KYNURENINE, (±)-

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 Search

SMILES

NC(CC(=O)C1=CC=CC=C1N)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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13518337
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).

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Solute carrier organic anion transporter family member 1B1 32 Target ID: CHEMBL1697668 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23571415	Inhibitor 8504
Solute carrier organic anion transporter family member 1B3 16 Target ID: CHEMBL1743121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23571415	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Ischemia 16 Sources: https://worldwide.espacenet.com/publicationDetails/biblio?DB=EPODOC&II=0&ND=3&adjacent=true&locale=en_EP&FT=D&date=20170407&CC=FR&NR=3041882A1&KC=A1	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Systemic DL-kynurenine and probenecid pretreatment attenuates quinolinic acid-induced neurotoxicity in rats.	1996-01	8684593

Patents

Sample Use Guides

In Vivo Use Guide

Rats were treated with DL-Kynurenine at 150, 300 and 450 mg/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

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 `Mon Mar 31 22:57:40 GMT 2025` Edited by `admin` on `Mon Mar 31 22:57:40 GMT 2025`
Record UNII	298M20B2AU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

(±)-KYNURENINE

Preferred 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