1.0 2016-10-03 17:17:33 UTC 2020-06-04 19:31:41 UTC BMDB0008271 BMDB08271 PC(20:0/18:3(6Z,9Z,12Z)) PC(20:0/18:3(6Z,9Z,12Z)), also known as gpcho(20:0/18:3) or gpcho(38:3), 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(20:0/18:3(6Z,9Z,12Z)) is considered to be a glycerophosphocholine lipid molecule. PC(20:0/18:3(6Z,9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(20:0/18:3(6Z,9Z,12Z)) exists in all eukaryotes, ranging from yeast to humans. 1-Arachidonyl-2-g-linolenoyl-sn-glycero-3-phosphocholine 1-Arachidonyl-2-gamma-linolenoyl-sn-glycero-3-phosphocholine Gpcho(20:0/18:3) Gpcho(20:0/18:3n6) Gpcho(20:0/18:3W6) Gpcho(38:3) Lecithin PC Aa C38:3 PC(20:0/18:3) PC(20:0/18:3n6) PC(20:0/18:3W6) PC(38:3) Phosphatidylcholine(20:0/18:3) Phosphatidylcholine(20:0/18:3n6) Phosphatidylcholine(20:0/18:3W6) Phosphatidylcholine(38:3) 1-Eicosanoyl-2-(6Z,9Z,12Z-octadecatrienoyl)-sn-glycero-3-phosphocholine PC(20:0/18:3(6Z,9Z,12Z)) C46H86NO8P 812.1507 811.609105245 (2-{[(2R)-3-(icosanoyloxy)-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium lecithin CCCCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC InChI=1S/C46H86NO8P/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/h15,17,21,24,29,31,44H,6-14,16,18-20,22-23,25-28,30,32-43H2,1-5H3/b17-15-,24-21-,31-29-/t44-/m1/s1 DLZPSAPMHALIOA-YNCVDBFYSA-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 Solid logp 6.08 ALOGPS logs -7.57 ALOGPS logp 9.7 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac (2-{[(2R)-3-(icosanoyloxy)-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium ChemAxon average_mass 812.1507 ChemAxon mono_mass 811.609105245 ChemAxon smiles CCCCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC ChemAxon formula C46H86NO8P ChemAxon inchi InChI=1S/C46H86NO8P/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/h15,17,21,24,29,31,44H,6-14,16,18-20,22-23,25-28,30,32-43H2,1-5H3/b17-15-,24-21-,31-29-/t44-/m1/s1 ChemAxon inchikey DLZPSAPMHALIOA-YNCVDBFYSA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 246.82 ChemAxon polarizability 99.62 ChemAxon rotatable_bond_count 43 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::MsMs 305890 Specdb::MsMs 305891 Specdb::MsMs 305892 Specdb::MsMs 349393 Specdb::MsMs 349394 Specdb::MsMs 349395 Specdb::MsMs 2416504 Specdb::MsMs 2416505 Specdb::MsMs 2416506 Specdb::MsMs 2452339 Specdb::MsMs 2452340 Specdb::MsMs 2452341 Specdb::MsMs 2770499 Specdb::MsMs 2770500 Specdb::MsMs 2770501 Specdb::MsMs 2909076 Specdb::MsMs 2909077 Specdb::MsMs 2909078 Specdb::MsMs 2953845 Specdb::MsMs 2953846 Specdb::MsMs 2953847 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 0.25 +/- 0.01 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 0.320 +/- 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 0.375 +/- 0.001 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 0.226 +/- 0.004 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 24766933 52923067 89372 FDB025461 C00157 PHOSPHATIDYLCHOLINE A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)