which is secreted from the liver. The enzyme catalyzes the transfer of the fatty acids of position sn-2 of phosphatidylcholine to the free cholesterol in plasma, with formation of cholesterol esters and lysophosphatidylcholine. Lysophospholipids have a role in lipid signaling by acting on lysophospholipid receptors (LPL-R). LPL-R's are members of the G protein-coupled receptor family of integral membrane proteins. C30H52NO7P None None None 2036.41 1628.18 1737.1 1641.69 1691.35 2313.45 1826.9 1628.57 1685.57 1803.4 2245.04 1976.99 1843.17 1873.64 1615.24 1918.48 1725.77 2714.74 1476.3 2144.69 1679.52 1570.08 1911.72 1613.25 1820.33 1568.47 1420.85 2002.58 1610.59 1938.05 1586.35 1580.08 1890.46 1365.32 1481.55 1805.2 1252.35 1590.28 1068.1 1842.24 1456.86 1459.13 569.0573033_MZ UDP-L-rhamnose Un 1.0 None None None None UDP-L-rhamnose is synthesized from UDP-D-glucose. C15H24N2O16P2 None None None 3788.44 3708.57 3916.45 3909.8 4220.66 4608.16 3789.34 3544.62 4036.62 4334.25 3753.38 4356.22 4651.9 3893.07 5018.94 5795.27 3495.2 4097.02 4190.15 3970.43 3840.84 3809.64 3476.33 3733.79 4091.9 3936.19 4299.42 4024.78 4003.8 3645.52 4873.24 5043.62 4266.02 3200.88 4434.14 4381.93 3816.14 4758.83 2617.28 3856.54 4830.19 3758.28 571.2873879_MZ Kinetensin 4-7 Un 1.0 None None None None Kinetensin 4-7 is a fraction of Kinetensin with only Arg-His-Pro-Tyr peptide chains. Kinetensin is a nonapeptide, originally isolated from pepsin-treated plasma that shares some sequence homology with the C-terminal end of neurotensin, serum albumin and angiotensin. It is a potent histamine releaser in rodents and may serve as an inflammatory mediator. C26H38N9O6 None None None 10158.2 12742.5 11180.1 17022.0 14701.4 13724.9 9271.65 9422.12 11502.1 11138.4 12026.9 16450.6 9158.83 13447.8 11639.8 13532.2 10606.5 17896.9 8369.22 11974.1 12910.6 10034.4 12085.4 10939.5 13281.5 10087.8 10637.8 10093.2 8646.75 12322.5 11466.9 13676.6 9318.91 8569.04 8254.18 10325.5 12080.2 10244.0 7159.64 12330.0 8883.68 9690.34 573.1941745_MZ Tetrahydrofolyl-[Glu](2) Un 1.0 None None None None Tetrahydrofolyl-[Glu](n) is involved in the folate biosynthesis pathway. Tetrahydrofolyl-[Glu](n) can be reversibly converted into Tetrahydrofolyl-[Glu](2) by folylpolyglutamate synthase [EC:6.3.2.17]. Tetrahydrofolyl-[Glu](n) can be irreversibly converted into tetrahydrofolate by gamma-glutamyl hydrolase [EC:3.4.19.9]. C24H30N8O9 None None None 1657.86 1476.71 1944.9 1609.72 1803.46 2238.22 1697.16 1492.34 1466.94 1606.07 1708.2 1681.34 1231.39 1803.96 1864.33 2112.37 2063.56 1419.83 1482.59 1758.36 1786.2 1561.05 1810.35 1756.11 1688.37 1762.72 1854.0 1641.26 1650.48 1869.93 1446.94 1360.27 1375.93 1155.05 1740.74 1781.68 1405.85 1552.8 921.346 1859.03 1516.7 1584.33 579.0154025_MZ Uridine diphosphate glucuronic acid Un 1.0 None None None None Uridine diphosphate glucuronic acid is a nucleoside diphosphate sugar which serves as a source of glucuronic acid for polysaccharide biosynthesis. It may also be epimerized to UDP Iduronic acid, which donates Iduronic acid to polysaccharides. In animals, UDP glucuronic acid is used for formation of many glucosiduronides with various aglycones. The transfer of glucuronic acid from UDP-alpha-D-glucuronic acid onto a terminal galactose residue is done by beta1,3-glucuronosyltransferases, responsible for the completion of the protein-glycosaminoglycan linkage region of proteoglycans and of the HNK1 epitope of glycoproteins and glycolipids. In humans the enzyme galactose-beta-1,3-glucuronosyltransferase I completes the synthesis of the common linker region of glycosaminoglycans (GAGs) by transferring glucuronic acid (GlcA) onto the terminal galactose of the glycopeptide primer of proteoglycans. The GAG chains of proteoglycans regulate major biological processes such as cell proliferation and recognition, extracellular matrix deposition, and morphogenesis. (PMID: 16815917). C15H22N2O18P2, UDP-D-galacturonate, UDP-L-iduronate None None None 50064.1 40357.4 38324.9 24117.1 36373.7 35017.8 53376.7 39545.1 31187.8 26189.2 41144.1 33089.0 24872.7 36158.4 36534.2 31621.8 36410.8 25179.4 31241.7 35101.2 43250.5 36486.6 33040.1 48575.3 30143.3 36747.2 40081.3 34366.8 29466.8 35823.2 48948.1 30382.9 30958.1 31014.9 34178.4 31879.2 28931.9 33464.7 15953.8 34884.9 25772.6 39262.1 580.4213464_MZ Ceramide Phosphated18:1/12:0) Un 1.0 None None None None CerP(d18:1/12:0) or N-(dodecanoyl)-sphing-4-enine-1-phosphate is a ceramide 1-phosphate belonging to the sphingolipid class of molecules. Ceramides are amides of fatty acids with long-chain di- or trihydroxy bases, the commonest in animals being sphingosine and in plants phytosphingosine. The acyl group of ceramides is generally a long-chain saturated or monounsaturated fatty acid. The most frequent fatty acids found in animal ceramides are 18:0, 24:0 and 24:1(n-9). Ceramide 1-phosphates are produced by phosphorylation of ceramide by a specific ceramide kinase. Ceramide-1-phosphate was shown to be a specific and potent inducer of arachidonic acid and prostanoid synthesis in cells through the translocation and activation of the cytoplasmic phospholipase A2. C30H60NO6P None None None 793.407 854.338 781.398 840.783 739.285 1012.76 1702.21 1415.14 638.228 557.064 856.398 679.983 1081.59 608.51 720.874 1473.52 2008.67 1159.4 595.612 1277.28 537.51 316.409 696.868 617.734 856.882 624.243 731.417 1302.1 414.088 814.884 1496.6 1130.14 377.638 878.691 624.615 625.286 364.476 456.125 619.165 600.931 1364.25 675.61 581.5192501_MZ Diglyceride with formula C36H70O5 Un 1.0 None None None None DG(15:0/18:0/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(15:0/18:0/0:0), in particular, consists of one chain of pentadecanoic acid at the C-1 position and one chain of stearic acid at the C-2 position. The pentadecanoic acid moiety is derived from dairy products and milk fat, while the stearic acid moiety is derived from animal fats, coco butter and sesame oil. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C36H70O5 None None None 1141.61 1241.7 1101.36 1251.7 1202.78 1232.75 1246.5 1670.79 1055.5 1219.29 1203.68 991.315 861.665 1096.95 1415.84 2043.07 1807.38 953.681 821.666 1096.1 836.851 821.748 842.344 1020.02 1109.66 952.326 1135.59 1009.2 891.005 1008.0 1620.44 1586.88 996.382 791.39 863.099 872.235 869.337 1060.21 890.134 952.971 1210.33 1074.45 585.4609022_MZ Diglyceride with formula C37H62O5 Un 1.0 None None None None DG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/0:0), in particular, consists of one chain of myristic acid at the C-1 position and one chain of eicosapentaenoic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the eicosapentaenoic acid moiety is derived from fish oils, liver and kidney. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C37H62O5 None None None 1314.43 928.563 829.824 1395.99 1176.63 1130.47 1116.49 1388.8 855.756 1180.1 1228.06 629.539 1537.88 1186.74 842.795 1344.71 1290.87 2244.85 821.878 1393.91 875.797 534.373 1035.24 1270.24 1212.96 643.366 916.045 1042.8 501.001 933.956 1312.39 1489.58 695.944 863.076 627.366 1068.73 866.652 829.361 925.869 898.919 1202.81 1291.5 585.4884711_MZ Diglyceride with formula C35H66O5 Un 1.0 None None None None DG(14:1(9Z)/18:0/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(14:1(9Z)/18:0/0:0), in particular, consists of one chain of myristoleic acid at the C-1 position and one chain of stearic acid at the C-2 position. The myristoleic acid moiety is derived from milk fats, while the stearic acid moiety is derived from animal fats, coco butter and sesame oil. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C35H66O5 None None None 33032.0 7084.88 17306.3 12931.0 25059.5 9428.62 27063.4 26225.1 14473.7 10723.6 16769.1 11471.8 53758.9 26831.0 15723.6 6872.35 5752.4 114439.0 12091.0 28063.4 13482.9 9370.32 10285.1 47843.2 25951.2 13289.4 11084.7 22946.9 9252.32 10047.7 14418.9 10061.3 24937.5 11371.9 4561.88 26417.5 21134.2 9666.21 21193.0 12478.8 46348.6 44309.2 586.3245477_MZ LysoPhosphatidylcholine (22:6(4Z,7Z,10Z,13Z,16Z,19Z)) Un 1.0 None None None None LysoPC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of docosahexaenoic acid at the C-1 position. The docosahexaenoic acid moiety is derived from fish oils. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. In blood plasma significant amounts of lysophosphatidylcholine are formed by a specific enzyme system, lecithin:cholesterol acyltransferase (LCAT), which is secreted from the liver. The enzyme catalyzes the transfer of the fatty acids of position sn-2 of phosphatidylcholine to the free cholesterol in plasma, with formation of cholesterol esters and lysophosphatidylcholine. Lysophospholipids have a role in lipid signaling by acting on lysophospholipid receptors (LPL-R). LPL-R's are members of the G protein-coupled receptor family of integral membrane proteins. C30H50NO7P None None None 9365.35 8785.36 3530.31 10913.7 3796.87 5626.28 3757.93 4381.19 7282.17 5752.79 5932.88 3990.42 4076.48 8065.66 3597.04 3244.33 4347.96 4627.75 3227.56 5002.15 7752.0 3108.9 5303.81 10213.4 5929.96 3270.51 3233.27 3945.57 3290.98 10966.3 3619.98 4143.99 3983.24 5539.62 3058.9 9108.61 5527.01 3344.3 2440.2 8581.78 5330.3 6645.9 588.0813018_MZ ADP-glucose Un 1.0 None None None None Serves as the glycosyl donor for formation of bacterial glycogen, amylose in green algae, and amylopectin in higher plants. C16H25N5O15P2, ADP-Mannose, GDP-D-Rhamnose, GDP-L-fucose None None None 15597.9 10624.1 12663.0 8002.74 15462.4 15725.3 20304.2 16332.5 11280.7 10158.6 12280.5 13677.0 27077.4 11215.2 15130.8 17311.5 14333.6 21730.8 17676.8 17460.1 17111.6 8876.82 14161.8 12619.1 17111.6 12193.8 19789.3 13077.1 9354.55 11349.0 19330.0 12309.5 10059.5 9746.92 8969.84 13185.8 10432.5 12632.1 8390.79 12531.3 20612.1 17332.8 588.0924485_MZ dTDP-4-acetamido-4,6-dideoxy-D-galactose Un 1.0 None None None None dTDP-4-acetamido-4,6-dideoxy-D-galactose reacts with undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate to produce undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate and dTDP. The reaction is catalyzed by certain members of the fucosyltransferase family of enzymes. C18H29N3O15P2 None None None 13857.0 11473.3 11171.9 9201.87 13084.5 12073.8 16789.7 12983.0 10859.7 8980.3 9869.73 13951.2 22181.1 10822.0 12617.3 15707.2 10132.8 16930.7 15408.7 15183.3 13125.4 9584.56 12212.1 10836.2 13706.9 11652.2 18485.7 12049.4 10175.2 9878.83 14289.7 11783.9 11292.1 9617.82 10620.6 12383.4 9865.02 14219.2 7210.57 12845.8 16162.6 15851.7 591.4955099_MZ Diglyceride with formula C37H68O5 Un 1.0 None None None None DG(14:0/20:2(11Z,14Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(14:0/20:2(11Z,14Z)/0:0), in particular, consists of one chain of myristic acid at the C-1 position and one chain of eicosadienoic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the eicosadienoic acid moiety is derived from fish oils and liver. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C37H68O5 None None None 1287.11 695.65 693.664 951.178 797.767 675.362 940.61 1464.84 526.826 596.351 689.471 753.25 1048.5 823.665 875.44 1660.3 1201.28 2436.14 512.145 1453.69 530.056 512.081 650.467 817.713 857.326 653.266 680.08 965.135 651.567 661.619 1241.23 1023.86 614.061 571.448 287.034 616.198 494.228 449.038 602.215 537.351 1387.48 774.145 592.5661995_MZ Ceramide (d18:1/20:0) Un 1.0 None None None None Ceramides (N-acylsphingosine) are one of the hydrolysis byproducts of sphingomyelin by the enzyme sphingomyelinase (sphingomyelin phosphorylcholine phosphohydrolase E.C.3.1.4.12) which has been identified in the subcellular fractions of human epidermis (PMID 25935) and many other tissues. They can also be synthesized from serine and palmitate in a de novo pathway and are regarded as important cellular signals for inducing apoptosis (PMID 14998372). Is key in the biosynthesis of glycosphingolipids and gangliosides. C38H75NO3 None None None 21382.5 15538.8 19334.6 15014.1 16718.7 8840.51 41404.8 17723.1 13990.2 10162.0 25945.6 27902.6 22535.3 12582.2 15077.4 10007.8 18032.1 43001.6 15273.3 30358.3 10413.4 5427.86 10833.4 21907.1 17900.6 17318.5 11223.6 28822.7 7748.16 13304.2 14072.5 9526.71 32832.5 16590.5 5159.01 9846.85 12592.0 22024.9 38199.7 11236.9 24325.4 15556.9 593.4560403_MZ Diglyceride with formula C36H62O5 Un 1.0 None None None None DG(15:0/18:4(6Z,9Z,12Z,15Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(15:0/18:4(6Z,9Z,12Z,15Z)/0:0), in particular, consists of one chain of pentadecanoic acid at the C-1 position and one chain of stearidonic acid at the C-2 position. The pentadecanoic acid moiety is derived from dairy products and milk fat, while the stearidonic acid moiety is derived from seed oils. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C36H62O5 None None None 5809.95 7611.68 2966.67 3697.99 4549.11 6267.21 6525.72 4538.26 4003.73 5282.38 8454.87 7893.31 2909.1 4166.92 3330.47 7028.72 7811.92 2111.38 4218.38 3959.64 4219.82 2148.27 6181.63 3628.36 4568.3 2891.67 6915.15 5518.48 1743.63 6772.9 5013.02 3822.61 3530.14 3906.25 2540.59 3069.03 3231.56 2850.23 1155.86 3872.95 5010.45 2305.97 594.2312026_MZ Taurocholic acid 3-sulfate Un 1.0 None None None None Taurocholic acid 3-sulfate is a sulfated bile acid. It is a sulfate salt of taurocholic acid and is also known as cholaic acid, cholyltaurine, or acidum cholatauricum. Under normal circumstances, bile acid sulfation is a minor pathway. However in the presence of cholestasis, the fraction of the bile acid pool which is sulfated increases. Sulfation of bile acids increases the aqueous solubility of the amphipathic compounds and results in more efficient renal clearance as well as in decreased reabsorption from the intestinal lumen. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487, 16037564, 12576301, 11907135). C26H45NO10S2 None None None 9635.13 7888.31 10495.1 10233.1 7853.9 9239.73 10368.2 7709.85 7983.25 11934.2 8172.56 9356.96 7390.23 11602.2 9064.76 9267.13 12864.3 8449.26 12291.4 9951.1 10419.9 8689.88 9724.02 9187.58 12479.2 7397.69 13753.1 8922.04 10103.4 12370.8 8928.34 8061.61 7551.65 8078.57 11232.2 9588.75 8707.22 9681.15 6941.04 10831.0 9408.38 15280.2 594.2574241_MZ Taurocholic acid 3-sulfate Un 1.0 None None None None Taurocholic acid 3-sulfate is a sulfated bile acid. It is a sulfate salt of taurocholic acid and is also known as cholaic acid, cholyltaurine, or acidum cholatauricum. Under normal circumstances, bile acid sulfation is a minor pathway. However in the presence of cholestasis, the fraction of the bile acid pool which is sulfated increases. Sulfation of bile acids increases the aqueous solubility of the amphipathic compounds and results in more efficient renal clearance as well as in decreased reabsorption from the intestinal lumen. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487, 16037564, 12576301, 11907135). C26H45NO10S2 None None None 2741.63 2349.98 3274.74 3026.37 2340.07 3344.81 2993.84 1752.21 2298.28 3654.98 2441.27 2997.12 2059.3 3385.76 2974.54 2975.09 3344.51 1858.77 3518.56 2699.11 2780.25 2342.18 3185.31 2882.44 3215.95 2178.47 4053.35 2263.75 2651.09 3821.95 2393.94 2890.73 1731.36 2236.02 2984.99 2834.99 2306.67 2622.52 1774.21 3162.75 2730.7 3870.97 595.2347916_MZ Tetragastrin Un 1.0 None None None None Tetragastrin is the C-terminal tetrapeptide of gastrin. It is the smallest peptide fragment of gastrin which has the same physiological and pharmacological activity as gastrin. C29H36N6O6S None None None 3685.45 3076.22 4045.02 3993.34 3102.23 3898.16 3856.77 2958.07 3070.39 4427.31 2836.48 3482.08 2953.41 4377.55 3948.58 3596.68 4980.59 3125.11 4450.38 3446.81 4178.01 3116.47 3872.32 3651.21 4503.53 2894.24 4938.02 3280.95 3623.77 4600.0 3152.19 3269.73 2789.91 3045.98 4044.39 3751.27 3126.25 3228.77 2683.71 3911.1 3551.38 5422.62 595.5330550_MZ Diglyceride with formula C37H72O5 Un 1.0 None None None None DG(14:0/20:0/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(14:0/20:0/0:0), in particular, consists of one chain of myristic acid at the C-1 position and one chain of arachidic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the arachidic acid moiety is derived from peanut oil. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol. Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C37H72O5 None None None 920.594 933.574 1211.33 676.68 1504.02 878.415 1651.23 2015.41 836.657 919.039 1115.07 896.411 790.633 1045.6 1683.74 1678.25 2209.12 410.37 878.936 1502.18 873.331 517.531 913.071 929.371 1253.96 863.755 1598.29 571.864 328.986 751.479 2839.7 1428.67 989.484 906.617 420.131 541.106 625.31 765.383 382.555 621.951 1217.51 728.522 596.0771338_MZ PhosphoribosylformiminoAICAR-phosphate Un 1.0 None None None None none C15H25N5O15P2, Phosphoribulosylformimino-AICAR-P None None None 3027.92 2609.46 3659.19 2527.43 3510.35 3214.18 3630.95 3218.96 3841.88 2550.1 2616.75 3022.92 3415.17 2590.79 3152.46 2937.36 3285.89 3266.24 3115.49 3189.16 3824.04 3206.08 2952.8 2962.89 2816.34 3224.67 3733.33 2977.85 3167.05 2971.88 3256.06 2893.44 3441.18 2874.65 3410.44 3596.89 2838.11 3172.7 1977.83 3002.65 3328.19 3383.63 597.4865306_MZ Diglyceride with formula C36H66O5 Un 1.0 None None None None DG(15:0/18:2(9Z,12Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(15:0/18:2(9Z,12Z)/0:0), in particular, consists of one chain of pentadecanoic acid at the C-1 position and one chain of linoleic acid at the C-2 position. The pentadecanoic acid moiety is derived from dairy products and milk fat, while the linoleic acid moiety is derived from seed oils. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C36H66O5 None None None 2775.64 2150.4 2139.1 2834.5 2230.05 2223.47 3792.86 3386.05 2218.65 2006.18 2507.09 2218.21 3623.31 3057.6 2096.0 2327.66 2598.25 5855.02 1804.37 3473.9 2143.28 1520.47 2245.16 3655.69 2772.03 1944.48 2086.39 3103.55 1557.59 2359.01 3042.97 2223.33 2205.34 2095.52 1225.88 2781.34 2248.55 1741.49 2416.82 1906.12 3747.9 3406.68 599.4168991_MZ Neoxanthin Un 1.0 None None None None Neoxanthin is a carotenoid, an intermediate in the synthesis of abscisic acid from violaxanthin. Neoxanthin is found in apple. Neoxanthin is a constituent of paprika, lucerne, Valencia orange and other species. Neoxanthin has been shown to exhibit apoptotic and anti-proliferative functions (PMID 15333710, 15333710). C40H56O4, Violaxanthin None None None 1140.57 1027.97 837.62 1581.37 1056.56 1162.12 1160.26 1202.33 799.766 900.073 1110.95 773.688 472.935 1096.22 1040.2 1471.6 1427.39 1071.24 682.415 1075.89 755.173 509.297 1082.07 1039.02 992.998 678.226 834.262 994.704 648.62 1146.13 1311.83 1483.23 669.44 942.005 717.418 957.649 658.107 598.184 580.54 855.107 804.897 866.822 599.4984222_MZ Diglyceride with formula C36H68O5 Un 1.0 None None None None DG(15:0/18:1(11Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(15:0/18:1(11Z)/0:0), in particular, consists of one chain of pentadecanoic acid at the C-1 position and one chain of vaccenic acid at the C-2 position. The pentadecanoic acid moiety is derived from dairy products and milk fat, while the vaccenic acid moiety is derived from butter fat and animal fat. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C36H68O5 None None None 4536.03 1953.33 2414.35 3484.53 3486.67 2297.61 5481.73 5034.97 2480.08 3054.51 3252.83 2751.29 4885.07 3810.42 2594.4 2449.09 2151.03 9113.08 1957.53 4190.65 2477.68 1799.78 2549.93 5637.57 3330.84 2620.18 2320.92 4220.17 1897.64 2338.76 2920.05 2747.47 3383.63 2141.95 1413.67 3511.51 3395.22 2507.75 3848.09 2411.11 4447.64 5195.54 601.4645424_MZ Diglyceride with formula C38H66O5 Un 1.0 None None None None DG(15:0/20:4(5Z,8Z,11Z,14Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(15:0/20:4(5Z,8Z,11Z,14Z)/0:0), in particular, consists of one chain of pentadecanoic acid at the C-1 position and one chain of arachidonic acid at the C-2 position. The pentadecanoic acid moiety is derived from dairy products and milk fat, while the arachidonic acid moiety is derived from animal fats and eggs. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C38H66O5 None None None 5355.89 1945.27 2904.05 5327.26 5808.05 2677.53 5379.29 4743.89 2715.86 2826.45 3751.4 2320.5 10871.7 6553.43 2376.95 4137.82 1574.75 15506.9 2752.76 4322.59 2592.0 2156.67 2796.65 6273.65 4984.84 2716.72 2699.63 4328.27 2218.77 3203.39 4045.94 4900.74 3702.35 2142.67 1710.49 5662.63 3002.18 1645.05 3085.81 2780.9 9210.59 7592.22 604.0656623_MZ GDP-glucose Un 1.0 None None None None GDP-glucose is a substrate for Uridine diphosphate glucose pyrophosphatase. C16H25N5O16P2, Guanosine diphosphate mannose None None None 23741.9 21019.3 23482.4 13294.8 26123.0 25821.4 33361.2 27574.8 20852.2 17473.5 21573.7 23299.8 27106.1 17789.8 27094.0 25144.0 29856.9 29565.3 29186.1 30489.4 25783.2 17185.3 23144.3 19193.3 28048.5 19303.3 31354.9 19335.3 13798.9 19645.7 26689.8 18479.6 21850.8 18853.6 16655.5 17370.8 19778.4 24648.6 12235.6 18349.2 27965.3 22591.2 605.1884177_MZ Ferricytochrome Un 1.0 None None None None C33H34FeN4O4, Ferrocytochrome None None None 3161.15 4886.13 5535.02 3000.38 3905.59 4442.42 3384.92 2632.61 4514.53 4567.33 3658.88 5287.52 3629.44 5152.3 4692.36 4370.24 4414.26 2810.43 5496.54 4091.6 4579.68 4115.39 4804.26 4345.52 2969.94 4716.03 5371.95 3698.11 5498.41 7466.94 3657.08 2449.12 3843.12 4043.92 4008.46 4765.72 3480.96 3962.46 2359.49 4728.82 13874.7 3413.38 605.5178562_MZ Diglyceride with formula C38H70O5 Un 1.0 None None None None DG(15:0/20:2(11Z,14Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(15:0/20:2(11Z,14Z)/0:0), in particular, consists of one chain of pentadecanoic acid at the C-1 position and one chain of eicosadienoic acid at the C-2 position. The pentadecanoic acid moiety is derived from dairy products and milk fat, while the eicosadienoic acid moiety is derived from fish oils and liver. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C38H70O5 None None None 594.424 355.275 430.884 766.189 514.115 431.682 481.498 764.382 381.323 462.261 486.138 432.237 437.507 499.658 560.442 802.826 708.126 1424.18 225.843 579.76 355.462 163.229 234.701 535.62 447.558 416.518 515.008 427.914 268.96 370.924 822.858 843.97 597.308 349.548 251.016 357.019 376.708 373.694 321.337 256.593 1773.59 509.264 605.9563697_MZ Adenosine tetraphosphate Un 1.0 None None None None Adenosine 5' tetraphosphate, Ap4, is a natural nucleotide present in many biological systems. This nucleotide has been found as a constituent of the nucleotide pool present in the aqueous humor of a number of mammals and appears to act as a regulator of intraocular pressure (PMID: 14600249). AP4 may also play a significant role in the physiological regulation of vascular tone (PMID: 8599250). The plasma concentration of AP4 is in the nanomolar range. Technically adenosine tetraphosphate is condensation product of adenosine with tetraphosphoric acid at the 5' position. Acetyl coenzyme A (CoA) synthetase (EC 6.2.1.1) catalyzes the synthesis of adenosine 5'-tetraphosphate (P4A) and adenosine 5'-pentaphosphate (p5A) from ATP and tri- or tetrapolyphosphate (P3 or P4). C10H17N5O16P4 None None None 5599.45 5844.15 6467.03 7479.76 6945.05 6221.28 6512.25 5643.09 6365.12 5952.51 5467.85 5699.38 6490.33 5566.36 6954.24 7521.85 6614.62 5338.22 6174.92 6003.69 5949.86 5816.77 6363.94 5697.2 6160.31 5780.39 6279.73 5851.02 6194.1 5884.2 6284.42 6455.19 4950.88 5613.28 7313.06 5857.0 5902.79 5989.67 5198.58 6329.92 6204.94 5705.85 606.0729978_MZ UDP-N-acetyl-D-mannosamine Un 1.0 None None None None UDP-N-acetyl-D-mannosamine is involved in teichoic acid (poly-glycerol) biosynthesis pathway and enterobacterial common antigen biosynthesis pathway. It serves as both enzymatic reactants and products in those two pathways. In teichoic acid (poly-glycerol) biosynthesis pathway, UDP-N-acetyl-mannosamine is synthesized from UDP-N-acetyl-glocasamine by UDP-N-acetylglucosamine 2-epimerase, encoded by the mnaA gene. C17H27N3O17P2, Uridine diphosphate-N-acetylgalactosamine None None None 636512.0 749802.0 838982.0 543834.0 895087.0 646706.0 915820.0 980128.0 829383.0 552118.0 759002.0 907435.0 726628.0 711656.0 922143.0 591370.0 1139260.0 567540.0 792826.0 646128.0 845399.0 627338.0 742877.0 695554.0 926855.0 737192.0 1152260.0 592982.0 586712.0 592411.0 948951.0 557954.0 806570.0 621273.0 764654.0 565966.0 793222.0 896540.0 444599.0 653301.0 704423.0 725723.0 606.4448064_MZ LysoPhosphatidylcholine with formula C32H66NO7P Un 1.0 None None None None LysoPC(24:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(24:0), in particular, consists of one chain of lignoceric acid at the C-1 position. The lignoceric acid moiety is derived from groundnut oil. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. In blood plasma significant amounts of lysophosphatidylcholine are formed by a specific enzyme system, lecithin:cholesterol acyltransferase (LCAT), which is secreted from the liver. The enzyme catalyzes the transfer of the fatty acids of position sn-2 of phosphatidylcholine to the free cholesterol in plasma, with formation of cholesterol esters and lysophosphatidylcholine. Lysophospholipids have a role in lipid signaling by acting on lysophospholipid receptors (LPL-R). LPL-R's are members of the G protein-coupled receptor family of integral membrane proteins. C32H66NO7P None None None 981.949 752.174 300.132 613.751 496.541 375.55 332.8 780.895 579.801 293.934 586.89 891.741 524.587 180.756 243.837 985.626 1613.28 282.499 254.682 982.993 382.961 556.142 414.882 326.043 166.619 903.44 610.044 514.479 572.403 450.932 274.774 942.415 326.155 609.69 269.664 240.175 260.345 179.152 238.331 284.99 647.897 180.476 607.4720070_MZ Diglyceride with formula C37H64O5 Un 1.0 None None None None DG(14:0/20:4(5Z,8Z,11Z,14Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(14:0/20:4(5Z,8Z,11Z,14Z)/0:0), in particular, consists of one chain of myristic acid at the C-1 position and one chain of arachidonic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the arachidonic acid moiety is derived from animal fats and eggs. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C37H64O5 None None None 4116.12 2935.96 3147.8 7158.73 3862.51 1953.13 4004.27 3425.73 3945.36 2397.61 3354.11 3432.4 6111.75 3833.38 3083.44 2424.1 3049.39 10438.3 2734.48 4395.15 2080.44 2312.31 3496.26 4076.52 3999.07 2992.44 2923.93 4586.19 2659.97 2500.38 2905.97 2109.32 3913.32 3089.27 1559.53 4032.65 3568.28 3049.66 3200.11 3356.31 5816.04 5084.38 608.2398773_MZ QYNAD Un 1.0 None None None None QYNAD is an endogenous pentapeptide with the sequence Gln-Tyr-Asn-Ala-Asp (QYNAD in the international one letter code of amino acids), isolated from the cerebrospinal fluid (CSF) of patients with multiple sclerosis (MS) and Guillain-Barre syndrome (GBS). Immune mediated inflammatory neurological disorders like MS and GBS are characterized by demyelination and axonal damage. QYNAD can reversibly block voltage-gated sodium channels in a concentration-dependent manner. The blocking mechanism is a shift of the steady state inactivation curve of the sodium channels to more negative potentials, as with many local anaesthetics. QYNAD was found to reach concentrations in the CSF of MS or GBS that could subsantially block neuronal sodium channels. (PMID: 11750990). C25H35N7O11 None None None 893.932 924.003 1143.58 1089.45 1464.29 1813.15 767.547 580.926 843.042 1179.06 990.88 1049.97 662.714 1465.66 1505.44 1095.72 925.079 488.836 1102.13 828.153 1081.15 950.596 1253.33 1270.43 858.031 1155.25 1616.99 671.429 1084.15 1052.31 743.753 898.648 864.865 761.455 1217.11 1034.46 745.003 864.687 353.259 1238.58 695.869 1084.8 609.1854331_MZ Hesperidin Un 1.0 None None None None Hesperidin is an abundant and inexpensive by-product of Citrus cultivation and is the major flavonoid in sweet orange and lemon. In young immature oranges it can account for up to 14% of the fresh weight of the fruit. Hesperidin is an abundant and inexpensive by-product of Citrus cultivation and is the major flavonoid in sweet orange and lemon. In young immature oranges it can account for up to 14% of the fresh weight of the fruit due to vitamin C deficiency such as bruising due to capillary fragility were found in early studies to be relieved by crude vitamin C extract but not by purified vitamin C. The bioflavonoids, formerly called vitamin P, were found to be the essential components in correcting this bruising tendency and improving the permeability and integrity of the capillary lining. These bioflavonoids include hesperidin, citrin, rutin, flavones, flavonols, catechin and quercetin. Of historical importance is the observation that citrin, a mixture of two flavonoids, eriodictyol and hesperidin, was considered to possess a vitamin-like activity, as early as in 1949. Hesperidin deficiency has since been linked with abnormal capillary leakiness as well as pain in the extremities causing aches, weakness and night leg cramps. Supplemental hesperidin also helps in reducing oedema or excess swelling in the legs due to fluid accumulation. As with other bioflavonoids, hesperidin works best when administered concomitantly with vitamin C. No signs of toxicity have been observed with normal intake of hesperidin. Hesperidin was first discovered in 1827, by Lebreton, but not in a pure state and has been under continuous investigation since then (PMID: 11746857). C28H34O15 None None None 1063.36 1140.77 1352.31 877.527 1076.86 2037.13 1011.14 678.931 1152.81 1445.9 1178.31 888.649 1010.72 1300.3 1463.06 1036.24 903.09 1008.06 1489.64 895.197 1607.84 1099.89 1352.35 1202.44 764.5 1037.44 1704.18 1016.14 1188.82 1555.66 703.491 680.797 921.528 808.061 1445.15 1610.84 965.145 832.643 466.608 1466.93 1234.64 1070.41 609.4881603_MZ Diglyceride with formula C37H66O5 Un 1.0 None None None None DG(14:0/20:3(8Z,11Z,14Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(14:0/20:3(8Z,11Z,14Z)/0:0), in particular, consists of one chain of myristic acid at the C-1 position and one chain of homo-g-linolenic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the homo-g-linolenic acid moiety is derived from fish oils, liver and kidney. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C37H66O5 None None None 38615.9 15343.9 29803.6 41202.5 32323.6 14021.1 47468.9 38545.4 30757.5 18434.4 33136.6 21850.5 116014.0 48032.9 20602.4 10980.6 17780.2 160648.0 25415.9 42491.8 18207.2 21717.2 28477.0 52031.1 45566.3 25764.9 23002.4 46461.8 23265.3 19278.8 27950.8 14366.4 45484.2 21071.5 12025.1 49171.6 38174.5 26417.8 43981.3 30748.6 93734.6 66770.1 611.1442406_MZ Oxidized glutathione Un 1.0 None None None None Oxidized glutathione is a glutathione dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized. glutathione participates in leukotriene synthesis and is a cofactor for the enzyme glutathione peroxidase. It is also important as a hydrophilic molecule that is added to lipophilic toxins and waste in the liver during biotransformation before they can become part of the bile. glutathione is also needed for the detoxification of methylglyoxal, a toxin produced as a by-product of metabolism. This detoxification reaction is carried out by the glyoxalase system. Glyoxalase I (EC 4.4.1.5) catalyzes the conversion of methylglyoxal and reduced glutathione to S-D-Lactoyl-glutathione. Glyoxalase II (EC 3.1.2.6) catalyzes the hydrolysis of S-D-Lactoyl-glutathione to glutathione and D-lactate. C20H32N6O12S2 None None None 3219600.0 3432220.0 3726190.0 1517960.0 1787410.0 2801100.0 2035630.0 2933870.0 2274710.0 1834540.0 2356200.0 3579540.0 1021020.0 3486880.0 2007880.0 1338480.0 2111480.0 1601280.0 1969240.0 1583340.0 3040590.0 3640430.0 1616470.0 3318880.0 1734090.0 3277660.0 2301100.0 2444950.0 3661060.0 3030790.0 2745840.0 1547120.0 3436340.0 2164720.0 4178360.0 2483880.0 3382370.0 3457000.0 2095190.0 1885670.0 1649440.0 2006520.0 613.5201962_MZ Diglyceride with formula C37H70O5 Un 1.0 None None None None DG(16:0/18:1(11Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(16:0/18:1(11Z)/0:0), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of vaccenic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the vaccenic acid moiety is derived from butter fat and animal fat. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C37H70O5 None None None 321288.0 68376.8 149815.0 108307.0 264525.0 84168.7 358232.0 369850.0 118641.0 103610.0 178336.0 155996.0 698873.0 313730.0 112180.0 53768.2 43750.3 1539980.0 91799.4 390480.0 143347.0 100500.0 102218.0 613048.0 290474.0 154885.0 116570.0 350257.0 119482.0 85012.0 152850.0 76782.9 320841.0 90404.6 52585.1 277963.0 234178.0 117917.0 339657.0 122844.0 554305.0 505060.0 618.5815014_MZ Ceramide with formula C40H77NO3 Un 1.0 None None None None Ceramides (N-acylsphingosine) are one of the hydrolysis byproducts of sphingomyelin by the enzyme sphingomyelinase (sphingomyelin phosphorylcholine phosphohydrolase E.C.3.1.4.12) which has been identified in the subcellular fractions of human epidermis (PMID 25935) and many other tissues. They can also be synthesized from serine and palmitate in a de novo pathway and are regarded as important cellular signals for inducing apoptosis (PMID 14998372). Is key in the biosynthesis of glycosphingolipids and gangliosides. C40H77NO3 None None None 56362.7 62802.5 46537.3 39389.9 51062.6 29323.9 56801.9 44592.8 39145.5 26708.8 56302.1 55960.9 51733.7 50493.5 27979.7 40604.7 47482.5 95607.1 41155.4 57955.2 35311.9 19002.9 36746.9 62456.0 56647.3 39696.6 41050.7 62627.1 29636.9 44519.7 42829.3 24121.9 55957.6 44588.2 15924.8 36481.3 32207.2 40264.4 46175.4 28214.4 59954.9 36727.1 620.0176456_MZ ADP-ribose 1-2 cyclic phosphate Un 1.0 None None None None ADP-ribose 1-2 cyclic phosphate is a cyclic phosphate nucleotide that arises from tRNA processing. In eukaryotic cells, pre-tRNAs spliced by a pathway that produces a 3',5'-phosphodiester, 2'-phosphomonoester linkage contain a 2'-phosphate group adjacent to the tRNA anticodon. This 2'-phosphate is transferred to NAD to give adenosine diphosphate (ADP)-ribose 1, 2-cyclic phosphate (Appr>p), which is subsequently metabolized to ADP-ribose 1'-phosphate (Appr-1'p). The latter reaction is catalyzed by a cyclic phosphodiesterase (CPDase). (PMID: 9148938). One molecule of ADP-ribose 1,2-cyclic phosphate (Appr>p) is formed during each of the approximately 500 000 tRNA splicing events. C15H22N5O16P3 None None None 45060.6 56120.0 65250.3 45354.5 83233.7 55761.9 88087.4 64329.1 69672.3 50471.8 55135.9 62309.5 53926.0 48565.9 80974.2 58593.7 71549.2 44064.1 67032.9 59948.1 49247.1 55341.7 58669.7 43504.5 77695.7 58859.9 83297.7 48427.6 41471.2 47198.5 78166.2 47119.7 61662.7 56391.4 46935.2 41536.5 62923.7 67454.3 30873.4 49108.1 68267.3 51661.3 620.1766813_MZ 6-(N-Acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol Un 1.0 None None None None 6-(N-Acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol is a reactant or product of enzyme EC 2.4.1.198. 6-(N-Acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol is a reactant or product of enzyme EC 3.5.1.89. C21H36NO18P None None None 120.904 271.142 176.702 83.3727 160.418 490.407 118.894 34.621 142.281 190.468 268.041 49.6611 20.5467 362.072 375.699 161.7 197.115 307.08 143.835 115.968 410.857 178.592 277.429 308.191 137.772 142.274 436.603 92.494 231.966 288.297 134.282 142.207 258.463 274.575 400.93 273.816 221.508 224.95 263.954 1398.09 215.65 620.5973185_MZ Ceramide with formula C40H79NO3 Un 1.0 None None None None Ceramides (N-acylsphingosine) are one of the hydrolysis byproducts of sphingomyelin by the enzyme sphingomyelinase (sphingomyelin phosphorylcholine phosphohydrolase E.C.3.1.4.12) which has been identified in the subcellular fractions of human epidermis (PMID 25935) and many other tissues. They can also be synthesized from serine and palmitate in a de novo pathway and are regarded as important cellular signals for inducing apoptosis (PMID 14998372). Is key in the biosynthesis of glycosphingolipids and gangliosides. C40H79NO3 None None None 123839.0 197562.0 156312.0 120496.0 91188.4 94295.3 232067.0 96315.4 100332.0 59940.1 147065.0 281422.0 105080.0 91991.6 83169.0 91343.0 147588.0 235946.0 116563.0 180542.0 91965.4 41330.9 75613.7 179115.0 151841.0 101868.0 102651.0 183899.0 67886.3 125876.0 138722.0 73580.8 166785.0 135609.0 38706.2 66527.0 89783.4 146075.0 213946.0 62324.0 134634.0 76321.1 621.5453521_MZ Diglyceride with formula C39H74O5 Un 1.0 None None None None DG(14:0/22:1(13Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(14:0/22:1(13Z)/0:0), in particular, consists of one chain of myristic acid at the C-1 position and one chain of erucic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the erucic acid moiety is derived from seed oils and avocados. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C39H74O5 None None None 155.365 111.951 544.864 85.301 295.71 86.7927 258.7 926.513 161.761 320.435 520.295 184.587 189.939 237.905 950.916 112.297 115.178 802.911 146.911 71.0812 251.152 186.69 196.254 282.776 96.7098 122.719 440.122 786.41 138.244 147.701 52.4573 71.7889 10.909 383.144 306.124 295.877 741.221 86.0052 627.4368369_MZ Diglyceride with formula C39H60O5 Un 1.0 None None None None DG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/0:0), in particular, consists of two chains of stearidonic acid at the C-1 and C-2 positions. The stearidonic acid moieties are derived from seed oils. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C39H60O5 None None None 2382.15 2559.34 1120.52 2998.51 2118.71 4408.07 2760.8 1801.24 1454.99 2584.17 2886.9 2643.19 1694.51 2140.94 1602.84 7992.46 1796.01 723.365 1155.26 1070.74 1871.59 708.538 2919.38 1780.55 2469.31 1235.36 2791.19 1771.6 541.015 2969.41 4119.39 3398.49 1163.27 1269.06 849.608 1568.75 1144.44 2038.46 467.889 1620.38 1590.7 964.177 632.2037169_MZ 3'-Sialyllactose Un 1.0 None None None None Sialyllactose is an oligossaccharide found in both human breast milk and cow's milk. It is the predominant sialylated component in milk. Sialyllactose has recently been shown to inhibit the infection of HIV-1 virus. Sialyllactose is also responsible for the inhibitory activity of milk on cholera toxin. C23H39NO19, 6'-Sialyllactose None None None 8050.5 7270.38 9456.79 9280.99 6640.04 7363.82 9094.09 7826.14 7246.61 9422.43 6560.09 8785.37 5444.09 8906.77 8518.83 9448.25 10393.7 6976.98 9458.83 8435.51 9547.97 7091.59 7981.92 7930.27 11665.3 6398.93 11820.5 7456.2 8200.05 10229.6 8661.5 8505.87 6239.48 6905.88 9126.94 7982.78 6918.73 9041.59 4881.23 8927.64 8754.95 11902.0 633.4890182_MZ Diglyceride with formula C39H66O5 Un 1.0 None None None None DG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/0:0), in particular, consists of one chain of myristic acid at the C-1 position and one chain of docosapentaenoic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the docosapentaenoic acid moiety is derived from fish oils. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C39H66O5 None None None 11187.2 6732.53 7056.82 19664.2 8822.87 5248.59 12611.7 12068.6 11957.2 6828.16 9796.0 11712.3 17421.2 11943.5 5568.79 4987.84 11326.2 28149.5 7742.56 13234.3 4445.88 7958.88 11145.6 10866.3 10317.0 8372.16 7637.11 14111.5 7881.07 8566.11 8692.06 4952.6 11947.3 6903.8 4204.45 12818.3 8710.2 9336.05 7654.25 8897.55 15599.0 12511.2 634.6128081_MZ Ceramide (d18:1/23:0) Un 1.0 None None None None Cer(d18:1/23:0) is an sphingolipid identified in stratum corneum by reversed-phase high-performance liquid chromatography photospray ionization mass spectrometry. Tricosanamide has been found in human blood plasma by gas-liquid chromatography on high temperature polarizable capillary columns. Tricosanamide is a molecular species of lipid determined in human erythrocytes. (PMID: 2755317, 17027012, 8354950). C41H81NO3 None None None 31354.1 44868.6 25616.6 39263.0 31370.5 19086.8 65491.5 23902.8 46921.6 19521.6 36780.0 72538.0 33339.6 30671.2 28023.6 21973.4 74600.4 36785.0 29684.6 26956.2 29407.8 19661.9 28091.4 34296.8 37238.2 30503.3 41037.1 37636.6 12059.4 25025.5 31932.5 17576.2 40394.9 32195.2 10742.6 21012.7 28488.0 45621.3 20545.7 21934.5 24801.2 24586.1 635.5040304_MZ Diglyceride with formula C39H68O5 Un 1.0 None None None None DG(14:0/22:4(7Z,10Z,13Z,16Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(14:0/22:4(7Z,10Z,13Z,16Z)/0:0), in particular, consists of one chain of myristic acid at the C-1 position and one chain of adrenic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the adrenic acid moiety is derived from animal fats. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C39H68O5 None None None 65740.7 47361.4 49391.2 79768.6 56988.3 38096.2 84552.6 80743.0 62898.7 45597.3 67742.5 68600.1 98324.9 79562.7 33041.2 29492.6 65739.8 203177.0 45318.9 93784.1 37903.8 35623.4 71997.0 64234.9 61013.6 42252.7 42578.2 105076.0 45838.9 55147.4 56435.4 29514.6 71630.1 40945.9 24002.5 81454.7 58365.7 69041.3 58697.4 56453.5 82500.2 83303.1 637.5196338_MZ Diglyceride with formula C39H70O5 Un 1.0 None None None None DG(20:3(5Z,8Z,11Z)/16:0/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(20:3(5Z,8Z,11Z)/16:0/0:0), in particular, consists of one chain of mead acid at the C-1 position and one chain of palmitic acid at the C-2 position. The mead acid moiety is derived from fish oils, liver and kidney, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C39H70O5 None None None 86696.3 47428.6 67128.0 86508.8 91567.1 52435.5 125845.0 132533.0 83996.8 57821.9 81886.5 102916.0 195550.0 180884.0 54080.6 32619.9 51676.6 252932.0 59372.5 114602.0 61057.3 64947.7 89762.4 106313.0 100353.0 79181.4 57640.6 133293.0 69671.5 54426.2 83001.1 33171.2 171286.0 59774.2 29796.3 136857.0 116299.0 77580.0 102458.0 71693.4 154525.0 164345.0 639.5358047_MZ Diglyceride with formula C39H72O5 Un 1.0 None None None None DG(18:1(9Z)/18:1(11Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(18:1(9Z)/18:1(11Z)/0:0), in particular, consists of one chain of oleic acid at the C-1 position and one chain of vaccenic acid at the C-2 position. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the vaccenic acid moiety is derived from butter fat and animal fat. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C39H72O5 None None None 131409.0 32104.5 63578.1 46823.1 143189.0 50988.5 146935.0 185322.0 72920.5 59156.3 90160.9 84686.5 313654.0 247338.0 65120.3 27202.2 23516.6 390181.0 46315.2 225328.0 72908.6 85816.3 65750.5 161267.0 121248.0 112263.0 55942.4 135294.0 82416.0 41792.0 68541.0 33248.7 254822.0 56271.6 33788.0 161395.0 146592.0 60218.4 117964.0 68027.0 206069.0 263284.0 642.3069183_MZ S-(11-hydroxy-9-deoxy-delta12-PGD2)-glutathione Un 1.0 None None None None S-(11-hydroxy-9-deoxy-delta12-PGD2)-glutathione is the glutathione conjugate of S-(11-hydroxy-9-deoxy-delta12-PGD2). C30H49N3O10S, S-(9-hydroxy-PGA1)-glutathione None None None 5027.45 4485.0 5148.85 5820.52 6000.72 6119.57 5135.95 4373.44 5436.91 5524.74 5766.6 5165.99 4698.38 6090.42 5115.81 5487.33 5758.56 5889.45 5249.24 5310.89 4536.52 4751.73 5294.7 4481.72 5881.72 4905.21 6064.61 5502.77 4839.09 5739.47 5509.63 5766.51 5441.56 4297.69 4432.2 5023.7 4281.93 4846.46 3486.97 5517.15 5286.63 5046.23 643.5610061_MZ Diglyceride with formula C39H76O5 Un 1.0 None None None None DG(16:0/20:0/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(16:0/20:0/0:0), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of arachidic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the arachidic acid moiety is derived from peanut oil. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C39H76O5 None None None 4274.85 7034.63 3123.81 5608.09 2794.1 4138.38 8030.38 2467.95 3128.04 2913.78 4146.73 5556.15 4751.79 4685.19 3081.29 10520.4 3473.15 8222.51 3954.9 6243.11 2607.91 1475.8 3646.68 5449.96 4823.11 2314.43 4185.54 6285.76 1966.06 4724.71 5651.12 7814.62 3888.11 3698.21 1303.8 2963.21 2264.57 3835.48 4094.23 2154.4 5258.75 3248.15 644.4999550_MZ CerP(d18:1/18:0) Un 1.0 None None None None C36H72NO6P None None None 1582.45 1440.56 2015.87 2958.87 2595.59 2219.23 2347.46 1456.6 1491.67 2267.08 2846.38 3074.68 1069.47 2873.49 1725.84 1835.5 974.352 1902.5 1558.84 1997.68 1443.84 1347.35 2221.09 1555.11 2071.09 1575.11 2467.88 2127.39 1070.12 1656.91 1634.5 1792.26 2152.28 1189.57 935.84 1287.9 1667.38 2138.47 1530.88 1671.66 1108.44 1523.83 645.5614186_MZ Cholesterol ester (18:3(9Z_12Z_15Z)) Un 1.0 None None None None CE(18:3(9Z,12Z,15Z)) is a cholesterol fatty acid ester or simply a cholesterol ester (CE). Cholesterol esters are cholesterol molecules with long-chain fatty acids linked to the hydroxyl group. They are much less polar than free cholesterol and appear to be the preferred form for transport in plasma and for storage. Cholesterol esters do not contribute to membranes but are packed into intracellular lipid particles or lipoprotein particles. Because of the mechanism of synthesis, plasma cholesterol esters tend to contain relatively high proportions of C18 fatty acids. Cholesterol esters are major constituents of the adrenal glands and they also accumulate in the fatty lesions of atherosclerotic plaques. Cholesterol esters are also major constituents of the lipoprotein particles carried in blood (HDL, LDL, VLDL). The cholesterol esters in high-density lipoproteins (HDL) are synthesized largely by transfer of fatty acids to cholesterol from position sn-2 (or C-2) of phosphatidylcholine catalyzed by the enzyme lecithin cholesterol acyl transferase (LCAT). The enzyme also promotes the transfer of cholesterol from cells to HDL. As cholesterol esters accumulate in the lipoprotein core, cholesterol is removed from its surface thus promoting the flow of cholesterol from cell membranes into HDL. This in turn leads to morphological changes in HDL, which grow and become spherical. Subsequently, cholesterol esters are transferred to the other lipoprotein fractions LDL and VLDL, a reaction catalyzed by cholesteryl ester transfer protein. Another enzyme, acyl-CoA:cholesterol acyltransferase (ACAT) synthesizes cholesterol esters from CoA esters of fatty acids and cholesterol. Cholesterol ester hydrolases liberate cholesterol and free fatty acids when required for membrane and lipoprotein formation, and they also provide cholesterol for hormone synthesis in adrenal cells. C45H74O2 None None None 874.863 1915.57 413.55 1307.57 283.142 738.822 1832.0 150.095 471.569 412.494 766.912 1125.86 457.449 1035.81 761.083 4144.18 795.356 1572.53 670.328 912.263 332.328 122.465 578.676 1018.54 982.816 264.762 988.983 1419.41 190.996 942.7 1305.2 2318.87 552.576 789.219 208.087 492.223 350.91 803.837 434.806 239.075 1205.48 409.197 646.4941097_MZ Phosphatidylethanolamine (14:0/P-16:0) Un 1.0 None None None None PE(14:0/P-16:0) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(14:0/P-16:0), in particular, consists of one chain of myristic acid at the C-1 position and one chain of plasmalogen 16:0 at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the plasmalogen 16:0 moiety is derived from animal fats, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. C35H70NO7P None None None 572.021 231.861 282.849 464.091 541.447 227.261 511.393 720.232 323.986 397.554 315.693 280.623 451.606 304.621 325.638 829.868 228.322 1042.4 228.335 557.802 228.964 274.019 212.207 811.845 323.312 535.432 522.304 528.849 176.144 215.406 687.526 813.917 353.522 201.504 200.372 249.477 183.006 433.082 273.29 253.691 451.77 612.07 646.6129319_MZ Ceramide with formula C42H81NO3 Un 1.0 None None None None Ceramides (N-acylsphingosine) are one of the hydrolysis byproducts of sphingomyelin by the enzyme sphingomyelinase (sphingomyelin phosphorylcholine phosphohydrolase E.C.3.1.4.12) which has been identified in the subcellular fractions of human epidermis (PMID 25935) and many other tissues. They can also be synthesized from serine and palmitate in a de novo pathway and are regarded as important cellular signals for inducing apoptosis (PMID 14998372). Is key in the biosynthesis of glycosphingolipids and gangliosides. C42H81NO3 None None None 169243.0 141925.0 118273.0 173829.0 212560.0 70364.5 239999.0 213931.0 190874.0 103055.0 219391.0 162791.0 220621.0 224356.0 107086.0 77217.5 301565.0 255267.0 114909.0 127207.0 131258.0 84360.6 120681.0 144758.0 158078.0 179367.0 145183.0 153457.0 60086.6 100526.0 122547.0 62791.5 223667.0 106845.0 60571.9 110220.0 171442.0 164683.0 110114.0 110166.0 175476.0 172699.0 647.5795550_MZ Cholesterol Ester (18:2(9Z,12Z)) Un 1.0 None None None None Cholesteryl linoleic acid is a cholesteryl ester. A cholesteryl ester is an ester of cholesterol. Fatty acid esters of cholesterol constitute about two-thirds of the cholesterol in the plasma. Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. The accumulation of cholesterol esters in the arterial intima (the innermost layer of an artery, in direct contact with the flowing blood) is a characteristic feature of atherosclerosis. Atherosclerosis is a disease affecting arterial blood vessels. It is a chronic inflammatory response in the walls of arteries, in large part to the deposition of lipoproteins (plasma proteins that carry cholesterol and triglycerides). Cholesteryl linoleate is contained in low density lipoprotein and atherosclerotic lesions. The oxidation products of cholesteryl linoleate may cause chronic inflammatory processes. (PMID 9684755, 11950694). C45H76O2 None None None 177.293 1082.28 2962.53 812.84 287.377 40.2043 373.505 133.51 453.236 109.633 137.735 1520.89 83.4381 51.6177 72.1076 2781.27 10.4779 1490.3 135.455 649.5090654_MZ Sphingomyelin with formula C35H75N2O6P Un 1.0 None None None None Sphingomyelin (d18:0/12:0) or SM(d18:0/12:0) is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons. It usually consists of phosphorylcholine and ceramide. In humans, sphingomyelin is the only membrane phospholipid not derived from glycerol. Like all sphingolipids, SPH has a ceramide core (sphingosine bonded to a fatty acid via an amide linkage). In addition it contains one polar head group, which is either phosphocholine or phosphoethanolamine. The plasma membrane of cells is highly enriched in sphingomyelin and is considered largely to be found in the exoplasmic leaflet of the cell membrane. However, there is some evidence that there may also be a sphingomyelin pool in the inner leaflet of the membrane. Moreover, neutral sphingomyelinase-2 - an enzyme that breaks down sphingomyelin into ceramide has been found to localise exclusively to the inner leaflet further suggesting that there may be sphingomyelin present there. Sphingomyelin can accumulate in a rare hereditary disease called Niemann-Pick Disease, types A and B. Niemann-Pick disease is a genetically-inherited disease caused by a deficiency in the enzyme Sphingomyelinase, which causes the accumulation of Sphingomyelin in spleen, liver, lungs, bone marrow, and the brain, causing irreversible neurological damage. SMs play a role in signal transduction. Sphingomyelins are synthesized by the transfer of phosphorylcholine from phosphatidylcholine to a ceramide in a reaction catalyzed by sphingomyelin synthase. C35H75N2O6P None None None 771.213 689.399 907.865 1538.89 1773.21 1015.13 1014.46 978.481 1045.42 869.347 1352.54 1080.8 752.184 1687.92 883.301 781.236 516.301 1137.23 572.451 806.703 399.17 493.448 1069.44 836.921 859.673 763.572 1110.5 911.941 489.772 551.974 560.993 706.719 1605.84 367.117 606.945 809.084 909.615 1150.57 385.358 716.874 2031.97 879.113 650.4304299_MZ Phosphatidylethanolamine (14:1(9Z)/14:1(9Z)) Un 1.0 None None None None PE(14:1(9Z)/14:1(9Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(14:1(9Z)/14:1(9Z)), in particular, consists of two chains of myristoleic acid at the C-1 and C-2 positions. The myristoleic acid moieties are derived from milk fats. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. C33H62NO8P None None None 744.767 840.947 841.034 836.538 1452.98 1696.13 429.235 384.784 413.762 789.754 1118.94 1047.96 93.2993 1292.54 1880.47 1037.99 192.544 79.3652 352.641 1058.97 1383.02 1014.73 702.661 712.952 784.279 698.38 1663.63 591.215 701.466 852.836 831.6 1085.9 737.225 678.704 1040.78 232.729 431.21 1007.05 295.643 904.473 1233.96 133.596 651.2213264_MZ 3'-Sialyllactosamine Un 1.0 None None None None

3'-Sialyllactosamine is an oligosaccharide found in human milk. Oligosaccharides in human milk inhibit enteric pathogens in vitro and in vivo. (PMID:10683228)

.

