Human Metabolome Database Version 3.5

Showing metabocard for 3-Hydroxyanthranilic acid (HMDB01476)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:37 -0700
HMDB ID HMDB01476
Secondary Accession Numbers None
Metabolite Identification
Common Name 3-Hydroxyanthranilic acid
Description 3-Hydroxyanthranilic acid is an oxidation product of tryptophan metabolism. It may be a free radical scavenger and a carcinogen.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2-Amino-3-hydroxy-Benzoate
  2. 2-Amino-3-hydroxy-Benzoic acid
  3. 2-Amino-3-hydroxybenzoate
  4. 2-Amino-3-hydroxybenzoic acid
  5. 3-Hydroxanthranilate
  6. 3-Hydroxy-2-aminobenzoate
  7. 3-Hydroxy-2-aminobenzoic acid
  8. 3-Hydroxy-Anthranilate
  9. 3-Hydroxy-Anthranilic acid
  10. 3-Hydroxy-anthranilsaeure
  11. 3-Hydroxyanthranilate
  12. 3-Hydroxyanthranilic acid
  13. 3-Hydroxyantranilic acid
  14. 3-OH-anthranilic acid
  15. 3-OHAA
  16. 3-Oxyanthranilate
  17. 3-Oxyanthranilic acid
Chemical Formula C7H7NO3
Average Molecular Weight 153.1354
Monoisotopic Molecular Weight 153.042593095
IUPAC Name 2-amino-3-hydroxybenzoic acid
Traditional IUPAC Name 3-hydroxyanthranilic acid
CAS Registry Number 548-93-6
SMILES NC1=C(O)C=CC=C1C(O)=O
InChI Identifier InChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11)
InChI Key WJXSWCUQABXPFS-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Benzoic Acid and Derivatives
Sub Class Hydroxybenzoic Acid Derivatives
Other Descriptors
  • Aminobenzoic Acid Derivatives
  • Organic Compounds
  • aminobenzoic acid(ChEBI)
  • benzoic acids(ChEBI)
Substituents
  • Aminophenol Derivative
  • Aniline
  • Benzoyl
  • Carboxylic Acid
  • Phenol
  • Phenol Derivative
Direct Parent Hydroxybenzoic Acid Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Tryptophan metabolism
Application Not Available
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available 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 10.5 g/L ALOGPS
LogP 0.81 ALOGPS
LogP 1.15 ChemAxon
LogS -1.16 ALOGPS
pKa (strongest acidic) 1.94 ChemAxon
pKa (strongest basic) 4.82 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 83.55 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 40 ChemAxon
Polarizability 14.18 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
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
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Bladder
  • Lymphocyte
  • Epidermis
Pathways
Name SMPDB Link KEGG Link
Tryptophan Metabolism SMP00063 map00380 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.079 (0.015-0.209) uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
3.28 (0.46-5.19) umol/mmol creatinine Adult (>18 years old) Both Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.01 (0.007-0.011) uM Adult (>18 years old) Both Stroke
Associated Disorders and Diseases
Disease References
Stroke
  • Darlington LG, Mackay GM, Forrest CM, Stoy N, George C, Stone TW: Altered kynurenine metabolism correlates with infarct volume in stroke. Eur J Neurosci. 2007 Oct;26(8):2211-21. Epub 2007 Sep 24. Pubmed: 17892481 Link_out
      Associated OMIM IDs
      DrugBank ID DB03644 Link_out
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB010582
      KNApSAcK ID C00007568 Link_out
      Chemspider ID 84 Link_out
      KEGG Compound ID C00632 Link_out
      BioCyc ID 3-HYDROXY-ANTHRANILATE Link_out
      BiGG ID 1485273 Link_out
      Wikipedia Link Not Available
      NuGOwiki Link HMDB01476 Link_out
      Metagene Link HMDB01476 Link_out
      METLIN ID 3275 Link_out
      PubChem Compound 86 Link_out
      PDB ID 3HA Link_out
      ChEBI ID 15793 Link_out
      References
      Synthesis Reference Warnell, J. L. 3-Hydroxyanthranilic acid. Biochemical Preparations (1958), 6 20-4.
