You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
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
SaltsNot Available
Brand namesNot Available
Brand mixturesNot 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
Mass Specshow(8.79 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassBenzoic Acid and Derivatives
Direct parentHydroxybenzoic Acid Derivatives
Alternative parentsAminobenzoic Acid Derivatives; Benzoic Acids; Aminophenols; Benzoyl Derivatives; Anilines; Primary Aromatic Amines; Polyols; Polyamines; Enols; Enolates; Carboxylic Acids
Substituentsaminophenol; benzoyl; phenol derivative; aniline; primary aromatic amine; polyol; polyamine; carboxylic acid derivative; enol; carboxylic acid; enolate; amine; primary amine; organonitrogen compound
Classification descriptionThis compound belongs to the hydroxybenzoic acid derivatives. These are compounds containing an hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxylic acid.
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
Property Value Probability
Human Intestinal Absorption + 0.8669
Blood Brain Barrier - 0.9444
Caco-2 permeable - 0.7319
P-glycoprotein substrate Non-substrate 0.7997
P-glycoprotein inhibitor I Non-inhibitor 0.9834
P-glycoprotein inhibitor II Non-inhibitor 0.9926
Renal organic cation transporter Non-inhibitor 0.9565
CYP450 2C9 substrate Non-substrate 0.7909
CYP450 2D6 substrate Non-substrate 0.8414
CYP450 3A4 substrate Non-substrate 0.7764
CYP450 1A2 substrate Non-inhibitor 0.7645
CYP450 2C9 substrate Non-inhibitor 0.8114
CYP450 2D6 substrate Non-inhibitor 0.9735
CYP450 2C19 substrate Non-inhibitor 0.6213
CYP450 3A4 substrate Non-inhibitor 0.845
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9262
Ames test Non AMES toxic 0.9133
Carcinogenicity Non-carcinogens 0.8719
Biodegradation Ready biodegradable 0.6606
Rat acute toxicity 1.5446 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.964
hERG inhibition (predictor II) Non-inhibitor 0.9446
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 Solubility10.5ALOGPS
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraGC-MSMS/MS1D NMR2D NMR
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC00632
PubChem Compound86
PubChem Substance46506219
ChEBI15793
ChEMBL
HET3HA
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSshow(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

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:22