1.0 2016-10-03 17:23:56 UTC 2020-06-04 19:47:59 UTC BMDB0008546 BMDB08546 PC(22:0/22:1(13Z)) PC(22:0/22:1(13Z)), also known as PC(22:0/22:1) or gpcho(44:1), 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(22:0/22:1(13Z)) is considered to be a glycerophosphocholine lipid molecule. PC(22:0/22:1(13Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(22:0/22:1(13Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(22:0/22:1(13Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(22:0/22:1(13Z)); which is mediated by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(22:0/22:1(13Z)) can be biosynthesized from CDP-choline and DG(22:0/22:1(13Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(22:0/22:1(13Z)) and L-serine can be converted into choline and PS(22:0/22:1(13Z)); which is catalyzed by the enzyme phosphatidylserine synthase. In cattle, PC(22:0/22:1(13Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(22:0/22:1(13Z)) pathway and phosphatidylethanolamine biosynthesis pe(22:0/22:1(13Z)) pathway. 1-Behenoyl-2-erucoyl-sn-glycero-3-phosphocholine PC(22:0/22:1) GPCho(44:1) Phosphatidylcholine(22:0/22:1) PC(44:1) Lecithin GPCho(22:0/22:1) 1-Docosanoyl-2-(13Z-docosenoyl)-sn-glycero-3-phosphocholine Phosphatidylcholine(44:1) PC(22:0/22:1(13Z)) C52H102NO8P 900.3419 899.734305757 (2-{[(2R)-2-[(13Z)-docos-13-enoyloxy]-3-(docosanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium lecithin CCCCCCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCC\C=C/CCCCCCCC InChI=1S/C52H102NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-42-44-51(54)58-48-50(49-60-62(56,57)59-47-46-53(3,4)5)61-52(55)45-43-41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h21,23,50H,6-20,22,24-49H2,1-5H3/b23-21-/t50-/m1/s1 LTXUEXPDKWPLQA-ZMGYLBOHSA-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 6.83 ALOGPS logs -7.74 ALOGPS logp 13.09 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac (2-{[(2R)-2-[(13Z)-docos-13-enoyloxy]-3-(docosanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium ChemAxon average_mass 900.3419 ChemAxon mono_mass 899.734305757 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCC\C=C/CCCCCCCC ChemAxon formula C52H102NO8P ChemAxon inchi InChI=1S/C52H102NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-42-44-51(54)58-48-50(49-60-62(56,57)59-47-46-53(3,4)5)61-52(55)45-43-41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h21,23,50H,6-20,22,24-49H2,1-5H3/b23-21-/t50-/m1/s1 ChemAxon inchikey LTXUEXPDKWPLQA-ZMGYLBOHSA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 272.19 ChemAxon polarizability 115.3 ChemAxon rotatable_bond_count 51 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(22:0/22:1(13Z)) SMP0080821 Phosphatidylethanolamine Biosynthesis PE(22:0/22:1(13Z)) SMP0082630 Specdb::MsMs 682093 Specdb::MsMs 682094 Specdb::MsMs 682095 Specdb::MsMs 2407229 Specdb::MsMs 2407230 Specdb::MsMs 2407231 Specdb::MsMs 2461942 Specdb::MsMs 2461943 Specdb::MsMs 2461944 Specdb::MsMs 2779708 Specdb::MsMs 2779709 Specdb::MsMs 2779710 Specdb::MsMs 2903079 Specdb::MsMs 2903080 Specdb::MsMs 2903081 Specdb::MsMs 2937388 Specdb::MsMs 2937389 Specdb::MsMs 2937390 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 1.39 +/- 0.02 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 2.25 +/- 0.03 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 3.6 +/- 0.1 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 1.16 +/- 0.04 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 24779119 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)