Page last updated: 2024-12-04

alpha-ketobutyric acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Alpha-ketobutyric acid (α-KBA) is a four-carbon α-keto acid that plays a role in various metabolic pathways. It is an intermediate in the metabolism of isoleucine, threonine, and methionine. α-KBA is synthesized through the deamination of L-threonine by threonine dehydratase. It can also be produced from the oxidation of α-hydroxybutyrate by the enzyme lactate dehydrogenase. α-KBA is involved in the biosynthesis of valine and leucine, and it is a precursor for the synthesis of the neurotransmitter GABA. Research on α-KBA focuses on its potential role in various diseases, including diabetes, cancer, and neurodegenerative disorders. Elevated levels of α-KBA have been associated with diabetes and insulin resistance. Some studies suggest that α-KBA may have anti-cancer properties, while others have linked it to increased risk of certain types of cancer. α-KBA is also being investigated for its potential as a therapeutic agent for Alzheimer's disease and other neurodegenerative disorders. The study of α-KBA is important due to its involvement in key metabolic pathways and its potential link to various diseases.'
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alpha-ketobutyric acid: RN given refers to parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

2-oxobutanoic acid : A 2-oxo monocarboxylic acid that is the 2-oxo derivative of butanoic acid. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID58
CHEMBL ID171246
CHEBI ID30831
SCHEMBL ID24128
MeSH IDM0046407

Synonyms (95)

Synonym
3-methyl pyruvic acid
2-ketobutanoic acid
CHEBI:30831 ,
alpha-oxo-n-butyric acid
.alpha.-ketobutyric acid
nsc60533
.alpha.-ketobutric acid
.alpha.-oxobutyrate
.alpha.-oxo-n-butyric acid
pyruvic acid, methyl-
formic acid, propionyl-
butanoic acid, 2-oxo-
.alpha.-oxobutyric acid
nsc-60533
butyric acid, 2-oxo-
ketobutyrate
alpha-keto-n-butyric acid
fema no. 3723
butyric acid, 2-oxo- (8ci)
3-methylpyruvic acid
butanoic acid, 2-oxo- (9ci)
2-oxo-n-butyric acid
propionylformic acid
2-oxobutyrate
2-oxobutyric acid
2-keto-butyrate
alpha-ketobutyric acid
2-ketobutyric acid
2-oxobutanoic acid
C00109
alpha-oxobutyric acid
600-18-0
2-oxo-butyrate
2-ketobutyric acid, 97%
2-oxobutyric acid, >=95%, fg
DB04553
2-oxo-butanoic acid
2KT ,
LMFA01060002
K-1650
35DB7B81-3F44-4D6F-9E8B-C0F8B751D3AD
O0364
BMSE000325
CHEMBL171246
2-oxo-butyric acid
AKOS005207091
unii-b92rb6hy1a
einecs 209-986-9
b92rb6hy1a ,
alpha-ketobutric acid
nsc 60533
FT-0612731
4B5T
S6329
methyl pyruvic acid
oxobutyric acid
2-keto-butyric acid
AM90224
SCHEMBL24128
.alpha.-oxobutanoic acid
2-oxobutyric acid [fhfi]
.alpha.-keto-n-butyric acid
2-oxobutanoic acid #
alpha-oxobutanoic acid
DTXSID9060524
CS-W007926
2-oxobutyric acid, purum, >=97.0% (t)
mfcd00004164
2-oxobutyric acid, analytical standard
3-methylpyruvate
a-ketobutyrate
a-oxobutyric acid
a-oxo-n-butyrate
a-keto-n-butyrate
a-oxobutyrate
propionyl-formate
2-oxo-butanoate
propionyl-formic acid
2-oxo-n-butyrate
a-keto-n-butyric acid
alpha-oxo-n-butyrate
alpha-keto-n-butyrate
a-oxo-n-butyric acid
methyl-pyruvic acid
HY-W007926
DS-14641
Q209457
2-oxobutanoicacid
SY011034
O10846
A904502
?-ketobutyric acid
PB43133
AC-37023
PD006009

