Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H12N2O3 |
| Molecular Weight | 208.2139 |
| Optical Activity | UNSPECIFIED |
| 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-MRVPVSSYSA-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-/m1/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 |
D-kynurenine is metabolite of the amino acid D-tryptophan. D-kynurenine is an agonist for GPR109B (HM74), a putative G protein-coupled receptor. D-kynurenine elicits chemotactic responses in human neutrophils through GPR109B. D-amino acid oxidase can metabolize D-kynurenine to produce the fluorescent compound kynurenic acid.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22224417 | https://www.ncbi.nlm.nih.gov/pubmed/24158577
Curator's Comment: D-kynurenine was readily detected in the brain, liver, and plasma of mice treated systemically with D-kynurenine (300 mg/kg). In vivo, focal application of 100 μM D-kynurenine by reverse microdialysis led to a steady rise in extracellular kynurenic acid in the rat striatum, causing a 4-fold elevation after 2 h. Attesting to functional significance, this increase was accompanied by a 36% reduction in extracellular dopamine. No human data available.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Changes in the plasma concentrations of D-kynurenine and kynurenic acid in rats after intraperitoneal administration of tryptophan enantiomers. | 2010-11 |
|
| Changes in extracellular kynurenic acid concentrations in rat prefrontal cortex after D-kynurenine infusion: an in vivo microdialysis study. | 2010-04 |
|
| Tryptophan 2,3-dioxygenase is a key modulator of physiological neurogenesis and anxiety-related behavior in mice. | 2009-03-27 |
|
| Aromatic D-amino acids act as chemoattractant factors for human leukocytes through a G protein-coupled receptor, GPR109B. | 2009-03-10 |
|
| 3-[(3-Dehydroabietamidopropyl)dimethylammonio]-1-propane-sulfonate as a new type of chiral surfactant for enantiomer separation in micellar electrokinetic chromatography. | 2007-03-23 |
|
| Purification and biochemical characterization of some of the properties of recombinant human kynureninase. | 2002-04 |
| Substance Class |
Chemical
Created
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admin
on
Edited
Mon Mar 31 22:58:00 GMT 2025
by
admin
on
Mon Mar 31 22:58:00 GMT 2025
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| Record UNII |
DK8PQD0WC5
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| Record Status |
Validated (UNII)
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| Record Version |
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