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Identification
YMDB IDYMDB00421
Name4-Methylthio-2-oxobutanoate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description4-Methylthio-2-oxobutanoic acid is the direct precursor of methional. Methional is a compound responsible for a potato-like aroma.
Structure
Thumb
Synonyms
  • 2-keto-4-methylthiobutyrate
  • 2-keto-4-methylthiobutyric acid
  • 2-ketomethiobutyrate
  • 2-Oxo-4-methylthiobutanoate
  • 2-oxo-4-methylthiobutanoic acid
  • 4-methylthio-2-ketobutanoate
  • 4-methylthio-2-ketobutyrate
  • 4-methylthio-2-oxobutanoate
  • 4-methylthio-2-oxobutanoic acid
  • 4-methylthio-2-oxobutyrate
  • Butanoic acid, 4-(methylthio)-2-oxo-
  • Butyric acid, 4-(methylthio)-2-oxo-
  • keto-4-methylthiobutyrate
  • ketomethiobutyrate
  • ketomethiobutyric acid
  • KMTB
  • methylthiobutyrate
  • methylthiobutyric acid
  • 2-Oxomethionine
  • 4-(METHYLsulfanyl)-2-oxobutanoIC ACID
  • alpha-oxo-gamma-Methylthiobutyric acid
  • 4-(METHYLsulfanyl)-2-oxobutanoate
  • 4-(METHYLsulphanyl)-2-oxobutanoate
  • 4-(METHYLsulphanyl)-2-oxobutanoic acid
  • a-oxo-g-Methylthiobutyrate
  • a-oxo-g-Methylthiobutyric acid
  • alpha-oxo-gamma-Methylthiobutyrate
  • Α-oxo-γ-methylthiobutyrate
  • Α-oxo-γ-methylthiobutyric acid
  • 4-Methylthio-2-ketobutanoic acid
  • alpha-Keto-methiolbutyric acid
  • 2-Keto-4-methylthiobutanoic acid
  • 2-Keto-4-thiomethylbutyrate
  • 2-oxo-4-Thiomethylbutyric acid
  • alpha-Keto-gamma-methiolbutyrate
  • alpha-Ketomethionine
  • alpha-Oxomethionine
  • 2-Keto-4-methylthiobutyric acid, monosodium salt
  • 2-Ketothiomethylbutyric acid
  • 4-Methylthio-2-oxobutyric acid
  • S-Methyl-alpha-ketobutyric acid
  • 2-Keto-4-methylthiobutyric acid, calcium salt
  • 4-Methylthio-2-ketobutyric acid
  • gamma-Methiol-keto-butyric acid
  • 4-Methylmercapto-2-oxobutyrate
CAS number583-92-6
WeightAverage: 148.18
Monoisotopic: 148.019414812
InChI KeySXFSQZDSUWACKX-UHFFFAOYSA-N
InChIInChI=1S/C5H8O3S/c1-9-3-2-4(6)5(7)8/h2-3H2,1H3,(H,7,8)
IUPAC Name4-(methylsulfanyl)-2-oxobutanoic acid
Traditional IUPAC Name2-oxo-4-thiomethylbutyric acid
Chemical FormulaC5H8O3S
SMILESCSCCC(=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as thia fatty acids. These are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentThia fatty acids
Alternative Parents
Substituents
  • Short-chain keto acid
  • Thia fatty acid
  • Alpha-keto acid
  • Keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkylthioether
  • Monocarboxylic acid or derivatives
  • Sulfenyl compound
  • Thioether
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility7.44 g/LALOGPS
logP-0.07ALOGPS
logP1.12ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.3ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity35.07 m³·mol⁻¹ChemAxon
Polarizability14.21 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Methionine metabolism and salvagePW002384 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Cysteine and methionine metabolismec00270 Map00270
SMPDB Reactions
4-Methylthio-2-oxobutanoate + L-PhenylalanineL-Methionine + 2-Ketobutyric acid
1,2-Dihydroxy-3-keto-5-methylthiopentene + oxygen4-Methylthio-2-oxobutanoate + hydron + Formic acid
KEGG Reactions
5-(methylsulfanyl)-2,3-dioxopentyl phosphate + waterhydron + 4-Methylthio-2-oxobutanoate + phosphate + Formic acid
4-Methylthio-2-oxobutanoate + L-Glutamic acidL-Methionine + Oxoglutaric acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Subhi, A. L., Diegelman, P., Porter, C. W., Tang, B., Lu, Z. J., Markham, G. D., Kruger, W. D. (2003). "Methylthioadenosine phosphorylase regulates ornithine decarboxylase by production of downstream metabolites." J Biol Chem 278:49868-49873.14506228
Synthesis Reference: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.
External Links:
ResourceLink
CHEBI ID33574
HMDB IDHMDB01553
Pubchem Compound ID473
Kegg IDC01180
ChemSpider ID460
FOODB IDFDB030353
Wikipedia IDNot Available
BioCyc IDCPD-479

Enzymes

General function:
Involved in catalytic activity
Specific function:
Bifunctional enzyme that catalyzes the enolization of 2,3-diketo-5-methylthiopentyl-1-phosphate (DK-MTP-1-P) into the intermediate 2-hydroxy-3-keto-5-methylthiopentenyl-1-phosphate (HK-MTPenyl-1-P), which is then dephosphorylated to form the acireductone 1,2-dihydroxy-3-keto-5-methylthiopentene (DHK-MTPene)
Gene Name:
UTR4
Uniprot ID:
P32626
Molecular weight:
25187.19922
Reactions
5-(methylthio)-2,3-dioxopentyl phosphate + H(2)O → 1,2-dihydroxy-5-(methylthio)pent-1-en-3-one + phosphate.
2-Phosphoglycolate + H2O → glycolate + phosphate
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Has aromatic amino acid transaminase activity and kynurenine aminotransferase activity
Gene Name:
ARO9
Uniprot ID:
P38840
Molecular weight:
58527.0
Reactions
An aromatic amino acid + 2-oxoglutarate → an aromatic oxo acid + L-glutamate.