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=C(N)C=CC=C1)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 |
|---|---|---|
| Accumulation of toxic products degradation of kynurenine in hemodialyzed patients. | 2001 |
|
| [Enzymes of the kynurenine pathway]. | 2001 |
|
| Monitoring of immune activation using biochemical changes in a porcine model of cardiac arrest. | 2001 Dec |
|
| IFN-beta1b induces kynurenine pathway metabolism in human macrophages: potential implications for multiple sclerosis treatment. | 2001 Dec |
|
| Kynurenine and its metabolites in the rat with experimental renal insufficiency. | 2001 Dec |
|
| N(G)-nitro-L-arginine and its methyl ester inhibit brain synthesis of kynurenic acid possibly via nitric oxide-independent mechanism. | 2001 Nov-Dec |
|
| Glutathione and NADH, but not ascorbate, protect lens proteins from modification by UV filters. | 2002 Apr |
|
| Aerobic and anaerobic NAD+ metabolism in Saccharomyces cerevisiae. | 2002 Apr 24 |
|
| Effect of indoleamine 2,3-dioxygenase on induction of experimental autoimmune encephalomyelitis. | 2002 Aug |
|
| UV filter instability: consequences for the human lens. | 2002 Aug |
|
| Isolation, characterization, and functional expression of kynurenine aminotransferase cDNA from the yellow fever mosquito, Aedes aegypti(1). | 2002 Aug |
|
| Increased levels of 3-hydroxykynurenine in different brain regions of rats with chronic renal insufficiency. | 2002 Aug 15 |
|
| FcepsilonRI induces the tryptophan degradation pathway involved in regulating T cell responses. | 2002 Aug 15 |
|
| Dynamic diversity of the tryptophan pathway in chlamydiae: reductive evolution and a novel operon for tryptophan recapture. | 2002 Aug 29 |
|
| Increased neopterin production and tryptophan degradation in advanced Parkinson's disease. | 2002 Feb |
|
| 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 Feb |
|
| Concurrent quantification of quinolinic, picolinic, and nicotinic acids using electron-capture negative-ion gas chromatography-mass spectrometry. | 2002 Feb 1 |
|
| Kynureninase is a novel candidate gene for hypertension in spontaneously hypertensive rats. | 2002 Jan |
|
| 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 Jan |
|
| Cloning and characterization of the Tribolium castaneum eye-color genes encoding tryptophan oxygenase and kynurenine 3-monooxygenase. | 2002 Jan |
|
| [Microanalysis of tryptophan metabolites and suppressor factor of delayed-type hypersensitivity in mice]. | 2002 Jul |
|
| Characterization of the human gene encoding alpha-aminoadipate aminotransferase (AADAT). | 2002 Jul |
|
| 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 Jul |
|
| "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 Jul 17 |
|
| Endothelium-dependent production and liberation of kynurenic acid by rat aortic rings exposed to L-kynurenine. | 2002 Jul 19 |
|
| Different structural organization of the encephalopsin gene in man and mouse. | 2002 Jul 24 |
|
| The pharmacological manipulation of glutamate receptors and neuroprotection. | 2002 Jul 5 |
|
| Regulation of kynurenic acid synthesis in C6 glioma cells. | 2002 Jun 1 |
|
| Serum tryptophan decrease correlates with immune activation and impaired quality of life in colorectal cancer. | 2002 Jun 5 |
|
| Characterization of the kynurenine 3-monooxygenase gene corresponding to the white egg 1 mutant in the silkworm Bombyx mori. | 2002 Mar |
|
| Tryptophan metabolism via the kynurenine pathway in experimental chronic renal failure. | 2002 Mar |
|
| More rapid method for simultaneous measurement of tryptophan and kynurenine by HPLC. | 2002 Mar |
|
| The clinical significance of cerebrospinal fluid levels of kynurenine pathway metabolites and lactate in severe malaria. | 2002 Mar 1 |
|
| Excitatory and inhibitory responses of dopamine neurons in the ventral tegmental area to nicotine. | 2002 Mar 15 |
|
| 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 Mar 25 |
|
| Increased phasic activity of dopaminergic neurones in the rat ventral tegmental area following pharmacologically elevated levels of endogenous kynurenic acid. | 2002 May |
|
| Enzyme activities along the tryptophan-nicotinic acid pathway in alloxan diabetic rabbits. | 2002 May 10 |
|
| 3-Hydroxykynurenine transaminase identity with alanine glyoxylate transaminase. A probable detoxification protein in Aedes aegypti. | 2002 May 3 |
|
| CTLA-4-Ig regulates tryptophan catabolism in vivo. | 2002 Nov |
|
| Manipulation of brain kynurenines: glial targets, neuronal effects, and clinical opportunities. | 2002 Oct |
|
| T cell apoptosis by tryptophan catabolism. | 2002 Oct |
|
| cDNA cloning, functional expression and characterization of kynurenine 3-hydroxylase of Anopheles stephensi (Diptera: Culicidae). | 2002 Oct |
|
| Decreased level of kynurenic acid in cerebrospinal fluid of relapsing-onset multiple sclerosis patients. | 2002 Oct 4 |
|
| Kynurenine 3-mono-oxygenase inhibitors attenuate post-ischemic neuronal death in organotypic hippocampal slice cultures. | 2002 Sep |
|
| Effective antiretroviral therapy reduces degradation of tryptophan in patients with HIV-1 infection. | 2002 Sep |
|
| A modified kynurenine bioassay for quantitative determination of human interferon-gamma. | 2002 Sep 1 |
|
| Comparative characterization of Aedes 3-hydroxykynurenine transaminase/alanine glyoxylate transaminase and Drosophila serine pyruvate aminotransferase. | 2002 Sep 11 |
|
| 1-Methyl-4-phenylpyridinium and 3-nitropropionic acid diminish cortical synthesis of kynurenic acid via interference with kynurenine aminotransferases in rats. | 2002 Sep 13 |
|
| 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 Sep 6 |
|
| Purine, kynurenine, neopterin and lipid peroxidation levels in inflammatory bowel disease. | 2002 Sep-Oct |
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
Sat Dec 16 14:46:18 UTC 2023
by
admin
on
Sat Dec 16 14:46:18 UTC 2023
|
| Record UNII |
02JW4J5R44
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
LOINC |
53490-9
Created by
admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
|
||
|
LOINC |
53507-0
Created by
admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
|
||
|
LOINC |
53491-7
Created by
admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
|
||
|
LOINC |
53470-1
Created by
admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
|
||
|
LOINC |
53734-0
Created by
admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
|
||
|
LOINC |
74942-4
Created by
admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
16946
Created by
admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
|
PRIMARY | |||
|
C129555
Created by
admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
|
PRIMARY | |||
|
28683
Created by
admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
|
PRIMARY | |||
|
KYNURENINE
Created by
admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
|
PRIMARY | |||
|
02JW4J5R44
Created by
admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
|
PRIMARY | |||
|
DTXSID101031182
Created by
admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
|
PRIMARY | |||
|
161166
Created by
admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
|
PRIMARY | |||
|
2922-83-0
Created by
admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
|
PRIMARY | |||
|
C73539
Created by
admin on Sat Dec 16 14:46:19 UTC 2023 , Edited by admin on Sat Dec 16 14:46:19 UTC 2023
|
NO STRUCTURE GIVEN |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
SOLVATE->ANHYDROUS |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
PARENT -> METABOLITE |
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
