1.0 2016-10-03 18:40:00 UTC 2020-06-04 19:37:30 UTC BMDB0013422 BMDB13422 PC(o-18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) PC(O-18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), also known as phosphatidylcholine(18:0/22:6) or gpcho(18:0/22:6), 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-18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is considered to be a glycerophosphocholine lipid molecule. PC(O-18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 1-Stearyl-2-docosahexaenoyl-sn-glycero-3-phosphocholine Gpcho(18:0/22:6) Gpcho(18:0/22:6n3) Gpcho(18:0/22:6W3) Gpcho(40:6) Lecithin PC Ae C40:6 PC(18:0/22:6) PC(18:0/22:6n3) PC(18:0/22:6W3) PC(40:6) PC(O-40:6) Phosphatidylcholine(18:0/22:6) Phosphatidylcholine(18:0/22:6n3) Phosphatidylcholine(18:0/22:6W3) Phosphatidylcholine(40:6) 1-Octadecanyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine PC(o-18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) C48H86NO7P 820.1727 819.614190623 (2-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium (2-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium CCCCCCCCCCCCCCCCCCOC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C48H86NO7P/c1-6-8-10-12-14-16-18-20-22-24-25-26-27-29-31-33-35-37-39-41-48(50)56-47(46-55-57(51,52)54-44-42-49(3,4)5)45-53-43-40-38-36-34-32-30-28-23-21-19-17-15-13-11-9-7-2/h8,10,14,16,20,22,25-26,29,31,35,37,47H,6-7,9,11-13,15,17-19,21,23-24,27-28,30,32-34,36,38-46H2,1-5H3/b10-8-,16-14-,22-20-,26-25-,31-29-,37-35-/t47-/m1/s1 QBZALASVZLFAHF-KYPHJRDXSA-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 2-acyl-1-alkyl-sn-glycero-3-phosphocholine phosphatidylcholine O-40:6 Solid logp 6.64 ALOGPS logs -7.38 ALOGPS logp 9.88 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -4.1 ChemAxon iupac (2-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium ChemAxon average_mass 820.1727 ChemAxon mono_mass 819.614190623 ChemAxon smiles CCCCCCCCCCCCCCCCCCOC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC ChemAxon formula C48H86NO7P ChemAxon inchi InChI=1S/C48H86NO7P/c1-6-8-10-12-14-16-18-20-22-24-25-26-27-29-31-33-35-37-39-41-48(50)56-47(46-55-57(51,52)54-44-42-49(3,4)5)45-53-43-40-38-36-34-32-30-28-23-21-19-17-15-13-11-9-7-2/h8,10,14,16,20,22,25-26,29,31,35,37,47H,6-7,9,11-13,15,17-19,21,23-24,27-28,30,32-34,36,38-46H2,1-5H3/b10-8-,16-14-,22-20-,26-25-,31-29-,37-35-/t47-/m1/s1 ChemAxon inchikey QBZALASVZLFAHF-KYPHJRDXSA-N ChemAxon polar_surface_area 94.12 ChemAxon refractivity 259.62 ChemAxon polarizability 99.54 ChemAxon rotatable_bond_count 42 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 301075 Specdb::MsMs 301076 Specdb::MsMs 301077 Specdb::MsMs 343513 Specdb::MsMs 343514 Specdb::MsMs 343515 Specdb::MsMs 2532165 Specdb::MsMs 2532166 Specdb::MsMs 2532167 Specdb::MsMs 2680638 Specdb::MsMs 2680639 Specdb::MsMs 2680640 Specdb::MsMs 3025587 Specdb::MsMs 3025588 Specdb::MsMs 3025589 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 0.46 +/- 0.11 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 Blood Detected by electrospray ionization tandem mass spectrometry with the Biocrates AbsoluteIDQ in male Charolais and Holstein cows. Weikard R, Altmaier E, Suhre K, Weinberger KM, Hammon HM, Albrecht E, Setoguchi K, Takasuga A, Kuhn C: Metabolomic profiles indicate distinct physiological pathways affected by two loci with major divergent effect on Bos taurus growth and lipid deposition. Physiol Genomics. 2010 Oct;42A(2):79-88. doi: 10.1152/physiolgenomics.00120.2010. Epub 2010 Jul 20. 20647382 Liver 2 +/- 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 Longissimus Thoracis Muscle 0.44 +/- 0.12 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 0.043 +/- 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 0.042 +/- 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 Ruminal Fluid 0.04 +/- 0.01 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 Semimembranosus Muscle 0.56 +/- 0.14 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 0.6 +/- 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 FDB029422 24779341 24822905 86252 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)