.ALPHA.-KETOISOCAPROIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H10O3
Molecular Weight	130.1418
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of .ALPHA.-KETOISOCAPROIC ACID

Structure Search

SMILES

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

InChI

InChIKey=BKAJNAXTPSGJCU-UHFFFAOYSA-N

InChI=1S/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)

HIDE SMILES / InChI

Molecular Formula	C6H10O3
Molecular Weight	130.1418
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Supplementing with beta-hydroxy-beta-methylbutyrate (HMB) to build and maintain muscle mass: a review.	2002	14632320
Insulin secretion induced by palmitate--a process fully dependent on glucose concentration.	2002 Dec	12688632
Kinetics of sequential metabolism from D-leucine to L-leucine via alpha-ketoisocaproic acid in rat.	2002 Dec	12433816
Role of blood cells in leucine kinetics across the human kidney.	2002 Dec	12388393
alpha-Ketoisocaproic acid regulates phosphorylation of intermediate filaments in postnatal rat cortical slices through ionotropic glutamatergic receptors.	2002 Dec 15	12480141
Leucine promotes glucose uptake in skeletal muscles of rats.	2002 Dec 20	12470633
Effect of supply of metabolizable protein on whole body and splanchnic leucine metabolism in lactating dairy cows.	2002 Oct	12416817
In vivo assessment of the mitochondrial response to caloric restriction in obese women by the 2-keto[1-C]isocaproate breath test.	2003 Apr	12701059
Development of a capillary electrophoretic method for the analysis of amino acids containing tablets.	2003 Apr 18	12735449
Acute effects of acidosis on protein and amino acid metabolism in perfused rat liver.	2003 Aug	14632632
Methodological characterization of the 2-keto [1-13C]isocaproate breath test to measure in vivo human mitochondrial function: application in alcoholic liver disease assessment.	2003 Aug	12966324
Synergistic effects of testosterone and growth hormone on protein metabolism and body composition in prepubertal boys.	2003 Aug	12898459
Metabolism of brain amino acids following pentylenetetrazole treatment.	2003 Feb	12576176
Disturbance of cultured rat neuronal network activity depends on concentration and ratio of leucine and alpha-ketoisocaproate: implication for acute encephalopathy of maple syrup urine disease.	2003 Feb	12538793
Effect of minimal enteral feeding on splanchnic uptake of leucine in the postabsorptive state in preterm infants.	2003 Feb	12538787
Mycobacterium tuberculosis ketopantoate hydroxymethyltransferase: tetrahydrofolate-independent hydroxymethyltransferase and enolization reactions with alpha-keto acids.	2003 Jan 14	12515554
Human mitochondrial and cytosolic branched-chain aminotransferases are cysteine S-conjugate beta-lyases, but turnover leads to inactivation.	2003 Jan 15	12504794
Characterization of homoisocitrate dehydrogenase involved in lysine biosynthesis of an extremely thermophilic bacterium, Thermus thermophilus HB27, and evolutionary implication of beta-decarboxylating dehydrogenase.	2003 Jan 17	12427751
Regulation of leucine-stimulated insulin secretion and glutamine metabolism in isolated rat islets.	2003 Jan 31	12444083
Effects of fatty acids on hepatic amino acid catabolism and fibrinogen synthesis in young healthy volunteers.	2003 Jul	12791602
Allosteric activators of glucokinase: potential role in diabetes therapy.	2003 Jul 18	12869762
Opposite effects of glucose on plasma membrane Ca2+-ATPase and Na/Ca exchanger transcription, expression, and activity in rat pancreatic beta-cells.	2003 Jun 20	12682074
Effects of environmental factors on leucine catabolism by Carnobacterium piscicola.	2003 Mar 25	12485743
A 48-hour exposure of pancreatic islets to calpain inhibitors impairs mitochondrial fuel metabolism and the exocytosis of insulin.	2003 May	12759879
Oxidation of essential amino acids by the ovine gastrointestinal tract.	2003 May	12720582
Distinguishing features of leucine and alpha-ketoisocaproate sensing in pancreatic beta-cells.	2003 May	12697702
Model to assess muscle protein turnover: domain of validity using amino acyl-tRNA vs. surrogate measures of precursor pool.	2003 Nov	14534080
Quantitation of endogenous analytes in biofluid without a true blank matrix.	2003 Nov 1	14588026
Inhibition of brain energy metabolism by the alpha-keto acids accumulating in maple syrup urine disease.	2003 Nov 20	14636955
Pyruvate inhibits zinc-mediated pancreatic islet cell death and diabetes.	2003 Sep	12898018
Gender differences in the regulation of amino acid metabolism.	2003 Sep	12807899
Expression of monocarboxylic acid transporters (MCT) in brain cells. Implication for branched chain alpha-ketoacids transport in neurons.	2003 Sep-Oct	12742073
Catabolism of leucine to branched-chain fatty acids in Staphylococcus xylosus.	2004	15078537
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	15033367
Metabonomic investigations in mice infected with Schistosoma mansoni: an approach for biomarker identification.	2004 Aug 24	15314235
Tissue-specific regulation of 4E-BP1 and S6K1 phosphorylation by alpha-ketoisocaproate.	2004 Feb	15228219
Prolactin, progesterone, and dexamethasone coordinately and adversely regulate glucokinase and cAMP/PDE cascades in MIN6 beta-cells.	2004 Feb	14559722
Intrahippocampal administration of the alpha-keto acids accumulating in maple syrup urine disease provokes learning deficits in rats.	2004 Jan	14724056
Effects of antenatal steroids on protein metabolism in preterm infants on the first day of life.	2004 Jan	14722522
Central administration of leucine, but not isoleucine and valine, stimulates feeding behavior in neonatal chicks.	2004 Jan 9	14698464
13C-breath tests in the study of mitochondrial liver function.	2004 Jan-Feb	15209152
alpha-Aminoadipate aminotransferase from an extremely thermophilic bacterium, Thermus thermophilus.	2004 Jul	15256574
Nutritional supplementation acutely increases albumin fractional synthetic rate in chronic hemodialysis patients.	2004 Jul	15213282
Role of renal D-amino-acid oxidase in pharmacokinetics of D-leucine.	2004 Jul	15026304
Kidney protein dynamics and ammoniagenesis in humans with chronic metabolic acidosis.	2004 Jun	15153572
Protein synthesis rates of human PBMC and PMN can be determined simultaneously in vivo by using small blood samples.	2004 Jun	14749219
Chemical conversion of alpha-keto acids in relation to flavor formation in fermented foods.	2004 Mar 10	14995131
Tacrolimus impairment of insulin secretion in isolated rat islets occurs at multiple distal sites in stimulus-secretion coupling.	2004 May	14962991
Evidence that the branched-chain alpha-keto acids accumulating in maple syrup urine disease induce morphological alterations and death in cultured astrocytes from rat cerebral cortex.	2004 Nov 15	15390119
Branched-chain amino acid aminotransferase and methionine formation in Mycobacterium tuberculosis.	2004 Oct 7	15471546

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:48:18 GMT 2025` Edited by `admin` on `Mon Mar 31 17:48:18 GMT 2025`
Record UNII	4GUJ8AH400
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2-OXOISOCAPROATE

Preferred Name

English

.ALPHA.-KETOISOCAPROIC ACID

Systematic Name

English

KETOLEUCINE

Systematic Name

English

4-METHYL-2-OXOVALERIC ACID

Systematic Name

English

4-METHYL-2-OXOPENTANOIC ACID

Systematic Name

English

PENTANOIC ACID, 4-METHYL-2-OXO-

Common Name

English

2-OXOLEUCINE

Common Name

English

2-KETO-4-METHYLVALERIC ACID

Systematic Name

English

Classification Tree Code System Code

DSLD

1491 (Number of products:4)