1.0 2016-10-03 17:20:27 UTC 2020-06-04 19:25:03 UTC BMDB0008396 BMDB08396 PC(20:3(8Z,11Z,14Z)/15:0) PC(20:3(8Z,11Z,14Z)/15:0), also known as gpcho(35:3) or lecithin, 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(20:3(8Z,11Z,14Z)/15:0) is considered to be a glycerophosphocholine lipid molecule. PC(20:3(8Z,11Z,14Z)/15:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 1-homo-g-linolenoyl-2-pentadecanoyl-sn-glycero-3-phosphocholine PC(20:3(8Z,11Z,14Z)/15:0) GPCho(35:3) Lecithin PC(35:3) GPCho(20:3/15:0) Phosphatidylcholine(35:3) PC(20:3/15:0) 1-(8Z,11Z,14Z-eicosatrienoyl)-2-pentadecanoyl-sn-glycero-3-phosphocholine Phosphatidylcholine(20:3/15:0) C43H80NO8P 770.071 769.562155053 (2-{[(2R)-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-2-(pentadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium lecithin CCCCCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC)COP([O-])(=O)OCC[N+](C)(C)C InChI=1S/C43H80NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-24-26-27-29-31-33-35-42(45)49-39-41(40-51-53(47,48)50-38-37-44(3,4)5)52-43(46)36-34-32-30-28-25-19-17-15-13-11-9-7-2/h14,16,20-21,23-24,41H,6-13,15,17-19,22,25-40H2,1-5H3/b16-14-,21-20-,24-23-/t41-/m1/s1 PBYSSMVZTSQJLK-XWIBIVISSA-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 5.60 ALOGPS logs -7.46 ALOGPS logp 8.36 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac (2-{[(2R)-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-2-(pentadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium ChemAxon average_mass 770.071 ChemAxon mono_mass 769.562155053 ChemAxon smiles CCCCCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC)COP([O-])(=O)OCC[N+](C)(C)C ChemAxon formula C43H80NO8P ChemAxon inchi InChI=1S/C43H80NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-24-26-27-29-31-33-35-42(45)49-39-41(40-51-53(47,48)50-38-37-44(3,4)5)52-43(46)36-34-32-30-28-25-19-17-15-13-11-9-7-2/h14,16,20-21,23-24,41H,6-13,15,17-19,22,25-40H2,1-5H3/b16-14-,21-20-,24-23-/t41-/m1/s1 ChemAxon inchikey PBYSSMVZTSQJLK-XWIBIVISSA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 233.02 ChemAxon polarizability 93.32 ChemAxon rotatable_bond_count 40 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 Specdb::MsMs 637444 Specdb::MsMs 637445 Specdb::MsMs 637446 Specdb::MsMs 2359892 Specdb::MsMs 2359893 Specdb::MsMs 2359894 Specdb::MsMs 2606137 Specdb::MsMs 2606138 Specdb::MsMs 2606139 Specdb::MsMs 2655524 Specdb::MsMs 2655525 Specdb::MsMs 2655526 Specdb::MsMs 2697519 Specdb::MsMs 2697520 Specdb::MsMs 2697521 Specdb::MsMs 3109731 Specdb::MsMs 3109732 Specdb::MsMs 3109733 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 0.10 +/- 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 0.18 +/- 0.01 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 0.29 +/- 0.01 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 0.067 +/- 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 24767056 52923217 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)