Xanthurenic acid

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Xanthurenic acid[1]
Xanthurenic acid.png
Names
IUPAC name
8-Hydroxy-4-oxo-1H-quinoline-2-carboxylic acid
Other names
Xanthuric acid
Xanthurenate
8-Hydroxykynurenic acid
4,8-Dihydroxyquinaldic acid
Identifiers
59-00-7 YesY
ChEBI CHEBI:10072 N
ChemSpider 5497 N
EC Number 200-410-1
Jmol 3D model Interactive image
KEGG C02470 N
PubChem 5699
  • InChI=1S/C10H7NO4/c12-7-3-1-2-5-8(13)4-6(10(14)15)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15) N
    Key: FBZONXHGGPHHIY-UHFFFAOYSA-N N
  • InChI=1/C10H7NO4/c12-7-3-1-2-5-8(13)4-6(10(14)15)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15)
    Key: FBZONXHGGPHHIY-UHFFFAOYAE
  • OC2=CC(C(O)=O)=NC1=C(O)C=CC=C12
Properties
C10H7NO4
Molar mass 205.17 g·mol−1
Appearance Yellow crystals
Melting point 286 °C (547 °F; 559 K)
Insoluble
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Xanthurenic acid, or xanthurenate, is a chemical shown to induce gametogenesis of Plasmodium falciparum, the parasite that causes malaria.[2][3] It is found in the gut of the Anopheles mosquito.

Xanthurenic acid is a metabolic intermediate that accumulates and is excreted by pyridoxine (vitamin B6) deficient animals after the ingestion of tryptophan.[1][4]

Xanthurenic acid is suspected to be an endogenous agonist for Group II metabotropic glutamate receptors in humans.[5] It is also known to be a potent VGLUT inhibitor, thereby preventing the movement of glutamate from the cytoplasm into synaptic vesicles, an action that it mediates via competitive blockade of vesicular glutamate transporters (Ki = 0.19 mM).[6] In 2015 researchers reported a marked reduction of xanthurenic acid levels in the serum of patients with schizophrenia, describing this phenomenon as a potential trait marker for schizophrenia.[7]

See also

References

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  1. ↑ 1.0 1.1 Merck Index, 11th Edition, 9977.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Xanthurenic acid at Sigma-Aldrich
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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