Helicobacter pylori-induced activation of neutrophils occurs by lectinophagocytosis, the recognition of sialylated glycoconjugates (3'-sialyllactosamine was the most efficient inhibitor) on the neutrophil cell surface by a bacterial adhesin leads to phagocytosis and an oxidative burst with the production of reactive oxygen metabolites. (PMID: 11087709)

. C23H40N2O18 None None None 1615.67 1945.26 3008.26 1653.8 1979.75 2087.89 2250.88 1806.97 2043.64 1976.99 1551.09 2429.62 1324.61 2133.0 2490.83 1190.67 3274.47 1640.45 2713.38 2176.6 2775.39 2457.01 1846.12 2058.28 2686.26 1955.7 3403.17 1974.59 3210.73 3085.67 1723.98 1130.65 1912.69 1649.05 3504.1 2084.81 2094.35 2204.17 1386.18 2534.83 2342.76 3326.64 655.5641390_MZ Diglyceride (15:0/22:1(13Z)/0:0) Un 1.0 None None None None DG(15:0/22:1(13Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(15:0/22:1(13Z)/0:0), in particular, consists of one chain of pentadecanoic acid at the C-1 position and one chain of erucic acid at the C-2 position. The pentadecanoic acid moiety is derived from dairy products and milk fat, while the erucic acid moiety is derived from seed oils and avocados. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C40H76O5 None None None 17953.6 21604.6 12917.0 22557.5 20227.4 19800.1 21376.5 13096.6 11319.8 14529.8 17421.1 15174.1 17219.5 19567.8 9958.84 41624.3 11462.0 28550.5 13622.8 15889.8 10631.5 5288.92 13691.5 17124.9 16489.4 12153.2 13365.6 20886.5 9879.19 17486.7 21651.9 30338.7 13493.3 13276.6 11736.5 14977.4 7779.4 11123.0 12488.9 8942.19 20767.3 12323.2 657.4984714_MZ Diglyceride (16:1(9Z)/22:6(4Z_7Z_10Z_13Z_16Z_19Z)/0:0) Un 1.0 None None None None DG(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0), in particular, consists of one chain of palmitoleic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The palmitoleic acid moiety is derived from animal fats and vegetable oils, while the docosahexaenoic acid moiety is derived from fish oils. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C41H66O5 None None None 17766.7 6636.09 8630.36 13590.8 21923.9 10417.0 22997.9 22700.4 9881.81 13004.6 14128.5 7682.35 45771.8 31735.1 8337.49 10401.1 6874.09 55715.6 8830.73 20457.7 9111.56 8218.79 12055.6 17808.0 15922.8 12369.1 10269.4 20212.1 10460.1 9426.33 13938.6 14890.9 18948.5 7654.83 7897.35 22442.1 12458.3 7865.37 13990.7 11662.0 33939.5 30706.8 659.5046020_MZ Diglyceride (16:0/22:6(4Z_7Z_10Z_13Z_16Z_19Z)/0:0) Un 1.0 None None None None DG(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the docosahexaenoic acid moiety is derived from fish oils. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C41H68O5 None None None 128394.0 31162.4 46940.4 40414.0 78505.6 37361.0 111823.0 203024.0 44678.3 45141.1 68459.5 35963.1 239801.0 80606.2 28803.6 27906.2 36873.0 662307.0 32010.4 117561.0 37769.4 24686.3 52105.9 146291.0 55983.0 37511.6 30624.8 157957.0 49599.1 46327.7 50822.9 34232.5 83972.2 32497.3 20924.8 89919.8 57121.7 51027.5 102975.0 73492.2 164899.0 161377.0 660.2985369_MZ S-(11-OH-9-deoxy-delta9_12-PGD2)-glutathione Un 1.0 None None None None C30H47N3O10S None None None 6637.2 4910.23 5578.32 4600.59 6596.45 4822.31 7638.04 5776.5 5198.12 5211.37 6716.14 5669.88 3912.29 5962.43 5295.47 4415.6 6341.83 4797.85 4456.5 5446.67 5412.34 4666.11 5520.2 5558.77 5730.62 5324.87 5231.97 5867.28 4543.01 5356.68 6058.42 4478.96 6349.18 4535.82 3377.28 5250.29 4047.64 4606.18 3175.88 5184.58 5441.34 6518.69 661.5175643_MZ Phosphatidic Acid with formula C37H75O7P Un 1.0 None None None None 2-octadecanoyl-1-hexadecyl-sn-glycero-3-phosphate is an intermediate in ether lipid metabolism. 2-octadecanoyl-1-hexadecyl-sn-glycero-3-phosphate is converted from 1-octadecyl-glycerone-3-phosphate via 1-acylglycerol-3-phosphate O-acyltransferase. (EC: 2.3.1.51). Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. Ether lipids are called plasmalogens (1-O-1'-alkenyl-2-acylglycerophospholipids) if these are glycerol-containing phospholipids with an unsaturated O-(1-alkenyl) (vinyl ether) group at the first position on the glycerol chain. Plasmalogens as well as some 1-O-alkyl lipids are ubiquitous and sometimes major parts of the cell membranes in mammals and anaerobic bacteria. In archaea, ether lipids are the major polar lipids in the cell envelope and their abundance is one of the major characteristics that separate this group of prokaryotes from the bacteria. In these cells, diphytanylglycerolipids or bipolar macrocyclic tetraethers can form covalently linked bilayers. C37H75O7P None None None 39371.3 14236.9 23134.7 17607.5 30369.2 19278.1 41618.4 58354.9 24165.0 18606.1 24984.0 21862.7 61444.5 38408.9 14419.7 11974.6 16025.4 140142.0 16442.9 56428.9 17658.2 15399.3 23316.2 44058.7 25091.6 21539.3 14368.2 48588.6 20902.9 17944.8 19779.1 13607.4 44869.8 14445.2 10353.7 37549.5 27360.7 24924.0 36212.0 28257.1 46875.7 57304.8 662.9716431_MZ Phosphatidylinositol-3_4_5-trisphosphate Un 1.0 None None None None C12H24O22P4 None None None 9218.21 9017.7 8257.26 9711.95 9655.28 9591.27 9929.14 8982.66 8274.9 8993.12 9353.04 9504.87 10202.6 8944.46 9286.06 12992.2 8869.63 9220.35 8563.03 8936.28 8575.45 8453.16 8974.61 8850.79 8709.24 8242.02 8483.34 8791.0 8219.68 9286.57 10299.5 10695.3 8218.93 8497.03 8910.13 8885.21 7728.32 8670.41 7659.77 8988.78 12751.1 8864.63 665.2139302_MZ Glycogen Un 1.0 None None None None Glycogen is a highly-branched polymer of about 30,000 glucose residues and has a molecular weight between 106 and 107 daltons (4.8 million approx.). Most of Glc units are linked by alpha-1,4 glycosidic bonds, approximately 1 in 12 Glc residues also makes -1,6 glycosidic bond with a second Glc which results in the creation of a branch. Glycogen only has one reducing end and a large number of non-reducing ends with a free hydroxyl group at carbon 4. The glycogen granules contain both glycogen and the enzymes of glycogen synthesis (glycogenesis) and degradation (glycogenolysis). The enzymes are nested between the outer branches of the glycogen molecules and act on the non-reducing ends. Therefore, the many non-reducing end-branches of glycogen facilitate its rapid synthesis and breakdown. In hypoglycemia caused by excessive insulin, liver glycogen levels are high, but the high insulin level prevents the glycogenolysis necessary to maintain normal blood sugar levels. Glucagon is a common treatment for this type of hypoglycemia. Glycogen is a polysaccharide that is the principal storage form of glucose (Glc) in animal and human cells. Glycogen is found in the form of granules in the cytosol in many cell types. Hepatocytes (liver cells) have the highest concentration of it - up to 8% of the fresh weight in well fed state, or 100 to 120 g in an adult - giving liver a distinctive, 'starchy taste'. In the muscles, glycogen is found in a much lower concentration (1% of the muscle mass), but the total amount exceeds that in liver. Small amounts of glycogen are found in the kidneys, and even smaller amounts in certain glial cells in the brain and white blood cells. C24H42O21, Maltotetraose, Stachyose None None None 65061.1 91626.7 108398.0 25506.1 36687.3 83593.8 52242.5 33276.4 83667.8 104178.0 78991.0 77545.8 76858.5 74242.6 96099.5 90361.9 27930.7 55520.5 155567.0 63993.9 93843.0 125018.0 78514.5 77661.4 47603.5 64522.6 135321.0 96679.7 175986.0 140364.0 108465.0 48386.4 65517.1 72120.9 110113.0 144787.0 80283.0 105761.0 45019.7 124274.0 79294.0 85120.0 665.5490548_MZ Diglyceride (16:1(9Z)/22:2(13Z,16Z)/0:0) Un 1.0 None None None None DG(16:1(9Z)/22:2(13Z,16Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(16:1(9Z)/22:2(13Z,16Z)/0:0), in particular, consists of one chain of palmitoleic acid at the C-1 position and one chain of docosadienoic acid at the C-2 position. The palmitoleic acid moiety is derived from animal fats and vegetable oils, while the docosadienoic acid moiety is derived from animal fats. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C41H74O5 None None None 10650.1 5488.1 6253.78 4114.01 9420.79 5058.48 10835.1 15817.4 6256.61 4830.94 7000.01 6481.83 16945.6 20866.8 4004.22 3699.42 4121.27 26606.5 4105.45 12709.6 5500.58 5453.51 6384.02 11380.2 9242.61 6620.75 5019.81 12727.3 6293.43 5126.19 6517.57 3602.59 16707.1 4840.24 3010.93 10476.1 10694.8 6236.08 9719.14 6031.35 12861.9 14903.1 665.6059869_MZ Diglyceride (15:0/24:0/0:0) Un 1.0 None None None None DG(15:0/24:0/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(15:0/24:0/0:0), in particular, consists of one chain of pentadecanoic acid at the C-1 position and one chain of lignoceric acid at the C-2 position. The pentadecanoic acid moiety is derived from dairy products and milk fat, while the lignoceric acid moiety is derived from groundnut oil. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C42H82O5 None None None 2550.46 3104.05 1965.49 2412.21 4146.41 768.349 3172.57 3466.91 3368.83 2064.74 3365.13 1984.76 3505.06 4105.38 1914.32 983.845 5323.13 4494.4 2132.87 2277.95 2047.56 2058.64 2614.29 2758.83 3444.97 2485.59 4384.08 3402.18 1557.02 1786.09 1401.23 2409.43 4043.43 2226.04 2704.39 2207.74 2992.15 5096.32 2041.97 2027.57 3040.85 2416.24 668.6337057_MZ N-Lignoceroylsphingosine Un 1.0 None None None None Ceramide (N-acyl sphingosine) is known as an important precursor common to the biosynthesis of glycosphingolipids and sphingomyelin. Naturally occurring ceramide is composed of various molecular species resulting from a combination of C16 and 26 fatty acids and sphingosine (sphingenine). The N-acyl chain is thought to be mainly introduced by the acylation of sphinganine, and the resultant dihydroceramide (N-acyl sphinganine) is desaturated to form ceramide. The hydrolysis of sphingolipids also yields ceramide and may further lead to the generation of sphingosine and sphingosine phosphate. Recent studies have established the existence of a sphingomyelin cycle or a sphingomyelin pathway that operates in response to various agonists and stresses. Ceramide, is thought to act as a second messenger in the intracellular signaling pathway to apoptosis, cell cycle arrest, cell differentiation, cell propagation, or induction of cytokine synthesis. C42H83NO3, Ceramide (d18:1/24:0), Ceramide (d18:0/24:1(15Z)) None None None 14703.6 23899.5 14490.7 20000.1 16416.7 11520.0 27661.8 14747.2 19636.6 11041.4 19951.8 33761.5 14774.3 15483.7 10801.8 8665.71 33994.1 19593.4 14507.8 12383.7 15422.5 9812.48 12424.6 16559.5 19029.6 16208.6 17245.5 18838.5 7195.3 14658.5 16056.9 9072.58 19622.4 14320.1 8331.86 9990.61 18554.0 23335.8 16092.9 10527.6 14885.5 11463.2 669.5768775_MZ Diglyceride (14:0/24:1(15Z)/0:0) Un 1.0 None None None None DG(14:0/24:1(15Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(14:0/24:1(15Z)/0:0), in particular, consists of one chain of myristic acid at the C-1 position and one chain of nervonic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the nervonic acid moiety is derived from fish oils. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C41H78O5 None None None 7839.28 9781.45 4081.49 11833.0 8131.2 6465.26 10603.3 5052.62 7511.72 6492.13 7966.72 6712.11 8394.28 11330.7 5576.15 14337.5 8613.13 11903.8 6022.03 7787.41 5695.28 3788.01 8096.94 8491.22 8691.94 4998.75 8640.16 9199.31 3262.17 6364.12 10149.9 13442.7 6146.77 5213.99 3275.23 6628.49 5569.09 5455.34 4617.16 5271.49 9168.21 6666.49 671.6156508_MZ Cholesterol Ester with formula Un 1.0 None None None None CE(18:0) is a cholesterol fatty acid ester or simply a cholesterol ester (CE). Cholesterol esters are cholesterol molecules with long-chain fatty acids linked to the hydroxyl group. They are much less polar than free cholesterol and appear to be the preferred form for transport in plasma and for storage. Cholesterol esters do not contribute to membranes but are packed into intracellular lipid particles or lipoprotein particles. Because of the mechanism of synthesis, plasma cholesterol esters tend to contain relatively high proportions of C18 fatty acids. Cholesterol esters are major constituents of the adrenal glands and they also accumulate in the fatty lesions of atherosclerotic plaques. Cholesterol esters are also major constituents of the lipoprotein particles carried in blood (HDL, LDL, VLDL). The cholesterol esters in high-density lipoproteins (HDL) are synthesized largely by transfer of fatty acids to cholesterol from position sn-2 (or C-2) of phosphatidylcholine catalyzed by the enzyme lecithin cholesterol acyl transferase (LCAT). The enzyme also promotes the transfer of cholesterol from cells to HDL. As cholesterol esters accumulate in the lipoprotein core, cholesterol is removed from its surface thus promoting the flow of cholesterol from cell membranes into HDL. This in turn leads to morphological changes in HDL, which grow and become spherical. Subsequently, cholesterol esters are transferred to the other lipoprotein fractions LDL and VLDL, a reaction catalyzed by cholesteryl ester transfer protein. Another enzyme, acyl-CoA:cholesterol acyltransferase (ACAT) synthesizes cholesterol esters from CoA esters of fatty acids and cholesterol. Cholesterol ester hydrolases liberate cholesterol and free fatty acids when required for membrane and lipoprotein formation, and they also provide cholesterol for hormone synthesis in adrenal cells. C45H80O2 None None None 1363.73 2844.2 734.535 3862.07 1425.99 1575.64 3745.21 930.93 1740.57 1232.59 1609.5 3238.79 1892.35 1563.82 1258.95 7480.35 2832.94 1418.78 1227.21 985.607 1427.4 468.939 1185.45 1658.29 1633.9 1236.07 3625.81 1995.1 220.142 1218.83 3400.33 6803.64 1251.99 2361.7 843.331 845.856 994.356 3611.27 800.508 826.113 1355.26 860.452 672.4944577_MZ Phosphatidylethanolamine (14:0/P-18:1(11Z)) Un 1.0 None None None None C37H72NO7P None None None 2303.24 2252.29 2114.52 2993.31 2295.77 2099.71 3191.1 2861.66 2469.69 1943.48 3361.7 3170.75 2528.89 2870.78 1636.22 2187.36 2435.44 3917.18 1739.26 2731.61 2350.72 1651.12 2849.65 2139.92 2554.45 1961.19 1927.44 3299.18 1717.25 2302.45 3501.9 3197.0 2244.55 1976.7 1534.85 2259.76 2234.84 1946.79 1584.38 1818.29 3190.37 2452.87 672.5451634_MZ Ceramide Phosphated with formula C38H76NO6P Un 1.0 None None None None CerP(d18:1/20:0) is a ceramide 1-phosphate belonging to the sphingolipid class of molecules. Ceramides are amides of fatty acids with long-chain di- or trihydroxy bases, the commonest in animals being sphingosine and in plants phytosphingosine. The acyl group of ceramides is generally a long-chain saturated or monounsaturated fatty acid. The most frequent fatty acids found in animal ceramides are 18:0, 24:0 and 24:1(n-9). Ceramide 1-phosphates are produced by phosphorylation of ceramide by a specific ceramide kinase. Ceramide-1-phosphate was shown to be a specific and potent inducer of arachidonic acid and prostanoid synthesis in cells through the translocation and activation of the cytoplasmic phospholipase A2. C38H76NO6P None None None 256.617 232.392 248.084 483.345 418.195 1796.31 482.934 303.547 104.565 78.6787 195.412 280.64 165.539 276.333 885.771 595.253 300.356 693.712 351.632 199.343 113.992 140.422 207.115 268.604 270.4 891.924 328.457 64.6634 353.94 1801.71 542.526 140.405 323.935 164.729 447.955 173.648 17.898 99.0938 138.055 673.4789204_MZ Phosphatidic acid (16:0/18:1(11Z)) Un 1.0 None None None None PA(16:0/18:1(11Z)) is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(16:0/18:1(11Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of vaccenic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the vaccenic acid moiety is derived from butter fat and animal fat. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. Indeed, the concentration of phosphatidic acids is often over-estimated in tissues and biofluids as it can arise by inadvertent enzymatic hydrolysis during inappropriate storage or extraction conditions during analysis. The main biosynthetic route of phosphatidic acid in animal tissues involves sequential acylation of alpha-glycerophosphate by acyl-CoA derivatives of fatty acids. PAs are biologically active lipids that can stimulate a large range of responses in many different cell types, such as platelet aggregation, smooth muscle contraction, in vivo vasoactive effects, chemotaxis, expression of adhesion molecules, increased tight junction permeability of endothelial cells, induction of stress fibres, modulation of cardiac contractility, and many others. Diacylglycerols (DAGs) can be converted to PAs by DAG kinases and indirect evidence supports the notion that PAs alter the excitability of neurons. Phospholipase Ds (PLDs), which catalyze the conversion of glycerolphospholipids, particularly phosphatidylcholine, to PAs and the conversion of N-arachidonoyl-phosphatidylethanolamine (NAPE) to anandamide and PAs are activated by several inflammatory mediators including bradykinin, ATP and glutamate. PAs activate downstream signaling pathways such as PKCs and mitogen-activated protein kinases (MAPKs), which are linked to an increase in sensitivity of sensory neurons either during inflammation or in chronic pain models. Circumstantial evidence that PAs are converted to DAGs. (PMID: 12618218, 16185776). C37H71O8P None None None 28825.4 20999.6 20221.7 26996.3 25940.0 19597.5 35250.9 35558.9 22199.4 18223.4 29535.5 31847.8 38344.7 29134.0 18989.3 18277.9 20483.8 47755.5 16525.4 31960.2 22853.6 14694.0 21398.8 26161.8 23502.5 26776.6 21392.1 30195.2 15907.5 20514.4 30171.0 27317.3 23319.0 16981.8 12328.6 21385.6 21710.7 17592.9 17015.2 19014.2 30605.3 33604.4 673.5901449_MZ Cholesterol ester (20:3(5Z,8Z,11Z)) Un 1.0 None None None None CE(20:3(5Z,8Z,11Z)) is a cholesterol fatty acid ester or simply a cholesterol ester (CE). Cholesterol esters are cholesterol molecules with long-chain fatty acids linked to the hydroxyl group. They are much less polar than free cholesterol and appear to be the preferred form for transport in plasma and for storage. Cholesterol esters do not contribute to membranes but are packed into intracellular lipid particles or lipoprotein particles. Because of the mechanism of synthesis, plasma cholesterol esters tend to contain relatively high proportions of C18 fatty acids. Cholesterol esters are major constituents of the adrenal glands and they also accumulate in the fatty lesions of atherosclerotic plaques. Cholesterol esters are also major constituents of the lipoprotein particles carried in blood (HDL, LDL, VLDL). The cholesterol esters in high-density lipoproteins (HDL) are synthesized largely by transfer of fatty acids to cholesterol from position sn-2 (or C-2) of phosphatidylcholine catalyzed by the enzyme lecithin cholesterol acyl transferase (LCAT). The enzyme also promotes the transfer of cholesterol from cells to HDL. As cholesterol esters accumulate in the lipoprotein core, cholesterol is removed from its surface thus promoting the flow of cholesterol from cell membranes into HDL. This in turn leads to morphological changes in HDL, which grow and become spherical. Subsequently, cholesterol esters are transferred to the other lipoprotein fractions LDL and VLDL, a reaction catalyzed by cholesteryl ester transfer protein. Another enzyme, acyl-CoA:cholesterol acyltransferase (ACAT) synthesizes cholesterol esters from CoA esters of fatty acids and cholesterol. Cholesterol ester hydrolases liberate cholesterol and free fatty acids when required for membrane and lipoprotein formation, and they also provide cholesterol for hormone synthesis in adrenal cells. C47H78O2 None None None 2827.72 5407.99 1499.95 6949.51 3028.52 3912.31 7038.64 1662.82 4194.45 2753.65 3211.32 6431.49 3784.97 3166.85 3153.05 8052.13 5387.39 3241.63 2735.44 2066.76 2861.34 1538.84 3154.62 3159.06 3498.32 2609.1 3801.03 3852.72 869.922 2812.69 6305.66 9152.97 2534.43 2837.58 2067.84 1947.54 2109.56 3757.33 846.194 1871.23 2406.41 2039.02 674.4011680_MZ Phosphatidylserine with formula C34H62NO10P Un 1.0 None None None None PS(14:1(9Z)/14:1(9Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PS(14:1(9Z)/14:1(9Z)), in particular, consists of one chain of myristoleic acid at the C-1 position and one chain of myristoleic acid at the C-2 position. The myristoleic acid moiety is derived from milk fats, while the myristoleic acid moiety is derived from milk fats. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE. C34H62NO10P None None None 6576.42 10414.7 13171.3 9683.41 19968.6 17828.8 9986.06 6837.2 12290.3 15036.7 20986.7 16188.5 2844.98 13574.8 14873.9 11642.7 3866.11 3560.81 7756.23 6643.4 8558.83 13476.9 13681.1 7475.83 10700.7 12814.7 13862.6 11076.3 12531.6 13362.0 6779.69 7393.5 18989.5 6434.92 11043.8 7840.51 8697.36 16359.2 4249.58 13650.8 2828.9 5225.43 674.5138333_MZ Phosphatidylethanolamine (14:0/P-18:0) Un 1.0 None None None None PE(14:0/P-18:0) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(14:0/P-18:0), in particular, consists of one chain of myristic acid at the C-1 position and one chain of plasmalogen 18:0 at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the plasmalogen 18:0 moiety is derived from animal fats, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. C37H74NO7P None None None 2697.58 1534.17 1706.55 1906.56 3271.4 1798.54 3509.7 3255.49 1991.06 2255.98 2623.05 2452.21 3430.35 3015.81 1822.77 2116.54 1440.23 4798.46 1529.29 3266.75 1847.62 1376.34 2104.79 2102.3 2239.58 2568.86 1769.05 2551.92 1367.14 1686.76 2443.3 4220.97 2651.75 1369.28 1064.77 1806.16 1889.85 1999.2 1412.75 1806.82 3305.81 2801.51 675.4745218_MZ Phosphatidic Acid with formula C37H69O7P Un 1.0 None None None None 2-(9Z,12Z-octadecadienoyl)-1-(1Z-hexadecenyl)-sn-glycero-3-phosphate is an intermediate of ether lipid metabolism. Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. 2-(9Z,12Z-octadecadienoyl)-1-(1Z-hexadecenyl)-sn-glycero-3-phosphate is irreversibly produced from 2-(9Z,12Z-octadecadienoyl)-1-(1Z-hexadecenyl))-sn-glycero-3-phosphoethanolamine via the enzyme phospholipase D (EC: 3.1.4.4). Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. C37H69O7P None None None 33353.0 12336.3 13586.3 26476.4 28952.8 17299.4 37621.7 47039.5 13228.4 21850.9 21336.2 11102.2 74649.7 30080.0 10559.9 23850.8 11346.2 138413.0 11351.3 26571.9 10646.1 7451.8 19405.1 29576.9 18886.7 12630.7 12758.3 46202.4 15811.4 18663.8 24501.3 40348.8 17948.4 9552.44 12951.3 29622.4 13014.6 13640.0 26568.0 18788.2 51121.0 45454.8 675.5865555_MZ Diglyceride (16:1(9Z)/24:1(15Z)/0:0) Un 1.0 None None None None DG(16:1(9Z)/24:1(15Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(16:1(9Z)/24:1(15Z)/0:0), in particular, consists of one chain of palmitoleic acid at the C-1 position and one chain of nervonic acid at the C-2 position. The palmitoleic acid moiety is derived from animal fats and vegetable oils, while the nervonic acid moiety is derived from fish oils. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C43H80O5 None None None 994.9 1304.13 735.414 711.394 298.022 983.191 1485.48 489.645 230.92 356.988 503.423 1271.08 569.33 436.275 460.768 2282.12 473.414 1589.08 389.891 725.533 630.969 246.617 320.364 1116.07 484.249 351.765 817.922 974.608 352.931 1156.99 996.928 1782.75 545.212 312.945 178.747 476.218 355.877 431.303 597.059 139.136 732.622 268.11 677.4202509_MZ Fucoxanthin Un 1.0 None None None None Fucoxanthin is a carotenoid, with formula C40H60O6. It is found as an accessory pigment in the chloroplasts of brown algae and most other heterokonts, giving them a brown or olive-green color. Fucoxanthin absorbs light primarily in the blue-green to yellow-green part of the visible spectrum, peaking at around 510-525 nm by various estimates and absorbing significantly in the range of 450 to 540 nm. -- Wikipedia. C42H58O6 None None None 3287.85 3911.28 4896.62 3764.8 6196.91 6174.66 4684.58 3140.03 3952.97 4502.64 6427.59 4653.38 2005.04 5332.4 5543.58 4253.02 2951.53 1579.21 3177.46 3670.86 3311.33 3858.49 4586.47 3083.08 3950.2 3525.36 4557.15 3637.07 3622.24 4662.21 3272.43 3147.53 4535.74 3227.72 3371.28 2998.8 2971.07 4461.4 1828.89 4332.16 2634.32 2168.61 678.0947527_MZ UDP-N-acetylmuraminate Un 1.0 None None None None UDP-N-acetylmuraminate is a nucleoside diphosphate sugar which is formed from UDP-N-acetylglucosamine and phosphoenolpyruvate. It serves as the building block upon which peptidoglycan is formed. C20H31N3O19P2 None None None 17876.5 18434.9 14088.0 21417.8 9984.62 22400.9 12279.3 12668.0 10019.3 19702.5 12341.2 14764.3 11167.8 19697.1 14679.1 29263.2 11119.3 11420.4 12074.6 11159.7 12693.7 14545.2 11584.2 14994.9 12383.9 16226.7 12234.6 14148.8 17019.6 17159.5 21851.9 28187.3 13849.2 12397.3 21265.1 15627.8 14090.8 15642.7 21375.2 12135.6 17976.4 11999.8 678.6913490_MZ Ceramide (d18:0/26:0) Un 1.0 None None None None Ceramides (N-acylsphingosine) are one of the hydrolysis byproducts of sphingomyelin by the enzyme sphingomyelinase (sphingomyelin phosphorylcholine phosphohydrolase E.C.3.1.4.12) which has been identified in the subcellular fractions of human epidermis (PMID 25935) and many other tissues. They can also be synthesized from serine and palmitate in a de novo pathway and are regarded as important cellular signals for inducing apoptosis (PMID 14998372). Is key in the biosynthesis of glycosphingolipids and gangliosides. C44H89NO3 None None None 2007.84 2360.14 1975.96 3025.54 2337.17 2510.65 2083.98 2038.7 1922.12 2403.1 2187.9 1928.54 2055.14 2059.14 2162.32 3540.11 1927.47 1793.61 1831.52 1955.27 2072.52 2143.46 2325.32 1926.5 1975.85 2223.77 2186.43 2385.05 2202.47 2192.73 2723.29 3647.15 1717.26 2086.22 2450.06 2292.09 1847.41 2054.7 2017.73 2271.14 2113.37 2108.18 679.6246213_MZ Diglyceride (16:0/24:0/0:0) Un 1.0 None None None None DG(16:0/24:0/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(16:0/24:0/0:0), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of lignoceric acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the lignoceric acid moiety is derived from groundnut oil. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C43H84O5 None None None 194.567 263.066 122.799 170.209 388.079 429.929 105.972 680.193 148.974 1341.08 2213.88 239.547 147.594 505.616 680.4936384_MZ Phosphatidylethanolamine (15:0/P-16:0) Un 1.0 None None None None PE(15:0/P-16:0) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(15:0/P-16:0), in particular, consists of one chain of pentadecanoic acid at the C-1 position and one chain of plasmalogen 16:0 at the C-2 position. The pentadecanoic acid moiety is derived from dairy products and milk fat, while the plasmalogen 16:0 moiety is derived from animal fats, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. C36H72NO7P None None None 2928.56 1566.47 1231.4 2684.59 2767.19 2176.68 3467.12 3068.09 1464.18 2094.65 1811.87 1394.7 3867.77 3696.34 1142.56 3721.6 1117.0 5449.95 1151.16 5895.12 1061.41 690.623 1872.24 2011.5 2034.59 1518.48 1425.35 2723.74 1325.8 2049.89 5280.65 5775.33 1964.97 1601.34 1353.23 2363.51 1207.49 2044.02 1870.12 1460.58 4600.6 3073.91 683.5038432_MZ Diglyceride (18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) Un 1.0 None None None None DG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0), in particular, consists of one chain of linoleic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The linoleic acid moiety is derived from seed oils, while the docosahexaenoic acid moiety is derived from fish oils. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C43H68O5 None None None 4605.95 5133.31 3752.11 5279.32 6024.69 4329.67 8778.35 8065.35 5849.32 4817.87 5351.09 5225.71 7438.02 6729.06 2898.5 4325.07 6362.74 9565.98 4438.42 5875.22 3266.11 2680.85 6166.01 4693.56 6528.06 3307.71 3064.34 9645.43 4492.48 5573.56 5895.07 3219.83 7557.85 5127.19 2055.38 6833.59 5913.44 6272.84 6233.91 5740.65 7621.16 6692.44 687.5390396_MZ Diglyceride (18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) Un 1.0 None None None None C43H72O5 None None None 34259.0 22185.3 28360.4 26870.4 36065.7 23397.4 41687.0 41351.8 33277.3 27851.8 32515.1 35661.8 35913.1 38703.3 25834.8 19869.5 25551.8 52343.9 20159.0 37545.5 27619.2 26036.2 30938.0 24826.4 27829.7 32304.2 20010.8 41959.4 25198.0 22599.7 29604.3 20028.8 46842.1 19633.3 14382.7 26051.5 29960.0 31313.5 27184.6 30006.2 31256.3 35551.7 688.4906140_MZ Phosphatidylcholine (14:1(9Z)/15:0) Un 1.0 None None None None PC(14:1(9Z)/15:0) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(14:1(9Z)/15:0), in particular, consists of one chain of myristoleic acid at the C-1 position and one chain of pentadecanoic acid at the C-2 position. The myristoleic acid moiety is derived from milk fats, while the pentadecanoic acid moiety is derived from dairy products and milk fat. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C37H72NO8P None None None 9512.38 7620.85 4789.92 7387.95 6357.69 4013.61 6570.99 6310.46 7594.49 4194.3 8244.5 9376.29 3495.17 8827.91 5190.46 6027.79 7709.81 5211.87 6053.28 4254.4 5455.89 3876.28 5660.76 4866.14 5861.86 5494.72 5722.16 5503.23 2341.61 5928.81 6874.48 6511.65 5733.46 5083.67 3727.34 3887.85 6141.33 4217.78 2332.92 5763.3 4517.54 5008.4 690.5060612_MZ Phosphatidylcholine (14:0/15:0) Un 1.0 None None None None PC(14:0/15:0) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(14:0/15:0), in particular, consists of one chain of myristic acid at the C-1 position and one chain of pentadecanoic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the pentadecanoic acid moiety is derived from dairy products and milk fat. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C37H74NO8P None None None 2812.52 2587.35 1942.42 2074.72 3183.79 1906.32 2976.27 3520.04 2457.91 2262.52 3019.29 3649.88 2599.41 5199.18 2382.51 2771.3 3051.34 2141.22 1813.88 2360.5 1965.54 1439.23 2472.5 1783.82 2294.88 2462.56 2269.23 2082.38 973.954 2406.39 2579.16 2817.88 2597.3 1421.18 1441.07 1360.64 1945.59 2702.6 1109.89 2271.51 1811.52 1754.32 695.1144887_MZ Diadenosine diphosphate Un 1.0 None None None None Diadenosine diphosphate is a member of the diadenosine polyphosphates. Diadenosine diphosphate is typically synthesized from ADP-ribosyl cyclases. Diadenosine polyphosphates are members of a group of dinucleoside polyphosphates that are ubiquitous, naturally occurring molecules. They form a recently identified class of compounds derived from ATP and consist of two adenosine molecules bridged by up to six phosphate groups. These compounds are stored in high concentrations in platelet dense granules and are released when platelets become activated. Some of the compounds promote platelet aggregation, while others are inhibitory. Possible roles as neurotransmitters, extracellular signalling molecules or 'alarmones' secreted by cells in response to physiologically stressful stimuli have been postulated. Recent studies suggest a role for these compounds in atrial and synaptic neurotransmission. Studies using isolated mesenteric arteries indicate an important role of phosphate chain length in determining whether diadenosine polyphosphates produce vasodilatation or vasoconstriction, but in the coronary circulation, diadenosine polyphosphates generally produce vasodilatation via mechanisms thought to involve release of NO or prostacyclin (PGI2). They produce cardiac electrophysiological effects by altering ventricular refractoriness at submicromolar concentrations and reduce heart rate. Mechanisms involving KATP channels have been proposed in addition to the involvement of P1- and P2-purinergic receptors and the specific diadenosine polyphosphate receptor identified on isolated cardiac myocytes. Clinical evidence suggests a role for diadenosine polyphosphates in hypertensive patients and those with the Chediak-Higashi syndrome. (PMID: 10434992). C20H26N10O13P2 None None None 3765.67 3048.93 3894.39 2747.83 2794.25 3773.83 3727.19 3479.27 3335.7 3348.25 2523.41 3291.77 3638.42 2595.24 3532.75 4199.75 2932.85 4153.43 3369.56 3341.85 3525.71 3460.24 2867.0 3426.99 3327.8 3553.94 3429.89 3440.81 3752.5 3256.86 3019.48 2441.26 3170.91 3067.02 4720.1 3903.08 3392.69 3828.61 2541.66 3348.87 3893.91 3431.27 697.2577712_MZ Pentacarboxylporphyrin I Un 1.0 None None None None Pentacarboxylporphyrin I is a bile product that arises from the conversion of Pentacarboxylporphyrinogen I to Pentacarboxylporphyrin I by porphyrinogen carboxy-lyase (EC 4.1.1.37). C37H38N4O10 None None None 382.862 355.571 501.962 486.007 973.658 622.355 490.483 549.021 417.468 381.01 531.48 680.039 337.63 537.793 650.973 1012.1 411.084 239.433 467.239 440.151 399.229 332.107 500.905 323.113 504.158 425.806 733.193 404.356 377.605 433.576 191.978 347.318 488.289 300.752 333.856 558.151 300.597 282.147 112.249 499.67 389.061 570.011 697.6123520_MZ Diglyceride (16:0/24:1(15Z)/0:0) Un 1.0 None None None None DG(16:0/24:1(15Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(16:0/24:1(15Z)/0:0), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of nervonic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the nervonic acid moiety is derived from fish oils. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C43H82O5 None None None 670.357 1600.78 501.732 778.495 772.359 883.517 1425.41 440.253 773.169 364.57 965.482 1548.09 302.4 742.538 750.951 1882.89 972.178 1690.33 440.315 984.382 921.952 353.228 706.964 959.201 797.323 802.859 1397.01 1073.88 299.605 833.537 974.722 1694.7 704.65 899.667 255.076 466.345 595.571 1224.85 588.762 288.113 1841.75 428.958 698.2099964_MZ Pteroyltriglutamic acid Un 1.0 None None None None Pteroyltriglutamic acid is a crystalline conjugate of folic acid containing three molecules of glutamic acid instead of one and having the general properties of a polypeptide. (http://medical-dictionary.thefreedictionary.com/pteropterin). As a measure of enterocyte function, the deconjugation of Pteroylpolyglutamic acid (pteroyl-L-glutamyl-gamma-L-glutamyl-gamma-L-glutamic acid) to folic acid and subsequent active absorption was measured in 19 patients with progressive systemic sclerosis and compared with 14 controls. The absorption step of folic acid was identical in the two groups, while deconjugation of pteroyl-L-glutamyl-gamma-L-glutamyl-gamma-L-glutamic acid was significantly decreased in the patients with progressive systemic sclerosis. This observation suggests a primary epithelial defect of the small intestine in patients with progressive systemic sclerosis. (PMID 3583071). Glutamyl hydrolase cleaves the poly-g-glutamate chain folate and antifolate poly-g-glutamates. Its cellular location is lysosomal with large amts. of the enzyme constitutively secreted. The highest levels of glutamyl hydrolase mRNA in humans is found in the liver and kidney. (PMID: 10598552). C29H33N9O12 None None None 3491.02 3243.78 3570.47 8121.56 3407.59 3882.98 3681.27 3288.13 2807.85 5766.06 3149.13 3026.65 4163.92 4530.21 4334.78 7207.74 4434.2 3275.43 4246.99 3776.65 3278.49 3172.08 3628.67 3435.78 6175.45 3122.96 4879.17 3535.57 4012.62 5130.57 4709.9 7368.36 3117.55 3594.69 4127.44 3616.32 3579.38 3155.86 3823.2 3773.9 5470.61 5561.49 698.4367440_MZ Phosphatidylserine (14:0/14:0) Un 1.0 None None None None PS(14:0/14:0) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PS(14:0/14:0), in particular, consists of two chains of myristic acid both at the C-1 position and the C-2 position. The myristic acid moiety is derived from nutmeg and butter. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE. C34H66NO10P None None None 3588.27 6526.39 8254.31 6099.53 11618.0 9473.31 5678.37 4168.7 8298.95 8545.29 13085.2 9816.22 1323.25 8542.64 7665.4 5000.69 2207.02 746.668 4539.71 3597.79 4952.83 8320.05 7633.3 4730.42 6028.51 7805.04 7677.12 6702.22 7326.61 8378.5 4011.35 3702.56 11165.0 4038.39 5902.03 4746.04 5447.0 9534.39 2768.95 8180.19 1645.42 3168.82 698.5115240_MZ Phosphatidylethanolamine (16:1(9Z)/P-18:1(11Z)) Un 1.0 None None None None PE(16:1(9Z)/P-18:1(11Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(16:1(9Z)/P-18:1(11Z)), in particular, consists of one chain of palmitoleic acid at the C-1 position and one chain of plasmalogen 18:1n7 at the C-2 position. The palmitoleic acid moiety is derived from animal fats and vegetable oils, while the plasmalogen 18:1n7 moiety is derived from animal fats, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. C39H74NO7P None None None 7416.38 9427.17 5228.19 7959.27 4189.73 4391.37 7551.64 6513.63 6952.52 4674.66 7749.57 9148.52 5211.87 8277.37 3262.18 4554.68 9642.91 5774.16 4261.46 6247.5 7989.67 4265.77 7289.99 5091.84 6520.65 5398.33 6024.68 8135.78 4344.15 7736.45 7369.26 4873.34 6084.08 5594.66 5113.52 6251.35 6109.19 5879.71 3172.98 5197.02 5106.53 5121.43 698.5549652_MZ Galactosylceramide (d18:1/16:0) Un 1.0 None None None None Galactosylceramides (GalCer) are non-acidic monoglycosphingolipids, i.e. a sphingolipid with one carbohydrate moiety attached to a ceramide unit. They are an intermediate in sphingolipid metabolism and is the second to last step in the synthesis of digalactosylceramidesulfate. GalCer is generated from ceramide via the enzyme UDP-galactose ceramide galactosyltransferase [EC:2.4.1.47]. It can be converted to digalactosylceramide via the enzyme glycosyltransferases [EC 2.4.1.-]. Galactosylceramide is the principal glycosphingolipid in brain tissue, hence the trivial name cerebroside, which was first conferred on it in 1874. Galactosylceramides are found in all nervous tissues, but they can amount to 2% of the dry weight of grey matter and 12% of white matter. They are major constituents of oligodendrocytes. Synthesis of galactosylceramide takes place on the lumenal surface of the endoplasmic reticulum, although it has free access to the cytosolic surface by an energy-independent flip-flop process. GalCer sits in the extracellular leaflet of cell membranes in nanometer sized domains or rafts. The local clustering of GalCer within rafts is thought to facilitate the initial adhesion of certain viruses, including HIV-1 and bacteria to cells through multivalent interactions between receptor proteins and GalCer. A defect in the degradation of cerbrosides leads to a disorder called Krabbe disease. Krabbe disease (also known as globoid cell leukodystrophy or galactosylceramide lipidosis) is a rare, often fatal degenerative disorder that affects the myelin sheath of the nervous system. Krabbe disease is caused by mutations in the GALC gene, which causes a deficiency of galactosylceramidase. Infants with Krabbe disease are normal at birth. Symptoms begin between the ages of 3 and 6 months with irritability, fevers, limb stiffness, seizures, feeding difficulties, vomiting, and slowing of mental and motor development. There are also juvenile- and adult-onset cases of Krabbe disease, which have similar symptoms but slower progression. In infants, the disease is generally fatal before age 2. Patients with late-onset Krabbe disease tend to have a slower progression of the disease and live significantly longer.Cerebrosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Cerebrosides have a single sugar group linked to ceramide. The most common are galactocerebrosides (containing galactose), the least common are glucocerebrosides (containing glucose). Galactocerebrosides are found predominantly in neuronal cell membranes. In contrast glucocerebrosides are not normally found in membranes. Instead, they are typically intermediates in the synthesis or degradation of more complex glycosphingolipids. Galactocerebrosides are synthesized from ceramide and UDP-galactose. Excess lysosomal accumulation of glucocerebrosides is found in Gaucher disease. C40H77NO8 None None None 13410.2 2864.39 4536.74 3465.67 9057.21 2693.19 5769.79 9235.39 4439.51 3328.28 5589.65 5207.96 9117.94 12037.7 5791.7 2645.86 9988.37 5027.84 3156.23 4461.09 5673.09 2548.29 5415.02 3534.85 3976.37 5112.18 4607.67 4816.8 3547.46 3662.63 3908.02 2982.47 5642.69 2222.43 3702.55 3196.69 3820.12 4777.8 3081.72 5203.86 3532.74 5201.84 699.4945604_MZ Phosphatidic acid (18:0/18:2(9Z,12Z)) Un 1.0 None None None None PA(18:0/18:2(9Z,12Z)) is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(18:0/18:2(9Z,12Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of linoleic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the linoleic acid moiety is derived from seed oils. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. Indeed, the concentration of phosphatidic acids is often over-estimated in tissues and biofluids as it can arise by inadvertent enzymatic hydrolysis during inappropriate storage or extraction conditions during analysis. The main biosynthetic route of phosphatidic acid in animal tissues involves sequential acylation of alpha-glycerophosphate by acyl-CoA derivatives of fatty acids. PAs are biologically active lipids that can stimulate a large range of responses in many different cell types, such as platelet aggregation, smooth muscle contraction, in vivo vasoactive effects, chemotaxis, expression of adhesion molecules, increased tight junction permeability of endothelial cells, induction of stress fibres, modulation of cardiac contractility, and many others. Diacylglycerols (DAGs) can be converted to PAs by DAG kinases and indirect evidence supports the notion that PAs alter the excitability of neurons. Phospholipase Ds (PLDs), which catalyze the conversion of glycerolphospholipids, particularly phosphatidylcholine, to PAs and the conversion of N-arachidonoyl-phosphatidylethanolamine (NAPE) to anandamide and PAs are activated by several inflammatory mediators including bradykinin, ATP and glutamate. PAs activate downstream signaling pathways such as PKCs and mitogen-activated protein kinases (MAPKs), which are linked to an increase in sensitivity of sensory neurons either during inflammation or in chronic pain models. Circumstantial evidence that PAs are converted to DAGs. (PMID: 12618218, 16185776). C39H73O8P None None None 42144.5 36130.0 38545.7 71214.1 34366.4 29334.9 50550.5 50267.1 42341.3 32733.9 52198.8 65641.7 45985.2 40454.9 27455.6 31833.0 44064.9 48188.4 25978.8 44187.4 39101.8 27182.3 33999.7 31206.8 42741.9 43778.5 36001.2 48916.4 31455.2 34051.3 103107.0 73406.2 37033.8 33312.6 26493.0 34143.3 41134.7 32455.5 21466.7 30545.2 39049.8 38590.7 699.6447756_MZ Cholesterol Ester (20:0) Un 1.0 None None None None CE(20:0) is a cholesterol fatty acid ester or simply a cholesterol ester (CE). Cholesterol esters are cholesterol molecules with long-chain fatty acids linked to the hydroxyl group. They are much less polar than free cholesterol and appear to be the preferred form for transport in plasma and for storage. Cholesterol esters do not contribute to membranes but are packed into intracellular lipid particles or lipoprotein particles. Because of the mechanism of synthesis, plasma cholesterol esters tend to contain relatively high proportions of C18 fatty acids. Cholesterol esters are major constituents of the adrenal glands and they also accumulate in the fatty lesions of atherosclerotic plaques. Cholesterol esters are also major constituents of the lipoprotein particles carried in blood (HDL, LDL, VLDL). The cholesterol esters in high-density lipoproteins (HDL) are synthesized largely by transfer of fatty acids to cholesterol from position sn-2 (or C-2) of phosphatidylcholine catalyzed by the enzyme lecithin cholesterol acyl transferase (LCAT). The enzyme also promotes the transfer of cholesterol from cells to HDL. As cholesterol esters accumulate in the lipoprotein core, cholesterol is removed from its surface thus promoting the flow of cholesterol from cell membranes into HDL. This in turn leads to morphological changes in HDL, which grow and become spherical. Subsequently, cholesterol esters are transferred to the other lipoprotein fractions LDL and VLDL, a reaction catalyzed by cholesteryl ester transfer protein. Another enzyme, acyl-CoA:cholesterol acyltransferase (ACAT) synthesizes cholesterol esters from CoA esters of fatty acids and cholesterol. Cholesterol ester hydrolases liberate cholesterol and free fatty acids when required for membrane and lipoprotein formation, and they also provide cholesterol for hormone synthesis in adrenal cells. C47H84O2 None None None 77.1943 63.8917 333.699 3.87875 31.8706 204.795 360.79 194.145 73.8327 540.623 3646.86 15.4356 322.925 357.525 5041.74 703.6163677_MZ Diglyceride (18:1(11Z)/24:1(15Z)/0:0) Un 1.0 None None None None DG(18:1(11Z)/24:1(15Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(18:1(11Z)/24:1(15Z)/0:0), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of nervonic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the nervonic acid moiety is derived from fish oils. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C45H84O5 None None None 564.984 902.643 369.754 790.043 218.548 578.044 1021.47 870.321 186.178 254.405 316.499 615.229 435.865 202.506 1442.35 917.014 802.908 219.468 543.582 568.837 57.7054 426.702 622.352 376.844 833.884 787.447 592.407 303.919 675.567 621.335 1222.02 232.478 195.997 312.182 398.826 537.106 788.241 242.115 331.117 453.259 117.759 705.6325794_MZ Diglyceride (18:0/24:1(15Z)/0:0) Un 1.0 None None None None DG(18:0/24:1(15Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(18:0/24:1(15Z)/0:0), in particular, consists of one chain of stearic acid at the C-1 position and one chain of nervonic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the nervonic acid moiety is derived from fish oils. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C45H86O5 None None None 211.706 254.863 299.861 540.982 160.022 598.796 274.612 675.216 164.6 507.687 209.678 167.549 555.289 326.178 88.4339 884.571 203.223 77.7706 976.781 287.948 154.454 471.554 126.021 335.131 375.062 391.137 240.141 212.418 718.27 710.26 180.061 598.453 243.008 188.071 110.042 267.785 305.776 404.142 1167.93 67.4824 706.2379919_MZ (a-D-mannosyl)2-b-D-mannosyl-N-acetylglucosamine Un 1.0 None None None None (alpha-D-mannosyl)2-beta-D-mannosyl-N-acetylglucosamine is an intermediate in aminosugars metabolism. It is substrate of Lysosomal alpha-mannosidase. C26H45NO21, Lacto-N-tetraose, Neolactotetraose, Alpha-D-Manp-(1 -> 2)-a-D-Manp-(1 -> 2)-a-D-Manp-(1 -> 3)-b-D-Manp-(1 -> 4)-D-GlcNAcp None None None 831.441 1157.3 932.575 1590.66 1211.95 1235.99 579.935 528.397 745.191 1034.43 1018.16 679.179 552.41 1073.5 1008.32 1043.23 789.48 830.598 1321.87 1053.27 1151.35 689.863 1240.14 1198.8 896.014 1322.09 1531.94 450.761 718.604 1006.72 639.893 952.558 551.886 788.554 499.771 1372.93 698.297 562.096 328.542 1170.27 706.148 1477.78 706.5243422_MZ Phosphatidylcholine (14:1(9Z)/P-16:0) Un 1.0 None None None None PC(14:1(9Z)/P-16:0) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(14:1(9Z)/P-16:0), in particular, consists of one chain of myristoleic acid at the C-1 position and one chain of plasmalogen 16:0 at the C-2 position. The myristoleic acid moiety is derived from milk fats, while the plasmalogen 16:0 moiety is derived from animal fats, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. C38H74NO7P None None None 609.593 484.682 340.606 733.879 778.121 669.296 1024.3 1191.99 242.646 558.848 336.555 472.885 597.19 989.656 302.743 781.339 237.916 759.383 209.69 1076.55 358.417 288.935 273.717 384.618 492.419 196.882 302.524 977.209 251.438 324.36 841.589 1630.06 890.563 203.046 392.519 438.945 441.432 421.354 445.366 305.424 659.556 1145.38 710.4634302_MZ Phosphatidylethanolamine (14:0/20:4(5Z,8Z,11Z,14Z)) Un 1.0 None None None None PE(14:0/20:4(5Z,8Z,11Z,14Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(14:0/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of myristic acid at the C-1 position and one chain of arachidonic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the arachidonic acid moiety is derived from animal fats and eggs. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. C39H70NO8P None None None 18655.8 9104.75 7331.33 12822.9 19239.5 13642.5 25322.4 21872.8 16238.8 12293.8 16447.5 14246.5 16454.0 18249.5 11332.1 14533.6 26464.1 7663.52 13579.6 15953.6 10670.9 6450.69 19854.0 8375.58 20296.1 13328.5 14188.4 8702.88 4508.91 21911.0 20262.6 13614.0 14295.1 11725.3 4521.42 6767.59 10353.6 12294.6 5656.59 9579.08 21014.4 11183.7 712.4892099_MZ Phosphatidylethanolamine (14:0/20:3(5Z,8Z,11Z)) Un 1.0 None None None None PE(14:0/20:3(5Z,8Z,11Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(14:0/20:3(5Z,8Z,11Z)), in particular, consists of one chain of myristic acid at the C-1 position and one chain of mead acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the mead acid moiety is derived from fish oils, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. C39H72NO8P None None None 31854.0 39354.3 26489.1 52814.4 34037.1 18403.3 44583.0 38169.8 53384.3 20118.1 41991.5 50092.9 22846.1 31384.9 28607.7 29566.6 66958.1 19047.4 34197.3 26397.7 27731.3 23936.4 37300.2 23761.1 39124.2 30395.7 39805.7 36231.9 14681.1 30224.1 45704.9 27349.2 29909.2 31826.4 23329.8 24527.5 30434.9 27800.5 12117.7 31489.7 28556.4 25677.3 713.5494699_MZ Diglyceride (20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) Un 1.0 None None None None DG(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0), in particular, consists of one chain of eicosenoic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The eicosenoic acid moiety is derived from vegetable oils and cod oils, while the docosahexaenoic acid moiety is derived from fish oils. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C45H74O5 None None None 2206.93 1860.82 1750.32 1880.65 2426.29 1610.43 3368.17 3861.04 2323.19 1778.24 2133.34 2051.16 2756.03 3581.7 1529.8 1766.86 2237.58 3280.16 1541.5 2779.26 1442.34 1440.93 2396.06 1800.04 2357.33 1734.16 1718.44 3195.36 1216.56 1599.88 2248.36 1551.8 3297.27 1849.42 933.279 1811.77 2380.08 2168.96 1855.76 2059.36 2804.14 3121.95 714.5069361_MZ Phosphatidylethanolamine (14:0/20:2(11Z,14Z)) Un 1.0 None None None None PE(14:0/20:2(11Z,14Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(14:0/20:2(11Z,14Z)), in particular, consists of one chain of myristic acid at the C-1 position and one chain of eicosadienoic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the eicosadienoic acid moiety is derived from fish oils and liver. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. C39H74NO8P None None None 294919.0 610322.0 325280.0 623782.0 249835.0 208734.0 419594.0 299329.0 501255.0 228957.0 494856.0 695508.0 130332.0 296275.0 261230.0 269615.0 749748.0 144655.0 314770.0 250733.0 372425.0 270499.0 410100.0 260177.0 398815.0 265367.0 404425.0 464131.0 202273.0 308997.0 523458.0 277030.0 225904.0 292842.0 247707.0 195232.0 379410.0 338134.0 150920.0 306572.0 177418.0 238117.0 716.5193608_MZ Phosphatidylcholine (15:0/16:1(9Z)) Un 1.0 None None None None PC(15:0/16:1(9Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(15:0/16:1(9Z)), in particular, consists of one chain of pentadecanoic acid at the C-1 position and one chain of palmitoleic acid at the C-2 position. The pentadecanoic acid moiety is derived from dairy products and milk fat, while the palmitoleic acid moiety is derived from animal fats and vegetable oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C39H76NO8P None None None 91017.5 133547.0 81294.6 123265.0 81094.1 54333.7 107217.0 96422.8 113035.0 56011.7 113683.0 170146.0 55537.2 123001.0 69145.3 73534.8 124815.0 74495.1 75788.3 82565.5 84107.6 68392.8 97038.4 72153.5 92332.6 100175.0 84312.6 106012.0 47843.5 74915.5 109700.0 77676.7 76165.7 75728.0 51627.9 55789.4 97234.9 78169.9 46243.6 76303.1 61621.9 70979.5 717.4825155_MZ Phosphatidylglycerol16:1(9Z)/16:1(9Z)) Un 1.0 None None None None C38H71O10P None None None 6632.32 7391.3 5726.43 8689.2 7057.0 6774.79 7743.63 7108.79 7133.83 6482.42 8662.73 8755.96 4295.21 7545.48 5367.23 7140.43 7442.57 6179.91 4747.33 6469.15 5904.46 4690.65 7418.97 5223.85 7222.75 6164.31 6340.53 7288.71 4511.83 7225.04 8520.49 6466.39 6176.71 5155.56 4250.48 5230.11 5129.57 6720.54 3706.08 5406.21 5636.96 5383.9 717.5919945_MZ Cholesterol ester (22:5(4Z,7Z,10Z,13Z,16Z)) Un 1.0 None None None None CE(22:5(4Z,7Z,10Z,13Z,16Z)) is a cholesterol fatty acid ester or simply a cholesterol ester (CE). Cholesterol esters are cholesterol molecules with long-chain fatty acids linked to the hydroxyl group. They are much less polar than free cholesterol and appear to be the preferred form for transport in plasma and for storage. Cholesterol esters do not contribute to membranes but are packed into intracellular lipid particles or lipoprotein particles. Because of the mechanism of synthesis, plasma cholesterol esters tend to contain relatively high proportions of C18 fatty acids. Cholesterol esters are major constituents of the adrenal glands and they also accumulate in the fatty lesions of atherosclerotic plaques. Cholesterol esters are also major constituents of the lipoprotein particles carried in blood (HDL, LDL, VLDL). The cholesterol esters in high-density lipoproteins (HDL) are synthesized largely by transfer of fatty acids to cholesterol from position sn-2 (or C-2) of phosphatidylcholine catalyzed by the enzyme lecithin cholesterol acyl transferase (LCAT). The enzyme also promotes the transfer of cholesterol from cells to HDL. As cholesterol esters accumulate in the lipoprotein core, cholesterol is removed from its surface thus promoting the flow of cholesterol from cell membranes into HDL. This in turn leads to morphological changes in HDL, which grow and become spherical. Subsequently, cholesterol esters are transferred to the other lipoprotein fractions LDL and VLDL, a reaction catalyzed by cholesteryl ester transfer protein. Another enzyme, acyl-CoA:cholesterol acyltransferase (ACAT) synthesizes cholesterol esters from CoA esters of fatty acids and cholesterol. Cholesterol ester hydrolases liberate cholesterol and free fatty acids when required for membrane and lipoprotein formation, and they also provide cholesterol for hormone synthesis in adrenal cells. C49H78O2 None None None 930.91 1164.8 793.437 915.024 1273.38 678.942 1621.51 1457.03 778.839 599.249 1073.96 1547.19 248.48 1104.72 815.393 1130.26 809.34 1130.69 548.856 1090.07 602.095 349.941 792.189 790.125 800.007 998.625 1042.82 1139.55 166.839 531.484 1014.21 1334.95 1162.13 716.27 736.119 514.348 831.489 1017.15 1158.47 448.961 441.747 613.45 718.4856490_MZ Phosphatidylethanolamine (15:0/18:3(6Z,9Z,12Z)) Un 1.0 None None None None C38H70NO8P None None None 3162.0 3486.9 3021.07 4157.8 4108.95 3603.18 4468.46 4196.88 3628.95 2935.82 4351.98 4553.96 2074.93 3651.46 3020.0 3710.81 4123.06 2985.96 2661.58 3565.22 2936.21 2333.11 3745.33 2534.57 3698.16 3115.04 3387.39 3838.76 2237.12 3252.44 4131.98 3827.73 3505.89 2797.71 2142.86 2712.8 2536.1 3369.88 1700.44 2738.12 3009.7 2782.53 719.6133733_MZ Cholesterol Ester with formula C49H80O2 Un 1.0 None None None None Cholesteryl docosatetraenoic acid is a cholesteryl ester. A cholesteryl ester is an ester of cholesterol. Fatty acid esters of cholesterol constitute about two-thirds of the cholesterol in the plasma. Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. The accumulation of cholesterol esters in the arterial intima (the innermost layer of an artery, in direct contact with the flowing blood) is a characteristic feature of atherosclerosis. Atherosclerosis is a disease affecting arterial blood vessels. It is a chronic inflammatory response in the walls of arteries, in large part to the deposition of lipoproteins (plasma proteins that carry cholesterol and triglycerides). Docosatetraenoic acid is one of the main polyunsaturated fatty acids (PUFA) present in the brain, a lipid-rich organ containing mostly complex polar phospholipids, sphingolipids, gangliosides and cholesterol. Cholesteryl docosatetraenoic acid has been found in triglycerides-rich cells such as monocyte-derived macrophages. Docosatetraenoic acid is increased in plasma in children with protein-calorie malnutrition (PCM). (PMID: 17392137, 10424250, 9162758). C49H80O2 None None None 222.268 419.44 187.593 115.941 114.636 365.353 300.356 692.12 166.593 253.956 346.288 280.644 218.151 336.066 332.368 478.526 175.284 210.072 357.72 46.3987 3.74087 104.743 357.58 292.95 436.867 646.227 148.123 31.9376 110.917 253.095 1441.47 121.662 324.669 69.0592 187.866 117.935 179.714 202.387 244.161 70.7266 720.4908368_MZ Phosphatidylethanolamine (18:4(6Z,9Z,12Z,15Z)/P-18:1(11Z)) Un 1.0 None None None None PE(18:4(6Z,9Z,12Z,15Z)/P-18:1(11Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(18:4(6Z,9Z,12Z,15Z)/P-18:1(11Z)), in particular, consists of one chain of stearidonic acid at the C-1 position and one chain of plasmalogen 18:1n7 at the C-2 position. The stearidonic acid moiety is derived from seed oils, while the plasmalogen 18:1n7 moiety is derived from animal fats, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. C41H72NO7P None None None 6471.6 4546.93 4646.23 4208.58 6308.51 4088.45 6051.1 6939.22 4519.94 3594.94 5966.81 5643.43 4206.65 6133.93 3631.79 4635.44 4564.46 9141.56 3235.26 5015.06 3958.82 3096.98 4610.98 4792.58 4794.53 5431.57 3692.41 5243.55 3294.81 4761.02 6178.29 7173.15 5039.07 3694.42 2699.46 4392.89 3974.02 3797.17 2610.37 3797.98 6476.4 5644.64 721.5641629_MZ Sphingomyelin with formula C39H79N2O6P Un 1.0 None None None None C39H79N2O6P None None None 30502.1 20318.4 26705.3 26522.1 34708.5 19243.7 34610.9 33917.6 32564.0 25445.2 32256.3 35205.8 26449.0 37611.2 28068.2 17327.1 26812.1 36667.2 18629.8 34607.4 29496.7 28342.0 28110.2 21344.5 25821.0 34728.0 20828.1 32091.2 24745.8 20643.2 25917.7 16327.2 41406.2 18509.7 14320.9 21603.9 28856.9 30935.3 21670.7 27911.5 26001.8 27545.8 723.0419655_MZ Molybdopterin-AMP Un 1.0 None None None None Molybdopterin-AMP is involved in molybdenum cofactor biosynthesis. ATP reacts with molybdopterin to produce molybdopterin-AMP and diphosphate. Molybdopterin-AMP reacts with molybdate to produce molybdenum cofactor, AMP, and H2O. C20H26N10O12P2S2 None None None 4982.81 4289.44 4854.24 3608.69 4676.35 5003.49 5570.35 4138.44 4947.62 3868.98 4394.38 4677.89 4042.42 4011.51 4376.0 5515.3 4083.73 4578.94 4235.97 4600.61 5498.39 5128.74 4025.54 5023.07 3720.8 4712.03 4666.3 4710.07 4533.15 4479.2 5084.66 4421.3 4633.28 3986.11 5447.93 5287.55 3765.5 4566.76 4280.18 4492.94 5176.51 4774.27 726.5000186_MZ Phosphatidylcholine (14:0/18:3(6Z_9Z_12Z)) Un 1.0 None None None None PC(14:0/18:3(6Z,9Z,12Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(14:0/18:3(6Z,9Z,12Z)), in particular, consists of one chain of myristic acid at the C-1 position and one chain of g-linolenic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the g-linolenic acid moiety is derived from animal fats. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C40H74NO8P None None None 16575.8 16833.8 19769.3 22280.6 30984.4 13391.1 33187.8 31223.7 21672.0 12392.8 19318.5 24627.4 32687.4 20682.8 17372.6 17242.0 29328.9 18451.0 16587.3 32018.0 14434.6 11442.3 19504.3 12874.9 24448.1 21262.2 17339.6 20501.4 10593.5 13991.2 27159.6 20004.6 21283.9 18340.2 9361.21 13058.9 16838.6 16114.8 11538.0 12106.6 31261.6 16320.5 726.5421023_MZ Phosphatidylethanolamine (18:1(11Z)/P-18:1(11Z)) Un 1.0 None None None None PE(18:1(11Z)/P-18:1(11Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(18:1(11Z)/P-18:1(11Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of plasmalogen 18:1n7 at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the plasmalogen 18:1n7 moiety is derived from animal fats, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. C41H78NO7P None None None 9641.57 10169.5 7397.31 9325.57 8191.75 5056.96 10578.3 9328.83 8630.97 5652.16 8522.0 9724.3 9126.31 11056.3 4670.9 7035.6 12504.8 8096.96 5580.58 9881.61 10020.2 5200.08 9097.45 6362.01 7805.51 7544.12 5864.13 9276.2 4600.96 9128.73 10778.5 9325.13 6947.15 7445.35 6743.51 6916.11 7500.79 7026.24 4743.0 5900.29 8657.08 6147.09 728.5233025_MZ Phosphatidylcholine (14:0/18:2(9Z_12Z)) Un 1.0 None None None None PC(14:0/18:2(9Z,12Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(14:0/18:2(9Z,12Z)), in particular, consists of one chain of myristic acid at the C-1 position and one chain of linoleic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the linoleic acid moiety is derived from seed oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C40H76NO8P None None None 16882.5 22729.4 15651.1 25300.3 12011.0 12326.2 19617.3 15583.3 18282.0 11838.6 18212.0 26993.6 11222.9 14638.8 11622.6 14951.5 23704.8 11755.4 11928.1 15259.1 15497.4 12343.8 17464.9 12735.8 15228.4 14357.3 16242.5 22060.0 11205.6 17100.8 24481.7 17431.3 12483.3 14981.1 10292.9 11303.6 16187.1 14419.6 8155.56 11666.8 11582.9 11339.5 729.5819173_MZ Ubiquinol 8 Un 1.0 None None None None Ubiquinol 8 is a ubiquinol in which the polyprenyl substituent is octaprenyl. Ubiquinol-8 is the reduced form of Ubiquinone-8. Ubiquinone (also known as coenzyme Q) is an isoprenoid quinone that functions as an electron carrier in membranes. In eukaryotes ubiquinone is found mostly within the inner mitochondrial membrane, where it functions in respiratory electron transport, transferring two electrons from either complex I (NADH dehydrogenase) or complex II (succinate-ubiquinone reductase) to complex III (bc1 complex). The quinone nucleus of ubiquinone is derived directly from 4-hydroxybenzoate, while the isoprenoid subunits of the polyisoprenoid tail are synthesized via the methylerythritol phosphate pathway, which feeds isoprene units into the Polyprenyl Biosynthesis pathways. The number of isoprenoid subunits in the ubiquinone side chain vary in different species. For example, Saccharomyces cerevisiae has 6 such subunits, Escherichia coli K-12 has 8, rat and mouse have 9, and Homo sapiens has 10. Ubiquinol-8 is effective as an anti-oxidant. By donating one of its hydrogen atoms to become the free-radical semiquinone (.Q-), it can neutralize a lipid peroxyl radical. The free-radical semiquinone is then restored to a non-free-radical state by the respiratory chain Q cycle. ubiquinol or the free-radical semiquinone can also regenerate the Vitamin E tocopheroxyl radical by electron donation (http://www.benbest.com/nutrceut/CoEnzymeQ.html). C49H78O4 None None None 1738.16 1646.55 1513.22 1821.94 1613.24 1154.01 2947.79 1860.75 1481.15 1339.44 1796.52 1793.84 1897.5 1641.97 1196.85 2135.02 2388.88 2165.1 1418.5 2556.88 1335.75 525.579 1749.51 1474.23 1503.14 1192.14 1698.78 2223.96 520.513 1463.46 2373.4 1825.63 1290.71 1609.09 666.619 926.32 1536.92 1409.14 1119.77 1142.81 1961.67 1205.34 730.4649315_MZ Phosphatidylserine (14:0/18:2(9Z_12Z)) Un 1.0 None None None None PS(14:0/18:2(9Z,12Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PS(14:0/18:2(9Z,12Z)), in particular, consists of one chain of myristic acid at the C-1 position and one chain of linoleic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the linoleic acid moiety is derived from seed oils. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE. C38H70NO10P None None None 4947.13 6988.46 7593.39 7360.84 10056.8 8736.75 7476.32 4436.03 7721.48 6839.29 10760.7 9999.72 2094.5 8199.57 8156.14 7844.06 4174.68 1415.65 5528.22 4416.67 6134.77 6747.26 8141.08 5210.92 7044.23 6651.33 9663.99 6146.05 5337.02 7905.27 5790.18 5521.71 8545.49 4777.95 6106.22 4504.62 5943.15 7798.17 2661.21 6956.32 2336.77 3660.64 730.5371018_MZ Phosphatidylcholine (14:0/18:1(11Z)) Un 1.0 None None None None PC(14:0/18:1(11Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(14:0/18:1(11Z)), in particular, consists of one chain of myristic acid at the C-1 position and one chain of vaccenic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the vaccenic acid moiety is derived from butter fat and animal fat. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C40H78NO8P None None None 7034.68 7814.06 5862.32 7323.13 5540.43 4936.82 7769.82 7407.48 7146.38 4663.83 7107.2 9550.3 4473.06 7326.37 5529.21 5562.27 6205.85 6646.28 4531.63 6993.76 5858.81 4813.61 6647.39 5173.17 5881.67 5643.51 5846.98 7685.39 3732.96 5970.2 7207.98 7459.13 5343.2 5522.69 3115.09 4539.69 5922.05 5044.15 4016.33 4637.33 4275.45 5011.97 731.6133888_MZ Sphingomyelin with formula C41H85N2O6P Un 1.0 None None None None Sphingomyelin (d18:0/18:0) or SM(d18:0/18:0) is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons. It usually consists of phosphorylcholine and ceramide. In humans, sphingomyelin is the only membrane phospholipid not derived from glycerol. Like all sphingolipids, SPH has a ceramide core (sphingosine bonded to a fatty acid via an amide linkage). In addition it contains one polar head group, which is either phosphocholine or phosphoethanolamine. The plasma membrane of cells is highly enriched in sphingomyelin and is considered largely to be found in the exoplasmic leaflet of the cell membrane. However, there is some evidence that there may also be a sphingomyelin pool in the inner leaflet of the membrane. Moreover, neutral sphingomyelinase-2 - an enzyme that breaks down sphingomyelin into ceramide has been found to localise exclusively to the inner leaflet further suggesting that there may be sphingomyelin present there. Sphingomyelin can accumulate in a rare hereditary disease called Niemann-Pick Disease, types A and B. Niemann-Pick disease is a genetically-inherited disease caused by a deficiency in the enzyme Sphingomyelinase, which causes the accumulation of Sphingomyelin in spleen, liver, lungs, bone marrow, and the brain, causing irreversible neurological damage. SMs play a role in signal transduction. Sphingomyelins are synthesized by the transfer of phosphorylcholine from phosphatidylcholine to a ceramide in a reaction catalyzed by sphingomyelin synthase. C41H85N2O6P None None None 252.926 254.99 140.243 143.835 214.492 181.353 329.0 513.802 233.99 796.278 121.162 164.438 64.4286 257.13 173.796 379.537 407.093 248.157 113.663 359.92 126.273 101.375 170.729 215.089 77.5472 150.559 266.177 90.9518 349.931 917.529 244.137 300.505 361.751 25.7601 200.869 325.265 219.868 135.96 401.48 64.437 731.6568447_MZ Diglyceride (20:1(11Z)/24:1(15Z)/0:0) Un 1.0 None None None None C47H88O5 None None None 165.898 317.434 307.036 385.748 94.7315 83.4161 200.1 461.238 257.605 188.464 212.371 264.325 29.374 272.176 140.284 195.602 515.346 453.147 80.1422 219.316 183.701 204.612 227.362 259.211 166.602 276.532 178.7 322.08 330.956 178.88 337.768 567.528 144.255 191.262 214.125 338.825 176.263 298.33 235.548 273.491 513.895 254.777 732.4872052_MZ Phosphatidylserine (14:0/18:1(9Z)) Un 1.0 None None None None PS(14:0/18:1(9Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PS(14:0/18:1(9Z)), in particular, consists of one chain of myristic acid at the C-1 position and one chain of oleic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE. C38H72NO10P None None None 3270.02 4034.48 3974.14 3940.73 5356.69 4450.87 5164.72 3852.62 4002.95 3137.92 4574.28 4899.73 2204.26 5156.04 4517.98 3797.09 4082.76 2020.67 3162.74 3649.02 3504.9 2850.83 3744.35 3304.19 4152.39 3552.5 4520.71 3468.78 2344.97 3613.43 4560.44 4330.32 4051.87 3261.28 2818.86 2427.16 3300.79 3668.54 1773.64 3121.14 2432.49 2600.82 733.6960226_MZ Cholesterol ester (24:1(15Z)) Un 1.0 None None None None C51H90O2 None None None 209.664 319.445 370.696 516.731 287.377 317.076 242.592 584.452 168.981 131.864 171.77 183.014 338.899 429.338 286.814 506.685 777.277 28.0909 114.8 355.186 321.002 178.44 239.973 172.348 485.854 361.781 314.597 189.957 223.78 246.773 302.453 758.454 149.594 291.209 363.013 308.436 166.96 196.014 443.024 267.104 191.004 167.578 735.5344384_MZ Diglyceride (22:4(7Z_10Z_13Z_16Z)/22:6(4Z_7Z_10Z_13Z_16Z_19Z)/0:0) Un 1.0 None None None None DG(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0), in particular, consists of one chain of adrenic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The adrenic acid moiety is derived from animal fats, while the docosahexaenoic acid moiety is derived from fish oils. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C47H72O5 None None None 5671.11 1756.58 2675.75 3607.73 6060.38 2988.41 4518.01 5316.41 2625.6 3022.6 3307.08 3486.15 5915.31 7880.29 4095.42 4706.95 5384.3 2359.62 2179.5 3073.45 2985.67 1552.76 3912.66 1773.23 2749.61 2678.33 3302.32 3518.93 1923.42 2652.95 4315.07 6064.67 2940.5 1666.22 2691.48 2101.6 1974.3 3144.05 1750.17 3384.93 2613.54 3307.33 736.2740351_MZ 5-Methyltetrahydropteroyltri-L-glutamate Un 1.0 None None None None 5-Methyltetrahydropteroyltri-L-glutamate is formed under reaction between carbonyl group of 5-Methyltetrahydropteroate and amine group on one end of three replicates of glutamate. It is involved in several pathways such as tetrahydrofolate biosynthesis II, methionine biosynthesis I,II,III as a product of enzymatic reduction; while in pathways folate polyglutamylation I and carbon tetrachloride degradation II as a product of enzymatic oxidation. In humans, this compound is produced by the bacteria in the gut and may be found in feces or urine. C30H39N9O12 None None None 803.341 949.859 445.164 2438.46 1246.6 1173.15 408.987 454.138 450.381 1461.09 2037.76 1129.25 127.516 1213.1 1031.09 626.773 623.674 777.301 1378.28 835.242 1643.87 588.695 3267.22 1922.16 906.404 416.875 1374.01 674.988 455.22 1109.83 715.355 1356.89 512.199 701.466 345.902 1734.09 393.924 465.616 533.698 1467.23 2099.73 2143.32 738.5072510_MZ Phosphatidylcholine (15:0/18:4(6Z_9Z_12Z_15Z)) Un 1.0 None None None None C41H74NO8P None None None 914144.0 1006080.0 834736.0 886299.0 846276.0 523343.0 1183450.0 918777.0 1072760.0 594994.0 1132270.0 1310730.0 800876.0 886513.0 604987.0 652736.0 1360290.0 985760.0 647689.0 1109990.0 813995.0 594121.0 967566.0 661041.0 916720.0 799517.0 718992.0 1265670.0 560482.0 673730.0 1108350.0 851759.0 827135.0 720661.0 542692.0 695215.0 950989.0 820439.0 596896.0 708719.0 871205.0 889248.0 740.5214468_MZ Phosphatidylcholine (15:0/18:3(6Z_9Z_12Z)) Un 1.0 None None None None PC(15:0/18:3(6Z,9Z,12Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(15:0/18:3(6Z,9Z,12Z)), in particular, consists of one chain of pentadecanoic acid at the C-1 position and one chain of g-linolenic acid at the C-2 position. The pentadecanoic acid moiety is derived from dairy products and milk fat, while the g-linolenic acid moiety is derived from animal fats. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C41H76NO8P None None None 342603.0 399531.0 271444.0 465839.0 304035.0 214728.0 448648.0 356646.0 494302.0 216278.0 422570.0 560094.0 234619.0 344007.0 221130.0 311498.0 557976.0 260296.0 270171.0 286400.0 351691.0 285792.0 428635.0 286883.0 361061.0 378199.0 354586.0 484451.0 266612.0 296453.0 446632.0 274632.0 310324.0 336403.0 279487.0 325552.0 230903.0 349963.0 157659.0 298862.0 259647.0 297164.0 741.2442107_MZ Hexacarboxylporphyrin I Un 1.0 None None None None Hexacarboxylporphyrin I is a bile product that arises from the conversion of Hexacarboxylporphyrinogen I to Hexacarboxylporphyrin I by porphyrinogen carboxy-lyase (EC 4.1.1.37). C38H38N4O12, Porphinehexacarboxylic acid, Hexacarboxylporphyrin III None None None 274.101 292.802 396.665 444.578 596.884 598.025 416.309 241.964 435.28 595.394 377.343 350.983 260.043 665.067 556.062 492.148 623.745 393.294 613.487 376.304 424.432 357.683 377.777 295.695 620.435 375.628 1092.08 233.059 393.258 707.156 430.712 580.079 451.007 332.989 308.241 519.377 504.082 458.374 203.13 514.56 6400.05 671.883 741.4358278_MZ Octaprenyl diphosphate Un 1.0 None None None None Octaprenyl diphosphate is the precursor for the side chain of the isoprenoid quinones ubiquinone and menaquinone. It is a substrate of enzyme trans-octaprenyltranstransferase [EC 2.5.1.11] in biosynthesis of steroids pathway (KEGG). C40H68O7P2 None None None 11161.1 8582.91 8051.52 10650.8 12842.9 10375.1 11847.8 10518.1 8990.2 8539.69 12847.9 8712.16 4907.0 12649.9 8757.79 7821.65 11537.1 4817.12 6964.2 10783.1 8020.24 6646.53 9962.95 7970.2 9255.7 10977.6 10947.4 7709.92 5784.35 12181.6 14429.5 7184.74 9007.01 9218.64 5714.62 7184.01 7682.39 8549.19 3870.21 9204.02 11858.9 6587.15 742.5086581_MZ Phosphatidylethanolamine (18:3(6Z_9Z_12Z)/P-18:1(11Z)) Un 1.0 None None None None PE(18:3(6Z,9Z,12Z)/P-18:1(11Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(18:3(6Z,9Z,12Z)/P-18:1(11Z)), in particular, consists of one chain of g-linolenic acid at the C-1 position and one chain of plasmalogen 18:1n7 at the C-2 position. The g-linolenic acid moiety is derived from animal fats, while the plasmalogen 18:1n7 moiety is derived from animal fats, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. C41H74NO7P None None None 15851.5 20806.7 15993.2 28910.9 21478.6 16463.6 21078.8 15723.5 19490.9 12430.1 23254.3 32424.8 32177.2 17925.1 13166.0 15239.5 19261.0 12742.6 12433.0 36655.5 16815.3 16229.0 20122.4 18615.3 37098.8 20270.6 18908.5 24194.6 12004.7 17036.2 18319.0 29022.7 16867.6 13364.0 14229.9 20585.3 14956.8 85896.1 11295.0 16113.5 10983.3 12715.2 742.5379142_MZ Phosphatidylcholine (15:0/18:2(9Z_12Z)) Un 1.0 None None None None PC(15:0/18:2(9Z,12Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(15:0/18:2(9Z,12Z)), in particular, consists of one chain of pentadecanoic acid at the C-1 position and one chain of linoleic acid at the C-2 position. The pentadecanoic acid moiety is derived from dairy products and milk fat, while the linoleic acid moiety is derived from seed oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C41H78NO8P None None None 757122.0 1161020.0 704780.0 1166450.0 543692.0 560356.0 903485.0 725379.0 881883.0 622587.0 1025120.0 1490310.0 452853.0 712122.0 500766.0 667820.0 1170070.0 669748.0 593632.0 736087.0 856715.0 586916.0 838348.0 579342.0 783063.0 670657.0 708970.0 1132880.0 605322.0 788295.0 1068110.0 568056.0 700930.0 669968.0 535414.0 625024.0 739232.0 712574.0 427862.0 581465.0 513560.0 560770.0 743.4883213_MZ Phosphatidylglycerol16:0/18:3(6Z_9Z_12Z)) Un 1.0 None None None None C40H73O10P None None None 17887.2 12381.0 10748.2 14963.2 18208.9 12102.0 14546.0 11547.9 15090.8 9501.42 16818.4 18999.1 8672.79 15451.2 13218.6 11412.7 10042.7 17527.2 8904.58 11885.2 10867.3 10959.1 13725.6 12043.7 14524.2 22881.6 14547.2 13858.6 8824.36 12526.0 17620.2 13312.1 11941.2 8416.29 8671.27 12420.0 9820.48 12316.5 7093.25 11250.1 10790.0 14432.8 744.0558459_MZ NADPH Un 1.0 None None None None Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.). C21H30N7O17P3 None None None 14347.3 12963.3 17282.4 14654.9 19938.3 15885.6 22870.4 16504.2 14437.1 12005.1 16017.5 14933.9 17716.2 10487.4 18964.2 24739.1 18206.7 10923.3 13677.9 18983.1 17505.3 16708.6 15449.1 15122.3 14888.7 16519.8 15698.5 15206.0 16909.4 11631.0 20739.3 16360.8 14528.2 13619.4 16891.7 12490.8 12861.7 16633.0 10493.3 14908.6 16076.6 15773.5 744.5517683_MZ Phosphatidylcholine (15:0/18:1(11Z)) Un 1.0 None None None None PC(15:0/18:1(11Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(15:0/18:1(11Z)), in particular, consists of one chain of pentadecanoic acid at the C-1 position and one chain of vaccenic acid at the C-2 position. The pentadecanoic acid moiety is derived from dairy products and milk fat, while the vaccenic acid moiety is derived from butter fat and animal fat. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C41H80NO8P None None None 264271.0 304076.0 245511.0 283897.0 249157.0 173823.0 286354.0 295254.0 266356.0 189084.0 312557.0 461453.0 210973.0 294886.0 199078.0 196239.0 208294.0 332013.0 174819.0 318301.0 236417.0 193854.0 222271.0 216721.0 240411.0 302611.0 205569.0 301434.0 191292.0 202033.0 267243.0 193720.0 279209.0 210931.0 148997.0 185878.0 247872.0 215012.0 188796.0 182826.0 210441.0 230257.0 745.5015018_MZ Phosphatidylglycerol16:0/18:2(9Z_12Z)) Un 1.0 None None None None PG(16:0/18:2(9Z,12Z)) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PG(16:0/18:2(9Z,12Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of linoleic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the linoleic acid moiety is derived from seed oils. Phosphatidylglycerol is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of phosphatidylglycerol increases during fetal development. Phosphatidylglycerol may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. C40H75O10P None None None 133480.0 109153.0 87067.4 62917.4 167333.0 97062.1 115176.0 157275.0 92156.5 83391.7 143730.0 164665.0 62958.1 126264.0 78807.9 85993.4 88726.8 175279.0 53428.7 81057.8 99019.6 81588.6 119878.0 88796.5 97214.7 178167.0 83370.3 129614.0 92732.2 99048.4 140486.0 128741.0 97343.5 55753.3 61554.9 89701.9 86903.7 121104.0 64773.6 77615.1 72266.3 136788.0 746.5126669_MZ Phosphatidylethanolamine (20:5(5Z_8Z_11Z_14Z_17Z)/P-18:1(11Z)) Un 1.0 None None None None PE(20:5(5Z,8Z,11Z,14Z,17Z)/P-18:1(11Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(20:5(5Z,8Z,11Z,14Z,17Z)/P-18:1(11Z)), in particular, consists of one chain of eicosapentaenoic acid at the C-1 position and one chain of plasmalogen 18:1n7 at the C-2 position. The eicosapentaenoic acid moiety is derived from fish oils, liver and kidney, while the plasmalogen 18:1n7 moiety is derived from animal fats, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. C43H74NO7P None None None 78194.5 78482.3 58816.1 60072.7 88933.3 55995.0 78954.2 108128.0 71464.9 51663.0 90283.3 97281.9 63769.0 98122.5 48872.0 52951.5 77254.9 109297.0 40874.4 71917.1 70001.3 52499.0 81574.7 51654.6 66952.4 84802.2 56393.3 95211.0 55964.4 75699.6 83660.6 74281.2 63508.0 50469.5 36287.9 54772.2 63410.2 70588.9 42653.8 55925.3 58383.3 75798.3 746.5905677_MZ Galactosylceramide (d18:1/18:0) Un 1.0 None None None None Galactosylceramides (GalCer) are non-acidic monoglycosphingolipids, i.e. a sphingolipid with one carbohydrate moiety attached to a ceramide unit. They are an intermediate in sphingolipid metabolism and is the second to last step in the synthesis of digalactosylceramidesulfate. GalCer is generated from ceramide via the enzyme UDP-galactose ceramide galactosyltransferase [EC:2.4.1.47]. It can be converted to digalactosylceramide via the enzyme glycosyltransferases [EC 2.4.1.-]. Galactosylceramide is the principal glycosphingolipid in brain tissue, hence the trivial name cerebroside, which was first conferred on it in 1874. Galactosylceramides are found in all nervous tissues, but they can amount to 2% of the dry weight of grey matter and 12% of white matter. They are major constituents of oligodendrocytes. Synthesis of galactosylceramide takes place on the lumenal surface of the endoplasmic reticulum, although it has free access to the cytosolic surface by an energy-independent flip-flop process. GalCer sits in the extracellular leaflet of cell membranes in nanometer sized domains or rafts. The local clustering of GalCer within rafts is thought to facilitate the initial adhesion of certain viruses, including HIV-1 and bacteria to cells through multivalent interactions between receptor proteins and GalCer. A defect in the degradation of cerbrosides leads to a disorder called Krabbe disease. Krabbe disease (also known as globoid cell leukodystrophy or galactosylceramide lipidosis) is a rare, often fatal degenerative disorder that affects the myelin sheath of the nervous system. Krabbe disease is caused by mutations in the GALC gene, which causes a deficiency of galactosylceramidase. Infants with Krabbe disease are normal at birth. Symptoms begin between the ages of 3 and 6 months with irritability, fevers, limb stiffness, seizures, feeding difficulties, vomiting, and slowing of mental and motor development. There are also juvenile- and adult-onset cases of Krabbe disease, which have similar symptoms but slower progression. In infants, the disease is generally fatal before age 2. Patients with late-onset Krabbe disease tend to have a slower progression of the disease and live significantly longer.Cerebrosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Cerebrosides have a single sugar group linked to ceramide. The most common are galactocerebrosides (containing galactose), the least common are glucocerebrosides (containing glucose). Galactocerebrosides are found predominantly in neuronal cell membranes. In contrast glucocerebrosides are not normally found in membranes. Instead, they are typically intermediates in the synthesis or degradation of more complex glycosphingolipids. Galactocerebrosides are synthesized from ceramide and UDP-galactose. Excess lysosomal accumulation of glucocerebrosides is found in Gaucher disease. C42H81NO8 None None None 7962.48 8220.38 6409.19 6331.98 7409.92 5891.33 10253.2 9076.66 6907.5 4745.4 8403.94 11449.7 7390.97 8304.95 6632.2 5961.43 6291.35 9297.79 4881.03 9812.38 6282.34 4622.89 6104.12 6544.41 6355.04 8163.77 5747.57 7608.71 4363.85 6642.28 7842.15 6206.18 6591.5 6778.74 3609.07 4660.99 5340.4 7828.57 5367.8 4894.89 6853.98 5725.28 748.4471974_MZ Phosphatidylserine (14:0/18:3(9Z_12Z_15Z)) Un 1.0 None None None None PS(14:0/18:3(9Z,12Z,15Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PS(14:0/18:3(9Z,12Z,15Z)), in particular, consists of one chain of myristic acid at the C-1 position and one chain of a-linolenic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the a-linolenic acid moiety is derived from seed oils, especially canola and soybean oil. