Page last updated: 2024-12-04

2-keto-4-methylvalerate

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

Description

alpha-ketoisocaproic acid: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

4-methyl-2-oxopentanoate : A 2-oxo monocarboxylic acid anion that is the conjugate base of 4-methyl-2-oxopentanoic 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]

4-methyl-2-oxopentanoic acid : A 2-oxo monocarboxylic acid that is pentanoic acid (valeric acid) substituted with a keto group at C-2 and a methyl group at C-4. A metabolite that has been found to accumulate in maple syrup urine disease. [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 CID70
CHEMBL ID445647
CHEBI ID48430
SCHEMBL ID43491
MeSH IDM0060555

Synonyms (83)

Synonym
AC-15579
unii-4guj8ah400
einecs 212-435-5
4guj8ah400 ,
.alpha.-ketoisocaproic acid
2-oxo-4-methylpentanoic acid
alpha-oxoisocaproate
2-ketoisocaproic acid
ketoleucine
C00233
2-oxo-4-methylpentanoate
2K-4CH3-PENTANOATE ,
816-66-0
2-oxoisocaproate
4-methyl-2-oxopentanoic acid
4-methyl-2-oxopentanoate
DB03229
alpha-ketoisocaproic acid
4-methyl-2-oxovaleric acid
CHEBI:48430 ,
4-methyl-2-oxovaleric acid, >=98.0% (t)
FC872D44-3E9A-431D-9F84-6FEF64BFEF19
pentanoic acid, 4-methyl-2-oxo-
2-oxoisocaproic acid
isopropylpyruvic acid
BMSE000383
2-oxoisohexanoate
CHEMBL445647 ,
alpha-oxoisohexanoate
K0025
2-keto-4-methylpentanoic acid
methyloxovaleric acid
A840181
NCGC00246997-02
NCGC00246997-01
bdbm50390988
ketoisocaproate
2-oxo-4-methylvaleric acid
alpha-keto-isocaproic acid
2-keto-4-methylvalerate
FT-0619014
4H7Q
AKOS009157216
S2987
gtpl4656
2-oxoleucine
2-keto-4-methylvaleric acid
4-methyl-2-oxo pentanoic acid
4-methyl,2-oxopentanoic acid
4-methyl-2-oxo-pentanoic acid
SCHEMBL43491
4-methyl-2-oxopentanoic acid #
DTXSID6061157
2-methyl-5-oxopentanoic acid
W-104201
a-ketoisocaproic acid
mfcd00066204
|a inverted exclamation mark-ketoisocaproic acid
2-oxo-4-methylvalerate
alpha-ketoisocapronate
a-oxoisocaproate
alpha-keto-isocaproate
ketoisocaproic acid
4-methyl-2-oxo-valerate
4-methyl-2-oxo-valeric acid
oxoisocaproic acid
alpha-ketoisocapronic acid
a-oxoisocaproic acid
a-ketoisocaproate
alpha-oxoisocaproic acid
methyloxovalerate
a-ketoisocapronate
a-ketoisocapronic acid
oxoisocaproate
HY-W012722
CS-W013438
Q622421
STR07443
D82408
4-methyl-2-oxopentanoicacid
4-methyl-2-oxo valeric acid
EN300-182826
Z975823226

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Blood levels in pharmacokinetic and absorption studies are related to the Michaelis-constants."( Enzymatic and pharmacokinetic studies on the metabolism of branched chain alpha-keto acids in the rat.
Bässler, KH; Pietrek, A, 1983
)
0.27

Compound-Compound Interactions

ExcerptReferenceRelevance
" When acetoacetate, beta-hydroxybutyrate, or KIC were combined with MMS, or either ketone body was combined with lactate, insulin release was stimulated 10-fold to 20-fold the controls (almost as much as with glucose)."( Acetoacetate and beta-hydroxybutyrate in combination with other metabolites release insulin from INS-1 cells and provide clues about pathways in insulin secretion.
Brown, LJ; Hasan, NM; Kendrick, MA; Longacre, MJ; MacDonald, MJ; Stoker, SW, 2008
)
0.35

Bioavailability

ExcerptReferenceRelevance
" The enrichment of circulating KICA with [13C]KICA was similar in alcoholics and controls, indicating that a decreased bioavailability or an increased dilution of labeled KICA cannot account for the decreased exhalation of 13CO2."( Mitochondrial function reflected by the decarboxylation of [13C]ketoisocaproate is impaired in alcoholics.
Junker, E; Lauterburg, BH; Meyer, B; Mossi, S; Witschi, A, 1994
)
0.29

