Record Information
Version2.0
Creation Date2012-05-31 13:54:25 -0600
Update Date2015-06-03 15:54:11 -0600
Secondary Accession Numbers
  • ECMDB01553
Identification
Name:2-Oxo-4-methylthiobutanoic acid
Description2-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)
Structure
Thumb
Synonyms:
  • α-keto-γ-methylthiobutyrate
  • α-keto-γ-methylthiobutyric acid
  • α-keto-4-methylthiobutyrate
  • α-keto-4-methylthiobutyric acid
  • α-ketomethiobutyrate
  • α-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
Chemical Formula:C5H8O3S
Weight:Average: 148.18
Monoisotopic: 148.019414812
InChI Key:SXFSQZDSUWACKX-UHFFFAOYSA-N
InChI:InChI=1S/C5H8O3S/c1-9-3-2-4(6)5(7)8/h2-3H2,1H3,(H,7,8)
CAS number:583-92-6
IUPAC Name:4-(methylsulfanyl)-2-oxobutanoic acid
Traditional IUPAC Name:2-oxo-4-thiomethylbutyric acid
SMILES:CSCCC(=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
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
  • Cysteine and methionine metabolism ec00270
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0f79-9620000000-a37f1649aaa00fe355f6View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0uyr-7940000000-be5c411217da093f2c8aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f79-9620000000-a37f1649aaa00fe355f6View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0uyr-7940000000-be5c411217da093f2c8aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-9200000000-1471d6fe57ac965a873dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0g4j-9400000000-16ddd3b5c053991fac9aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f8a-1900000000-ed36a40a48bf904312f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zir-9700000000-7bbe813aa31ceba0b525View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9100000000-89ba14ad10b374e8daabView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9200000000-b9179ec180a89222c147View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9100000000-63d77e1e6b7bea5353feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-31b5d7804293c55c928eView in MoNA
References
References:
  • 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. Pubmed: 22080510
  • 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. Pubmed: 21097882
  • Martensson J: The occurrence of 4-methylthio-2-hydroxybutyrate in human urine. Anal Biochem. 1986 Apr;154(1):43-9. Pubmed: 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. Pubmed: 7848263
  • 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
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.
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16723
HMDB IDHMDB01553
Pubchem Compound ID473
Kegg IDC01180
ChemSpider ID460
Wikipedia IDNot Available
BioCyc IDCPD-479
EcoCyc IDCPD-479
Ligand ExpoKMT

Enzymes

General function:
Involved in transferase activity
Specific function:
An aromatic amino acid + 2-oxoglutarate = an aromatic oxo acid + L-glutamate
Gene Name:
tyrB
Uniprot ID:
P04693
Molecular weight:
43537
Reactions
An aromatic amino acid + 2-oxoglutarate = an aromatic oxo acid + L-glutamate.