1.0 2016-09-30 23:46:59 UTC 2020-06-04 19:20:10 UTC BMDB0007915 BMDB07915 PC(14:1(9Z)/20:3(8Z,11Z,14Z)) PC(14:1(9Z)/20:3(8Z,11Z,14Z)), also known as phosphatidylcholine(34:4) or gpcho(34:4), 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(14:1(9Z)/20:3(8Z,11Z,14Z)) is considered to be a glycerophosphocholine lipid molecule. PC(14:1(9Z)/20:3(8Z,11Z,14Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(14:1(9Z)/20:3(8Z,11Z,14Z)) exists in all eukaryotes, ranging from yeast to humans. PC(14:1(9Z)/20:3(8Z,11Z,14Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(14:1(9Z)/20:3(8Z,11Z,14Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(14:1(9Z)/20:3(8Z,11Z,14Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(14:1(9Z)/20:3(8Z,11Z,14Z)) can be biosynthesized from CDP-choline and DG(14:1(9Z)/20:3(8Z,11Z,14Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(14:1(9Z)/20:3(8Z,11Z,14Z)) and L-serine can be converted into choline and PS(14:1(9Z)/20:3(8Z,11Z,14Z)); which is catalyzed by the enzyme phosphatidylserine synthase. In cattle, PC(14:1(9Z)/20:3(8Z,11Z,14Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(14:1(9Z)/20:3(8Z,11Z,14Z)) pathway and phosphatidylethanolamine biosynthesis pe(14:1(9Z)/20:3(8Z,11Z,14Z)) pathway. Phosphatidylcholine(34:4) GPCho(34:4) Phosphatidylcholine(14:1/20:3) PC(14:1(9Z)/20:3(8Z,11Z,14Z)) PC(34:4) Lecithin PC(14:1/20:3) 1-myristoleoyl-2-homo-g-linolenoyl-sn-glycero-3-phosphocholine 1-(9Z-tetradecenoyl)-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycero-3-phosphocholine GPCho(14:1/20:3) C42H76NO8P 754.0285 753.530854925 (2-{[(2R)-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-3-[(9Z)-tetradec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium lecithin CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/CCCC)COP([O-])(=O)OCC[N+](C)(C)C InChI=1S/C42H76NO8P/c1-6-8-10-12-14-16-18-19-20-21-22-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-17-15-13-11-9-7-2/h13-16,19-20,22-23,40H,6-12,17-18,21,24-39H2,1-5H3/b15-13-,16-14-,20-19-,23-22-/t40-/m1/s1 MGHZJKXUBUUNJR-PCBJBAEXSA-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 5.30 ALOGPS logs -7.40 ALOGPS logp 7.56 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac (2-{[(2R)-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-3-[(9Z)-tetradec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium ChemAxon average_mass 754.0285 ChemAxon mono_mass 753.530854925 ChemAxon smiles CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/CCCC)COP([O-])(=O)OCC[N+](C)(C)C ChemAxon formula C42H76NO8P ChemAxon inchi InChI=1S/C42H76NO8P/c1-6-8-10-12-14-16-18-19-20-21-22-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-17-15-13-11-9-7-2/h13-16,19-20,22-23,40H,6-12,17-18,21,24-39H2,1-5H3/b15-13-,16-14-,20-19-,23-22-/t40-/m1/s1 ChemAxon inchikey MGHZJKXUBUUNJR-PCBJBAEXSA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 229.53 ChemAxon polarizability 90.1 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(14:1(9Z)/20:3(8Z,11Z,14Z)) SMP0080474 Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:3(8Z,11Z,14Z)) SMP0082277 Specdb::CMs 198248 Specdb::MsMs 294301 Specdb::MsMs 294302 Specdb::MsMs 294303 Specdb::MsMs 334975 Specdb::MsMs 334976 Specdb::MsMs 334977 Specdb::MsMs 2267247 Specdb::MsMs 2267248 Specdb::MsMs 2267249 Specdb::MsMs 2332859 Specdb::MsMs 2332860 Specdb::MsMs 2332861 Specdb::MsMs 2834301 Specdb::MsMs 2834302 Specdb::MsMs 2834303 Specdb::MsMs 2871881 Specdb::MsMs 2871882 Specdb::MsMs 2871883 Specdb::MsMs 3018981 Specdb::MsMs 3018982 Specdb::MsMs 3018983 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 Milk 0.081 +/- 0.004 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 0.10 +/- 0.01 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 0.13 +/- 0.01 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 0.074 +/- 0.004 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 0.009 +/- 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. 24766591 52922282 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) BMDBP02841 Phosphatidylserine synthase 1 Q2KHY9 PTDSS1 Enzyme