ChemFOnt: Showing chemical card for Xanthurenic acid (CFc000000703)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:10 UTC

Chemfont ID

CFc000000703

Molecule Identification

Common Name

Xanthurenic acid

Definition

Xanthurenic acid, also known as xanthurenate or 8-hydroxykynurenic acid, is a member of the class of compounds known as quinoline carboxylic acids. Quinoline carboxylic acids are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions. Xanthurenic acid is slightly soluble (in water). Xanthurenic acid can be found primarily in blood, feces, and urine, as well as in human epidermis tissue. Within the cell, xanthurenic acid is primarily located in the membrane. Xanthurenic acid exists in all eukaryotes, ranging from yeast to humans. In humans, xanthurenic acid is involved in the tryptophan metabolism. Moreover, xanthurenic acid is found to be associated with citrullinemia type I, which is an inborn error of metabolism. Xanthurenic acid is a metabolite from tryptophan catabolism. It is a substrate of the enzyme methyltransferases (EC 2.1.1.-) in pathway tryptophan metabolism (KEGG).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Xanthurenate	Kegg
8-Hydroxykynurenic acid	HMDB
Gametocyte activating factor (gaf)	HMDB
4,8-Dihydroxy-2-quinolinecarboxylate	HMDB
4,8-Dihydroxy-2-quinolinecarboxylic acid	HMDB
4,8-Dihydroxy-quinaldate	HMDB
4,8-Dihydroxy-quinaldic acid	HMDB
4,8-Dihydroxyquinaldate	HMDB
4,8-Dihydroxyquinaldic acid	HMDB
4,8-Dihydroxyquinaldinate	HMDB
4,8-Dihydroxyquinaldinic acid	HMDB
4,8-Dihydroxyquinoline-2-carboxylate	HMDB
4,8-Dihydroxyquinoline-2-carboxylic acid	HMDB
4-Oxoxanthurenic acid	HMDB
8-Hydroxykynurenate	HMDB
Oxoxanthurenate	HMDB
Xanthurate	HMDB
Xanthuric acid	HMDB

Chemical Formula

C₁₀H₇NO₄

Average Molecular Weight

205.1669

Monoisotopic Molecular Weight

205.037507717

IUPAC Name

4,8-dihydroxyquinoline-2-carboxylic acid

Traditional Name

xanthurenic acid

CAS Registry Number

59-00-7

SMILES

OC(=O)C1=NC2=C(O)C=CC=C2C(O)=C1

InChI Identifier

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)

InChI Key

FBZONXHGGPHHIY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinoline carboxylic acids

Direct Parent

Quinoline carboxylic acids

Alternative Parents

Substituents

Quinoline-2-carboxylic acid
Dihydroquinolone
Hydroxyquinoline
8-hydroxyquinoline
Dihydroquinoline
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinolinemonocarboxylic acid (CHEBI:10072 )
dihydroxyquinoline (CHEBI:10072 )

Functional Ontology

Physiological effect

Health effect

Intervention

Hemodialysis (HMDB: HMDB0000881)

Genetic disorder

Inborn errors of metabolism

Kynureninase deficiency (HMDB: HMDB0000881)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17334708)

Cellular substructure

Membrane (HMDB: HMDB0000881)
Cell membrane (HMDB: HMDB0000881)

Tissue

Epithelium

Epidermis (HMDB: HMDB0000881)

Excreta

Biofluid or Excreta

Urine (PMID: 17334708)
Feces (PMID: 27786174)

Source

Endogenous

Endogenous (HMDB: HMDB0000881)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tryptophan Metabolism (PathBank: SMP0063693)
Tryptophan Metabolism (HMDB: HMDB0000881)

Role

Industrial application

Pharmaceutical industry

Biomarker

Eosinophilic esophagitis (MarkerDB: MDB00000273)
Kynureninase deficiency (MarkerDB: MDB00000273)
Hemodialysis (MarkerDB: MDB00000273)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.63 g/L	ALOGPS
logP	2.01	ALOGPS
logP	-0.17	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.14	ChemAxon
pKa (Strongest Basic)	5.75	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.65 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	50.83 m³·mol⁻¹	ChemAxon
Polarizability	19.06 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon