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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 08:24:07 UTC
HMDB IDHMDB0001476
Secondary Accession Numbers
  • HMDB01476
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
ValueSource
2-amino-3-Hydroxy-benzoic acidChEBI
2-amino-3-Hydroxybenzoic acidChEBI
3-OhaaChEBI
3-Oxyanthranilic acidChEBI
2-amino-3-Hydroxy-benzoateGenerator
3-HydroxyanthranilateGenerator
2-amino-3-HydroxybenzoateGenerator
3-OxyanthranilateGenerator
3-HydroxanthranilateHMDB
3-Hydroxy-2-aminobenzoateHMDB
3-Hydroxy-2-aminobenzoic acidHMDB
3-Hydroxy-anthranilateHMDB
3-Hydroxy-anthranilic acidHMDB
3-Hydroxy-anthranilsaeureHMDB
3-Hydroxyantranilic acidHMDB
3-OH-Anthranilic acidHMDB
3 Hydroxyanthranilic acidMeSH
Acid, 3-hydroxyanthranilicMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as hydroxybenzoic acid derivatives. These are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentHydroxybenzoic acid derivatives
Alternative Parents
Substituents
  • Aminobenzoic acid
  • Aminobenzoic acid or derivatives
  • Hydroxybenzoic acid
  • Benzoic acid
  • O-aminophenol
  • Aminophenol
  • Benzoyl
  • Aniline or substituted anilines
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Primary aromatic amine
  • Vinylogous amide
  • Amino acid
  • Amino acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Primary amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Amine
  • Organic oxide
  • Organic nitrogen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

  Health condition:

    Nervous system disorders:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

  Tissue and substructures:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Industrial application:

  Pharmaceutical industry:

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 Area83.55 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40 m³·mol⁻¹ChemAxon
Polarizability14.18 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0zfv-0945000000-e3389ab25b7133eb184dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0zfu-1955000000-fd51cc45bf09750e2b48View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0zfv-0945000000-e3389ab25b7133eb184dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0zfu-1955000000-fd51cc45bf09750e2b48View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0zfv-0934000000-11e2b38a36cb364bcaf3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0920000000-a57d310e9ca51aefd0c1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-2313e347dd8659099393View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9400000000-4e342fdebc8145b606a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-ee5255b437ae762be1f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000t-2900000000-a68dc7ca20e1f9595f15View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0zfr-0900000000-ced0a738a11057bc94e4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0900000000-cded3154e50c6169c670View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0900000000-9c388fc3035f19e3f156View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-1900000000-9dbb06a7728aab173e0fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0a4i-0900000000-19cfe2cda31cf7284669View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-02ae2bd70b54df77aca5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-56e21a4ececd5541a7d8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-052r-0900000000-e3015612b3d263fabaa9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a5i-3900000000-670c7d91a38e852d8e4cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-5900000000-36b3a876d06807eb22a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-84ae4ad8e91e8e4b6a6bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k9i-1900000000-6695f66ad1f45898b8b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pxr-9300000000-43045627b8c856bf07d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-0900000000-810a4a12ecb151ecb516View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1900000000-9f194909a88a4ac248b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-8900000000-608d595690e7902b6195View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Bladder
  • Epidermis
  • Lymphocyte
Pathways
NameSMPDB/PathwhizKEGG
Tryptophan MetabolismPw000163Pw000163 greyscalePw000163 simpleMap00380
Displaying 1 entry
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 Link3-hydroxyanthranilic_acid
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