Common NameXanthurenate
DescriptionXanthurenic 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
Molecular FormulaC10H7NO4
Average Mass205.16690
Monoisotopic Mass205.03751
IUPAC Name4,8-dihydroxyquinoline-2-carboxylic acid
Traditional NameXanthurenic acid
CAS Registry Number59-00-7
SMILESO=C([O-])c1cc(O)c2cccc(O)c2n1
InChI IdentifierInChI=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 KeyFBZONXHGGPHHIY-UHFFFAOYSA-N
CHEBI IDCHEBI:71201
HMDB IDHMDB0000881
Pathways
NameSMPDB/PathBank
Tryptophan metabolism
StateNot Available
Water Solubility1.63e+00 g/l
logP2.01
logS-2.10
pKa (Strongest Acidic)1.12
pKa (Strongest Basic)5.30
Hydrogen Acceptor Count5
Hydrogen Donor Count3
Polar Surface Area90.65 Ų
Rotatable Bond Count1
Physiological Charge-1
Formal Charge0
Refractivity50.83 m³·mol⁻¹
Polarizability19.06

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