1.0 2016-09-30 23:48:50 UTC 2020-06-04 20:44:55 UTC BMDB0008005 BMDB08005 PC(16:1(9Z)/18:1(9Z)) PC(16:1(9Z)/18:1(9Z)), also known as gpcho(16:1/18:1) or gpcho(34:2), 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(16:1(9Z)/18:1(9Z)) is considered to be a glycerophosphocholine lipid molecule. PC(16:1(9Z)/18:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:1(9Z)/18:1(9Z)) exists in all eukaryotes, ranging from yeast to humans. PC(16:1(9Z)/18:1(9Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(16:1(9Z)/18:1(9Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(16:1(9Z)/18:1(9Z)); which is mediated by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(16:1(9Z)/18:1(9Z)) can be biosynthesized from CDP-choline and DG(16:1(9Z)/18:1(9Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PC(16:1(9Z)/18:1(9Z)) and L-serine can be converted into choline and PS(16:1(9Z)/18:1(9Z)) through its interaction with the enzyme phosphatidylserine synthase. In cattle, PC(16:1(9Z)/18:1(9Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(16:1(9Z)/18:1(9Z)) pathway and phosphatidylethanolamine biosynthesis pe(16:1(9Z)/18:1(9Z)) pathway. 1-Palmitoleoyl-2-oleoyl-sn-glycero-3-phosphocholine GPCho(16:1/18:1) GPCho(16:1n7/18:1n9) GPCho(16:1W7/18:1W9) GPCho(34:2) PC(16:1/18:1) PC(16:1n7/18:1n9) PC(16:1W7/18:1W9) Phosphatidylcholine(16:1/18:1) Phosphatidylcholine(16:1n7/18:1n9) Phosphatidylcholine(16:1W7/18:1W9) Lecithin PC Aa C34:2 PC(34:2) Phosphatidylcholine(34:2) 1-(9Z-Hexadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine PC(16:1(9Z)/18:1(9Z)) C42H80NO8P 758.0603 757.562155053 (2-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium lecithin CCCCCCCC\C=C/CCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)COP([O-])(=O)OCC[N+](C)(C)C InChI=1S/C42H80NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h17,19-21,40H,6-16,18,22-39H2,1-5H3/b19-17-,21-20-/t40-/m1/s1 ZRCWDIULNHKQRD-RWGOWQMXSA-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 34:2 Solid logp 5.45 ALOGPS logs -7.51 ALOGPS logp 8.28 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac (2-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium ChemAxon average_mass 758.0603 ChemAxon mono_mass 757.562155053 ChemAxon smiles CCCCCCCC\C=C/CCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)COP([O-])(=O)OCC[N+](C)(C)C ChemAxon formula C42H80NO8P ChemAxon inchi InChI=1S/C42H80NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h17,19-21,40H,6-16,18,22-39H2,1-5H3/b19-17-,21-20-/t40-/m1/s1 ChemAxon inchikey ZRCWDIULNHKQRD-RWGOWQMXSA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 227.3 ChemAxon polarizability 92.23 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(16:1(9Z)/18:1(9Z)) SMP0080543 Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:1(9Z)) SMP0082346 Specdb::NmrOneD 261208 Specdb::NmrOneD 261209 Specdb::NmrOneD 261210 Specdb::NmrOneD 261211 Specdb::NmrOneD 261212 Specdb::NmrOneD 261213 Specdb::NmrOneD 261214 Specdb::NmrOneD 261215 Specdb::NmrOneD 261216 Specdb::NmrOneD 261217 Specdb::NmrOneD 261218 Specdb::NmrOneD 261219 Specdb::NmrOneD 261220 Specdb::NmrOneD 261221 Specdb::NmrOneD 261222 Specdb::NmrOneD 261223 Specdb::NmrOneD 261224 Specdb::NmrOneD 261225 Specdb::NmrOneD 261226 Specdb::NmrOneD 261227 Specdb::MsMs 183433 Specdb::MsMs 327685 Specdb::MsMs 327686 Specdb::MsMs 327687 Specdb::MsMs 2416582 Specdb::MsMs 2416583 Specdb::MsMs 2416584 Specdb::MsMs 2548717 Specdb::MsMs 2548718 Specdb::MsMs 2548719 Specdb::MsMs 2619116 Specdb::MsMs 2619117 Specdb::MsMs 2619118 Specdb::MsMs 2672735 Specdb::MsMs 2672736 Specdb::MsMs 2672737 Specdb::MsMs 3084988 Specdb::MsMs 3084989 Specdb::MsMs 3084990 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 11.0 +/- 0.4 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 7.7 +/- 0.1 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 9.5 +/- 0.5 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 6.9 +/- 0.1 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 0.535 +/- 0.32 uM Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). 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. Ruminal Fluid 0.431 +/- 0.41 uM Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). 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. Ruminal Fluid 0.345 +/- 0.22 uM Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). 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. Ruminal Fluid 0.781 +/- 0.66 uM Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. 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. Ruminal Fluid 0.041 uM By direct flow injection MS/MS. Daily cows fed barley grains (15% of diet dry matter) (n=8) Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7. 22959937 Ruminal Fluid 0.028 uM By direct flow injection MS/MS. Daily cows fed barley grains (30% of diet dry matter) (n=8) Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7. 22959937 Ruminal Fluid 0.038 uM By direct flow injection MS/MS. Daily cows fed barley grains (45% of diet dry matter) (n=8) Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7. 22959937 Ruminal Fluid 0.73 uM By direct flow injection MS/MS. No barley grains in diet (n=8) Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7. 22959937 24766674 24778767 84811 FDB025196 C00157 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) BMDBP02841 Phosphatidylserine synthase 1 Q2KHY9 PTDSS1 Enzyme