1.0 2016-10-03 17:13:59 UTC 2020-06-04 19:40:03 UTC BMDB0008112 BMDB08112 PC(18:1(9Z)/20:3(5Z,8Z,11Z)) PC(18:1(9Z)/20:3(5Z,8Z,11Z)), also known as pc(18:1(9z)/20:3(5z,8z,11z)) or pc(18:1(9z)/20:3(5z,8z,11z)), 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(18:1(9Z)/20:3(5Z,8Z,11Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:1(9Z)/20:3(5Z,8Z,11Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:1(9Z)/20:3(5Z,8Z,11Z)) exists in all eukaryotes, ranging from yeast to humans. PC(18:1(9Z)/20:3(5Z,8Z,11Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:1(9Z)/20:3(5Z,8Z,11Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:1(9Z)/20:3(5Z,8Z,11Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:1(9Z)/20:3(5Z,8Z,11Z)) can be biosynthesized from CDP-choline and DG(18:1(9Z)/20:3(5Z,8Z,11Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:1(9Z)/20:3(5Z,8Z,11Z)) and L-serine can be converted into choline and PS(18:1(9Z)/20:3(5Z,8Z,11Z)); which is catalyzed by the enzyme phosphatidylserine synthase. In cattle, PC(18:1(9Z)/20:3(5Z,8Z,11Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:1(9Z)/20:3(5Z,8Z,11Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:1(9Z)/20:3(5Z,8Z,11Z)) pathway. 1-Oleoyl-2-meadoyl-sn-glycero-3-phosphocholine GPCho(18:1/20:3) GPCho(18:1n9/20:3n9) GPCho(18:1W9/20:3W9) PC(18:1n9/20:3n9) Phosphatidylcholine(18:1n9/20:3n9) Phosphatidylcholine(18:1/20:3) PC(38:4) GPCho(38:4) Phosphatidylcholine(38:4) PC(18:1/20:3) PC(18:1(9Z)/20:3(5Z,8Z,11Z)) Lecithin 1-(9Z-octadecenoyl)-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycero-3-phosphocholine C46H84NO8P 810.1348 809.593455181 (2-{[(2R)-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium lecithin CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC InChI=1S/C46H84NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h20-22,24-25,27,31,33,44H,6-19,23,26,28-30,32,34-43H2,1-5H3/b22-20-,24-21-,27-25-,33-31-/t44-/m1/s1 APIPSPZJMLSCBO-NRTPYZNRSA-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 phosphatidylcholine 38:4 Solid logp 6.04 ALOGPS logs -7.48 ALOGPS logp 9.33 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac (2-{[(2R)-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium ChemAxon average_mass 810.1348 ChemAxon mono_mass 809.593455181 ChemAxon smiles CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC ChemAxon formula C46H84NO8P ChemAxon inchi InChI=1S/C46H84NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h20-22,24-25,27,31,33,44H,6-19,23,26,28-30,32,34-43H2,1-5H3/b22-20-,24-21-,27-25-,33-31-/t44-/m1/s1 ChemAxon inchikey APIPSPZJMLSCBO-NRTPYZNRSA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 247.94 ChemAxon polarizability 98.78 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 Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:3(5Z,8Z,11Z)) SMP0080620 Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:3(5Z,8Z,11Z)) SMP0082424 Specdb::MsMs 305668 Specdb::MsMs 305669 Specdb::MsMs 305670 Specdb::MsMs 349123 Specdb::MsMs 349124 Specdb::MsMs 349125 Specdb::MsMs 2508241 Specdb::MsMs 2508242 Specdb::MsMs 2508243 Specdb::MsMs 2577666 Specdb::MsMs 2577667 Specdb::MsMs 2577668 Specdb::MsMs 2820627 Specdb::MsMs 2820628 Specdb::MsMs 2820629 Specdb::MsMs 2822285 Specdb::MsMs 2822286 Specdb::MsMs 2822287 Specdb::MsMs 2858429 Specdb::MsMs 2858430 Specdb::MsMs 2858431 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 0.033 +/- 0.008 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. FDB025302 24766774 24778947 86178