P-Hydroxybenzoic Acid

Identification

Name
P-Hydroxybenzoic Acid
Accession Number
DB04242  (EXPT02580)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
FEMA NO. 3986 / NSC-4961
Categories
Not Available
UNII
JG8Z55Y12H
CAS number
Not Available
Weight
Average: 138.1207
Monoisotopic: 138.031694058
Chemical Formula
C7H6O3
InChI Key
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

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)
UChorismate--pyruvate lyaseNot AvailableEscherichia coli (strain K12)
Up-hydroxybenzoate hydroxylaseNot AvailablePseudomonas fluorescens
U4-hydroxybenzoyl-CoA thioesteraseNot AvailableArthrobacter sp.
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
PathwayCategory
Ubiquinone BiosynthesisMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB00500
KEGG Compound
C00156
PubChem Compound
135
PubChem Substance
46504662
ChemSpider
132
BindingDB
26194
ChEBI
30763
ChEMBL
CHEMBL441343
HET
PHB
PDB Entries
1bf3 / 1bgj / 1bgn / 1bkw / 1cc4 / 1cc6 / 1cj2 / 1cj3 / 1cj4 / 1d7l
show 42 more

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
Not 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-01b9-0490000000-89473836b0071542185e
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-00xu-2890000000-dd5367ba838ccd5b29d8
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-00di-9540000000-11db590137f79b7a32bf
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-00xu-3890000000-7e553522b6ec5c075e25
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-00dr-5900000000-9b1d88421f1e1ded16f9
GC-MS Spectrum - EI-BGC-MSsplash10-00di-9700000000-a9bb4b71d8b23a56ca67
GC-MS Spectrum - EI-BGC-MSsplash10-0079-6900000000-617d58eb059c1e918ca0
GC-MS Spectrum - EI-BGC-MSsplash10-00dr-4900000000-97bfa38b0d6bc152d470
GC-MS Spectrum - EI-BGC-MSsplash10-00dr-7900000000-290af590b1fc44a86969
GC-MS Spectrum - EI-BGC-MSsplash10-01b9-0490000000-d6001fb50397705d3e0b
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-01b9-0490000000-89473836b0071542185e
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00xu-2890000000-dd5367ba838ccd5b29d8
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9540000000-11db590137f79b7a32bf
GC-MS Spectrum - GC-MSGC-MSsplash10-00xu-3890000000-7e553522b6ec5c075e25
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00xu-2980000000-0ba0ea7d63bd7fff3b22
Mass Spectrum (Electron Ionization)MSsplash10-00dr-6900000000-71548845dbf99346758d
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-000f-9400000000-9fb9f8fbd7cf90a88604
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-0006-9000000000-f5d09d09184f72ec3bd7
MS/MS Spectrum - Quattro_QQQ 40V, NegativeLC-MS/MSsplash10-0006-9000000000-d31cea608d0764edf5d0
MS/MS Spectrum - EI-B (HITACHI M-68) , PositiveLC-MS/MSsplash10-00dr-5900000000-9b1d88421f1e1ded16f9
MS/MS Spectrum - EI-B (HITACHI M-60) , PositiveLC-MS/MSsplash10-00di-9700000000-3ac766249fee4c68b8f4
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-0079-6900000000-4e15a4102e0b3bc8ddce
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-0a4r-9800000000-9e7208bfb79f9cca336b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0a4i-9000000000-1ed6d8123d44d126ed64
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0a4i-9000000000-63a0e9c65e315bb89281
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0a4i-9000000000-a8befcaa45eced4a9a51
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0a4i-9000000000-26788d399f2b459abc21
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0072-6900000000-ba06f5c422d59cd10cea
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0002-9100000000-193fd4eb0cf324fb3abc
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0006-9200000000-c834f7be13341f3e19b8
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
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4r-9800000000-9e7208bfb79f9cca336b
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9000000000-1ed6d8123d44d126ed64
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9000000000-e80d9637393e63e2d07c
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9000000000-a8befcaa45eced4a9a51
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9000000000-26788d399f2b459abc21
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000l-6900000000-998dd6da8c3df5deae6d
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0006-9200000000-c834f7be13341f3e19b8
MS/MS Spectrum - , negativeLC-MS/MSsplash10-0006-9100000000-bcc25280789b143ca114
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0072-6900000000-ba06f5c422d59cd10cea
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-9100000000-193fd4eb0cf324fb3abc
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

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
Benzoic acids / Benzoyl derivatives / 1-hydroxy-2-unsubstituted benzenoids / Monocarboxylic acids and derivatives / Carboxylic acids / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Hydroxybenzoic acid / Benzoic acid / Benzoyl / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Monocarboxylic acid or derivatives / Carboxylic acid / Carboxylic acid derivative / Organic oxygen compound / Organic oxide
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monohydroxybenzoic acid (CHEBI:30763)

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
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Chorismate lyase activity
Specific Function
Removes the pyruvyl group from chorismate, with concomitant aromatization of the ring, to provide 4-hydroxybenzoate (4HB) for the ubiquinone pathway.
Gene Name
ubiC
Uniprot ID
P26602
Uniprot Name
Chorismate pyruvate-lyase
Molecular Weight
18776.68 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]
Kind
Protein
Organism
Arthrobacter sp.
Pharmacological action
Unknown
General Function
4-hydroxybenzoyl-coa thioesterase activity
Specific Function
Not Available
Gene Name
fcbC
Uniprot ID
Q04416
Uniprot Name
4-hydroxybenzoyl-CoA thioesterase
Molecular Weight
16394.32 Da

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:39