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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-03-14 18:02:00 UTC
HMDB IDHMDB0001553
Secondary Accession Numbers
  • HMDB0013210
  • HMDB01553
  • HMDB13210
Metabolite Identification
Common Name2-Oxo-4-methylthiobutanoic acid
Description2-oxo-4-methylthiobutanoate, also known as 2-keto-4-methylthiobutyric acid, 2-keto-4-methylthiobutyrate or 4-(methylsulfanyl)-2-oxobutanoic acid, is a member of the class of compounds known as thia- fatty acids. Thia-fatty acids are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain. Thus, 2-oxo-4-methylthiobutanoate is a fatty acid lipid molecule. 2-oxo-4-methylthiobutanoate is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 2-oxo-4-methylthiobutanoate can be synthesized from L-methionine and butyric acid. 2-oxo-4-methylthiobutanoate can also be synthesized into S-adenosyl-4-methylthio-2-oxobutanoic acid. 2-oxo-4-methylthiobutanoate can be found in a number of food items such as cloves, highbush blueberries, common beets, and cashew nuts. 2-oxo-4-methylthiobutanoate can be found in urine. Within the cell, 2-oxo-4-methylthiobutanoate is primarily located in the cytoplasm and in the membrane. 2-oxo-4-methylthiobutanoate has been found in all living species, from bacteria to humans. In humans, 2-oxo-4-methylthiobutanoate is found to be involved in several metabolic disorders, some of those are S-adenosylhomocysteine (SAH) hydrolase deficiency, methylenetetrahydrofolate reductase deficiency (MTHFRD), methionine adenosyltransferase deficiency, and glycine N-methyltransferase deficiency. 4-Methylthio-2-oxobutanoic acid is the direct precursor of methional, which is a potent inducer of apoptosis in a BAF3 murine lymphoid cell line which is interleukin-3 (IL3)-dependent (PMID: 7848263 ).
Structure
Data?1547234171
Synonyms
ValueSource
2-Keto-4-methylthiobutyric acidChEBI
2-oxo-4-MethylthiobutanoateChEBI
2-OxomethionineChEBI
4-(METHYLsulfanyl)-2-oxobutanoIC ACIDChEBI
4-Methylthio-2-oxobutanoateChEBI
alpha-oxo-gamma-Methylthiobutyric acidChEBI
4-(Methylsulfanyl)-2-oxobutanoateKegg
2-Keto-4-methylthiobutyrateGenerator
4-(METHYLsulphanyl)-2-oxobutanoateGenerator
4-(METHYLsulphanyl)-2-oxobutanoic acidGenerator
4-Methylthio-2-oxobutanoic acidGenerator
a-oxo-g-MethylthiobutyrateGenerator
a-oxo-g-Methylthiobutyric acidGenerator
alpha-oxo-gamma-MethylthiobutyrateGenerator
Α-oxo-γ-methylthiobutyrateGenerator
Α-oxo-γ-methylthiobutyric acidGenerator
2-KetomethiobutyrateHMDB
4-Methylthio-2-ketobutanoateHMDB
4-Methylthio-2-ketobutanoic acidHMDB
4-Methylthio-2-ketobutyrateHMDB
4-Methylthio-2-oxobutyrateHMDB
alpha-Keto-methiolbutyric acidHMDB
Keto-4-methylthiobutyrateHMDB
KetomethiobutyrateHMDB
Ketomethiobutyric acidHMDB
KMTBHMDB
MethylthiobutyrateHMDB
Methylthiobutyric acidHMDB
2-Keto-4-methylthiobutanoic acidHMDB
2-Keto-4-thiomethylbutyrateHMDB
2-oxo-4-Thiomethylbutyric acidHMDB
alpha-Keto-gamma-methiolbutyrateHMDB
alpha-KetomethionineHMDB
alpha-OxomethionineHMDB
2-Keto-4-methylthiobutyric acid, monosodium saltHMDB
2-Ketothiomethylbutyric acidHMDB
4-Methylthio-2-oxobutyric acidHMDB
S-Methyl-alpha-ketobutyric acidHMDB
2-Keto-4-methylthiobutyric acid, calcium saltHMDB
4-Methylthio-2-ketobutyric acidHMDB
gamma-Methiol-keto-butyric acidHMDB
4-Methylmercapto-2-oxobutyrateHMDB
2-oxo-4-Methylthiobutanoic acidKEGG
Chemical FormulaC5H8O3S
Average Molecular Weight148.18
Monoisotopic Molecular Weight148.019414812
IUPAC Name4-(methylsulfanyl)-2-oxobutanoic acid
Traditional Name2-oxo-4-thiomethylbutyric acid
CAS Registry Number583-92-6
SMILES
CSCCC(=O)C(O)=O
InChI Identifier
InChI=1S/C5H8O3S/c1-9-3-2-4(6)5(7)8/h2-3H2,1H3,(H,7,8)
InChI KeySXFSQZDSUWACKX-UHFFFAOYSA-N
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
