1.0 2016-09-30 23:49:50 UTC 2020-06-04 19:13:49 UTC BMDB0008054 BMDB08054 PC(18:0/22:4(7Z,10Z,13Z,16Z)) PC(18:0/22:4(7Z,10Z,13Z,16Z)), also known as phosphatidylcholine(18:0/22:4) or gpcho(18:0/22:4), 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(18:0/22:4(7Z,10Z,13Z,16Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:0/22:4(7Z,10Z,13Z,16Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:0/22:4(7Z,10Z,13Z,16Z)) exists in all eukaryotes, ranging from yeast to humans. PC(18:0/22:4(7Z,10Z,13Z,16Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:0/22:4(7Z,10Z,13Z,16Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:0/22:4(7Z,10Z,13Z,16Z)) through the action of the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:0/22:4(7Z,10Z,13Z,16Z)) can be biosynthesized from CDP-choline and DG(18:0/22:4(7Z,10Z,13Z,16Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:0/22:4(7Z,10Z,13Z,16Z)) and L-serine can be converted into choline and PS(18:0/22:4(7Z,10Z,13Z,16Z)) through the action of the enzyme phosphatidylserine synthase. In cattle, PC(18:0/22:4(7Z,10Z,13Z,16Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:0/22:4(7Z,10Z,13Z,16Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:0/22:4(7Z,10Z,13Z,16Z)) pathway. 1-Stearoyl-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycero-3-phosphocholine 1-Stearoyl-2-adrenoyl-sn-glycero-3-phosphocholine GPCho(18:0/22:4) GPCho(18:0/22:4n6) GPCho(18:0/22:4W6) PC(18:0/22:4) PC(18:0/22:4n6) PC(18:0/22:4W6) Phosphatidylcholine(18:0/22:4) Phosphatidylcholine(18:0/22:4n6) Phosphatidylcholine(18:0/22:4W6) Phosphatidylcholine(40:4) Lecithin GPCho(40:4) PC(18:0/22:4(7Z,10Z,13Z,16Z)) 1-octadecanoyl-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycero-3-phosphocholine PC(40:4) C48H88NO8P 838.188 837.624755309 (2-{[(2R)-2-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-3-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium lecithin CCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC InChI=1S/C48H88NO8P/c1-6-8-10-12-14-16-18-20-22-23-24-25-27-29-31-33-35-37-39-41-48(51)57-46(45-56-58(52,53)55-43-42-49(3,4)5)44-54-47(50)40-38-36-34-32-30-28-26-21-19-17-15-13-11-9-7-2/h14,16,20,22,24-25,29,31,46H,6-13,15,17-19,21,23,26-28,30,32-45H2,1-5H3/b16-14-,22-20-,25-24-,31-29-/t46-/m1/s1 AXZGUCXCTZMPTR-UVGACIQRSA-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 40:4 Solid logp 6.33 ALOGPS logs -7.52 ALOGPS logp 10.22 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-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium ChemAxon average_mass 838.188 ChemAxon mono_mass 837.624755309 ChemAxon smiles CCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC ChemAxon formula C48H88NO8P ChemAxon inchi InChI=1S/C48H88NO8P/c1-6-8-10-12-14-16-18-20-22-23-24-25-27-29-31-33-35-37-39-41-48(51)57-46(45-56-58(52,53)55-43-42-49(3,4)5)44-54-47(50)40-38-36-34-32-30-28-26-21-19-17-15-13-11-9-7-2/h14,16,20,22,24-25,29,31,46H,6-13,15,17-19,21,23,26-28,30,32-45H2,1-5H3/b16-14-,22-20-,25-24-,31-29-/t46-/m1/s1 ChemAxon inchikey AXZGUCXCTZMPTR-UVGACIQRSA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 257.14 ChemAxon polarizability 101.98 ChemAxon rotatable_bond_count 44 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(18:0/22:4(7Z,10Z,13Z,16Z)) SMP0080583 Phosphatidylethanolamine Biosynthesis PE(18:0/22:4(7Z,10Z,13Z,16Z)) SMP0082386 Specdb::CMs 246897 Specdb::MsMs 309358 Specdb::MsMs 309359 Specdb::MsMs 309360 Specdb::MsMs 353773 Specdb::MsMs 353774 Specdb::MsMs 353775 Specdb::MsMs 2380260 Specdb::MsMs 2380261 Specdb::MsMs 2380262 Specdb::MsMs 2435026 Specdb::MsMs 2435027 Specdb::MsMs 2435028 Specdb::MsMs 2839815 Specdb::MsMs 2839816 Specdb::MsMs 2839817 Specdb::MsMs 2869023 Specdb::MsMs 2869024 Specdb::MsMs 2869025 Specdb::MsMs 2910401 Specdb::MsMs 2910402 Specdb::MsMs 2910403 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 0.044 +/- 0.001 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 0.056 +/- 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 24766718 84565 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)