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2-Oxo-4-methylthiobutanoic acid (M2MDB000418)

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
MOLSDFPDBSMILESInChI
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:
2-Oxo-4-methylthiobutanoic acid + L-Glutamate <> L-Methionine + alpha-Ketoglutarate
2-Oxo-4-methylthiobutanoic acid + hydroxyl radical > Hydrogen ion + ethylene + methanethiol + Carbon dioxide
L-Methionine + a 2-oxo carboxylate 2-Oxo-4-methylthiobutanoic acid + a standard &alpha; amino acid
L-Methionine + a 2-oxo acid > 2-Oxo-4-methylthiobutanoic acid + an L-amino acid
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-0a6t-0900000000-ed86a80611ad68e921e2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0002-9000000000-9b1238b1c990e180a476View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-0002-9000000000-a0fb6b922f7482546f1fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-0002-1900000000-f3facf4268a57538266cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-0002-2900000000-71e4f52b95b529acc1a3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-0002-5900000000-c6325fbf5479dbaa355cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-0002-7900000000-bccb79b226dccd29e36fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0002-9700000000-8e6b66c2a5dd967a9539View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0002-9500000000-dee1d47be79038a62ac8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0002-9200000000-184f804af473361e56d4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0002-9200000000-9f652bc59797907a90e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0002-9100000000-2924be77506cc359576fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0002-9000000000-ac83262a096530d8343fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0002-9000000000-12841f2d918636eb3ba8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, negativesplash10-0002-9000000000-beb5b9021683b7e71f41View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, negativesplash10-0a4i-9000000000-5c4795e954d5c3e9b74eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0006-0900000000-a7b6fa585a128c4bbf25View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0006-0900000000-5d4054fa9cdf6414108dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0006-0900000000-70154862c61d3d6ece44View 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
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
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

Protein Details
1. Aromatic-amino-acid aminotransferase
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.