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE. C38H68NO10P None None None 3024.27 3800.56 5057.09 4414.48 7792.02 7522.06 4540.48 2784.98 4321.2 4773.89 7352.3 5361.59 1974.56 6012.17 5944.91 5328.94 1866.94 1173.19 2994.03 3229.44 3132.91 5575.42 5129.89 3606.71 4350.54 4871.4 5301.77 3837.59 3849.52 4780.23 3738.26 4484.38 5684.62 2552.97 4028.64 3139.27 3538.06 6449.38 1756.35 5168.93 1557.53 2545.74 748.4907436_MZ Phosphatidylcholine (14:1(9Z)/20:5(5Z_8Z_11Z_14Z_17Z)) Un 1.0 None None None None PC(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)), in particular, consists of one chain of myristoleic acid at the C-1 position and one chain of eicosapentaenoic acid at the C-2 position. The myristoleic acid moiety is derived from milk fats, while the eicosapentaenoic acid moiety is derived from fish oils, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C42H72NO8P None None None 17473.7 21472.1 15890.4 28496.6 25140.8 15255.7 26224.1 27976.2 22567.9 15588.9 24672.0 25601.5 33935.2 17444.2 15384.9 16372.9 26855.3 19122.3 14443.2 31991.0 14588.8 14416.2 19756.5 14285.4 26150.5 21068.3 16346.3 24062.2 12896.9 16202.6 35275.2 41414.2 20066.5 17035.1 11689.5 15695.5 20079.0 31771.7 11161.0 15527.2 25202.8 17268.2 750.4631709_MZ 3-O-Sulfogalactosylceramide (d18:1/14:0) Un 1.0 None None None None 3-O-Sulfogalactosylceramide is an acidic, sulfated glycosphingolipid, often known as sulfatide. This lipid occurs in membranes of various cell types, but is found in particularly high concentrations in myelin where it constitutes 3-4% of total membrane lipids. This lipid is synthesized primarily in the oligodendrocytes in the central nervous system. Accumulation of this lipid in the lysosomes is a characteristic of metachromatic leukodystrophy, a lysosomal storage disease caused by the deficiency of arylsulfatase A. Alterations in sulfatide metabolism, trafficking, and homeostasis are present in the earliest clinically recognizable stages of Alzheimer's disease.Cerebrosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Cerebrosides have a single sugar group linked to ceramide. The most common are galactocerebrosides (containing galactose), the least common are glucocerebrosides (containing glucose). Galactocerebrosides are found predominantly in neuronal cell membranes. In contrast glucocerebrosides are not normally found in membranes. Instead, they are typically intermediates in the synthesis or degradation of more complex glycosphingolipids. Galactocerebrosides are synthesized from ceramide and UDP-galactose. Excess lysosomal accumulation of glucocerebrosides is found in Gaucher disease. Sulfatides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Sulfatides are the sulfuric acid esters of galactocerebrosides. They are synthesized from galactocerebrosides and activated sulfate, 3'-phosphoadenosine 5'-phosphosulfate (PAPS). C38H73NO11S None None None 3006.55 4073.18 4492.17 4131.73 6429.46 5780.64 4703.13 3618.92 4903.01 4464.41 6479.09 5361.11 1446.76 4996.18 4535.54 4398.03 2737.0 1941.86 3133.58 3281.29 3289.56 4098.68 4723.28 3459.08 4058.33 4658.22 5366.5 3758.73 3588.82 4487.96 3561.46 3515.76 5911.71 2887.02 3372.03 3004.59 3327.15 5486.96 2208.78 4334.78 1657.78 2429.38 750.5106633_MZ Phosphatidylcholine (14:0/20:5(5Z_8Z_11Z_14Z_17Z)) Un 1.0 None None None None C42H74NO8P None None None 24979.0 20287.3 22472.2 20889.6 25070.4 17884.2 29246.0 25656.3 25920.7 17668.5 28074.1 27153.2 37148.8 22803.6 16114.1 15948.7 23735.7 36058.3 17321.8 31793.0 18773.7 19267.9 22856.3 18309.4 24910.0 24910.4 16517.8 30696.7 21916.6 18617.8 27562.0 29073.7 26057.8 19249.4 16105.5 22911.3 21784.7 31390.2 18709.6 21712.2 29566.9 22200.2 750.5419080_MZ Phosphatidylethanolamine (20:3(5Z_8Z_11Z)/P-18:1(11Z)) Un 1.0 None None None None PE(20:3(5Z,8Z,11Z)/P-18:1(11Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(20:3(5Z,8Z,11Z)/P-18:1(11Z)), in particular, consists of one chain of mead acid at the C-1 position and one chain of plasmalogen 18:1n7 at the C-2 position. The mead acid moiety is derived from fish oils, liver and kidney, while the plasmalogen 18:1n7 moiety is derived from animal fats, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. C43H78NO7P None None None 111194.0 98926.1 90326.6 88502.8 75540.5 58079.6 110671.0 126934.0 97708.6 63978.5 106237.0 139378.0 91238.9 169756.0 63353.9 63736.5 101021.0 127218.0 64988.0 120564.0 83087.5 62611.6 96930.8 75727.7 80860.2 85359.8 66847.8 121752.0 60783.7 83397.3 100513.0 79656.5 97414.5 73538.8 54007.8 69231.5 80144.4 89284.5 72522.4 80025.3 76603.2 82121.8 752.4503563_MZ Phosphatidylserine (14:1(9Z)/20:4(5Z_8Z_11Z_14Z)) Un 1.0 None None None None PS(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PS(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of myristoleic acid at the C-1 position and one chain of arachidonic acid at the C-2 position. The myristoleic acid moiety is derived from milk fats, while the arachidonic acid moiety is derived from animal fats and eggs. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE. C40H68NO10P None None None 4368.38 5693.71 6400.72 5830.1 9048.48 7775.22 6591.68 5253.27 7135.22 6910.95 9586.74 8196.61 2596.98 6844.34 6714.17 5751.08 3807.28 2447.36 4477.31 4487.02 4574.27 6229.48 6959.07 4543.7 6297.15 7162.79 6672.14 6379.55 5741.88 6656.44 5206.87 4831.71 8276.49 4455.75 4882.11 4493.92 5054.87 7638.36 2973.78 6472.32 2629.49 3578.62 752.5233309_MZ Phosphatidylcholine (14:0/20:4(5Z_8Z_11Z_14Z)) Un 1.0 None None None None PC(14:0/20:4(5Z,8Z,11Z,14Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(14:0/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of myristic acid at the C-1 position and one chain of arachidonic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the arachidonic acid moiety is derived from animal fats and eggs. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C42H76NO8P None None None 41655.1 37070.8 34527.1 41142.2 28784.4 27791.6 52445.6 34343.8 38424.5 29958.0 36867.8 48834.5 33222.0 30512.7 24480.5 30817.0 47827.0 33546.2 23141.7 42404.6 37399.2 24965.9 43735.7 26302.9 35740.0 28336.4 31377.1 45294.2 26135.1 34155.1 53520.7 48032.9 33349.3 29366.0 21744.2 27628.1 31753.2 39633.0 25446.2 29185.2 29616.7 33665.3 753.6748750_MZ Diglyceride (20:0/24:1(15Z)/0:0) Un 1.0 None None None None DG(20:0/24:1(15Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(20:0/24:1(15Z)/0:0), in particular, consists of one chain of arachidic acid at the C-1 position and one chain of nervonic acid at the C-2 position. The arachidic acid moiety is derived from peanut oil, while the nervonic acid moiety is derived from fish oils. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C47H90O5 None None None 512.357 476.448 661.049 527.983 343.201 180.748 572.331 529.453 320.798 171.426 340.557 600.855 296.953 234.346 308.328 175.184 537.451 425.291 117.771 329.151 198.151 293.904 224.045 204.461 281.737 329.963 303.246 510.103 188.981 242.54 305.224 803.378 201.083 233.993 432.592 218.395 412.272 614.526 365.081 152.257 517.932 159.87 754.4849152_MZ Phosphatidylethanolamine (14:0/22:6(4Z_7Z_10Z_13Z_16Z_19Z)) Un 1.0 None None None None PE(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of myristic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the docosahexaenoic acid moiety is derived from fish oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. C41H70NO8P None None None 15648.1 8259.77 7975.99 9057.49 11214.9 13279.7 9397.71 7373.22 11300.2 11465.1 14727.9 12257.0 3136.89 17814.3 8048.9 7253.22 6605.52 2864.62 6148.56 7078.73 9165.89 7735.79 11997.2 7958.75 9687.25 10168.7 8002.55 9155.13 5956.45 21695.5 8314.79 5975.2 10071.9 6853.54 6497.66 5881.89 8596.34 9104.58 3754.5 7962.13 4108.84 4788.09 756.4864876_MZ Phosphatidylserine (14:0/20:3(8Z_11Z_14Z)) Un 1.0 None None None None PS(14:0/20:3(8Z,11Z,14Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PS(14:0/20:3(8Z,11Z,14Z)), in particular, consists of one chain of myristic acid at the C-1 position and one chain of homo-g-linolenic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the homo-g-linolenic acid moiety is derived from fish oils, liver and kidney. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE. C40H72NO10P None None None 9616.02 12930.9 11079.4 17612.8 14633.6 12389.9 12874.4 8557.18 14467.8 10554.0 16311.5 16562.9 4741.66 12248.5 10570.9 11484.9 12848.1 4618.9 10391.1 7874.61 10099.8 10453.3 14229.6 8670.46 12839.5 11871.3 13522.6 11271.2 8258.22 11981.6 13744.3 11062.7 12356.7 9376.55 8186.06 7623.27 10101.3 12388.5 5685.73 11064.1 5543.88 7571.36 756.5520987_MZ Phosphatidylcholine (14:0/20:2(11Z_14Z)) Un 1.0 None None None None PC(14:0/20:2(11Z,14Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(14:0/20:2(11Z,14Z)), in particular, consists of one chain of myristic acid at the C-1 position and one chain of eicosadienoic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the eicosadienoic acid moiety is derived from fish oils and liver. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C42H80NO8P None None None 23846.3 31392.5 21640.6 29576.1 18248.4 18612.4 26607.4 22526.6 27458.2 18991.5 31108.0 40262.0 14461.1 22034.3 16132.2 20491.0 34697.8 18238.9 17193.6 21045.5 25951.0 20664.4 26548.3 18788.0 22600.8 21709.7 22808.4 31852.1 20759.1 25279.0 26660.8 14753.7 22466.3 21473.0 17310.5 21560.1 21356.2 22261.5 12397.7 19277.5 13458.0 17301.2 758.4970034_MZ Phosphatidylserine (16:0/18:2(9Z_12Z)) Un 1.0 None None None None PS(16:0/18:2(9Z,12Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PS(16:0/18:2(9Z,12Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of linoleic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the linoleic acid moiety is derived from seed oils. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE. C40H74NO10P None None None 8505.49 12774.7 11885.2 13060.3 11910.2 15333.6 13603.1 9186.72 11491.2 11568.8 14768.9 18131.8 5176.81 14586.5 10586.7 10037.6 8969.71 3900.39 8695.07 7667.42 12245.0 10664.8 14572.4 8086.8 14129.2 12907.3 13668.2 12887.5 8899.28 14235.0 12319.9 9673.99 13357.0 8344.75 9116.38 6951.08 9764.75 13337.3 5566.49 10680.2 5267.77 7407.8 758.5668879_MZ Phosphatidylcholine (14:0/20:1(11Z)) Un 1.0 None None None None PC(14:0/20:1(11Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(14:0/20:1(11Z)), in particular, consists of one chain of myristic acid at the C-1 position and one chain of eicosenoic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the eicosenoic acid moiety is derived from vegetable oils and cod oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C42H82NO8P None None None 10074.1 10942.7 8882.29 9148.0 9029.14 7441.43 10331.4 10861.7 10315.9 7027.98 11501.5 15479.4 6142.82 10809.8 7712.86 7085.98 8382.72 10065.0 6440.68 10602.8 9381.74 8054.71 9347.48 8243.51 8510.32 10349.2 8370.12 10206.5 7572.82 8219.55 8446.74 6161.21 9665.43 7979.93 5989.44 7485.62 8652.15 8401.71 5920.8 7003.76 6412.51 7879.45 758.6070870_MZ Phosphatidylethanolamine (20:0/dm18:0) Un 1.0 None None None None PE(20:0/dm18:0) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(20:0/dm18:0), in particular, consists of one chain of arachidic acid at the C-1 position and one chain of plasmalogen 18:0 at the C-2 position. The arachidic acid moiety is derived from peanut oil, while the plasmalogen 18:0 moiety is derived from animal fats, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS.Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. C43H86NO7P None None None 2329.45 2524.32 1851.22 1850.73 1961.26 1375.16 2476.55 2300.3 2023.23 1507.67 2588.9 2715.41 1659.63 2900.98 1755.42 2352.0 2609.47 1872.75 1467.56 2316.39 1991.07 1239.42 2189.91 1870.44 1610.89 2031.49 1859.37 2048.6 1125.2 1539.7 1860.44 2111.55 1820.75 1863.39 1118.22 1457.74 1854.4 2021.76 1296.09 1473.34 989.131 1544.62 761.2250758_MZ Troxerutin Un 1.0 None None None None Troxerutin is a rutoside, a naturally occurring flavonoid. Flavonoids are polyphenolic compounds that are present in most fruits and vegetables. Although flavonoids are devoid of classical nutritional value, they are increasingly viewed as beneficial dietary components that act as potential protectors against human diseases such as coronary heart disease, cancers, and inflammatory bowel disease. Troxerutin is a beneficial cofactor in coumarin preparations used for the therapy of chronic venous insufficiency, since has hepatoprotective properties and thus protects the liver from a possible lipid peroxidation caused by coumarin. Oxidative stress might be involved in the upregulation of retinal vascular endothelial growth factor (VEGF) during early diabetes, and it is likely that troxerutin has comparatively effective antioxidant properties; therefore, troxerutin might be a useful treatment for attenuating diabetic retinopathy. Troxerutin offers protection against gamma-radiation-induced micronuclei formation and DNA strand breaks and enhances repair of radiation-induced DNA strand breaks, in addition to anti-erythrocytic, anti-thrombic, fibrinolytic and oedema-protective rheological activity. (PMID: 15601310, 15693708, 16294503, 16311905). C33H42O19 None None None 768.956 576.699 1105.27 2381.88 1149.72 646.463 874.552 400.347 755.37 1258.25 681.731 822.98 957.523 1480.64 967.679 1004.22 1638.73 731.131 1380.25 855.282 1046.12 871.169 1143.89 832.005 1677.25 602.761 1892.93 896.628 1197.81 1336.76 982.508 1083.23 1047.06 765.079 1311.29 805.309 893.573 945.945 805.614 1024.22 2780.29 1990.9 762.5070961_MZ Phosphatidylethanolamine (16:0/22:6(4Z_7Z_10Z_13Z_16Z_19Z)) Un 1.0 None None None None C43H74NO8P None None None 1866330.0 3010130.0 1875470.0 2826440.0 2602980.0 1223980.0 3092040.0 3254240.0 2957980.0 1730740.0 3481030.0 3253850.0 2506310.0 1976580.0 1700590.0 1754400.0 3706470.0 2431270.0 2001520.0 3491410.0 1530190.0 1656660.0 2324540.0 1622280.0 2345210.0 2285660.0 1447880.0 3294930.0 1380500.0 1512980.0 2624720.0 2200180.0 2193840.0 2209560.0 1015510.0 1709810.0 2317160.0 2206780.0 1866710.0 2089450.0 2401890.0 2153150.0 764.5214527_MZ Phosphatidylcholine (15:0/20:5(5Z_8Z_11Z_14Z_17Z)) Un 1.0 None None None None C43H76NO8P None None None 1137480.0 1185450.0 976398.0 1219790.0 1495510.0 674929.0 1667180.0 1683910.0 1706780.0 815350.0 1711980.0 1716540.0 1333680.0 1269100.0 838557.0 899926.0 1506630.0 1453350.0 936666.0 1615990.0 1060620.0 1069950.0 1415300.0 1009550.0 1252730.0 1486140.0 881257.0 1752640.0 984891.0 765097.0 1369220.0 1211880.0 1452320.0 1057140.0 827255.0 1336480.0 1301210.0 1213140.0 807502.0 1113610.0 1352040.0 1382570.0 766.1041507_MZ Coenzyme A Un 1.0 None None None None Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme, notable for its role in the synthesis and oxidization of fatty acids, and the oxidation of pyruvate in the citric acid cycle. It is adapted from beta-mercaptoethylamine, panthothenate and adenosine triphosphate. Coenzyme A is synthesized in a five-step process from pantothenate and cysteine. In the first step Pantothenate (vitamin B5) is phosphorylated to 4'-phosphopantothenate by the enzyme pantothenate kinase (PanK; CoaA; CoaX)In the second step, a cysteine is added to 4'-phosphopantothenate by the enzyme phosphopantothenoylcysteine synthetase (PPC-DC; CoaB) to form 4'-phospho-N-pantothenoylcysteine (PPC). In the third step, PPC is decarboxylated to 4'-phosphopantetheine by phosphopantothenoylcysteine decarboxylase (CoaC). In the fourth step, 4'-phosphopantetheine is adenylylated to form dephospho-CoA by the enzyme phosphopantetheine adenylyl transferase (CoaD)Finally, dephospho-CoA is phosphorylated using ATP to coenzyme A by the enzyme dephosphocoenzyme A kinase (CoaE). Since coenzyme A is, in chemical terms, a thiol, it can react with carboxylic acids to form thioesters, thus functioning as an acyl group carrier. CoA assists in transferring fatty acids from the cytoplasm to mitochondria. A molecule of coenzyme A carrying an acetyl group is also referred to as acetyl-CoA. When it is not attached to an acyl group, it is usually referred to as 'CoASH' or 'HSCoA'. Coenzyme A is also the source of the phosphopantetheine group that is added as a prosthetic group to proteins such as acyl carrier protein and formyltetrahydrofolate dehydrogenase Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA, which is a vital component in cholesterol and ketone synthesis. Furthermore, it contributes an acetyl group to choline to produce acetylcholine, in a reaction catalysed by choline acetyltransferase. Its main task is conveying the carbon atoms within the acetyl group to the citric acid cycle to be oxidized for energy production. -- Wikipedia. C21H36N7O16P3S None None None 33495.5 30341.0 50658.4 29576.9 123902.0 45367.5 97978.6 54972.5 50658.7 33516.6 34767.1 7849.2 116068.0 19164.4 65123.3 79768.8 70357.0 84113.2 78786.0 70963.8 41622.5 5846.78 59947.7 22855.0 107365.0 17111.6 125143.0 37712.2 8981.78 20010.2 89952.6 50779.7 25850.5 37735.7 5357.32 21617.5 27275.2 11634.9 35351.0 31562.8 113051.0 56869.2 766.5383382_MZ Phosphatidylcholine (15:0/20:4(5Z_8Z_11Z_14Z)) Un 1.0 None None None None C43H78NO8P None None None 3445940.0 2785420.0 2916340.0 2267750.0 2027440.0 2372570.0 4191610.0 2389400.0 2386070.0 2275460.0 2978440.0 3431690.0 2830000.0 2088010.0 1717420.0 1763350.0 2846280.0 4294060.0 1780940.0 3517810.0 2961330.0 1528030.0 3024900.0 1996000.0 3146880.0 2246800.0 2182510.0 3427970.0 2323900.0 2590400.0 3951980.0 2564050.0 2951370.0 1918670.0 1801190.0 2002860.0 2018460.0 2803790.0 2860100.0 2337540.0 3344590.0 2922840.0 767.5012634_MZ Azythromycin Un 1.0 None None None None Azithromycin is an azalide, a subclass of macrolide antibiotics. Azithromycin is derived from erythromycin; however, it differs chemically from erythromycin in that a methyl-substituted nitrogen atom is incorporated into the lactone ring, thus making the lactone ring 15-membered. Azithromycin is sold under the brand names Zithromax (Zmax) and Sumamed, and is one of the world's best-selling antibiotics. Azithromycin is used to treat certain bacterial infections, most often bacteria causing middle ear infections, tonsillitis, throat infections, laryngitis, bronchitis, pneumonia and sinusitis. It is also effective against certain sexually transmitted infectious diseases, such as non-gonococcal urethritis and cervicitis. C38H72N2O12 None None None 51752.2 18005.8 16604.2 22607.3 33564.5 22598.8 24446.4 16421.7 17690.7 19523.8 24024.4 22609.1 17469.0 32263.3 15580.2 16039.2 19650.0 21738.8 13442.1 154994.0 18510.1 12412.2 23331.4 15805.8 22551.9 23100.4 16720.3 21252.2 12934.5 38386.4 100495.0 49717.8 16344.9 42222.7 11919.4 21390.9 12088.7 90595.5 12476.7 16556.1 183727.0 16599.6 769.5012716_MZ Phosphatidylglycerol16:0/20:4(5Z_8Z_11Z_14Z)) Un 1.0 None None None None PG(16:0/20:4(5Z,8Z,11Z,14Z)) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PG(16:0/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of arachidonic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the arachidonic acid moiety is derived from animal fats and eggs. Phosphatidylglycerol is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of phosphatidylglycerol increases during fetal development. Phosphatidylglycerol may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. C42H75O10P None None None 63476.1 41655.6 39081.1 105179.0 71575.9 27540.8 59510.4 58967.7 69017.9 44989.9 60896.6 95005.8 30007.1 68756.8 62291.9 27904.9 58999.5 55287.9 34362.2 52365.7 43459.7 44519.9 76106.8 44764.0 52424.8 110649.0 78440.2 79759.5 31514.8 40972.8 88363.5 50471.4 38528.2 33648.3 42705.1 46430.0 36170.1 48699.9 29343.4 42195.6 39230.0 56364.1 770.5645978_MZ Phosphatidylcholine (15:0/20:2(11Z_14Z)) Un 1.0 None None None None PC(15:0/20:2(11Z,14Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(15:0/20:2(11Z,14Z)), in particular, consists of one chain of pentadecanoic acid at the C-1 position and one chain of eicosadienoic acid at the C-2 position. The pentadecanoic acid moiety is derived from dairy products and milk fat, while the eicosadienoic acid moiety is derived from fish oils and liver. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C43H82NO8P None None None 233213.0 193480.0 202790.0 159488.0 150343.0 170943.0 217335.0 156524.0 178498.0 131044.0 219474.0 239355.0 194928.0 188797.0 117276.0 188306.0 197568.0 275238.0 154110.0 195801.0 194900.0 149029.0 190496.0 173112.0 189195.0 179470.0 155506.0 226724.0 176593.0 182962.0 227627.0 128665.0 181348.0 168109.0 131094.0 190526.0 170011.0 153380.0 123768.0 136074.0 231685.0 144854.0 770.6028041_MZ Phosphatidylcholine (18:0/P-18:1(11Z)) Un 1.0 None None None None C44H86NO7P None None None 33501.4 29484.6 28557.3 25597.4 21934.3 23553.3 35492.6 26210.9 27392.2 19886.2 34092.6 35305.8 29532.9 29621.3 18096.2 30995.4 28441.4 40364.8 22595.2 31720.3 30213.8 22115.9 28343.3 24680.6 26140.6 27132.4 23638.8 35139.6 23431.8 27688.6 32041.8 23375.5 27206.7 29476.4 18976.2 27018.5 26097.2 29028.7 18378.9 21169.8 34868.8 20610.0 771.5174267_MZ Phosphatidylglycerol16:0/20:3(5Z_8Z_11Z)) Un 1.0 None None None None PG(16:0/20:3(5Z,8Z,11Z)) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PG(16:0/20:3(5Z,8Z,11Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of mead acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the mead acid moiety is derived from fish oils, liver and kidney. Phosphatidylglycerol is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of phosphatidylglycerol increases during fetal development. Phosphatidylglycerol may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. C42H77O10P None None None 144080.0 70245.6 94607.0 130310.0 210220.0 54414.0 112458.0 110840.0 118707.0 72357.9 116817.0 166541.0 66967.5 160961.0 127853.0 63754.0 76444.7 116142.0 61466.6 85841.4 82302.7 103746.0 122078.0 87382.6 99767.5 301795.0 122954.0 124735.0 64527.2 65740.8 124823.0 104165.0 97229.9 57325.5 62155.9 92474.4 76691.5 76604.6 60281.7 71058.0 60746.4 148607.0 772.5618055_MZ Phosphatidylethanolamine (20:2(11Z_14Z)/P-18:1(11Z)) Un 1.0 None None None None PE(20:2(11Z,14Z)/P-18:1(11Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(20:2(11Z,14Z)/P-18:1(11Z)), in particular, consists of one chain of eicosadienoic acid at the C-1 position and one chain of plasmalogen 18:1n7 at the C-2 position. The eicosadienoic acid moiety is derived from fish oils and liver, while the plasmalogen 18:1n7 moiety is derived from animal fats, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. C43H80NO7P None None None 69104.0 58251.9 50298.1 55983.5 73685.7 48255.1 66314.6 94365.3 57397.3 50220.9 79635.0 82157.2 75432.9 109286.0 50896.3 46439.2 73686.3 72468.6 45427.4 63157.1 51657.8 43607.7 68461.6 50688.8 56457.9 72283.7 55571.9 60335.0 40080.7 58385.6 55678.4 42401.9 72589.0 46032.1 31488.7 46334.4 51916.0 67437.2 37464.9 57382.3 56229.3 52322.2 773.3972286_MZ Angiotensin IV Un 1.0 None None None None Angiotensin IV is one of the N-terminal angiotensin degradation products of angiotensin II. Angiotensin IV (AngIV) mediates important physiologic functions in the central nervous system, including blood flow regulation, processes underlying to learning and memory, and presents anticonvulsant activity. The presence of AngIV-specific binding sites has been identified in various mammalian tissues, including blood vessels, heart, kidney, and brain. Besides the presence of AngIV binding sites in the cardiovascular system, the major AngIV synthesizing enzymes aminopeptidase N (APN) and aminopeptidase B (APB) are also expressed in different cell types of this system. AngIV activates several protein kinases, including phosphatidylinositol 3 kinase, PI-dependent kinase-1, extracellular signal-related kinases (ERK), protein kinase B-α/Akt, and p70 ribosomal S6 kinase. AngIV could contribute to vascular damage, increasing the production of monocyte chemoattractant protein-1, the main chemokine involved in monocyte recruitment, and up-regulates the expression of the adhesion molecule intercellular adhesion molecule-1 that is involved in the attachment and transmigration of circulating cells into the damaged tissue. (PMID: 17210474). C40H54N8O8 None None None 2770.29 3511.61 3923.63 3884.29 6626.18 5396.5 5288.99 2573.19 4185.22 3950.14 4868.05 5000.13 1584.9 5231.31 5094.38 4172.81 2718.37 1152.17 2984.57 2525.62 3286.84 3678.1 4226.01 3208.87 3691.08 3535.8 4524.66 2719.07 3022.64 4584.55 3065.81 3176.59 5291.24 2323.34 2961.34 3040.51 3082.2 4038.23 1458.85 4617.67 1819.64 2443.84 773.5307909_MZ Phosphatidylglycerol18:0/18:2(9Z_12Z)) Un 1.0 None None None None PG(18:0/18:2(9Z,12Z)) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PG(18:0/18:2(9Z,12Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of linoleic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the linoleic acid moiety is derived from seed oils. Phosphatidylglycerol is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of phosphatidylglycerol increases during fetal development. Phosphatidylglycerol may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. C42H79O10P None None None 233027.0 137695.0 154574.0 126782.0 340811.0 113550.0 163276.0 205130.0 143332.0 111789.0 180190.0 208014.0 102511.0 207141.0 158413.0 91540.3 100773.0 232600.0 81436.9 176154.0 130970.0 161565.0 163506.0 143369.0 147964.0 403725.0 137076.0 192518.0 120883.0 125668.0 175361.0 154042.0 181626.0 86147.5 90024.6 117973.0 125445.0 127801.0 107224.0 95481.0 100137.0 233185.0 774.5420093_MZ Phosphatidylethanolamine (22:5(4Z_7Z_10Z_13Z_16Z)/P-18:1(11Z)) Un 1.0 None None None None PE(22:5(4Z,7Z,10Z,13Z,16Z)/P-18:1(11Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(22:5(4Z,7Z,10Z,13Z,16Z)/P-18:1(11Z)), in particular, consists of one chain of docosapentaenoic acid at the C-1 position and one chain of plasmalogen 18:1n7 at the C-2 position. The docosapentaenoic acid moiety is derived from animal fats and brain, while the plasmalogen 18:1n7 moiety is derived from animal fats, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. C45H78NO7P None None None 157865.0 127161.0 117615.0 137059.0 185884.0 83304.2 136037.0 158797.0 140189.0 92227.5 152876.0 179294.0 81414.6 147730.0 110614.0 85029.7 125142.0 147826.0 81845.0 128152.0 105597.0 112417.0 132846.0 102332.0 123834.0 206635.0 115091.0 150718.0 93345.6 115917.0 135194.0 100709.0 137274.0 97242.2 79423.6 100689.0 107106.0 111849.0 82797.4 92275.3 93493.5 137434.0 774.6272323_MZ Galactosylceramide (d18:1/20:0) Un 1.0 None None None None Galactosylceramides (GalCer) are non-acidic monoglycosphingolipids, i.e. a sphingolipid with one carbohydrate moiety attached to a ceramide unit. They are an intermediate in sphingolipid metabolism and is the second to last step in the synthesis of digalactosylceramidesulfate. GalCer is generated from ceramide via the enzyme UDP-galactose ceramide galactosyltransferase [EC:2.4.1.47]. It can be converted to digalactosylceramide via the enzyme glycosyltransferases [EC 2.4.1.-]. Galactosylceramide is the principal glycosphingolipid in brain tissue, hence the trivial name cerebroside, which was first conferred on it in 1874. Galactosylceramides are found in all nervous tissues, but they can amount to 2% of the dry weight of grey matter and 12% of white matter. They are major constituents of oligodendrocytes. Synthesis of galactosylceramide takes place on the lumenal surface of the endoplasmic reticulum, although it has free access to the cytosolic surface by an energy-independent flip-flop process. GalCer sits in the extracellular leaflet of cell membranes in nanometer sized domains or rafts. The local clustering of GalCer within rafts is thought to facilitate the initial adhesion of certain viruses, including HIV-1 and bacteria to cells through multivalent interactions between receptor proteins and GalCer. A defect in the degradation of cerbrosides leads to a disorder called Krabbe disease. Krabbe disease (also known as globoid cell leukodystrophy or galactosylceramide lipidosis) is a rare, often fatal degenerative disorder that affects the myelin sheath of the nervous system. Krabbe disease is caused by mutations in the GALC gene, which causes a deficiency of galactosylceramidase. Infants with Krabbe disease are normal at birth. Symptoms begin between the ages of 3 and 6 months with irritability, fevers, limb stiffness, seizures, feeding difficulties, vomiting, and slowing of mental and motor development. There are also juvenile- and adult-onset cases of Krabbe disease, which have similar symptoms but slower progression. In infants, the disease is generally fatal before age 2. Patients with late-onset Krabbe disease tend to have a slower progression of the disease and live significantly longer.Cerebrosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Cerebrosides have a single sugar group linked to ceramide. The most common are galactocerebrosides (containing galactose), the least common are glucocerebrosides (containing glucose). Galactocerebrosides are found predominantly in neuronal cell membranes. In contrast glucocerebrosides are not normally found in membranes. Instead, they are typically intermediates in the synthesis or degradation of more complex glycosphingolipids. Galactocerebrosides are synthesized from ceramide and UDP-galactose. Excess lysosomal accumulation of glucocerebrosides is found in Gaucher disease. C44H85NO8 None None None 6371.22 6689.37 3803.53 5213.22 6125.35 4097.55 6981.56 5765.65 4898.24 3454.84 6239.32 6094.75 4801.9 5748.54 4377.01 4234.06 5848.71 5359.47 3567.69 5444.93 4857.39 3474.78 5078.81 4786.23 4327.96 5818.74 4516.76 5370.45 2969.94 4949.51 5284.31 4353.88 4392.48 3860.92 2735.58 3671.16 3488.82 4622.9 3296.84 3801.85 9084.88 4198.71 775.2192116_MZ Hyaluronan Un 1.0 None None None None Etiocholanolone glucuronide is a natural human metabolite of etiocholanolone generated in the liver by UDP glucuonyltransferase. Etiocholanolone (or 5-isoandrosterone) is a metabolite of testosterone. Classified a ketosteroid, it causes fever, immunostimulation and leukocytosis. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys. C28H44N2O23 None None None 694.735 910.284 748.736 310.506 550.658 763.641 654.917 596.383 369.411 778.39 663.905 791.024 596.107 532.05 593.748 186.028 609.006 340.702 905.685 368.552 659.003 707.703 437.12 1150.55 735.078 569.623 837.902 445.033 1217.41 761.532 510.538 541.84 1163.25 711.4 1043.23 1324.28 853.931 338.682 415.7 792.57 868.125 772.952 776.5251612_MZ Phosphatidylcholine (14:0/22:6(4Z_7Z_10Z_13Z_16Z_19Z)) Un 1.0 None None None None C44H76NO8P None None None 27253.4 37746.2 25371.8 44093.7 35471.7 23163.0 40380.9 36796.1 35600.5 27393.5 36617.1 47124.1 35811.2 25537.2 23105.6 27557.2 38477.1 25301.4 22172.3 58304.7 24739.0 23598.7 32430.1 23414.1 37180.8 33459.6 22519.3 43410.5 21430.6 25989.1 34687.4 38858.3 28504.3 28946.6 16481.4 29199.9 26762.1 78232.8 19165.3 24712.3 22352.0 25002.4 776.5593515_MZ Phosphatidylethanolamine (22:4(7Z_10Z_13Z_16Z)/P-18:1(11Z)) Un 1.0 None None None None C45H80NO7P None None None 642440.0 932636.0 682802.0 963568.0 562702.0 458079.0 769361.0 754256.0 864460.0 625446.0 1029240.0 1335600.0 440182.0 685405.0 489374.0 469544.0 994503.0 650088.0 501328.0 662186.0 711014.0 585574.0 768144.0 505010.0 748371.0 684947.0 651195.0 999015.0 648390.0 683584.0 825318.0 415329.0 744511.0 612825.0 526299.0 634006.0 640579.0 701804.0 434300.0 562330.0 474840.0 542999.0 778.4796394_MZ Phosphatidylethanolamine (18:3(6Z_9Z_12Z)/20:5(5Z_8Z_11Z_14Z_17Z)) Un 1.0 None None None None PE(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)), in particular, consists of one chain of g-linolenic acid at the C-1 position and one chain of eicosapentaenoic acid at the C-2 position. The g-linolenic acid moiety is derived from animal fats, while the eicosapentaenoic acid moiety is derived from fish oils, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. C43H70NO8P None None None 7020.59 9808.03 8435.19 10616.1 12251.7 9581.37 9711.92 7733.54 11705.6 7965.71 12832.5 13618.5 4728.26 10726.2 9085.96 8869.84 8542.14 4689.21 7144.09 7088.41 8470.45 9672.29 10770.7 7811.13 10331.1 9863.66 10700.2 10672.6 7135.07 9115.46 8616.94 7993.18 9721.98 7006.87 7464.33 6921.58 7864.25 10428.5 4109.43 8377.83 5628.52 5903.6 778.5380630_MZ Phosphatidylcholine (14:0/22:5(4Z_7Z_10Z_13Z_16Z)) Un 1.0 None None None None C44H78NO8P None None None 19623.6 19560.1 18032.4 23130.9 27472.5 15854.8 24324.9 23270.1 24610.8 15880.0 26081.3 26917.0 25565.9 21725.7 14364.2 15915.7 22000.1 21605.7 13851.7 30290.6 16957.0 17373.7 23130.5 16135.9 24335.6 24358.4 16574.7 24372.8 16721.8 17614.6 19894.2 21962.8 22334.9 17523.5 13809.9 21150.9 17502.5 34091.5 12060.6 17888.0 17965.8 17559.8 778.5739014_MZ Phosphatidylethanolamine (22:4(7Z_10Z_13Z_16Z)/P-18:0) Un 1.0 None None None None C45H82NO7P None None None 342314.0 368372.0 332941.0 352301.0 339020.0 218406.0 349950.0 411421.0 362011.0 240552.0 429555.0 568873.0 268475.0 394862.0 265082.0 213910.0 263061.0 450758.0 217018.0 407386.0 299121.0 266869.0 290482.0 281694.0 320374.0 399047.0 267625.0 368920.0 266869.0 251908.0 312245.0 215199.0 383947.0 278576.0 190926.0 254041.0 324951.0 284158.0 262334.0 239316.0 266295.0 309939.0 779.4440284_MZ Digoxin Un 1.0 None None None None Digoxin is a cardiac glycoside extracted from the foxglove plant, digitalis. It is widely used in the treatment of various heart conditions, namely atrial fibrillation, atrial flutter and congestive heart failure that cannot be controlled by other medication. Digoxin preparations are commonly marketed under the trade name Lanoxin. Digoxin has positive inotropic and negative chronotropic activity. It is used to control ventricular rate in atrial fibrillation and in the management of congestive heart failure with atrial fibrillation. Its use in congestive heart failure and sinus rhythm is less certain. The margin between toxic and therapeutic doses is small. (From Martindale, The Extra Pharmacopoeia, 30th ed, p666) -- Pubchem; Digoxin is a cardiotonic glycoside obtained mainly from Digitalis lanata; It consists of three sugars and the aglycone digoxigenin. Digoxin binds to a site on the extracellular aspect of the of the Na+/K+ ATPase pump in the membranes of heart cells (myocytes). This causes an increase in the level of sodium ions in the myocytes, which then leads to a rise in the level of calcium ions. The proposed mechanism is the following: inhibition of the Na+/K+ pump leads to increased Na+ levels, which in turn slows down the extrusion of Ca2+ via the Na+/Ca2+ exchange pump. Increased amounts of Ca2+ are then stored in the sarcoplasmic reticulum and released by each action potential, which is unchanged by digoxin. This is a different mechanism from that of catecholamines. -- Wikipedia; Owing to its narrow therapeutic index (the margin between effectiveness and toxicity), side effects of digoxin are inevitable. Nausea, vomiting and GIT upset are common, especially in higher doses. Decreased conduction in the AV node can lead to AV blocks, increased intracellular Ca2+ causes a type of arrhythmia called bigeminy (coupled beats), eventually ventricular tachycardia or fibrillation. An often described but rarely seen side effect of digoxin is a disturbance of color vision (mostly yellow and green color) called xanthopsia. C41H64O14 None None None 3281.12 3590.86 3868.03 4152.27 5765.99 4914.81 5074.67 3545.33 4081.19 4001.49 5643.39 4825.69 2867.08 4736.27 4372.7 5133.68 3110.68 3499.92 2719.64 3360.36 3471.33 3781.64 4393.48 3189.16 3834.69 4300.86 4128.06 4051.33 3596.11 4035.96 3694.11 4387.36 4831.8 2975.95 3230.76 3415.81 3219.55 4646.64 2330.92 4214.75 3021.32 2827.79 780.5145160_MZ Phosphatidylserine (16:0/18:1(9Z)) Un 1.0 None None None None PS(16:0/18:1(9Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PS(16:0/18:1(9Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of oleic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE. C40H76NO10P None None None 20100.8 24079.1 24374.0 25275.9 30510.8 24399.8 30983.1 21815.9 29124.1 22412.9 34382.1 32576.4 12527.2 27494.6 21385.6 21100.2 23407.5 12164.8 17010.9 19746.5 21466.1 21124.0 28654.2 19192.1 25686.2 25907.0 25017.8 24580.4 17659.5 24132.4 24127.1 22436.1 27071.9 17838.9 17134.1 18338.1 20109.7 29083.1 12340.1 22880.7 14041.0 17563.5 780.5524860_MZ Phosphatidylcholine (14:0/22:4(7Z_10Z_13Z_16Z)) Un 1.0 None None None None C44H80NO8P None None None 66073.9 60390.6 56112.1 50972.1 54755.3 46024.6 77409.4 63482.5 67711.6 48817.0 73220.2 77509.3 55846.2 55134.5 39317.9 43192.2 77110.4 71567.6 38625.8 68022.5 58488.3 47030.8 75317.7 44743.5 61198.7 54253.2 46297.4 78303.6 54130.9 56262.5 65625.8 46461.2 73956.4 49399.7 36596.5 56285.4 50744.3 72874.9 44921.6 56909.5 52213.6 57966.9 782.4974991_MZ Phosphatidylserine (16:0/20:4(5Z_8Z_11Z_14Z)) Un 1.0 None None None None PS(16:0/20:4(5Z,8Z,11Z,14Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PS(16:0/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of arachidonic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the arachidonic acid moiety is derived from animal fats and eggs. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE. C42H74NO10P None None None 93336.7 76058.1 69947.5 87265.7 100507.0 47999.6 102271.0 108924.0 88366.1 56011.8 91726.3 108250.0 71962.0 101328.0 57405.8 52770.2 121596.0 87144.1 45985.6 83836.5 82537.0 46151.4 76996.2 75361.8 79477.1 90347.7 67718.6 107529.0 50706.8 64253.2 102959.0 73988.7 82302.5 60921.7 47741.6 74899.0 85476.4 65516.7 58433.8 60151.4 71672.3 92082.8 784.5056162_MZ Phosphatidylserine (16:0/20:3(8Z_11Z_14Z)) Un 1.0 None None None None PS(16:0/20:3(8Z,11Z,14Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PS(16:0/20:3(8Z,11Z,14Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of homo-g-linolenic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the homo-g-linolenic acid moiety is derived from fish oils, liver and kidney. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE. C42H76NO10P None None None 19637.4 19343.8 17588.4 21232.5 23207.8 16169.2 22322.1 21143.4 20519.8 15366.8 23014.9 28174.4 13872.9 26621.4 15926.6 15634.6 25496.4 15779.8 12727.5 18760.9 20057.5 15192.9 20917.3 17331.0 19699.8 22004.4 19088.7 24264.3 14164.6 19998.6 22771.5 16976.3 19876.7 16256.5 13392.9 16600.3 18773.3 18404.5 11056.7 16321.9 14693.9 17759.3 784.5637461_MZ Phosphatidylcholine (18:3(6Z_9Z_12Z)/P-18:1(11Z)) Un 1.0 None None None None C44H80NO7P None None None 13251.3 13566.7 12427.4 12342.6 12596.1 10550.1 13938.1 13535.0 13292.1 9545.48 14766.8 17447.2 8784.6 14392.8 11120.7 10069.8 11724.2 11747.9 8766.99 12269.9 12156.8 10564.3 12992.1 10811.9 12429.3 12545.7 12442.5 13551.1 10135.3 12429.0 11777.6 8307.08 12615.8 11284.1 8861.06 10024.8 11588.5 11992.1 8336.77 9943.17 8238.21 10118.5 785.6517620_MZ Sphingomyelin with formula C45H91N2O6P Un 1.0 None None None None Sphingomyelin (d18:0/22:1(13Z)) or SM(d18:0/22:1(13Z)) is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons. It usually consists of phosphorylcholine and ceramide. In humans, sphingomyelin is the only membrane phospholipid not derived from glycerol. Like all sphingolipids, SPH has a ceramide core (sphingosine bonded to a fatty acid via an amide linkage). In addition it contains one polar head group, which is either phosphocholine or phosphoethanolamine. The plasma membrane of cells is highly enriched in sphingomyelin and is considered largely to be found in the exoplasmic leaflet of the cell membrane. However, there is some evidence that there may also be a sphingomyelin pool in the inner leaflet of the membrane. Moreover, neutral sphingomyelinase-2 - an enzyme that breaks down sphingomyelin into ceramide has been found to localise exclusively to the inner leaflet further suggesting that there may be sphingomyelin present there. Sphingomyelin can accumulate in a rare hereditary disease called Niemann-Pick Disease, types A and B. Niemann-Pick disease is a genetically-inherited disease caused by a deficiency in the enzyme Sphingomyelinase, which causes the accumulation of Sphingomyelin in spleen, liver, lungs, bone marrow, and the brain, causing irreversible neurological damage. SMs play a role in signal transduction. Sphingomyelins are synthesized by the transfer of phosphorylcholine from phosphatidylcholine to a ceramide in a reaction catalyzed by sphingomyelin synthase. C45H91N2O6P None None None 3706.85 5635.54 3501.79 4733.81 3488.15 3463.18 6279.04 3531.59 5093.23 2829.53 4291.6 7835.07 3675.86 3663.8 3908.01 3029.56 6784.02 3388.16 3630.21 4467.62 4054.2 3227.25 4746.66 3789.52 4667.06 4237.24 4192.69 4659.92 2073.94 3860.28 5118.34 3748.79 4360.12 3725.35 1458.69 2458.9 3742.95 5292.01 2620.89 3488.96 2727.66 2723.2 786.5083248_MZ Phosphatidylethanolamine (18:2(9Z_12Z)/22:6(4Z_7Z_10Z_13Z_16Z_19Z)) Un 1.0 None None None None PE(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of linoleic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The linoleic acid moiety is derived from seed oils, while the docosahexaenoic acid moiety is derived from fish oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. C45H74NO8P None None None 35655.8 38839.9 29289.2 42260.9 40146.4 31712.3 48608.7 43579.7 44768.4 34374.1 48223.5 64506.5 33015.2 44324.0 24665.0 30705.0 69430.8 30393.2 27292.8 37599.6 41096.8 34514.1 58990.4 34351.2 46770.6 49540.2 30233.2 56302.1 38647.5 49021.8 43786.3 33593.7 34117.7 45957.4 29070.6 43805.2 38658.2 46288.3 19574.0 33712.8 33207.9 30205.7 786.6519378_MZ Phosphatidylethanolamine (22:0/P-18:0) Un 1.0 None None None None PE(22:0/P-18:0) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(22:0/P-18:0), in particular, consists of one chain of behenic acid at the C-1 position and one chain of plasmalogen 18:0 at the C-2 position. The behenic acid moiety is derived from groundnut oil, while the plasmalogen 18:0 moiety is derived from animal fats, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. C45H90NO7P None None None 2335.6 3237.54 2052.04 3117.34 2076.82 1985.4 3540.4 2397.68 2718.32 1698.99 2508.36 4173.26 2232.03 2281.58 2232.17 2607.08 3494.7 1762.2 1936.85 2406.97 2346.77 1750.87 2766.87 2150.34 2815.92 2626.89 2269.06 2915.0 1368.6 2208.84 3342.01 4120.99 2313.38 2395.77 1204.34 1719.88 2224.67 2789.2 1684.41 1827.91 1705.81 1725.38 787.7233294_MZ Diglyceride with formula C51H96O5 Un 1.0 None None None None DG(24:1(15Z)/24:1(15Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(24:1(15Z)/24:1(15Z)/0:0), in particular, consists of two chains of nervonic acid at the C-1 and C-2 positions. The nervonic acid moieties are derived from fish oils. