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Identification
Name2,4-Dihydroxybenzoic Acid
Accession NumberDB02839  (EXPT01241)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number89-86-1
WeightAverage: 154.1201
Monoisotopic: 154.02660868
Chemical FormulaC7H6O4
InChI KeyUIAFKZKHHVMJGS-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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHydroxybenzoic acid derivatives
Alternative Parents
Substituents
  • Dihydroxybenzoic acid
  • Salicylic acid
  • Salicylic acid or derivatives
  • Hydroxybenzoic acid
  • Benzoic acid
  • Resorcinol
  • Benzoyl
  • Phenol
  • Vinylogous acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.7325
CYP450 2D6 substrateNon-inhibitor0.9698
CYP450 2C19 substrateNon-inhibitor0.7879
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point226 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

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

US4996354
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. p-hydroxybenzoate hydroxylase

Kind: protein

Organism: Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)

Pharmacological action: unknown

Components

Name UniProt ID Details
p-hydroxybenzoate hydroxylase P20586 Details

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
  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

2. p-hydroxybenzoate hydroxylase

Kind: protein

Organism: Pseudomonas fluorescens

Pharmacological action: unknown

Components

Name UniProt ID Details
p-hydroxybenzoate hydroxylase P00438 Details

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
  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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:19