Structure via PubChem · Public domain (PubChem)
L-kynurenine
Sign in to saveAlso known as (S)-2-amino-4-(2-aminophenyl)- 4-oxo-butanoic acid, (S)-kynurenine, L-2-Amino-4-[2-Aminophenyl]-4-Oxobutanoic Acid, kynurenine
-Kynurenine is a metabolite of the amino acid -tryptophan used in the production of niacin.
Chemical data
- Formula
- C10H12N2O3
- Molecular weight
- 208.21 g/mol
- IUPAC name
- (2S)-4-(2-aminophenyl)-2-azaniumyl-4-oxobutanoate
- SMILES
- C1=CC=C(C(=C1)C(=O)C[C@@H](C(=O)[O-])[NH3+])N
- InChIKey
- YGPSJZOEDVAXAB-QMMMGPOBSA-N
- XLogP
- -1.4
- Polar surface area
- 111 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
9,443 papers- L-Kynurenine activates the AHR-PCSK9 pathway to mediate the lipid metabolic and ovarian dysfunction in polycystic ovary syndrome.Metabolism: clinical and experimental · 2025
- Blockade of the AHR restricts a Treg-macrophage suppressive axis induced by L-Kynurenine.Nature communications · 2020
- L-Kynurenine regulates immune response in ICIs-associated myocarditis via JAK/STAT pathway.International immunopharmacology · 2025
- Ginseng polysaccharides alter the gut microbiota and kynurenine/tryptophan ratio, potentiating the antitumour effect of antiprogrammed cell death 1/programmed cell death ligand 1 (anti-PD-1/PD-L1) immunotherapy.Gut · 2022
- L-kynurenine: its synthesis and possible regulatory function in brain.Neurochemical research · 1980
via PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 208.084792244
Show 6 more facts
- canonical SMILES
- C1=CC=C(C(=C1)C(=O)CC(C(=O)O)N)N
- chemical formula
- C₁₀H₁₂N₂O₃
- found in taxon
- Caenorhabditis elegans
- isomeric SMILES
- C1=CC=C(C(=C1)C(=O)C[C@@H](C(=O)O)N)N
- Commons category
- Kynurenine
- subject has role
- primary metabolite
via Wikidata · CC0
~4 min read
Encyclopedic overview
6 sectionsContents
- Biosynthesis
- Metabolism
- Clinical effects
- Kynurenine pathway dysfunction
- Drug development
- References
-Kynurenine is a metabolite of the amino acid -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. An important source is the intestine. Kynurenine and its further breakdown products carry out diverse biological functions, including dilating blood vessels during inflammation and regulating the immune response. Some cancers increase kynurenine production, which increases tumor growth.
Excerpted from Wikipedia’s “L-kynurenine” article, available under the CC BY-SA 4.0 licence.