2,4-Dihydroxybenzoic Acid

Identification

Name
2,4-Dihydroxybenzoic Acid
Accession Number
DB02839  (EXPT01241)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
FEMA NO. 3798 / NSC-13564 / NSC-4740
Categories
UNII
LU39SC9JYL
CAS number
89-86-1
Weight
Average: 154.1201
Monoisotopic: 154.02660868
Chemical Formula
C7H6O4
InChI Key
UIAFKZKHHVMJGS-UHFFFAOYSA-N
InChI
InChI=1S/C7H6O4/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,8-9H,(H,10,11)
IUPAC Name
2,4-dihydroxybenzoic acid
SMILES
OC(=O)C1=CC=C(O)C=C1O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
Up-hydroxybenzoate hydroxylaseNot AvailablePseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Up-hydroxybenzoate hydroxylaseNot 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
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Peter Neumann, Ulrich Eichenauer, "Preparation of 2,4-dihydroxybenzoic acid." U.S. Patent US4996354, issued August, 1955.

US4996354
General References
Not Available
External Links
Human Metabolome Database
HMDB29666
PubChem Compound
1491
PubChem Substance
46506634
ChemSpider
1446
BindingDB
74208
ChEMBL
CHEMBL328910
HET
DOB
PDB Entries
1dod / 1doe / 1pbb

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)226 dec °CPhysProp
water solubility5780 mg/L (at 25 °C)BEILSTEIN
logP1.63HANSCH,C ET AL. (1995)
pKa3.11 (at 25 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility12.4 mg/mLALOGPS
logP1.23ALOGPS
logP1.67ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.1ChemAxon
pKa (Strongest Basic)-5.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.28 m3·mol-1ChemAxon
Polarizability13.8 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9223
Blood Brain Barrier+0.666
Caco-2 permeable+0.7694
P-glycoprotein substrateNon-substrate0.7212
P-glycoprotein inhibitor INon-inhibitor0.9848
P-glycoprotein inhibitor IINon-inhibitor0.9937
Renal organic cation transporterNon-inhibitor0.9221
CYP450 2C9 substrateNon-substrate0.7994
CYP450 2D6 substrateNon-substrate0.9202
CYP450 3A4 substrateNon-substrate0.7442
CYP450 1A2 substrateNon-inhibitor0.9258
CYP450 2C9 inhibitorNon-inhibitor0.7325
CYP450 2D6 inhibitorNon-inhibitor0.9698
CYP450 2C19 inhibitorNon-inhibitor0.7879
CYP450 3A4 inhibitorNon-inhibitor0.7558
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8568
Ames testNon AMES toxic0.9896
CarcinogenicityNon-carcinogens0.8818
BiodegradationReady biodegradable0.8945
Rat acute toxicity2.1788 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9648
hERG inhibition (predictor II)Non-inhibitor0.9776
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-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0f79-5900000000-f66892920391d049309d
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

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
Salicylic acids / Benzoic acids / Resorcinols / Benzoyl derivatives / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organooxygen compounds
show 2 more
Substituents
Dihydroxybenzoic acid / Hydroxybenzoic acid / Salicylic acid / Salicylic acid or derivatives / Benzoic acid / Benzoyl / Resorcinol / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Phenol
show 9 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pharmacological action
Unknown
General Function
Monooxygenase activity
Specific Function
Not Available
Gene Name
pobA
Uniprot ID
P20586
Uniprot Name
p-hydroxybenzoate hydroxylase
Molecular Weight
44323.175 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Pseudomonas fluorescens
Pharmacological action
Unknown
General Function
Fad binding
Specific Function
Not Available
Gene Name
pobA
Uniprot ID
P00438
Uniprot Name
p-hydroxybenzoate hydroxylase
Molecular Weight
44321.205 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:19