1.0 2016-09-30 22:49:55 UTC 2020-06-04 20:04:02 UTC BMDB0002013 BMDB02013 Butyrylcarnitine Butyrylcarnitine, also known as O-butanoylcarnitine, belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Thus, butyrylcarnitine is considered to be a fatty ester lipid molecule. Butyrylcarnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Butyrylcarnitine exists in all eukaryotes, ranging from yeast to humans. Butyrylcarnitine is a potentially toxic compound. Butyrylcarnitine has been found to be associated with several diseases known as obesity, eosinophilic esophagitis, and pregnancy; also butyrylcarnitine has been linked to several inborn metabolic disorders including short chain acyl-coa dehydrogenase deficiency and very long chain acyl-coa dehydrogenase deficiency. (3R)-3-(Butyryloxy)-4-(trimethylammonio)butanoate Butyryl-L-carnitine L-Carnitine butyryl ester N-Butyryl-L-(-)-carnitin O-Butanoyl-(R)-carnitine (3R)-3-(Butyryloxy)-4-(trimethylammonio)butanoic acid Butylcarnitine O-Butanoyl-carnitine O-Butanoylcarnitine Butyrylcarnitine C11H21NO4 231.292 231.14705816 (3R)-3-(butanoyloxy)-4-(trimethylazaniumyl)butanoate O-butanoylcarnitine 25576-40-3 CCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C InChI=1S/C11H21NO4/c1-5-6-11(15)16-9(7-10(13)14)8-12(2,3)4/h9H,5-8H2,1-4H3/t9-/m1/s1 QWYFHHGCZUCMBN-SECBINFHSA-N belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acid esters Acyl carnitines Amines Carbonyl compounds Carboxylic acid esters Carboxylic acid salts Carboxylic acids Dicarboxylic acids and derivatives Hydrocarbon derivatives Organic oxides Organic salts Organopnictogen compounds Tetraalkylammonium salts Acyl-carnitine Aliphatic acyclic compound Amine Carbonyl group Carboxylic acid Carboxylic acid derivative Carboxylic acid ester Carboxylic acid salt Dicarboxylic acid or derivatives Hydrocarbon derivative Organic nitrogen compound Organic oxide Organic oxygen compound Organic salt Organonitrogen compound Organooxygen compound Organopnictogen compound Quaternary ammonium salt Tetraalkylammonium salt Aliphatic acyclic compounds Fatty acyl carnitines O-butanoylcarnitine Solid logp -2.10 ALOGPS logs -3.74 ALOGPS logp -3.3 ChemAxon pka_strongest_acidic 4.27 ChemAxon pka_strongest_basic -7.1 ChemAxon iupac (3R)-3-(butanoyloxy)-4-(trimethylazaniumyl)butanoate ChemAxon average_mass 231.292 ChemAxon mono_mass 231.14705816 ChemAxon smiles CCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C ChemAxon formula C11H21NO4 ChemAxon inchi InChI=1S/C11H21NO4/c1-5-6-11(15)16-9(7-10(13)14)8-12(2,3)4/h9H,5-8H2,1-4H3/t9-/m1/s1 ChemAxon inchikey QWYFHHGCZUCMBN-SECBINFHSA-N ChemAxon polar_surface_area 66.43 ChemAxon refractivity 81.86 ChemAxon polarizability 24.8 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 3 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::MsMs 2235894 Specdb::MsMs 2237504 Specdb::MsMs 2237952 Specdb::MsMs 2239604 Specdb::MsMs 2239979 Specdb::MsMs 2241751 Specdb::MsMs 2447274 Specdb::MsMs 2447275 Specdb::MsMs 2447276 Specdb::CMs 161674 Specdb::NmrOneD 148720 Specdb::NmrOneD 148721 Specdb::NmrOneD 148722 Specdb::NmrOneD 148723 Specdb::NmrOneD 148724 Specdb::NmrOneD 148725 Specdb::NmrOneD 148726 Specdb::NmrOneD 148727 Specdb::NmrOneD 148728 Specdb::NmrOneD 148729 Specdb::NmrOneD 148730 Specdb::NmrOneD 148731 Specdb::NmrOneD 148732 Specdb::NmrOneD 148733 Specdb::NmrOneD 148734 Specdb::NmrOneD 148735 Specdb::NmrOneD 148736 Specdb::NmrOneD 148737 Specdb::NmrOneD 148738 Specdb::NmrOneD 148739 Blood 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 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 Fibroblasts 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 Liver 0.36 +/- 0.08 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 Longissimus Thoracis Muscle 16 +/- 6 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 Milk By GC-MS and LC-MS/MS Characterization of the biochemical variability of bovine milk using metabolomics Milk Commercial, conventional whole milk Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8 Milk 4.4 +/- 0.2 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 5.8 +/- 0.1 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 6.6 +/- 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 3.99 +/- 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 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 0.05 +/- 0.02 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 Semimembranosus Muscle 22 +/- 8 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 2.8 +/- 0.7 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 FDB022795 213144 184820 21949 C02862 C00052220 6436 Lozano Pedro; Daz Mirta; de Diego Teresa; Iborra Jose L Ester synthesis from trimethylammonium alcohols in dry organic media catalyzed by immobilized Candida antarctica lipase B. Biotechnology and bioengineering (2003), 82(3), 352-8. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 Characterization of the biochemical variability of bovine milk using metabolomics A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)