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position. C51H96O5 None None None 173.594 238.496 426.699 34.3714 143.762 99.8194 151.63 241.72 115.151 391.149 154.4 333.139 486.627 245.342 77.6084 146.884 436.228 1634.77 96.8392 100.342 6.32984 91.1486 102.012 468.476 1642.18 405.499 141.837 213.766 189.612 46.3098 788.5230645_MZ Phosphatidylethanolamine (18:1(11Z)/22:6(4Z_7Z_10Z_13Z_16Z_19Z)) Un 1.0 None None None None C45H76NO8P None None None 411720.0 583218.0 378172.0 662609.0 825426.0 261423.0 738684.0 945283.0 853641.0 457524.0 887416.0 892831.0 772050.0 504051.0 402265.0 382449.0 737866.0 566112.0 428609.0 820789.0 365784.0 578207.0 610154.0 420151.0 580814.0 924809.0 339524.0 778685.0 501581.0 291433.0 580521.0 576232.0 722278.0 614706.0 331293.0 613244.0 648407.0 666490.0 335522.0 599907.0 670933.0 653295.0 788.5969433_MZ Phosphatidylcholine (18:1(11Z)/P-18:1(11Z)) Un 1.0 None None None None PC(18:1(11Z)/P-18:1(11Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(18:1(11Z)/P-18:1(11Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of plasmalogen 18:1n7 at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the plasmalogen 18:1n7 moiety is derived from animal fats, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. C44H84NO7P None None None 11593.1 17217.9 10178.3 17681.8 24567.7 7730.69 23593.8 29487.1 26631.9 11301.4 26695.0 30290.5 21299.6 17837.0 13631.8 13040.1 18076.9 14642.0 9153.72 28528.9 10658.5 15749.6 19478.7 11501.0 15490.0 29766.9 10149.0 25180.4 13500.4 8347.78 18134.9 20440.6 19954.4 20003.9 11075.9 15697.9 18576.4 24171.4 7347.92 15546.9 16717.9 16207.4 789.4800148_MZ Solanesyl-PP Un 1.0 None None None None Solanesyl-PP is involved in steroids biosynthesis pathway. It is a product of solanesyl-diphosphate synthase (KEGG). C45H76O7P2 None None None 4930.78 5199.88 5377.08 6654.94 15177.0 6942.48 7021.34 6133.62 7752.05 6150.5 8691.71 8099.95 6553.27 6376.27 6020.02 6201.95 4964.13 5209.58 4998.26 12134.9 4820.08 6151.21 7089.33 5331.47 6939.32 9979.59 6304.59 6900.77 5337.16 5231.15 6326.56 10036.7 7140.7 4618.5 4981.85 8648.32 5092.51 28898.2 3892.92 6157.31 7030.67 5258.6 790.5389280_MZ Phosphatidylcholine (15:0/22:6(4Z_7Z_10Z_13Z_16Z_19Z)) Un 1.0 None None None None PC(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of pentadecanoic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The pentadecanoic acid moiety is derived from dairy products and milk fat, while the docosahexaenoic acid moiety is derived from fish oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C45H78NO8P None None None 711859.0 1181830.0 701310.0 1080860.0 798196.0 474276.0 1074440.0 1122850.0 939779.0 756789.0 1121680.0 1438040.0 843376.0 582861.0 606625.0 611894.0 1139510.0 994291.0 663191.0 1460610.0 615263.0 568048.0 717812.0 563140.0 773799.0 795213.0 457980.0 1237130.0 590577.0 594958.0 983374.0 757120.0 913468.0 777935.0 370949.0 579584.0 803380.0 825524.0 688718.0 724308.0 876386.0 749166.0 792.5517897_MZ Phosphatidylcholine (15:0/22:5(4Z_7Z_10Z_13Z_16Z)) Un 1.0 None None None None PC(15:0/22:5(4Z,7Z,10Z,13Z,16Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(15:0/22:5(4Z,7Z,10Z,13Z,16Z)), in particular, consists of one chain of pentadecanoic acid at the C-1 position and one chain of docosapentaenoic acid at the C-2 position. The pentadecanoic acid moiety is derived from dairy products and milk fat, while the docosapentaenoic acid moiety is derived from animal fats and brain. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C45H80NO8P None None None 305396.0 361975.0 274980.0 438027.0 339535.0 241502.0 395598.0 429543.0 345399.0 293573.0 395005.0 477138.0 332017.0 323774.0 218699.0 336351.0 381035.0 354339.0 234986.0 424918.0 290333.0 234866.0 343519.0 239053.0 319262.0 320862.0 241748.0 420020.0 264531.0 264182.0 437096.0 362630.0 361885.0 273401.0 210594.0 293489.0 270146.0 319618.0 206096.0 278655.0 322184.0 294029.0 794.6035673_MZ Phosphatidylcholine (20:2(11Z_14Z)/P-18:1(11Z)) Un 1.0 None None None None C46H86NO7P None None None 52738.2 49449.7 47298.8 58058.4 45978.5 39104.4 63795.4 53773.9 50672.4 40887.8 60882.0 58761.0 67456.0 48997.8 33035.1 63671.8 47896.4 81314.1 37367.8 67359.4 40459.4 37053.0 49320.7 37625.4 47554.6 48822.8 36763.2 67706.6 45904.6 41109.9 60418.0 74022.8 54051.6 46075.5 33081.0 42378.9 39038.7 69879.2 41382.2 44490.9 58494.7 40641.1 797.5322478_MZ Phosphatidylglycerol16:0/22:4(7Z_10Z_13Z_16Z)) Un 1.0 None None None None PG(16:0/22:4(7Z,10Z,13Z,16Z)) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PG(16:0/22:4(7Z,10Z,13Z,16Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of adrenic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the adrenic acid moiety is derived from animal fats. Phosphatidylglycerol is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of phosphatidylglycerol increases during fetal development. Phosphatidylglycerol may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. C44H79O10P None None None 69026.7 37209.9 41075.8 50456.7 86252.2 37387.2 49653.4 67819.0 45231.0 40125.8 54922.5 56815.6 41527.7 70713.1 43608.1 38070.2 32817.1 65252.2 27226.5 62076.2 38005.0 40428.6 48739.4 41320.9 48107.0 80556.6 40533.7 57265.6 36787.0 38934.9 54649.0 60838.4 52265.4 27492.1 27920.8 41736.1 35138.0 64042.6 32152.8 33378.3 32924.8 57988.8 797.5691993_MZ Phosphatidylglycerol18:0/18:0) Un 1.0 None None None None PG(18:0/18:0) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PG(18:0/18:0), in particular, consists of one chain of stearic acid at the C-1 position and one chain of stearic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the stearic acid moiety is derived from animal fats, coco butter and sesame oil. Phosphatidylglycerol is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of phosphatidylglycerol increases during fetal development. Phosphatidylglycerol may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. C42H83O10P None None None 479294.0 665622.0 507607.0 704965.0 417206.0 335758.0 555134.0 550413.0 624659.0 487061.0 743211.0 959603.0 343957.0 491784.0 367577.0 336548.0 749049.0 480351.0 391205.0 466499.0 534407.0 447664.0 560766.0 386286.0 557920.0 513293.0 485521.0 709497.0 487739.0 516396.0 565706.0 296723.0 559302.0 457586.0 387335.0 470219.0 475545.0 530384.0 360456.0 431356.0 358360.0 419460.0 800.5228822_MZ Phosphatidylcholine (18:3(6Z_9Z_12Z)/20:5(5Z_8Z_11Z_14Z_17Z)) Un 1.0 None None None None PC(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)), in particular, consists of one chain of g-linolenic acid at the C-1 position and one chain of eicosapentaenoic acid at the C-2 position. The g-linolenic acid moiety is derived from animal fats, while the eicosapentaenoic acid moiety is derived from fish oils, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C46H76NO8P None None None 13206.9 14361.3 14027.5 17948.3 25920.1 16642.8 17276.2 13208.7 16046.3 13386.7 18754.1 21129.2 28412.0 16350.0 12230.6 12550.4 13192.2 12768.6 10210.5 31415.7 13106.8 12598.1 17559.3 11678.3 22221.5 21431.8 14495.8 16607.3 12175.2 15954.5 14994.1 25388.7 17490.8 11577.7 11463.8 20700.9 12038.8 54764.0 8502.55 13399.4 10895.8 11620.1 803.7152634_MZ Tricaprylic glyceride (16:0/14:0/18:1(9Z))[iso6] Un 1.0 None None None None TG(16:0/14:0/18:1(9Z))[iso6] is a monooleic acid triglyceride. Triglycerides (TGs) are also known as triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.e. fatty acid tri-esters of glycerol). TGs may be divided into three general types with respect to their acyl substituents. They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. TG(16:0/14:0/18:1(9Z))[iso6], in particular, consists of one chain of palmitic acid at the C-1 position, one chain of myristic acid at the C-2 position and one chain of oleic acid at the C-3 position. TGs are the main constituent of vegetable oil and animal fats. TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) with the help of lipases and bile secretions, which can then move into blood vessels. The triglycerides are rebuilt in the blood from their fragments and become constituents of lipoproteins, which deliver the fatty acids to and from fat cells among other functions. Various tissues can release the free fatty acids and take them up as a source of energy. Fat cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain cannot utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when it is broken down. (www.cyberlipid.org, www.wikipedia.org)TAGs can serve as fatty acid stores in all cells, but primarily in adipocytes of adipose tissue. The major building block for the synthesis of triacylglycerides, in non-adipose tissue, is glycerol. Adipocytes lack glycerol kinase and so must use another route to TAG synthesis. Specifically, dihydroxyacetone phosphate (DHAP), which is produced during glycolysis, is the precursor for TAG synthesis in adipose tissue. DHAP can also serve as a TAG precursor in non-adipose tissues, but does so to a much lesser extent than glycerol. The use of DHAP for the TAG backbone depends on whether the synthesis of the TAGs occurs in the mitochondria and ER or the ER and the peroxisomes. The ER/mitochondria pathway requires the action of glycerol-3-phosphate dehydrogenase to convert DHAP to glycerol-3-phosphate. Glycerol-3-phosphate acyltransferase then esterifies a fatty acid to glycerol-3-phosphate thereby generating lysophosphatidic acid. The ER/peroxisome reaction pathway uses the peroxisomal enzyme DHAP acyltransferase to acylate DHAP to acyl-DHAP which is then reduced by acyl-DHAP reductase. The fatty acids that are incorporated into TAGs are activated to acyl-CoAs through the action of acyl-CoA synthetases. Two molecules of acyl-CoA are esterified to glycerol-3-phosphate to yield 1,2-diacylglycerol phosphate (also known as phosphatidic acid). The phosphate is then removed by phosphatidic acid phosphatase (PAP1), to generate 1,2-diacylglycerol. This diacylglycerol serves as the substrate for addition of the third fatty acid to make TAG. Intestinal monoacylglycerols, derived from dietary fats, can also serve as substrates for the synthesis of 1,2-diacylglycerols. C51H96O6 None None None 417.046 1060.05 296.905 506.091 181.771 91.3311 213.743 418.213 272.479 417.624 269.427 118.832 517.781 483.268 255.373 557.359 451.287 338.561 259.011 389.647 151.494 90.9405 148.713 317.481 437.502 212.258 193.729 352.861 241.307 176.249 371.617 1416.59 197.16 288.473 257.011 202.947 243.868 169.355 463.086 234.81 1076.42 132.787 804.5527557_MZ Phosphatidylcholine (16:0/22:6(4Z_7Z_10Z_13Z_16Z_19Z)) Un 1.0 None None None None PC(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the docosahexaenoic acid moiety is derived from fish oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C46H80NO8P None None None 52507.0 59109.6 47278.6 54510.1 55940.7 37010.1 65740.8 67865.6 62873.6 46896.7 68892.5 71094.4 61003.7 45289.7 39591.5 39302.7 65690.4 68650.8 35692.5 83333.9 43326.4 41290.1 54027.9 37313.7 58678.4 51962.1 35687.1 70351.2 48971.5 49222.7 56968.8 41096.6 64960.7 48294.4 31667.1 49357.3 48787.0 69568.7 42052.9 46635.1 48582.2 46639.6 804.5897905_MZ Phosphatidylcholine (14:0/22:2(13Z_16Z)) Un 1.0 None None None None C44H84NO8P None None None 347866.0 261577.0 305597.0 213865.0 202439.0 236756.0 311999.0 215089.0 255508.0 179896.0 316728.0 313098.0 302127.0 258059.0 160190.0 239965.0 296047.0 434569.0 220801.0 275611.0 276349.0 216684.0 267427.0 246685.0 265438.0 248232.0 206023.0 326903.0 267918.0 265937.0 301174.0 154375.0 251699.0 242611.0 180190.0 288735.0 248848.0 217018.0 187531.0 192326.0 271021.0 206625.0 805.2577059_MZ Hydroxypropionic porphyrin III Un 1.0 None None None None Hydroxypropionic porphyrin III is a porphyrin isolated only in patients with porphyria cutanea tarda. Porphyria cutanea tarda (PCT) is a metabolic disorder of haeme biosynthesis caused by decreased activity of uroporphyrinogen decarboxylase. Porphyria cutanea tarda is manifest by fragility, erosions, bullae, milia and scars on sun-exposed skin. Excess porphyrins in the skin interact with light of approximately 400 nm-wavelength radiant energy, forming reactive oxygen species. Porphyria cutanea tarda is categorized as familial, acquired or toxic. Factors that may induce clinical expression of PCT in susceptible individuals include alcohol, oestrogen, iron, polyhalogenated compounds and viral infections. Porphyria cutanea tarda is associated with an increased incidence of the haemochromatosis gene. Treatments for PCT include withdrawal of aggravating factors, phlebotomy and oral antimalarial medications. Porphyria cutanea tarda is associated with hepatic iron overload and responds to iron-reduction therapy. Porphyria cutanea tarda is the most common porphyria, followed by acute intermittent porphyria and erythropoietic protoporphyria. The molecular genetics of the porphyrias is very heterogenous. (PMID: 16315139, 7655298, 11105361). C39H38N4O14, Heptacarboxylporphyrin I, Pseudouroporphyrin None None None 38.1471 87.7103 128.357 155.975 156.135 152.518 101.495 81.4894 165.925 267.345 124.542 1324.74 205.209 120.014 153.595 79.3364 103.812 358.867 78.605 146.166 113.47 128.35 379.176 24.8691 153.651 286.612 187.204 252.05 201.668 431.411 216.777 140.567 110.738 30.3877 201.732 22.2573 203.495 122.996 108.183 151.315 805.7134263_MZ Tricaprylic glyceride (16:0/14:0/18:0)[iso6] Un 1.0 None None None None TG(16:0/14:0/18:0)[iso6] is a monostearic acid triglyceride. Triglycerides (TGs) are also known as triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.e. fatty acid tri-esters of glycerol). TGs may be divided into three general types with respect to their acyl substituents. They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. TG(16:0/14:0/18:0)[iso6], in particular, consists of one chain of palmitic acid at the C-1 position, one chain of myristic acid at the C-2 position and one chain of stearic acid at the C-3 position. TGs are the main constituent of vegetable oil and animal fats. TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) with the help of lipases and bile secretions, which can then move into blood vessels. The triglycerides are rebuilt in the blood from their fragments and become constituents of lipoproteins, which deliver the fatty acids to and from fat cells among other functions. Various tissues can release the free fatty acids and take them up as a source of energy. Fat cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain cannot utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when it is broken down. (www.cyberlipid.org, www.wikipedia.org)TAGs can serve as fatty acid stores in all cells, but primarily in adipocytes of adipose tissue. The major building block for the synthesis of triacylglycerides, in non-adipose tissue, is glycerol. Adipocytes lack glycerol kinase and so must use another route to TAG synthesis. Specifically, dihydroxyacetone phosphate (DHAP), which is produced during glycolysis, is the precursor for TAG synthesis in adipose tissue. DHAP can also serve as a TAG precursor in non-adipose tissues, but does so to a much lesser extent than glycerol. The use of DHAP for the TAG backbone depends on whether the synthesis of the TAGs occurs in the mitochondria and ER or the ER and the peroxisomes. The ER/mitochondria pathway requires the action of glycerol-3-phosphate dehydrogenase to convert DHAP to glycerol-3-phosphate. Glycerol-3-phosphate acyltransferase then esterifies a fatty acid to glycerol-3-phosphate thereby generating lysophosphatidic acid. The ER/peroxisome reaction pathway uses the peroxisomal enzyme DHAP acyltransferase to acylate DHAP to acyl-DHAP which is then reduced by acyl-DHAP reductase. The fatty acids that are incorporated into TAGs are activated to acyl-CoAs through the action of acyl-CoA synthetases. Two molecules of acyl-CoA are esterified to glycerol-3-phosphate to yield 1,2-diacylglycerol phosphate (also known as phosphatidic acid). The phosphate is then removed by phosphatidic acid phosphatase (PAP1), to generate 1,2-diacylglycerol. This diacylglycerol serves as the substrate for addition of the third fatty acid to make TAG. Intestinal monoacylglycerols, derived from dietary fats, can also serve as substrates for the synthesis of 1,2-diacylglycerols. C51H98O6 None None None 1116.12 2404.44 1515.69 1691.62 684.799 982.838 1807.36 1252.64 946.331 716.046 1446.78 2525.58 1220.75 849.412 528.389 1591.0 1462.27 1955.89 971.704 2356.9 1055.07 430.327 954.764 1093.57 1296.07 839.36 1225.25 1898.76 821.973 1184.96 1976.6 2490.29 870.729 1682.43 427.739 723.878 886.991 1568.5 1437.03 638.763 1893.24 674.703 806.4977903_MZ Phosphatidylserine (16:0/22:6(4Z_7Z_10Z_13Z_16Z_19Z)) Un 1.0 None None None None C44H74NO10P None None None 77756.9 116676.0 66535.3 98466.6 92505.7 57371.2 113040.0 122665.0 96042.8 60881.5 98728.3 135848.0 70644.4 88418.9 60198.9 64775.8 139797.0 74322.9 60702.3 112035.0 88231.0 69116.2 90575.3 67599.6 91079.8 101861.0 64630.3 120470.0 57102.3 79137.7 121192.0 81123.2 76666.3 84167.0 42098.3 71003.1 98628.9 73384.7 53806.9 67458.2 75958.7 82099.6 808.5146198_MZ Phosphatidylserine (18:1(9Z)/20:4(5Z_8Z_11Z_14Z)) Un 1.0 None None None None PS(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PS(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of oleic acid at the C-1 position and one chain of arachidonic acid at the C-2 position. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the arachidonic acid moiety is derived from animal fats and eggs. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE. C44H76NO10P None None None 69087.7 61514.8 66699.5 70655.3 85462.4 63201.2 82141.7 76228.1 70015.7 62581.4 82490.5 86362.5 75825.8 81285.2 53267.0 54823.1 71983.3 69823.2 48433.7 66417.5 65523.2 54247.3 77048.2 55563.3 76448.5 78897.3 62792.0 76204.9 56660.7 63965.6 83388.0 71163.2 75867.6 53065.8 46634.8 57691.7 59825.3 68362.7 48447.5 62154.9 73938.1 67383.5 808.6669992_MZ Galactosylceramide (d18:1/24:1(15Z)) Un 1.0 None None None None Galactosylceramides (GalCer) are non-acidic monoglycosphingolipids, i.e. a sphingolipid with one carbohydrate moiety attached to a ceramide unit. They are an intermediate in sphingolipid metabolism and is the second to last step in the synthesis of digalactosylceramidesulfate. GalCer is generated from ceramide via the enzyme UDP-galactose ceramide galactosyltransferase [EC:2.4.1.47]. It can be converted to digalactosylceramide via the enzyme glycosyltransferases [EC 2.4.1.-]. Galactosylceramide is the principal glycosphingolipid in brain tissue, hence the trivial name cerebroside, which was first conferred on it in 1874. Galactosylceramides are found in all nervous tissues, but they can amount to 2% of the dry weight of grey matter and 12% of white matter. They are major constituents of oligodendrocytes. Synthesis of galactosylceramide takes place on the lumenal surface of the endoplasmic reticulum, although it has free access to the cytosolic surface by an energy-independent flip-flop process. GalCer sits in the extracellular leaflet of cell membranes in nanometer sized domains or rafts. The local clustering of GalCer within rafts is thought to facilitate the initial adhesion of certain viruses, including HIV-1 and bacteria to cells through multivalent interactions between receptor proteins and GalCer. A defect in the degradation of cerbrosides leads to a disorder called Krabbe disease. Krabbe disease (also known as globoid cell leukodystrophy or galactosylceramide lipidosis) is a rare, often fatal degenerative disorder that affects the myelin sheath of the nervous system. Krabbe disease is caused by mutations in the GALC gene, which causes a deficiency of galactosylceramidase. Infants with Krabbe disease are normal at birth. Symptoms begin between the ages of 3 and 6 months with irritability, fevers, limb stiffness, seizures, feeding difficulties, vomiting, and slowing of mental and motor development. There are also juvenile- and adult-onset cases of Krabbe disease, which have similar symptoms but slower progression. In infants, the disease is generally fatal before age 2. Patients with late-onset Krabbe disease tend to have a slower progression of the disease and live significantly longer.Cerebrosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Cerebrosides have a single sugar group linked to ceramide. The most common are galactocerebrosides (containing galactose), the least common are glucocerebrosides (containing glucose). Galactocerebrosides are found predominantly in neuronal cell membranes. In contrast glucocerebrosides are not normally found in membranes. Instead, they are typically intermediates in the synthesis or degradation of more complex glycosphingolipids. Galactocerebrosides are synthesized from ceramide and UDP-galactose. Excess lysosomal accumulation of glucocerebrosides is found in Gaucher disease. C48H91NO8 None None None 12548.1 3981.53 4805.05 5433.1 9143.65 3644.78 7031.38 12121.5 6363.81 4371.54 9352.45 5627.04 11136.7 16510.8 5151.44 4483.58 8584.66 6379.19 3579.6 5427.66 5487.05 3252.93 7149.81 5674.01 5642.19 7687.12 5115.13 5158.41 3291.94 4981.22 5448.28 5009.4 6051.63 3395.17 3478.58 5012.99 4653.31 5370.58 3720.29 5880.25 17302.6 6131.25 809.5203660_MZ Phosphatidylinositol16:0/16:0) Un 1.0 None None None None PI(16:0/16:0) is a phosphatidylinositol. Phosphatidylinositols are important lipids, both as a key membrane constituent and as a participant in essential metabolic processes, both directly and via a number of metabolites. Phosphatidylinositols are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to inositol (hexahydroxycyclohexane). Phosphatidylinositols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 18 and 20 carbons are the most common. PI(16:0/16:0), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. In most organisms, the stereochemical form of the last is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial. Phosphatidylinositol is especially abundant in brain tissue, where it can amount to 10% of the phospholipids, but it is present in all tissues and cell types. There is usually less of it than of phosphatidylcholine, phosphatidylethanolamine and phosphatidylserine. In animal tissues, phosphatidylinositol is the primary source of the arachidonic acid required for biosynthesis of eicosanoids, including prostaglandins, via the action of the enzyme phospholipase A2. Phosphatidylinositol can be phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated by a specific kinase. Seven different isomers are known, but the most important in both quantitative and biological terms are phosphatidylinositol 4-phosphate and phosphatidylinositol 4,5-bisphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PIs contain almost exclusively stearic acid at carbon 1 and arachidonic acid at carbon 2. PIs composed exclusively of non-phosphorylated inositol exhibit a net charge of -1 at physiological pH. Molecules with phosphorylated inositol (such as PIP, PIP2, PIP3, etc.) are termed polyphosphoinositides. The polyphosphoinositides are important intracellular transducers of signals emanating from the plasma membrane. The synthesis of PI involves CDP-activated 1,2-diacylglycerol condensation with myo-inositol. C41H79O13P None None None 37245.7 31501.3 35149.1 35726.8 43307.4 32743.4 43878.9 37844.8 35486.5 32969.3 40776.9 42404.0 39059.9 41488.2 27621.5 28075.2 36416.3 37623.0 25152.6 35184.8 33804.3 26974.9 39231.8 30047.0 39263.2 39348.1 32682.1 38392.5 29151.9 33808.1 43357.3 36253.7 38397.5 26986.7 23903.7 29483.1 29637.5 34525.1 29724.1 32456.9 39248.9 34886.8 810.4909743_MZ Phosphatidylethanolamine (20:4(5Z_8Z_11Z_14Z)/22:6(4Z_7Z_10Z_13Z_16Z_19Z)) Un 1.0 None None None None PE(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of arachidonic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The arachidonic acid moiety is derived from animal fats and eggs, while the docosahexaenoic acid moiety is derived from fish oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. C47H74NO8P None None None 15661.5 22355.9 23703.9 29977.1 49755.2 27457.7 27017.5 18339.0 32624.4 21860.6 38113.0 37949.1 33733.0 28023.4 25271.2 23536.2 18813.3 9190.83 17253.6 38789.1 19873.8 25231.5 28874.8 21573.6 33184.2 38352.9 23313.7 26305.8 19092.3 22751.8 20106.9 54158.5 27631.3 17926.9 18072.5 22515.2 20814.2 56418.0 10610.0 24283.7 11639.8 14948.8 810.5288321_MZ Phosphatidylserine (18:0/20:4(5Z_8Z_11Z_14Z)) Un 1.0 None None None None PS(18:0/20:4(5Z,8Z,11Z,14Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PS(18:0/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of arachidonic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the arachidonic acid moiety is derived from animal fats and eggs. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE. C44H78NO10P None None None 665386.0 489124.0 600599.0 560373.0 671743.0 364050.0 854185.0 767095.0 546867.0 389842.0 619390.0 681434.0 797820.0 601367.0 434213.0 387932.0 737065.0 817714.0 410958.0 818458.0 513072.0 302410.0 565975.0 509874.0 588355.0 592607.0 427413.0 823120.0 371413.0 405963.0 771346.0 502751.0 601657.0 403276.0 272455.0 430529.0 556175.0 503097.0 567308.0 489049.0 723396.0 609380.0 811.4901965_MZ Phosphatidylglycerol16:1(9Z)/22:6(4Z_7Z_10Z_13Z_16Z_19Z)) Un 1.0 None None None None PG(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PG(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of palmitoleic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The palmitoleic acid moiety is derived from animal fats and vegetable oils, while the docosahexaenoic acid moiety is derived from fish oils. Phosphatidylglycerol is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of phosphatidylglycerol increases during fetal development. Phosphatidylglycerol may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. C44H73O10P None None None 9030.81 11435.6 12181.5 15010.3 25301.7 14464.3 13447.6 10121.3 16357.9 11520.9 19335.7 18977.5 8327.64 14725.3 12671.1 12164.3 9600.78 5189.26 9084.12 23561.1 10409.2 12606.8 14933.8 10917.7 16108.2 18739.1 12438.4 13382.5 9730.93 11672.9 12175.6 25200.9 13921.3 9244.95 9252.44 11057.0 10999.5 30088.0 5043.13 12626.7 7652.85 7347.36 812.6587170_MZ Phosphatidylethanolamine (24:0/P-18:1(11Z)) Un 1.0 None None None None C47H92NO7P None None None 2495.69 4267.55 2789.18 3371.64 2289.86 2548.43 3658.2 2162.05 2801.2 2141.1 3078.38 3843.39 1966.22 2914.35 2308.17 2781.43 3348.08 2764.94 2780.97 3959.42 2661.3 1877.96 3455.28 3106.15 3866.16 2339.65 2661.72 3715.36 1721.31 3287.5 3463.78 4447.83 2561.79 3352.35 1392.77 1789.82 2282.76 3068.97 2520.69 2384.98 2726.82 1933.06 813.3148204_MZ Tricrocin Un 1.0 None None None None Tricrocin is a water soluble crocetin glycoside, a carotenoid pigment of saffron (Crocus sativus L.) that has been used as a spice for flavoring and coloring food preparations, and in Chinese traditional medicine as an anodyne or tranquilizer. Saffron is now used worldwide in folk medicine and is reputed to be useful in treating various human disorders such as heart and blood disorders. Stroke and heart attack are involved in reputed folkloric uses of saffron. Saffron is orally administrated as a decoction. Saffron extract exerts a protective effect on renal ischemia reperfusion induced oxidative damage in rats. (PMID: 17215084). Crocetin esters present in saffron stigmas and in Gardenia jasminoides Ellis fruit are the compounds responsible for their color. (PMID: 16448211). C38H54O19 None None None 231.451 375.727 226.627 229.792 569.662 244.153 421.312 301.98 499.92 324.32 393.06 762.96 228.934 399.918 575.811 380.704 314.248 206.079 300.794 321.632 208.047 218.711 356.13 308.749 358.122 467.155 372.75 283.44 294.562 303.5 350.558 692.415 455.878 319.608 346.25 263.156 202.469 276.62 75.0808 346.095 304.717 211.269 813.5041688_MZ Phosphatidylglycerol16:0/22:6(4Z_7Z_10Z_13Z_16Z_19Z)) Un 1.0 None None None None PG(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PG(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the docosahexaenoic acid moiety is derived from fish oils. Phosphatidylglycerol is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of phosphatidylglycerol increases during fetal development. Phosphatidylglycerol may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. C44H75O10P None None None 13430.1 12748.8 16383.3 14271.7 20940.7 23803.5 20191.5 10845.7 18143.7 15261.1 20003.4 21982.1 10338.2 17520.8 15839.9 17200.7 10954.6 7128.77 13017.6 15550.1 14583.1 13443.1 20902.8 12698.6 17949.0 16155.1 18109.0 14790.5 11663.0 17765.8 16892.7 14323.1 18691.8 9600.62 13122.1 11200.9 11996.6 18502.7 6559.93 14024.5 8693.49 10397.7 814.5654690_MZ Phosphatidylcholine (22:6(4Z_7Z_10Z_13Z_16Z_19Z)/P-18:1(11Z)) Un 1.0 None None None None PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/P-18:1(11Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/P-18:1(11Z)), in particular, consists of one chain of docosahexaenoic acid at the C-1 position and one chain of plasmalogen 18:1n7 at the C-2 position. The docosahexaenoic acid moiety is derived from fish oils, while the plasmalogen 18:1n7 moiety is derived from animal fats, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. C48H82NO7P None None None 23656.6 22703.7 22813.3 20303.9 26903.8 24158.7 28812.6 25393.1 27006.2 20977.1 28882.1 29541.1 20758.9 28543.3 20711.5 21992.2 23599.0 21939.4 17846.3 25766.8 23411.6 23542.8 27790.7 20434.4 23935.5 24954.3 23331.1 28347.7 24212.0 24022.1 21615.0 18745.7 29742.3 21791.8 17894.9 22631.9 20136.3 27462.1 14686.7 22694.2 22203.3 19744.3 814.6598780_MZ Phosphatidylethanolamine (24:0/P-18:0) Un 1.0 None None None None PE(24:0/P-18:0) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(24:0/P-18:0), in particular, consists of one chain of lignoceric acid at the C-1 position and one chain of plasmalogen 18:0 at the C-2 position. The lignoceric acid moiety is derived from groundnut oil, while the plasmalogen 18:0 moiety is derived from animal fats, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. C47H94NO7P None None None 1034.96 954.055 772.783 1306.42 1041.9 747.112 1056.66 990.403 1056.25 888.379 1247.78 1001.49 1014.66 1295.63 700.35 1215.01 1064.32 1170.87 717.236 934.654 707.235 644.867 1122.69 901.307 1428.19 1046.48 1356.51 845.374 692.38 765.58 997.153 1666.1 906.698 970.741 613.57 667.605 894.538 904.089 762.698 735.383 1579.94 679.865 817.5010375_MZ Phosphatidylglycerol18:2(9Z_12Z)/22:6(4Z_7Z_10Z_13Z_16Z_19Z)) Un 1.0 None None None None PG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of linoleic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The linoleic acid moiety is derived from seed oils, while the docosahexaenoic acid moiety is derived from fish oils. Phosphatidylglycerol is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of phosphatidylglycerol increases during fetal development. Phosphatidylglycerol may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. C46H75O10P None None None 101508.0 86452.9 73520.2 127078.0 247671.0 47246.5 127633.0 133578.0 189882.0 93061.6 149047.0 174614.0 114376.0 123538.0 127199.0 60296.4 113169.0 121190.0 83748.6 122362.0 79604.6 124048.0 127449.0 72611.6 145215.0 253235.0 121351.0 168774.0 87169.2 61168.5 175223.0 119984.0 106856.0 62556.5 79648.6 107462.0 91878.8 114128.0 96648.5 89669.2 98335.2 101652.0 819.4506310_MZ Phosphatidylglycerolphosphate (16:0/16:1(9Z)) Un 1.0 None None None None PGP(16:0/16:1(9Z)) is a phosphatidylglycerolphosphate or glycerophospholipid (PGP or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site followed by another phosphate moiety. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PGP(16:0/16:1(9Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of palmitoleic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the palmitoleic acid moiety is derived from animal fats and vegetable oils. Phosphatidylglycerolphosphate is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of Phosphatidylglycerolphosphate increases during fetal development. Phosphatidylglycerolphosphate may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGPs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PGP also serves as a precursor for the synthesis of cardiolipin. PGP is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. C38H74O13P2 None None None 4912.54 5883.81 6375.26 7210.09 11604.6 8157.24 6477.82 5118.39 7490.45 6426.69 9518.06 7897.91 3401.21 7167.83 7081.86 7255.37 4310.97 4430.43 5253.1 5242.6 5142.25 6520.03 6783.51 5002.64 6719.51 7864.95 7154.92 6476.18 5585.19 6098.83 6101.29 6950.28 7945.21 4973.52 5233.94 5464.97 5742.26 8443.76 3761.31 6561.1 3935.13 4726.42 819.5174711_MZ Phosphatidylglycerol18:1(11Z)/22:6(4Z_7Z_10Z_13Z_16Z_19Z)) Un 1.0 None None None None PG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the docosahexaenoic acid moiety is derived from fish oils. Phosphatidylglycerol is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of phosphatidylglycerol increases during fetal development. Phosphatidylglycerol may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. C46H77O10P None None None 220639.0 104084.0 114519.0 155124.0 719369.0 73802.6 165013.0 225729.0 214515.0 129755.0 200060.0 206671.0 194433.0 183825.0 201113.0 93714.4 94409.3 267396.0 100923.0 218574.0 111489.0 210472.0 149310.0 124238.0 189307.0 464451.0 141885.0 220093.0 121454.0 78333.0 209476.0 215221.0 202831.0 88864.3 107692.0 144397.0 141680.0 117047.0 141285.0 107130.0 181170.0 222258.0 821.5294152_MZ Phosphatidylglycerol18:0/22:6(4Z_7Z_10Z_13Z_16Z_19Z)) Un 1.0 None None None None PG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the docosahexaenoic acid moiety is derived from fish oils. Phosphatidylglycerol is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of phosphatidylglycerol increases during fetal development. Phosphatidylglycerol may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. C46H79O10P None None None 96361.2 51058.3 60081.6 65296.9 218775.0 48609.2 74212.9 117473.0 75586.5 60120.5 76598.3 85953.2 72024.8 119113.0 73949.1 49447.2 46132.1 91544.6 39681.4 107313.0 55692.9 75160.1 72874.3 58182.0 70915.9 147844.0 61447.0 89048.5 56144.6 42692.6 72761.9 74873.9 101855.0 38297.5 42998.7 65095.5 54275.8 74241.6 51995.3 48702.9 58042.0 93175.9 824.5212385_MZ Phosphatidylcholine (18:4(6Z_9Z_12Z_15Z)/22:6(4Z_7Z_10Z_13Z_16Z_19Z)) Un 1.0 None None None None PC(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of stearidonic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The stearidonic acid moiety is derived from seed oils, while the docosahexaenoic acid moiety is derived from fish oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C48H76NO8P None None None 21612.5 26982.3 26145.4 40133.4 40269.9 32610.5 29582.2 23552.4 27949.9 31342.3 37530.9 41701.2 26333.4 29194.7 27372.5 36521.7 20478.5 17209.3 19674.1 35430.8 26077.5 24898.9 32990.6 20935.6 35566.0 35012.2 30586.6 30444.4 23834.4 27132.1 32424.7 41304.6 29016.9 20486.2 23897.7 24884.2 20668.0 51506.4 16288.4 27774.4 17448.9 19849.1 825.5627615_MZ Phosphatidylglycerol with formula C46H83O10P Un 1.0 None None None None C46H83O10P None None None 229531.0 210045.0 196813.0 189839.0 217924.0 135617.0 265273.0 291046.0 249881.0 197059.0 265266.0 252790.0 249302.0 180139.0 155568.0 135103.0 246359.0 347572.0 137685.0 326518.0 167055.0 153141.0 212393.0 145531.0 244515.0 202287.0 123121.0 284193.0 215607.0 204249.0 229412.0 137207.0 290471.0 193187.0 116035.0 200842.0 198360.0 235084.0 193367.0 185080.0 235529.0 202673.0 826.5732241_MZ Phosphatidylcholine (16:0/22:5(4Z_7Z_10Z_13Z_16Z)) Un 1.0 None None None None PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of docosapentaenoic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the docosapentaenoic acid moiety is derived from animal fats and brain. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C46H82NO8P None None None 222717.0 160090.0 188976.0 157210.0 283861.0 144444.0 248510.0 275747.0 255015.0 160891.0 245178.0 211721.0 321561.0 235681.0 142385.0 129607.0 212057.0 322413.0 142358.0 249988.0 167862.0 191750.0 218791.0 163852.0 221019.0 253348.0 146061.0 240710.0 221718.0 168259.0 180812.0 126706.0 298587.0 173605.0 136526.0 241973.0 184445.0 229936.0 157597.0 200958.0 250889.0 221473.0 828.4997525_MZ Phosphatidylethanolamine (20:5(5Z_8Z_11Z_14Z_17Z)/22:6(4Z_7Z_10Z_13Z_16Z_19Z)) Un 1.0 None None None None PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of eicosapentaenoic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The eicosapentaenoic acid moiety is derived from fish oils, liver and kidney, while the docosahexaenoic acid moiety is derived from fish oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. C47H72NO8P None None None 23116.0 33860.6 36293.8 35970.5 65455.7 46171.1 35146.8 24838.0 50957.9 35572.0 65034.4 57753.2 10891.9 45958.1 37913.4 37562.7 16894.2 10980.2 27529.9 22932.0 28362.7 42033.6 46518.1 29365.9 35289.6 50954.1 42967.2 36315.6 33682.1 36005.7 32356.7 27335.5 51533.5 26041.7 31261.2 25351.1 30847.2 44426.9 14057.5 40753.1 14658.9 21714.8 828.5905740_MZ Phosphatidylcholine (16:0/22:4(7Z_10Z_13Z_16Z)) Un 1.0 None None None None C46H84NO8P None None None 491886.0 340993.0 484167.0 279467.0 442924.0 322993.0 517759.0 401906.0 446634.0 350529.0 511560.0 418206.0 736218.0 343749.0 285757.0 240169.0 414144.0 961870.0 350104.0 575310.0 327588.0 383860.0 399054.0 360370.0 408134.0 435250.0 247217.0 626031.0 515915.0 312250.0 374647.0 269305.0 562717.0 349240.0 276722.0 438620.0 356241.0 521657.0 455051.0 441245.0 653346.0 391585.0 830.5612989_MZ Phosphatidylcholine (18:1(11Z)/22:6(4Z_7Z_10Z_13Z_16Z_19Z)) Un 1.0 None None None None C48H82NO8P None None None 15977.8 16470.8 17285.8 17103.3 23886.9 20019.5 20966.2 18778.6 20443.8 17773.7 23466.0 22907.6 21959.2 19769.3 17998.6 17152.8 15107.0 16569.0 12602.7 21303.8 15316.0 16970.5 21360.5 14021.7 20608.7 22510.7 17090.9 20075.9 18367.9 17775.2 18149.4 20211.8 22584.0 15959.7 14988.2 17613.6 14480.0 26653.8 10912.2 16882.7 14540.7 14110.5 830.6845352_MZ Glucosylceramide (d18:1/24:0) Un 1.0 None None None None Glucosylceramide (d18:1/24:0) is a glycosphingolipid (ceramide and oligosaccharide)or oligoglycosylceramide with one or more sialic acids (i.e. n-acetylneuraminic acid) linked on the sugar chain. It is a component the cell plasma membrane which modulates cell signal transduction events. Gangliosides have been found to be highly important in immunology. Ganglioside GL1a carries a net-negative charge at pH 7.0 and is acidic. Gangliosides can amount to 6% of the weight of lipids from brain, but they are found at low levels in all animal tissues.Cerebrosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Cerebrosides have a single sugar group linked to ceramide. The most common are galactocerebrosides (containing galactose), the least common are glucocerebrosides (containing glucose). Galactocerebrosides are found predominantly in neuronal cell membranes. In contrast glucocerebrosides are not normally found in membranes. Instead, they are typically intermediates in the synthesis or degradation of more complex glycosphingolipids. Galactocerebrosides are synthesized from ceramide and UDP-galactose. Excess lysosomal accumulation of glucocerebrosides is found in Gaucher disease. C48H93NO8, Glucosylceramide None None None 5154.44 2278.09 2597.03 2986.66 3783.29 2443.4 4273.84 3810.95 3382.08 2812.22 4557.3 3522.82 5432.94 5438.23 2521.11 3296.94 4829.21 5034.99 2260.52 3311.13 2850.29 2046.71 3760.55 2915.48 4347.36 3522.47 2517.08 3494.09 2236.23 3252.85 3600.08 5334.99 3609.28 2223.92 1813.05 2337.4 2624.8 3545.16 2338.4 2867.82 15977.9 2441.55 831.6742982_MZ Sphingomyelin with formula C47H93N2O6P Un 1.0 None None None None Sphingomyelin (d18:1/24:1(15Z)) or SM(d18:1/24:1(15Z)) is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons. It usually consists of phosphorylcholine and ceramide. In humans, sphingomyelin is the only membrane phospholipid not derived from glycerol. Like all sphingolipids, SPH has a ceramide core (sphingosine bonded to a fatty acid via an amide linkage). In addition it contains one polar head group, which is either phosphocholine or phosphoethanolamine. The plasma membrane of cells is highly enriched in sphingomyelin and is considered largely to be found in the exoplasmic leaflet of the cell membrane. However, there is some evidence that there may also be a sphingomyelin pool in the inner leaflet of the membrane. Moreover, neutral sphingomyelinase-2 - an enzyme that breaks down sphingomyelin into ceramide has been found to localise exclusively to the inner leaflet further suggesting that there may be sphingomyelin present there. Sphingomyelin can accumulate in a rare hereditary disease called Niemann-Pick Disease, types A and B. Niemann-Pick disease is a genetically-inherited disease caused by a deficiency in the enzyme Sphingomyelinase, which causes the accumulation of Sphingomyelin in spleen, liver, lungs, bone marrow, and the brain, causing irreversible neurological damage. SMs play a role in signal transduction. Sphingomyelins are synthesized by the transfer of phosphorylcholine from phosphatidylcholine to a ceramide in a reaction catalyzed by sphingomyelin synthase. C47H93N2O6P None None None 32421.1 28418.5 26550.0 31981.8 44083.8 20138.0 39728.3 47219.7 43990.4 28632.4 45485.7 35264.7 36177.3 50929.1 28613.1 18692.8 50010.9 34119.6 23163.7 28834.5 34018.6 29350.1 38165.8 24363.8 34469.1 42990.4 27662.4 34724.8 22275.5 25316.0 31549.3 20605.9 41711.5 23436.2 21412.3 27605.7 40176.9 38201.0 19093.9 34174.1 33127.0 31058.4 832.5127914_MZ Phosphatidylserine (18:1(9Z)/22:6(4Z_7Z_10Z_13Z_16Z_19Z)) Un 1.0 None None None None PS(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PS(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of oleic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the docosahexaenoic acid moiety is derived from fish oils. