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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:57:55 UTC
NP-MRD IDNP0000205
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Hydroxyanthranilic acid
Description3-Hydroxyanthranilic acid, also known as 2-amino-3-hydroxy-benzoate or 3-ohaa, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 3-Hydroxyanthranilic acid is a drug. 3-Hydroxyanthranilic acid exists in all living species, ranging from bacteria to humans. Within humans, 3-hydroxyanthranilic acid participates in a number of enzymatic reactions. In particular, 3-hydroxyanthranilic acid and L-alanine can be biosynthesized from L-3-hydroxykynurenine through the action of the enzyme kynureninase. In addition, 3-hydroxyanthranilic acid can be converted into cinnavalininate through the action of the enzyme catalase. 3-Hydroxyanthranilic acid is an intermediate in the metabolism of tryptophan. In humans, 3-hydroxyanthranilic acid is involved in tryptophan metabolism. Outside of the human body, 3-hydroxyanthranilic acid has been detected, but not quantified in brassicas. This could make 3-hydroxyanthranilic acid a potential biomarker for the consumption of these foods. It is new antioxidant isolated from methanol extract of tempeh. It is effective in preventing autoxidation of soybean oil and powder, while antioxidant 6,7,4'-trihydroxyisoflavone is not.
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
2-Amino-3-hydroxybenzoateGenerator
3-OxyanthranilateGenerator
3-HydroxyanthranilateGenerator
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 acidHMDB
Acid, 3-hydroxyanthranilicHMDB
Chemical FormulaC7H7NO3
Average Mass153.1354 Da
Monoisotopic Mass153.04259 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchos
Anatidae
Anser anser
Bison bison
Bos taurus
Bos taurus X Bison bison
Brassica oleraceaKNApSAcK Database
Bubalus bubalis
Capra aegagrus hircus
Cervidae
Cervus canadensis
Columba
Columbidae
Dromaius novaehollandiae
Equus caballus
Gallus gallus
Lagopus muta
Leporidae
Lepus timidus
Melanitta fusca
Meleagris gallopavo
Numida meleagris
Odocoileus
Oryctolagus
Ovis aries
Phasianidae
Phasianus colchicus
Struthio camelus
Sus scrofa
Sus scrofa domestica
Species Where Detected
Species NameSourceReference
Arthrobacter protophormiaeKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and 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
  • Vinylogous amide
  • Amino acid or derivatives
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Primary amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility12970 mg/L @ 25 °C (est)The Good Scents Company Information System
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001476
DrugBank IDDB03644
Phenol Explorer Compound 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 IDNot Available
ChEBI ID15793
Good Scents IDrw1190601
References
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 ]