.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
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.	2004-11-15	15390119
Branched-chain amino acid aminotransferase and methionine formation in Mycobacterium tuberculosis.	2004-10-07	15471546
Metabonomic investigations in mice infected with Schistosoma mansoni: an approach for biomarker identification.	2004-08-24	15314235
alpha-Aminoadipate aminotransferase from an extremely thermophilic bacterium, Thermus thermophilus.	2004-07	15256574
Nutritional supplementation acutely increases albumin fractional synthetic rate in chronic hemodialysis patients.	2004-07	15213282
Role of renal D-amino-acid oxidase in pharmacokinetics of D-leucine.	2004-07	15026304
13C-breath tests in the study of mitochondrial liver function.	2004-06-24	15209152
Kidney protein dynamics and ammoniagenesis in humans with chronic metabolic acidosis.	2004-06	15153572
Protein synthesis rates of human PBMC and PMN can be determined simultaneously in vivo by using small blood samples.	2004-06	14749219
Tacrolimus impairment of insulin secretion in isolated rat islets occurs at multiple distal sites in stimulus-secretion coupling.	2004-05	14962991
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.	2004-04-02	15033367
Chemical conversion of alpha-keto acids in relation to flavor formation in fermented foods.	2004-03-10	14995131
Tissue-specific regulation of 4E-BP1 and S6K1 phosphorylation by alpha-ketoisocaproate.	2004-02	15228219
Prolactin, progesterone, and dexamethasone coordinately and adversely regulate glucokinase and cAMP/PDE cascades in MIN6 beta-cells.	2004-02	14559722
Central administration of leucine, but not isoleucine and valine, stimulates feeding behavior in neonatal chicks.	2004-01-09	14698464
Intrahippocampal administration of the alpha-keto acids accumulating in maple syrup urine disease provokes learning deficits in rats.	2004-01	14724056
Effects of antenatal steroids on protein metabolism in preterm infants on the first day of life.	2004-01	14722522
Catabolism of leucine to branched-chain fatty acids in Staphylococcus xylosus.	2004	15078537
Inhibition of brain energy metabolism by the alpha-keto acids accumulating in maple syrup urine disease.	2003-11-20	14636955
Quantitation of endogenous analytes in biofluid without a true blank matrix.	2003-11-01	14588026
Model to assess muscle protein turnover: domain of validity using amino acyl-tRNA vs. surrogate measures of precursor pool.	2003-11	14534080
Pyruvate inhibits zinc-mediated pancreatic islet cell death and diabetes.	2003-09	12898018
Gender differences in the regulation of amino acid metabolism.	2003-09	12807899
Acute effects of acidosis on protein and amino acid metabolism in perfused rat liver.	2003-08	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.	2003-08	12966324
Synergistic effects of testosterone and growth hormone on protein metabolism and body composition in prepubertal boys.	2003-08	12898459
Allosteric activators of glucokinase: potential role in diabetes therapy.	2003-07-18	12869762
Effects of fatty acids on hepatic amino acid catabolism and fibrinogen synthesis in young healthy volunteers.	2003-07	12791602
Opposite effects of glucose on plasma membrane Ca2+-ATPase and Na/Ca exchanger transcription, expression, and activity in rat pancreatic beta-cells.	2003-06-20	12682074
Expression of monocarboxylic acid transporters (MCT) in brain cells. Implication for branched chain alpha-ketoacids transport in neurons.	2003-05-14	12742073
A 48-hour exposure of pancreatic islets to calpain inhibitors impairs mitochondrial fuel metabolism and the exocytosis of insulin.	2003-05	12759879
Oxidation of essential amino acids by the ovine gastrointestinal tract.	2003-05	12720582
Distinguishing features of leucine and alpha-ketoisocaproate sensing in pancreatic beta-cells.	2003-05	12697702
Development of a capillary electrophoretic method for the analysis of amino acids containing tablets.	2003-04-18	12735449
In vivo assessment of the mitochondrial response to caloric restriction in obese women by the 2-keto[1-C]isocaproate breath test.	2003-04	12701059
Effects of environmental factors on leucine catabolism by Carnobacterium piscicola.	2003-03-25	12485743
Metabolism of brain amino acids following pentylenetetrazole treatment.	2003-02	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.	2003-02	12538793
Effect of minimal enteral feeding on splanchnic uptake of leucine in the postabsorptive state in preterm infants.	2003-02	12538787
Regulation of leucine-stimulated insulin secretion and glutamine metabolism in isolated rat islets.	2003-01-31	12444083
Characterization of homoisocitrate dehydrogenase involved in lysine biosynthesis of an extremely thermophilic bacterium, Thermus thermophilus HB27, and evolutionary implication of beta-decarboxylating dehydrogenase.	2003-01-17	12427751
Human mitochondrial and cytosolic branched-chain aminotransferases are cysteine S-conjugate beta-lyases, but turnover leads to inactivation.	2003-01-15	12504794
Mycobacterium tuberculosis ketopantoate hydroxymethyltransferase: tetrahydrofolate-independent hydroxymethyltransferase and enolization reactions with alpha-keto acids.	2003-01-14	12515554
Leucine promotes glucose uptake in skeletal muscles of rats.	2002-12-20	12470633
alpha-Ketoisocaproic acid regulates phosphorylation of intermediate filaments in postnatal rat cortical slices through ionotropic glutamatergic receptors.	2002-12-15	12480141
Insulin secretion induced by palmitate--a process fully dependent on glucose concentration.	2002-12	12688632
Kinetics of sequential metabolism from D-leucine to L-leucine via alpha-ketoisocaproic acid in rat.	2002-12	12433816
Role of blood cells in leucine kinetics across the human kidney.	2002-12	12388393
Effect of supply of metabolizable protein on whole body and splanchnic leucine metabolism in lactating dairy cows.	2002-10	12416817
Supplementing with beta-hydroxy-beta-methylbutyrate (HMB) to build and maintain muscle mass: a review.	2002	14632320

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

Download

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)