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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:47 UTC

HMDB ID

HMDB0001553

Secondary Accession Numbers

HMDB0013210
HMDB01553
HMDB13210

Metabolite Identification

Common Name

2-Oxo-4-methylthiobutanoic acid

Description

2-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Keto-4-methylthiobutyric acid	ChEBI
2-oxo-4-Methylthiobutanoate	ChEBI
2-Oxomethionine	ChEBI
4-(METHYLsulfanyl)-2-oxobutanoIC ACID	ChEBI
4-Methylthio-2-oxobutanoate	ChEBI
alpha-oxo-gamma-Methylthiobutyric acid	ChEBI
4-(Methylsulfanyl)-2-oxobutanoate	Kegg
2-Keto-4-methylthiobutyrate	Generator
4-(METHYLsulphanyl)-2-oxobutanoate	Generator
4-(METHYLsulphanyl)-2-oxobutanoic acid	Generator
4-Methylthio-2-oxobutanoic acid	Generator
a-oxo-g-Methylthiobutyrate	Generator
a-oxo-g-Methylthiobutyric acid	Generator
alpha-oxo-gamma-Methylthiobutyrate	Generator
Α-oxo-γ-methylthiobutyrate	Generator
Α-oxo-γ-methylthiobutyric acid	Generator
2-Ketomethiobutyrate	HMDB
4-Methylthio-2-ketobutanoate	HMDB
4-Methylthio-2-ketobutanoic acid	HMDB
4-Methylthio-2-ketobutyrate	HMDB
4-Methylthio-2-oxobutyrate	HMDB
alpha-Keto-methiolbutyric acid	HMDB
Keto-4-methylthiobutyrate	HMDB
Ketomethiobutyrate	HMDB
Ketomethiobutyric acid	HMDB
KMTB	HMDB
Methylthiobutyrate	HMDB
Methylthiobutyric acid	HMDB
2-Keto-4-methylthiobutanoic acid	HMDB
2-Keto-4-thiomethylbutyrate	HMDB
2-oxo-4-Thiomethylbutyric acid	HMDB
alpha-Keto-gamma-methiolbutyrate	HMDB
alpha-Ketomethionine	HMDB
alpha-Oxomethionine	HMDB
2-Keto-4-methylthiobutyric acid, monosodium salt	HMDB
2-Ketothiomethylbutyric acid	HMDB
4-Methylthio-2-oxobutyric acid	HMDB
S-Methyl-alpha-ketobutyric acid	HMDB
2-Keto-4-methylthiobutyric acid, calcium salt	HMDB
4-Methylthio-2-ketobutyric acid	HMDB
gamma-Methiol-keto-butyric acid	HMDB
4-Methylmercapto-2-oxobutyrate	HMDB
2-oxo-4-Methylthiobutanoic acid	KEGG

