2.0 2012-05-31 13:54:25 -0600 2015-06-03 15:54:11 -0600 ECMDB01553 M2MDB000418 2-Oxo-4-methylthiobutanoic acid 2-oxo-4-methylthiobutanoic acid is the direct precursor of methional. It is an intermediate of cysteine and methionine metabolism. It is converted to L-methionine via tyrosine aminotransferase. (KEGG) &alpha;-keto-&gamma;-methylthiobutyrate &alpha;-keto-&gamma;-methylthiobutyric acid &alpha;-keto-4-methylthiobutyrate &alpha;-keto-4-methylthiobutyric acid &alpha;-ketomethiobutyrate &alpha;-ketomethiobutyric acid 2-Keto-4-methylthiobutanoate 2-Keto-4-methylthiobutanoic acid 2-Keto-4-methylthiobutyrate 2-Keto-4-methylthiobutyric acid 2-Keto-methyl-thio-butyrate 2-Keto-methyl-thio-butyric acid 2-Ketomethiobutyrate 2-Ketomethiobutyric acid 2-Oxo-4-methylthiobutanoate 2-Oxo-4-methylthiobutanoic acid 2-Oxomethionine 4-Methylthio-2-ketobutanoate 4-Methylthio-2-ketobutanoic acid 4-Methylthio-2-ketobutyrate 4-Methylthio-2-ketobutyric acid 4-Methylthio-2-oxobutanoate 4-Methylthio-2-oxobutanoic acid 4-Methylthio-2-oxobutyrate 4-Methylthio-2-oxobutyric acid a-keto-4-Methylthiobutyrate a-keto-4-Methylthiobutyric acid a-keto-g-Methylthiobutyrate a-keto-g-Methylthiobutyric acid a-keto-Methiolbutyrate a-keto-Methiolbutyric acid a-Ketomethiobutyrate a-Ketomethiobutyric acid Alpha-Keto-4-methylthiobutyrate Alpha-Keto-4-methylthiobutyric acid Alpha-Keto-gamma-methylthiobutyrate Alpha-Keto-gamma-methylthiobutyric acid alpha-keto-Methiolbutyrate Alpha-Keto-methiolbutyric acid Alpha-Ketomethiobutyrate Alpha-Ketomethiobutyric acid Keto-4-methylthiobutyrate Keto-4-methylthiobutyric acid Ketomethiobutyrate Ketomethiobutyric acid KMTB Methylthiobutyrate Methylthiobutyric acid α-keto-4-Methylthiobutyrate α-keto-4-Methylthiobutyric acid α-keto-Methiolbutyrate α-keto-Methiolbutyric acid α-keto-γ-Methylthiobutyrate α-keto-γ-Methylthiobutyric acid α-Ketomethiobutyrate α-Ketomethiobutyric acid C5H8O3S 148.18 148.019414812 4-(methylsulfanyl)-2-oxobutanoic acid 2-oxo-4-thiomethylbutyric acid 583-92-6 CSCCC(=O)C(O)=O InChI=1S/C5H8O3S/c1-9-3-2-4(6)5(7)8/h2-3H2,1H3,(H,7,8) SXFSQZDSUWACKX-UHFFFAOYSA-N Solid Outer membrane Inner membrane logp -0.07 ALOGPS logs -1.30 ALOGPS solubility 7.44e+00 g/l ALOGPS logp 1.12 ChemAxon pka_strongest_acidic 3.3 ChemAxon pka_strongest_basic -9.7 ChemAxon iupac 4-(methylsulfanyl)-2-oxobutanoic acid ChemAxon average_mass 148.18 ChemAxon mono_mass 148.019414812 ChemAxon smiles CSCCC(=O)C(O)=O ChemAxon formula C5H8O3S ChemAxon inchi InChI=1S/C5H8O3S/c1-9-3-2-4(6)5(7)8/h2-3H2,1H3,(H,7,8) ChemAxon inchikey SXFSQZDSUWACKX-UHFFFAOYSA-N ChemAxon polar_surface_area 54.37 ChemAxon refractivity 35.07 ChemAxon polarizability 14.21 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Cysteine and methionine metabolism ec00270 Specdb::CMs 1115 Specdb::CMs 1139 Specdb::CMs 2697 Specdb::CMs 31345 Specdb::CMs 31346 Specdb::CMs 38123 Specdb::CMs 146627 Specdb::NmrOneD 148180 Specdb::NmrOneD 148181 Specdb::NmrOneD 148182 Specdb::NmrOneD 148183 Specdb::NmrOneD 148184 Specdb::NmrOneD 148185 Specdb::NmrOneD 148186 Specdb::NmrOneD 148187 Specdb::NmrOneD 148188 Specdb::NmrOneD 148189 Specdb::NmrOneD 148190 Specdb::NmrOneD 148191 Specdb::NmrOneD 148192 Specdb::NmrOneD 148193 Specdb::NmrOneD 148194 Specdb::NmrOneD 148195 Specdb::NmrOneD 148196 Specdb::NmrOneD 148197 Specdb::NmrOneD 148198 Specdb::NmrOneD 148199 Specdb::MsMs 20498 Specdb::MsMs 20499 Specdb::MsMs 20500 Specdb::MsMs 22049 Specdb::MsMs 22050 Specdb::MsMs 22051 Specdb::MsMs 1470857 Specdb::MsMs 1471159 Specdb::MsMs 1471182 Specdb::MsMs 1472500 Specdb::MsMs 1472501 Specdb::MsMs 1472502 Specdb::MsMs 1472503 Specdb::MsMs 1472504 Specdb::MsMs 1472505 Specdb::MsMs 1472506 Specdb::MsMs 1472507 Specdb::MsMs 1472508 Specdb::MsMs 1472509 Specdb::MsMs 1472510 Specdb::MsMs 1472511 Specdb::MsMs 1472512 Specdb::MsMs 1477520 Specdb::MsMs 1477521 Specdb::MsMs 1477522 HMDB01553 473 460 C01180 16723 CPD-479 KMT Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A Martensson J: The occurrence of 4-methylthio-2-hydroxybutyrate in human urine. Anal Biochem. 1986 Apr;154(1):43-9. 3706736 Quash G, Roch AM, Chantepie J, Michal Y, Fournet G, Dumontet C: Methional derived from 4-methylthio-2-oxobutanoate is a cellular mediator of apoptosis in BAF3 lymphoid cells. Biochem J. 1995 Feb 1;305 ( Pt 3):1017-25. 7848263 Brodelius, P.; Hagerdal, B.; Mosbach, K. Immobilized whole cells of the yeast Trigonopsis variabilis containing D-amino acid oxidase for the production of a-keto acids. Enzyme Engineering (1980), 5 383-7. Aromatic-amino-acid aminotransferase P04693 TYRB_ECOLI tyrB http://ecmdb.ca/proteins/P04693.xml 2-Oxo-4-methylthiobutanoic acid + L-Glutamate <> L-Methionine + alpha-Ketoglutarate R07396 2-Oxo-4-methylthiobutanoic acid + hydroxyl radical > Hydrogen ion + ethylene + methanethiol + Carbon dioxide RXN-12539 L-Methionine + a 2-oxo carboxylate 2-Oxo-4-methylthiobutanoic acid + a standard &alpha; amino acid R15-RXN L-Methionine + a 2-oxo acid > 2-Oxo-4-methylthiobutanoic acid + an L-amino acid