2-oxo-4-methylthiobutanoate (PAMDB120327)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120327
Identification
Name: 2-oxo-4-methylthiobutanoate
Description:The 2-oxo monocarboxylic acid anion derived from 4-methylthio-2-oxobutanoic acid. The major microspecies at pH 7.3, it is formed from L-methionine via the action of methionine transaminase.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2-oxo-4-methylthiobutanoate
  • 4-methylthio-2-oxobutanoate
Chemical Formula: C5H7O3S
Average Molecular Weight: 147.168
Monoisotopic Molecular Weight: 148.01941
InChI Key: SXFSQZDSUWACKX-UHFFFAOYSA-M
InChI:InChI=1S/C5H8O3S/c1-9-3-2-4(6)5(7)8/h2-3H2,1H3,(H,7,8)/p-1
CAS number: 583-92-6
IUPAC Name:4-(methylsulfanyl)-2-oxobutanoate
Traditional IUPAC Name: 2-oxo-4-thiomethylbutyric acid
SMILES:CSCCC(C([O-])=O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as thia fatty acids. These are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Lipids and lipid-like molecules
Sub ClassFatty Acyls
Direct Parent Thia 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 Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.44 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity35.07 m3·mol-1ChemAxon
Polarizability14.21 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
1,2-dihydroxy-5-(methylthio)pent-1-en-3-one + Oxygen → Hydrogen ion + 2-oxo-4-methylthiobutanoate + formate
2-oxo-4-methylthiobutanoate + hydroxyl radical → ethylene + methanethiol + Carbon dioxide
L-Methionine + alpha-Ketoglutarate → 2-oxo-4-methylthiobutanoate + L-glutamate
L-Methionine + 2-Oxo-carboxylates → 2-oxo-4-methylthiobutanoate + Amino-Acids-20
Pathways:
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
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:
  • Heilbronn J, Wilson J, Berger BJ (1999)Tyrosine aminotransferase catalyzes the final step of methionine recycling in Klebsiella pneumoniae. Journal of bacteriology 181, Pubmed: 10074065
  • Dolzan M, Johansson K, Roig-Zamboni V, Campanacci V, Tegoni M, Schneider G, Cambillau C (2004)Crystal structure and reactivity of YbdL from Escherichia coli identify a methionine aminotransferase function. FEBS letters 571, Pubmed: 15280032
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
METABOLIGHTSMTBLC16723
HMDBHMDB01553
BIGG228408
CHEMSPIDER3776616
PUBCHEM4584184
LIGAND-CPDC01180
CHEBI16723