1.0 2016-10-03 17:21:19 UTC 2020-06-04 20:05:12 UTC BMDB0008434 BMDB08434 PC(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)) PC(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)), also known as gpcho(20:4n6/18:2n6) or phosphatidylcholine(20:4n6/18:2n6), 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(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)) is considered to be a glycerophosphocholine lipid molecule. PC(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)) exists in all eukaryotes, ranging from yeast to humans. 1-Arachidonoyl-2-linoleoyl-sn-glycero-3-phosphocholine GPCho(20:4n6/18:2n6) GPCho(20:4W6/18:2W6) PC(20:4n6/18:2n6) PC(20:4W6/18:2W6) Phosphatidylcholine(20:4n6/18:2n6) Phosphatidylcholine(20:4W6/18:2W6) PC(38:6) GPCho(38:6) GPCho(20:4/18:2) Phosphatidylcholine(38:6) Lecithin PC(20:4/18:2) 1-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Phosphatidylcholine(20:4/18:2) PC(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)) C46H80NO8P 806.1031 805.562155053 (2-{[(2R)-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium (2-{[(2R)-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium [H][C@@](COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC InChI=1S/C46H80NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-26-28-30-32-34-36-38-45(48)52-42-44(43-54-56(50,51)53-41-40-47(3,4)5)55-46(49)39-37-35-33-31-29-27-24-21-19-17-15-13-11-9-7-2/h14-17,20-22,24-26,30,32,44H,6-13,18-19,23,27-29,31,33-43H2,1-5H3/b16-14-,17-15-,22-20-,24-21-,26-25-,32-30-/t44-/m1/s1 PLZBTDKJYHXIEW-DZUXOTHRSA-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 38:6 Solid logp 5.73 ALOGPS logs -7.44 ALOGPS logp 8.61 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac (2-{[(2R)-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium ChemAxon average_mass 806.1031 ChemAxon mono_mass 805.562155053 ChemAxon smiles [H][C@@](COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC ChemAxon formula C46H80NO8P ChemAxon inchi InChI=1S/C46H80NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-26-28-30-32-34-36-38-45(48)52-42-44(43-54-56(50,51)53-41-40-47(3,4)5)55-46(49)39-37-35-33-31-29-27-24-21-19-17-15-13-11-9-7-2/h14-17,20-22,24-26,30,32,44H,6-13,18-19,23,27-29,31,33-43H2,1-5H3/b16-14-,17-15-,22-20-,24-21-,26-25-,32-30-/t44-/m1/s1 ChemAxon inchikey PLZBTDKJYHXIEW-DZUXOTHRSA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 250.17 ChemAxon polarizability 95.46 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 Specdb::CMs 194872 Specdb::MsMs 296941 Specdb::MsMs 296942 Specdb::MsMs 296943 Specdb::MsMs 338332 Specdb::MsMs 338333 Specdb::MsMs 338334 Specdb::MsMs 2265180 Specdb::MsMs 2265181 Specdb::MsMs 2265182 Specdb::MsMs 2336800 Specdb::MsMs 2336801 Specdb::MsMs 2336802 Specdb::MsMs 2452411 Specdb::MsMs 2452412 Specdb::MsMs 2452413 Specdb::MsMs 2483697 Specdb::MsMs 2483698 Specdb::MsMs 2483699 Specdb::MsMs 3008533 Specdb::MsMs 3008534 Specdb::MsMs 3008535 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 1 +/- 0.3 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 6 +/- 3 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 0.5 +/- 0.1 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 0.151 +/- 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 0.177 +/- 0.002 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 0.22 +/- 0.01 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 0.115 +/- 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 Ruminal Fluid 0.06 +/- 0.04 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 Ruminal Fluid 0.020 +/- 0.014 uM Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured DFI-MS/MS. 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. Semimembranosus Muscle 0.6 +/- 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 Testis 21 +/- 5 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 52923295 86184 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)