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Human Metabolome Database Version 3.5

Showing metabocard for Xanthurenic acid (HMDB00881)

• Identification
• Taxonomy
• Ontology
• Physical properties
• Spectra
• Biological properties
• Concentrations
• Links
• References

enzymes (4)

• Blood
• Urine

Record Information
Version	3.5
Creation Date	2005-11-16 08:48:42 -0700
Update Date	2013-02-08 17:09:30 -0700
HMDB ID	HMDB00881
Secondary Accession Numbers	None
Metabolite Identification
Common Name	Xanthurenic acid
Description	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	Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure
Synonyms	4,8-Dihydroxy-2-quinolinecarboxylate 4,8-Dihydroxy-2-quinolinecarboxylic acid 4,8-Dihydroxy-Quinaldate 4,8-Dihydroxy-Quinaldic acid 4,8-Dihydroxyquinaldate 4,8-Dihydroxyquinaldic acid 4,8-Dihydroxyquinaldinate 4,8-Dihydroxyquinaldinic acid 4,8-Dihydroxyquinoline-2-carboxylate 4,8-Dihydroxyquinoline-2-carboxylic acid 4-Oxoxanthurenic acid 8-Hydroxykynurenate 8-Hydroxykynurenic acid Oxoxanthurenate Xanthurate Xanthurenate Xanthuric acid
Chemical Formula	C10H7NO4
Average Molecular Weight	205.1669
Monoisotopic Molecular Weight	205.037507717
IUPAC Name	4,8-dihydroxyquinoline-2-carboxylic acid
Traditional IUPAC 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
Kingdom	Organic Compounds
Super Class	Amino Acids, Peptides, and Analogues
Class	Amino Acids and Derivatives
Sub Class	Alpha Amino Acids and Derivatives
Other Descriptors	Aromatic Heteropolycyclic Compounds
Substituents	Carboxylic Acid Hydroxyquinoline Phenol Phenol Derivative Pyridine Pyridine Carboxylic Acid Quinoline
Direct Parent	Alpha Amino Acids and Derivatives
Ontology
Status	Detected and Quantified
Origin	Endogenous
Biofunction	Not Available
Application	Not Available
Cellular locations	Membrane
Physical Properties
State	Solid
Experimental Properties	Property Value Reference Melting Point 289 °C Not Available Boiling Point Not Available Not Available Water Solubility Not Available Not Available LogP Not Available Not Available
Predicted Properties	Property Value Source Water Solubility 1.63 g/L ALOGPS LogP 2.01 ALOGPS LogP 0.78 ChemAxon LogS -2.10 ALOGPS pKa (strongest acidic) 1.12 ChemAxon pKa (strongest basic) 5.3 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 90.65 A2 ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 50.83 ChemAxon Polarizability 19.06 ChemAxon Formal Charge 0 ChemAxon Physiological Charge -1 ChemAxon
Spectra
	Gas-MS Spectrum 1H NMR Spectrum MS/MS Spectrum Quattro_QQQ 10 MS/MS Spectrum Quattro_QQQ 25 MS/MS Spectrum Quattro_QQQ 40 MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10 MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20 MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30 MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40 MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50 MS/MS Spectrum LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies ) MS/MS Spectrum GC-MS [1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations	Membrane
Biofluid Locations	Blood Urine
Tissue Location	Epidermis
Pathways	Name SMPDB Link KEGG Link Tryptophan Metabolism SMP00063 map00380
Normal Concentrations
	Biofluid Status Value Age Sex Condition Reference Blood Detected and Quantified 0.022 +/- 0.001 uM Adult (>18 years old) Not Specified Normal 12092667 Urine Detected and Quantified 1.28 +/- 0.44 umol/mmol creatinine Adult (>18 years old) Both Normal Geigy Scient... West Cadwell... Basel, Switz... Urine Detected and Quantified 2.0 (0.0 - 4.0) umol/mmol creatinine Children (1-13 year old) Not Specified Normal 17334708 Urine Detected and Quantified 0.10 +/- 0.17 umol/mmol creatinine Infant (0-1 year old) Both Normal 2026685
Abnormal Concentrations
	Biofluid Status Value Age Sex Condition Reference Blood Detected and Quantified 0.17 +/- 0.06 uM Adult (>18 years old) Both Hemodialysis 12092667 Blood Detected and Quantified 3.0 (2.0 - 4.0) uM Children (1-13 year old) Not Specified Kynureninase deficiency 17334708 Urine Detected and Quantified 200.0 (194.0 - 260.0) umol/mmol creatinine Children (1-13 year old) Not Specified Kynureninase deficiency 17334708
