2.02012-05-31 13:54:25 -06002015-06-03 15:54:11 -0600ECMDB01553M2MDB0004182-Oxo-4-methylthiobutanoic acid2-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)α-keto-γ-methylthiobutyrateα-keto-γ-methylthiobutyric acidα-keto-4-methylthiobutyrateα-keto-4-methylthiobutyric acidα-ketomethiobutyrateα-ketomethiobutyric acid2-Keto-4-methylthiobutanoate2-Keto-4-methylthiobutanoic acid2-Keto-4-methylthiobutyrate2-Keto-4-methylthiobutyric acid2-Keto-methyl-thio-butyrate2-Keto-methyl-thio-butyric acid2-Ketomethiobutyrate2-Ketomethiobutyric acid2-Oxo-4-methylthiobutanoate2-Oxo-4-methylthiobutanoic acid2-Oxomethionine4-Methylthio-2-ketobutanoate4-Methylthio-2-ketobutanoic acid4-Methylthio-2-ketobutyrate4-Methylthio-2-ketobutyric acid4-Methylthio-2-oxobutanoate4-Methylthio-2-oxobutanoic acid4-Methylthio-2-oxobutyrate4-Methylthio-2-oxobutyric acida-keto-4-Methylthiobutyratea-keto-4-Methylthiobutyric acida-keto-g-Methylthiobutyratea-keto-g-Methylthiobutyric acida-keto-Methiolbutyratea-keto-Methiolbutyric acida-Ketomethiobutyratea-Ketomethiobutyric acidAlpha-Keto-4-methylthiobutyrateAlpha-Keto-4-methylthiobutyric acidAlpha-Keto-gamma-methylthiobutyrateAlpha-Keto-gamma-methylthiobutyric acidalpha-keto-MethiolbutyrateAlpha-Keto-methiolbutyric acidAlpha-KetomethiobutyrateAlpha-Ketomethiobutyric acidKeto-4-methylthiobutyrateKeto-4-methylthiobutyric acidKetomethiobutyrateKetomethiobutyric acidKMTBMethylthiobutyrateMethylthiobutyric acidα-keto-4-Methylthiobutyrateα-keto-4-Methylthiobutyric acidα-keto-Methiolbutyrateα-keto-Methiolbutyric acidα-keto-γ-Methylthiobutyrateα-keto-γ-Methylthiobutyric acidα-Ketomethiobutyrateα-Ketomethiobutyric acidC5H8O3S148.18148.0194148124-(methylsulfanyl)-2-oxobutanoic acid2-oxo-4-thiomethylbutyric acid583-92-6CSCCC(=O)C(O)=OInChI=1S/C5H8O3S/c1-9-3-2-4(6)5(7)8/h2-3H2,1H3,(H,7,8)SXFSQZDSUWACKX-UHFFFAOYSA-NSolidOuter membraneInner membranelogp-0.07logs-1.30solubility7.44e+00 g/llogp1.12pka_strongest_acidic3.3pka_strongest_basic-9.7iupac4-(methylsulfanyl)-2-oxobutanoic acidaverage_mass148.18mono_mass148.019414812smilesCSCCC(=O)C(O)=OformulaC5H8O3SinchiInChI=1S/C5H8O3S/c1-9-3-2-4(6)5(7)8/h2-3H2,1H3,(H,7,8)inchikeySXFSQZDSUWACKX-UHFFFAOYSA-Npolar_surface_area54.37refractivity35.07polarizability14.21rotatable_bond_count4acceptor_count3donor_count1physiological_charge-1formal_charge0Cysteine and methionine metabolismec00270Specdb::CMs1115Specdb::CMs1139Specdb::CMs2697Specdb::CMs31345Specdb::CMs31346Specdb::CMs38123Specdb::CMs146627Specdb::NmrOneD148180Specdb::NmrOneD148181Specdb::NmrOneD148182Specdb::NmrOneD148183Specdb::NmrOneD148184Specdb::NmrOneD148185Specdb::NmrOneD148186Specdb::NmrOneD148187Specdb::NmrOneD148188Specdb::NmrOneD148189Specdb::NmrOneD148190Specdb::NmrOneD148191Specdb::NmrOneD148192Specdb::NmrOneD148193Specdb::NmrOneD148194Specdb::NmrOneD148195Specdb::NmrOneD148196Specdb::NmrOneD148197Specdb::NmrOneD148198Specdb::NmrOneD148199Specdb::MsMs20498Specdb::MsMs20499Specdb::MsMs20500Specdb::MsMs22049Specdb::MsMs22050Specdb::MsMs22051Specdb::MsMs1470857Specdb::MsMs1471159Specdb::MsMs1471182Specdb::MsMs1472500Specdb::MsMs1472501Specdb::MsMs1472502Specdb::MsMs1472503Specdb::MsMs1472504Specdb::MsMs1472505Specdb::MsMs1472506Specdb::MsMs1472507Specdb::MsMs1472508Specdb::MsMs1472509Specdb::MsMs1472510Specdb::MsMs1472511Specdb::MsMs1472512Specdb::MsMs1477520Specdb::MsMs1477521Specdb::MsMs1477522HMDB01553473460C0118016723CPD-479KMTKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.AMartensson J: The occurrence of 4-methylthio-2-hydroxybutyrate in human urine. Anal Biochem. 1986 Apr;154(1):43-9.3706736Quash 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):1017-25.7848263Brodelius, 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 aminotransferaseP04693TYRB_ECOLItyrBhttp://ecmdb.ca/proteins/P04693.xml2-Oxo-4-methylthiobutanoic acid + L-Glutamate <> L-Methionine + alpha-KetoglutarateR073962-Oxo-4-methylthiobutanoic acid + hydroxyl radical > Hydrogen ion + ethylene + methanethiol + Carbon dioxideRXN-12539L-Methionine + a 2-oxo carboxylate 2-Oxo-4-methylthiobutanoic acid + a standard α amino acidR15-RXNL-Methionine + a 2-oxo acid > 2-Oxo-4-methylthiobutanoic acid + an L-amino acid