1.0 2016-09-30 22:37:28 UTC 2020-06-04 19:04:37 UTC BMDB0000848 BMDB00848 Stearoylcarnitine Stearoylcarnitine, also known as acylcarnitine C18:0, 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, stearoylcarnitine is considered to be a fatty ester lipid molecule. Stearoylcarnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, stearoylcarnitine is involved in the metabolic pathway called the mitochondrial Beta-oxidation OF long chain saturated fatty acids pathway. (-)-Stearoylcarnitine (R)-Octadecanoylcarnitine (R)-Stearoylcarnitine Acylcarnitine C18:0 L-Stearoylcarnitine O-Octadecanoyl-(R)-carnitine O-Octadecanoyl-R-carnitine O-Stearoyl-L-carnitine Octadecanoylcarnitine 3-(Octadecanoyloxy)-4-(trimethylammonio)butanoate O-Octadecanoylcarnitine 3-(Octadecanoyloxy)-4-(trimethylammonio)butanoic acid (R)-3-Carboxy-N,N,N-trimethyl-2-[(1-oxooctadecyl)oxy]-1-propanaminium inner salt L-(3-Carboxy-2-hydroxypropyl)trimethyl-ammonium stearate hydroxide inner salt L-Stearic acid ester with (3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner salt Octadecanoyl-L-carnitine Stearoyl-L-carnitine Stearoylcarnitine C25H49NO4 427.67 427.366159062 (3R)-3-(octadecanoyloxy)-4-(trimethylazaniumyl)butanoate stearoylcarnitine 1976-27-8 CCCCCCCCCCCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C InChI=1S/C25H49NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25(29)30-23(21-24(27)28)22-26(2,3)4/h23H,5-22H2,1-4H3/t23-/m1/s1 FNPHNLNTJNMAEE-HSZRJFAPSA-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-acyl-L-carnitine Solid logp 2.62 ALOGPS logs -7.68 ALOGPS logp 2.92 ChemAxon pka_strongest_acidic 4.22 ChemAxon pka_strongest_basic -7.1 ChemAxon iupac (3R)-3-(octadecanoyloxy)-4-(trimethylazaniumyl)butanoate ChemAxon average_mass 427.67 ChemAxon mono_mass 427.366159062 ChemAxon smiles CCCCCCCCCCCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C ChemAxon formula C25H49NO4 ChemAxon inchi InChI=1S/C25H49NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25(29)30-23(21-24(27)28)22-26(2,3)4/h23H,5-22H2,1-4H3/t23-/m1/s1 ChemAxon inchikey FNPHNLNTJNMAEE-HSZRJFAPSA-N ChemAxon polar_surface_area 66.43 ChemAxon refractivity 146.28 ChemAxon polarizability 54.7 ChemAxon rotatable_bond_count 22 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::CMs 162917 Specdb::CMs 1079464 Specdb::CMs 1079466 Specdb::NmrOneD 5173 Specdb::NmrTwoD 2007 Specdb::MsMs 1218121 Specdb::MsMs 1218122 Specdb::MsMs 1218123 Specdb::MsMs 2679969 Specdb::MsMs 2679970 Specdb::MsMs 2679971 Blood 0.021 +/- 0.008 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 Liver 0.008 +/- 0.001 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 0.02 +/- 0.01 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 0.0067 +/- 0.0021 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 0.006 +/- 0.002 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 0.02 +/- 0.01 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 FDB022278 52922056 84644 1585824 5811 Zhou, Qingzhong. Synthesis of branched-chain analogs of stearoyl carnitine and tests for their abilities to inhibited protein kinase C. Beijing Daxue Xuebao, Ziran Kexueban (1992), 28(2), 143-9. BMDBP00245 Carnitine O-palmitoyltransferase 1, muscle isoform Q58DK1 CPT1B Enzyme BMDBP00246 Carnitine O-palmitoyltransferase 2, mitochondrial Q2KJB7 CPT2 Enzyme