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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:37 UTC
HMDB IDHMDB01476
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Hydroxyanthranilic acid
Description3-Hydroxyanthranilic acid is an oxidation product of tryptophan metabolism. It may be a free radical scavenger and a carcinogen.
Structure
Thumb
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 FormulaC7H7NO3
Average Molecular Weight153.1354
Monoisotopic Molecular Weight153.042593095
IUPAC Name2-amino-3-hydroxybenzoic acid
Traditional Name3-hydroxyanthranilic acid
CAS Registry Number548-93-6
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 KeyWJXSWCUQABXPFS-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassBenzoic Acid and Derivatives
Sub ClassHydroxybenzoic 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 ParentHydroxybenzoic Acid Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Tryptophan metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility10.5 g/LALOGPS
logP0.81ALOGPS
logP1.15ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.94ChemAxon
pKa (Strongest Basic)4.82ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40ChemAxon
Polarizability14.18ChemAxon
Spectra
SpectraGC-MSMS/MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Bladder
  • Epidermis
  • Lymphocyte
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063map00380
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.079 (0.015-0.209) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified3.28 (0.46-5.19) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.01 (0.007-0.011) uMAdult (>18 years old)BothStroke details
Associated Disorders and Diseases
Disease References
Stroke
  1. 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
Associated OMIM IDs
DrugBank IDDB03644
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB010582
KNApSAcK IDC00007568
Chemspider ID84
KEGG Compound IDC00632
BioCyc ID3-HYDROXY-ANTHRANILATE
BiGG ID1485273
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01476
Metagene LinkHMDB01476
METLIN ID3275
PubChem Compound86
PDB ID3HA
ChEBI ID15793
References
Synthesis ReferenceWarnell, J. L. 3-Hydroxyanthranilic acid. Biochemical Preparations (1958), 6 20-4.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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
  2. 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
  3. 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
  4. 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
  5. 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
  6. 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
  7. 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
  8. 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
  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

Enzymes

General function:
Involved in metabolic process
Specific function:
Catalyzes the cleavage of L-kynurenine (L-Kyn) and L-3-hydroxykynurenine (L-3OHKyn) into anthranilic acid (AA) and 3-hydroxyanthranilic acid (3-OHAA), respectively. Has a preference for the L-3-hydroxy form. Also has cysteine-conjugate-beta-lyase activity.
Gene Name:
KYNU
Uniprot ID:
Q16719
Molecular weight:
34634.47
Reactions
L-3-Hydroxykynurenine + Water → 3-Hydroxyanthranilic acid + L-Alaninedetails
General function:
Involved in 3-hydroxyanthranilate 3,4-dioxygenase activity
Specific function:
Catalyzes the oxidative ring opening of 3-hydroxyanthranilate to 2-amino-3-carboxymuconate semialdehyde, which spontaneously cyclizes to quinolinate.
Gene Name:
HAAO
Uniprot ID:
P46952
Molecular weight:
32555.935
Reactions
3-Hydroxyanthranilic acid + Oxygen → 2-Amino-3-carboxymuconic acid semialdehydedetails
General function:
Involved in catalase activity
Specific function:
Occurs in almost all aerobically respiring organisms and serves to protect cells from the toxic effects of hydrogen peroxide. Promotes growth of cells including T-cells, B-cells, myeloid leukemia cells, melanoma cells, mastocytoma cells and normal and transformed fibroblast cells.
Gene Name:
CAT
Uniprot ID:
P04040
Molecular weight:
59755.82
Reactions
3-Hydroxyanthranilic acid + Oxygen → Cinnavalininate + Superoxide + Hydrogen peroxide + Hydrogen Iondetails
General function:
Not Available
Specific function:
N5-glutamine methyltransferase responsible for the methylation of the GGQ triplet of the mitochondrial translation release factor MTRF1L.
Gene Name:
HEMK1
Uniprot ID:
Q9Y5R4
Molecular weight:
Not Available
Reactions
3-Hydroxyanthranilic acid + S-Adenosylmethionine → 3-Methoxyanthranilate + S-Adenosylhomocysteinedetails
General function:
Not Available
Specific function:
Probable methyltransferase (By similarity).
Gene Name:
METTL2B
Uniprot ID:
Q6P1Q9
Molecular weight:
Not Available
Reactions
3-Hydroxyanthranilic acid + S-Adenosylmethionine → 3-Methoxyanthranilate + S-Adenosylhomocysteinedetails
General function:
Not Available
Specific function:
Probable methyltransferase (By similarity).
Gene Name:
METTL6
Uniprot ID:
Q8TCB7
Molecular weight:
Not Available
Reactions
3-Hydroxyanthranilic acid + S-Adenosylmethionine → 3-Methoxyanthranilate + S-Adenosylhomocysteinedetails
General function:
Not Available
Specific function:
Methyltransferase that may act on DNA.
Gene Name:
WBSCR22
Uniprot ID:
O43709
Molecular weight:
Not Available
Reactions
3-Hydroxyanthranilic acid + S-Adenosylmethionine → 3-Methoxyanthranilate + S-Adenosylhomocysteinedetails