Compound: xanthurenic acid
SMILES: O=C(O)c1nc2c(O)cccc2c(c1)O
InChIKey: FBZONXHGGPHHIY-UHFFFAOYSA-N
Synonyms: xanthurenic acid, 59-00-7, 4,8-Dihydroxyquinoline-2-carboxylic acid, Xanthuric acid, 8-Hydroxykynurenic acid, 4,8-Dihydroxyquinaldic acid, 8-hydroxy-4-oxo-1H-quinoline-2-carboxylic acid, 58LAB1BG8J, DTXSID90207728, NSC-401570, CHEBI:10072, RefChem:902266, DTXCID40130219, 200-410-1, Xanthurenate, 4,8-Dihydroxyquinaldinic acid, 2-Quinolinecarboxylic acid, 4,8-dihydroxy-, 4,8-Dihydroxy-2-quinolinecarboxylic acid, MFCD00006754, 8-hydroxy-4-oxo-1,4-dihydroquinoline-2-carboxylic acid, NSC 401570, NSC401570, QUINALDIC ACID, 4,8-DIHYDROXY-, CHEMBL312535, 67283-71-0, CCRIS 4429, 4,8-Dihydroxyquinoline-2-carboxylate, EINECS 200-410-1, UNII-58LAB1BG8J, BRN 0185954, Oxoxanthurenate, Xanthurate, 8-Hydroxykynurenate, 4-oxoxanthurenic acid, Spectrum_000253, 4,8-Dihydroxyquinaldate, Xanthurenic acid, 96%, Spectrum2_000158, Spectrum3_000143, Spectrum4_000117, Spectrum5_001562, 4,8-dihydroxy-Quinaldate, 4,8-Dihydroxyquinaldinate, Xanthurenic acid (Standard), Quinaldic acid,8-dihydroxy-, Oprea1_107134, BSPBio_001846, KBioGR_000474, KBioSS_000733, 4,8-dihydroxy-Quinaldic acid, BIDD:GT0640, DivK1c_000262, SCHEMBL379760, SPECTRUM1500754, XANTHURENIC ACID [MI], SPBio_000296, orb1304625, orb3141469, SCHEMBL4455363, SCHEMBL29394132, SCHEMBL29911018, HMS500N04, KBio1_000262, KBio2_000733, KBio2_003301, KBio2_005869, KBio3_001046, NINDS_000262, HMS1921G08, HMS3885N22, WLN: T66 BNJ CVQ EQ JQ, HY-W014666R, 4,8-dihydroxyquinoline-2-carboxylic, BDBM50113313, CCG-38363, EBC-76176, HB0659, s4774, SBB003498, 4,8-Dihydroxy-2-quinolinecarboxylate, AKOS003237896, AKOS015894330, 4,8-dihydroxyquinolinium-2-carboxylate, CS-W015382, FX28736, HY-W014666, MSK163144-100M, SB72014, SDCCGMLS-0066616.P001, 2-Quinolinecarboxylic acid,8-dihydroxy-, IDI1_000262, NCGC00094846-01, NCGC00094846-02, NCGC00094846-03, NCGC00094846-04, NCGC00094846-05, AS-56782, BP-10912, DB-053303, NS00014990, ST45025626, X0054, Quinoline-2-carboxylic acid, 4,8-dihydroxy-, C02470, 4,8-Dihydroxy-quinoline-2-carboxylic acid anion, Xanthurenic acid Solution in Methanol, 100ug/mL, F340043, SR-05000002445, CU-01000012491-3, Q5961262, SR-05000002445-1, BRD-K07327532-001-03-6, 4,8-Dihydroxy-quinoline-2-carboxylic acid(Xanthurenate), B5FF212D-76CB-4875-8A36-C67D8E69489C, Xanthurenate; 8-Hydroxykynurenic acid; 4,8-Dihydroxyquinaldic acid, 4KL
Theoretical properties:
molecular_formula: C10H7NO4
molecular_weight: 205.17 g/mol
exact_mass: 205.03750770 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 1
heavy_atom_count: 15
topological_polar_surface_area: 86.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 289 °C
Descriptions:
pubchem: Xanthurenic acid is a quinolinemonocarboxylic acid that is quinoline-2-carboxylic acid substituted by hydroxy groups at C-4 and C-8. It has a role as an iron chelator, a metabotropic glutamate receptor agonist, a vesicular glutamate transport inhibitor and an animal metabolite. It is a dihydroxyquinoline and a quinolinemonocarboxylic acid. It is a conjugate acid of a xanthurenate.
chebi: A quinolinemonocarboxylic acid that is quinoline-2-carboxylic acid substituted by hydroxy groups at C-4 and C-8.
chembl: XANTHURENATE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: 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.