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Identification
Name3-Hydroxyanthranilic Acid
Accession NumberDB03644  (EXPT00171)
TypeSmall Molecule
GroupsExperimental
Description

An oxidation product of tryptophan metabolism. It may be a free radical scavenger and a carcinogen. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
2-Amino-3-hydroxy-benzoic acidNot AvailableNot Available
2-Amino-3-Hydroxybenzoic AcidNot AvailableNot Available
3-HYDROXY-ANTHRANILATENot AvailableNot Available
3-Hydroxy-anthranilsaeureGermanNot Available
3-hydroxyanthranilateNot AvailableNot Available
3-Oxyanthranilic acidNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number548-93-6
WeightAverage: 153.1354
Monoisotopic: 153.042593095
Chemical FormulaC7H7NO3
InChI KeyWJXSWCUQABXPFS-UHFFFAOYSA-N
InChI
InChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11)
IUPAC Name
2-amino-3-hydroxybenzoic acid
SMILES
NC1=C(O)C=CC=C1C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHydroxybenzoic acid derivatives
Alternative Parents
Substituents
  • Hydroxybenzoic acid
  • Aminobenzoic acid or derivatives
  • Aminobenzoic acid
  • Benzoic acid
  • Substituted aniline
  • Benzoyl
  • Aminophenol
  • Phenol
  • Aniline
  • Primary aromatic amine
  • Vinylogous amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Tryptophan MetabolismMetabolicSMP00063
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8669
Blood Brain Barrier-0.9444
Caco-2 permeable-0.7319
P-glycoprotein substrateNon-substrate0.7997
P-glycoprotein inhibitor INon-inhibitor0.9834
P-glycoprotein inhibitor IINon-inhibitor0.9926
Renal organic cation transporterNon-inhibitor0.9565
CYP450 2C9 substrateNon-substrate0.7909
CYP450 2D6 substrateNon-substrate0.8414
CYP450 3A4 substrateNon-substrate0.7764
CYP450 1A2 substrateNon-inhibitor0.7645
CYP450 2C9 substrateNon-inhibitor0.8114
CYP450 2D6 substrateNon-inhibitor0.9735
CYP450 2C19 substrateNon-inhibitor0.6213
CYP450 3A4 substrateNon-inhibitor0.845
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9262
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.8719
BiodegradationReady biodegradable0.6606
Rat acute toxicity1.5446 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.964
hERG inhibition (predictor II)Non-inhibitor0.9446
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point240 °CNot Available
Predicted Properties
PropertyValueSource
Water Solubility10.5 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40 m3·mol-1ChemAxon
Polarizability14.18 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.79 KB)
SpectraGC-MSMS/MS1D NMR2D NMR
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (58.9 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Trans-2,3-dihydro-3-hydroxyanthranilate isomerase

Kind: protein

Organism: Pseudomonas fluorescens

Pharmacological action: unknown

Components

Name UniProt ID Details
Trans-2,3-dihydro-3-hydroxyanthranilate isomerase Q51792 Details

References:

  1. Blankenfeldt W, Kuzin AP, Skarina T, Korniyenko Y, Tong L, Bayer P, Janning P, Thomashow LS, Mavrodi DV: Structure and function of the phenazine biosynthetic protein PhzF from Pseudomonas fluorescens. Proc Natl Acad Sci U S A. 2004 Nov 23;101(47):16431-6. Epub 2004 Nov 15. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:22