1.0 2016-09-30 23:48:12 UTC 2020-06-04 20:44:54 UTC BMDB0007973 BMDB07973 PC(16:0/18:2(9Z,12Z)) PC(16:0/18:2(9Z,12Z)), also known as GPC(16:0/18:2) or gpcho 16:0/18:2(9Z,12Z), 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(16:0/18:2(9Z,12Z)) is considered to be a glycerophosphocholine lipid molecule. PC(16:0/18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:0/18:2(9Z,12Z)) exists in all eukaryotes, ranging from yeast to humans. PC(16:0/18:2(9Z,12Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(16:0/18:2(9Z,12Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(16:0/18:2(9Z,12Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(16:0/18:2(9Z,12Z)) can be biosynthesized from CDP-choline and DG(16:0/18:2(9Z,12Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PC(16:0/18:2(9Z,12Z)) and L-serine can be converted into choline and PS(16:0/18:2(9Z,12Z)) through the action of the enzyme phosphatidylserine synthase. In cattle, PC(16:0/18:2(9Z,12Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(16:0/18:2(9Z,12Z)) pathway and phosphatidylethanolamine biosynthesis pe(16:0/18:2(9Z,12Z)) pathway. 1-Palmitoyl-2-linoleoyl-GPC 1-Palmitoyl-2-linoleoyl-GPC (16:0/18:2) 1-Palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine 1-Palmitoyl-2-linoleoyl-sn-glycero-phosphatidylcholine 1-Palmitoyl-2-linoleoyl-sn-glycerophosphatidylcholine 1-Palmitoyl-2-linoleoylphosphatidylcholine GPC(16:0/18:2) GPCho 16:0/18:2(9Z,12Z) GPCho(16:0/18:2(9Z,12Z)) GPCho(16:0/18:2) GPCho(16:0/18:2omega6) Lecithin PC 16:0/18:2(9Z,12Z) PC(16:0/18:2) PC(16:0/18:2omega6) PC(34:2) Phosphatidylcholine 16:0/18:2(9Z,12Z) Phosphatidylcholine(16:0/18:2(9Z,12Z)) Phosphatidylcholine(16:0/18:2) Phosphatidylcholine(16:0/18:2omega6) Gpcho(34:2) Phosphatidylcholine(34:2) 2-Linoleoyl-1-palmitoyl-sn-phosphatidylcholine Palmitoyl-linoleoatephosphatidylcholine PLPC 1-Hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine 1-Palmitoyl-2-linoleoyl-3-phosphatidylcholine 1-Palmitoyl-2-linoleoyl-3-sn-glycerophosphatidylcholine 1-Palmitoyl-2-linoleoyl-3-sn-phosphatidylcholine 1-Palmitoyl-2-linoleoyl-sn-glycero-3-phosphatidylcholine 1-Palmitoyl-2-linoleoyllecithin GPC(16:0/18:2(9Z,12Z)) GPC(16:0/18:2n6) GPC(16:0/18:2W6) GPC(34:2) GPCho(16:0/18:2n6) GPCho(16:0/18:2W6) L-alpha-1-Palmitoyl-2-linoleoylphosphatidylcholine L-Α-1-palmitoyl-2-linoleoylphosphatidylcholine PC(16:0/18:2n6) PC(16:0/18:2W6) Phosphatidylcholine(16:0/18:2n6) Phosphatidylcholine(16:0/18:2W6) PC(16:0/18:2(9Z,12Z)) C42H80NO8P 758.0603 757.562155053 (2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium (2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium 17708-90-6 [H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC 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/h14,16,20-21,40H,6-13,15,17-19,22-39H2,1-5H3/b16-14-,21-20-/t40-/m1/s1 JLPULHDHAOZNQI-ZTIMHPMXSA-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 5.48 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-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium ChemAxon average_mass 758.0603 ChemAxon mono_mass 757.562155053 ChemAxon smiles [H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC 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/h14,16,20-21,40H,6-13,15,17-19,22-39H2,1-5H3/b16-14-,21-20-/t40-/m1/s1 ChemAxon inchikey JLPULHDHAOZNQI-ZTIMHPMXSA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 227.3 ChemAxon polarizability 92.66 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(16:0/18:2(9Z,12Z)) SMP0080519 Phosphatidylethanolamine Biosynthesis PE(16:0/18:2(9Z,12Z)) SMP0082322 Specdb::CMs 241778 Specdb::NmrOneD 291495 Specdb::NmrOneD 291496 Specdb::NmrOneD 291497 Specdb::NmrOneD 291498 Specdb::NmrOneD 291499 Specdb::NmrOneD 291500 Specdb::NmrOneD 291501 Specdb::NmrOneD 291502 Specdb::NmrOneD 291503 Specdb::NmrOneD 291504 Specdb::NmrOneD 291505 Specdb::NmrOneD 291506 Specdb::NmrOneD 291507 Specdb::NmrOneD 291508 Specdb::NmrOneD 291509 Specdb::NmrOneD 291510 Specdb::NmrOneD 291511 Specdb::NmrOneD 291512 Specdb::NmrOneD 291513 Specdb::NmrOneD 291514 Specdb::MsMs 565315 Specdb::MsMs 565316 Specdb::MsMs 565317 Specdb::MsMs 1472856 Specdb::MsMs 1472857 Specdb::MsMs 1472858 Specdb::MsMs 1472859 Specdb::MsMs 1472860 Specdb::MsMs 1472861 Specdb::MsMs 1472862 Specdb::MsMs 1472863 Specdb::MsMs 1472864 Specdb::MsMs 1472865 Specdb::MsMs 1472866 Specdb::MsMs 1472867 Specdb::MsMs 1472868 Specdb::MsMs 1472869 Specdb::MsMs 1472870 Specdb::MsMs 1472871 Specdb::MsMs 1472872 Specdb::MsMs 1472873 Specdb::MsMs 1472874 Specdb::MsMs 1472875 Specdb::MsMs 1472876 Specdb::MsMs 1472877 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 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 0.535 +/- 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 5287971 73002 CPL FDB030253 DB02306 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) BMDBP02841 Phosphatidylserine synthase 1 Q2KHY9 PTDSS1 Enzyme