1.0 2016-09-30 22:33:17 UTC 2020-06-04 20:44:40 UTC BMDB0000593 BMDB00593 PC(18:1(9Z)/18:1(9Z)) PC(18:1(9Z)/18:1(9Z)) , also known as dielaidinoyl lecithin or 1,2-DOCPC, 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. PC(18:1(9Z)/18:1(9Z)) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (R-(Z,Z))-(7-Oleoyl-4-oxido-10-oxo-3,5,9-trioxa-4-phosphaheptacos-18-enyl)trimethylammonium 4-oxide 1,2-Di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine 1,2-Dioleoyl-L-alpha-lecithin 1-(9Z)-Octadecenoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholine 1-C18:1(Omega-9)-2-C18:1(omega-9)-phosphatidylcholine Dioleoyl lecithin Dioleoyl phosphatidylcholine PC 18:1 PC(18:1(9Z)/18:1(9Z)) PC(18:1/18:1) Phosphatidylcholine 18:1 1,2-Dioleoyl-L-a-lecithin 1,2-Dioleoyl-L-α-lecithin 1,2-Di-(9Z)-octadecenoyl-sn-glycero-3-phosphocholine 1,2-Dioleoyl-sn-glycerol-3-ethylphosphocholine Dioleylphosphatidylcholine 1,2-Oleoylphosphatidylcholine, (L-alpha)-(R-(Z,Z))-isomer Dielaidoylphosphatidylcholine Dioleoylphosphatidylcholine 1,2-Dioleoylglycerophosphocholine 1,2-Oleoyl-sn-glycero-3-phosphocholine DOPC Dielaidinoyl lecithin 1,2-DOCPC 1,2-Dioleoyl glycerophosphocholine 1,2-Dioleoyl-sn-glycero-3-phosphocholine 1,2-Oleoylphosphatidylcholine 1,2-Dioleoyl-GPC 1,2-Dioleoyl-sn-glycero-phosphatidylcholine GPC(18:1(9Z)/18:1(9Z)) GPC(18:1/18:1) GPC(18:1n9/18:1n9) GPC(18:1w9/18:1w9) GPC(36:2) GPCho(18:1(9Z)/18:1(9Z)) GPCho(18:1/18:1) GPCho(18:1n9/18:1n9) GPCho(18:1w9/18:1w9) GPCho(36:2) PC(18:1n9/18:1n9) PC(18:1w9/18:1w9) PC(36:2) Phosphatidylcholine(18:1(9Z)/18:1(9Z)) Phosphatidylcholine(18:1/18:1) Phosphatidylcholine(18:1n9/18:1n9) Phosphatidylcholine(18:1w9/18:1w9) Phosphatidylcholine(36:2) 1,2-Dioleoyl-3-sn-phosphatidylcholine 1,2-Dioleoyl-sn-glycero-3-phosphochline 1,2-Dioleoyl-sn-glycero-3-phosphorylcholine 1,2-Dioleoyl-sn-phosphatidylcholine 1,2-Dioleoylphosphatidylcholine 1,2-Dioleyl-L-lecithin Dioleoyl L-alpha-lecithin Dioleoyl L-α-lecithin Dioleoyl-3-sn-phosphatidylcholine Dioleoyl-L-alpha-glycerophosphocholine Dioleoyl-L-alpha-glycerophosphorylcholine Dioleoyl-L-alpha-phosphatidylcholine Dioleoyl-L-α-glycerophosphocholine Dioleoyl-L-α-glycerophosphorylcholine Dioleoyl-L-α-phosphatidylcholine Dioleoyllecithin L-Dioleoyl lecithin L-Dioleoylphosphatidylcholine L-alpha-Di(cis-9-octadecanoyl) lecithin L-alpha-Dioleoyl phosphatidylcholine L-alpha-Dioleoyllecithin L-alpha-Dioleylphosphatidylcholine L-α-Di(cis-9-octadecanoyl) lecithin L-α-Dioleoyl phosphatidylcholine L-α-Dioleoyllecithin L-α-Dioleylphosphatidylcholine sn-3-Dioleoyllecithin 1,2-Dioleoylglycerol-3-phosphorylcholine 1,2-Dioleoylglyceryl-3-phosphorylcholine 1,2-Dioleoyllecithin Dioleoylglycerophosphocholine Dioleoylglycerophosphorylcholine Dioleoylglycerylphosphorylcholine Dioleyl lecithin Dioleyl phosphatidylcholine C44H84NO8P 786.1134 785.593455181 (2-{[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium (2-{[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium 4235-95-4 [H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC InChI=1S/C44H84NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h20-23,42H,6-19,24-41H2,1-5H3/b22-20-,23-21-/t42-/m1/s1 SNKAWJBJQDLSFF-NVKMUCNASA-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 36:2 Solid logp 5.78 ALOGPS logs -7.58 ALOGPS logp 9.17 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac (2-{[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium ChemAxon average_mass 786.1134 ChemAxon mono_mass 785.593455181 ChemAxon smiles [H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC ChemAxon formula C44H84NO8P ChemAxon inchi InChI=1S/C44H84NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h20-23,42H,6-19,24-41H2,1-5H3/b22-20-,23-21-/t42-/m1/s1 ChemAxon inchikey SNKAWJBJQDLSFF-NVKMUCNASA-N ChemAxon polar_surface_area 111.19 ChemAxon refractivity 236.5 ChemAxon polarizability 96.97 ChemAxon rotatable_bond_count 42 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 648751 Specdb::MsMs 648752 Specdb::MsMs 648753 Specdb::MsMs 2619281 Specdb::MsMs 2619282 Specdb::MsMs 2619283 Specdb::MsMs 2724503 Specdb::MsMs 2724504 Specdb::MsMs 2724505 Specdb::MsMs 2765318 Specdb::MsMs 2765319 Specdb::MsMs 2765320 Specdb::MsMs 2944387 Specdb::MsMs 2944388 Specdb::MsMs 2944389 Specdb::MsMs 3084721 Specdb::MsMs 3084722 Specdb::MsMs 3084723 Milk 5.82 +/- 0.04 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 7.0 +/- 0.2 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 9.5 +/- 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 5.48 +/- 0.03 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 Ruminal Fluid 0.263 uM By direct flow injection MS/MS. Daily cows fed barley grains (15% of diet dry matter) (n=8) Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7. 22959937 Ruminal Fluid 0.104 uM By direct flow injection MS/MS. Daily cows fed barley grains (30% of diet dry matter) (n=8) Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7. 22959937 Ruminal Fluid 0.019 uM By direct flow injection MS/MS. Daily cows fed barley grains (45% of diet dry matter) (n=8) Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7. 22959937 Ruminal Fluid 0.642 uM By direct flow injection MS/MS. No barley grains in diet (n=8) Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7. 22959937 Ruminal Fluid 0.564 +/- 0.381 uM Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Ruminal Fluid 0.501 +/- 0.341 uM Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Ruminal Fluid 0.531 +/- 0.436 uM Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Ruminal Fluid 0.601 +/- 0.735 uM Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. 8525772 10350317 74669 CPD-2181 Tokuyama, Satoru; Morisawa, Kazuya; Nakachi, Osamu; Nakano, Yoshiro; Miki, Tomoharu. Preparation of phosphatidylcholines. Jpn. Kokai Tokkyo Koho (1989), 6 pp. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) BMDBP00420 Phosphatidylethanolamine N-methyltransferase Q7YRH6 PEMT Enzyme BMDBP02841 Phosphatidylserine synthase 1 Q2KHY9 PTDSS1 Enzyme