1.0 2016-09-30 23:49:31 UTC 2020-06-04 20:44:42 UTC BMDB0008039 BMDB08039 PC(18:0/18:2(9Z,12Z)) PC(18:0/18:2(9Z,12Z)), also known as PC(18:0/18:2) or 18:0-18:2-PC, 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(18:0/18:2(9Z,12Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:0/18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:0/18:2(9Z,12Z)) exists in all eukaryotes, ranging from yeast to humans. PC(18:0/18:2(9Z,12Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:0/18:2(9Z,12Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:0/18:2(9Z,12Z)); which is mediated by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:0/18:2(9Z,12Z)) can be biosynthesized from CDP-choline and DG(18:0/18:2(9Z,12Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:0/18:2(9Z,12Z)) and L-serine can be converted into choline and PS(18:0/18:2(9Z,12Z)) through its interaction with the enzyme phosphatidylserine synthase. In cattle, PC(18:0/18:2(9Z,12Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:0/18:2(9Z,12Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:0/18:2(9Z,12Z)) pathway. 1-18:0-2-18:2-Phosphatidylcholine 1-Octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholine 1-Stearoyl-2-linoleoyl-GPC 1-Stearoyl-2-linoleoyl-GPC (18:0/18:2) 1-Stearoyl-2-linoleoyl-sn-glycero-3-phosphatidylcholine 18:0-18:2-PC GPC(18:0/18:2) GPCho(18:0/18:2) GPCho(18:0/18:2n6) GPCho(18:0/18:2W6) GPCho(36:2) PC(18:0/18:2) PC(18:0/18:2n6) PC(18:0/18:2W6) PC(36:2) Phosphatidylcholine (1-18:0-2-18:2) Phosphatidylcholine(18:0/18:2) Phosphatidylcholine(18:0/18:2n6) Phosphatidylcholine(36:2) SLPC SLPTC 1-Stearoyl-(2-linoleoyl)-sn-glycero-3-phosphocholine 1-stearoyl-2-linoleoyl-sn-glycero-3-phosphocholine Lecithin PC(18:0/18:2(9Z,12Z)) 1-octadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine 1-Stearoyl-2-linoleoylphosphatidylcholine 1-Stearoyl-2-linoleoyl-sn-glycero-3-phosphorylcholine 1-Stearoyl-2-linoleoyl-sn-glycero-phosphatidylcholine 1-Stearoyl-2-linoleoyllecithin 1-Stearyl-2-linoleoyl-3-sn-glycerophosphatidylcholine GPC(18:0/18:2(9Z,12Z)) GPC(18:0/18:2n6) GPC(18:0/18:2w6) GPC(36:2) GPCho(18:0/18:2(9Z,12Z)) Phosphatidylcholine(18:0/18:2(9Z,12Z)) Phosphatidylcholine(18:0/18:2w6) C44H84NO8P 786.1134 785.593455181 trimethyl(2-{[(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)azanium lecithin 27098-24-4 CCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC InChI=1S/C44H84NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h15,17,21,23,42H,6-14,16,18-20,22,24-41H2,1-5H3/b17-15-,23-21-/t42-/m1/s1 FORFDCPQKJHEBF-VPUSDGANSA-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 36:2 Solid logp 5.80 ALOGPS logs -7.58 ALOGPS logp 9.17 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-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)azanium ChemAxon average_mass 786.1134 ChemAxon mono_mass 785.593455181 ChemAxon smiles CCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC ChemAxon formula C44H84NO8P ChemAxon inchi InChI=1S/C44H84NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h15,17,21,23,42H,6-14,16,18-20,22,24-41H2,1-5H3/b17-15-,23-21-/t42-/m1/s1 ChemAxon inchikey FORFDCPQKJHEBF-VPUSDGANSA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 236.5 ChemAxon polarizability 96.05 ChemAxon rotatable_bond_count 42 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(18:0/18:2(9Z,12Z)) SMP0080568 Phosphatidylethanolamine Biosynthesis PE(18:0/18:2(9Z,12Z)) SMP0082371 Specdb::MsMs 646060 Specdb::MsMs 646061 Specdb::MsMs 646062 Specdb::MsMs 2598898 Specdb::MsMs 2598899 Specdb::MsMs 2598900 Specdb::MsMs 2705603 Specdb::MsMs 2705604 Specdb::MsMs 2705605 Specdb::MsMs 2719668 Specdb::MsMs 2719669 Specdb::MsMs 2719670 Specdb::MsMs 2958933 Specdb::MsMs 2958934 Specdb::MsMs 2958935 Specdb::MsMs 3101468 Specdb::MsMs 3101469 Specdb::MsMs 3101470 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 5.82 +/- 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 7.0 +/- 0.2 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 9.5 +/- 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 5.48 +/- 0.03 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 Placenta 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 Ruminal Fluid 0.263 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 0.104 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 0.019 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 0.642 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 Ruminal Fluid 0.564 +/- 0.381 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 0.501 +/- 0.341 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 0.531 +/- 0.436 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 0.601 +/- 0.735 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. 4945645 6441487 84822 CPD-8279 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) BMDBP02841 Phosphatidylserine synthase 1 Q2KHY9 PTDSS1 Enzyme