1.0 2016-09-30 23:48:25 UTC 2020-06-04 19:27:16 UTC BMDB0007984 BMDB07984 PC(16:0/20:5(5Z,8Z,11Z,14Z,17Z)) PC(16:0/20:5(5Z,8Z,11Z,14Z,17Z)), also known as phosphatidylcholine(16:0/20:5) or PC(16:0/20:5), 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(16:0/20:5(5Z,8Z,11Z,14Z,17Z)) is considered to be a glycerophosphocholine lipid molecule. PC(16:0/20:5(5Z,8Z,11Z,14Z,17Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:0/20:5(5Z,8Z,11Z,14Z,17Z)) exists in all eukaryotes, ranging from yeast to humans. PC(16:0/20:5(5Z,8Z,11Z,14Z,17Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(16:0/20:5(5Z,8Z,11Z,14Z,17Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(16:0/20:5(5Z,8Z,11Z,14Z,17Z)) through the action of the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(16:0/20:5(5Z,8Z,11Z,14Z,17Z)) can be biosynthesized from CDP-choline and DG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PC(16:0/20:5(5Z,8Z,11Z,14Z,17Z)) and L-serine can be converted into choline and PS(16:0/20:5(5Z,8Z,11Z,14Z,17Z)); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(16:0/20:5(5Z,8Z,11Z,14Z,17Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(16:0/20:5(5Z,8Z,11Z,14Z,17Z)) pathway and phosphatidylethanolamine biosynthesis pe(16:0/20:5(5Z,8Z,11Z,14Z,17Z)) pathway. 1-Hexadecanoyl-2-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-phosphocholine 1-Hexadecanoyl-2-[(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl]-sn-glycero-3-phosphocholine 1-Palmitoyl-2-eicosapentaenoyl-GPC 1-Palmitoyl-2-eicosapentaenoyl-GPC (16:0/20:5) 1-Palmitoyl-2-eicosapentaenoyl-sn-glycero-3-phosphocholine GPC(16:0/20:5) GPCho(16:0/20:5) GPCho(16:0/20:5n3) GPCho(16:0/20:5W3) PC(16:0/20:5) PC(16:0/20:5n3) PC(16:0/20:5W3) Phosphatidylcholine(16:0/20:5) Phosphatidylcholine(16:0/20:5n3) Phosphatidylcholine(16:0/20:5W3) Gpcho(36:5) Lecithin PC Aa C36:5 PC(36:5) Phosphatidylcholine(36:5) PC(16:0/20:5(5Z,8Z,11Z,14Z,17Z)) C44H78NO8P 780.0658 779.546504989 (2-{[(2R)-3-(hexadecanoyloxy)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium lecithin CCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C44H78NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-25-27-29-31-33-35-37-44(47)53-42(41-52-54(48,49)51-39-38-45(3,4)5)40-50-43(46)36-34-32-30-28-26-24-19-17-15-13-11-9-7-2/h8,10,14,16,20-21,23,25,29,31,42H,6-7,9,11-13,15,17-19,22,24,26-28,30,32-41H2,1-5H3/b10-8-,16-14-,21-20-,25-23-,31-29-/t42-/m1/s1 KLTHQSWIRFFBRI-CPFPVJFHSA-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 36:5 Solid logp 5.61 ALOGPS logs -7.44 ALOGPS logp 8.08 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac (2-{[(2R)-3-(hexadecanoyloxy)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium ChemAxon average_mass 780.0658 ChemAxon mono_mass 779.546504989 ChemAxon smiles CCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC ChemAxon formula C44H78NO8P ChemAxon inchi InChI=1S/C44H78NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-25-27-29-31-33-35-37-44(47)53-42(41-52-54(48,49)51-39-38-45(3,4)5)40-50-43(46)36-34-32-30-28-26-24-19-17-15-13-11-9-7-2/h8,10,14,16,20-21,23,25,29,31,42H,6-7,9,11-13,15,17-19,22,24,26-28,30,32-41H2,1-5H3/b10-8-,16-14-,21-20-,25-23-,31-29-/t42-/m1/s1 ChemAxon inchikey KLTHQSWIRFFBRI-CPFPVJFHSA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 239.85 ChemAxon polarizability 92.94 ChemAxon rotatable_bond_count 39 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(16:0/20:5(5Z,8Z,11Z,14Z,17Z)) SMP0080530 Phosphatidylethanolamine Biosynthesis PE(16:0/20:5(5Z,8Z,11Z,14Z,17Z)) SMP0082333 Specdb::MsMs 301177 Specdb::MsMs 301178 Specdb::MsMs 301179 Specdb::MsMs 343636 Specdb::MsMs 343637 Specdb::MsMs 343638 Specdb::MsMs 2299551 Specdb::MsMs 2299552 Specdb::MsMs 2299553 Specdb::MsMs 2308470 Specdb::MsMs 2308471 Specdb::MsMs 2308472 Specdb::MsMs 2346872 Specdb::MsMs 2346873 Specdb::MsMs 2346874 Specdb::MsMs 2639815 Specdb::MsMs 2639816 Specdb::MsMs 2639817 Specdb::MsMs 3059062 Specdb::MsMs 3059063 Specdb::MsMs 3059064 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 Milk 0.23 +/- 0.01 uM Commercial 1% 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 0.280 +/- 0.003 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 0.349 +/- 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 0.200 +/- 0.002 uM Commercial skim 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 0.018 +/- 0.019 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. 24766654 24778723 86137 FDB025175 C00157 PHOSPHATIDYLCHOLINE A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)