Associated Disorders and Diseases
Disease References	Kynureninase deficiency Christensen M, Duno M, Lund AM, Skovby F, Christensen E: Xanthurenic aciduria due to a mutation in KYNU encoding kynureninase. J Inherit Metab Dis. 2007 Apr;30(2):248-55. Epub 2007 Mar 1. Pubmed: 17334708 Hemodialysis Pawlak D, Pawlak K, Malyszko J, Mysliwiec M, Buczko W: Accumulation of toxic products degradation of kynurenine in hemodialyzed patients. Int Urol Nephrol. 2001;33(2):399-404. Pubmed: 12092667
Associated OMIM IDs	None
External Links
DrugBank ID	Not Available
DrugBank Metabolite ID	Not Available
Phenol Explorer Compound ID	Not Available
Phenol Explorer Metabolite ID	Not Available
FoodDB ID	FDB022297
KNApSAcK ID	Not Available
Chemspider ID	5497
KEGG Compound ID	C02470
BioCyc ID	XANTHURENATE
BiGG ID	Not Available
Wikipedia Link	Xanthurenic acid
NuGOwiki Link	HMDB00881
Metagene Link	HMDB00881
METLIN ID	5841
PubChem Compound	5699
PDB ID	Not Available
ChEBI ID	217069
References
Synthesis Reference	Furst, Arthur; Olsen, Carl J. A convenient synthesis of xanthurenic acid. Journal of Organic Chemistry (1951), 16 412-14.
Material Safety Data Sheet (MSDS)	Download (PDF)
General References	Bapurao S, Krishnaswamy K: Vitamin B6 nutritional status of pellagrins and their leucine tolerance. Am J Clin Nutr. 1978 May;31(5):819-24. Pubmed: 206127 Shibata K, Fukuwatari T, Murakami M, Sasaki R: Increase in conversion of tryptophan to niacin in pregnant rats. Adv Exp Med Biol. 2003;527:435-41. Pubmed: 15206761 Forrest CM, Gould SR, Darlington LG, Stone TW: Levels of purine, kynurenine and lipid peroxidation products in patients with inflammatory bowel disease. Adv Exp Med Biol. 2003;527:395-400. Pubmed: 15206756 Calandra P: Research on tryptophan metabolites "via kynurenine" in epidermis of man and mouse. Acta Vitaminol Enzymol. 1975;29(1-6):158-60. Pubmed: 1244085 Hoes MJ, Loeffen T, Vree TB: Kinetics of L-tryptophan in depressive patients: a possible correlation between the plasma concentrations of L-tryptophan and some psychiatric rating scales. Psychopharmacology (Berl). 1981;75(4):350-3. Pubmed: 6803278 Malina HZ, Hess OM: Xanthurenic acid translocates proapoptotic Bcl-2 family proteins into mitochondria and impairs mitochondrial function. BMC Cell Biol. 2004 Apr 6;5:14. Pubmed: 15068490 Bapurao S, Raman L, Tulpule PG: Biochemical assessment of vitamin B6 nutritional status in pregnant women with orolingual manifestations. Am J Clin Nutr. 1982 Oct;36(4):581-6. Pubmed: 7124659 Malina HZ: Comment on 'The photosensitiser xanthurenic acid is not present in normal human lenses' by P.G. Hains et al. [Exp. Eye Res. 77 (2003) 547-553]. Exp Eye Res. 2004 Sep;79(3):443-5; author reply 447-8. Pubmed: 15336509 Forrest CM, Kennedy A, Stone TW, Stoy N, Darlington LG: Kynurenine and neopterin levels in patients with rheumatoid arthritis and osteoporosis during drug treatment. Adv Exp Med Biol. 2003;527:287-95. Pubmed: 15206742 Igari T, Tsuchizawa M, Shimamura T: Alteration of tryptophan metabolism in the synovial fluid of patients with rheumatoid arthritis and osteoarthritis. Tohoku J Exp Med. 1987 Oct;153(2):79-86. Pubmed: 3500530

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Enzymes
Name: HemK methyltransferase family member 1 Reactions: Xanthurenic acid + S-Adenosylmethionine unknown 8-Methoxykynurenate + S-Adenosylhomocysteine details Gene Name: HEMK1 Uniprot ID: Q9Y5R4
Name: Methyltransferase-like protein 2B Reactions: Xanthurenic acid + S-Adenosylmethionine unknown 8-Methoxykynurenate + S-Adenosylhomocysteine details Gene Name: METTL2B Uniprot ID: Q6P1Q9
Name: Methyltransferase-like protein 6 Reactions: Xanthurenic acid + S-Adenosylmethionine unknown 8-Methoxykynurenate + S-Adenosylhomocysteine details Gene Name: METTL6 Uniprot ID: Q8TCB7
Name: Uncharacterized methyltransferase WBSCR22 Reactions: Xanthurenic acid + S-Adenosylmethionine unknown 8-Methoxykynurenate + S-Adenosylhomocysteine details Gene Name: WBSCR22 Uniprot ID: O43709

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government.