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Identification
NameP-Hydroxybenzoic Acid
Accession NumberDB04242  (EXPT02580)
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 numberNot Available
WeightAverage: 138.1207
Monoisotopic: 138.031694058
Chemical FormulaC7H6O3
InChI KeyFJKROLUGYXJWQN-UHFFFAOYSA-N
InChI
InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10)
IUPAC Name
4-hydroxybenzoic acid
SMILES
OC(=O)C1=CC=C(O)C=C1
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
  • Hydroxybenzoic acid
  • Benzoic acid
  • Benzoyl
  • Phenol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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
Pathways
PathwayCategorySMPDB ID
Ubiquinone BiosynthesisMetabolicSMP00065
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9872
Blood Brain Barrier+0.532
Caco-2 permeable+0.8937
P-glycoprotein substrateNon-substrate0.7493
P-glycoprotein inhibitor INon-inhibitor0.989
P-glycoprotein inhibitor IINon-inhibitor0.9927
Renal organic cation transporterNon-inhibitor0.9078
CYP450 2C9 substrateNon-substrate0.8115
CYP450 2D6 substrateNon-substrate0.9377
CYP450 3A4 substrateNon-substrate0.7652
CYP450 1A2 substrateNon-inhibitor0.9752
CYP450 2C9 substrateNon-inhibitor0.9697
CYP450 2D6 substrateNon-inhibitor0.9827
CYP450 2C19 substrateNon-inhibitor0.9651
CYP450 3A4 substrateNon-inhibitor0.9493
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9554
Ames testNon AMES toxic0.9826
CarcinogenicityNon-carcinogens0.8226
BiodegradationReady biodegradable0.8413
Rat acute toxicity1.3983 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9617
hERG inhibition (predictor II)Non-inhibitor0.9771
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility11.9 mg/mLALOGPS
logP1.58ALOGPS
logP1.33ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)4.38ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.3 m3·mol-1ChemAxon
Polarizability12.94 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraGC-MSMS/MSLC-MSMS1D NMR2D NMR
References
Synthesis Reference

Kristi A. Fjare, “Process for preparation of p-hydroxybenzoic acid from p-methoxytoluene.” U.S. Patent US4740614, issued August, 1960.

US4740614
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. Chorismate--pyruvate lyase

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Chorismate--pyruvate lyase P26602 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

3. 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

4. 4-hydroxybenzoyl-CoA thioesterase

Kind: protein

Organism: Arthrobacter sp.

Pharmacological action: unknown

Components

Name UniProt ID Details
4-hydroxybenzoyl-CoA thioesterase Q04416 Details
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:23