      Material Safety Data Sheet (MSDS) Download (PDF)
      General References
      1. 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 Link_out
      2. Werner ER, Lutz H, Fuchs D, Hausen A, Huber C, Niederwieser D, Pfleiderer W, Reibnegger G, Troppmair J, Wachter H: Identification of 3-hydroxyanthranilic acid in mixed lymphocyte cultures. Biol Chem Hoppe Seyler. 1985 Jan;366(1):99-102. Pubmed: 3159398 Link_out
      3. Teulings FA, Mulder-Kooy GE, Peters HA, Fokkens W, Van Der Werf-Messing B: The excretion of 3-hydroxyanthranilic acid in patients with bladder and kidney carcinoma. Acta Vitaminol Enzymol. 1975;29(1-6):108-12. Pubmed: 1244078 Link_out
      4. De Antoni A, Rubaltelli FF, Costa C, Allegri G: Effect of phototherapy on the urinary excretion of tryptophan metabolites in neonatal hyperbilirubinemia. Acta Vitaminol Enzymol. 1975;29(1-6):145-50. Pubmed: 1244083 Link_out
      5. Lopez AS, Alegre E, LeMaoult J, Carosella E, Gonzalez A: Regulatory role of tryptophan degradation pathway in HLA-G expression by human monocyte-derived dendritic cells. Mol Immunol. 2006 Jul;43(14):2151-60. Epub 2006 Feb 21. Pubmed: 16490253 Link_out
      6. Yeh JK, Brown RR: Effects of vitamin B-6 deficiency and tryptophan loading on urinary excretion of tryptophan metabolites in mammals. J Nutr. 1977 Feb;107(2):261-71. Pubmed: 833687 Link_out
      7. Herve C, Beyne P, Jamault H, Delacoux E: Determination of tryptophan and its kynurenine pathway metabolites in human serum by high-performance liquid chromatography with simultaneous ultraviolet and fluorimetric detection. J Chromatogr B Biomed Appl. 1996 Jan 12;675(1):157-61. Pubmed: 8634758 Link_out
      8. Hegedus ZL, Frank HA, Altschule MD, Nayak U: Human plasma lipofuscin melanins formed from tryptophan metabolites. Arch Int Physiol Biochim. 1986 Dec;94(5):339-48. Pubmed: 2440410 Link_out
      9. Teulings FA, Lems PH, Portengen H, Henkelman MS, Blonk DI: The action of 3-hydroxyanthranilic acid and other tryptophan metabolites on stimulated human lymphocytes. Acta Vitaminol Enzymol. 1975;29(1-6):113-6. Pubmed: 1244079 Link_out

      Enzymes
      Name: Kynureninase
      Reactions:
      L-3-Hydroxykynurenine + Water unknown 3-Hydroxyanthranilic acid + L-Alanine details
      Gene Name: KYNU
      Uniprot ID: Q16719 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: 3-hydroxyanthranilate 3,4-dioxygenase
      Reactions:
      3-Hydroxyanthranilic acid + Oxygen unknown 2-Amino-3-carboxymuconic acid semialdehyde details
      Gene Name: HAAO
      Uniprot ID: P46952 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Catalase
      Reactions:
      3-Hydroxyanthranilic acid + Oxygen unknown Cinnavalininate + Superoxide + Hydrogen peroxide + Hydrogen Ion details
      Gene Name: CAT
      Uniprot ID: P04040 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: HemK methyltransferase family member 1
      Reactions:
      3-Hydroxyanthranilic acid + S-Adenosylmethionine unknown 3-Methoxyanthranilate + S-Adenosylhomocysteine details
      Gene Name: HEMK1
      Uniprot ID: Q9Y5R4 Link_out
      Name: Methyltransferase-like protein 2B
      Reactions:
      3-Hydroxyanthranilic acid + S-Adenosylmethionine unknown 3-Methoxyanthranilate + S-Adenosylhomocysteine details
      Gene Name: METTL2B
      Uniprot ID: Q6P1Q9 Link_out
      Name: Methyltransferase-like protein 6
      Reactions:
      3-Hydroxyanthranilic acid + S-Adenosylmethionine unknown 3-Methoxyanthranilate + S-Adenosylhomocysteine details
      Gene Name: METTL6
      Uniprot ID: Q8TCB7 Link_out
      Name: Uncharacterized methyltransferase WBSCR22
      Reactions:
      3-Hydroxyanthranilic acid + S-Adenosylmethionine unknown 3-Methoxyanthranilate + S-Adenosylhomocysteine details
      Gene Name: WBSCR22
      Uniprot ID: O43709 Link_out