1.0 2016-09-30 23:47:31 UTC 2020-06-04 19:48:49 UTC BMDB0007939 BMDB07939 PC(15:0/18:1(9Z)) PC(15:0/18:1(9Z)), also known as PC(15:0/18:1) or PC(33:1), 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(15:0/18:1(9Z)) is considered to be a glycerophosphocholine lipid molecule. PC(15:0/18:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(15:0/18:1(9Z)) exists in all eukaryotes, ranging from yeast to humans. PC(15:0/18:1(9Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(15:0/18:1(9Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(15:0/18:1(9Z)) through the action of the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(15:0/18:1(9Z)) can be biosynthesized from CDP-choline and DG(15:0/18:1(9Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PC(15:0/18:1(9Z)) and L-serine can be converted into choline and PS(15:0/18:1(9Z)); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(15:0/18:1(9Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(15:0/18:1(9Z)) pathway and phosphatidylethanolamine biosynthesis pe(15:0/18:1(9Z)) pathway. 1-Pentadecanoyl-2-(9Z-octadecenoyl)-glycero-3-phosphocholine 1-Pentadecanoyl-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine 1-Pentadecanoyl-2-oleoyl-GPC 1-Pentadecanoyl-2-oleoyl-GPC (15:0/18:1) GPC(15:0/18:1) PC(15:0/18:1) PC(15:0/18:1n9) PC(15:0/18:1W9) PC(33:1) Phosphatidylcholine(15:0/18:1) Phosphatidylcholine(15:0/18:1n9) Phosphatidylcholine(15:0/18:1W9) Phosphatidylcholine(33:1) 1-Pentadecanoyl-2-oleoyl-sn-glycero-3-phosphocholine Gpcho(15:0/18:1) Gpcho(15:0/18:1n9) Gpcho(15:0/18:1W9) Gpcho(33:1) Lecithin 1-Pentadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine PC(15:0/18:1(9Z)) C41H80NO8P 746.0496 745.562155053 trimethyl(2-{[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(pentadecanoyloxy)propyl phosphonato]oxy}ethyl)azanium lecithin CCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC InChI=1S/C41H80NO8P/c1-6-8-10-12-14-16-18-20-21-22-24-26-28-30-32-34-41(44)50-39(38-49-51(45,46)48-36-35-42(3,4)5)37-47-40(43)33-31-29-27-25-23-19-17-15-13-11-9-7-2/h20-21,39H,6-19,22-38H2,1-5H3/b21-20-/t39-/m1/s1 ZEWLMKXMNQOCOQ-KUNNKMQBSA-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 5.43 ALOGPS logs -7.54 ALOGPS logp 8.2 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac trimethyl(2-{[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(pentadecanoyloxy)propyl phosphonato]oxy}ethyl)azanium ChemAxon average_mass 746.0496 ChemAxon mono_mass 745.562155053 ChemAxon smiles CCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC ChemAxon formula C41H80NO8P ChemAxon inchi InChI=1S/C41H80NO8P/c1-6-8-10-12-14-16-18-20-21-22-24-26-28-30-32-34-41(44)50-39(38-49-51(45,46)48-36-35-42(3,4)5)37-47-40(43)33-31-29-27-25-23-19-17-15-13-11-9-7-2/h20-21,39H,6-19,22-38H2,1-5H3/b21-20-/t39-/m1/s1 ChemAxon inchikey ZEWLMKXMNQOCOQ-KUNNKMQBSA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 221.58 ChemAxon polarizability 91.96 ChemAxon rotatable_bond_count 40 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(15:0/18:1(9Z)) SMP0080492 Phosphatidylethanolamine Biosynthesis PE(15:0/18:1(9Z)) SMP0082295 Specdb::MsMs 183875 Specdb::MsMs 334987 Specdb::MsMs 334988 Specdb::MsMs 334989 Specdb::MsMs 2423707 Specdb::MsMs 2423708 Specdb::MsMs 2423709 Specdb::MsMs 2804874 Specdb::MsMs 2804875 Specdb::MsMs 2804876 Specdb::MsMs 2853730 Specdb::MsMs 2853731 Specdb::MsMs 2853732 Specdb::MsMs 2874428 Specdb::MsMs 2874429 Specdb::MsMs 2874430 Specdb::MsMs 2921842 Specdb::MsMs 2921843 Specdb::MsMs 2921844 Specdb::NmrOneD 249328 Specdb::NmrOneD 249329 Specdb::NmrOneD 249330 Specdb::NmrOneD 249331 Specdb::NmrOneD 249332 Specdb::NmrOneD 249333 Specdb::NmrOneD 249334 Specdb::NmrOneD 249335 Specdb::NmrOneD 249336 Specdb::NmrOneD 249337 Specdb::NmrOneD 249338 Specdb::NmrOneD 249339 Specdb::NmrOneD 249340 Specdb::NmrOneD 249341 Specdb::NmrOneD 249342 Specdb::NmrOneD 249343 Specdb::NmrOneD 249344 Specdb::NmrOneD 249345 Specdb::NmrOneD 249346 Specdb::NmrOneD 249347 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 1.45 +/- 0.04 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 2.2 +/- 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 4.1 +/- 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 0.92 +/- 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 24766614 52922312 133623 FDB025131 C00157 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)