Research Excerpts

Compound-Compound Interactions

ExcerptReferenceRelevance
" YILWΔalaTpXMJ19thrABC exhibited a cumulative reduction of these by-products excretion, which indicated that thrABC overexpression combined with alaT deletion resulted in the metabolic flux redistribution from 2-ketobutyrate and pyruvate to L-isoleucine synthesis, and decreased the fluxes to by-products synthesis accordingly."( Enhancing (L)-isoleucine production by thrABC overexpression combined with alaT deletion in Corynebacterium glutamicum.
Chen, N; Wang, J; Wen, B; Xie, X; Xu, Q; Zhang, C, 2013
)
0.39

Dosage Studied

ExcerptRelevanceReference
" In an in vivo experiment using mice treated with PAD before a toxic dosage of SeMet, the amount of SeMet in the liver decreased and the amount of acid-volatile Se derived from CH(3)SeH increased gradually."( Contribution of enzymic alpha, gamma-elimination reaction in detoxification pathway of selenomethionine in mouse liver.
Kubota, T; Kuroda, T; Nakamuro, K; Okuno, T; Ueno, H, 2001
)
0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
2-oxo monocarboxylic acidAny monocarboxylic acid having a 2-oxo substituent.
short-chain fatty acidAn aliphatic monocarboxylic acid with a chain length of less than C6. If any non-hydrocarbon substituent is present, the compound is not normally regarded as a short-chain fatty acid.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (48)

PathwayProteinsCompounds
Metabolism14961108
Amino acid and derivative metabolism250260
Sulfur amino acid metabolism2763
Cysteine formation from homocysteine28
Degradation of cysteine and homocysteine1538
Selenoamino acid metabolism2450
Metabolism of ingested SeMet, Sec, MeSec into H2Se423
Threonine catabolism514
Selenoamino Acid Metabolism1226
Glycine and Serine Metabolism2452
Propanoate Metabolism1837
Methionine Metabolism1637
Threonine and 2-Oxobutanoate Degradation814
Homocysteine Degradation27
Cystathionine beta-Synthase Deficiency1637
Hypermethioninemia1637
S-Adenosylhomocysteine (SAH) Hydrolase Deficiency1637
Glycine N-Methyltransferase Deficiency1637
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)1637
Methionine Adenosyltransferase Deficiency1637
Dimethylglycine Dehydrogenase Deficiency2452
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)2452
Sarcosinemia2452
Malonic Aciduria1837
Methylmalonic Aciduria Due to Cobalamin-Related Disorders1837
Non-Ketotic Hyperglycinemia2452
Hyperglycinemia, Non-Ketotic2452
Malonyl-CoA Decarboxylase Deficiency1837
gamma-Cystathionase Deficiency (CTH)27
Homocystinuria, Cystathionine beta-Synthase Deficiency27
Homocystinuria-Megaloblastic Anemia Due to Defect in Cobalamin Metabolism, cblG Complementation Type1637
3-Phosphoglycerate Dehydrogenase Deficiency2452
Isoleucine Biosynthesis1622
Methionine Metabolism and Salvage1534
Selenocompound Metabolism923
C5-Branched Dibasic Acid Metabolism511
Glycine and Serine metabolism ( Glycine and Serine metabolism )3649
Methionine and Cysteine metabolism ( Methionine and Cysteine metabolism )2342
Propanoate metabolism ( Propanoate metabolism )2222
NAD+ + 2-Hydroxy-butanoic acid = NADH + 2-Oxo-butanoic acid ( Propanoate metabolism )44
Metabolic Epileptic Disorders2589
Mycobacterium tuberculosis biological processes3962
Sulfur compound metabolism1929
cysteine and homocysteine interconversion09
Folic acid network070
Cysteine biosynthesis from homoserine02
Biochemical pathways: part I0466
Amino acid metabolism094
Isoleucine biosynthesis from threonine215

