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Details

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

SHOW SMILES / InChI
Structure of KYNURENINE, (±)-

SMILES

NC(CC(=O)C1=C(N)C=CC=C1)C(O)=O

InChI

InChIKey=YGPSJZOEDVAXAB-UHFFFAOYSA-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)

HIDE SMILES / InChI

Molecular Formula C10H12N2O3
Molecular Weight 208.2139
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/8684593 | https://www.ncbi.nlm.nih.gov/pubmed/23571415

DL-Kynurenine is a racemic mixture of D-kynurenine and L-kynurenine. Kynurenine is the precursor of kynurenic acid, an endogenous antagonist of the glycine site of the NMDA (N-methyl-D-aspartate) receptor. Kynurenine has been identified as an endogenous ligand of the aryl hydrocarbon receptor (AhR), a receptor known to be activated by various environmental toxicants, such as 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD).

Originator

Sources: Z. physiol. Chem. (1934), 226, 29-31.

Approval Year

PubMed

PubMed

TitleDatePubMed
Systemic DL-kynurenine and probenecid pretreatment attenuates quinolinic acid-induced neurotoxicity in rats.
1996 Jan
Patents

Patents

Sample Use Guides

Rats were treated with DL-Kynurenine at 150, 300 and 450 mg/kg
Route of Administration: Intraperitoneal
HepG2 cells were cultured in a humidified atmosphere containing 5% CO2 for 24 hours under basal conditions and for another 24 hours under the evaluated conditions. Cells were cultured in six-well plates at 5 x 10^5 /well, except during the LDH release assay, when cells were cultured in 96-well plates at 10^4 /well. Cells were maintained untreated or treated with 100 mmol/L CoCl2, 50 mmol/L kynurenine, or 3 mmol/L CH223191 or various combinations. Cytotoxicity was assessed by LDH-release assay
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:00:18 GMT 2023
Edited
by admin
on Sat Dec 16 10:00:18 GMT 2023
Record UNII
298M20B2AU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
KYNURENINE, (±)-
Common Name English
(±)-KYNURENINE
Common Name English
ALANINE, 3-ANTHRANILOYL-
Systematic Name English
KYNURENINE, DL-
Common Name English
KYNURENINE [MI]
Common Name English
DL-KYNURENINE
Common Name English
BENZENEBUTANOIC ACID, .ALPHA.,2-DIAMINO-.GAMMA.-OXO-
Systematic Name English
Code System Code Type Description
FDA UNII
298M20B2AU
Created by admin on Sat Dec 16 10:00:18 GMT 2023 , Edited by admin on Sat Dec 16 10:00:18 GMT 2023
PRIMARY
EPA CompTox
DTXSID90861884
Created by admin on Sat Dec 16 10:00:18 GMT 2023 , Edited by admin on Sat Dec 16 10:00:18 GMT 2023
PRIMARY
ECHA (EC/EINECS)
206-445-9
Created by admin on Sat Dec 16 10:00:18 GMT 2023 , Edited by admin on Sat Dec 16 10:00:18 GMT 2023
PRIMARY
CAS
343-65-7
Created by admin on Sat Dec 16 10:00:18 GMT 2023 , Edited by admin on Sat Dec 16 10:00:18 GMT 2023
PRIMARY
MERCK INDEX
m6646
Created by admin on Sat Dec 16 10:00:18 GMT 2023 , Edited by admin on Sat Dec 16 10:00:18 GMT 2023
PRIMARY Merck Index
PUBCHEM
846
Created by admin on Sat Dec 16 10:00:18 GMT 2023 , Edited by admin on Sat Dec 16 10:00:18 GMT 2023
PRIMARY