1.0 2016-09-30 23:46:58 UTC 2020-06-04 19:20:09 UTC BMDB0007914 BMDB07914 PC(14:1(9Z)/20:3(5Z,8Z,11Z)) PC(14:1(9Z)/20:3(5Z,8Z,11Z)), also known as pc(14:1(9z)/20:3(5z,8z,11z)) or pc(14:1(9z)/20:3(5z,8z,11z)), 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(14:1(9Z)/20:3(5Z,8Z,11Z)) is considered to be a glycerophosphocholine lipid molecule. PC(14:1(9Z)/20:3(5Z,8Z,11Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(14:1(9Z)/20:3(5Z,8Z,11Z)) exists in all eukaryotes, ranging from yeast to humans. PC(14:1(9Z)/20:3(5Z,8Z,11Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(14:1(9Z)/20:3(5Z,8Z,11Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(14:1(9Z)/20:3(5Z,8Z,11Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(14:1(9Z)/20:3(5Z,8Z,11Z)) can be biosynthesized from CDP-choline and DG(14:1(9Z)/20:3(5Z,8Z,11Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(14:1(9Z)/20:3(5Z,8Z,11Z)) and L-serine can be converted into choline and PS(14:1(9Z)/20:3(5Z,8Z,11Z)) through the action of the enzyme phosphatidylserine synthase. In cattle, PC(14:1(9Z)/20:3(5Z,8Z,11Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(14:1(9Z)/20:3(5Z,8Z,11Z)) pathway and phosphatidylethanolamine biosynthesis pe(14:1(9Z)/20:3(5Z,8Z,11Z)) pathway. 1-Myristoleoyl-2-meadoyl-sn-glycero-3-phosphocholine Gpcho(14:1/20:3) Gpcho(14:1n5/20:3n9) Gpcho(14:1W5/20:3W9) Gpcho(34:4) Lecithin PC Aa C34:4 PC(14:1/20:3) PC(14:1n5/20:3n9) PC(14:1W5/20:3W9) PC(34:4) Phosphatidylcholine(14:1/20:3) Phosphatidylcholine(14:1n5/20:3n9) Phosphatidylcholine(14:1W5/20:3W9) Phosphatidylcholine(34:4) 1-(9Z-Tetradecenoyl)-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycero-3-phosphocholine PC(14:1(9Z)/20:3(5Z,8Z,11Z)) C42H76NO8P 754.0285 753.530854925 (2-{[(2R)-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]-3-[(9Z)-tetradec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium lecithin CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/CCCC)COP([O-])(=O)OCC[N+](C)(C)C InChI=1S/C42H76NO8P/c1-6-8-10-12-14-16-18-19-20-21-22-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-17-15-13-11-9-7-2/h13,15,19-20,22-23,27,29,40H,6-12,14,16-18,21,24-26,28,30-39H2,1-5H3/b15-13-,20-19-,23-22-,29-27-/t40-/m1/s1 PONMSDSBSOWGHR-DKHJBHHKSA-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 5.35 ALOGPS logs -7.40 ALOGPS logp 7.56 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac (2-{[(2R)-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]-3-[(9Z)-tetradec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium ChemAxon average_mass 754.0285 ChemAxon mono_mass 753.530854925 ChemAxon smiles CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/CCCC)COP([O-])(=O)OCC[N+](C)(C)C ChemAxon formula C42H76NO8P ChemAxon inchi InChI=1S/C42H76NO8P/c1-6-8-10-12-14-16-18-19-20-21-22-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-17-15-13-11-9-7-2/h13,15,19-20,22-23,27,29,40H,6-12,14,16-18,21,24-26,28,30-39H2,1-5H3/b15-13-,20-19-,23-22-,29-27-/t40-/m1/s1 ChemAxon inchikey PONMSDSBSOWGHR-DKHJBHHKSA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 229.53 ChemAxon polarizability 90.26 ChemAxon rotatable_bond_count 38 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(14:1(9Z)/20:3(5Z,8Z,11Z)) SMP0080473 Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:3(5Z,8Z,11Z)) SMP0082276 Specdb::MsMs 298027 Specdb::MsMs 298028 Specdb::MsMs 298029 Specdb::MsMs 339706 Specdb::MsMs 339707 Specdb::MsMs 339708 Specdb::MsMs 2341824 Specdb::MsMs 2341825 Specdb::MsMs 2341826 Specdb::MsMs 2504063 Specdb::MsMs 2504064 Specdb::MsMs 2504065 Specdb::MsMs 2593096 Specdb::MsMs 2593097 Specdb::MsMs 2593098 Specdb::MsMs 2788108 Specdb::MsMs 2788109 Specdb::MsMs 2788110 Specdb::MsMs 2826178 Specdb::MsMs 2826179 Specdb::MsMs 2826180 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 0.009 +/- 0.003 uM Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured DFI-MS/MS. 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. 24766590 53478625 88917 FDB025106 C00157 PHOSPHATIDYLCHOLINE