Xanthurenic acid

Chemical compound From Wikipedia, the free encyclopedia

Xanthurenic acid, or xanthurenate, is a metabolic intermediate that accumulates and is excreted by pyridoxine (vitamin B6) deficient animals after the ingestion of tryptophan.[1][2]

Quick facts Names, Identifiers ...
Xanthurenic acid[1]
Names
Preferred IUPAC name
4,8-Dihydroxyquinoline-2-carboxylic acid
Other names
Xanthuric acid
Xanthurenate
8-Hydroxykynurenic acid
4,8-Dihydroxyquinaldic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.000.373 Edit this at Wikidata
EC Number
  • 200-410-1
KEGG
UNII
  • 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 205.169 g·mol−1
Appearance Yellow crystals
Melting point 286 °C (547 °F; 559 K)
Insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Xanthurenic acid is suspected to be an endogenous agonist for Group II metabotropic glutamate receptors in humans.[3] 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).[4]

In 2015 researchers reported a marked reduction of xanthurenic acid levels in the serum of patients with schizophrenia.[5] A recent meta-analysis showed that blood xanthurenic acid levels are lower in individuals suffering from bipolar disorder as well.[6]

Xanthurenic acid has also been shown to induce gametogenesis of Plasmodium falciparum, the parasite that causes malaria.[7][8] It is found in the gut of the Anopheles mosquito.

See also

References

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