1.0 2016-10-03 17:19:13 UTC 2020-06-04 19:11:05 UTC BMDB0008348 BMDB08348 PC(20:2(11Z,14Z)/22:0) PC(20:2(11Z,14Z)/22:0), also known as pc(20:2(11z,14z)/22:0) or PC(20:2/22:0), 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(20:2(11Z,14Z)/22:0) is considered to be a glycerophosphocholine lipid molecule. PC(20:2(11Z,14Z)/22:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(20:2(11Z,14Z)/22:0) exists in all eukaryotes, ranging from yeast to humans. PC(20:2(11Z,14Z)/22:0) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(20:2(11Z,14Z)/22:0) can be biosynthesized from S-adenosylmethionine and pe-nme2(20:2(11Z,14Z)/22:0) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(20:2(11Z,14Z)/22:0) can be biosynthesized from CDP-choline and DG(20:2(11Z,14Z)/22:0/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PC(20:2(11Z,14Z)/22:0) and L-serine can be converted into choline and PS(20:2(11Z,14Z)/22:0); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(20:2(11Z,14Z)/22:0) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(20:2(11Z,14Z)/22:0) pathway and phosphatidylethanolamine biosynthesis pe(20:2(11Z,14Z)/22:0) pathway. 1-eicosadienoyl-2-behenoyl-sn-glycero-3-phosphocholine Phosphatidylcholine(42:2) PC(20:2/22:0) Lecithin GPCho(42:2) PC(20:2(11Z,14Z)/22:0) PC(42:2) Phosphatidylcholine(20:2/22:0) 1-(11Z,14Z-eicosadienoyl)-2-docosanoyl-sn-glycero-3-phosphocholine GPCho(20:2/22:0) C50H96NO8P 870.2729 869.687355565 (2-{[(2R)-2-(docosanoyloxy)-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium lecithin CCCCCCCCCCCCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC)COP([O-])(=O)OCC[N+](C)(C)C InChI=1S/C50H96NO8P/c1-6-8-10-12-14-16-18-20-22-24-25-27-29-31-33-35-37-39-41-43-50(53)59-48(47-58-60(54,55)57-45-44-51(3,4)5)46-56-49(52)42-40-38-36-34-32-30-28-26-23-21-19-17-15-13-11-9-7-2/h15,17,21,23,48H,6-14,16,18-20,22,24-47H2,1-5H3/b17-15-,23-21-/t48-/m1/s1 GGBMXULOGOMRJY-HHITYQTISA-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 6.63 ALOGPS logs -7.65 ALOGPS logp 11.84 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac (2-{[(2R)-2-(docosanoyloxy)-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium ChemAxon average_mass 870.2729 ChemAxon mono_mass 869.687355565 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC)COP([O-])(=O)OCC[N+](C)(C)C ChemAxon formula C50H96NO8P ChemAxon inchi InChI=1S/C50H96NO8P/c1-6-8-10-12-14-16-18-20-22-24-25-27-29-31-33-35-37-39-41-43-50(53)59-48(47-58-60(54,55)57-45-44-51(3,4)5)46-56-49(52)42-40-38-36-34-32-30-28-26-23-21-19-17-15-13-11-9-7-2/h15,17,21,23,48H,6-14,16,18-20,22,24-47H2,1-5H3/b17-15-,23-21-/t48-/m1/s1 ChemAxon inchikey GGBMXULOGOMRJY-HHITYQTISA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 264.11 ChemAxon polarizability 109.66 ChemAxon rotatable_bond_count 48 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 Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:0) SMP0080751 Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:0) SMP0082559 Specdb::MsMs 309184 Specdb::MsMs 309185 Specdb::MsMs 309186 Specdb::MsMs 353539 Specdb::MsMs 353540 Specdb::MsMs 353541 Specdb::MsMs 2271732 Specdb::MsMs 2271733 Specdb::MsMs 2271734 Specdb::MsMs 2287285 Specdb::MsMs 2287286 Specdb::MsMs 2287287 Specdb::MsMs 2366446 Specdb::MsMs 2366447 Specdb::MsMs 2366448 Specdb::MsMs 3004467 Specdb::MsMs 3004468 Specdb::MsMs 3004469 Specdb::MsMs 3067772 Specdb::MsMs 3067773 Specdb::MsMs 3067774 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 Ruminal Fluid 0.007 +/- 0.002 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. 24767009 52923201