1.0 2016-10-03 17:23:12 UTC 2020-05-11 18:46:50 UTC BMDB0008511 BMDB08511 PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)), also known as Pc(20:5(5z,8z,11z,14z,17z)/20:5(5z,8z,11z,14z,17z)) or pc(20:5(5z,8z,11z,14z,17z)/20:5(5z,8z,11z,14z,17z)), 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)/20:5(5Z,8Z,11Z,14Z,17Z)) is considered to be a glycerophosphocholine lipid molecule. PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) through the action of the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) can be biosynthesized from CDP-choline and DG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) and L-serine can be converted into choline and PS(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) through the action of the enzyme phosphatidylserine synthase. In cattle, PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) pathway and phosphatidylethanolamine biosynthesis pe(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) pathway. 1,2-Dieicosapentaenoyl-rac-glycero-3-phosphocholine Phosphatidylcholine(40:10) PC(40:10) GPCho(40:10) Lecithin PC(20:5/20:5) Phosphatidylcholine(20:5/20:5) 1,2-Di(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-rac-glycero-3-phosphocholine GPCho(20:5/20:5) 1,2-DEGP 1,2-Dieicosapentaenoyl-sn-glycero-3-phosphocholine PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) C48H76NO8P 826.0927 825.530854925 (2-{[(2R)-2,3-bis[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium lecithin CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(=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/C48H76NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-47(50)54-44-46(45-56-58(52,53)55-43-42-49(3,4)5)57-48(51)41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h8-11,14-17,20-23,26-29,32-35,46H,6-7,12-13,18-19,24-25,30-31,36-45H2,1-5H3/b10-8-,11-9-,16-14-,17-15-,22-20-,23-21-,28-26-,29-27-,34-32-,35-33-/t46-/m1/s1 WAIHGVAZVKEQGR-YWTDJUEZSA-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 5.29 ALOGPS logs -7.30 ALOGPS logp 8.05 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac (2-{[(2R)-2,3-bis[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium ChemAxon average_mass 826.0927 ChemAxon mono_mass 825.530854925 ChemAxon smiles CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(=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 C48H76NO8P ChemAxon inchi InChI=1S/C48H76NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-47(50)54-44-46(45-56-58(52,53)55-43-42-49(3,4)5)57-48(51)41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h8-11,14-17,20-23,26-29,32-35,46H,6-7,12-13,18-19,24-25,30-31,36-45H2,1-5H3/b10-8-,11-9-,16-14-,17-15-,22-20-,23-21-,28-26-,29-27-,34-32-,35-33-/t46-/m1/s1 ChemAxon inchikey WAIHGVAZVKEQGR-YWTDJUEZSA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 263.84 ChemAxon polarizability 94.28 ChemAxon rotatable_bond_count 38 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)/20:5(5Z,8Z,11Z,14Z,17Z)) SMP0080810 Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) SMP0082619 Specdb::MsMs 636214 Specdb::MsMs 636215 Specdb::MsMs 636216 Specdb::MsMs 2395494 Specdb::MsMs 2395495 Specdb::MsMs 2395496 Specdb::MsMs 2475173 Specdb::MsMs 2475174 Specdb::MsMs 2475175 Specdb::MsMs 2722140 Specdb::MsMs 2722141 Specdb::MsMs 2722142 Specdb::MsMs 2896020 Specdb::MsMs 2896021 Specdb::MsMs 2896022 Specdb::MsMs 2959707 Specdb::MsMs 2959708 Specdb::MsMs 2959709 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 52923375