Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | 3C10H12N2O3.H2O |
| Molecular Weight | 642.6569 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.N[C@@H](CC(=O)C1=C(N)C=CC=C1)C(O)=O.N[C@@H](CC(=O)C2=C(N)C=CC=C2)C(O)=O.N[C@@H](CC(=O)C3=C(N)C=CC=C3)C(O)=O
InChI
InChIKey=JXVBVHHEQOIMHW-GJQOQBEKSA-N
InChI=1S/3C10H12N2O3.H2O/c3*11-7-4-2-1-3-6(7)9(13)5-8(12)10(14)15;/h3*1-4,8H,5,11-12H2,(H,14,15);1H2/t3*8-;/m000./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 |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| A comparative study on the inhibition of human and bacterial kynureninase by novel bicyclic kynurenine analogues. | 2001 Apr |
|
| Fructose malabsorption is associated with decreased plasma tryptophan. | 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 |
|
| Tryptophan catabolism in Brevibacterium linens as a potential cheese flavor adjunct. | 2001 Aug |
|
| Increased kynurenic acid in the brain after neonatal asphyxia. | 2001 Aug 3 |
|
| Kynurenic acid influences the respiratory parameters of rat heart mitochondria. | 2001 Feb |
|
| Kynurenine aminotransferase I activity in human placenta. | 2001 Feb-Mar |
|
| 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 |
|
| Presynaptic kynurenate-sensitive receptors inhibit glutamate release. | 2001 Jun |
|
| Kynurenines in the CNS: from endogenous obscurity to therapeutic importance. | 2001 Jun |
|
| The protective role of HSP90 against 3-hydroxykynurenine-induced neuronal apoptosis. | 2001 Jun 8 |
|
| 3-Hydroxyanthranilic acid, an L-tryptophan metabolite, induces apoptosis in monocyte-derived cells stimulated by interferon-gamma. | 2001 May |
|
| Prenatal exposure to methyl mercury in rats: focus on changes in kynurenine pathway. | 2001 May 15 |
|
| Excitotoxic injury stimulates pro-drug-induced 7-chlorokynurenate formation in the rat striatum in vivo. | 2001 May 25 |
|
| FcepsilonRI induces the tryptophan degradation pathway involved in regulating T cell responses. | 2002 Aug 15 |
|
| Novel protein modification by kynurenine in human lenses. | 2002 Feb 15 |
|
| [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 |
|
| "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 |
|
| More rapid method for simultaneous measurement of tryptophan and kynurenine by HPLC. | 2002 Mar |
|
| Excitatory and inhibitory responses of dopamine neurons in the ventral tegmental area to nicotine. | 2002 Mar 15 |
|
| 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 |
|
| CTLA-4-Ig regulates tryptophan catabolism in vivo. | 2002 Nov |
|
| Manipulation of brain kynurenines: glial targets, neuronal effects, and clinical opportunities. | 2002 Oct |
|
| 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 |
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 10:59:26 GMT 2023
by
admin
on
Sat Dec 16 10:59:26 GMT 2023
|
| Record UNII |
L47273GINT
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
m6646
Created by
admin on Sat Dec 16 10:59:26 GMT 2023 , Edited by admin on Sat Dec 16 10:59:26 GMT 2023
|
PRIMARY | Merck Index | ||
|
L47273GINT
Created by
admin on Sat Dec 16 10:59:26 GMT 2023 , Edited by admin on Sat Dec 16 10:59:26 GMT 2023
|
PRIMARY | |||
|
90478405
Created by
admin on Sat Dec 16 10:59:26 GMT 2023 , Edited by admin on Sat Dec 16 10:59:26 GMT 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
ANHYDROUS->SOLVATE |
