1.0 2016-09-30 23:46:10 UTC 2020-06-04 19:46:41 UTC BMDB0007874 BMDB07874 PC(14:0/18:2(9Z,12Z)) PC(14:0/18:2(9Z,12Z)), also known as gpcho(14:0/18:2) or PC(32:2), 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(14:0/18:2(9Z,12Z)) is considered to be a glycerophosphocholine lipid molecule. PC(14:0/18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(14:0/18:2(9Z,12Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(14:0/18:2(9Z,12Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(14:0/18:2(9Z,12Z)) through the action of the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(14:0/18:2(9Z,12Z)) can be biosynthesized from CDP-choline and DG(14:0/18:2(9Z,12Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PC(14:0/18:2(9Z,12Z)) and L-serine can be converted into choline and PS(14:0/18:2(9Z,12Z)); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(14:0/18:2(9Z,12Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(14:0/18:2(9Z,12Z)) pathway and phosphatidylethanolamine biosynthesis pe(14:0/18:2(9Z,12Z)) pathway. 1-Myristoyl-2-linoleoyl-sn-glycero-3-phosphocholine 1-Tetradecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine GPCho(14:0/18:2) GPCho(14:0/18:2n6) GPCho(14:0/18:2W6) PC(14:0/18:2) PC(14:0/18:2n6) PC(14:0/18:2W6) Phosphatidylcholine(14:0/18:2) Phosphatidylcholine(14:0/18:2n6) Phosphatidylcholine(14:0/18:2W6) PC(32:2) Lecithin GPCho(32:2) Phosphatidylcholine(32:2) 1-Myristoyl-2-linoleoyl-GPC 1-Myristoyl-2-linoleoyl-sn-glycero-phosphatidylcholine GPC(14:0/18:2(9Z,12Z)) GPC(14:0/18:2) GPC(14:0/18:2n6) GPC(14:0/18:2W6) GPC(32:2) GPCho(14:0/18:2(9Z,12Z)) Phosphatidylcholine(14:0/18:2(9Z,12Z)) PC(14:0/18:2(9Z,12Z)) C40H76NO8P 730.0071 729.530854925 trimethyl(2-{[(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(tetradecanoyloxy)propyl phosphono]oxy}ethyl)azanium trimethyl(2-{[(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(tetradecanoyloxy)propyl phosphono]oxy}ethyl)azanium 92345-33-0 [H][C@@](COC(=O)CCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC InChI=1S/C40H76NO8P/c1-6-8-10-12-14-16-18-19-20-21-23-25-27-29-31-33-40(43)49-38(37-48-50(44,45)47-35-34-41(3,4)5)36-46-39(42)32-30-28-26-24-22-17-15-13-11-9-7-2/h14,16,19-20,38H,6-13,15,17-18,21-37H2,1-5H3/b16-14-,20-19-/t38-/m1/s1 IWXJKHSPEQSQMD-GMGFYYQASA-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 phosphatidylcholine 32:2 Solid logp 5.13 ALOGPS logs -7.43 ALOGPS logp 7.39 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac trimethyl(2-{[(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(tetradecanoyloxy)propyl phosphono]oxy}ethyl)azanium ChemAxon average_mass 730.0071 ChemAxon mono_mass 729.530854925 ChemAxon smiles [H][C@@](COC(=O)CCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC ChemAxon formula C40H76NO8P ChemAxon inchi InChI=1S/C40H76NO8P/c1-6-8-10-12-14-16-18-19-20-21-23-25-27-29-31-33-40(43)49-38(37-48-50(44,45)47-35-34-41(3,4)5)36-46-39(42)32-30-28-26-24-22-17-15-13-11-9-7-2/h14,16,19-20,38H,6-13,15,17-18,21-37H2,1-5H3/b16-14-,20-19-/t38-/m1/s1 ChemAxon inchikey IWXJKHSPEQSQMD-GMGFYYQASA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 218.1 ChemAxon polarizability 88.4 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(14:0/18:2(9Z,12Z)) SMP0080438 Phosphatidylethanolamine Biosynthesis PE(14:0/18:2(9Z,12Z)) SMP0082241 Specdb::MsMs 300400 Specdb::MsMs 300401 Specdb::MsMs 300402 Specdb::MsMs 342670 Specdb::MsMs 342671 Specdb::MsMs 342672 Specdb::MsMs 2270146 Specdb::MsMs 2270147 Specdb::MsMs 2270148 Specdb::MsMs 2615604 Specdb::MsMs 2615605 Specdb::MsMs 2615606 Specdb::MsMs 2683707 Specdb::MsMs 2683708 Specdb::MsMs 2683709 Specdb::MsMs 3072735 Specdb::MsMs 3072736 Specdb::MsMs 3072737 Specdb::MsMs 3087139 Specdb::MsMs 3087140 Specdb::MsMs 3087141 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 4 +/- 1 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 1.7 +/- 0.4 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 Milk 0.63 +/- 0.01 uM Commercial 1% milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 0.83 +/- 0.02 uM Commercial 2% milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 1.00 +/- 0.05 uM Commercial 3.25% milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 0.61 +/- 0.01 uM Commercial skim milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Ruminal Fluid 0.048 +/- 0.024 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 Ruminal Fluid 0.034 +/- 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. Semimembranosus Muscle 3 +/- 2 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 0.5 +/- 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 24778624 86094 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) BMDBP02841 Phosphatidylserine synthase 1 Q2KHY9 PTDSS1 Enzyme