Dosage Studied

ExcerptRelevanceReference
" We conclude that at least half of KIC and KIV given orally in this dosage is oxidized in splanchnic organs during first pass but that, nevertheless, these keto acids given orally serve as significant sources of the intracellular amino acids used for protein synthesis in most organs, particularly brain and heart."( Utilization for protein synthesis of leucine and valine compared with their keto analogues.
Shiota, T; Swain, LM; Walser, M, 1990
)
0.28
" Whereas the reduction in Ca2+i was related to the extracellular glucose concentration in a hyperbolic manner, the increasing component exhibited a sigmoidal dose-response relationship."( Nutrient secretagogues induce bimodal early changes in cytoplasmic calcium of insulin-releasing ob/ob mouse beta-cells.
Gylfe, E, 1988
)
0.27
" We also found that alpha-ketoisocaproate feeding at varying dosage did not alter this ratio in whole-body protein (measured in rats fasted overnight), suggesting that neither wide variations in growth rate nor exposure for 10 days to alpha-ketoisocaproate (in a diet of constant protein content) alters the relative rates of utilization (or oxidation) of alpha-ketoisocaproate vs."( Nutritional efficiency of alpha-ketoisocaproate relative to leucine, assessed isotopically.
Kang, CW; Walser, M, 1985
)
0.27
" First, a dose-response study of 12 males (mean age, 16."( Estrogen suppression in males: metabolic effects.
Hayes, V; Klein, KO; Mauras, N; O'Brien, KO, 2000
)
0.31
" KIV elicited clonic convulsions in a dose-response manner, whereas KIC and KMV did not induce seizure-like behavior."( Pharmacological evidence that alpha-ketoisovaleric acid induces convulsions through GABAergic and glutamatergic mechanisms in rats.
Coitinho, AS; de Bastiani, J; de Mello, CF; Fighera, MR; Lima, TT; Wajner, M, 2001
)
0.31
" The optimal dosing of amino acid and energy intake has yet to be established."( Adaptive regulation of amino acid metabolism on early parenteral lipid and high-dose amino acid administration in VLBW infants - a randomized, controlled trial.
Dorst, K; Roelants, JA; Rook, D; Schierbeek, H; van den Akker, CH; van Goudoever, JB; Vermes, A; Vermeulen, MJ; Vlaardingerbroek, H, 2014
)
0.4
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
algal metaboliteAny eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
[role 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]

Drug Classes (2)

ClassDescription
2-oxo monocarboxylic acidAny monocarboxylic acid having a 2-oxo substituent.
branched-chain keto acidAn oxo carboxylic acid in which the parent hydrocarbon chain has one or more alkyl substituents. Derivatives formed from the first step in the metabolism of branched-chain amino acids and can provide important information on animal health and disease.
[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 (27)

PathwayProteinsCompounds
Valine, Leucine, and Isoleucine Degradation2852
beta-Ketothiolase Deficiency2852
2-Methyl-3-hydroxybutyryl-CoA Dehydrogenase Deficiency2852
Propionic Acidemia2852
3-Hydroxy-3-methylglutaryl-CoA Lyase Deficiency2852
Maple Syrup Urine Disease2852
3-Methylcrotonyl-CoA Carboxylase Deficiency Type I2852
3-Methylglutaconic Aciduria Type I2852
3-Methylglutaconic Aciduria Type III2852
Methylmalonate Semialdehyde Dehydrogenase Deficiency2852
Methylmalonic Aciduria2852
Isovaleric Aciduria2852
3-Methylglutaconic Aciduria Type IV2852
3-Hydroxyisobutyric Acid Dehydrogenase Deficiency2852
3-Hydroxyisobutyric Aciduria2852
Isobutyryl-CoA Dehydrogenase Deficiency2852
Isovaleric Acidemia2852
Leucine Biosynthesis816
Secondary Metabolites: Valine and L-Leucine Biosynthesis from Pyruvate1024
Secondary Metabolites: Leucine Biosynthesis716
Leucine Degradation610
2-Methyl-3-hydroxybutryl-CoA Dehydrogenase Deficiency2952
Valine,Leucine and Isoleucine degradation ( Valine,Leucine and Isoleucine degradation )2936
2-Oxo-glutaric acid + L-Leucine = L-Glutamic acid + 4-Methyl-2-oxo-pentanoic acid ( Valine,Leucine and Isoleucine degradation )24
Glucosinolate biosynthesis from branched-chain amino acid012
Valine, leucine and isoleucine degradation034
Biochemical pathways: part I0466

Protein Targets (3)

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)
Monocarboxylate transporter 1Rattus norvegicus (Norway rat)Km670.00002.28002.66503.0500AID681605
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (4)

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)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

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)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

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)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (4)

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.
AID679841TP_TRANSPORTER: inhibition of lactate uptake (Lactate:0.1mM, alpha-Ketoisocaproate:5mM, preincubation with aminoxyacetate) in Xenopus laevis oocytes1997The Journal of biological chemistry, Nov-28, Volume: 272, Issue:48
Comparison of lactate transport in astroglial cells and monocarboxylate transporter 1 (MCT 1) expressing Xenopus laevis oocytes. Expression of two different monocarboxylate transporters in astroglial cells and neurons.
AID681605TP_TRANSPORTER: change in intracellular pH(pHi)value in Xenopus laevis oocytes1998The Biochemical journal, Jul-01, Volume: 333 ( Pt 1)Characterization of the monocarboxylate transporter 1 expressed in Xenopus laevis oocytes by changes in cytosolic pH.
AID681123TP_TRANSPORTER: inhibition of lactate uptake in Xenopus laevis oocytes1999The Biochemical journal, Aug-01, Volume: 341 ( Pt 3)Characterization of the high-affinity monocarboxylate transporter MCT2 in Xenopus laevis oocytes.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (718)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990269 (37.47)18.7374
1990's230 (32.03)18.2507
2000's132 (18.38)29.6817
2010's77 (10.72)24.3611
2020's10 (1.39)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 7.65

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index7.65 (24.57)
Research Supply Index6.67 (2.92)
Research Growth Index4.32 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (7.65)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials52 (7.05%)5.53%
Reviews21 (2.85%)6.00%
Case Studies3 (0.41%)4.05%
Observational0 (0.00%)0.25%
Other662 (89.70%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]