Names | |
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Preferred IUPAC name
(2S)-2-Amino-4-(2-aminophenyl)-4-oxo-butanoic acid | |
Other names
(S)-Kynurenine
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Identifiers | |
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3D model (JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
MeSH | Kynurenine |
PubChem CID
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UNII | |
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Properties | |
C10H12N2O3 | |
Molar mass | 208.217 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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l-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.[1] Kynurenine and its further breakdown products carry out diverse biological functions, including dilating blood vessels during inflammation[2] and regulating the immune response.[3] Some cancers increase kynurenine production, which increases tumor growth.[1]
Evidence suggests that increased kynurenine production may precipitate depressive symptoms associated with interferon treatment for hepatitis C.[4] Cognitive deficits in schizophrenia are associated with imbalances in the enzymes that break down kynurenine.[5] Blood levels of kynurenine are reduced in people with bipolar disorder.[6] Kynurenine production is increased in Alzheimer's disease[7] and cardiovascular disease[8] where its metabolites are associated with cognitive deficits[9] and depressive symptoms.[10] Kynurenine is also associated with tics.[11][12]
Kynureninase catabolizes the conversion of kynurenine into anthranilic acid[13] while kynurenine-oxoglutarate transaminase catabolizes its conversion into kynurenic acid. Kynurenine 3-hydroxylase converts kynurenine to 3-hydroxykynurenine.[14]
Kynurenine has also been identified as one of two compounds that makes up the pigment that gives the goldenrod crab spider its yellow color.[15]
Dysfunctional states of distinct steps of the kynurenine pathway (such as kynurenine, kynurenic acid, quinolinic acid, anthranilic acid, 3-hydroxykynurenine) have been described for a number of disorders, including:[17]
Downregulation of kynurenine-3-monooxygenase (KMO) can be caused by genetic polymorphisms, cytokines, or both.[20][21] KMO deficiency leads to an accumulation of kynurenine and to a shift within the tryptophan metabolic pathway towards kynurenine acid and anthranilic acid.[22] Kynurenine-3-monooxygenase deficiency is associated with disorders of the brain (e.g. major depressive disorder, bipolar disorder, schizophrenia, tic disorders) [23] and of the liver.[11][24][25][26][27]