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (8)

Processvia Protein(s)Taxonomy
lactate transmembrane transportMonocarboxylate transporter 4Homo sapiens (human)
pyruvate catabolic processMonocarboxylate transporter 4Homo sapiens (human)
pyruvate transmembrane transportMonocarboxylate transporter 4Homo sapiens (human)
monocarboxylic acid transportMonocarboxylate transporter 4Homo sapiens (human)
diaminopimelate biosynthetic process4-hydroxy-tetrahydrodipicolinate synthaseEscherichia coli K-12
lysine biosynthetic process4-hydroxy-tetrahydrodipicolinate synthaseEscherichia coli K-12
lysine biosynthetic process via diaminopimelate4-hydroxy-tetrahydrodipicolinate synthaseEscherichia coli K-12
diaminopimelate biosynthetic process4-hydroxy-tetrahydrodipicolinate synthaseEscherichia coli K-12
small molecule metabolic process4-hydroxy-tetrahydrodipicolinate synthaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
RNA bindingMonocarboxylate transporter 4Homo sapiens (human)
protein bindingMonocarboxylate transporter 4Homo sapiens (human)
monocarboxylic acid transmembrane transporter activityMonocarboxylate transporter 4Homo sapiens (human)
lactate:proton symporter activityMonocarboxylate transporter 4Homo sapiens (human)
pyruvate transmembrane transporter activityMonocarboxylate transporter 4Homo sapiens (human)
4-hydroxy-tetrahydrodipicolinate synthase activity4-hydroxy-tetrahydrodipicolinate synthaseEscherichia coli K-12
lyase activity4-hydroxy-tetrahydrodipicolinate synthaseEscherichia coli K-12
identical protein binding4-hydroxy-tetrahydrodipicolinate synthaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
plasma membraneMonocarboxylate transporter 4Homo sapiens (human)
membraneMonocarboxylate transporter 4Homo sapiens (human)
basolateral plasma membraneMonocarboxylate transporter 4Homo sapiens (human)
apical plasma membraneMonocarboxylate transporter 4Homo sapiens (human)
lateral plasma membraneMonocarboxylate transporter 4Homo sapiens (human)
nuclear membraneMonocarboxylate transporter 4Homo sapiens (human)
plasma membraneMonocarboxylate transporter 4Homo sapiens (human)
basolateral plasma membraneMonocarboxylate transporter 4Homo sapiens (human)
cytoplasm4-hydroxy-tetrahydrodipicolinate synthaseEscherichia coli K-12
cytosol4-hydroxy-tetrahydrodipicolinate synthaseEscherichia coli K-12
cytosol4-hydroxy-tetrahydrodipicolinate synthaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID681140TP_TRANSPORTER: uptake in Xenopus laevis oocytes2000The Journal of physiology, Dec-01, Volume: 529 Pt 2Characterisation of human monocarboxylate transporter 4 substantiates its role in lactic acid efflux from skeletal muscle.
AID388791Inhibition of Escherichia coli DHDPS2008Bioorganic & medicinal chemistry, Dec-01, Volume: 16, Issue:23
Irreversible inhibition of dihydrodipicolinate synthase by 4-oxo-heptenedioic acid analogues.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2012The Journal of biological chemistry, Oct-19, Volume: 287, Issue:43
Crystal structure of reaction intermediates in pyruvate class II aldolase: substrate cleavage, enolate stabilization, and substrate specificity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (142)

TimeframeStudies, This Drug (%)All Drugs %
pre-199045 (31.69)18.7374
1990's21 (14.79)18.2507
2000's34 (23.94)29.6817
2010's35 (24.65)24.3611
2020's7 (4.93)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 38.43

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index38.43 (24.57)
Research Supply Index4.98 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index54.53 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (38.43)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.69%)5.53%
Reviews1 (0.69%)6.00%
Case Studies1 (0.69%)4.05%
Observational0 (0.00%)0.25%
Other141 (97.92%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]