Identification
- Generic Name
- 3-hydroxyanthranilic acid
- DrugBank Accession Number
- DB03644
- Background
An oxidation product of tryptophan metabolism. It may be a free radical scavenger and a carcinogen.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for 3-hydroxyanthranilic acid (DB03644)
- Weight
- Average: 153.1354
Monoisotopic: 153.042593095 - Chemical Formula
- C7H7NO3
- Synonyms
- 2-Amino-3-hydroxy-benzoic acid
- 2-Amino-3-Hydroxybenzoic Acid
- 3-Oxyanthranilic acid
- External IDs
- NSC-522891
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UTrans-2,3-dihydro-3-hydroxyanthranilate isomerase Not Available Pseudomonas fluorescens - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Tryptophan Metabolism Metabolic - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzoic acids and derivatives
- Direct Parent
- Hydroxybenzoic acid derivatives
- Alternative Parents
- Aminobenzoic acids / Benzoic acids / o-Aminophenols / Aniline and substituted anilines / Benzoyl derivatives / 1-hydroxy-2-unsubstituted benzenoids / 1-hydroxy-4-unsubstituted benzenoids / Vinylogous amides / Amino acids / Monocarboxylic acids and derivatives show 6 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Amine / Amino acid / Amino acid or derivatives / Aminobenzoic acid / Aminobenzoic acid or derivatives / Aminophenol / Aniline or substituted anilines / Aromatic homomonocyclic compound show 17 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- monohydroxybenzoic acid, aminobenzoic acid (CHEBI:15793)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 1UQB1BT4OT
- CAS number
- 548-93-6
- InChI Key
- WJXSWCUQABXPFS-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
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0001476
- KEGG Compound
- C00632
- PubChem Compound
- 86
- PubChem Substance
- 46506219
- ChemSpider
- 84
- ChEBI
- 15793
- ChEMBL
- CHEMBL445304
- ZINC
- ZINC000000388292
- PDBe Ligand
- 3HA
- Wikipedia
- 3-Hydroxyanthranilic_acid
- PDB Entries
- 1u1w / 1yfy / 4hsl / 6cd3 / 6d62 / 6siy / 6siz / 6sj2 / 6vi6 / 6vi7 … show 2 more
- MSDS
- Download (58.9 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 240 °C Not Available - Predicted Properties
Property Value Source Water Solubility 10.5 mg/mL ALOGPS logP 0.81 ALOGPS logP 1.15 Chemaxon logS -1.2 ALOGPS pKa (Strongest Acidic) 1.94 Chemaxon pKa (Strongest Basic) 4.82 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 83.55 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 40 m3·mol-1 Chemaxon Polarizability 14.18 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - 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 inhibitor Non-inhibitor 0.8114 CYP450 2D6 inhibitor Non-inhibitor 0.9735 CYP450 2C19 inhibitor Non-inhibitor 0.6213 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Download (8.79 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 130.5197263 predictedDarkChem Lite v0.1.0 [M-H]- 130.4530263 predictedDarkChem Lite v0.1.0 [M-H]- 130.7514263 predictedDarkChem Lite v0.1.0 [M-H]- 127.20071 predictedDeepCCS 1.0 (2019) [M+H]+ 131.9044263 predictedDarkChem Lite v0.1.0 [M+H]+ 131.8699263 predictedDarkChem Lite v0.1.0 [M+H]+ 132.1433263 predictedDarkChem Lite v0.1.0 [M+H]+ 131.02875 predictedDeepCCS 1.0 (2019) [M+Na]+ 130.9810263 predictedDarkChem Lite v0.1.0 [M+Na]+ 131.2947263 predictedDarkChem Lite v0.1.0 [M+Na]+ 131.1744263 predictedDarkChem Lite v0.1.0 [M+Na]+ 139.72133 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Pseudomonas fluorescens
- Pharmacological action
- Unknown
- General Function
- Isomerase activity
- Specific Function
- Isomerase that catalyzes the condensation of two molecules of trans-2,3-dihydro-3-hydroxyanthranilic acid (DHHA) into the phenazine ring system. The final product is not yet known.
- Gene Name
- phzF
- Uniprot ID
- Q51792
- Uniprot Name
- Trans-2,3-dihydro-3-hydroxyanthranilate isomerase
- Molecular Weight
- 30052.965 Da
References
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52