1.0 2016-09-30 23:50:18 UTC 2020-06-04 20:44:43 UTC BMDB0008071 BMDB08071 PC(18:1(11Z)/18:1(9Z)) PC(18:1(11Z)/18:1(9Z)), also known as pc(18:1(11z)/18:1(9z)) or pc(18:1(11z)/18:1(9z)), 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(18:1(11Z)/18:1(9Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:1(11Z)/18:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:1(11Z)/18:1(9Z)) exists in all eukaryotes, ranging from yeast to humans. PC(18:1(11Z)/18:1(9Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:1(11Z)/18:1(9Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:1(11Z)/18:1(9Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:1(11Z)/18:1(9Z)) can be biosynthesized from CDP-choline and DG(18:1(11Z)/18:1(9Z)/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:1(11Z)/18:1(9Z)) and L-serine can be converted into choline and PS(18:1(11Z)/18:1(9Z)) through the action of the enzyme phosphatidylserine synthase. In cattle, PC(18:1(11Z)/18:1(9Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:1(11Z)/18:1(9Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:1(11Z)/18:1(9Z)) pathway. 1-Vaccenoyl-2-oleoyl-sn-glycero-3-phosphocholine Gpcho(18:1/18:1) Gpcho(18:1n7/18:1n9) Gpcho(18:1W7/18:1W9) Gpcho(36:2) Lecithin PC Aa C36:2 PC(18:1/18:1) PC(18:1n7/18:1n9) PC(18:1W7/18:1W9) PC(36:2) Phosphatidylcholine(18:1/18:1) Phosphatidylcholine(18:1n7/18:1n9) Phosphatidylcholine(18:1W7/18:1W9) Phosphatidylcholine(36:2) 1-(11Z-Octadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine PC(18:1(11Z)/18:1(9Z)) C44H84NO8P 786.1134 785.593455181 trimethyl(2-{[(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)azanium lecithin CCCCCCCC\C=C/CCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)COP([O-])(=O)OCC[N+](C)(C)C InChI=1S/C44H84NO8P/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/h16,18,21,23,42H,6-15,17,19-20,22,24-41H2,1-5H3/b18-16-,23-21-/t42-/m1/s1 FOECFSINPHCSNE-IYXNDCFRSA-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 Diacylglycerophosphocholines Solid logp 5.77 ALOGPS logs -7.58 ALOGPS logp 9.17 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac trimethyl(2-{[(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)azanium ChemAxon average_mass 786.1134 ChemAxon mono_mass 785.593455181 ChemAxon smiles CCCCCCCC\C=C/CCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)COP([O-])(=O)OCC[N+](C)(C)C ChemAxon formula C44H84NO8P ChemAxon inchi InChI=1S/C44H84NO8P/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/h16,18,21,23,42H,6-15,17,19-20,22,24-41H2,1-5H3/b18-16-,23-21-/t42-/m1/s1 ChemAxon inchikey FOECFSINPHCSNE-IYXNDCFRSA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 236.5 ChemAxon polarizability 96.57 ChemAxon rotatable_bond_count 42 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(18:1(11Z)/18:1(9Z)) SMP0080590 Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:1(9Z)) SMP0082393 Specdb::MsMs 183848 Specdb::MsMs 352270 Specdb::MsMs 352271 Specdb::MsMs 352272 Specdb::MsMs 2270167 Specdb::MsMs 2270168 Specdb::MsMs 2270169 Specdb::MsMs 2439337 Specdb::MsMs 2439338 Specdb::MsMs 2439339 Specdb::MsMs 2522562 Specdb::MsMs 2522563 Specdb::MsMs 2522564 Specdb::MsMs 2968128 Specdb::MsMs 2968129 Specdb::MsMs 2968130 Specdb::MsMs 3020181 Specdb::MsMs 3020182 Specdb::MsMs 3020183 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 Ruminal Fluid 0.263 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 0.104 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 0.019 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 0.642 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 Ruminal Fluid 0.564 +/- 0.381 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 0.501 +/- 0.341 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 0.531 +/- 0.436 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 0.601 +/- 0.735 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. 53478721 24766735 89688 FDB025262 C00157