1.0 2016-09-30 23:49:11 UTC 2020-06-04 20:05:05 UTC BMDB0008022 BMDB08022 PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)), also known as pc(16:1(9z)/22:5(4z,7z,10z,13z,16z)) or PC(16:1/22:5), 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(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) is considered to be a glycerophosphocholine lipid molecule. PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) exists in all eukaryotes, ranging from yeast to humans. PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) through the action of the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) can be biosynthesized from CDP-choline and DG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) and L-serine can be converted into choline and PS(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) pathway and phosphatidylethanolamine biosynthesis pe(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) pathway. GPCho(38:6) PC(16:1/22:5) Phosphatidylcholine(16:1/22:5) Phosphatidylcholine(38:6) Lecithin GPCho(16:1/22:5) 1-Palmitoleoyl-2-osbondoyl-sn-glycero-3-phosphocholine 1-(9Z-Hexadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-sn-glycero-3-phosphocholine PC(38:6) PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) C46H80NO8P 806.1031 805.562155053 (2-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-3-[(9Z)-hexadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium (2-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-3-[(9Z)-hexadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium [H][C@@](COC(=O)CCCCCCC\C=C/CCCCCC)(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/CCCCC InChI=1S/C46H80NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-19-17-15-13-11-9-7-2/h14,16-17,19-21,23-24,27,29,33,35,44H,6-13,15,18,22,25-26,28,30-32,34,36-43H2,1-5H3/b16-14-,19-17-,21-20-,24-23-,29-27-,35-33-/t44-/m1/s1 WCODZEYPAWOVBI-UMQSOSPQSA-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 5.78 ALOGPS logs -7.45 ALOGPS logp 8.61 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac (2-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-3-[(9Z)-hexadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium ChemAxon average_mass 806.1031 ChemAxon mono_mass 805.562155053 ChemAxon smiles [H][C@@](COC(=O)CCCCCCC\C=C/CCCCCC)(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/CCCCC ChemAxon formula C46H80NO8P ChemAxon inchi InChI=1S/C46H80NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-19-17-15-13-11-9-7-2/h14,16-17,19-21,23-24,27,29,33,35,44H,6-13,15,18,22,25-26,28,30-32,34,36-43H2,1-5H3/b16-14-,19-17-,21-20-,24-23-,29-27-,35-33-/t44-/m1/s1 ChemAxon inchikey WCODZEYPAWOVBI-UMQSOSPQSA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 250.17 ChemAxon polarizability 95.4 ChemAxon rotatable_bond_count 40 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(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) SMP0080560 Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) SMP0082363 Specdb::MsMs 300313 Specdb::MsMs 300314 Specdb::MsMs 300315 Specdb::MsMs 342559 Specdb::MsMs 342560 Specdb::MsMs 342561 Specdb::MsMs 2620130 Specdb::MsMs 2620131 Specdb::MsMs 2620132 Specdb::MsMs 2704928 Specdb::MsMs 2704929 Specdb::MsMs 2704930 Specdb::MsMs 2720223 Specdb::MsMs 2720224 Specdb::MsMs 2720225 Specdb::MsMs 3004506 Specdb::MsMs 3004507 Specdb::MsMs 3004508 Specdb::MsMs 3082386 Specdb::MsMs 3082387 Specdb::MsMs 3082388 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 1 +/- 0.3 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 Liver 6 +/- 3 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 0.5 +/- 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 Ruminal Fluid 0.020 +/- 0.014 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. Ruminal Fluid 0.06 +/- 0.04 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 0.6 +/- 0.2 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 21 +/- 5 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 53478685 89657 FDB025213