1.0 2018-11-07 18:04:53 UTC 2020-06-04 19:13:20 UTC BMDB0063631 BMDB63631 PC(O-22:0/22:5(7Z,10Z,13Z,16Z,19Z)) PC(O-22:0/22:5(7Z,10Z,13Z,16Z,19Z)) is a phosphatidylchloline (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylcholines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(O-22:0/22:5(7Z,10Z,13Z,16Z,19Z)), in particular, consists of one docosanyl chain to the C-1 atom, and one 7Z,10Z,13Z,16Z,19Z-docosapentaenoyl to the C-2 atom. In E. coli, PCs can be found in the integral component of the cell outer membrane. They are hydrolyzed by Phospholipases to a 2-acylglycerophosphocholine and a carboxylate. PCs can also be synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. C52H96NO7P 878.314 877.692441433 (2-{[(2R)-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-3-(docosyloxy)propyl phosphono]oxy}ethyl)trimethylazanium (2-{[(2R)-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-3-(docosyloxy)propyl phosphono]oxy}ethyl)trimethylazanium [H][C@@](COCCCCCCCCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C52H96NO7P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-42-44-47-57-49-51(50-59-61(55,56)58-48-46-53(3,4)5)60-52(54)45-43-41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h9,11,15,17,21,23,27,29,33,35,51H,6-8,10,12-14,16,18-20,22,24-26,28,30-32,34,36-50H2,1-5H3/b11-9-,17-15-,23-21-,29-27-,35-33-/t51-/m1/s1 VNNPAAOAYXMMKU-JCWXPRBNSA-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 logp 7.17 ALOGPS logs -7.54 ALOGPS logp 12.02 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -4.1 ChemAxon iupac (2-{[(2R)-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-3-(docosyloxy)propyl phosphono]oxy}ethyl)trimethylazanium ChemAxon average_mass 878.314 ChemAxon mono_mass 877.692441433 ChemAxon smiles [H][C@@](COCCCCCCCCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC ChemAxon formula C52H96NO7P ChemAxon inchi InChI=1S/C52H96NO7P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-42-44-47-57-49-51(50-59-61(55,56)58-48-46-53(3,4)5)60-52(54)45-43-41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h9,11,15,17,21,23,27,29,33,35,51H,6-8,10,12-14,16,18-20,22,24-26,28,30-32,34,36-50H2,1-5H3/b11-9-,17-15-,23-21-,29-27-,35-33-/t51-/m1/s1 ChemAxon inchikey VNNPAAOAYXMMKU-JCWXPRBNSA-N ChemAxon polar_surface_area 94.12 ChemAxon refractivity 276.91 ChemAxon polarizability 110.18 ChemAxon rotatable_bond_count 47 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 1253704 Specdb::MsMs 1253705 Specdb::MsMs 1253706 Specdb::MsMs 1368922 Specdb::MsMs 1368923 Specdb::MsMs 1368924 Milk 0.063 +/- 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 0.048 +/- 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 Ruminal Fluid 0.022 +/- 0.004 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. 75320561 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)