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
SMILES
N[C@@H](CC(=O)C1=CC=CC=C1N)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
| 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 |
DescriptionCurator'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
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.
CNS Activity
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| CTLA-4-Ig regulates tryptophan catabolism in vivo. | 2002-11 |
|
| Decreased level of kynurenic acid in cerebrospinal fluid of relapsing-onset multiple sclerosis patients. | 2002-10-04 |
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| Manipulation of brain kynurenines: glial targets, neuronal effects, and clinical opportunities. | 2002-10 |
|
| T cell apoptosis by tryptophan catabolism. | 2002-10 |
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| cDNA cloning, functional expression and characterization of kynurenine 3-hydroxylase of Anopheles stephensi (Diptera: Culicidae). | 2002-10 |
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| 1-Methyl-4-phenylpyridinium and 3-nitropropionic acid diminish cortical synthesis of kynurenic acid via interference with kynurenine aminotransferases in rats. | 2002-09-13 |
|
| Comparative characterization of Aedes 3-hydroxykynurenine transaminase/alanine glyoxylate transaminase and Drosophila serine pyruvate aminotransferase. | 2002-09-11 |
|
| Purine, kynurenine, neopterin and lipid peroxidation levels in inflammatory bowel disease. | 2002-09-10 |
|
| Depressive and anxiety symptoms in the early puerperium are related to increased degradation of tryptophan into kynurenine, a phenomenon which is related to immune activation. | 2002-09-06 |
|
| A modified kynurenine bioassay for quantitative determination of human interferon-gamma. | 2002-09-01 |
|
| Kynurenine 3-mono-oxygenase inhibitors attenuate post-ischemic neuronal death in organotypic hippocampal slice cultures. | 2002-09 |
|
| Effective antiretroviral therapy reduces degradation of tryptophan in patients with HIV-1 infection. | 2002-09 |
|
| Dynamic diversity of the tryptophan pathway in chlamydiae: reductive evolution and a novel operon for tryptophan recapture. | 2002-08-29 |
|
| Increased levels of 3-hydroxykynurenine in different brain regions of rats with chronic renal insufficiency. | 2002-08-15 |
|
| FcepsilonRI induces the tryptophan degradation pathway involved in regulating T cell responses. | 2002-08-15 |
|
| Effect of indoleamine 2,3-dioxygenase on induction of experimental autoimmune encephalomyelitis. | 2002-08 |
|
| UV filter instability: consequences for the human lens. | 2002-08 |
|
| Isolation, characterization, and functional expression of kynurenine aminotransferase cDNA from the yellow fever mosquito, Aedes aegypti(1). | 2002-08 |
|
| Different structural organization of the encephalopsin gene in man and mouse. | 2002-07-24 |
|
| Endothelium-dependent production and liberation of kynurenic acid by rat aortic rings exposed to L-kynurenine. | 2002-07-19 |
|
| "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. | 2002-07-17 |
|
| The pharmacological manipulation of glutamate receptors and neuroprotection. | 2002-07-05 |
|
| [Microanalysis of tryptophan metabolites and suppressor factor of delayed-type hypersensitivity in mice]. | 2002-07 |
|
| Characterization of the human gene encoding alpha-aminoadipate aminotransferase (AADAT). | 2002-07 |
|
| 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. | 2002-07 |
|
| Serum tryptophan decrease correlates with immune activation and impaired quality of life in colorectal cancer. | 2002-06-05 |
|
| Regulation of kynurenic acid synthesis in C6 glioma cells. | 2002-06-01 |
|
| Enzyme activities along the tryptophan-nicotinic acid pathway in alloxan diabetic rabbits. | 2002-05-10 |
|
| N(G)-nitro-L-arginine and its methyl ester inhibit brain synthesis of kynurenic acid possibly via nitric oxide-independent mechanism. | 2002-05-03 |
|
| 3-Hydroxykynurenine transaminase identity with alanine glyoxylate transaminase. A probable detoxification protein in Aedes aegypti. | 2002-05-03 |
|
| Increased phasic activity of dopaminergic neurones in the rat ventral tegmental area following pharmacologically elevated levels of endogenous kynurenic acid. | 2002-05 |
|
| Aerobic and anaerobic NAD+ metabolism in Saccharomyces cerevisiae. | 2002-04-24 |
|
| Glutathione and NADH, but not ascorbate, protect lens proteins from modification by UV filters. | 2002-04 |
|
| Novel and sensitive high-performance liquid chromatographic method based on electrochemical coulometric array detection for simultaneous determination of catecholamines, kynurenine and indole derivatives of tryptophan. | 2002-03-25 |
|
| Excitatory and inhibitory responses of dopamine neurons in the ventral tegmental area to nicotine. | 2002-03-15 |
|
| The clinical significance of cerebrospinal fluid levels of kynurenine pathway metabolites and lactate in severe malaria. | 2002-03-01 |
|
| Characterization of the kynurenine 3-monooxygenase gene corresponding to the white egg 1 mutant in the silkworm Bombyx mori. | 2002-03 |
|
| Tryptophan metabolism via the kynurenine pathway in experimental chronic renal failure. | 2002-03 |
|
| More rapid method for simultaneous measurement of tryptophan and kynurenine by HPLC. | 2002-03 |
|
| Concurrent quantification of quinolinic, picolinic, and nicotinic acids using electron-capture negative-ion gas chromatography-mass spectrometry. | 2002-02-01 |
|
| Increased neopterin production and tryptophan degradation in advanced Parkinson's disease. | 2002-02 |
|
| Increased depressive ratings in patients with hepatitis C receiving interferon-alpha-based immunotherapy are related to interferon-alpha-induced changes in the serotonergic system. | 2002-02 |
|
| Kynureninase is a novel candidate gene for hypertension in spontaneously hypertensive rats. | 2002-01 |
|
| The central role of magnesium deficiency in Tourette's syndrome: causal relationships between magnesium deficiency, altered biochemical pathways and symptoms relating to Tourette's syndrome and several reported comorbid conditions. | 2002-01 |
|
| Cloning and characterization of the Tribolium castaneum eye-color genes encoding tryptophan oxygenase and kynurenine 3-monooxygenase. | 2002-01 |
|
| Monitoring of immune activation using biochemical changes in a porcine model of cardiac arrest. | 2001-12 |
|
| IFN-beta1b induces kynurenine pathway metabolism in human macrophages: potential implications for multiple sclerosis treatment. | 2001-12 |
|
| Kynurenine and its metabolites in the rat with experimental renal insufficiency. | 2001-12 |
|
| Accumulation of toxic products degradation of kynurenine in hemodialyzed patients. | 2001 |
|
| [Enzymes of the kynurenine pathway]. | 2001 |
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
Edited
Wed Apr 02 01:07:08 GMT 2025
by
admin
on
Wed Apr 02 01:07:08 GMT 2025
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| Record UNII |
02JW4J5R44
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| Record Status |
Validated (UNII)
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| Record Version |
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53490-9
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53507-0
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53734-0
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74942-4
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16946
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C129555
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28683
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KYNURENINE
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02JW4J5R44
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DTXSID101031182
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2922-83-0
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C73539
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NO STRUCTURE GIVEN |
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SOLVATE->ANHYDROUS |
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PARENT -> METABOLITE |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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