Chemical Formula

C₅H₈O₃S

Average Molecular Weight

148.18

Monoisotopic Molecular Weight

148.019414812

IUPAC Name

4-(methylsulfanyl)-2-oxobutanoic acid

Traditional Name

2-oxo-4-thiomethylbutyric acid

CAS Registry Number

583-92-6

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 Key

SXFSQZDSUWACKX-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

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

2-oxo monocarboxylic acid (CHEBI:33574 )
sulfur-containing carboxylic acid (CHEBI:33574 )
Oxo fatty acids (C01180 )
Oxo fatty acids (LMFA01060170 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.44 g/L	ALOGPS
logP	-0.07	ALOGPS
logP	1.12	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	3.3	ChemAxon
pKa (Strongest Basic)	-9.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	35.07 m³·mol⁻¹	ChemAxon
Polarizability	14.21 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	131.392	31661259
DarkChem	[M-H]-	126.805	31661259
AllCCS	[M+H]+	131.935	32859911
AllCCS	[M-H]-	133.529	32859911
DeepCCS	[M+H]+	131.045	30932474
DeepCCS	[M-H]-	128.28	30932474
DeepCCS	[M-2H]-	164.726	30932474
DeepCCS	[M+Na]+	139.525	30932474
AllCCS	[M+H]+	131.9	32859911
AllCCS	[M+H-H2O]+	128.0	32859911
AllCCS	[M+NH4]+	135.6	32859911
AllCCS	[M+Na]+	136.7	32859911
AllCCS	[M-H]-	133.5	32859911
AllCCS	[M+Na-2H]-	136.2	32859911
AllCCS	[M+HCOO]-	139.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.62 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6611 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.58 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	59.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1384.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	363.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	102.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	244.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	101.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	341.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	473.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	130.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	851.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	303.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	956.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	267.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	330.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	439.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	284.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	122.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Oxo-4-methylthiobutanoic acid	CSCCC(=O)C(O)=O	2267.1	Standard polar	33892256
2-Oxo-4-methylthiobutanoic acid	CSCCC(=O)C(O)=O	1323.8	Standard non polar	33892256
2-Oxo-4-methylthiobutanoic acid	CSCCC(=O)C(O)=O	1245.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Oxo-4-methylthiobutanoic acid,1TMS,isomer #1	CSCCC(=O)C(=O)O[Si](C)(C)C	1362.1	Semi standard non polar	33892256
2-Oxo-4-methylthiobutanoic acid,1TMS,isomer #2	CSCC=C(O[Si](C)(C)C)C(=O)O	1461.5	Semi standard non polar	33892256
2-Oxo-4-methylthiobutanoic acid,2TMS,isomer #1	CSCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1505.4	Semi standard non polar	33892256
2-Oxo-4-methylthiobutanoic acid,2TMS,isomer #1	CSCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1466.5	Standard non polar	33892256
2-Oxo-4-methylthiobutanoic acid,2TMS,isomer #1	CSCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1638.6	Standard polar	33892256
2-Oxo-4-methylthiobutanoic acid,1TBDMS,isomer #1	CSCCC(=O)C(=O)O[Si](C)(C)C(C)(C)C	1609.3	Semi standard non polar	33892256
2-Oxo-4-methylthiobutanoic acid,1TBDMS,isomer #2	CSCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O	1699.0	Semi standard non polar	33892256
2-Oxo-4-methylthiobutanoic acid,2TBDMS,isomer #1	CSCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1972.1	Semi standard non polar	33892256
2-Oxo-4-methylthiobutanoic acid,2TBDMS,isomer #1	CSCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1880.3	Standard non polar	33892256
2-Oxo-4-methylthiobutanoic acid,2TBDMS,isomer #1	CSCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1910.7	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Feces
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Methionine Metabolism
Cystathionine Beta-Synthase Deficiency		Not Available
Hypermethioninemia		Not Available
S-Adenosylhomocysteine (SAH) Hydrolase Deficiency		Not Available
Glycine N-methyltransferase Deficiency		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	0.02 umol/mmol creatinine	Children (1-13 years old)	Both	Normal	Geigy Scientific ...	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB02238

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

6319

PubChem Compound

473

PDB ID

Not Available

ChEBI ID

33574

Food Biomarker Ontology

Not Available

VMH ID

2KMB

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

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

General References

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 ]

Enzymes

Enzyme Details

1. Tyrosine aminotransferase

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 + Glutamic acid → Methionine + Oxoglutaric acid	details

Enzyme Details

2. Kynurenine--oxoglutarate transaminase 1

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 + Methionine	details

Enzyme Details

3. L-amino-acid oxidase

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

Methionine + Water + Oxygen → 2-Oxo-4-methylthiobutanoic acid + Ammonia + Hydrogen peroxide	details

Enzyme Details

4. Kynurenine--oxoglutarate transaminase 3

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 + Methionine	details

Enzyme Details

5. 1,2-dihydroxy-3-keto-5-methylthiopentene dioxygenase

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 acid	details

Showing metabocard for 2-Oxo-4-methylthiobutanoic acid (HMDB0001553)

MOL for HMDB0001553 (2-Oxo-4-methylthiobutanoic acid)

3D MOL for HMDB0001553 (2-Oxo-4-methylthiobutanoic acid)

3D SDF for HMDB0001553 (2-Oxo-4-methylthiobutanoic acid)

3D-SDF for HMDB0001553 (2-Oxo-4-methylthiobutanoic acid)

PDB for HMDB0001553 (2-Oxo-4-methylthiobutanoic acid)

3D PDB for HMDB0001553 (2-Oxo-4-methylthiobutanoic acid)

SMILES for HMDB0001553 (2-Oxo-4-methylthiobutanoic acid)

INCHI for HMDB0001553 (2-Oxo-4-methylthiobutanoic acid)

Structure for HMDB0001553 (2-Oxo-4-methylthiobutanoic acid)

3D Structure for HMDB0001553 (2-Oxo-4-methylthiobutanoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions