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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H12N2O3
Molecular Weight 208.2139
Optical Activity ( + )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of KYNURENINE

SMILES

N[C@@H](CC(=O)C1=C(N)C=CC=C1)C(O)=O

InChI

InChIKey=YGPSJZOEDVAXAB-QMMMGPOBSA-N
InChI=1S/C10H12N2O3/c11-7-4-2-1-3-6(7)9(13)5-8(12)10(14)15/h1-4,8H,5,11-12H2,(H,14,15)/t8-/m0/s1

HIDE SMILES / InChI

Molecular Formula C10H12N2O3
Molecular Weight 208.2139
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/526758 | https://www.ncbi.nlm.nih.gov/pubmed/4587003 | https://www.ncbi.nlm.nih.gov/pubmed/10226937 | https://www.ncbi.nlm.nih.gov/pubmed/28551532

Kynurenine is a metabolite of the amino acid L-tryptophan used in the production of niacin. Kynurenine is synthesized by the enzyme tryptophan dioxygenase, which is made primarily but not exclusively in the liver, and indoleamine 2,3-dioxygenase, which is made in many tissues in response to immune activation. Kynurenine and its further breakdown products carry out diverse biological functions, including dilating blood vessels during inflammation and regulating the immune response. Evidence suggests that increased kynurenine production may precipitate depressive symptoms associated with interferon treatment for hepatitis C. Cognitive deficits in schizophrenia are associated with imbalances in the enzymes that break down kynurenine. Kynurenine production is increased in Alzheimer's disease and cardiovascular disease where its metabolites are associated with cognitive deficits and depressive symptoms.

Originator

Sources: Z. physiol. Chem. (1931), 195, 152-8.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Accumulation of toxic products degradation of kynurenine in hemodialyzed patients.
2001
Regulation of prostaglandin synthesis and cell adhesion by a tryptophan catabolizing enzyme.
2001
Neopterin production and tryptophan degradation in humans infected by Streptococcus pyogenes.
2001 Apr
A comparative study on the inhibition of human and bacterial kynureninase by novel bicyclic kynurenine analogues.
2001 Apr
Kynurenic acid antagonists and kynurenine pathway inhibitors.
2001 Apr
The presence of a human UV filter within the lens represents an oxidative stress.
2001 Apr
Neonatal asphyxia in rats: acute effects on cerebral kynurenine metabolism.
2001 Aug
Kynurenine binds to the peptide binding region of the chaperone alphaB-crystallin.
2001 Aug 3
Kynurenine aminotransferase and glutamine transaminase K of Escherichia coli: identity with aspartate aminotransferase.
2001 Dec 15
Presence of kynurenic acid and kynurenine aminotransferases in the inner retina.
2001 Dec 4
Kynurenine aminotransferase I activity in human placenta.
2001 Feb-Mar
Effects of nicotine on head-shakes and tryptophan metabolites.
2001 Jan
Regional changes in kynurenic acid, quinolinic acid, and glial fibrillary acidic protein concentrations in the fetal sheep brain after experimentally induced placental insufficiency.
2001 Jan
Presynaptic kynurenate-sensitive receptors inhibit glutamate release.
2001 Jun
Similarities and differences in the neuronal death processes activated by 3OH-kynurenine and quinolinic acid.
2001 Jun
The protective role of HSP90 against 3-hydroxykynurenine-induced neuronal apoptosis.
2001 Jun 8
Indoleamine 2,3-dioxygenase in the human lens, the first enzyme in the synthesis of UV filters.
2001 Mar
Excitotoxic injury stimulates pro-drug-induced 7-chlorokynurenate formation in the rat striatum in vivo.
2001 May 25
Localizing value of alpha-methyl-L-tryptophan PET in intractable epilepsy of neocortical origin.
2001 Nov 13
The brain metabolite kynurenic acid inhibits alpha7 nicotinic receptor activity and increases non-alpha7 nicotinic receptor expression: physiopathological implications.
2001 Oct 1
Study of the brain serotonergic system with labeled alpha-methyl-L-tryptophan.
2001 Sep
Glutathione and NADH, but not ascorbate, protect lens proteins from modification by UV filters.
2002 Apr
Aerobic and anaerobic NAD+ metabolism in Saccharomyces cerevisiae.
2002 Apr 24
UV filter instability: consequences for the human lens.
2002 Aug
Isolation, characterization, and functional expression of kynurenine aminotransferase cDNA from the yellow fever mosquito, Aedes aegypti(1).
2002 Aug
Novel protein modification by kynurenine in human lenses.
2002 Feb 15
Inhibition of nNOS activity in rat brain by synthetic kynurenines: structure-activity dependence.
2002 Jan 17
Effects of systemic and central nervous system localized inflammation on the contributions of metabolic precursors to the L-kynurenine and quinolinic acid pools in brain.
2002 Jul
"Untypical aging off-flavor" in wine: synthesis of potential degradation compounds of indole-3-acetic acid and kynurenine and their evaluation as precursors of 2-aminoacetophenone.
2002 Jul 17
Endothelium-dependent production and liberation of kynurenic acid by rat aortic rings exposed to L-kynurenine.
2002 Jul 19
Serum tryptophan decrease correlates with immune activation and impaired quality of life in colorectal cancer.
2002 Jun 5
The clinical significance of cerebrospinal fluid levels of kynurenine pathway metabolites and lactate in severe malaria.
2002 Mar 1
Enzyme activities along the tryptophan-nicotinic acid pathway in alloxan diabetic rabbits.
2002 May 10
Effective antiretroviral therapy reduces degradation of tryptophan in patients with HIV-1 infection.
2002 Sep
1-Methyl-4-phenylpyridinium and 3-nitropropionic acid diminish cortical synthesis of kynurenic acid via interference with kynurenine aminotransferases in rats.
2002 Sep 13
Purine, kynurenine, neopterin and lipid peroxidation levels in inflammatory bowel disease.
2002 Sep-Oct
Patents

Patents

Sample Use Guides

200-mg oral administration of L-kynurenine sulfate as a single dose.
Route of Administration: Oral
To measure the effect of the tested compounds (Kynurenine, 5, 10, 50 mkM) on the proliferation and viability of cells, a colorimetric assay was performed based on the cleavage of the water-soluble WST-1 (4- [3-(4-iodophenyl)-2-(4-nitrophenyl)-2H-5-tetrazolio]-1,3-ben- zene disulphonate) (tetrazolium salt) (Roche Diagnostics GmbH, Mannheim, Germany) by succinate dehydrogenase. Cells were incubated for a duration of 0–24 h and 24–48 h. At the end of the respective incubation period the medium was removed from the bottom part of the plate. 540 mkl of fresh medium without tested substances and 60 mkl of WST-1 solution (a concentration ready for use) were added and cells were incubated at 37 C and 5% CO2 for 3 h. Next, the culture supernatants were collected and 100 mkl of each in the replicates was added to a 96-well microplate and the absorbance was measured at 450 nm using a microplate reader
Substance Class Chemical
Created
by admin
on Sat Dec 16 14:46:18 UTC 2023
Edited
by admin
on Sat Dec 16 14:46:18 UTC 2023
Record UNII
02JW4J5R44
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
KYNURENINE
Common Name English
L-3-(O-AMINOBENZOYL)ALANINE
Common Name English
TRYPTOPHAN IMPURITY C [EP IMPURITY]
Common Name English
(2S)-2-AMINO-4-(2-AMINOPHENYL)-4-OXOBUTANOIC ACID
Systematic Name English
BENZENEBUTANOIC ACID, .ALPHA.,2-DIAMINO-.GAMMA.-OXO-, (S)-
Systematic Name English
BENZENEBUTANOIC ACID, .ALPHA.,2-DIAMINO-.GAMMA.-OXO-, (.ALPHA.S)-
Systematic Name English
KYNURENINE, L-
Common Name English
KYNURENINE, (+)-
Common Name English
N-ACETYLTRYPTOPHAN IMPURITY C [EP IMPURITY]
Common Name English
KYNURENIN
Common Name English
3-ANTHRANILOYLALANINE
Systematic Name English
Classification Tree Code System Code
LOINC 53490-9
Created by admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
LOINC 53507-0
Created by admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
LOINC 53491-7
Created by admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
LOINC 53470-1
Created by admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
LOINC 53734-0
Created by admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
LOINC 74942-4
Created by admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
Code System Code Type Description
CHEBI
16946
Created by admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
PRIMARY
NCI_THESAURUS
C129555
Created by admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
PRIMARY
CHEBI
28683
Created by admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
PRIMARY
WIKIPEDIA
KYNURENINE
Created by admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
PRIMARY
FDA UNII
02JW4J5R44
Created by admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
PRIMARY
EPA CompTox
DTXSID101031182
Created by admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
PRIMARY
PUBCHEM
161166
Created by admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
PRIMARY
CAS
2922-83-0
Created by admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
PRIMARY
NCI_THESAURUS
C73539
Created by admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
NO STRUCTURE GIVEN
Related Record Type Details
SOLVATE->ANHYDROUS
Related Record Type Details
PARENT -> METABOLITE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP