1.0 2016-10-03 17:14:41 UTC 2020-06-04 19:43:23 UTC BMDB0008142 BMDB08142 PC(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)) PC(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)), also known as pc(18:2(9z,12z)/18:4(6z,9z,12z,15z)) or pc(18:2(9z,12z)/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(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)) exists in all eukaryotes, ranging from yeast to humans. PC(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)) can be biosynthesized from CDP-choline and DG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)) and L-serine can be converted into choline and PS(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)) pathway. GPCho(18:2/18:4) Phosphatidylcholine(36:6) Phosphatidylcholine(18:2/18:4) PC(18:2/18:4) 1-Linoleoyl-2-stearidonoyl-sn-glycero-3-phosphocholine Lecithin PC(36:6) 1-(9Z,12Z-Octadecadienoyl)-2-(6Z,9Z,12Z,15Z-octadecatetraenoyl)-sn-glycero-3-phosphocholine GPCho(36:6) PC(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)) C44H76NO8P 778.0499 777.530854925 trimethyl(2-{[(2R)-2-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)azanium trimethyl(2-{[(2R)-2-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)azanium [H][C@@](COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)(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/C44H76NO8P/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/h9,11,14-17,20-23,27,29,42H,6-8,10,12-13,18-19,24-26,28,30-41H2,1-5H3/b11-9-,16-14-,17-15-,22-20-,23-21-,29-27-/t42-/m1/s1 AHAUBJRIXRHFSJ-LTUZQPMLSA-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 5.37 ALOGPS logs -7.40 ALOGPS logp 7.72 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac trimethyl(2-{[(2R)-2-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)azanium ChemAxon average_mass 778.0499 ChemAxon mono_mass 777.530854925 ChemAxon smiles [H][C@@](COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)(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 C44H76NO8P ChemAxon inchi InChI=1S/C44H76NO8P/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/h9,11,14-17,20-23,27,29,42H,6-8,10,12-13,18-19,24-26,28,30-41H2,1-5H3/b11-9-,16-14-,17-15-,22-20-,23-21-,29-27-/t42-/m1/s1 ChemAxon inchikey AHAUBJRIXRHFSJ-LTUZQPMLSA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 240.97 ChemAxon polarizability 90.69 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(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)) SMP0080637 Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)) SMP0082442 Specdb::MsMs 315577 Specdb::MsMs 315578 Specdb::MsMs 315579 Specdb::MsMs 361612 Specdb::MsMs 361613 Specdb::MsMs 361614 Specdb::MsMs 2574739 Specdb::MsMs 2574740 Specdb::MsMs 2574741 Specdb::MsMs 2682579 Specdb::MsMs 2682580 Specdb::MsMs 2682581 Specdb::MsMs 2782717 Specdb::MsMs 2782718 Specdb::MsMs 2782719 Specdb::MsMs 2831557 Specdb::MsMs 2831558 Specdb::MsMs 2831559 Specdb::MsMs 3022269 Specdb::MsMs 3022270 Specdb::MsMs 3022271 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 Blood 0.7 +/- 0.2 uM By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Liver 3 +/- 1 nmol/g of tissue By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Longissimus Thoracis Muscle 0.3 +/- 0.1 nmol/g of tissue By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Ruminal Fluid 0.017 +/- 0.007 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. Semimembranosus Muscle 0.3 +/- 0.1 nmol/g of tissue By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Testis 0.4 +/- 0.1 nmol/g of tissue By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 52922733 89576