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE. C46H76NO10P None None None 54305.1 54786.7 51811.6 74862.8 69606.2 52466.5 69335.8 72349.7 58149.0 58737.4 67353.6 66425.1 68284.4 65318.7 45844.8 52478.4 64372.0 60850.1 46307.0 64252.1 49291.9 45170.5 62719.4 49365.7 63239.5 68889.7 48625.4 63977.9 44472.3 53500.7 68060.2 67305.4 60530.3 50248.9 33071.6 47657.3 52569.2 54144.7 47969.7 53623.7 64501.0 55106.6 833.5173433_MZ Phosphatidylinositol16:0/18:2(9Z_12Z)) Un 1.0 None None None None PI(16:0/18:2(9Z,12Z)) is a phosphatidylinositol. Phosphatidylinositols are important lipids, both as a key membrane constituent and as a participant in essential metabolic processes, both directly and via a number of metabolites. Phosphatidylinositols are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to inositol (hexahydroxycyclohexane). Phosphatidylinositols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 18 and 20 carbons are the most common. PI(16:0/18:2(9Z,12Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of linoleic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the linoleic acid moiety is derived from seed oils. In most organisms, the stereochemical form of the last is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial. Phosphatidylinositol is especially abundant in brain tissue, where it can amount to 10% of the phospholipids, but it is present in all tissues and cell types. There is usually less of it than of phosphatidylcholine, phosphatidylethanolamine and phosphatidylserine. In animal tissues, phosphatidylinositol is the primary source of the arachidonic acid required for biosynthesis of eicosanoids, including prostaglandins, via the action of the enzyme phospholipase A2. Phosphatidylinositol can be phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated by a specific kinase. Seven different isomers are known, but the most important in both quantitative and biological terms are phosphatidylinositol 4-phosphate and phosphatidylinositol 4,5-bisphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PIs contain almost exclusively stearic acid at carbon 1 and arachidonic acid at carbon 2. PIs composed exclusively of non-phosphorylated inositol exhibit a net charge of -1 at physiological pH. Molecules with phosphorylated inositol (such as PIP, PIP2, PIP3, etc.) are termed polyphosphoinositides. The polyphosphoinositides are important intracellular transducers of signals emanating from the plasma membrane. The synthesis of PI involves CDP-activated 1,2-diacylglycerol condensation with myo-inositol. C43H79O13P None None None 118555.0 166444.0 108300.0 151224.0 104495.0 117900.0 154553.0 165852.0 114773.0 86521.2 149146.0 193461.0 77861.8 124972.0 80248.8 99437.0 161292.0 70849.8 75421.8 99900.8 120126.0 110995.0 151561.0 82897.2 115965.0 131127.0 106814.0 133317.0 85184.0 128211.0 173193.0 105356.0 100969.0 94917.2 62316.3 87940.7 85654.5 116757.0 61239.4 111624.0 76380.7 91151.4 834.4872865_MZ Phosphatidylethanolamine with formula C49H74NO8P Un 1.0 None None None None PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of two chains of docosahexaenoic acid at the C-1 and C-2 positions. The docosahexaenoic acid moieties are derived from fish oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. C49H74NO8P None None None 12223.1 20059.0 23608.0 29080.6 37200.6 23692.6 22329.9 16071.3 30438.6 19846.6 34083.1 37271.6 19977.2 22920.8 22150.8 20688.4 14581.4 7647.1 15575.9 29191.7 16306.7 22946.6 25064.8 16268.3 28772.5 31626.1 23217.6 24089.7 18564.1 18036.8 18672.3 24719.7 26674.4 15567.6 18171.4 16850.2 19998.4 52536.2 9304.24 22207.1 8940.56 13434.0 834.5281005_MZ Phosphatidylserine (18:0/22:6(4Z_7Z_10Z_13Z_16Z_19Z)) Un 1.0 None None None None PS(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PS(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the docosahexaenoic acid moiety is derived from fish oils. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE. C46H78NO10P None None None 282688.0 520313.0 250125.0 372678.0 277576.0 252394.0 439608.0 497474.0 320582.0 203914.0 350371.0 517826.0 295747.0 299289.0 205160.0 248452.0 485750.0 292316.0 249880.0 467475.0 311928.0 237758.0 342115.0 221744.0 326083.0 339374.0 214398.0 458163.0 219365.0 308476.0 496964.0 254173.0 283110.0 297483.0 123440.0 220370.0 389645.0 267273.0 174816.0 254135.0 303323.0 263887.0 835.0517511_MZ Diadenosine tetraphosphate Un 1.0 None None None None Diadenosine tetraphosphate (AP4A) is a diadenosine polyphosphate. Diadenosine polyphosphates (APnAs, n=3-6) are a family of endogenous vasoactive purine dinucleotides which have been isolated from thrombocytes. APnAs have been demonstrated to be involved in the control of vascular tone as well as the growth of vascular smooth muscle cells and hence, possibly, in atherogenesis. APnAs isolated substances are Ap3A, Ap4A, Ap5A, and Ap6A. APnAs are naturally occurring substances that facilitate tear secretion; they are released from the corneal epithelium, they stimulate tear production and therefore they may be considered as physiological modulators of tear secretion. The APnAs were discovered in the mid-sixties in the course of studies on aminoacyl-tRNA synthetases (aaRS). APnAs have emerged as intracellular and extracellular signalling molecules implicated in the maintenance and regulation of vital cellular functions and become considered as second messengers. Great variety of physiological and pathological effects in mammalian cells was found to be associated with alterations of APnAs. APnAs are polyphosphated nucleotidic substances which are found in the CNS and are known to be released in a calcium-dependent manner from storage vesicles in brain synaptosomes. AP5A is a specific adenylate kinase inhibitor in the hippocampus, decreasing the rate of decomposition of ADP and the formation of ATP; a pathway that influences the availability of purines in the central nervous system. AP4A is the only APnA that can induce a considerable increase in [Ca2+] in endothelial cells, indicating that its vasoactive effects are comparable to the known effects of arginine vasopressin, Angiotensin II, and ATP. AP4A is a ubiquitous ApnA is a signal molecule for DNA replication in mammalian cells. AP4A is a primer for oligoadenylate synthesis catalyzed by interferon-inducible 2-5A synthetase. AP4A is an avid inhibitor of eosinophil-derived neurotoxin (EDN). EDN is a catalytically proficient member of the pancreatic ribonuclease superfamily secreted along with other eosinophil granule proteins during innate host defense responses and various eosinophil-related inflammatory and allergic diseases. The ribonucleolytic activity of EDN is central to its antiviral and neurotoxic activities and possibly to other facets of its biological activity. (PMID: 11212966, 12738682, 11810214, 9607303, 8922753, 9187362, 16401072, 9694344, 9351706, 1953194). C20H28N10O19P4 None None None 12735.3 12915.5 12985.5 6795.45 9217.53 11808.8 10728.5 11820.8 8597.22 6971.28 9307.93 11834.5 9392.14 12295.4 8842.21 9230.46 9530.59 7848.0 8457.79 10569.9 13054.9 11500.7 8475.18 11883.0 9169.42 11031.0 11149.3 9912.34 11799.0 10761.7 15142.8 7675.18 10224.0 8441.16 15627.9 10098.7 9716.26 11458.9 6874.17 8621.57 11569.5 9810.68 837.5462168_MZ Phosphatidylinositol16:0/18:0) Un 1.0 None None None None PI(16:0/18:0) is a phosphatidylinositol. Phosphatidylinositols are important lipids, both as a key membrane constituent and as a participant in essential metabolic processes, both directly and via a number of metabolites. Phosphatidylinositols are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to inositol (hexahydroxycyclohexane). Phosphatidylinositols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 18 and 20 carbons are the most common. PI(16:0/18:0), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of stearic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the stearic acid moiety is derived from animal fats, coco butter and sesame oil. In most organisms, the stereochemical form of the last is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial. Phosphatidylinositol is especially abundant in brain tissue, where it can amount to 10% of the phospholipids, but it is present in all tissues and cell types. There is usually less of it than of phosphatidylcholine, phosphatidylethanolamine and phosphatidylserine. In animal tissues, phosphatidylinositol is the primary source of the arachidonic acid required for biosynthesis of eicosanoids, including prostaglandins, via the action of the enzyme phospholipase A2. Phosphatidylinositol can be phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated by a specific kinase. Seven different isomers are known, but the most important in both quantitative and biological terms are phosphatidylinositol 4-phosphate and phosphatidylinositol 4,5-bisphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PIs contain almost exclusively stearic acid at carbon 1 and arachidonic acid at carbon 2. PIs composed exclusively of non-phosphorylated inositol exhibit a net charge of -1 at physiological pH. Molecules with phosphorylated inositol (such as PIP, PIP2, PIP3, etc.) are termed polyphosphoinositides. The polyphosphoinositides are important intracellular transducers of signals emanating from the plasma membrane. The synthesis of PI involves CDP-activated 1,2-diacylglycerol condensation with myo-inositol. C43H83O13P None None None 32508.5 40906.9 35286.2 39780.1 40235.1 36137.9 44496.3 56146.8 37065.5 31049.5 42170.2 50995.7 29770.5 45826.9 27565.9 29590.7 39462.2 30181.5 26668.7 45797.1 32948.9 30080.8 39436.9 29012.3 34326.7 39036.4 29126.5 43977.3 29172.8 35527.9 39447.2 28220.0 42026.6 29880.0 21439.6 26493.0 33806.1 36491.4 21868.0 31975.6 28735.9 29889.1 837.6574585_MZ 3-Decaprenyl-4-hydroxybenzoic acid Un 1.0 None None None None 3-Decaprenyl-4-hydroxybenzoic acid is the first intermediate in the conversion of p-hydroxybenzoate (PHB) to ubiquinone. It is a 3-polyprenyl derivative of PHB. It has been found that PPHB is located primarily in the inner membrane of liver mitochondria. (PMID: 4338233). C57H86O3 None None None 4865.9 6343.91 4047.78 6388.54 5396.9 3971.59 6118.91 4648.89 7682.09 4686.99 6656.11 5653.6 4926.5 6949.69 5069.23 4351.97 7895.67 4480.91 4720.57 4749.76 5121.41 5469.28 8496.32 5241.26 6605.52 5295.88 6374.47 5918.94 3577.27 5412.96 5516.58 5099.81 5679.6 5114.04 2809.59 4305.06 5140.47 6935.96 2962.05 6189.81 3726.4 4085.18 837.7434592_MZ Tricaprylic glyceride (15:0/18:1(9Z)/16:0)[iso6] Un 1.0 None None None None TG(15:0/18:1(9Z)/16:0) is a monooleic acid triglyceride. Triglycerides (TGs) are also known as triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.e. fatty acid trimesters of glycerol). TGs may be divided into three general types with respect to their acyl substituents. They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. TG(15:0/18:1(9Z)/16:0), in particular, consists of one chain of pentadecanoic acid at the C-1 position, one chain of oleic acid at the C-2 position and one chain of palmitic acid at the C-3 position. TGs are the main constituent of vegetable oil and animal fats. TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) with the help of lipases and bile secretions, which can then move into blood vessels. The triglycerides are rebuilt in the blood from their fragments and become constituents of lipoproteins, which deliver the fatty acids to and from fat cells among other functions. Various tissues can release the free fatty acids and take them up as a source of energy. Fat cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain cannot utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when it is broken down. (www.cyberlipid.org, www.wikipedia.org)TAGs can serve as fatty acid stores in all cells, but primarily in adipocytes of adipose tissue. The major building block for the synthesis of triacylglycerides, in non-adipose tissue, is glycerol. Adipocytes lack glycerol kinase and so must use another route to TAG synthesis. Specifically, dihydroxyacetone phosphate (DHAP), which is produced during glycolysis, is the precursor for TAG synthesis in adipose tissue. DHAP can also serve as a TAG precursor in non-adipose tissues, but does so to a much lesser extent than glycerol. The use of DHAP for the TAG backbone depends on whether the synthesis of the TAGs occurs in the mitochondria and ER or the ER and the peroxisomes. The ER/mitochondria pathway requires the action of glycerol-3-phosphate dehydrogenase to convert DHAP to glycerol-3-phosphate. Glycerol-3-phosphate acyltransferase then esterifies a fatty acid to glycerol-3-phosphate thereby generating lysophosphatidic acid. The ER/peroxisome reaction pathway uses the peroxisomal enzyme DHAP acyltransferase to acylate DHAP to acyl-DHAP which is then reduced by acyl-DHAP reductase. The fatty acids that are incorporated into TAGs are activated to acyl-CoAs through the action of acyl-CoA synthetases. Two molecules of acyl-CoA are esterified to glycerol-3-phosphate to yield 1,2-diacylglycerol phosphate (also known as phosphatidic acid). The phosphate is then removed by phosphatidic acid phosphatase (PAP1), to generate 1,2-diacylglycerol. This diacylglycerol serves as the substrate for addition of the third fatty acid to make TAG. Intestinal monoacylglycerols, derived from dietary fats, can also serve as substrates for the synthesis of 1,2-diacylglycerols. C52H98O6 None None None 303.154 182.028 161.962 401.631 298.701 167.666 303.629 322.873 173.786 320.991 306.924 107.621 398.339 161.281 361.744 750.027 289.23 409.706 249.347 235.529 289.464 132.204 348.195 309.79 653.625 142.333 254.792 296.341 149.47 390.489 488.82 1512.26 105.294 240.471 382.304 279.341 180.374 92.844 172.418 85.9642 470.48 235.234 839.2945283_MZ 3-Sialyl Lewis Un 1.0 None None None None 3-Sialyl Lewis tetrasaccharide, is a tumor-associated carbohydrate antigen. It is used as a tumor marker in colon and pancreatic cancer. When the selectin family of adhesion molecules was described, it was found that 3-Sialyl Lewis, along with sialyl Lewis(x) antigen, is a ligand for E-selectin, responsible for adhesion of several types of human carcinoma cells to endothelium. It has been suggested that such interactions play an important role in the formation of metastases by colon and pancreatic cancer cells. (PMID:12362971). C31H52N2O23 None None None 693.65 613.3 1844.76 340.443 704.058 754.242 367.589 364.176 1079.28 409.252 784.886 1156.4 145.86 973.26 598.818 183.403 1015.38 76.9576 674.078 278.889 755.335 1390.75 775.34 1136.23 1022.92 1876.96 1024.21 579.864 1944.76 692.549 135.135 298.908 1407.96 933.37 3309.25 1097.59 897.552 650.511 802.906 1107.78 905.606 1313.21 847.3841740_MZ Neuromedin B (4-10) Un 1.0 None None None None NMB acts by binding to its high affinity cell surface receptor, neuromedin B receptor (NMBR). This receptor is a G protein-coupled receptor with seven transmembrane spanning regions, hence the receptor is also denoted as a 7 transmembrane receptor (7-TMR). Upon binding several intracellular signaling pathways are triggered (see Figure 2). Neuromedin B (NMB) is a bombesin-related peptide in mammals. It was originally purified from pig spinal cord, and later shown to be present in human central nervous system and gastrointestinal tract. This structure shows the 4-10 fragment of neuromedin B. C40H54N11O8S None None None 1027.77 1058.59 1112.56 1174.12 2185.0 1795.99 1561.53 1072.16 1256.54 1158.35 1513.27 1921.67 673.785 1233.76 1439.97 1678.95 745.28 779.919 1021.85 1019.3 1037.84 1118.91 1485.31 1011.39 1480.85 1200.72 2374.73 870.744 865.112 1056.14 1235.24 1368.07 1388.45 927.322 1079.1 841.334 826.98 1293.47 614.373 1273.47 2060.53 975.996 848.5549567_MZ Phosphatidylcholine with formula C48H80NO8P Un 1.0 None None None None C48H80NO8P None None None 40203.5 33297.1 36092.3 33139.8 57642.9 41066.5 45300.8 39490.7 40047.2 36165.4 45077.2 44309.4 54360.5 41304.1 31660.1 37594.6 41024.4 51178.3 27750.6 52791.9 34199.7 34636.0 46219.2 32501.4 46768.8 51828.4 31310.8 48689.4 43403.3 41536.7 40564.0 45233.9 40893.2 34387.9 30553.4 47823.3 32854.4 61287.1 25085.2 34084.0 42362.7 30763.2 851.3479911_MZ Heme A Un 1.0 None None None None Heme A differs from heme B in that a methyl side chain at ring position 8 is oxidized into a formyl group, and one of the vinyl side chains, at ring position 2, has been replaced by an isoprenoid chain. Like heme B, heme A is often attached to the apoprotein (cytochromes or globins) through a coordination bond between the heme iron and a conserved amino acid side-chain. An example of a metalloprotein that contains heme A is cytochrome c oxidase. Both the formyl group and the isoprenoid side chain are thought to play important roles in conservation of the energy of oxygen reduction by cytochrome c oxidase.(Wikipedia). C49H56FeN4O6 None None None 343.898 513.225 236.876 728.371 687.291 410.73 550.785 415.983 439.503 419.79 446.006 867.886 234.248 357.365 490.878 705.501 326.76 64.0717 340.689 238.887 320.28 343.055 405.855 293.094 287.016 277.987 562.171 323.594 257.623 417.733 340.4 786.048 277.846 301.175 334.223 361.115 202.132 472.879 230.261 514.947 262.061 226.729 852.3074772_MZ Lacto-N-fucopentaose III Un 1.0 None None None None Lacto-N-fucopentaose III is an oligosaccharide found in human milk. Oligosaccharides in human milk represent a group of bioactive molecules that have evolved to be an abundant and diverse component of human milk, even though they have no direct nutritive value to the infant. A recent hypothesis proposes that they could be substrates for the development of the intestinal microflora and the mucosal immune system. (PMID:17002410). C32H55NO25, Lacto-N-fucopentaose-2, Lex-lactose, Lacto-n-fucopentaose I, Lacto-N-fucopentaose V None None None 125.997 195.551 158.582 286.608 198.719 228.5 181.762 260.493 104.067 119.322 275.851 140.198 66.0864 342.335 277.449 345.029 126.064 129.788 143.496 265.088 160.65 63.7804 208.421 232.615 268.22 163.508 310.443 176.705 60.7106 122.933 165.537 310.116 211.569 170.577 169.544 119.811 228.077 230.375 128.891 216.051 1085.75 111.454 852.5887619_MZ Phosphatidylcholine with formula C48H84NO8P Un 1.0 None None None None PC(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the docosahexaenoic acid moiety is derived from fish oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C48H84NO8P None None None 124766.0 100156.0 117657.0 84854.0 105844.0 87891.5 131205.0 115417.0 122513.0 95000.4 119487.0 114520.0 171883.0 80490.7 74534.5 79336.6 103670.0 221191.0 91874.3 170862.0 87863.2 87013.2 98294.5 85683.5 113445.0 98658.1 63743.7 136699.0 123287.0 94035.5 109224.0 64822.8 128153.0 97979.7 59727.7 99770.5 96316.2 117641.0 103061.0 100782.0 148452.0 92926.7 852.6828063_MZ Phosphatidylcholine (24:1(15Z)/P-18:1(11Z)) Un 1.0 None None None None PC(24:1(15Z)/P-18:1(11Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(24:1(15Z)/P-18:1(11Z)), in particular, consists of one chain of nervonic acid at the C-1 position and one chain of plasmalogen 18:1n7 at the C-2 position. The nervonic acid moiety is derived from fish oils, while the plasmalogen 18:1n7 moiety is derived from animal fats, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. C50H96NO7P None None None 26245.0 22781.9 22084.7 26765.0 35337.0 16915.2 31664.7 38876.4 35566.8 24279.6 36334.6 27659.5 30679.5 40812.9 22970.9 15981.6 40706.7 29436.0 20021.9 24036.6 28125.8 25381.3 31019.5 20884.0 28748.7 34726.0 22209.1 28313.5 18773.1 21534.8 25029.0 18178.0 35140.7 20177.9 17148.6 22937.9 34011.4 32525.0 17607.6 28534.3 25199.4 26095.6 854.1327512_MZ Crotonoyl-CoA Un 1.0 None None None None Crotonoyl-CoA is an important component in several metabolic pathways, notably fatty acid and amino acid metabolism. It is the substrate of a group of enzymes acyl-Coenzyme A oxidases 1, 2, 3 (E.C.: 1.3.3.6) corresponding to palmitoyl, branched chain, and pristanoyl, respectively, in the peroxisomal fatty acid beta-oxidation, producing hydrogen peroxide. Abnormality of this group of enzymes is linked to coma, dehydration, diabetes, fatty liver, hyperinsulinemia, hyperlipidemia, and leukodystrophy. It is also a substrate of a group of enzymes called acyl-Coenzyme A dehydrogenase (E.C.:1.3.99-, including 1.3.99.2, 1.3.99.3) in the metabolism of fatty acids or branched chain amino acids in the mitochondria (Rozen et al., 1994). Acyl-Coenzyme A dehydrogenase (1.3.99.3) has shown to contribute to kidney-associated diseases, such as adrenogential syndrome, kidney failure, kidney tubular necrosis, homocystinuria, as well as other diseases including cretinism, encephalopathy, hypoglycemia, medium chain acyl-CoA dehydrogenase deficiency. The gene (ACADS) also plays a role in theta oscillation during sleep. In addition, crotonoyl-CoA is the substrate of enoyl coenzyme A hydratase (E.C.4.2.1.17) in the mitochondria during lysine degradation and tryptophan metabolism, benzoate degradation via CoA ligation; in contrast it is the product of this enzyme in the butanoate metabolism. Moreover, it is produced from multiple enzymes in the butanoate metabolism pathway, including 3-Hydroxybutyryl-CoA dehydratase (E.C.:4.2.1.55), glutaconyl-CoA decarboxylase (E.C.: 4.1.1.70), vinylacetyl-CoA Δ-isomerase (E.C.: 5.3.3.3), and trans-2-enoyl-CoA reductase (NAD+) (E.C.: 1.3.1.44). In lysine degradation and tryptophan metabolism, crotonoyl CoA is produced by glutaryl-Coenzyme A dehydrogenase (E.C.:1.3.99.7) lysine and tryptophan metabolic pathway. This enzyme is linked to type-1glutaric aciduria, metabolic diseases, movement disorders, myelinopathy, and nervous system diseases. C25H40N7O17P3S None None None 4399.17 3454.73 4415.26 1950.42 2641.83 3844.37 3485.24 2821.62 2981.94 2490.92 2438.77 2536.15 3352.46 4135.31 2808.65 2382.31 2764.82 3705.92 3241.23 3600.56 3382.92 3235.77 2437.93 3237.65 2678.14 2513.21 2584.42 2933.4 3987.41 4898.6 3105.74 1804.29 3661.78 2501.4 4601.6 3143.52 4101.28 3582.83 3020.3 2377.12 3055.63 2362.18 854.6971184_MZ Phosphatidylcholine with formula C50H98NO7P Un 1.0 None None None None PC(24:0/P-18:1(11Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(24:0/P-18:1(11Z)), in particular, consists of one chain of lignoceric acid at the C-1 position and one chain of plasmalogen 18:1n7 at the C-2 position. The lignoceric acid moiety is derived from groundnut oil, while the plasmalogen 18:1n7 moiety is derived from animal fats, liver and kidney. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. C50H98NO7P None None None 9234.25 13216.2 8913.53 13112.2 9510.8 9765.05 15256.0 10575.0 11890.6 8444.88 11695.6 17821.1 9157.47 9545.6 7844.84 6426.08 17797.7 8920.52 9673.1 8838.23 10027.8 7607.72 10858.4 8736.69 12181.9 11954.5 10003.2 10987.1 5541.28 9589.93 11765.1 8882.62 10558.7 9059.25 5394.58 6607.07 11707.5 13737.2 7639.79 8434.98 7736.7 7079.93 855.2734840_MZ Uroporphyrinogen I Un 1.0 None None None None Uroporphyrinogens are porphyrinogen variants in which each pyrrole ring has one acetate side chain and one propionate side chain; it is formed by condensation 4 four molecules of porphobilinogen. 4 isomers are possible but only 2 commoly are found, types I and III. Uroporphyrinogen III is a functional intermediate in heme biosynthesis while Uroporphyrinogen I is produced in an abortive side reaction. C40H44N4O16 None None None 371.377 305.363 429.571 364.317 347.843 326.61 364.133 220.62 161.582 490.717 240.661 2042.06 131.694 643.752 358.07 258.01 325.171 242.818 435.783 254.846 333.226 258.184 169.728 314.562 366.593 301.172 550.213 297.224 490.993 616.838 405.754 256.229 365.681 392.005 365.799 272.777 315.351 132.873 98.9892 384.833 1002.79 904.042 855.5426485_MZ Phosphatidylinositol16:0/18:1(11Z)) Un 1.0 None None None None PI(16:0/18:1(11Z)) is a phosphatidylinositol. Phosphatidylinositols are important lipids, both as a key membrane constituent and as a participant in essential metabolic processes, both directly and via a number of metabolites. Phosphatidylinositols are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to inositol (hexahydroxycyclohexane). Phosphatidylinositols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 18 and 20 carbons are the most common. PI(16:0/18:1(11Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of vaccenic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the vaccenic acid moiety is derived from butter fat and animal fat. In most organisms, the stereochemical form of the last is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial. Phosphatidylinositol is especially abundant in brain tissue, where it can amount to 10% of the phospholipids, but it is present in all tissues and cell types. There is usually less of it than of phosphatidylcholine, phosphatidylethanolamine and phosphatidylserine. In animal tissues, phosphatidylinositol is the primary source of the arachidonic acid required for biosynthesis of eicosanoids, including prostaglandins, via the action of the enzyme phospholipase A2. Phosphatidylinositol can be phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated by a specific kinase. Seven different isomers are known, but the most important in both quantitative and biological terms are phosphatidylinositol 4-phosphate and phosphatidylinositol 4,5-bisphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PIs contain almost exclusively stearic acid at carbon 1 and arachidonic acid at carbon 2. PIs composed exclusively of non-phosphorylated inositol exhibit a net charge of -1 at physiological pH. Molecules with phosphorylated inositol (such as PIP, PIP2, PIP3, etc.) are termed polyphosphoinositides. The polyphosphoinositides are important intracellular transducers of signals emanating from the plasma membrane. The synthesis of PI involves CDP-activated 1,2-diacylglycerol condensation with myo-inositol. C43H81O13P None None None 69203.9 67494.3 58073.2 76771.5 54474.1 47386.4 59571.6 57749.8 67883.4 55023.9 78555.8 89522.9 31851.8 62344.5 46966.9 37490.8 71722.1 48147.8 45299.8 114056.0 58162.7 51645.2 64580.0 42949.1 58640.9 56941.1 56157.6 71536.6 55412.6 71336.7 102117.0 35546.7 58513.1 67347.9 45405.6 51803.2 49304.4 55298.4 35110.3 49222.3 83907.7 44400.4 856.5413274_MZ Phosphatidylserine (18:0/22:5(7Z_10Z_13Z_16Z_19Z)) Un 1.0 None None None None PS(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PS(18:0/22:5(7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of docosapentaenoic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the docosapentaenoic acid moiety is derived from fish oils. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE. C46H80NO10P None None None 107258.0 128090.0 117862.0 132857.0 120431.0 91836.8 119110.0 125701.0 138142.0 107417.0 159193.0 186883.0 73776.8 122172.0 98245.2 75667.4 114441.0 108726.0 85349.6 139472.0 107447.0 105249.0 115960.0 90433.1 116990.0 127853.0 106369.0 129970.0 107645.0 116558.0 117968.0 66534.4 135864.0 110250.0 82261.0 93522.2 111415.0 114142.0 85601.3 97298.4 91721.6 95507.8 857.5187760_MZ Phosphatidylinositol16:0/20:4(5Z_8Z_11Z_14Z)) Un 1.0 None None None None PI(16:0/20:4(5Z,8Z,11Z,14Z)) is a phosphatidylinositol. Phosphatidylinositols are important lipids, both as a key membrane constituent and as a participant in essential metabolic processes, both directly and via a number of metabolites. Phosphatidylinositols are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to inositol (hexahydroxycyclohexane). Phosphatidylinositols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 18 and 20 carbons are the most common. PI(16:0/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of arachidonic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the arachidonic acid moiety is derived from animal fats and eggs. In most organisms, the stereochemical form of the last is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial. Phosphatidylinositol is especially abundant in brain tissue, where it can amount to 10% of the phospholipids, but it is present in all tissues and cell types. There is usually less of it than of phosphatidylcholine, phosphatidylethanolamine and phosphatidylserine. In animal tissues, phosphatidylinositol is the primary source of the arachidonic acid required for biosynthesis of eicosanoids, including prostaglandins, via the action of the enzyme phospholipase A2. Phosphatidylinositol can be phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated by a specific kinase. Seven different isomers are known, but the most important in both quantitative and biological terms are phosphatidylinositol 4-phosphate and phosphatidylinositol 4,5-bisphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PIs contain almost exclusively stearic acid at carbon 1 and arachidonic acid at carbon 2. PIs composed exclusively of non-phosphorylated inositol exhibit a net charge of -1 at physiological pH. Molecules with phosphorylated inositol (such as PIP, PIP2, PIP3, etc.) are termed polyphosphoinositides. The polyphosphoinositides are important intracellular transducers of signals emanating from the plasma membrane. The synthesis of PI involves CDP-activated 1,2-diacylglycerol condensation with myo-inositol. C45H79O13P None None None 347908.0 433678.0 286676.0 356057.0 314623.0 242975.0 366764.0 405618.0 305165.0 191771.0 356789.0 414329.0 381434.0 377681.0 194073.0 262728.0 477844.0 308399.0 237620.0 365942.0 421310.0 245539.0 325866.0 250955.0 341338.0 273496.0 242426.0 361444.0 232810.0 308449.0 452371.0 280573.0 262492.0 241481.0 165330.0 278590.0 220128.0 252424.0 213297.0 276784.0 282255.0 255356.0 858.6222850_MZ Phosphatidylcholine with formula C48H90NO8P Un 1.0 None None None None C48H90NO8P None None None 9949.82 9330.84 8698.17 7789.16 8207.26 8543.74 9471.48 8857.79 9075.06 7159.08 10062.3 10818.9 10038.8 9869.91 6144.44 8637.5 7986.39 11135.1 6557.49 11078.7 8636.68 7887.55 9162.24 7603.35 8361.93 8790.24 6193.56 9988.39 8594.93 8578.78 8749.52 7342.76 9036.11 8156.92 5778.98 8379.08 8804.86 9525.26 6058.18 7478.81 7659.81 6511.03 859.5312756_MZ Phosphatidylinositol16:0/20:3(5Z_8Z_11Z)) Un 1.0 None None None None PI(16:0/20:3(5Z,8Z,11Z)) is a phosphatidylinositol. Phosphatidylinositols are important lipids, both as a key membrane constituent and as a participant in essential metabolic processes, both directly and via a number of metabolites. Phosphatidylinositols are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to inositol (hexahydroxycyclohexane). Phosphatidylinositols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 18 and 20 carbons are the most common. PI(16:0/20:3(5Z,8Z,11Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of mead acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the mead acid moiety is derived from fish oils, liver and kidney. In most organisms, the stereochemical form of the last is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial. Phosphatidylinositol is especially abundant in brain tissue, where it can amount to 10% of the phospholipids, but it is present in all tissues and cell types. There is usually less of it than of phosphatidylcholine, phosphatidylethanolamine and phosphatidylserine. In animal tissues, phosphatidylinositol is the primary source of the arachidonic acid required for biosynthesis of eicosanoids, including prostaglandins, via the action of the enzyme phospholipase A2. Phosphatidylinositol can be phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated by a specific kinase. Seven different isomers are known, but the most important in both quantitative and biological terms are phosphatidylinositol 4-phosphate and phosphatidylinositol 4,5-bisphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PIs contain almost exclusively stearic acid at carbon 1 and arachidonic acid at carbon 2. PIs composed exclusively of non-phosphorylated inositol exhibit a net charge of -1 at physiological pH. Molecules with phosphorylated inositol (such as PIP, PIP2, PIP3, etc.) are termed polyphosphoinositides. The polyphosphoinositides are important intracellular transducers of signals emanating from the plasma membrane. The synthesis of PI involves CDP-activated 1,2-diacylglycerol condensation with myo-inositol. C45H81O13P None None None 162599.0 148315.0 116188.0 146546.0 145662.0 132885.0 176339.0 178339.0 134676.0 83866.6 154743.0 181994.0 131664.0 177210.0 77803.4 135443.0 178176.0 113555.0 88202.8 127104.0 147936.0 115160.0 167511.0 117175.0 140891.0 200107.0 133290.0 136929.0 121841.0 130975.0 170768.0 103609.0 127658.0 128252.0 86831.7 142474.0 102409.0 133852.0 70189.6 120661.0 120398.0 113477.0 860.6564633_MZ Phosphatidylcholine with formula C48H92NO8P Un 1.0 None None None None C48H92NO8P None None None 2030.63 2219.21 1955.85 2615.32 2011.41 1776.89 1982.24 2370.4 2358.16 1534.25 2503.9 2490.65 1134.73 2645.39 1424.71 2094.6 2028.37 2072.91 1334.23 2251.87 1775.41 1959.66 2361.1 1560.46 1966.47 2481.75 1516.53 2122.2 1845.29 2144.31 1962.95 2740.43 2148.28 2196.18 1378.92 1698.88 2091.39 2170.37 1169.47 1696.43 1789.38 1272.19 861.5484929_MZ Phosphatidylinositol16:0/20:2(11Z_14Z)) Un 1.0 None None None None PI(16:0/20:2(11Z,14Z)) is a phosphatidylinositol. Phosphatidylinositols are important lipids, both as a key membrane constituent and as a participant in essential metabolic processes, both directly and via a number of metabolites. Phosphatidylinositols are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to inositol (hexahydroxycyclohexane). Phosphatidylinositols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 18 and 20 carbons are the most common. PI(16:0/20:2(11Z,14Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of eicosadienoic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the eicosadienoic acid moiety is derived from fish oils and liver. In most organisms, the stereochemical form of the last is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial. Phosphatidylinositol is especially abundant in brain tissue, where it can amount to 10% of the phospholipids, but it is present in all tissues and cell types. There is usually less of it than of phosphatidylcholine, phosphatidylethanolamine and phosphatidylserine. In animal tissues, phosphatidylinositol is the primary source of the arachidonic acid required for biosynthesis of eicosanoids, including prostaglandins, via the action of the enzyme phospholipase A2. Phosphatidylinositol can be phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated by a specific kinase. Seven different isomers are known, but the most important in both quantitative and biological terms are phosphatidylinositol 4-phosphate and phosphatidylinositol 4,5-bisphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PIs contain almost exclusively stearic acid at carbon 1 and arachidonic acid at carbon 2. PIs composed exclusively of non-phosphorylated inositol exhibit a net charge of -1 at physiological pH. Molecules with phosphorylated inositol (such as PIP, PIP2, PIP3, etc.) are termed polyphosphoinositides. The polyphosphoinositides are important intracellular transducers of signals emanating from the plasma membrane. The synthesis of PI involves CDP-activated 1,2-diacylglycerol condensation with myo-inositol. C45H83O13P None None None 131392.0 129645.0 95292.6 178782.0 107863.0 131676.0 173163.0 189073.0 104526.0 90447.6 136302.0 177002.0 83468.6 140532.0 76550.3 114244.0 164408.0 80796.3 71865.4 92991.6 96072.8 86543.1 154571.0 85688.9 105922.0 194692.0 118575.0 125231.0 73364.2 123383.0 138139.0 83588.1 118847.0 114406.0 65468.4 102376.0 159788.0 115688.0 45214.7 109800.0 92385.8 100552.0 862.6086627_MZ 3-O-Sulfogalactosylceramide (d18:1/22:0) Un 1.0 None None None None C46H89NO11S None None None 17671.8 16770.3 17936.3 21045.7 18230.4 17549.0 21043.0 20641.7 20091.1 15368.0 22307.2 23612.7 17168.7 19881.1 12996.1 17594.9 21415.8 16957.4 13527.5 17446.9 14823.9 17719.4 21184.3 13987.6 17177.7 20241.5 15150.5 19951.3 17318.9 17279.6 16287.5 15836.0 20759.5 18186.8 11525.8 17479.8 19747.2 21353.3 11530.5 17118.7 26320.4 14626.6 863.6181108_MZ All trans decaprenyl diphosphate Un 1.0 None None None None C50H90O7P2 None None None 8668.8 8368.9 9158.15 9344.71 8967.54 8248.37 10488.0 9176.51 9321.0 7131.11 10559.5 12040.6 6988.83 8895.93 6939.61 7940.02 10730.6 8435.7 6590.28 9412.97 7410.6 7726.58 9504.65 7306.18 8495.9 9054.28 6674.95 9634.95 8068.77 8561.89 8175.54 7657.18 9571.4 8527.54 5396.5 7936.45 9181.55 9780.61 6409.6 7606.68 10511.8 6696.95 864.6471313_MZ Phosphatidylcholine (18:3(6Z_9Z_12Z)/24:1(15Z)) Un 1.0 None None None None PC(18:3(6Z,9Z,12Z)/24:1(15Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(18:3(6Z,9Z,12Z)/24:1(15Z)), in particular, consists of one chain of g-linolenic acid at the C-1 position and one chain of nervonic acid at the C-2 position. The g-linolenic acid moiety is derived from animal fats, while the nervonic acid moiety is derived from fish oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C50H92NO8P None None None 2540.75 2119.59 2416.29 2897.71 2628.96 2573.5 2768.81 2639.59 2298.55 2370.35 2741.48 2813.62 2207.4 3041.83 2096.13 3485.23 2235.85 2554.78 1752.83 2717.5 2195.01 1968.07 2618.45 2009.21 2542.53 2440.73 1871.3 2242.04 2241.7 2873.33 2620.38 3678.91 2562.02 2215.25 1712.8 2162.23 2047.72 2745.75 1597.96 1974.27 5854.85 1695.13 868.1647419_MZ 3-Methylcrotonyl-CoA Un 1.0 None None None None 3-Methylcrotonyl-CoA is an essential metabolite for leucine metabolism, a substrate of 3-methylcrotonyl-CoA carboxylase (EC 6.4.1.4), a biotin-dependent mitochondrial enzyme in the catabolism of leucine. (OMIM 609010). C26H42N7O17P3S None None None 504.335 272.367 635.969 152.893 399.315 415.183 384.226 418.965 386.696 389.129 346.302 599.835 489.782 496.037 339.159 498.828 511.494 385.626 518.405 574.562 436.86 589.478 343.398 383.17 299.814 324.901 463.929 367.297 583.263 774.472 532.994 307.411 591.269 371.668 614.369 522.152 477.45 249.361 274.799 367.733 1729.75 471.923 873.2999017_MZ Hydroxymethylbilane Un 1.0 None None None None Hydroxymethylbilane is a molecule involved in the metabolism of porphyrin. In the third step, it is generated by the enzyme porphobilinogen deaminase , and in the next step the enzyme uroporphyrinogen III synthase converts it into uroporphyrinogen III. -- Wikipedia. C40H46N4O17 None None None 166.847 171.485 177.345 177.129 187.058 147.42 264.386 142.435 140.149 219.734 192.007 2350.85 193.08 228.418 476.417 69.5528 109.826 142.239 219.541 211.497 199.844 243.525 155.136 71.9816 426.297 184.613 222.301 480.783 108.011 318.789 260.563 287.881 254.391 140.806 162.07 238.176 89.2041 305.786 75.2133 104.294 874.5023870_MZ Phosphatidylserine (20:4(5Z_8Z_11Z_14Z)/22:6(4Z_7Z_10Z_13Z_16Z_19Z)) Un 1.0 None None None None PS(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PS(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of arachidonic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The arachidonic acid moiety is derived from animal fats and eggs, while the docosahexaenoic acid moiety is derived from fish oils. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE. C48H74NO10P None None None 22972.2 28433.8 30569.5 37742.4 47270.9 35676.7 32008.1 27315.6 34659.3 34847.6 45570.3 38862.6 19690.8 37031.2 31619.5 33799.3 22291.5 17441.0 23540.3 25067.5 23301.1 26251.5 36572.9 23705.2 31606.2 36104.3 31590.8 29523.8 24954.6 31057.6 32972.2 42673.7 39442.4 22092.4 22746.7 22030.7 25549.6 33483.7 17017.8 31715.4 21521.3 21279.3 875.7652432_MZ Tricaprylic glyceride (16:0/18:1(9Z)/18:2(9Z_12Z))[iso6] Un 1.0 None None None None TG(16:0/18:1(9Z)/18:2(9Z,12Z))[iso6] is a monooleic acid triglyceride. Triglycerides (TGs) are also known as triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.e. fatty acid tri-esters of glycerol). TGs may be divided into three general types with respect to their acyl substituents. They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. TG(16:0/18:1(9Z)/18:2(9Z,12Z))[iso6], in particular, consists of one chain of palmitic acid at the C-1 position, one chain of oleic acid at the C-2 position and one chain of linoleic acid at the C-3 position. TGs are the main constituent of vegetable oil and animal fats. TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) with the help of lipases and bile secretions, which can then move into blood vessels. The triglycerides are rebuilt in the blood from their fragments and become constituents of lipoproteins, which deliver the fatty acids to and from fat cells among other functions. Various tissues can release the free fatty acids and take them up as a source of energy. Fat cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain cannot utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when it is broken down. (www.cyberlipid.org, www.wikipedia.org)TAGs can serve as fatty acid stores in all cells, but primarily in adipocytes of adipose tissue. The major building block for the synthesis of triacylglycerides, in non-adipose tissue, is glycerol. Adipocytes lack glycerol kinase and so must use another route to TAG synthesis. Specifically, dihydroxyacetone phosphate (DHAP), which is produced during glycolysis, is the precursor for TAG synthesis in adipose tissue. DHAP can also serve as a TAG precursor in non-adipose tissues, but does so to a much lesser extent than glycerol. The use of DHAP for the TAG backbone depends on whether the synthesis of the TAGs occurs in the mitochondria and ER or the ER and the peroxisomes. The ER/mitochondria pathway requires the action of glycerol-3-phosphate dehydrogenase to convert DHAP to glycerol-3-phosphate. Glycerol-3-phosphate acyltransferase then esterifies a fatty acid to glycerol-3-phosphate thereby generating lysophosphatidic acid. The ER/peroxisome reaction pathway uses the peroxisomal enzyme DHAP acyltransferase to acylate DHAP to acyl-DHAP which is then reduced by acyl-DHAP reductase. The fatty acids that are incorporated into TAGs are activated to acyl-CoAs through the action of acyl-CoA synthetases. Two molecules of acyl-CoA are esterified to glycerol-3-phosphate to yield 1,2-diacylglycerol phosphate (also known as phosphatidic acid). The phosphate is then removed by phosphatidic acid phosphatase (PAP1), to generate 1,2-diacylglycerol. This diacylglycerol serves as the substrate for addition of the third fatty acid to make TAG. Intestinal monoacylglycerols, derived from dietary fats, can also serve as substrates for the synthesis of 1,2-diacylglycerols. C55H100O6 None None None 2087.61 987.638 963.244 1687.43 1394.9 1146.21 2315.16 2833.08 1201.55 830.177 1445.83 1083.0 3487.17 2488.08 1084.28 1437.96 1271.15 7226.62 770.974 3053.86 999.856 697.37 1118.04 2699.48 1590.9 961.43 963.287 2731.14 755.383 715.775 1758.27 2442.38 1734.91 901.798 952.026 2219.42 1312.16 1203.4 1933.28 989.661 4045.34 2989.28 876.5126626_MZ Phosphatidylserine (20:3(8Z_11Z_14Z)/22:6(4Z_7Z_10Z_13Z_16Z_19Z)) Un 1.0 None None None None C48H76NO10P None None None 28742.7 36071.7 34435.0 46371.2 42724.0 36025.6 36173.3 32716.5 41455.6 35703.0 50175.2 47953.3 21992.4 39257.7 31600.7 36937.1 34014.3 24799.4 26546.9 27422.6 30732.1 33390.1 40041.6 26128.2 37671.1 37889.0 37697.2 38904.7 33652.8 36239.1 40019.3 39845.4 39500.0 27318.7 29951.8 31089.4 28342.8 37918.5 18650.5 34841.2 23472.2 26228.1 876.6809526_MZ Phosphatidylcholine with formula C52H96NO7P Un 1.0 None None None None C52H96NO7P None None None 2748.24 3607.34 2398.12 2280.95 1992.58 3597.4 3206.88 2602.31 2592.69 2183.07 2905.51 4580.93 2205.71 2378.11 2083.44 3507.08 2864.96 3884.12 2424.07 4014.88 2438.6 1912.67 2615.42 2430.12 2924.7 2586.37 1885.22 3122.03 1950.8 2975.97 3607.73 4084.68 2664.28 2703.55 1225.24 1973.28 2048.14 3167.15 1684.61 2049.3 2063.14 1610.09 877.7243284_MZ Tricaprylic glyceride with formula C57H98O6 Un 1.0 None None None None TG(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))[iso3] is a dipalmitic acid triglyceride. Triglycerides (TGs) are also known as triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.e. fatty acid tri-esters of glycerol). TGs may be divided into three general types with respect to their acyl substituents. They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. TG(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))[iso3], in particular, consists of one chain of palmitic acid at the C-1 position, one chain of palmitic acid at the C-2 position and one chain of docosahexaenoic acid at the C-3 position. TGs are the main constituent of vegetable oil and animal fats. TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) with the help of lipases and bile secretions, which can then move into blood vessels. The triglycerides are rebuilt in the blood from their fragments and become constituents of lipoproteins, which deliver the fatty acids to and from fat cells among other functions. Various tissues can release the free fatty acids and take them up as a source of energy. Fat cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain cannot utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when it is broken down. (www.cyberlipid.org, www.wikipedia.org)TAGs can serve as fatty acid stores in all cells, but primarily in adipocytes of adipose tissue. The major building block for the synthesis of triacylglycerides, in non-adipose tissue, is glycerol. Adipocytes lack glycerol kinase and so must use another route to TAG synthesis. Specifically, dihydroxyacetone phosphate (DHAP), which is produced during glycolysis, is the precursor for TAG synthesis in adipose tissue. DHAP can also serve as a TAG precursor in non-adipose tissues, but does so to a much lesser extent than glycerol. The use of DHAP for the TAG backbone depends on whether the synthesis of the TAGs occurs in the mitochondria and ER or the ER and the peroxisomes. The ER/mitochondria pathway requires the action of glycerol-3-phosphate dehydrogenase to convert DHAP to glycerol-3-phosphate. Glycerol-3-phosphate acyltransferase then esterifies a fatty acid to glycerol-3-phosphate thereby generating lysophosphatidic acid. The ER/peroxisome reaction pathway uses the peroxisomal enzyme DHAP acyltransferase to acylate DHAP to acyl-DHAP which is then reduced by acyl-DHAP reductase. The fatty acids that are incorporated into TAGs are activated to acyl-CoAs through the action of acyl-CoA synthetases. Two molecules of acyl-CoA are esterified to glycerol-3-phosphate to yield 1,2-diacylglycerol phosphate (also known as phosphatidic acid). The phosphate is then removed by phosphatidic acid phosphatase (PAP1), to generate 1,2-diacylglycerol. This diacylglycerol serves as the substrate for addition of the third fatty acid to make TAG. Intestinal monoacylglycerols, derived from dietary fats, can also serve as substrates for the synthesis of 1,2-diacylglycerols. C57H98O6 None None None 694.705 1120.56 610.148 2023.3 840.61 698.701 1403.29 1321.29 737.605 946.794 679.817 680.645 241.464 542.176 836.864 1133.88 3243.88 592.423 1058.55 962.962 554.911 213.257 884.923 733.898 1106.54 289.926 729.787 705.965 166.985 982.774 1472.36 2492.44 464.227 819.297 300.773 536.817 589.298 518.619 883.661 858.573 1485.82 589.136 878.2130436_MZ 2-Methylhexanoyl-CoA Un 1.0 None None None None 2-Methylhexanoyl-CoA is a coenzyme, notable for its role in the synthesis and oxidation of fatty acids, and the oxidation of pyruvate in the citric acid cycle. It is adapted from cysteamine, pantothenate, and adenosine triphosphate. This compound is formed by 2-Methylhexanoic acid reacting with thiol group of CoA molecules. C28H48N7O17P3S None None None 171.73 293.55 380.887 229.662 145.812 118.837 68.6532 83.9751 155.434 317.169 250.385 1590.09 371.12 180.733 396.024 240.077 163.923 252.392 175.759 178.868 271.911 221.08 250.319 160.987 209.318 366.396 384.684 256.082 381.155 64.8804 116.295 281.896 227.745 330.947 260.414 193.777 302.999 258.22 156.905 319.385 176.165 878.4837887_MZ Phosphatidylserine with formula C50H74NO10P Un 1.0 None None None None PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of docosahexaenoic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The docosahexaenoic acid moiety is derived from fish oils, while the docosahexaenoic acid moiety is derived from fish oils. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE. C50H74NO10P None None None 7390.63 9641.85 10026.0 13085.9 16328.5 12462.6 10112.0 7579.45 11451.5 11135.8 14737.4 15476.4 6754.87 11327.0 11065.5 12150.6 7556.09 4566.89 7794.52 9483.2 9137.06 10494.9 11949.7 8549.05 12593.1 12422.3 11689.3 10021.0 9034.93 10259.6 10808.8 13895.9 11675.1 7621.76 9891.76 8666.16 8008.93 15904.0 5182.24 10379.3 5598.18 6780.33 878.7104477_MZ Phosphatidylcholine (o-22:1(13Z)/22:3(10Z_13Z_16Z)) Un 1.0 None None None None PC(o-22:1(13Z)/22:3(10Z,13Z,16Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(o-22:1(13Z)/22:3(10Z,13Z,16Z)), in particular, consists of one chain of Erucyl alcohol at the C-1 position and one chain of (10Z,13Z,16Z-docosatrienoyl) at the C-2 position. The Erucyl alcohol moiety is derived from Rapeseed oil, while the (10Z,13Z,16Z-docosatrienoyl) moiety is derived from fish oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C52H98NO7P None None None 154.738 415.627 194.464 680.25 353.986 258.666 349.03 370.175 211.343 630.529 256.967 482.517 182.184 354.8 714.338 619.985 423.281 252.569 312.494 223.408 218.059 236.544 143.508 756.851 315.011 281.133 304.695 108.656 380.737 391.151 2368.51 248.021 297.387 198.747 150.99 267.788 352.239 352.618 324.643 6041.13 134.308 879.7416331_MZ Tricaprylic glyceride (16:0/18:1(9Z)/20:4(5Z_8Z_11Z_14Z))[iso6] Un 1.0 None None None None TG(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))[iso6] is a monoarachidonic acid triglyceride. Triglycerides (TGs) are also known as triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.e. fatty acid tri-esters of glycerol). TGs may be divided into three general types with respect to their acyl substituents. They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. TG(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))[iso6], in particular, consists of one chain of palmitic acid at the C-1 position, one chain of oleic acid at the C-2 position and one chain of arachidonic acid at the C-3 position. TGs are the main constituent of vegetable oil and animal fats. TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) with the help of lipases and bile secretions, which can then move into blood vessels. The triglycerides are rebuilt in the blood from their fragments and become constituents of lipoproteins, which deliver the fatty acids to and from fat cells among other functions. Various tissues can release the free fatty acids and take them up as a source of energy. Fat cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain cannot utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when it is broken down. (www.cyberlipid.org, www.wikipedia.org)TAGs can serve as fatty acid stores in all cells, but primarily in adipocytes of adipose tissue. The major building block for the synthesis of triacylglycerides, in non-adipose tissue, is glycerol. Adipocytes lack glycerol kinase and so must use another route to TAG synthesis. Specifically, dihydroxyacetone phosphate (DHAP), which is produced during glycolysis, is the precursor for TAG synthesis in adipose tissue. DHAP can also serve as a TAG precursor in non-adipose tissues, but does so to a much lesser extent than glycerol. The use of DHAP for the TAG backbone depends on whether the synthesis of the TAGs occurs in the mitochondria and ER or the ER and the peroxisomes. The ER/mitochondria pathway requires the action of glycerol-3-phosphate dehydrogenase to convert DHAP to glycerol-3-phosphate. Glycerol-3-phosphate acyltransferase then esterifies a fatty acid to glycerol-3-phosphate thereby generating lysophosphatidic acid. The ER/peroxisome reaction pathway uses the peroxisomal enzyme DHAP acyltransferase to acylate DHAP to acyl-DHAP which is then reduced by acyl-DHAP reductase. The fatty acids that are incorporated into TAGs are activated to acyl-CoAs through the action of acyl-CoA synthetases. Two molecules of acyl-CoA are esterified to glycerol-3-phosphate to yield 1,2-diacylglycerol phosphate (also known as phosphatidic acid). The phosphate is then removed by phosphatidic acid phosphatase (PAP1), to generate 1,2-diacylglycerol. This diacylglycerol serves as the substrate for addition of the third fatty acid to make TAG. Intestinal monoacylglycerols, derived from dietary fats, can also serve as substrates for the synthesis of 1,2-diacylglycerols. C57H100O6 None None None 670.049 1022.46 607.111 2210.32 1173.78 705.348 1608.49 1474.94 764.711 926.035 582.395 591.771 467.414 794.822 882.517 1147.52 2749.53 477.584 1185.13 901.208 551.885 248.855 742.352 878.929 892.729 414.403 657.272 806.257 258.916 986.883 1520.02 1985.77 602.682 911.659 284.4 631.604 434.513 581.054 845.56 1027.76 2115.32 670.732 881.7569201_MZ Tricaprylic glyceride (16:0/18:0/20:4(5Z_8Z_11Z_14Z))[iso6] Un 1.0 None None None None TG(16:0/18:0/20:4(5Z,8Z,11Z,14Z))[iso6] is a monoarachidonic acid triglyceride. Triglycerides (TGs) are also known as triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.e. fatty acid tri-esters of glycerol). TGs may be divided into three general types with respect to their acyl substituents. They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. TG(16:0/18:0/20:4(5Z,8Z,11Z,14Z))[iso6], in particular, consists of one chain of palmitic acid at the C-1 position, one chain of stearic acid at the C-2 position and one chain of arachidonic acid at the C-3 position. TGs are the main constituent of vegetable oil and animal fats. TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) with the help of lipases and bile secretions, which can then move into blood vessels. The triglycerides are rebuilt in the blood from their fragments and become constituents of lipoproteins, which deliver the fatty acids to and from fat cells among other functions. Various tissues can release the free fatty acids and take them up as a source of energy. Fat cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain cannot utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when it is broken down. (www.cyberlipid.org, www.wikipedia.org)TAGs can serve as fatty acid stores in all cells, but primarily in adipocytes of adipose tissue. The major building block for the synthesis of triacylglycerides, in non-adipose tissue, is glycerol. Adipocytes lack glycerol kinase and so must use another route to TAG synthesis. Specifically, dihydroxyacetone phosphate (DHAP), which is produced during glycolysis, is the precursor for TAG synthesis in adipose tissue. DHAP can also serve as a TAG precursor in non-adipose tissues, but does so to a much lesser extent than glycerol. The use of DHAP for the TAG backbone depends on whether the synthesis of the TAGs occurs in the mitochondria and ER or the ER and the peroxisomes. The ER/mitochondria pathway requires the action of glycerol-3-phosphate dehydrogenase to convert DHAP to glycerol-3-phosphate. Glycerol-3-phosphate acyltransferase then esterifies a fatty acid to glycerol-3-phosphate thereby generating lysophosphatidic acid. The ER/peroxisome reaction pathway uses the peroxisomal enzyme DHAP acyltransferase to acylate DHAP to acyl-DHAP which is then reduced by acyl-DHAP reductase. The fatty acids that are incorporated into TAGs are activated to acyl-CoAs through the action of acyl-CoA synthetases. Two molecules of acyl-CoA are esterified to glycerol-3-phosphate to yield 1,2-diacylglycerol phosphate (also known as phosphatidic acid). The phosphate is then removed by phosphatidic acid phosphatase (PAP1), to generate 1,2-diacylglycerol. This diacylglycerol serves as the substrate for addition of the third fatty acid to make TAG. Intestinal monoacylglycerols, derived from dietary fats, can also serve as substrates for the synthesis of 1,2-diacylglycerols. C57H102O6 None None None 1035.8 1199.55 724.151 1998.26 1382.31 748.86 1761.12 2022.19 899.673 801.801 713.588 802.234 1207.94 1302.53 1115.75 1704.7 2125.69 795.872 1248.48 1286.54 811.618 357.776 793.929 1160.8 1107.61 515.863 813.343 803.303 318.295 1015.63 1944.93 2670.7 752.443 1017.12 568.297 804.283 636.734 756.505 993.14 1031.32 2993.94 879.138 883.5332733_MZ Phosphatidylinositol16:0/22:5(4Z_7Z_10Z_13Z_16Z)) Un 1.0 None None None None PI(16:0/22:5(4Z,7Z,10Z,13Z,16Z)) is a phosphatidylinositol. Phosphatidylinositols are important lipids, both as a key membrane constituent and as a participant in essential metabolic processes, both directly and via a number of metabolites. Phosphatidylinositols are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to inositol (hexahydroxycyclohexane). Phosphatidylinositols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 18 and 20 carbons are the most common. PI(16:0/22:5(4Z,7Z,10Z,13Z,16Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of docosapentaenoic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the docosapentaenoic acid moiety is derived from animal fats and brain. In most organisms, the stereochemical form of the last is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial. Phosphatidylinositol is especially abundant in brain tissue, where it can amount to 10% of the phospholipids, but it is present in all tissues and cell types. There is usually less of it than of phosphatidylcholine, phosphatidylethanolamine and phosphatidylserine. In animal tissues, phosphatidylinositol is the primary source of the arachidonic acid required for biosynthesis of eicosanoids, including prostaglandins, via the action of the enzyme phospholipase A2. Phosphatidylinositol can be phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated by a specific kinase. Seven different isomers are known, but the most important in both quantitative and biological terms are phosphatidylinositol 4-phosphate and phosphatidylinositol 4,5-bisphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PIs contain almost exclusively stearic acid at carbon 1 and arachidonic acid at carbon 2. PIs composed exclusively of non-phosphorylated inositol exhibit a net charge of -1 at physiological pH. Molecules with phosphorylated inositol (such as PIP, PIP2, PIP3, etc.) are termed polyphosphoinositides. The polyphosphoinositides are important intracellular transducers of signals emanating from the plasma membrane. The synthesis of PI involves CDP-activated 1,2-diacylglycerol condensation with myo-inositol. C47H81O13P None None None 251734.0 154142.0 166023.0 221618.0 402085.0 172679.0 294851.0 332682.0 258038.0 121691.0 264937.0 237804.0 363714.0 311777.0 153546.0 184784.0 291038.0 213796.0 145117.0 201972.0 247676.0 209655.0 324684.0 206454.0 272628.0 343876.0 195822.0 204381.0 240541.0 188054.0 230065.0 193409.0 213992.0 213486.0 160095.0 310585.0 230893.0 211807.0 114447.0 213637.0 252511.0 243764.0 885.5496472_MZ Phosphatidylinositol16:0/22:4(10Z_13Z_16Z_19Z)) Un 1.0 None None None None C47H83O13P None None None 3975470.0 4073890.0 3745600.0 4432790.0 4460330.0 3054340.0 5897970.0 4983150.0 4140820.0 2803860.0 4624960.0 4750380.0 6180250.0 3584220.0 3090240.0 2959390.0 5367480.0 4759320.0 3599310.0 5719270.0 3639560.0 2848380.0 3798090.0 3544550.0 4383130.0 3588940.0 2828080.0 4943240.0 3218010.0 3372210.0 4705690.0 3316590.0 4148750.0 3169000.0 1895750.0 3332740.0 3379860.0 2990320.0 3408340.0 3873310.0 5383310.0 3976990.0 888.6096410_MZ 3-O-Sulfogalactosylceramide (d18:1/24:1(15Z)) Un 1.0 None None None None C48H91NO11S None None None 32029.6 27066.6 24888.1 26879.9 29678.3 27224.8 49834.9 34848.9 26462.0 18703.4 32973.6 33088.1 51430.1 30399.2 19043.8 28387.3 27313.4 37597.3 21691.5 49443.2 24032.5 21159.4 26948.7 26103.0 30168.4 30956.9 20488.3 34617.4 25090.3 24565.4 32545.6 24912.0 31824.1 31759.3 15905.3 25623.3 26200.9 30161.3 19990.5 23788.4 44862.4 27739.9 888.6403162_MZ Galabiosylceramide (d18:1/18:0) Un 1.0 None None None None Galabiosylceramide is a non-acidic diglycosphingolipids, i.e. a sphingolipid with two or more carbohydrate moieties attached to a ceramide unit. It is a vital component of cellular membranes of most eukaryotic organisms and some bacteria. Its abundance relative to other lipids is usually low other than in epithelial and neuronal cells. Galabiosylceramide has also been found in small amounts in kidney and pancreas, for example. Galabiosylceramide is one of the lipids that accumulates in excessive amounts in Fabry's disease. It is the precursor of the gala series of oligoglycosylceramides.An animal tissues, biosynthesis involves addition of a second monosaccharides unit from the appropriate sugar nucleotide to a monoglycosylceramide, catalysed by a glycosyl transferase, in the lumen of the Golgi apparatus. Glycolipids are important components of the body's immune defense system, either in haptenic reactivity or in antibody-producing potency, i.e. as cellular immunogens or antigens. Certain glycolipids are involved in the antigenicity of blood group determinants, while others bind to specific toxins or bacteria. Some also function as receptors for cellular recognition, and they can be specific for particular tissues or tumours. C48H91NO13 None None None 12180.4 10777.0 10231.7 12307.7 10447.8 9999.67 18670.6 12778.8 10778.2 7734.77 12905.8 15400.0 17717.0 11686.2 7384.24 12455.2 10504.8 14735.4 7905.32 19813.2 11230.9 8112.9 10879.4 9142.0 11929.9 11682.4 7721.69 15957.9 9661.83 10865.8 12269.9 11357.1 11983.3 10446.9 6914.09 9432.83 11866.4 11035.5 6796.84 8851.19 16302.3 9535.74 890.6365087_MZ 3-O-Sulfogalactosylceramide (d18:1/24:0) Un 1.0 None None None None 3-O-Sulfogalactosylceramide is an acidic, sulfated glycosphingolipid, often known as sulfatide. This lipid occurs in membranes of various cell types, but is found in particularly high concentrations in myelin where it constitutes 3-4% of total membrane lipids. This lipid is synthesized primarily in the oligodendrocytes in the central nervous system. Accumulation of this lipid in the lysosomes is a characteristic of metachromatic leukodystrophy, a lysosomal storage disease caused by the deficiency of arylsulfatase A. Alterations in sulfatide metabolism, trafficking, and homeostasis are present in the earliest clinically recognizable stages of Alzheimer's disease. Cerebrosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Cerebrosides have a single sugar group linked to ceramide. The most common are galactocerebrosides (containing galactose), the least common are glucocerebrosides (containing glucose). Galactocerebrosides are found predominantly in neuronal cell membranes. In contrast glucocerebrosides are not normally found in membranes. Instead, they are typically intermediates in the synthesis or degradation of more complex glycosphingolipids. Galactocerebrosides are synthesized from ceramide and UDP-galactose. Excess lysosomal accumulation of glucocerebrosides is found in Gaucher disease. Sulfatides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Sulfatides are the sulfuric acid esters of galactocerebrosides. They are synthesized from galactocerebrosides and activated sulfate, 3'-phosphoadenosine 5'-phosphosulfate (PAPS). C48H93NO11S None None None 6697.5 5923.23 6270.83 6953.99 7367.54 6085.09 7683.15 7130.26 6432.82 6404.58 7761.26 8044.62 7903.73 7425.17 5197.89 7517.96 6206.45 8698.36 4966.33 7969.39 6623.28 5462.39 6590.53 5546.97 7229.11 7222.45 4744.09 7506.64 6500.17 6650.79 6881.89 8756.66 7311.44 6344.0 4445.76 5713.24 5887.64 8051.38 4949.95 5721.48 7573.39 5299.42 897.5117641_MZ Phosphatidylglycerolphosphate (16:0/22:4(7Z_10Z_13Z_16Z)) Un 1.0 None None None None PGP(16:0/22:4(7Z,10Z,13Z,16Z)) is a phosphatidylglycerolphosphate or glycerophospholipid (PGP or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site followed by another phosphate moiety. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PGP(16:0/22:4(7Z,10Z,13Z,16Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of adrenic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the adrenic acid moiety is derived from animal fats. Phosphatidylglycerolphosphate is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of Phosphatidylglycerolphosphate increases during fetal development. Phosphatidylglycerolphosphate may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGPs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PGP also serves as a precursor for the synthesis of cardiolipin. PGP is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. C44H80O13P2 None None None 13200.7 17310.2 15102.2 21853.0 22251.5 17150.0 17595.9 15910.2 18816.7 17478.3 23440.6 23654.2 10001.1 17242.2 15204.9 16986.8 15437.8 9017.8 11927.3 12892.0 14590.1 16673.9 19653.9 12409.3 17375.0 20254.3 17717.4 18320.1 15829.4 17435.4 19643.6 14949.1 18340.7 13114.2 14255.8 14508.2 13905.2 18383.1 9406.15 15875.3 10526.4 11929.3 902.2037143_MZ 2,6-Dimethylheptanoyl-CoA Un 1.0 None None None None 2,6 dimethylheptanoyl-CoA is a metabolite of pristanic acid,which itself is the alpha-oxidation product of phytanic acid.(PMID: 9714723). C30H48N7O17P3S None None None 227.805 624.583 424.21 216.511 309.28 288.588 159.274 300.997 181.392 183.665 257.669 1901.11 131.27 398.438 238.144 118.602 130.639 318.695 303.63 307.281 528.119 430.757 183.913 219.237 355.828 306.217 411.72 408.395 421.735 434.977 441.009 191.417 472.463 150.911 505.442 377.834 347.148 189.482 262.124 255.04 844.588 240.672 902.6855359_MZ Phosphatidylethanolamine (22:1(13Z)/24:1(15Z)) Un 1.0 None None None None PE(22:1(13Z)/24:1(15Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(22:1(13Z)/24:1(15Z)), in particular, consists of one chain of erucic acid at the C-1 position and one chain of nervonic acid at the C-2 position. The erucic acid moiety is derived from seed oils and avocados, while the nervonic acid moiety is derived from fish oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. C51H98NO8P None None None 2049.28 2001.91 1587.02 1802.89 2181.13 1752.18 1939.07 2265.1 1990.64 1570.28 2225.21 2896.84 1677.85 1842.44 1408.55 2096.68 2000.58 2321.51 1376.32 2206.57 1739.74 1674.26 1893.18 1631.11 2080.25 1955.46 1271.39 2099.13 1374.31 1931.52 1830.18 2337.66 1738.58 1786.99 1091.26 1762.97 1517.96 1837.24 1089.75 1462.61 1439.85 1274.11 906.6285579_MZ Galabiosylceramide (d18:1/9Z-18:1) Un 1.0 None None None None Galabiosylceramide is a non-acidic diglycosphingolipids, i.e. a sphingolipid with two or more carbohydrate moieties attached to a ceramide unit. It is a vital component of cellular membranes of most eukaryotic organisms and some bacteria. Its abundance relative to other lipids is usually low other than in epithelial and neuronal cells. Galabiosylceramide is one of the lipids that accumulate in excessive amounts in Fabry's disease. Fabry disease (FD) is an X-linked inborn error of glycosphingolipid (GSL) metabolism, caused by a deficiency of the lysosomal alpha-galactosidase A, which results in high levels in lysosomes and biological fluids of galabiosylceramide, also known as digalactosylceramide (Ga2). In Fabry disease, accumulation of galabiosylceramide is observed by coloration methods associated to optic or electron microscopy or more recently, with imaging mass spectrometry. Galabiosylceramide is the precursor of a series of oligoglycosylceramides. In animal tissues, biosynthesis involves addition of a second monosaccharide unit from the appropriate sugar nucleotide to a monoglycosylceramide, catalysed by a glycosyl transferase, in the lumen of the Golgi apparatus. Glycolipids are important components of the body's immune defense system, either in haptenic reactivity or in antibody-producing potency, i.e. as cellular immunogens or antigens. (PMID: 15702404, 15959771, 16324673, 14761135). C48H89NO13, Lactosyceramide (d18:1/18:1(9Z)) None None None 10759.8 9001.83 11294.3 8630.33 10487.1 8200.31 11469.7 10107.9 9965.74 7673.1 12298.8 11669.0 12365.1 10413.0 7919.28 8518.99 9274.07 14537.5 8026.26 12103.3 9371.08 9388.33 9453.24 8600.63 10103.9 10358.9 6765.68 12384.1 10007.8 8984.65 9111.94 9895.72 12151.4 8503.75 7570.73 9371.51 8663.02 14341.5 8571.53 9428.7 11143.0 8883.65 906.7266778_MZ Phosphatidylethanolamine (22:0/24:0) Un 1.0 None None None None PE(22:0/24:0) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(22:0/24:0), in particular, consists of one chain of behenic acid at the C-1 position and one chain of lignoceric acid at the C-2 position. The behenic acid moiety is derived from groundnut oil, while the lignoceric acid moiety is derived from groundnut oil. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. C51H102NO8P None None None 1002.62 2952.31 1174.9 4229.5 4380.75 2637.11 2958.54 1706.42 2858.64 2166.33 2554.75 3245.37 527.543 2110.42 4225.06 2265.46 3406.77 649.567 2186.67 937.534 1315.72 935.766 1991.77 2147.46 2245.04 1013.65 2896.48 1676.37 485.065 2231.84 2019.49 3249.91 2089.03 1369.41 823.965 1076.54 1099.84 2379.62 867.407 2709.57 2050.17 994.941 907.4609518_MZ Phosphatidylinositol Phosphate with formula C41H78O16P2 Un 1.0 None None None None PIP(16:1(9Z)/18:0) is a phosphatidylinositol phosphate. Phosphatidylinositol phosphates are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to a phosphorylated inositol (hexahydroxycyclohexane). Phosphatidylinositol phosphates are generated from phosphatidylinositols, which are phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated. Phosphatidylinositols phosphates can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 18 and 20 carbons are the most common. PIP(16:1(9Z)/18:0), in particular, consists of one chain of palmitoleic acid at the C-1 position and one chain of stearic acid at the C-2 position. The palmitoleic acid moiety is derived from animal fats and vegetable oils, while the stearic acid moiety is derived from animal fats, coco butter and sesame oil. The most important phosphatidylinositol phosphate in both quantitative and biological terms is phosphatidylinositol 4-phosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes. Phosphatidylinositols phosphates are usually present at low levels only in tissues, typically at about 1 to 3% of the concentration of phosphatidylinositol. C41H78O16P2 None None None 4827.52 5964.29 6006.4 7399.96 11001.2 7275.02 6911.98 5377.09 7095.71 6683.31 9285.2 8900.48 3967.22 7237.11 7036.41 7599.65 4780.85 3610.81 5064.45 5246.33 5031.53 6387.38 7130.31 5280.31 6418.96 7934.5 7113.85 6456.9 5459.83 5514.26 6473.89 8524.95 7097.35 4827.9 5311.11 4948.21 5204.21 7589.49 3232.99 6909.77 4366.43 4748.1 907.5751321_MZ Phosphatidylinositol16:0/22:3(10Z_13Z_16Z)) Un 1.0 None None None None PI(16:0/22:3(10Z,13Z,16Z)) is a phosphatidylinositol. Phosphatidylinositols are important lipids, both as a key membrane constituent and as a participant in essential metabolic processes, both directly and via a number of metabolites. Phosphatidylinositols are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to inositol (hexahydroxycyclohexane). Phosphatidylinositols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 18 and 20 carbons are the most common. PI(16:0/22:3(10Z,13Z,16Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of (10Z,13Z,16Z-docosatrienoyl) at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the (10Z,13Z,16Z-docosatrienoyl) moiety is derived from fish oils. In most organisms, the stereochemical form of the last is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial. Phosphatidylinositol is especially abundant in brain tissue, where it can amount to 10% of the phospholipids, but it is present in all tissues and cell types. There is usually less of it than of phosphatidylcholine, phosphatidylethanolamine and phosphatidylserine. In animal tissues, phosphatidylinositol is the primary source of the arachidonic acid required for biosynthesis of eicosanoids, including prostaglandins, via the action of the enzyme phospholipase A2. Phosphatidylinositol can be phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated by a specific kinase. Seven different isomers are known, but the most important in both quantitative and biological terms are phosphatidylinositol 4-phosphate and phosphatidylinositol 4,5-bisphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PIs contain almost exclusively stearic acid at carbon 1 and arachidonic acid at carbon 2. PIs composed exclusively of non-phosphorylated inositol exhibit a net charge of -1 at physiological pH. Molecules with phosphorylated inositol (such as PIP, PIP2, PIP3, etc.) are termed polyphosphoinositides. The polyphosphoinositides are important intracellular transducers of signals emanating from the plasma membrane. The synthesis of PI involves CDP-activated 1,2-diacylglycerol condensation with myo-inositol. C47H85O13P None None None 78932.6 56960.1 87070.0 59695.4 86406.5 53792.4 81372.6 60230.4 76829.6 54332.2 82413.3 77773.3 100511.0 75623.1 59989.5 42103.2 82036.7 107870.0 62333.3 74036.1 73503.6 70773.6 69244.5 60686.5 73903.6 77590.1 55156.5 91796.6 84248.1 62292.2 66652.3 42653.8 91016.7 60826.8 59710.3 85969.0 66707.5 74131.5 61497.4 68793.5 89116.4 75372.2 909.5479267_MZ Phosphatidylinositol18:0/22:6(4Z_7Z_10Z_13Z_16Z_19Z)) Un 1.0 None None None None PI(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a phosphatidylinositol. Phosphatidylinositols are important lipids, both as a key membrane constituent and as a participant in essential metabolic processes, both directly and via a number of metabolites. Phosphatidylinositols are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to inositol (hexahydroxycyclohexane). Phosphatidylinositols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 18 and 20 carbons are the most common. PI(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the docosahexaenoic acid moiety is derived from fish oils. In most organisms, the stereochemical form of the last is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial. Phosphatidylinositol is especially abundant in brain tissue, where it can amount to 10% of the phospholipids, but it is present in all tissues and cell types. There is usually less of it than of phosphatidylcholine, phosphatidylethanolamine and phosphatidylserine. In animal tissues, phosphatidylinositol is the primary source of the arachidonic acid required for biosynthesis of eicosanoids, including prostaglandins, via the action of the enzyme phospholipase A2. Phosphatidylinositol can be phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated by a specific kinase. Seven different isomers are known, but the most important in both quantitative and biological terms are phosphatidylinositol 4-phosphate and phosphatidylinositol 4,5-bisphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PIs contain almost exclusively stearic acid at carbon 1 and arachidonic acid at carbon 2. PIs composed exclusively of non-phosphorylated inositol exhibit a net charge of -1 at physiological pH. Molecules with phosphorylated inositol (such as PIP, PIP2, PIP3, etc.) are termed polyphosphoinositides. The polyphosphoinositides are important intracellular transducers of signals emanating from the plasma membrane. The synthesis of PI involves CDP-activated 1,2-diacylglycerol condensation with myo-inositol. C49H83O13P None None None 55585.6 48193.8 43775.4 52587.5 60074.2 55339.3 70697.4 93044.0 46100.7 46150.8 72702.9 58816.2 75815.2 61833.8 45224.4 45844.7 59297.7 76231.6 34655.2 61509.7 40706.2 38545.0 56067.4 44576.6 53072.7 67785.8 37551.2 63267.0 43541.4 51985.1 56178.4 43963.5 55586.8 49196.6 27418.0 46350.9 61344.4 54984.6 47063.6 55167.0 73303.8 56105.4 911.5671268_MZ Phosphatidylinositol18:0/22:5(4Z_7Z_10Z_13Z_16Z)) Un 1.0 None None None None PI(18:0/22:5(4Z,7Z,10Z,13Z,16Z)) is a phosphatidylinositol. Phosphatidylinositols are important lipids, both as a key membrane constituent and as a participant in essential metabolic processes, both directly and via a number of metabolites. Phosphatidylinositols are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to inositol (hexahydroxycyclohexane). Phosphatidylinositols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 18 and 20 carbons are the most common. PI(18:0/22:5(4Z,7Z,10Z,13Z,16Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of docosapentaenoic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the docosapentaenoic acid moiety is derived from animal fats and brain. In most organisms, the stereochemical form of the last is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial. Phosphatidylinositol is especially abundant in brain tissue, where it can amount to 10% of the phospholipids, but it is present in all tissues and cell types. There is usually less of it than of phosphatidylcholine, phosphatidylethanolamine and phosphatidylserine. In animal tissues, phosphatidylinositol is the primary source of the arachidonic acid required for biosynthesis of eicosanoids, including prostaglandins, via the action of the enzyme phospholipase A2. Phosphatidylinositol can be phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated by a specific kinase. Seven different isomers are known, but the most important in both quantitative and biological terms are phosphatidylinositol 4-phosphate and phosphatidylinositol 4,5-bisphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PIs contain almost exclusively stearic acid at carbon 1 and arachidonic acid at carbon 2. PIs composed exclusively of non-phosphorylated inositol exhibit a net charge of -1 at physiological pH. Molecules with phosphorylated inositol (such as PIP, PIP2, PIP3, etc.) are termed polyphosphoinositides. The polyphosphoinositides are important intracellular transducers of signals emanating from the plasma membrane. The synthesis of PI involves CDP-activated 1,2-diacylglycerol condensation with myo-inositol. C49H85O13P None None None 39002.2 30894.7 32944.1 32369.2 44857.7 41340.1 50904.4 61852.1 30788.1 26548.7 44938.9 37923.8 58949.2 48715.4 27144.9 31153.2 37333.0 50953.0 24764.5 51133.8 30848.6 28331.3 38071.2 35830.9 35406.2 42133.2 28620.4 42395.2 34181.9 32881.2 36134.6 25514.7 43415.0 31308.2 20524.6 34811.2 37756.2 32324.7 29974.4 36394.1 54997.7 39804.6 912.6858839_MZ Phosphatidylcholine (20:3(5Z_8Z_11Z)/24:1(15Z)) Un 1.0 None None None None PC(20:3(5Z,8Z,11Z)/24:1(15Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(20:3(5Z,8Z,11Z)/24:1(15Z)), in particular, consists of one chain of mead acid at the C-1 position and one chain of nervonic acid at the C-2 position. The mead acid moiety is derived from fish oils, liver and kidney, while the nervonic acid moiety is derived from fish oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C52H96NO8P None None None 1546.34 2072.58 2137.88 2747.14 1729.18 1485.39 2409.15 1467.12 1535.33 1211.09 1818.62 2529.48 1790.48 1472.62 1455.92 2107.71 2126.53 1536.52 1535.19 2159.0 1605.06 1037.88 1889.05 1410.49 1850.33 1606.55 1441.33 1768.87 1122.96 1740.47 2168.86 2947.45 1721.77 1565.42 1168.77 1210.43 1514.7 2264.61 1472.06 1475.5 1477.76 1117.47 916.6553332_MZ 3-O-Sulfogalactosylceramide with formula C50H95NO11S Un 1.0 None None None None 3-O-Sulfogalactosylceramide is an acidic, sulfated glycosphingolipid, often known as sulfatide. This lipid occurs in membranes of various cell types, but is found in particularly high concentrations in myelin where it constitutes 3-4% of total membrane lipids. This lipid is synthesized primarily in the oligodendrocytes in the central nervous system. Accumulation of this lipid in the lysosomes is a characteristic of metachromatic leukodystrophy, a lysosomal storage disease caused by the deficiency of arylsulfatase A. Alterations in sulfatide metabolism, trafficking, and homeostasis are present in the earliest clinically recognizable stages of Alzheimer's disease.Cerebrosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Cerebrosides have a single sugar group linked to ceramide. The most common are galactocerebrosides (containing galactose), the least common are glucocerebrosides (containing glucose). Galactocerebrosides are found predominantly in neuronal cell membranes. In contrast glucocerebrosides are not normally found in membranes. Instead, they are typically intermediates in the synthesis or degradation of more complex glycosphingolipids. Galactocerebrosides are synthesized from ceramide and UDP-galactose. Excess lysosomal accumulation of glucocerebrosides is found in Gaucher disease. Sulfatides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Sulfatides are the sulfuric acid esters of galactocerebrosides. They are synthesized from galactocerebrosides and activated sulfate, 3'-phosphoadenosine 5'-phosphosulfate (PAPS). C50H95NO11S None None None 2744.37 2214.54 2347.48 2488.32 2475.17 2210.05 2592.91 2791.11 2368.65 2102.84 2987.79 3039.87 2461.34 2864.89 1960.94 2650.0 2541.24 2416.59 1719.82 2572.75 2831.05 2276.87 2671.55 2251.21 2954.15 2589.82 1662.43 2737.38 2389.0 3039.15 2331.81 3946.54 2301.69 2257.76 1851.26 2093.19 2020.88 2627.36 1909.07 2269.55 2225.69 1642.98 925.5384254_MZ Phosphatidylglycerolphosphate (18:0/22:4(7Z_10Z_13Z_16Z)) Un 1.0 None None None None C46H84O13P2 None None None 16367.2 14912.0 16367.7 17568.7 20173.6 16768.6 20166.1 17653.7 17539.6 14536.3 19352.5 19185.0 21100.5 17318.9 