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 | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0g4j-9400000000-16ddd3b5c053991fac9aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f8a-1900000000-ed36a40a48bf904312f4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zir-9700000000-7bbe813aa31ceba0b525JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9100000000-89ba14ad10b374e8daabJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9200000000-b9179ec180a89222c147JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9100000000-63d77e1e6b7bea5353feJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-31b5d7804293c55c928eJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.02 umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02238
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011626
KNApSAcK IDC00007474
Chemspider ID460
KEGG Compound IDC01180
BioCyc IDNot Available
BiGG ID228408
Wikipedia LinkNot Available
METLIN ID6319
PubChem Compound473
PDB IDNot Available
ChEBI ID33574
References
Synthesis ReferenceBrodelius, 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
General References
  1. Martensson J: The occurrence of 4-methylthio-2-hydroxybutyrate in human urine. Anal Biochem. 1986 Apr;154(1):43-9. [PubMed:3706736 ]
  2. 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 ]

Enzymes

General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
Transaminase involved in tyrosine breakdown. Converts tyrosine to p-hydroxyphenylpyruvate. Can catalyze the reverse reaction, using glutamic acid, with 2-oxoglutarate as cosubstrate (in vitro). Has much lower affinity and transaminase activity towards phenylalanine.
Gene Name:
TAT
Uniprot ID:
P17735
Molecular weight:
50398.895
Reactions
2-Oxo-4-methylthiobutanoic acid + L-Glutamic acid → L-Methionine + Oxoglutaric aciddetails
General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Metabolizes the cysteine conjugates of certain halogenated alkenes and alkanes to form reactive metabolites. Catalyzes the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond.
Gene Name:
CCBL1
Uniprot ID:
Q16773
Molecular weight:
47874.765
Reactions
Se-Methylselenocysteine + 2-Oxo-4-methylthiobutanoic acid → Methylselenopyruvate + L-Methioninedetails
General function:
Involved in oxidoreductase activity
Specific function:
Lysosomal L-amino-acid oxidase with highest specific activity with phenylalanine. May play a role in lysosomal antigen processing and presentation (By similarity).
Gene Name:
IL4I1
Uniprot ID:
Q96RQ9
Molecular weight:
65327.26
Reactions
L-Methionine + Water + Oxygen → 2-Oxo-4-methylthiobutanoic acid + Ammonia + Hydrogen peroxidedetails
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). May catalyze the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond (By similarity). Has transaminase activity towards L-kynurenine, tryptophan, phenylalanine, serine, cysteine, methionine, histidine, glutamine and asparagine with glyoxylate as an amino group acceptor (in vitro). Has lower activity with 2-oxoglutarate as amino group acceptor (in vitro) (By similarity).
Gene Name:
CCBL2
Uniprot ID:
Q6YP21
Molecular weight:
51399.855
Reactions
Se-Methylselenocysteine + 2-Oxo-4-methylthiobutanoic acid → Methylselenopyruvate + L-Methioninedetails
General function:
Involved in metal ion binding
Specific function:
Catalyzes the formation of formate and 2-keto-4-methylthiobutyrate (KMTB) from 1,2-dihydroxy-3-keto-5-methylthiopentene (DHK-MTPene). Also down-regulates cell migration mediated by MMP14. Necessary for hepatitis C virus replication in an otherwise non-permissive cell line.
Gene Name:
ADI1
Uniprot ID:
Q9BV57
Molecular weight:
21498.23
Reactions
1,2-Dihydroxy-3-keto-5-methylthiopentene + Oxygen → 2-Oxo-4-methylthiobutanoic acid + Formic aciddetails