NAV

2-AMINO-4-CHLORO-3-HYDROXYBENZOIC ACID

Identification

Generic Name
2-AMINO-4-CHLORO-3-HYDROXYBENZOIC ACID
DrugBank Accession Number
DB04598
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 187.58
Monoisotopic: 187.00362077
Chemical Formula
C7H6ClNO3
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
U3-hydroxyanthranilate 3,4-dioxygenaseNot AvailableRalstonia metallidurans (strain CH34 / ATCC 43123 / DSM 2839)
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
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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
Not Available
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
4-halobenzoic acids / Aminobenzoic acids / Halobenzoic acids / Benzoic acids / o-Aminophenols / Aniline and substituted anilines / Benzoyl derivatives / O-chlorophenols / 1-hydroxy-4-unsubstituted benzenoids / Chlorobenzenes
show 11 more
Substituents
1-hydroxy-4-unsubstituted benzenoid / 2-chlorophenol / 2-halophenol / 4-halobenzoic acid / 4-halobenzoic acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aminobenzoic acid / Aminobenzoic acid or derivatives
show 28 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
R67LEH4X5Q
CAS number
Not Available
InChI Key
VWEPFJPQZFIOAU-UHFFFAOYSA-N
InChI
InChI=1S/C7H6ClNO3/c8-4-2-1-3(7(11)12)5(9)6(4)10/h1-2,10H,9H2,(H,11,12)
IUPAC Name
2-amino-4-chloro-3-hydroxybenzoic acid
SMILES
NC1=C(C=CC(Cl)=C1O)C(O)=O

References

General References
Not Available
PubChem Compound
114947
PubChem Substance
46506832
ChemSpider
102886
ChEMBL
CHEMBL1230244
ZINC
ZINC000006091734
PDBe Ligand
4AA
PDB Entries
1yfw / 1yfx / 6bvq / 6bvs / 6d61

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.86 mg/mLALOGPS
logP1.62ALOGPS
logP1.75Chemaxon
logS-2ALOGPS
pKa (Strongest Acidic)4.56Chemaxon
pKa (Strongest Basic)1.53Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area83.55 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity44.8 m3·mol-1Chemaxon
Polarizability16.42 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8796
Blood Brain Barrier-0.8537
Caco-2 permeable-0.5779
P-glycoprotein substrateNon-substrate0.8098
P-glycoprotein inhibitor INon-inhibitor0.9833
P-glycoprotein inhibitor IINon-inhibitor0.9942
Renal organic cation transporterNon-inhibitor0.9533
CYP450 2C9 substrateNon-substrate0.7965
CYP450 2D6 substrateNon-substrate0.859
CYP450 3A4 substrateNon-substrate0.7137
CYP450 1A2 substrateInhibitor0.5534
CYP450 2C9 inhibitorNon-inhibitor0.7494
CYP450 2D6 inhibitorNon-inhibitor0.9374
CYP450 2C19 inhibitorNon-inhibitor0.7858
CYP450 3A4 inhibitorNon-inhibitor0.8058
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8764
Ames testNon AMES toxic0.8994
CarcinogenicityNon-carcinogens0.8088
BiodegradationNot ready biodegradable0.8951
Rat acute toxicity1.8349 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9506
hERG inhibition (predictor II)Non-inhibitor0.9375
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-000l-1900000000-96dacc113a7cfaca76ed
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0900000000-09c8657b9adc07f0e63d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0900000000-1d90451ad1e05ea9180c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00du-0900000000-d2234e3035f87b962107
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01qc-8900000000-cf90db9f57dea2674f02
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-4900000000-e43a1c5355a7b7ac711d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9000000000-db058eb2b79d99b5228f
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-129.12575
predicted
DeepCCS 1.0 (2019)
[M+H]+132.95308
predicted
DeepCCS 1.0 (2019)
[M+Na]+142.26773
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 3-hydroxyanthranilate 3,4-dioxygenase
Kind
Protein
Organism
Ralstonia metallidurans (strain CH34 / ATCC 43123 / DSM 2839)
Pharmacological action
Unknown
General Function
Iron ion binding
Specific Function
Catalyzes the oxidative ring opening of 3-hydroxyanthranilate to 2-amino-3-carboxymuconate semialdehyde, which spontaneously cyclizes to quinolinate.
Gene Name
nbaC
Uniprot ID
Q1LCS4
Uniprot Name
3-hydroxyanthranilate 3,4-dioxygenase
Molecular Weight
20027.475 Da

Drug created at September 11, 2007 17:48 / Updated at June 12, 2020 16:52