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Details

Stereochemistry ACHIRAL
Molecular Formula C5H8O3
Molecular Weight 116.1152
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 3-METHYL-2-OXOBUTYRIC ACID

SMILES

CC(C)C(=O)C(O)=O

InChI

InChIKey=QHKABHOOEWYVLI-UHFFFAOYSA-N
InChI=1S/C5H8O3/c1-3(2)4(6)5(7)8/h3H,1-2H3,(H,7,8)

HIDE SMILES / InChI

Approval Year

PubMed

PubMed

TitleDatePubMed
Channeling of substrates and intermediates in enzyme-catalyzed reactions.
2001
Effect of starvation on branched-chain alpha-keto acid dehydrogenase activity in rat heart and skeletal muscle.
2001
Psychrophilic valine dehydrogenase of the antarctic psychrophile, Cytophaga sp. KUC-1: purification, molecular characterization and expression.
2001 Aug
Regulation of the activity of branched-chain 2-oxo acid dehydrogenase (BCODH) complex by binding BCODH kinase.
2001 Feb 23
Carrier detection and rapid newborn diagnostic test for the common Y393N maple syrup urine disease allele by PCR-RFLP: culturally permissible testing in the Mennonite community.
2001 Jun
A gene controlling variation in Arabidopsis glucosinolate composition is part of the methionine chain elongation pathway.
2001 Nov
Uteroplacental insufficiency alters liver and skeletal muscle branched-chain amino acid metabolism in intrauterine growth-restricted fetal rats.
2001 Nov
A trail of research from lipoic acid to alpha-keto acid dehydrogenase complexes.
2001 Oct 19
Natural osmolyte trimethylamine N-oxide corrects assembly defects of mutant branched-chain alpha-ketoacid decarboxylase in maple syrup urine disease.
2001 Oct 26
Nitrogen source governs the patterns of growth and pristinamycin production in 'Streptomyces pristinaespiralis'.
2001 Sep
Biochemical basis of type IB (E1beta ) mutations in maple syrup urine disease. A prevalent allele in patients from the Druze kindred in Israel.
2001 Sep 28
Recurrent intragenomic recombination leading to sequence homogenization during the evolution of the lipoyl-binding domain.
2002 Apr 9
Evidence of common ancestry for the maple syrup urine disease (MSUD) Y438N allele in non-Mennonite MSUD patients.
2002 Jan
Effect of the branched-chain alpha-ketoacids accumulating in maple syrup urine disease on the high molecular weight neurofilament subunit (NF-H) in rat cerebral cortex.
2002 Jun
Diagnosis and treatment of maple syrup disease: a study of 36 patients.
2002 Jun
Primary biliary cirrhosis: seeking the silent partner of autoimmunity.
2002 Jun
Clinical significance of positive immunoblotting but negative immunofluorescence for antimitochondrial antibodies in patients with liver diseases other than primary biliary cirrhosis.
2002 Mar
Activation of the promoters of Arabidopsis genes for the branched-chain alpha-keto acid dehydrogenase complex in transgenic tobacco BY-2 cells under sugar starvation.
2002 Mar
Maple syrup urine disease: mutation analysis in Turkish patients.
2002 May
Solution structure and dynamics of the lipoic acid-bearing domain of human mitochondrial branched-chain alpha-keto acid dehydrogenase complex.
2002 May 3
Tissue-specific effects of chronic dietary leucine and norleucine supplementation on protein synthesis in rats.
2002 Oct
The C-terminal hinge region of lipoic acid-bearing domain of E2b is essential for domain interaction with branched-chain alpha-keto acid dehydrogenase kinase.
2002 Oct 4
Evolution of mosaic operons by horizontal gene transfer and gene displacement in situ.
2003
The genomics and proteomics of biofilm formation.
2003
Dietary carbohydrate deprivation increases 24-hour nitrogen excretion without affecting postabsorptive hepatic or whole body protein metabolism in healthy men.
2003 Aug
Structure of E. coli ketopantoate hydroxymethyl transferase complexed with ketopantoate and Mg2+, solved by locating 160 selenomethionine sites.
2003 Aug
Reaction of 1-amino-2-methylenecyclopropane-1-carboxylate with 1-aminocyclopropane-1-carboxylate deaminase: analysis and mechanistic implications.
2003 Feb 25
Mycobacterium tuberculosis ketopantoate hydroxymethyltransferase: tetrahydrofolate-independent hydroxymethyltransferase and enolization reactions with alpha-keto acids.
2003 Jan 14
Identification of twelve novel mutations in patients with classic and variant forms of maple syrup urine disease.
2003 Nov
Protein components of mitochondrial DNA nucleoids in higher eukaryotes.
2003 Nov
Ile, Leu, and Val methyl assignments of the 723-residue malate synthase G using a new labeling strategy and novel NMR methods.
2003 Nov 12
Premorbid weight, body mass, and varsity athletics in ALS.
2003 Oct 14
Roles of His291-alpha and His146-beta' in the reductive acylation reaction catalyzed by human branched-chain alpha-ketoacid dehydrogenase: refined phosphorylation loop structure in the active site.
