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Details

Stereochemistry ABSOLUTE
Molecular Formula C6H14N4O2.C6H10O3
Molecular Weight 304.3428
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ARGININE .ALPHA.-KETOISOCAPROATE

SMILES

CC(C)CC(=O)C(O)=O.N[C@@H](CCCNC(N)=N)C(O)=O

InChI

InChIKey=MOZIGXHKOXEDLJ-WCCKRBBISA-N
InChI=1S/C6H14N4O2.C6H10O3/c7-4(5(11)12)2-1-3-10-6(8)9;1-4(2)3-5(7)6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10);4H,3H2,1-2H3,(H,8,9)/t4-;/m0./s1

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

Molecular Formula C6H14N4O2
Molecular Weight 174.201
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
Differential acute and long term actions of succinic acid monomethyl ester exposure on insulin-secreting BRIN-BD11 cells.
2001
Effects of dietary protein restriction and amino acids deficiency on protein metabolism in dogs.
2001 Aug
Psychrophilic valine dehydrogenase of the antarctic psychrophile, Cytophaga sp. KUC-1: purification, molecular characterization and expression.
2001 Aug
Recovery of (13)CO(2) from infused [1-(13)C]leucine and [1,2-(13)C(2)]leucine in healthy humans.
2001 Aug
Phenotyping of individual pancreatic islets locates genetic defects in stimulus secretion coupling to Niddm1i within the major diabetes locus in GK rats.
2001 Dec
Tissue-specific regulation of mitochondrial and cytoplasmic protein synthesis rates by insulin.
2001 Dec
Modulation of absence seizures by branched-chain amino acids: correlation with brain amino acid concentrations.
2001 Jul
TPN-evoked dysfunction of islet lysosomal activity mediates impairment of glucose-stimulated insulin release.
2001 Jul
Leucine and its keto acid enhance the coordinated expression of genes for branched-chain amino acid catabolism in Arabidopsis under sugar starvation.
2001 Jun 15
Structures of Escherichia coli branched-chain amino acid aminotransferase and its complexes with 4-methylvalerate and 2-methylleucine: induced fit and substrate recognition of the enzyme.
2001 Jun 26
Recovery of function and mass of endogenous beta-cells in streptozotocin-induced diabetic rats treated with islet transplantation.
2001 Sep 14
Supplementing with beta-hydroxy-beta-methylbutyrate (HMB) to build and maintain muscle mass: a review.
2002
Increased synthesis rate of fibrinogen as a basis for its elevated plasma levels in obese female adolescents.
2002 Apr
Effects of leucine supplemented diet on intestinal absorption in tumor bearing pregnant rats.
2002 Apr 15
Synthesis rate of muscle proteins, muscle functions, and amino acid kinetics in type 2 diabetes.
2002 Aug
Insulin secretion induced by palmitate--a process fully dependent on glucose concentration.
2002 Dec
Kinetics of sequential metabolism from D-leucine to L-leucine via alpha-ketoisocaproic acid in rat.
2002 Dec
Role of blood cells in leucine kinetics across the human kidney.
2002 Dec
alpha-Ketoisocaproic acid regulates phosphorylation of intermediate filaments in postnatal rat cortical slices through ionotropic glutamatergic receptors.
2002 Dec 15
Leucine promotes glucose uptake in skeletal muscles of rats.
2002 Dec 20
Triggering of insulin release by a combination of cAMP signal and nutrients: an ATP-sensitive K+ channel-independent phenomenon.
2002 Feb
Protein turnover, lipolysis, and endogenous hormonal secretion in critically ill children.
2002 Jan
The antilipolytic agent 3,5-dimethylpyrazole inhibits insulin release in response to both nutrient secretagogues and cyclic adenosine monophosphate agonists in isolated rat islets.
2002 Jan
Short-term treatment with low doses of recombinant human GH stimulates lipolysis in visceral obese men.
2002 Jul
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
Effects of medium- and long-chain fatty acids on whole body leucine and glucose kinetics in man.
2002 Jun
Effect of supply of metabolizable protein on whole body and splanchnic leucine metabolism in lactating dairy cows.
2002 Oct
The stimulus-secretion coupling of amino acid-induced insulin release. Insulinotropic action of L-alanine.
2002 Oct 10
