1.0 2016-10-03 17:23:17 UTC 2020-05-11 18:46:53 UTC BMDB0008515 BMDB08515 PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)), also known as Pc(20:5(5z,8z,11z,14z,17z)/22:4(7z,10z,13z,16z)) or pc(20:5(5z,8z,11z,14z,17z)/22:4(7z,10z,13z,16z)), 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(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) is considered to be a glycerophosphocholine lipid molecule. PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)); which is catalyzed by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) can be biosynthesized from CDP-choline and DG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) and L-serine can be converted into choline and PS(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)); which is catalyzed by the enzyme phosphatidylserine synthase. In cattle, PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) pathway and phosphatidylethanolamine biosynthesis pe(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) pathway. 1-Eicosapentaenoyl-2-adrenoyl-sn-glycero-3-phosphocholine Gpcho(20:5/22:4) Gpcho(20:5n3/22:4n6) Gpcho(20:5W3/22:4W6) Gpcho(42:9) Lecithin PC(20:5/22:4) PC(20:5n3/22:4n6) PC(20:5W3/22:4W6) PC(42:9) Phosphatidylcholine(20:5/22:4) Phosphatidylcholine(20:5n3/22:4n6) Phosphatidylcholine(20:5W3/22:4W6) Phosphatidylcholine(42:9) 1-(5Z,8Z,11Z,14Z,17Z-Eicosapentaenoyl)-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycero-3-phosphocholine PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) C50H82NO8P 856.1617 855.577805117 (2-{[(2R)-2-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium lecithin CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(=O)O[C@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)COP([O-])(=O)OCC[N+](C)(C)C InChI=1S/C50H82NO8P/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/h9,11,14-17,20-23,25,27-28,30-31,33-34,36,48H,6-8,10,12-13,18-19,24,26,29,32,35,37-47H2,1-5H3/b11-9-,16-14-,17-15-,22-20-,23-21-,27-25-,30-28-,33-31-,36-34-/t48-/m1/s1 QXFLCSRGTJSRSB-FHXFQLHXSA-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 5.74 ALOGPS logs -7.41 ALOGPS logp 9.3 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac (2-{[(2R)-2-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium ChemAxon average_mass 856.1617 ChemAxon mono_mass 855.577805117 ChemAxon smiles CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(=O)O[C@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)COP([O-])(=O)OCC[N+](C)(C)C ChemAxon formula C50H82NO8P ChemAxon inchi InChI=1S/C50H82NO8P/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/h9,11,14-17,20-23,25,27-28,30-31,33-34,36,48H,6-8,10,12-13,18-19,24,26,29,32,35,37-47H2,1-5H3/b11-9-,16-14-,17-15-,22-20-,23-21-,27-25-,30-28-,33-31-,36-34-/t48-/m1/s1 ChemAxon inchikey QXFLCSRGTJSRSB-FHXFQLHXSA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 271.92 ChemAxon polarizability 99.41 ChemAxon rotatable_bond_count 41 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(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) SMP0080814 Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) SMP0082623 Specdb::CMs 215068 Specdb::MsMs 626299 Specdb::MsMs 626300 Specdb::MsMs 626301 Specdb::MsMs 2297255 Specdb::MsMs 2297256 Specdb::MsMs 2297257 Specdb::MsMs 2483314 Specdb::MsMs 2483315 Specdb::MsMs 2483316 Specdb::MsMs 2637790 Specdb::MsMs 2637791 Specdb::MsMs 2637792 Specdb::MsMs 2755564 Specdb::MsMs 2755565 Specdb::MsMs 2755566 Specdb::MsMs 2803513 Specdb::MsMs 2803514 Specdb::MsMs 2803515 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 24767176 52923385 FDB025705 C00157