1.0 2016-09-30 23:46:46 UTC 2020-06-04 19:51:03 UTC BMDB0007904 BMDB07904 PC(14:1(9Z)/18:0) PC(14:1(9Z)/18:0), also known as gpcho(14:1/18:0) or gpcho(32:1), 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)/18:0) is considered to be a glycerophosphocholine lipid molecule. PC(14:1(9Z)/18:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(14:1(9Z)/18:0) exists in all eukaryotes, ranging from yeast to humans. PC(14:1(9Z)/18:0) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(14:1(9Z)/18:0) can be biosynthesized from S-adenosylmethionine and pe-nme2(14:1(9Z)/18:0); which is mediated by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(14:1(9Z)/18:0) can be biosynthesized from CDP-choline and DG(14:1(9Z)/18:0/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PC(14:1(9Z)/18:0) and L-serine can be converted into choline and PS(14:1(9Z)/18:0) through its interaction with the enzyme phosphatidylserine synthase. In cattle, PC(14:1(9Z)/18:0) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(14:1(9Z)/18:0) pathway and phosphatidylethanolamine biosynthesis pe(14:1(9Z)/18:0) pathway. GPCho(14:1/18:0) 1-Myristoleoyl-2-stearoyl-sn-glycero-3-phosphocholine GPCho(32:1) Phosphatidylcholine(14:1/18:0) PC(14:1/18:0) Phosphatidylcholine(32:1) PC(32:1) 1-(9Z-Tetradecenoyl)-2-octadecanoyl-sn-glycero-3-phosphocholine Lecithin PC(14:1(9Z)/18:0) C40H78NO8P 732.023 731.546504989 trimethyl(2-{[(2R)-2-(octadecanoyloxy)-3-[(9Z)-tetradec-9-enoyloxy]propyl phosphonato]oxy}ethyl)azanium lecithin CCCCCCCCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/CCCC)COP([O-])(=O)OCC[N+](C)(C)C InChI=1S/C40H78NO8P/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/h13,15,38H,6-12,14,16-37H2,1-5H3/b15-13-/t38-/m1/s1 USMRUWLOXQOAAX-IUXSEFJDSA-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 5.27 ALOGPS logs -7.48 ALOGPS logp 7.75 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac trimethyl(2-{[(2R)-2-(octadecanoyloxy)-3-[(9Z)-tetradec-9-enoyloxy]propyl phosphonato]oxy}ethyl)azanium ChemAxon average_mass 732.023 ChemAxon mono_mass 731.546504989 ChemAxon smiles CCCCCCCCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/CCCC)COP([O-])(=O)OCC[N+](C)(C)C ChemAxon formula C40H78NO8P ChemAxon inchi InChI=1S/C40H78NO8P/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/h13,15,38H,6-12,14,16-37H2,1-5H3/b15-13-/t38-/m1/s1 ChemAxon inchikey USMRUWLOXQOAAX-IUXSEFJDSA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 216.98 ChemAxon polarizability 89.72 ChemAxon rotatable_bond_count 39 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)/18:0) SMP0080463 Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:0) SMP0082266 Specdb::NmrOneD 316201 Specdb::NmrOneD 316202 Specdb::NmrOneD 316203 Specdb::NmrOneD 316204 Specdb::NmrOneD 316205 Specdb::NmrOneD 316206 Specdb::NmrOneD 316207 Specdb::NmrOneD 316208 Specdb::NmrOneD 316209 Specdb::NmrOneD 316210 Specdb::NmrOneD 316211 Specdb::NmrOneD 316212 Specdb::NmrOneD 316213 Specdb::NmrOneD 316214 Specdb::NmrOneD 316215 Specdb::NmrOneD 316216 Specdb::NmrOneD 316217 Specdb::NmrOneD 316218 Specdb::NmrOneD 316219 Specdb::NmrOneD 316220 Specdb::MsMs 184493 Specdb::MsMs 364273 Specdb::MsMs 364274 Specdb::MsMs 364275 Specdb::MsMs 2596060 Specdb::MsMs 2596061 Specdb::MsMs 2596062 Specdb::MsMs 2694765 Specdb::MsMs 2694766 Specdb::MsMs 2694767 Specdb::MsMs 2751694 Specdb::MsMs 2751695 Specdb::MsMs 2751696 Specdb::MsMs 2930436 Specdb::MsMs 2930437 Specdb::MsMs 2930438 Specdb::MsMs 3110462 Specdb::MsMs 3110463 Specdb::MsMs 3110464 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 3.51 +/- 0.03 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 4.2 +/- 0.1 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 5.2 +/- 0.1 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 3.18 +/- 0.02 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 52922260 88907 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) BMDBP02841 Phosphatidylserine synthase 1 Q2KHY9 PTDSS1 Enzyme