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Identification
NameP-Hydroxybenzoic Acid
Accession NumberDB04242  (EXPT02580)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not 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 KeyInChIKey=FJKROLUGYXJWQN-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
PathwaysNot Available
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 inhibitorNon-inhibitor0.9697
CYP450 2D6 inhibitorNon-inhibitor0.9827
CYP450 2C19 inhibitorNon-inhibitor0.9651
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-3fz0000000-89473836b0071542185eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-8xz0000000-dd5367ba838ccd5b29d8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-zji0000000-11db590137f79b7a32bfView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-cvz0000000-7e553522b6ec5c075e25View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-zj00000000-9fb9f8fbd7cf90a88604View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-z100000000-f5d09d09184f72ec3bd7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-z100000000-d31cea608d0764edf5d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positivesplash10-kz00000000-9b1d88421f1e1ded16f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positivesplash10-zr00000000-3ac766249fee4c68b8f4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-oz00000000-4e15a4102e0b3bc8ddceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-zv00000000-9e7208bfb79f9cca336bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-z100000000-1ed6d8123d44d126ed64View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-z000000000-63a0e9c65e315bb89281View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-z000000000-a8befcaa45eced4a9a51View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-z000000000-26788d399f2b459abc21View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-oz00000000-ba06f5c422d59cd10ceaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-z700000000-193fd4eb0cf324fb3abcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-z800000000-c834f7be13341f3e19b8View in MoNA
MSMass Spectrum (Electron Ionization)splash10-qz00000000-71548845dbf99346758dView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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 ReferencesNot 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