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 |
|---|---|---|
| [Enzymes of the kynurenine pathway]. | 2001 |
|
| Kynurenine 3-mono-oxygenase activity and neurotoxic kynurenine metabolites increase in the spinal cord of rats with experimental allergic encephalomyelitis. | 2001 |
|
| Neopterin production and tryptophan degradation in humans infected by Streptococcus pyogenes. | 2001 Apr |
|
| Kynurenic acid antagonists and kynurenine pathway inhibitors. | 2001 Apr |
|
| The presence of a human UV filter within the lens represents an oxidative stress. | 2001 Apr |
|
| Induction of indoleamine 2,3-dioxygenase in vivo by IFN-con1. | 2001 Aug |
|
| Neonatal asphyxia in rats: acute effects on cerebral kynurenine metabolism. | 2001 Aug |
|
| Increased kynurenic acid in the brain after neonatal asphyxia. | 2001 Aug 3 |
|
| Kynurenine aminotransferase and glutamine transaminase K of Escherichia coli: identity with aspartate aminotransferase. | 2001 Dec 15 |
|
| Kynurenic acid influences the respiratory parameters of rat heart mitochondria. | 2001 Feb |
|
| Pharmacologically elevated levels of endogenous kynurenic acid prevent nicotine-induced activation of nigral dopamine neurons. | 2001 Jan |
|
| Regional changes in kynurenic acid, quinolinic acid, and glial fibrillary acidic protein concentrations in the fetal sheep brain after experimentally induced placental insufficiency. | 2001 Jan |
|
| Major changes in human ocular UV protection with age. | 2001 Jan |
|
| Endogenous neurotoxins from tryptophan. | 2001 Jan |
|
| Possible involvement of kynurenamines in the pathogenesis of cataract in diabetic patients. | 2001 Jul-Aug |
|
| 3-Hydroxyanthranilic acid, an L-tryptophan metabolite, induces apoptosis in monocyte-derived cells stimulated by interferon-gamma. | 2001 May |
|
| Excitotoxic injury stimulates pro-drug-induced 7-chlorokynurenate formation in the rat striatum in vivo. | 2001 May 25 |
|
| Synthesis and release of neurotoxic kynurenine metabolites by human monocyte-derived macrophages. | 2001 Nov 1 |
|
| Free L-tryptophan plasma levels in antisocial violent offenders. | 2001 Oct |
|
| Increased cortical kynurenate content in schizophrenia. | 2001 Oct 1 |
|
| UV filter instability: consequences for the human lens. | 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 |
|
| Kynureninase is a novel candidate gene for hypertension in spontaneously hypertensive rats. | 2002 Jan |
|
| Serum tryptophan decrease correlates with immune activation and impaired quality of life in colorectal cancer. | 2002 Jun 5 |
|
| 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 |
|
| 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 |
|
| 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 |
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 GMT 2023
by
admin
on
Sat Dec 16 14:46:18 GMT 2023
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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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53491-7
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53470-1
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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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161166
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2922-83-0
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C73539
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NO STRUCTURE GIVEN |
| Related Record | Type | Details | ||
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SOLVATE->ANHYDROUS |
| Related Record | Type | Details | ||
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PARENT -> METABOLITE |
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| Related Record | Type | Details | ||
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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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