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4-Methylthio-2-oxobutanoate (YMDB00421)

Identification
YMDB IDYMDB00421
Name4-Methylthio-2-oxobutanoate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2-Oxo-4-methylthiobutanoic acid, also known as 4-(methylsulfanyl)-2-oxobutanoate or 2-keto-4-methylthiobutyrate, 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. 2-Oxo-4-methylthiobutanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
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-Phenylalanine → L-Methionine + 2-Ketobutyric acid
1,2-Dihydroxy-3-keto-5-methylthiopentene + oxygen → 4-Methylthio-2-oxobutanoate + hydron + Formic acid
KEGG Reactions
5-(methylsulfanyl)-2,3-dioxopentyl phosphate + water → hydron + 4-Methylthio-2-oxobutanoate + phosphate + Formic acid
4-Methylthio-2-oxobutanoate + L-Glutamic acid → L-Methionine + Oxoglutaric acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0f79-9620000000-a37f1649aaa00fe355f6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0uyr-7940000000-be5c411217da093f2c8aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f79-9620000000-a37f1649aaa00fe355f6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0uyr-7940000000-be5c411217da093f2c8aJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-9200000000-1471d6fe57ac965a873dJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0g4j-9400000000-16ddd3b5c053991fac9aJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-0a6t-0900000000-ed86a80611ad68e921e2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0002-9000000000-9b1238b1c990e180a476JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-0002-9000000000-a0fb6b922f7482546f1fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-0002-1900000000-f3facf4268a57538266cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-0002-2900000000-71e4f52b95b529acc1a3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-0002-5900000000-c6325fbf5479dbaa355cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-0002-7900000000-bccb79b226dccd29e36fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0002-9700000000-8e6b66c2a5dd967a9539JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0002-9500000000-dee1d47be79038a62ac8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0002-9200000000-184f804af473361e56d4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0002-9200000000-9f652bc59797907a90e8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0002-9100000000-2924be77506cc359576fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0002-9000000000-ac83262a096530d8343fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0002-9000000000-12841f2d918636eb3ba8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, negativesplash10-0002-9000000000-beb5b9021683b7e71f41JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, negativesplash10-0a4i-9000000000-5c4795e954d5c3e9b74eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0006-0900000000-a7b6fa585a128c4bbf25JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0006-0900000000-5d4054fa9cdf6414108dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0006-0900000000-70154862c61d3d6ece44JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f8a-1900000000-ed36a40a48bf904312f4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zir-9700000000-7bbe813aa31ceba0b525JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9100000000-89ba14ad10b374e8daabJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9200000000-b9179ec180a89222c147JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9100000000-63d77e1e6b7bea5353feJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-31b5d7804293c55c928eJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
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

Protein Details
1. Enolase-phosphatase E1
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
Protein Details
2. Aromatic amino acid aminotransferase 2
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.