1.0 2016-09-30 23:49:00 UTC 2020-06-04 19:46:14 UTC BMDB0008013 BMDB08013 PC(16:1(9Z)/20:3(5Z,8Z,11Z)) PC(16:1(9Z)/20:3(5Z,8Z,11Z)), also known as pc(16:1(9z)/20:3(5z,8z,11z)) or pc(16:1(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(16:1(9Z)/20:3(5Z,8Z,11Z)) is considered to be a glycerophosphocholine lipid molecule. PC(16:1(9Z)/20:3(5Z,8Z,11Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:1(9Z)/20:3(5Z,8Z,11Z)) exists in all eukaryotes, ranging from yeast to humans. PC(16:1(9Z)/20:3(5Z,8Z,11Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(16:1(9Z)/20:3(5Z,8Z,11Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(16:1(9Z)/20:3(5Z,8Z,11Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(16:1(9Z)/20:3(5Z,8Z,11Z)) can be biosynthesized from CDP-choline and DG(16:1(9Z)/20:3(5Z,8Z,11Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PC(16:1(9Z)/20:3(5Z,8Z,11Z)) and L-serine can be converted into choline and PS(16:1(9Z)/20:3(5Z,8Z,11Z)) through the action of the enzyme phosphatidylserine synthase. In cattle, PC(16:1(9Z)/20:3(5Z,8Z,11Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(16:1(9Z)/20:3(5Z,8Z,11Z)) pathway and phosphatidylethanolamine biosynthesis pe(16:1(9Z)/20:3(5Z,8Z,11Z)) pathway. GPCho(36:4) Phosphatidylcholine(16:1/20:3) Phosphatidylcholine(36:4) 1-Palmitoleoyl-2-meadoyl-sn-glycero-3-phosphocholine Lecithin PC(36:4) GPCho(16:1/20:3) PC(16:1/20:3) 1-(9Z-Hexadecenoyl)-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycero-3-phosphocholine PC(16:1(9Z)/20:3(5Z,8Z,11Z)) C44H80NO8P 782.0817 781.562155053 (2-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]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/CCCCCC)COP([O-])(=O)OCC[N+](C)(C)C InChI=1S/C44H80NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-25-27-29-31-33-35-37-44(47)53-42(41-52-54(48,49)51-39-38-45(3,4)5)40-50-43(46)36-34-32-30-28-26-24-19-17-15-13-11-9-7-2/h17,19-21,23,25,29,31,42H,6-16,18,22,24,26-28,30,32-41H2,1-5H3/b19-17-,21-20-,25-23-,31-29-/t42-/m1/s1 SKHRULFMZYNDLW-IRKGUOCTSA-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 5.73 ALOGPS logs -7.43 ALOGPS logp 8.44 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac (2-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium ChemAxon average_mass 782.0817 ChemAxon mono_mass 781.562155053 ChemAxon smiles CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)COP([O-])(=O)OCC[N+](C)(C)C ChemAxon formula C44H80NO8P ChemAxon inchi InChI=1S/C44H80NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-25-27-29-31-33-35-37-44(47)53-42(41-52-54(48,49)51-39-38-45(3,4)5)40-50-43(46)36-34-32-30-28-26-24-19-17-15-13-11-9-7-2/h17,19-21,23,25,29,31,42H,6-16,18,22,24,26-28,30,32-41H2,1-5H3/b19-17-,21-20-,25-23-,31-29-/t42-/m1/s1 ChemAxon inchikey SKHRULFMZYNDLW-IRKGUOCTSA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 238.74 ChemAxon polarizability 94.18 ChemAxon rotatable_bond_count 40 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(16:1(9Z)/20:3(5Z,8Z,11Z)) SMP0080551 Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:3(5Z,8Z,11Z)) SMP0082354 Specdb::CMs 228977 Specdb::MsMs 302464 Specdb::MsMs 302465 Specdb::MsMs 302466 Specdb::MsMs 345205 Specdb::MsMs 345206 Specdb::MsMs 345207 Specdb::MsMs 2297755 Specdb::MsMs 2297756 Specdb::MsMs 2297757 Specdb::MsMs 2356014 Specdb::MsMs 2356015 Specdb::MsMs 2356016 Specdb::MsMs 2445523 Specdb::MsMs 2445524 Specdb::MsMs 2445525 Specdb::MsMs 2517222 Specdb::MsMs 2517223 Specdb::MsMs 2517224 Specdb::MsMs 3000805 Specdb::MsMs 3000806 Specdb::MsMs 3000807 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 0.164 +/- 0.192 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. 89735 53478679 FDB025204