1.0 2016-10-03 17:17:38 UTC 2020-06-04 19:29:34 UTC BMDB0008276 BMDB08276 PC(20:0/20:2(11Z,14Z)) PC(20:0/20:2(11Z,14Z)), also known as gpcho(20:0/20:2n6) or PC(40:2), 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(20:0/20:2(11Z,14Z)) is considered to be a glycerophosphocholine lipid molecule. PC(20:0/20:2(11Z,14Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(20:0/20:2(11Z,14Z)) exists in all eukaryotes, ranging from yeast to humans. PC(20:0/20:2(11Z,14Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(20:0/20:2(11Z,14Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(20:0/20:2(11Z,14Z)); which is mediated by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(20:0/20:2(11Z,14Z)) can be biosynthesized from CDP-choline and DG(20:0/20:2(11Z,14Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PC(20:0/20:2(11Z,14Z)) and L-serine can be converted into choline and PS(20:0/20:2(11Z,14Z)) through its interaction with the enzyme phosphatidylserine synthase. In cattle, PC(20:0/20:2(11Z,14Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(20:0/20:2(11Z,14Z)) pathway and phosphatidylethanolamine biosynthesis pe(20:0/20:2(11Z,14Z)) pathway. 1-Arachidonyl-2-eicosadienoyl-sn-glycero-3-phosphocholine GPCho(20:0/20:2n6) GPCho(20:0/20:2W6) PC(20:0/20:2n6) PC(20:0/20:2W6) Phosphatidylcholine(20:0/20:2n6) Phosphatidylcholine(20:0/20:2W6) PC(40:2) PC(20:0/20:2(11Z,14Z)) Phosphatidylcholine(20:0/20:2) Lecithin GPCho(20:0/20:2) GPCho(40:2) PC(20:0/20:2) 1-eicosanoyl-2-(11Z,14Z-eicosadienoyl)-sn-glycero-3-phosphocholine Phosphatidylcholine(40:2) C48H92NO8P 842.2197 841.656055437 (2-{[(2R)-2-[(11Z,14Z)-icosa-11,14-dienoyloxy]-3-(icosanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium (2-{[(2R)-2-[(11Z,14Z)-icosa-11,14-dienoyloxy]-3-(icosanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium [H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC InChI=1S/C48H92NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-47(50)54-44-46(45-56-58(52,53)55-43-42-49(3,4)5)57-48(51)41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h15,17,21,23,46H,6-14,16,18-20,22,24-45H2,1-5H3/b17-15-,23-21-/t46-/m1/s1 DGKXFLANAYRYMU-BYZVZMPQSA-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 40:2 Solid logp 6.39 ALOGPS logs -7.58 ALOGPS logp 10.95 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac (2-{[(2R)-2-[(11Z,14Z)-icosa-11,14-dienoyloxy]-3-(icosanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium ChemAxon average_mass 842.2197 ChemAxon mono_mass 841.656055437 ChemAxon smiles [H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC ChemAxon formula C48H92NO8P ChemAxon inchi InChI=1S/C48H92NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-47(50)54-44-46(45-56-58(52,53)55-43-42-49(3,4)5)57-48(51)41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h15,17,21,23,46H,6-14,16,18-20,22,24-45H2,1-5H3/b17-15-,23-21-/t46-/m1/s1 ChemAxon inchikey DGKXFLANAYRYMU-BYZVZMPQSA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 254.91 ChemAxon polarizability 105.34 ChemAxon rotatable_bond_count 46 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(20:0/20:2(11Z,14Z)) SMP0080714 Phosphatidylethanolamine Biosynthesis PE(20:0/20:2(11Z,14Z)) SMP0082522 Specdb::CMs 222423 Specdb::MsMs 290836 Specdb::MsMs 290837 Specdb::MsMs 290838 Specdb::MsMs 330592 Specdb::MsMs 330593 Specdb::MsMs 330594 Specdb::MsMs 2416558 Specdb::MsMs 2416559 Specdb::MsMs 2416560 Specdb::MsMs 2790593 Specdb::MsMs 2790594 Specdb::MsMs 2790595 Specdb::MsMs 2875022 Specdb::MsMs 2875023 Specdb::MsMs 2875024 Specdb::MsMs 2915819 Specdb::MsMs 2915820 Specdb::MsMs 2915821 Specdb::MsMs 2953812 Specdb::MsMs 2953813 Specdb::MsMs 2953814 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 Blood 0.4 +/- 0.1 uM By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Liver 0.7 +/- 0.2 nmol/g of tissue By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Longissimus Thoracis Muscle 0.017 +/- 0.004 nmol/g of tissue By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Milk 0.026 +/- 0.003 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 0.032 +/- 0.003 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 0.038 +/- 0.003 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 0.025 +/- 0.002 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 Semimembranosus Muscle 0.02 +/- 0.01 nmol/g of tissue By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Testis 0.12 +/- 0.02 nmol/g of tissue By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 24766937 86199 24779046 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)