1.0 2016-09-30 23:50:23 UTC 2020-06-04 19:27:18 UTC BMDB0008075 BMDB08075 PC(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)) PC(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)), also known as pc(18:1(11z)/18:4(6z,9z,12z,15z)) or pc(18:1(11z)/18:4(6z,9z,12z,15z)), 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)/18:4(6Z,9Z,12Z,15Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)) exists in all eukaryotes, ranging from yeast to humans. PC(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)); which is catalyzed by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)) can be biosynthesized from CDP-choline and DG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)) and L-serine can be converted into choline and PS(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)) through the action of the enzyme phosphatidylserine synthase. In cattle, PC(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)) pathway. GPCho(36:5) Phosphatidylcholine(36:5) Lecithin 1-Vaccenoyl-2-stearidonoyl-sn-glycero-3-phosphocholine PC(36:5) GPCho(18:1/18:4) PC(18:1/18:4) 1-(11Z-Octadecenoyl)-2-(6Z,9Z,12Z,15Z-octadecatetraenoyl)-sn-glycero-3-phosphocholine Phosphatidylcholine(18:1/18:4) PC(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)) C44H78NO8P 780.0658 779.546504989 trimethyl(2-{[(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]propyl phosphonato]oxy}ethyl)azanium lecithin CCCCCC\C=C/CCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C44H78NO8P/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/h9,11,15-18,21,23,27,29,42H,6-8,10,12-14,19-20,22,24-26,28,30-41H2,1-5H3/b11-9-,17-15-,18-16-,23-21-,29-27-/t42-/m1/s1 QAMLWHXIPWZMCT-WXVJBZSZSA-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 5.56 ALOGPS logs -7.43 ALOGPS logp 8.08 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac trimethyl(2-{[(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]propyl phosphonato]oxy}ethyl)azanium ChemAxon average_mass 780.0658 ChemAxon mono_mass 779.546504989 ChemAxon smiles CCCCCC\C=C/CCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC ChemAxon formula C44H78NO8P ChemAxon inchi InChI=1S/C44H78NO8P/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/h9,11,15-18,21,23,27,29,42H,6-8,10,12-14,19-20,22,24-26,28,30-41H2,1-5H3/b11-9-,17-15-,18-16-,23-21-,29-27-/t42-/m1/s1 ChemAxon inchikey QAMLWHXIPWZMCT-WXVJBZSZSA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 239.85 ChemAxon polarizability 93.52 ChemAxon rotatable_bond_count 39 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)/18:4(6Z,9Z,12Z,15Z)) SMP0080594 Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)) SMP0082397 Specdb::MsMs 307834 Specdb::MsMs 307835 Specdb::MsMs 307836 Specdb::MsMs 351880 Specdb::MsMs 351881 Specdb::MsMs 351882 Specdb::MsMs 2612932 Specdb::MsMs 2612933 Specdb::MsMs 2612934 Specdb::MsMs 2679223 Specdb::MsMs 2679224 Specdb::MsMs 2679225 Specdb::MsMs 2755150 Specdb::MsMs 2755151 Specdb::MsMs 2755152 Specdb::MsMs 2953881 Specdb::MsMs 2953882 Specdb::MsMs 2953883 Specdb::MsMs 3091628 Specdb::MsMs 3091629 Specdb::MsMs 3091630 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 0.018 +/- 0.019 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. 53478729 89694