1.0 2016-09-30 23:49:34 UTC 2020-06-04 20:43:57 UTC BMDB0008041 BMDB08041 PC(18:0/18:3(9Z,12Z,15Z)) PC(18:0/18:3(9Z,12Z,15Z)), also known as gpcho(18:0/18:3) or gpcho(36:3), belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage. Thus, PC(18:0/18:3(9Z,12Z,15Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:0/18:3(9Z,12Z,15Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:0/18:3(9Z,12Z,15Z)) exists in all eukaryotes, ranging from yeast to humans. PC(18:0/18:3(9Z,12Z,15Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:0/18:3(9Z,12Z,15Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:0/18:3(9Z,12Z,15Z)); which is catalyzed by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:0/18:3(9Z,12Z,15Z)) can be biosynthesized from CDP-choline and DG(18:0/18:3(9Z,12Z,15Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:0/18:3(9Z,12Z,15Z)) and L-serine can be converted into choline and PS(18:0/18:3(9Z,12Z,15Z)) through the action of the enzyme phosphatidylserine synthase. In cattle, PC(18:0/18:3(9Z,12Z,15Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:0/18:3(9Z,12Z,15Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:0/18:3(9Z,12Z,15Z)) pathway. 1-Octadecanoyl-2-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phosphocholine 1-Octadecanoyl-2-(9Z,12Z,15Z-octadecatrienoyl)-sn-glycero-3-phosphocholine GPCho(18:0/18:3) GPCho(18:0/18:3n3) GPCho(18:0/18:3omega3) GPCho(36:3) PC(18:0/18:3) PC(18:0/18:3n3) PC(18:0/18:3omega3) PC(36:3) Phosphatidylcholine(18:0/18:3) Phosphatidylcholine(18:0/18:3n3) Phosphatidylcholine(18:0/18:3omega3) Phosphatidylcholine(36:3) SLPC 1-stearoyl-2-a-linolenoyl-sn-glycero-3-phosphocholine Lecithin 1-octadecanoyl-2-(9Z,12Z,15Z-octadeatrienoyl)-sn-glycero-3-phosphocholine PC(18:0/18:3(9Z,12Z,15Z)) 1-Octadecanoyl-2-(9Z,12Z,15Z)-octadecatrienoyl-sn-glycero-3-phosphocholine C44H82NO8P 784.0975 783.577805117 trimethyl(2-{[(2R)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-3-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)azanium lecithin CCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC InChI=1S/C44H82NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h9,11,15,17,21,23,42H,6-8,10,12-14,16,18-20,22,24-41H2,1-5H3/b11-9-,17-15-,23-21-/t42-/m1/s1 WZCLAXMADUBPSG-RIXBAXMTSA-N belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage. Organic compounds Lipids and lipid-like molecules Glycerophospholipids Glycerophosphocholines Phosphatidylcholines Amines Carbonyl compounds Carboxylic acid esters Dialkyl phosphates Dicarboxylic acids and derivatives Fatty acid esters Hydrocarbon derivatives Organic oxides Organic salts Organopnictogen compounds Phosphocholines Tetraalkylammonium salts Aliphatic acyclic compound Alkyl phosphate Amine Carbonyl group Carboxylic acid derivative Carboxylic acid ester Diacylglycero-3-phosphocholine Dialkyl phosphate Dicarboxylic acid or derivatives Fatty acid ester Fatty acyl Hydrocarbon derivative Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organic salt Organonitrogen compound Organooxygen compound Organopnictogen compound Phosphocholine Phosphoric acid ester Quaternary ammonium salt Tetraalkylammonium salt Aliphatic acyclic compounds 1,2-diacyl-sn-glycero-3-phosphocholine Diacylglycerophosphocholines Solid logp 5.77 ALOGPS logs -7.51 ALOGPS logp 8.81 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac trimethyl(2-{[(2R)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-3-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)azanium ChemAxon average_mass 784.0975 ChemAxon mono_mass 783.577805117 ChemAxon smiles CCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC ChemAxon formula C44H82NO8P ChemAxon inchi InChI=1S/C44H82NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h9,11,15,17,21,23,42H,6-8,10,12-14,16,18-20,22,24-41H2,1-5H3/b11-9-,17-15-,23-21-/t42-/m1/s1 ChemAxon inchikey WZCLAXMADUBPSG-RIXBAXMTSA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 237.62 ChemAxon polarizability 94.91 ChemAxon rotatable_bond_count 41 ChemAxon acceptor_count 4 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Phosphatidylcholine Biosynthesis PC(18:0/18:3(9Z,12Z,15Z)) SMP0080570 Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(9Z,12Z,15Z)) SMP0082373 Specdb::MsMs 302374 Specdb::MsMs 302375 Specdb::MsMs 302376 Specdb::MsMs 345085 Specdb::MsMs 345086 Specdb::MsMs 345087 Specdb::MsMs 2395656 Specdb::MsMs 2395657 Specdb::MsMs 2395658 Specdb::MsMs 2433841 Specdb::MsMs 2433842 Specdb::MsMs 2433843 Specdb::MsMs 2474927 Specdb::MsMs 2474928 Specdb::MsMs 2474929 Specdb::MsMs 2505236 Specdb::MsMs 2505237 Specdb::MsMs 2505238 Specdb::MsMs 2896221 Specdb::MsMs 2896222 Specdb::MsMs 2896223 All Tissues Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Milk 3.24 +/- 0.04 uM Commercial 1% milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 4.0 +/- 0.1 uM Commercial 2% milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 5.3 +/- 0.1 uM Commercial 3.25% milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Ruminal Fluid 0.029 uM By direct flow injection MS/MS. Daily cows fed barley grains (15% of diet dry matter) (n=8) Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7. 22959937 Ruminal Fluid 0.033 uM By direct flow injection MS/MS. Daily cows fed barley grains (30% of diet dry matter) (n=8) Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7. 22959937 Ruminal Fluid 0.02 +/- 0.06 uM Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Ruminal Fluid 0.04 +/- 0.09 uM Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Ruminal Fluid 0.04 +/- 0.09 uM Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Ruminal Fluid 0.211 +/- 0.19 uM Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Ruminal Fluid 0.021 uM By direct flow injection MS/MS. Daily cows fed barley grains (45% of diet dry matter) (n=8) Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7. 22959937 Ruminal Fluid 0.214 uM By direct flow injection MS/MS. No barley grains in diet (n=8) Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7. 22959937 24766706 52922657 78022 CPD-8281 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) BMDBP02841 Phosphatidylserine synthase 1 Q2KHY9 PTDSS1 Enzyme