3-Hydroxyanthranilic Acid

Identification

Name
3-Hydroxyanthranilic Acid
Accession Number
DB03644  (EXPT00171)
Type
Small Molecule
Groups
Experimental
Description

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

Structure
Thumb
Synonyms
  • 2-Amino-3-hydroxy-benzoic acid
  • 2-Amino-3-Hydroxybenzoic Acid
  • 3-HYDROXY-ANTHRANILATE
  • 3-Hydroxy-anthranilsaeure
  • 3-hydroxyanthranilate
  • 3-Oxyanthranilic acid
External IDs
NSC-522891
Categories
UNII
1UQB1BT4OT
CAS number
548-93-6
Weight
Average: 153.1354
Monoisotopic: 153.042593095
Chemical Formula
C7H7NO3
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UTrans-2,3-dihydro-3-hydroxyanthranilate isomeraseNot AvailablePseudomonas 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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Tryptophan MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB01476
KEGG Compound
C00632
PubChem Compound
86
PubChem Substance
46506219
ChemSpider
84
ChEBI
15793
ChEMBL
CHEMBL445304
HET
3HA
PDB Entries
1u1w / 1yfy / 4hsl
MSDS
Download (58.9 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)240 °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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 inhibitorNon-inhibitor0.8114
CYP450 2D6 inhibitorNon-inhibitor0.9735
CYP450 2C19 inhibitorNon-inhibitor0.6213
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
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Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0zfv-0945000000-e3389ab25b7133eb184d
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-0zfu-1955000000-fd51cc45bf09750e2b48
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0zfv-0945000000-e3389ab25b7133eb184d
GC-MS Spectrum - GC-MSGC-MSsplash10-0zfu-1955000000-fd51cc45bf09750e2b48
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0zfv-0934000000-11e2b38a36cb364bcaf3
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0006-0920000000-a57d310e9ca51aefd0c1
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-000i-0900000000-2313e347dd8659099393
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-001i-9400000000-4e342fdebc8145b606a1
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-001i-9000000000-ee5255b437ae762be1f9
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0zfr-0900000000-ced0a738a11057bc94e4
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0a4i-0900000000-cded3154e50c6169c670
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0a4i-0900000000-9c388fc3035f19e3f156
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0a4i-1900000000-9dbb06a7728aab173e0f
MS/MS Spectrum - , negativeLC-MS/MSsplash10-0a4i-0900000000-19cfe2cda31cf7284669
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0900000000-02ae2bd70b54df77aca5
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0900000000-56e21a4ececd5541a7d8
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-052r-0900000000-e3015612b3d263fabaa9
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a5i-3900000000-670c7d91a38e852d8e4c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-5900000000-36b3a876d06807eb22a3
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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
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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
show 17 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monohydroxybenzoic acid, aminobenzoic acid (CHEBI:15793)

Targets

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
  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:15545603]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:30