2003 Oct 31
Substrate specificity and kinetic isotope effect analysis of the Eschericia coli ketopantoate reductase.
2003 Sep 30
A simple and rapid enzymatic assay for the branched-chain alpha-ketoacid dehydrogenase complex using high-performance liquid chromatography.
2004
Catabolism of leucine to branched-chain fatty acids in Staphylococcus xylosus.
2004
Diversity of L-leucine catabolism in various microorganisms involved in dairy fermentations, and identification of the rate-controlling step in the formation of the potent flavour component 3-methylbutanal.
2004 Apr
Ligand-induced conformational changes and a reaction intermediate in branched-chain 2-oxo acid dehydrogenase (E1) from Thermus thermophilus HB8, as revealed by X-ray crystallography.
2004 Apr 2
Lipoic acid-dependent oxidative catabolism of alpha-keto acids in mitochondria provides evidence for branched-chain amino acid catabolism in Arabidopsis.
2004 Feb
Branched-chain amino acid catabolism: unique segregation of pathway enzymes in organ systems and peripheral nerves.
2004 Jan
Mechanisms responsible for regulation of branched-chain amino acid catabolism.
2004 Jan 9
Protein requirements for endurance athletes.
2004 Jul-Aug
Leucine toxicity in a neuronal cell model with inhibited branched chain amino acid catabolism.
2004 Mar 30
Glutamine synthesis in the developing porcine placenta.
2004 May
Conformational stability and thermodynamic characterization of the lipoic acid bearing domain of human mitochondrial branched chain alpha-ketoacid dehydrogenase.
2004 Sep
Precursor and temperature modulation of fatty acid composition and growth of Listeria monocytogenes cold-sensitive mutants with transposon-interrupted branched-chain alpha-keto acid dehydrogenase.
2005 Feb
The mitochondrial branched-chain aminotransferase (AtBCAT-1) is capable to initiate degradation of leucine, isoleucine and valine in almost all tissues in Arabidopsis thaliana.
2005 Jan
Thermococcus profundus 2-ketoisovalerate ferredoxin oxidoreductase, a key enzyme in the archaeal energy-producing amino acid metabolic pathway.
2005 Jan
A comprehensive update of the sequence and structure classification of kinases.
2005 Mar 16
Activation of hepatic branched-chain alpha-keto acid dehydrogenase complex by tumor necrosis factor-alpha in rats.
2005 Mar 25
Name Type Language
3-METHYL-2-OXOBUTYRIC ACID
Systematic Name English
DIMETHYLPYRUVIC ACID
Systematic Name English
ISOPROPYLGLYOXYLIC ACID
Systematic Name English
3-METHYL-2-OXO BUTANOIC ACID
Systematic Name English
BUTANOIC ACID, 3-METHYL-2-OXO-
Common Name English
FEMA NO. 3869, ACID-
Code English
ALPHA-KETO-VALINE
Common Name English
.ALPHA.-KETOISOVALERIC ACID
Systematic Name English
.ALPHA.-KETO-ISOVALERIC ACID
Systematic Name English
2-OXOISOVALERIC ACID
Systematic Name English
2-KETO-3-METHYLBUTYRIC ACID
Systematic Name English
2-OXO-3-METHYLBUTYRIC ACID
Systematic Name English
KETOVALINE
Systematic Name English
.ALPHA.-OXOISOVALERIC ACID
Systematic Name English
3-METHYL-2-OXOBUTANOIC ACID [FHFI]
Common Name English
2-KETOISOVALERIC ACID
Systematic Name English
2-OXO-ISOVALERIC ACID
Systematic Name English
2-OXO-3-METHYLBUTANOIC ACID
Systematic Name English
.ALPHA.-OXO-.BETA.-METHYLBUTYRIC ACID
Systematic Name English
Classification Tree Code System Code
JECFA EVALUATION 3-METHYL-2-OXOBUTANOIC ACID
Created by admin on Fri Dec 15 15:18:59 GMT 2023 , Edited by admin on Fri Dec 15 15:18:59 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID6061078
Created by admin on Fri Dec 15 15:18:59 GMT 2023 , Edited by admin on Fri Dec 15 15:18:59 GMT 2023
PRIMARY
CAS
759-05-7
Created by admin on Fri Dec 15 15:18:59 GMT 2023 , Edited by admin on Fri Dec 15 15:18:59 GMT 2023
PRIMARY
PUBCHEM
49
Created by admin on Fri Dec 15 15:18:59 GMT 2023 , Edited by admin on Fri Dec 15 15:18:59 GMT 2023
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JECFA MONOGRAPH
460
Created by admin on Fri Dec 15 15:18:59 GMT 2023 , Edited by admin on Fri Dec 15 15:18:59 GMT 2023
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CHEBI
16530
Created by admin on Fri Dec 15 15:18:59 GMT 2023 , Edited by admin on Fri Dec 15 15:18:59 GMT 2023
PRIMARY
WIKIPEDIA
alpha-Ketoisovaleric acid
Created by admin on Fri Dec 15 15:18:59 GMT 2023 , Edited by admin on Fri Dec 15 15:18:59 GMT 2023
PRIMARY
ECHA (EC/EINECS)
212-065-4
Created by admin on Fri Dec 15 15:18:59 GMT 2023 , Edited by admin on Fri Dec 15 15:18:59 GMT 2023
PRIMARY
FDA UNII
34P71D50E0
Created by admin on Fri Dec 15 15:18:59 GMT 2023 , Edited by admin on Fri Dec 15 15:18:59 GMT 2023
PRIMARY
DRUG BANK
DB04074
Created by admin on Fri Dec 15 15:18:59 GMT 2023 , Edited by admin on Fri Dec 15 15:18:59 GMT 2023
PRIMARY