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Human Metabolome Database Version 2.5

 

Showing metabocard for Xanthurenic acid (HMDB00881)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2005-11-16 15:48:42
Update Date 2010-06-07 14:26:13
Accession Number HMDB00881
Secondary Accession Numbers Not Available
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).
Synonyms
  1. 4,8-Dihydroxy-2-quinolinecarboxylate
  2. 4,8-Dihydroxy-2-quinolinecarboxylic acid
  3. 4,8-Dihydroxyquinaldate
  4. 4,8-Dihydroxyquinaldic acid
  5. 4,8-Dihydroxyquinaldinate
  6. 4,8-Dihydroxyquinaldinic acid
  7. 4,8-Dihydroxyquinoline-2-carboxylate
  8. 4,8-Dihydroxyquinoline-2-carboxylic acid
  9. 4,8-dihydroxy-Quinaldate
  10. 4,8-dihydroxy-Quinaldic acid
  11. 8-Hydroxykynurenate
  12. 8-Hydroxykynurenic acid
  13. Xanthurate
  14. Xanthurenate
  15. Xanthuric acid;oxoxanthurenate
  16. 4-oxoxanthurenic acid
Chemical IUPAC Name 4,8-dihydroxy-quinoline-2-carboxylic acid
Chemical Formula C10H7NO4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Aromatic Acids
  • Hydroxy Acids
  • Isoquinolines and Quinolines
Sub Class
  • Heterocyclic acids
Family
  • Mammalian Metabolite
Species
  • phenol or hydroxyhetarene
  • carboxylic acid
  • aromatic compound
  • heterocyclic compound
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 205.167
Monoisotopic Molecular Weight 205.037506
Isomeric SMILES OC(=O)C1=NC2=C(O)C=CC=C2C(O)=C1
Canonical SMILES OC(=O)C1=NC2=C(O)C=CC=C2C(O)=C1
KEGG Compound ID C02470 Link Image
BioCyc ID XANTHURENATE Link Image
BiGG ID Not Available
Wikipedia Link Xanthurenic acid Link Image
NuGOwiki Link HMDB00881 Link Image
Metagene Link HMDB00881 Link Image
METLIN ID 5841 Link Image
PubChem Compound 5699 Link Image
PubChem Substance 5485 Link Image
ChEBI ID Not Available
CAS Registry Number 59-00-7
InChI Identifier InChI=1/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)
Synthesis Reference Furst, Arthur; Olsen, Carl J. A convenient synthesis of xanthurenic acid. Journal of Organic Chemistry (1951), 16 412-14.
Melting Point (Experimental) 289 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 5.89 mg/mL [MEYLAN,WM et al. (1996)]; 1.63 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 2.01 [Predicted by ALOGPS]; -1.5 [Predicted by PubChem via XLOGP]; 1.06 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Varian)
Show Experimental Conditions Link Image
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
Show Experimental Conditions Link Image
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
Show Experimental Conditions Link Image
High Energy
Download File
Show Experimental Conditions Link Image
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane
Biofluid Location
  • Blood
  • Urine
Tissue Location
Tissue References
Epidermis —
Concentrations (Normal)
Biofluid Blood
Value 0.022 +/- 0.001 uM
Age Adult:>18 yrs old
Sex N/A
Patient information Normal
Comments Not Available
References
  • 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 Link Image]
Biofluid Urine
Value 2.0 (0.0 - 4.0) umol/mmol creatinine
Age Children:1-13 yrs old
Sex N/A
Patient information Normal
Comments Not Available
References
  • 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 Link Image]
Biofluid Urine
Value 1.28 +/- 0.44 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by Cornelius Lentner.
  • West Cadwell, N.J. : Medical education Div., Ciba-Geigy Corp.
  • Basel, Switzerland c1981-1992.
Biofluid Urine
Value 0.10 +/- 0.17 umol/mmol creatinine
Age Infant:0-1 yr old
Sex Both
Patient information Normal
Comments Not Available
References
  • Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed Link Image]
Concentrations (Abnormal)
Biofluid Blood
Value 3.0 (2.0 - 4.0) uM
Age Children:1-13 yrs old
Sex N/A
Condition Kynureninase deficiency
Comments Not Available
References
  • 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 Link Image]
Biofluid Blood
Value 0.17 +/- 0.06 uM
Age Adult:>18 yrs old
Sex Both
Condition Hemodialysis
Comments Not Available
References
  • 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 Link Image]
Biofluid Urine
Value 200.0 (194.0 - 260.0) umol/mmol creatinine
Age Children:1-13 yrs old
Sex N/A
Condition Kynureninase deficiency
Comments Not Available
References
  • 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 Link Image]
Associated Disorders
Condition References
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 Link Image]
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 Link Image]
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Tryptophan Metabolism SMP00063 Link Image map00380 Link Image
General References
  1. 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 Link Image]
  2. 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 Link Image]
  3. 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 Link Image]
  4. Calandra P: Research on tryptophan metabolites "via kynurenine" in epidermis of man and mouse. Acta Vitaminol Enzymol. 1975;29(1-6):158-60. [PubMed Link Image]
  5. 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 Link Image]
  6. 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 Link Image]
  7. 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 Link Image]
  8. 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 Link Image]
  9. 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 Link Image]
  10. 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 Link Image]
  11. Wikipedia Link Image