In vivo assessment of the mitochondrial response to caloric restriction in obese women by the 2-keto[1-C]isocaproate breath test.
2003 Apr
Acute effects of acidosis on protein and amino acid metabolism in perfused rat liver.
2003 Aug
Metabolism of brain amino acids following pentylenetetrazole treatment.
2003 Feb
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
Effect of minimal enteral feeding on splanchnic uptake of leucine in the postabsorptive state in preterm infants.
2003 Feb
Mycobacterium tuberculosis ketopantoate hydroxymethyltransferase: tetrahydrofolate-independent hydroxymethyltransferase and enolization reactions with alpha-keto acids.
2003 Jan 14
Human mitochondrial and cytosolic branched-chain aminotransferases are cysteine S-conjugate beta-lyases, but turnover leads to inactivation.
2003 Jan 15
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
Regulation of leucine-stimulated insulin secretion and glutamine metabolism in isolated rat islets.
2003 Jan 31
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
Effects of environmental factors on leucine catabolism by Carnobacterium piscicola.
2003 Mar 25
Oxidation of essential amino acids by the ovine gastrointestinal tract.
2003 May
Distinguishing features of leucine and alpha-ketoisocaproate sensing in pancreatic beta-cells.
2003 May
Expression of monocarboxylic acid transporters (MCT) in brain cells. Implication for branched chain alpha-ketoacids transport in neurons.
2003 Sep-Oct
Catabolism of leucine to branched-chain fatty acids in Staphylococcus xylosus.
2004
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
Metabonomic investigations in mice infected with Schistosoma mansoni: an approach for biomarker identification.
2004 Aug 24
Prolactin, progesterone, and dexamethasone coordinately and adversely regulate glucokinase and cAMP/PDE cascades in MIN6 beta-cells.
2004 Feb
Nutritional supplementation acutely increases albumin fractional synthetic rate in chronic hemodialysis patients.
2004 Jul
Role of renal D-amino-acid oxidase in pharmacokinetics of D-leucine.
2004 Jul
Kidney protein dynamics and ammoniagenesis in humans with chronic metabolic acidosis.
2004 Jun
Chemical conversion of alpha-keto acids in relation to flavor formation in fermented foods.
2004 Mar 10
Patents
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:38:35 GMT 2023
Edited
by admin
on Sat Dec 16 10:38:35 GMT 2023
Record UNII
7S4R4V1RM7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ARGININE .ALPHA.-KETOISOCAPROATE
Common Name English
NSC-353624
Code English
ARGININE 4-METHYL-2-OXOPENTANOATE
Common Name English
L-ARGININE, MONO(4-METHYL-2-OXOPENTANOATE)
Systematic Name English
Arginine alpha-ketoisocaproate [WHO-DD]
Common Name English
L-ARGININE, 4-METHYL-2-OXOPENTANOATE (1:1)
Systematic Name English
ARGININE ALPHA-KETOISOCAPROATE
WHO-DD  
Common Name English
ARGININE 2-KETOISOCAPROATE
Common Name English
Classification Tree Code System Code
DSLD 3836 (Number of products:4)
Created by admin on Sat Dec 16 10:38:35 GMT 2023 , Edited by admin on Sat Dec 16 10:38:35 GMT 2023
DSLD 2700 (Number of products:4)
Created by admin on Sat Dec 16 10:38:35 GMT 2023 , Edited by admin on Sat Dec 16 10:38:35 GMT 2023
Code System Code Type Description
CAS
72087-40-2
Created by admin on Sat Dec 16 10:38:35 GMT 2023 , Edited by admin on Sat Dec 16 10:38:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID90992809
Created by admin on Sat Dec 16 10:38:35 GMT 2023 , Edited by admin on Sat Dec 16 10:38:35 GMT 2023
PRIMARY
NSC
353624
Created by admin on Sat Dec 16 10:38:35 GMT 2023 , Edited by admin on Sat Dec 16 10:38:35 GMT 2023
PRIMARY
PUBCHEM
22812595
Created by admin on Sat Dec 16 10:38:35 GMT 2023 , Edited by admin on Sat Dec 16 10:38:35 GMT 2023
PRIMARY
ECHA (EC/EINECS)
276-326-4
Created by admin on Sat Dec 16 10:38:35 GMT 2023 , Edited by admin on Sat Dec 16 10:38:35 GMT 2023
PRIMARY
FDA UNII
7S4R4V1RM7
Created by admin on Sat Dec 16 10:38:35 GMT 2023 , Edited by admin on Sat Dec 16 10:38:35 GMT 2023
PRIMARY
Related Record Type Details
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