1.0 2016-10-03 18:40:42 UTC 2020-06-04 19:17:10 UTC BMDB0013440 BMDB13440 PC(o-20:0/18:3(9Z,12Z,15Z)) PC(O-20:0/18:3(9Z,12Z,15Z)), also known as phosphatidylcholine(20:0/18:3) or gpcho(20:0/18:3), belongs to the class of organic compounds known as 1-alkyl,2-acylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position. Thus, PC(O-20:0/18:3(9Z,12Z,15Z)) is considered to be a glycerophosphocholine lipid molecule. PC(O-20:0/18:3(9Z,12Z,15Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 1-Arachidyl-2-a-linolenoyl-sn-glycero-3-phosphocholine 1-Arachidyl-2-alpha-linolenoyl-sn-glycero-3-phosphocholine Gpcho(20:0/18:3) Gpcho(20:0/18:3n3) Gpcho(20:0/18:3W3) Gpcho(38:3) Lecithin PC Ae C38:3 PC(20:0/18:3) PC(20:0/18:3n3) PC(20:0/18:3W3) PC(38:3) PC(O-38:3) Phosphatidylcholine(20:0/18:3) Phosphatidylcholine(20:0/18:3n3) Phosphatidylcholine(20:0/18:3W3) Phosphatidylcholine(38:3) 1-Eicosanyl-2-(9Z,12Z,15Z-octadeatrienoyl)-sn-glycero-3-phosphocholine PC(o-20:0/18:3(9Z,12Z,15Z)) C46H88NO7P 798.1672 797.629840687 (2-{[(2R)-3-(icosyloxy)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium (2-{[(2R)-3-(icosyloxy)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium CCCCCCCCCCCCCCCCCCCCOC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC InChI=1S/C46H88NO7P/c1-6-8-10-12-14-16-18-20-22-23-24-26-28-30-32-34-36-38-41-51-43-45(44-53-55(49,50)52-42-40-47(3,4)5)54-46(48)39-37-35-33-31-29-27-25-21-19-17-15-13-11-9-7-2/h9,11,15,17,21,25,45H,6-8,10,12-14,16,18-20,22-24,26-44H2,1-5H3/b11-9-,17-15-,25-21-/t45-/m1/s1 APWUUZRAVVATRC-GBRUYZQDSA-N belongs to the class of organic compounds known as 1-alkyl,2-acylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position. Organic compounds Lipids and lipid-like molecules Glycerophospholipids Glycerophosphocholines 1-alkyl,2-acylglycero-3-phosphocholines Amines Carbonyl compounds Carboxylic acid esters Dialkyl ethers Dialkyl phosphates Fatty acid esters Glycerol ethers Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Organic salts Organopnictogen compounds Phosphocholines Tetraalkylammonium salts 1-alkyl,2-acylglycero-3-phosphocholine Aliphatic acyclic compound Alkyl phosphate Amine Carbonyl group Carboxylic acid derivative Carboxylic acid ester Dialkyl ether Dialkyl phosphate Ether Fatty acid ester Fatty acyl Glycerol ether Hydrocarbon derivative Monocarboxylic acid or derivatives 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 1-alkyl,2-acylglycerophosphocholines Solid logp 6.42 ALOGPS logs -7.55 ALOGPS logp 10.08 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -4.1 ChemAxon iupac (2-{[(2R)-3-(icosyloxy)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium ChemAxon average_mass 798.1672 ChemAxon mono_mass 797.629840687 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCOC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC ChemAxon formula C46H88NO7P ChemAxon inchi InChI=1S/C46H88NO7P/c1-6-8-10-12-14-16-18-20-22-23-24-26-28-30-32-34-36-38-41-51-43-45(44-53-55(49,50)52-42-40-47(3,4)5)54-46(48)39-37-35-33-31-29-27-25-21-19-17-15-13-11-9-7-2/h9,11,15,17,21,25,45H,6-8,10,12-14,16,18-20,22-24,26-44H2,1-5H3/b11-9-,17-15-,25-21-/t45-/m1/s1 ChemAxon inchikey APWUUZRAVVATRC-GBRUYZQDSA-N ChemAxon polar_surface_area 94.12 ChemAxon refractivity 247.07 ChemAxon polarizability 100.32 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 290662 Specdb::MsMs 290663 Specdb::MsMs 290664 Specdb::MsMs 330379 Specdb::MsMs 330380 Specdb::MsMs 330381 Specdb::MsMs 2672627 Specdb::MsMs 2672628 Specdb::MsMs 2672629 Specdb::MsMs 2846237 Specdb::MsMs 2846238 Specdb::MsMs 2846239 Specdb::MsMs 3032633 Specdb::MsMs 3032634 Specdb::MsMs 3032635 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 0.074 +/- 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 0.088 +/- 0.004 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 0.102 +/- 0.004 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 0.078 +/- 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 0.015 +/- 0.019 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. 52923836 FDB029440 89852 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)