xanthurenic acid (CHEBI:10072)

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ChEBI Name	xanthurenic acid

ChEBI ID	CHEBI:10072

Definition	A quinolinemonocarboxylic acid that is quinoline-2-carboxylic acid substituted by hydroxy groups at C-4 and C-8.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ChemicalBook:CB7180163, eMolecules:533336, ZINC000008738372

Download	Molfile XML SDF

Wikipedia	License
Xanthurenic acid, or xanthurenate, is a metabolic intermediate that accumulates and is excreted by pyridoxine (vitamin B6) deficient animals after the ingestion of tryptophan. Xanthurenic acid is suspected to be an endogenous agonist for Group II metabotropic glutamate receptors in humans. 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). In 2015 researchers reported a marked reduction of xanthurenic acid levels in the serum of patients with schizophrenia. A recent meta-analysis showed that blood xanthurenic acid levels are lower in individuals suffering from bipolar disorder as well. Xanthurenic acid has also been shown to induce gametogenesis of Plasmodium falciparum, the parasite that causes malaria. It is found in the gut of the Anopheles mosquito.
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Formula

C10H7NO4

Net Charge

Average Mass

205.16690

Monoisotopic Mass

205.03751

InChI

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)

InChIKey

FBZONXHGGPHHIY-UHFFFAOYSA-N

SMILES

OC(=O)c1cc(O)c2cccc(O)c2n1

Metabolite of Species	Details
Aedes aegypti (NCBI:txid7159)	See: PubMed

Roles Classification
Chemical Role(s):	iron chelator Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	metabotropic glutamate receptor agonist An agonist that selectively binds to and activates a metabotropic glutamate receptor. vesicular glutamate transport inhibitor An inhibitor that interferes with vesicular glutamate transport. animal metabolite Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.

ChEBI Ontology
Outgoing	xanthurenic acid (CHEBI:10072) has role animal metabolite (CHEBI:75767) xanthurenic acid (CHEBI:10072) has role iron chelator (CHEBI:38157) xanthurenic acid (CHEBI:10072) has role metabotropic glutamate receptor agonist (CHEBI:61966) xanthurenic acid (CHEBI:10072) has role vesicular glutamate transport inhibitor (CHEBI:72483) xanthurenic acid (CHEBI:10072) is a dihydroxyquinoline (CHEBI:26507) xanthurenic acid (CHEBI:10072) is a quinolinemonocarboxylic acid (CHEBI:26512) xanthurenic acid (CHEBI:10072) is conjugate acid of xanthurenate (CHEBI:71201)

Incoming	quinolobactin (CHEBI:171659) has functional parent xanthurenic acid (CHEBI:10072) xanthurenate (CHEBI:71201) is conjugate base of xanthurenic acid (CHEBI:10072)

IUPAC Name

4,8-dihydroxyquinoline-2-carboxylic acid

Last Modified

29 April 2021