13380.3 16154.3 18677.2 19008.0 13357.9 18441.0 15009.2 14775.4 19730.5 14767.1 17922.1 20109.3 15162.6 17910.4 16370.4 15484.1 18168.5 16633.7 18461.9 16085.9 12983.4 16715.5 15094.6 16525.2 12173.3 15796.4 18475.8 15235.6 929.5074432_MZ Angiotensin III Un 1.0 None None None None C46H66N12O9 None None None 14914.4 13335.6 17340.3 14509.1 21534.4 15547.9 17781.5 11606.8 16134.9 12400.7 18458.7 18130.8 13095.4 15715.2 12838.7 11905.3 14329.9 11098.8 11804.4 14520.3 17766.4 14162.0 17998.7 12924.2 16040.0 17385.7 15337.8 14320.7 14090.4 15836.6 15859.7 12531.0 16289.2 11459.3 12356.6 13168.5 11857.8 18393.9 11104.7 15564.7 12224.4 13581.0 930.9836959_MZ Guanosine pentaphosphate adenosine Un 1.0 None None None None Guanosine pentaphosphate adenosine is a dinucleoside polyphosphate. Dinucleoside polyphosphates are an interesting group of signalling molecules that control numerous physiological functions. Diadenosine compounds, with a backbone of anything from two to seven phosphates, are known to occur naturally. Some of them have been isolated from cerebral nerve terminals and, acting via nucleoside (P1), nucleotide (P2), or dinucleotide receptors, can affect central nervous system function. Many of them have been isolated from human blood platelet secretory granules and are potentially involved in haemostatic mechanisms and peripheral control of vascular tone. Many visceral organs respond to the application of adenine dinucleotides and, although they act on receptors in the periphery that can be mainly defined as either P1 or P2, evidence is now accumulating for discrete dinucleotide receptors. In the periphery, adenine dinucleotides can be potent agonists, with diverse functions, causing contraction or relaxation of smooth muscle. Many P2X receptor proteins and P2Y receptors have been cloned and adenine dinucleotides have a variable pharmacological profile at these receptors and may be useful tools for characterising subtypes of P2X and P2Y receptors. Many extracellular roles of diadenosine polyphosphates are emerging as yet increasingly important, natural ligands for a plethora of structurally diverse mononucleotide and dinucleotide receptors. (PMID: 12772275, 7767329). C20H29N10O23P5 None None None 6299.56 6333.93 6466.36 5849.23 6493.41 6573.89 6926.25 6338.81 6141.95 5662.04 5767.55 6111.56 7054.58 5765.99 6958.9 6770.81 5793.52 5809.24 5891.35 6261.06 6328.58 5903.74 6133.75 6229.8 5736.99 6018.78 6294.33 5750.31 5903.2 6141.82 6880.13 6029.71 5787.35 5284.02 6979.86 5988.01 5491.4 6547.02 4549.49 5889.98 6067.21 5878.6 932.7545361_MZ Phosphatidylethanolamine (24:0/24:1(15Z)) Un 1.0 None None None None PE(24:0/24:1(15Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(24:0/24:1(15Z)), in particular, consists of one chain of lignoceric acid at the C-1 position and one chain of nervonic acid at the C-2 position. The lignoceric acid moiety is derived from groundnut oil, while the nervonic acid moiety is derived from fish oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. C53H104NO8P None None None 545.397 1014.69 365.18 1887.51 1304.46 732.951 1110.69 650.579 687.371 613.94 772.163 715.905 314.323 669.768 1062.88 1127.92 1171.21 245.434 452.812 364.217 502.696 290.806 650.253 664.628 731.866 558.517 822.041 703.087 204.187 621.978 828.878 1802.06 578.145 720.636 399.36 418.416 334.905 886.428 472.338 710.469 407.064 343.726 934.6779834_MZ Phosphatidylcholine (22:6(4Z_7Z_10Z_13Z_16Z_19Z)/24:1(15Z)) Un 1.0 None None None None PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z)), in particular, consists of one chain of docosahexaenoic acid at the C-1 position and one chain of nervonic acid at the C-2 position. The docosahexaenoic acid moiety is derived from fish oils, while the nervonic acid moiety is derived from fish oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C54H94NO8P None None None 2627.96 1627.4 2093.51 1990.49 2791.5 1705.17 2379.75 2038.23 2190.89 1747.26 2460.62 2114.28 3372.77 3736.58 1752.35 2421.41 2752.89 1711.21 1542.22 2243.74 2134.27 1900.47 2408.29 1960.9 2032.74 2038.92 1447.11 2195.65 1515.19 1986.26 1916.87 3744.86 2108.02 1445.8 1613.87 1695.79 1883.3 2671.36 1193.21 2073.7 2893.82 1673.27 935.3722045_MZ Oxytocin 1-8 Un 1.0 None None None None Oxytocin 1-8 is the fraction of Oxytocin which contains only Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu amino acid peptide. Oxytocin (sold as Pitocin, Syntocinon) is a mammalian hormone that acts primarily as a neurotransmitter in the brain. Also known as alpha-hypophamine (α-hypophamine), oxytocin has the distinction of being the very first polypeptide hormone to be sequenced and synthesized biochemically by Vincent du Vigneaud et al. in 1953. Oxytocin is best known for its roles in female reproduction: 1) it is released in large amounts after distension of the cervix and vagina during labor, and 2) after stimulation of the nipples, facilitating birth and breastfeeding, respectively. Recent studies have begun to investigate oxytocin's role in various behaviors, including orgasm, social recognition, pair bonding, anxiety, trust, love, and maternal behaviors. C40H60N10O12S2 None None None 414.261 942.912 542.56 647.315 903.689 693.93 719.464 548.069 705.632 572.833 879.565 629.685 630.286 648.697 606.653 946.818 258.481 469.781 432.471 611.232 260.355 395.448 626.182 433.75 662.02 653.396 713.886 779.099 586.385 630.73 704.276 962.365 531.636 458.405 570.508 395.071 293.2 594.485 368.599 637.821 1018.09 345.461 935.7534174_MZ Triglyceride with formula C63H100O5 Un 1.0 None None None None TG(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))[iso6] is a monodocosahexaenoic acid triglyceride. Triglycerides (TGs) are also known as triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.e. fatty acid tri-esters of glycerol). TGs may be divided into three general types with respect to their acyl substituents. They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. TG(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))[iso6], in particular, consists of one chain of arachidonic acid at the C-1 position, one chain of linoleic acid at the C-2 position and one chain of docosahexaenoic acid at the C-3 position. TGs are the main constituent of vegetable oil and animal fats. TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) with the help of lipases and bile secretions, which can then move into blood vessels. The triglycerides are rebuilt in the blood from their fragments and become constituents of lipoproteins, which deliver the fatty acids to and from fat cells among other functions. Various tissues can release the free fatty acids and take them up as a source of energy. Fat cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain cannot utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when it is broken down. (www.cyberlipid.org, www.wikipedia.org)TAGs can serve as fatty acid stores in all cells, but primarily in adipocytes of adipose tissue. The major building block for the synthesis of triacylglycerides, in non-adipose tissue, is glycerol. Adipocytes lack glycerol kinase and so must use another route to TAG synthesis. Specifically, dihydroxyacetone phosphate (DHAP), which is produced during glycolysis, is the precursor for TAG synthesis in adipose tissue. DHAP can also serve as a TAG precursor in non-adipose tissues, but does so to a much lesser extent than glycerol. The use of DHAP for the TAG backbone depends on whether the synthesis of the TAGs occurs in the mitochondria and ER or the ER and the peroxisomes. The ER/mitochondria pathway requires the action of glycerol-3-phosphate dehydrogenase to convert DHAP to glycerol-3-phosphate. Glycerol-3-phosphate acyltransferase then esterifies a fatty acid to glycerol-3-phosphate thereby generating lysophosphatidic acid. The ER/peroxisome reaction pathway uses the peroxisomal enzyme DHAP acyltransferase to acylate DHAP to acyl-DHAP which is then reduced by acyl-DHAP reductase. The fatty acids that are incorporated into TAGs are activated to acyl-CoAs through the action of acyl-CoA synthetases. Two molecules of acyl-CoA are esterified to glycerol-3-phosphate to yield 1,2-diacylglycerol phosphate (also known as phosphatidic acid). The phosphate is then removed by phosphatidic acid phosphatase (PAP1), to generate 1,2-diacylglycerol. This diacylglycerol serves as the substrate for addition of the third fatty acid to make TAG. Intestinal monoacylglycerols, derived from dietary fats, can also serve as substrates for the synthesis of 1,2-diacylglycerols. C63H100O5 None None None 583.265 703.164 399.437 1197.77 1237.44 812.723 824.596 733.806 573.145 666.642 572.467 458.508 267.294 902.499 986.211 1258.35 682.904 362.667 553.115 476.835 424.68 254.625 630.953 594.348 681.488 457.391 560.106 507.608 134.277 666.81 719.557 1877.88 607.889 560.725 329.974 424.966 293.829 456.324 412.318 529.102 353.333 472.714 936.6827690_MZ Phosphatidylcholine (22:5(4Z_7Z_10Z_13Z_16Z)/24:1(15Z)) Un 1.0 None None None None PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z)), in particular, consists of one chain of docosapentaenoic acid at the C-1 position and one chain of nervonic acid at the C-2 position. The docosapentaenoic acid moiety is derived from animal fats and brain, while the nervonic acid moiety is derived from fish oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C54H96NO8P None None None 6332.54 5329.68 6976.25 7921.23 10285.6 4540.25 7614.33 6151.43 8621.21 5386.06 8656.22 6585.09 7122.06 11709.3 6419.97 4479.29 10359.1 5720.01 5853.86 5113.65 8770.45 6676.33 8132.84 5203.44 6960.25 7838.88 5994.04 7014.06 4541.95 5738.0 6438.94 5722.4 7773.56 4344.02 5212.89 6100.05 7361.62 7397.83 3254.73 6988.54 5704.47 6367.32 937.5349929_MZ Phosphatidylinositol phosphate (16:0/18:0) Un 1.0 None None None None C43H84O16P2 None None None 10098.0 11927.3 12518.7 13172.3 16654.9 11848.9 13632.8 11521.4 14041.2 11428.7 16837.9 16005.5 10084.2 12681.4 11682.3 10476.6 11296.0 8650.41 10625.9 11689.8 11188.7 11951.4 13479.6 10276.4 11686.6 14364.7 11300.8 13106.4 11134.5 11791.0 11692.3 10220.6 14613.9 9446.88 9063.81 10737.0 10966.5 13491.6 7377.33 12475.9 9907.51 10438.2 939.8443376_MZ Tricaprylic glyceride (18:1(9Z)/18:1(9Z)/22:1(13Z))[iso3] Un 1.0 None None None None TG(18:1(9Z)/18:1(9Z)/22:1(13Z))[iso3] is a dioleic acid triglyceride. Triglycerides (TGs) are also known as triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.e. fatty acid tri-esters of glycerol). TGs may be divided into three general types with respect to their acyl substituents. They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. TG(18:1(9Z)/18:1(9Z)/22:1(13Z))[iso3], in particular, consists of one chain of oleic acid at the C-1 position, one chain of oleic acid at the C-2 position and one chain of erucic acid at the C-3 position. TGs are the main constituent of vegetable oil and animal fats. TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) with the help of lipases and bile secretions, which can then move into blood vessels. The triglycerides are rebuilt in the blood from their fragments and become constituents of lipoproteins, which deliver the fatty acids to and from fat cells among other functions. Various tissues can release the free fatty acids and take them up as a source of energy. Fat cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain cannot utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when it is broken down. (www.cyberlipid.org, www.wikipedia.org)TAGs can serve as fatty acid stores in all cells, but primarily in adipocytes of adipose tissue. The major building block for the synthesis of triacylglycerides, in non-adipose tissue, is glycerol. Adipocytes lack glycerol kinase and so must use another route to TAG synthesis. Specifically, dihydroxyacetone phosphate (DHAP), which is produced during glycolysis, is the precursor for TAG synthesis in adipose tissue. DHAP can also serve as a TAG precursor in non-adipose tissues, but does so to a much lesser extent than glycerol. The use of DHAP for the TAG backbone depends on whether the synthesis of the TAGs occurs in the mitochondria and ER or the ER and the peroxisomes. The ER/mitochondria pathway requires the action of glycerol-3-phosphate dehydrogenase to convert DHAP to glycerol-3-phosphate. Glycerol-3-phosphate acyltransferase then esterifies a fatty acid to glycerol-3-phosphate thereby generating lysophosphatidic acid. The ER/peroxisome reaction pathway uses the peroxisomal enzyme DHAP acyltransferase to acylate DHAP to acyl-DHAP which is then reduced by acyl-DHAP reductase. The fatty acids that are incorporated into TAGs are activated to acyl-CoAs through the action of acyl-CoA synthetases. Two molecules of acyl-CoA are esterified to glycerol-3-phosphate to yield 1,2-diacylglycerol phosphate (also known as phosphatidic acid). The phosphate is then removed by phosphatidic acid phosphatase (PAP1), to generate 1,2-diacylglycerol. This diacylglycerol serves as the substrate for addition of the third fatty acid to make TAG. Intestinal monoacylglycerols, derived from dietary fats, can also serve as substrates for the synthesis of 1,2-diacylglycerols. C61H112O6 None None None 878.444 1156.69 948.909 1618.99 1100.83 1227.99 1094.3 1323.85 973.299 983.646 830.57 989.187 1039.16 884.078 1035.78 2522.25 853.829 1052.29 964.967 1022.18 960.166 922.052 1183.4 919.342 1025.63 1010.06 1036.87 1037.45 708.855 779.407 1638.23 2819.91 722.08 1071.52 1301.46 861.514 776.178 903.435 928.195 951.525 829.772 948.39 941.5377961_MZ Phosphatidylinositol phosphate (16:0/20:2(11Z_14Z)) Un 1.0 None None None None C45H84O16P2 None None None 12721.8 14436.1 14425.7 18231.2 18103.0 14277.8 15048.3 13118.2 14966.0 13138.2 18422.2 17915.5 12348.7 15619.8 12941.7 14638.7 13206.1 13126.4 11502.8 13224.5 13477.2 12937.2 16660.2 12264.2 14764.5 17477.7 13686.6 15138.9 14179.7 13405.7 15907.8 14340.0 15752.9 12233.7 12207.1 13414.6 12382.6 14073.2 9164.25 14227.5 11721.5 12633.8 941.8468199_MZ Tricaprylic glyceride (18:0/20:1(11Z)/20:1(11Z))[iso3] Un 1.0 None None None None C61H114O6 None None None 591.154 727.051 641.161 1098.45 654.686 681.362 625.019 720.469 652.21 657.039 577.835 605.524 635.922 423.142 898.603 1939.92 804.239 413.201 563.154 688.85 568.188 498.4 589.879 618.455 752.362 567.418 779.613 570.373 464.926 518.016 1169.98 2054.22 384.23 557.306 890.44 456.907 500.412 624.054 372.479 533.687 797.969 495.311 942.2144196_MZ (2E)-Dodecenoyl-CoA Un 1.0 None None None None (2E)-Dodecenoyl-CoA is an intermediate in fatty acid metabolism, the substrate of the enzyme acyl-CoA oxidase [EC-1.3.3.6], and enzymes acyl-CoA dehydrogenase, long-chain-acyl-CoA dehydrogenase [EC 1.3.99.3-1.3.99.13]; (2E)-Dodecenoyl-CoA is an intermediate in fatty acid elongation in mitochondria, being the substrate of the enzyme enoyl-CoA hydratase and [EC 4.2.1.17]. (KEGG). C33H52N7O17P3S None None None 713.207 514.41 802.9 411.759 461.995 629.682 596.451 305.432 505.536 340.609 326.581 552.13 565.106 570.224 397.428 381.794 396.57 519.712 510.144 574.001 827.187 468.222 451.174 645.15 522.178 330.821 345.557 484.439 669.865 716.778 623.329 434.5 802.596 315.403 733.479 707.007 635.738 414.441 361.895 261.794 737.233 474.924 943.2801998_MZ Disialyllactose Un 1.0 None None None None Disialyllactose is a naturally occurring oligosaccharide present in the cell surface and in breast milk. Disialyllactose has been identified as one of the binding sites of the C fragment of the clostridial tetanus toxin, binding with great specificity and high affinity. Clostridial neurotoxins, botulinum and tetanus, gain entry into motor neurons by binding to the sialic or N-acetylneuraminic acid (NeuAc) residues of gangliosides and specific protein receptors attached to the cell's surface. Neurotoxins interact with motor neurons, blocking acetylcholine release and causing muscle paralysis and death. The glycosidic linkage between Neu5Ac and other monosaccharides is susceptible to hydrolysis at low pH, and disialyl lactose is unstable under acidic conditions. (PMID: 16713287, 16104015, 7263800, 7972078). C34H56N2O27 None None None 82.0627 163.484 87.0536 41.1692 27.608 31.7774 72.3703 128.211 531.631 160.204 294.029 1390.09 25.4965 36.8047 76.0839 109.56 75.2361 159.29 103.511 191.725 54.9646 271.136 218.174 228.89 262.894 282.859 275.188 185.852 129.936 241.925 204.942 210.041 72.1961 168.696 229.161 281.95 944.7513128_MZ Phosphatidylcholine (22:1(13Z)/24:1(15Z)) Un 1.0 None None None None PC(22:1(13Z)/24:1(15Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(22:1(13Z)/24:1(15Z)), in particular, consists of one chain of erucic acid at the C-1 position and one chain of nervonic acid at the C-2 position. The erucic acid moiety is derived from seed oils and avocados, while the nervonic acid moiety is derived from fish oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C54H104NO8P None None None 358.859 619.25 204.177 724.139 415.011 523.747 562.777 465.085 403.025 370.243 434.775 236.55 156.506 537.334 366.305 1099.04 382.583 247.419 299.199 393.563 290.607 242.399 400.757 328.17 462.378 490.235 479.328 425.669 174.797 426.137 644.364 1561.61 165.453 371.613 365.472 249.68 218.987 247.631 306.86 316.957 172.84 196.528 955.5804257_MZ 1_2-Di-(9Z_12Z_15Z-octadecatrienoyl)-3-(Galactosyl-alpha-1-6-Galactosyl-beta-1)-glycerol Un 1.0 None None None None C51H84O15 None None None 16417.3 11784.0 15775.0 12058.9 21651.4 12535.9 17041.0 14074.6 17333.6 11525.5 16916.5 14409.1 23373.6 15782.9 13185.5 13578.9 15903.7 19204.7 12437.0 15352.7 14599.0 15037.1 16263.2 12681.9 17113.4 18588.4 11097.3 15909.2 17844.8 13674.9 15005.2 10688.5 17739.0 13186.4 12179.7 18979.1 13698.1 14776.4 9808.68 14682.2 18478.1 15229.6 956.2976014_MZ Pentaglutamyl folate Un 1.0 None None None None Pentaglutamyl folate is a naturally occurring form of folic acid. Naturally occurring folates exist in multiple forms, differing in pteridine ring structure and number of glutamate residues. (PMID: 10702529). Low methionine synthase activity for whatever reason (metabolic or dietary) may lead to an increase in the relative abundance of Pentaglutamyl folate. (PMID: 10329020). C39H47N11O18 None None None 274.929 220.983 94.599 314.821 78.1092 118.46 47.3408 196.464 49.635 161.33 133.702 1100.78 240.916 136.644 248.95 85.825 182.536 246.238 168.153 83.8369 152.072 54.6015 235.289 99.0239 267.892 334.878 50.8256 83.3289 153.706 148.893 210.632 162.492 303.407 4057.5 103.99 962.2584524_MZ 3-Oxododecanoyl-CoA Un 1.0 None None None None 3-Oxododecanoyl-CoA is a human metabolite involved in the fatty acid elongation in mitochondria pathway. The enzyme acetyl-CoA C-acyltransferase catalyzes the formation of this metabolite from Acetyl-CoA. C33H56N7O18P3S None None None 141.73 133.374 153.984 151.779 152.067 256.839 261.455 271.923 46.9604 143.443 200.374 223.884 58.5785 345.161 287.14 489.562 198.887 538.933 175.324 228.463 120.408 215.299 230.18 246.781 229.782 158.659 175.983 154.3 208.278 258.506 146.797 91.2445 200.473 126.091 199.429 264.019 238.453 96.1301 167.576 181.335 531.292 178.527 966.2889663_MZ 3Z-dodecenoyl-CoA Un 1.0 None None None None 3Z-dodecenoyl-CoA is an intermediate in fatty acid metabolism. 3Z-dodecenoyl-CoA is converted from trans-Dodec-2-enoyl-CoA via acyl-CoA oxidase, acyl-CoA dehydrogenase, and long-chain-acyl-CoA dehydrogenase [EC:1.3.3.6, 1.3.99.3, 1.3.99.13]. C33H56N7O17P3S None None None 149.271 166.622 103.889 79.8051 144.296 393.797 187.499 40.398 124.41 286.008 288.92 190.566 182.096 574.185 72.2683 148.019 165.328 257.623 149.502 100.169 150.519 107.317 216.09 114.344 200.702 77.8925 224.031 800.768 261.663 103.066 321.011 131.897 78.0931 144.918 53.4081 116.357 114.569 157.711 967.0005349_MZ Diguanosine pentaphosphate Un 1.0 None None None None Diguanosine pentaphosphate is a diguanosine polyphosphate. Diguanosine polyphosphates (GpnGs) are found in human platelets, among a number of dinucleoside polyphosphates, which vary with respect to the number of phosphate groups and the nucleoside moieties; not only diguanosine polyphosphates (GpnG) are found, but also mixed dinucleoside polyphosphates containing one adenosine and one guanosine moiety (ApnG). The vasoactive nucleotides that can be detected in human plasma contain short(n=2-3)and long(n=4-6)polyphosphate groups. GpnGs have not yet been characterized so far with respect to their effects on kidney vasculature. (PMID: 11159696, 11682456, 11115507). C20H29N10O24P5 None None None 4557.88 4425.91 4388.49 3555.92 4931.63 4835.37 5219.44 4243.41 3833.62 3518.83 4052.75 4001.69 4181.79 3716.76 4473.23 5463.02 4754.24 3912.57 4297.3 4391.62 4777.88 3761.09 4360.51 4552.1 4038.81 4065.37 4580.83 4004.46 3734.2 4010.72 5587.32 4250.28 3696.38 3504.22 4654.21 4331.04 3435.58 3634.08 2467.16 3900.26 4577.79 4197.56 969.5401269_MZ Phosphatidylinositol phosphate (16:0/22:2(13Z_16Z)) Un 1.0 None None None None PIP(16:0/22:2(13Z,16Z)) is a phosphatidylinositol phosphate. Phosphatidylinositol phosphates are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to a phosphorylated inositol (hexahydroxycyclohexane). Phosphatidylinositol phosphates are generated from phosphatidylinositols, which are phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated. Phosphatidylinositols phosphates can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 18 and 20 carbons are the most common. PIP(16:0/22:2(13Z,16Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of docosadienoic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the docosadienoic acid moiety is derived from animal fats. The most important phosphatidylinositol phosphate in both quantitative and biological terms is phosphatidylinositol 4-phosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes. Phosphatidylinositols phosphates are usually present at low levels only in tissues, typically at about 1 to 3% of the concentration of phosphatidylinositol. C47H88O16P2 None None None 11495.6 13696.6 14977.5 16336.0 19958.3 14656.2 15047.6 12644.7 14226.0 14890.1 18643.6 16081.8 14649.8 15663.1 13734.0 13049.2 13376.4 13362.7 12083.8 13882.1 12159.7 13619.4 14859.4 12001.9 14562.4 16657.1 13622.4 15168.1 13135.4 13682.0 14750.3 14426.9 17075.3 11578.6 10846.7 12038.7 11931.5 14321.9 10253.1 14149.1 14232.8 11927.2 974.3461032_MZ 5-Methyltetrahydropteroylpentaglutamate Un 1.0 None None None None 5-Methyltetrahydropteroylpentaglutamate is a naturally occurring folate coenzyme; binds to an inhibits glyxine N-methyltransferase to regulate the availability of methyl groups in the liver (Journal of Biological Chemistry 264 (16): 9638-9642 JUN 5 1989 ). C40H53N11O18 None None None 272.891 284.804 332.143 441.973 415.754 305.92 255.649 388.158 308.78 281.545 416.911 464.437 227.983 293.545 362.691 561.008 408.119 365.003 305.016 309.638 244.276 374.617 165.873 144.533 381.485 448.033 346.151 195.297 256.985 177.058 518.088 901.889 406.518 353.578 275.055 321.879 196.318 363.64 375.764 313.385 319.611 197.222 976.5030119_MZ CDP-Diglyceride (16:0/18:2(9Z_12Z)) Un 1.0 None None None None CDP-DG(16:0/18:2(9Z,12Z)) is a cytidine diphosphate diacylglycerol or CDP-diacylglycerol. CDP-diacylglycerol (CDP-DG) is an important branchpoint intermediate in eukaryotic phospholipid biosynthesis and could be a key regulatory molecule in phospholipid metabolism. It is a glycerophospholipid in which a cytidine diphosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, CDP-diacylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. CDP-DG(16:0/18:2(9Z,12Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of linoleic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the linoleic acid moiety is derived from seed oils. CDP-diacylglycerols are intermediates in the synthesis of phosphatidylglycerols (PG, PC, PS, PI), which is catalyzed by CDP-diacyl synthase, synthase, phosphatidylglycerolphosphate (PGP) synthase, phosphatidylinositol (PI) synthase, and phosphatidylserine (PS) synthase. Cytidine diphosphate diacylglycerols are rarely noticed in analyses of lipid compositions of tissues, as they are present is such small amounts, perhaps only 0.05% or so of the total phospholipids. C46H81N3O15P2 None None None 7261.18 7461.83 8008.97 7576.03 9141.11 8116.66 8622.94 7539.71 8500.65 7590.62 9999.82 10203.9 5700.1 7728.53 7480.53 6998.47 6629.04 7037.12 6091.85 7769.95 7504.75 7025.35 8442.58 6774.9 7696.24 8395.02 7412.39 8344.33 7654.07 7989.46 7814.6 6603.42 8134.07 6332.98 6497.29 6825.33 6754.72 8453.31 5313.81 8213.89 5760.73 7054.89 976.8117013_MZ Phosphatidylcholine (24:0/24:0) Un 1.0 None None None None PC(24:0/24:0) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(24:0/24:0), in particular, consists of two chains of lignoceric acid at the C-1 and C-2 positions. The lignoceric acid moieties are derived from groundnut oil. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C56H112NO8P None None None 255.276 304.91 249.274 454.309 266.543 273.799 413.976 395.346 292.685 228.485 310.069 204.029 69.6567 199.066 325.957 1183.3 375.654 94.1139 171.723 299.656 421.54 155.725 289.547 290.758 308.415 353.747 331.182 279.023 187.292 226.479 719.672 1220.66 238.749 358.339 552.596 273.859 175.785 191.371 206.101 256.234 425.247 219.029 978.5180648_MZ CDP-Diglyceride (16:0/18:1(11Z)) Un 1.0 None None None None CDP-DG(16:0/18:1(11Z)) is a cytidine diphosphate diacylglycerol or CDP-diacylglycerol. CDP-diacylglycerol (CDP-DG) is an important branchpoint intermediate in eukaryotic phospholipid biosynthesis and could be a key regulatory molecule in phospholipid metabolism. It is a glycerophospholipid in which a cytidine diphosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, CDP-diacylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. CDP-DG(16:0/18:1(11Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of vaccenic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the vaccenic acid moiety is derived from butter fat and animal fat. CDP-diacylglycerols are intermediates in the synthesis of phosphatidylglycerols (PG, PC, PS, PI), which is catalyzed by CDP-diacyl synthase, synthase, phosphatidylglycerolphosphate (PGP) synthase, phosphatidylinositol (PI) synthase, and phosphatidylserine (PS) synthase. Cytidine diphosphate diacylglycerols are rarely noticed in analyses of lipid compositions of tissues, as they are present is such small amounts, perhaps only 0.05% or so of the total phospholipids. C46H83N3O15P2 None None None 5717.18 6402.56 6255.72 6642.22 8446.65 7110.3 6977.54 6466.32 7143.94 6335.14 8410.62 8401.79 5169.67 6707.86 6123.1 6614.22 5339.16 5530.09 5127.86 6202.82 6052.97 6494.92 7087.2 5464.37 6504.5 7798.04 6607.06 6916.49 6801.42 6544.48 6831.82 5974.06 7300.65 5294.08 5792.04 6183.15 5517.15 7498.5 4174.44 6474.04 5157.3 5769.23 987.4475567_MZ PIP2(16:0/16:1(9Z)) Un 1.0 None None None None PIP2(16:0/16:1(9Z)) is a phosphatidylinositol bisphosphate. Phosphatidylinositol bisphosphates are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to a bisphosphorylated inositol (hexahydroxycyclohexane). Phosphatidylinositol bisphosphates are generated from phosphatidylinositols which are phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated. Phosphatidylinositols bisphosphates can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 18 and 20 carbons are the most common. PIP2(16:0/16:1(9Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of palmitoleic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the palmitoleic acid moiety is derived from animal fats and vegetable oils. The most important phosphatidylinositol bisphosphate in both quantitative and biological terms is phosphatidylinositol 4,5-bisphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes. Phosphatidylinositols phosphates are usually present at low levels only in tissues, typically at about 1 to 3% of the concentration of phosphatidylinositol. C41H79O19P3 None None None 2255.58 2363.57 2273.31 3182.14 3128.57 2798.08 2874.32 2237.92 2496.03 2408.57 3068.21 2720.34 2475.12 2800.36 2293.31 2892.26 2642.98 2154.36 2202.07 2674.58 2637.66 2163.94 2919.13 2131.43 2539.88 2726.49 2663.4 2635.14 2238.43 2499.29 3169.22 3340.12 2490.11 2205.56 2022.24 2188.01 1991.46 2440.79 1836.78 2513.94 2065.86 2277.73 990.2815242_MZ 3-Oxotetradecanoyl-CoA Un 1.0 None None None None 3-Oxotetradecanoyl-CoA is a product of the peroxisomal beta oxidation of hexadenoic acid by the enzyme acyl-CoA oxidase which results in long-chain 3-oxoacyl-CoA-esters. (PMID: 7548202). Myristoyl-CoA:protein N-myristoyltransferase (E.C. 2.3.1.97) is a eukaryotic enzyme that catalyzes the transfer of myristate (C14:O) from myristoyl-CoA to the amino nitrogen of glycine. This covalent protein modification occurs cotranslationally, is apparently irreversible, and affects proteins with diverse functions. (PMID: 2818568). C35H60N7O18P3S None None None 207.4 260.289 254.105 359.453 381.158 413.792 523.113 262.168 427.529 221.858 324.76 269.211 269.96 404.544 447.797 131.248 74.9135 79.435 274.502 209.389 135.596 195.245 291.245 186.761 385.689 351.336 651.579 379.095 366.472 437.456 400.262 344.191 328.112 289.435 325.077 243.414 392.835 183.407 322.706 291.794 344.6 278.818 991.9075997_MZ Triglyceride (20:0/20:0/20:1(11Z))[iso3] Un 1.0 None None None None TG(20:0/20:0/20:1(11Z))[iso3] is a diarachidic acid triglyceride. Triglycerides (TGs) are also known as triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.e. fatty acid tri-esters of glycerol). TGs may be divided into three general types with respect to their acyl substituents. They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. TG(20:0/20:0/20:1(11Z))[iso3], in particular, consists of one chain of arachidic acid at the C-1 position, one chain of arachidic acid at the C-2 position and one chain of eicosenoic acid at the C-3 position. TGs are the main constituent of vegetable oil and animal fats. TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) with the help of lipases and bile secretions, which can then move into blood vessels. The triglycerides are rebuilt in the blood from their fragments and become constituents of lipoproteins, which deliver the fatty acids to and from fat cells among other functions. Various tissues can release the free fatty acids and take them up as a source of energy. Fat cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain cannot utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when it is broken down. (www.cyberlipid.org, www.wikipedia.org)TAGs can serve as fatty acid stores in all cells, but primarily in adipocytes of adipose tissue. The major building block for the synthesis of triacylglycerides, in non-adipose tissue, is glycerol. Adipocytes lack glycerol kinase and so must use another route to TAG synthesis. Specifically, dihydroxyacetone phosphate (DHAP), which is produced during glycolysis, is the precursor for TAG synthesis in adipose tissue. DHAP can also serve as a TAG precursor in non-adipose tissues, but does so to a much lesser extent than glycerol. The use of DHAP for the TAG backbone depends on whether the synthesis of the TAGs occurs in the mitochondria and ER or the ER and the peroxisomes. The ER/mitochondria pathway requires the action of glycerol-3-phosphate dehydrogenase to convert DHAP to glycerol-3-phosphate. Glycerol-3-phosphate acyltransferase then esterifies a fatty acid to glycerol-3-phosphate thereby generating lysophosphatidic acid. The ER/peroxisome reaction pathway uses the peroxisomal enzyme DHAP acyltransferase to acylate DHAP to acyl-DHAP which is then reduced by acyl-DHAP reductase. The fatty acids that are incorporated into TAGs are activated to acyl-CoAs through the action of acyl-CoA synthetases. Two molecules of acyl-CoA are esterified to glycerol-3-phosphate to yield 1,2-diacylglycerol phosphate (also known as phosphatidic acid). The phosphate is then removed by phosphatidic acid phosphatase (PAP1), to generate 1,2-diacylglycerol. This diacylglycerol serves as the substrate for addition of the third fatty acid to make TAG. Intestinal monoacylglycerols, derived from dietary fats, can also serve as substrates for the synthesis of 1,2-diacylglycerols. C63H120O6 None None None 1675.99 1628.56 1690.02 1653.7 2008.13 1987.2 1955.54 2160.05 1457.66 1385.4 1660.95 1631.59 2172.98 4772.27 2103.75 2897.21 2136.65 1463.12 1413.97 1766.8 1844.66 1582.35 2023.28 1717.63 1417.62 1776.49 2019.46 1507.11 1310.94 1352.41 2467.32 2628.63 1219.09 1353.35 2083.93 1515.03 1299.04 1818.62 1055.68 1794.5 1774.63 1624.44 992.2821982_MZ 5-cis-8-cis-Tetradecadienoyl-CoA Un 1.0 None None None None 5-cis-8-cis-Tetradecadienoyl-CoA is an acyl-Coenzyme A that accumulates during the peroxisomal β-oxidation of arachidonic acid and 6,9,12-octadecatrienoic acid via the arachidonate pathway requiring both NADPH-dependent 2,4-dienoyl-CoA reductase and delta 3,5, delta 2,4-dienoyl-CoA isomerase.(PMID 9448727). C35H58N7O17P3S, (2S,6R,10R)-Trimethyl-hendecanoyl-CoA None None None 255.796 145.767 305.394 100.081 218.604 431.941 288.852 361.214 636.348 207.588 136.008 230.01 484.081 2469.23 378.381 246.31 161.132 159.932 376.55 388.558 341.643 231.22 199.055 366.915 104.714 252.718 286.034 287.95 319.862 347.591 519.769 566.262 456.116 59.6501 126.142 231.085 466.77 429.595 542.024 520.932 476.201 344.076 994.9830245_MZ Diadenosine hexaphosphate Un 1.0 None None None None Diadenosine hexaphosphate (AP6A) is a diadenosine polyphosphate. Diadenosine polyphosphates (APnAs, n = 3-6) are a family of endogenous vasoactive purine dinucleotides which have been isolated from thrombocytes. APnAs have been demonstrated to be involved in the control of vascular tone as well as the growth of vascular smooth muscle cells and hence, possibly, in atherogenesis. APnAs isolated substances are AP3A, AP4A, AP5A, and AP6A. APnAs are naturally occurring substances that facilitate tear secretion; they are released from the corneal epithelium, they stimulate tear production and therefore they may be considered as physiological modulators of tear secretion. The APnAs were discovered in the mid-sixties in the course of studies on aminoacyl-tRNA synthetases (aaRS). APnAs have emerged as intracellular and extracellular signalling molecules implicated in the maintenance and regulation of vital cellular functions and become considered as second messengers. Great variety of physiological and pathological effects in mammalian cells was found to be associated with alterations of APnAs. APnAs are polyphosphated nucleotidic substances which are found in the CNS and are known to be released in a calcium-dependent manner from storage vesicles in brain synaptosomes. AP6A is an avid inhibitor of eosinophil-derived neurotoxin (EDN). EDN is a catalytically proficient member of the pancreatic ribonuclease superfamily secreted along with other eosinophil granule proteins during innate host defense responses and various eosinophil-related inflammatory and allergic diseases. The ribonucleolytic activity of EDN is central to its antiviral and neurotoxic activities and possibly to other facets of its biological activity. AP6A have been demonstrated to be involved in the control of vascular tone as well as the growth of vascular smooth muscle cells and hence, possibly, in atherogenesis. AP6A have been identified in human platelets and shown to be an important modulator of cardiovascular function. (PMID: 11212966, 12738682, 11810214, 9607303, 8922753, 16401072, 12738682, 10094777). C20H30N10O25P6 None None None 12703.5 11880.0 12044.6 12171.5 12495.8 13095.6 14074.0 12469.8 11805.4 12484.4 12077.4 12807.2 11882.5 11729.2 12832.7 13992.4 13041.3 11878.6 12175.6 12151.7 12413.5 11035.6 12539.4 12623.0 12174.2 12372.6 11590.8 11624.2 11779.3 12282.7 12930.1 11823.8 12102.1 11794.5 11943.6 12330.1 11208.3 11954.9 10512.1 12296.9 13260.0 11784.3 995.3627300_MZ Crocin Un 1.0 None None None None Crocin is a water-soluble carotenoid pigment of saffron (Crocus sativus L.) that has been used as a spice for flavoring and coloring food preparations, and in Chinese traditional medicine as an anodyne or tranquilizer. Saffron is now used worldwide in folk medicine and is reputed to be useful in treating various human disorders such as heart and blood disorders. Stroke and heart attack are involved in reputed folkloric uses of saffron. Saffron is orally administrated as a decoction. Saffron extract exerts a protective effect on renal ischemia reperfusion induced oxidative damage in rats. Crocin suppresses tumor necrosis factor (TNF)alpha-induced apoptosis of pheochromocytoma (PC12) cells by modulating mRNA expressions of Bcl-2 family proteins, which trigger downstream signals culminating in caspase-3 activation followed by cell death. Depriving cultured PC12 cells of serum/glucose causes a rapid increase in cellular ceramide levels, followed by an increase in the risk of cell death. The accumulation of ceramide was found to depend on the activation of neutral sphingomyelinase (nSMase). Crocin prevented the activation of nSMase by enhancing the transcription of gamma-glutamylcysteinyl synthase, which contributes to a stable glutathione supply that blocks the activity of nSMase. (PMID: 17215084). Crocetin esters present in saffron stigmas and in Gardenia jasminoides Ellis fruit are the compounds responsible for their color. (PMID: 16448211). C44H64O24 None None None 239.006 554.844 497.224 404.532 530.185 440.74 269.267 367.882 459.078 435.894 448.518 782.184 270.768 302.266 619.004 547.128 228.18 203.22 243.733 331.774 215.324 407.3 390.109 401.55 647.1 720.093 378.05 531.182 357.542 409.214 278.251 771.135 397.487 362.417 341.769 277.249 396.187 578.532 248.589 455.095 202.152 183.303 995.7415567_MZ Tricaprylic glyceride (22:5(7Z_10Z_13Z_16Z_19Z)/18:2(9Z_12Z)/22:6(4Z_7Z_10Z_13Z_16Z_19Z))[iso6] Un 1.0 None None None None TG(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))[iso6] is a monodocosapentaenoic acid triglyceride. Triglycerides (TGs) are also known as triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.e. fatty acid tri-esters of glycerol). TGs may be divided into three general types with respect to their acyl substituents. They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. TG(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))[iso6], in particular, consists of one chain of docosapentaenoic acid at the C-1 position, one chain of linoleic acid at the C-2 position and one chain of docosahexaenoic acid at the C-3 position. TGs are the main constituent of vegetable oil and animal fats. TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) with the help of lipases and bile secretions, which can then move into blood vessels. The triglycerides are rebuilt in the blood from their fragments and become constituents of lipoproteins, which deliver the fatty acids to and from fat cells among other functions. Various tissues can release the free fatty acids and take them up as a source of energy. Fat cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain cannot utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when it is broken down. (www.cyberlipid.org, www.wikipedia.org)TAGs can serve as fatty acid stores in all cells, but primarily in adipocytes of adipose tissue. The major building block for the synthesis of triacylglycerides, in non-adipose tissue, is glycerol. Adipocytes lack glycerol kinase and so must use another route to TAG synthesis. Specifically, dihydroxyacetone phosphate (DHAP), which is produced during glycolysis, is the precursor for TAG synthesis in adipose tissue. DHAP can also serve as a TAG precursor in non-adipose tissues, but does so to a much lesser extent than glycerol. The use of DHAP for the TAG backbone depends on whether the synthesis of the TAGs occurs in the mitochondria and ER or the ER and the peroxisomes. The ER/mitochondria pathway requires the action of glycerol-3-phosphate dehydrogenase to convert DHAP to glycerol-3-phosphate. Glycerol-3-phosphate acyltransferase then esterifies a fatty acid to glycerol-3-phosphate thereby generating lysophosphatidic acid. The ER/peroxisome reaction pathway uses the peroxisomal enzyme DHAP acyltransferase to acylate DHAP to acyl-DHAP which is then reduced by acyl-DHAP reductase. The fatty acids that are incorporated into TAGs are activated to acyl-CoAs through the action of acyl-CoA synthetases. Two molecules of acyl-CoA are esterified to glycerol-3-phosphate to yield 1,2-diacylglycerol phosphate (also known as phosphatidic acid). The phosphate is then removed by phosphatidic acid phosphatase (PAP1), to generate 1,2-diacylglycerol. This diacylglycerol serves as the substrate for addition of the third fatty acid to make TAG. Intestinal monoacylglycerols, derived from dietary fats, can also serve as substrates for the synthesis of 1,2-diacylglycerols. C65H100O6, None None None 397.664 374.842 209.5 871.06 437.881 487.277 385.449 439.758 251.113 363.865 489.879 354.774 95.1221 545.507 376.447 1042.79 594.01 394.971 276.456 308.016 294.627 188.114 438.128 264.209 408.473 257.821 475.193 457.62 165.961 448.295 849.081 1252.45 216.697 293.366 210.504 352.513 234.093 199.065 256.938 341.321 455.891 148.515