1.0 2016-10-03 18:05:32 UTC 2020-06-04 20:09:23 UTC BMDB0010384 BMDB0062739 BMDB10384 BMDB62739 LysoPC(18:0/0:0) (2R)-2-Hydroxy-3-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate 1-O-Stearoyl-sn-glycero-3-phosphocholine 1-Octadecanoyl-sn-glycero-3-phosphocholine 1-Stearoyl-glycero-3-phosphocholine 1-Stearoylglycerophosphocholine (18:0) 1-Stearoylglycerophosphocholine(18:0) 18:0 LYSO-PC GPCho 18:0/0:0 GPCho(18:0/0:0) LPC 18:0/0:0 LPC(18:0) LPC(18:0/0:0) LysoPC 18:0/0:0 LysoPC(18:0) Lysophosphatidylcholine (18:0/0:0) Lysophosphatidylcholine(18:0) Lysophosphatidylcholine(18:0/0:0) PC 18:0/0:0 PC(18:0/0:0) (2R)-2-Hydroxy-3-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphoric acid LyPC(18:0) LyPC(18:0/0:0) LysoPC a C18:0 Stearoyl alpha-lysolecithin Stearoyllysophosphatidylcholine 1-Octadecyl-glycero-3-phosphocholine 1-Stearoyl-sn-glycero-3-phosphorylcholine Stearoyl L-alpha-lysolecithin 1-Stearoyl-2-hydroxy-sn-glycero-3-phosphocholine Stearoyl alpha-lysolecithin, (+-)-isomer Stearoyl alpha-lysolecithin, (R)-isomer 1-Octadecanoyl-glycero-3-phosphocholine 1-Octadecanoylglycerophosphocholine 1-Octadecylglycerophosphocholine 1-Stearoylglycerophosphocholine 1-O-Stearoyl-2-lyso-sn-glycero-3-phosphocholine 1-Octadecanoyl-3-glycerophosphorylcholine 1-Octadecanoyl-sn-glycerol-3-phosphorylcholine 1-Octadecanoyllysolecithin 1-Stearoyl-2-lysophosphatidylcholine 1-Stearoyl-3-glycerylphosphorylcholine 1-Stearoyl-GPC 1-Stearoyl-lysophosphatidylcholine 1-Stearoyl-sn-glycero-3-phosphocholine 1-Stearoyl-sn-glycerol-3-phosphatidylcholine 1-Stearoyl-sn-glycerol-3-phosphorylcholine 1-Stearoylglycero-3-phosphorylcholine 1-Stearoyllysophosphatidylcholine GPC(18:0) GPC(18:0/0:0) Lysophosphatidylcholine C18:0 Stearoyl L-α-lysolecithin Stearoyl lysolecithin Stearoyl lysophosphatidylcholine LysoPC(18:0/0:0) C26H54NO7P 523.6832 523.363789599 (2-{[(2R)-2-hydroxy-3-(octadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium (2-{[(2R)-2-hydroxy-3-(octadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium 19420-57-6 [H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C InChI=1S/C26H54NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)32-23-25(28)24-34-35(30,31)33-22-21-27(2,3)4/h25,28H,5-24H2,1-4H3/t25-/m1/s1 IHNKQIMGVNPMTC-RUZDIDTESA-N belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine. Organic compounds Lipids and lipid-like molecules Glycerophospholipids Glycerophosphocholines 1-acyl-sn-glycero-3-phosphocholines Amines Carbonyl compounds Carboxylic acid esters Dialkyl phosphates Fatty acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Organic salts Organopnictogen compounds Phosphocholines Secondary alcohols Tetraalkylammonium salts 1-acyl-sn-glycero-3-phosphocholine Alcohol Aliphatic acyclic compound Alkyl phosphate Amine Carbonyl group Carboxylic acid derivative Carboxylic acid ester Dialkyl phosphate Fatty acid ester Fatty acyl Hydrocarbon derivative Monocarboxylic acid or derivatives 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 Secondary alcohol Tetraalkylammonium salt Aliphatic acyclic compounds 1-O-acyl-sn-glycero-3-phosphocholine Monoacylglycerophosphocholines lysophosphatidylcholine 18:0 Solid logp 2.53 ALOGPS logs -6.41 ALOGPS logp 2.08 ChemAxon pka_strongest_acidic 1.86 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac (2-{[(2R)-2-hydroxy-3-(octadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium ChemAxon average_mass 523.6832 ChemAxon mono_mass 523.363789599 ChemAxon smiles [H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C ChemAxon formula C26H54NO7P ChemAxon inchi InChI=1S/C26H54NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)32-23-25(28)24-34-35(30,31)33-22-21-27(2,3)4/h25,28H,5-24H2,1-4H3/t25-/m1/s1 ChemAxon inchikey IHNKQIMGVNPMTC-RUZDIDTESA-N ChemAxon polar_surface_area 105.12 ChemAxon refractivity 151.48 ChemAxon polarizability 61.71 ChemAxon rotatable_bond_count 26 ChemAxon acceptor_count 4 ChemAxon donor_count 1 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::NmrOneD 338388 Specdb::NmrOneD 338389 Specdb::NmrOneD 338390 Specdb::NmrOneD 338391 Specdb::NmrOneD 338392 Specdb::NmrOneD 338393 Specdb::NmrOneD 338394 Specdb::NmrOneD 338395 Specdb::NmrOneD 338396 Specdb::NmrOneD 338397 Specdb::NmrOneD 338398 Specdb::NmrOneD 338399 Specdb::NmrOneD 338400 Specdb::NmrOneD 338401 Specdb::NmrOneD 338402 Specdb::NmrOneD 338403 Specdb::NmrOneD 338404 Specdb::NmrOneD 338405 Specdb::NmrOneD 338406 Specdb::NmrOneD 338407 Specdb::MsMs 2241468 Specdb::MsMs 2242348 Specdb::MsMs 2243534 Specdb::MsMs 2269774 Specdb::MsMs 2269775 Specdb::MsMs 2269776 Specdb::MsMs 2288823 Specdb::MsMs 2288824 Specdb::MsMs 2288825 Specdb::MsMs 2331986 Specdb::MsMs 2331987 Specdb::MsMs 2331988 Specdb::MsMs 2649624 Specdb::MsMs 2649625 Specdb::MsMs 2649626 Specdb::MsMs 3019932 Specdb::MsMs 3019933 Specdb::MsMs 3019934 Specdb::CMs 39493 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 Blood 30 +/- 5 uM By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Blood Detected by DFI-MS/MS (P180) in periparturient Holstein cows. Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13. 24630653 Blood 14-82 uM By LC-MS/MS Artegoitia VM, Middleton JL, Harte FM, Campagna SR, de Veth MJ: Choline and choline metabolite patterns and associations in blood and milk during lactation in dairy cows. PLoS One. 2014 Aug 26;9(8):e103412. doi: 10.1371/journal.pone.0103412. eCollection 2014. 25157578 Liver 2.1 +/- 0.4 nmol/g of tissue By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Liver Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 Longissimus Thoracis Muscle 0.07 +/- 0.02 nmol/g of tissue By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Placenta 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 Ruminal Fluid 0.2 +/- 0.1 uM By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Ruminal Fluid 0.11 +/- 0.02 uM Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured DFI-MS/MS. 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 0.11 +/- 0.02 uM 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. Semimembranosus Muscle 0.08 +/- 0.03 nmol/g of tissue By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Testis 0.16 +/- 0.03 nmol/g of tissue By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 435389 497299 FDB027535 73858 CPD-8345 C04230 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)