1.0 2016-10-03 17:15:20 UTC 2020-06-04 19:43:24 UTC BMDB0008172 BMDB08172 PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)), also known as pc(18:3(6z,9z,12z)/18:3(6z,9z,12z)) or pc(18:3(6z,9z,12z)/18:3(6z,9z,12z)), 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(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) exists in all eukaryotes, ranging from yeast to humans. PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)); which is catalyzed by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) can be biosynthesized from CDP-choline and DG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) and L-serine can be converted into choline and PS(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)); which is catalyzed by the enzyme phosphatidylserine synthase. In cattle, PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) pathway. 1,2-Dig-linolenoyl-rac-glycero-3-phosphocholine Phosphatidylcholine(36:6) GPCho(18:3/18:3) PC(18:3/18:3) GPCho(36:6) Phosphatidylcholine(18:3/18:3) Lecithin PC(36:6) 1,2-Di(6Z,9Z,12Z-octadecatrienoyl)-rac-glycero-3-phosphocholine PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) 1,2-Digamma-linolenoyl-GPC 1,2-Digamma-linolenoyl-sn-glycero-3-phosphocholine 1,2-Digamma-linolenoyl-sn-glycero-phosphatidylcholine 1,2-Dilinolenoyl-GPC GPC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) GPC(18:3/18:3) GPC(18:3n6/18:3n6) GPC(18:3w6/18:3w6) GPC(36:6) GPCho(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) GPCho(18:3n6/18:3n6) GPCho(18:3w6/18:3w6) PC(18:3n6/18:3n6) PC(18:3w6/18:3w6) Phosphatidylcholine(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) Phosphatidylcholine(18:3n6/18:3n6) Phosphatidylcholine(18:3w6/18:3w6) C44H76NO8P 778.0499 777.530854925 (2-{[(2R)-2,3-bis[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium (2-{[(2R)-2,3-bis[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium [H][C@@](COC(=O)CCCC\C=C/C\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/CCCCC 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/h14-17,20-23,26-29,42H,6-13,18-19,24-25,30-41H2,1-5H3/b16-14-,17-15-,22-20-,23-21-,28-26-,29-27-/t42-/m1/s1 YNQXQNOLOMVDLG-HJYHAXFASA-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 5.39 ALOGPS logs -7.39 ALOGPS logp 7.72 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac (2-{[(2R)-2,3-bis[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium ChemAxon average_mass 778.0499 ChemAxon mono_mass 777.530854925 ChemAxon smiles [H][C@@](COC(=O)CCCC\C=C/C\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/CCCCC 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/h14-17,20-23,26-29,42H,6-13,18-19,24-25,30-41H2,1-5H3/b16-14-,17-15-,22-20-,23-21-,28-26-,29-27-/t42-/m1/s1 ChemAxon inchikey YNQXQNOLOMVDLG-HJYHAXFASA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 240.97 ChemAxon polarizability 91.3 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(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) SMP0080655 Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) SMP0082460 Specdb::MsMs 304528 Specdb::MsMs 304529 Specdb::MsMs 304530 Specdb::MsMs 347761 Specdb::MsMs 347762 Specdb::MsMs 347763 Specdb::MsMs 2585000 Specdb::MsMs 2585001 Specdb::MsMs 2585002 Specdb::MsMs 2665396 Specdb::MsMs 2665397 Specdb::MsMs 2665398 Specdb::MsMs 2691854 Specdb::MsMs 2691855 Specdb::MsMs 2691856 Specdb::MsMs 3016710 Specdb::MsMs 3016711 Specdb::MsMs 3016712 Specdb::MsMs 3064206 Specdb::MsMs 3064207 Specdb::MsMs 3064208 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 24766834 52922787 89557