Identification
- Generic Name
- 4-hydroxybenzoic acid
- DrugBank Accession Number
- DB04242
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for 4-hydroxybenzoic acid (DB04242)
- Weight
- Average: 138.122
Monoisotopic: 138.031694053 - Chemical Formula
- C7H6O3
- Synonyms
- 4-carboxyphenol
- p-Hydroxybenzoic acid
- p-salicylic acid
- External IDs
- FEMA NO. 3986
- NSC-4961
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism Up-hydroxybenzoate hydroxylase Not Available Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228) UChorismate--pyruvate lyase Not Available Escherichia coli (strain K12) Up-hydroxybenzoate hydroxylase Not Available Pseudomonas fluorescens U4-hydroxybenzoyl-CoA thioesterase Not Available Arthrobacter 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Ubiquinone Biosynthesis Metabolic - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- 1-hydroxy-2-unsubstituted benzenoid / Aromatic homomonocyclic compound / Benzoic acid / Benzoyl / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Hydroxybenzoic acid / Monocarboxylic acid or derivatives / Organic oxide
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- monohydroxybenzoic acid (CHEBI:30763)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- JG8Z55Y12H
- CAS number
- 99-96-7
- 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
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
- HMDB0000500
- KEGG Compound
- C00156
- PubChem Compound
- 135
- PubChem Substance
- 46504662
- ChemSpider
- 132
- BindingDB
- 26194
- 1649527
- ChEBI
- 30763
- ChEMBL
- CHEMBL441343
- ZINC
- ZINC000000332752
- PDBe Ligand
- PHB
- Wikipedia
- 4-Hydroxybenzoic_acid
- PDB Entries
- 1bf3 / 1bgj / 1bgn / 1bkw / 1cc4 / 1cc6 / 1cj2 / 1cj3 / 1cj4 / 1d7l … show 53 more
Clinical Trials
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
Property Value Source Water Solubility 11.9 mg/mL ALOGPS logP 1.58 ALOGPS logP 1.33 Chemaxon logS -1.1 ALOGPS pKa (Strongest Acidic) 4.38 Chemaxon pKa (Strongest Basic) -6.1 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 57.53 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 35.3 m3·mol-1 Chemaxon Polarizability 12.94 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9872 Blood Brain Barrier + 0.532 Caco-2 permeable + 0.8937 P-glycoprotein substrate Non-substrate 0.7493 P-glycoprotein inhibitor I Non-inhibitor 0.989 P-glycoprotein inhibitor II Non-inhibitor 0.9927 Renal organic cation transporter Non-inhibitor 0.9078 CYP450 2C9 substrate Non-substrate 0.8115 CYP450 2D6 substrate Non-substrate 0.9377 CYP450 3A4 substrate Non-substrate 0.7652 CYP450 1A2 substrate Non-inhibitor 0.9752 CYP450 2C9 inhibitor Non-inhibitor 0.9697 CYP450 2D6 inhibitor Non-inhibitor 0.9827 CYP450 2C19 inhibitor Non-inhibitor 0.9651 CYP450 3A4 inhibitor Non-inhibitor 0.9493 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9554 Ames test Non AMES toxic 0.9826 Carcinogenicity Non-carcinogens 0.8226 Biodegradation Ready biodegradable 0.8413 Rat acute toxicity 1.3983 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9617 hERG inhibition (predictor II) Non-inhibitor 0.9771
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 127.3669905 predictedDarkChem Lite v0.1.0 [M-H]- 127.3433905 predictedDarkChem Lite v0.1.0 [M-H]- 127.3731905 predictedDarkChem Lite v0.1.0 [M-H]- 127.2999905 predictedDarkChem Lite v0.1.0 [M-H]- 126.22566 predictedDeepCCS 1.0 (2019) [M+H]+ 128.8296905 predictedDarkChem Lite v0.1.0 [M+H]+ 129.9390905 predictedDarkChem Lite v0.1.0 [M+H]+ 128.1275905 predictedDarkChem Lite v0.1.0 [M+H]+ 128.2719905 predictedDarkChem Lite v0.1.0 [M+H]+ 129.65703 predictedDeepCCS 1.0 (2019) [M+Na]+ 128.1748905 predictedDarkChem Lite v0.1.0 [M+Na]+ 128.0034905 predictedDarkChem Lite v0.1.0 [M+Na]+ 127.9558905 predictedDarkChem Lite v0.1.0 [M+Na]+ 128.0708905 predictedDarkChem Lite v0.1.0 [M+Na]+ 139.04073 predictedDeepCCS 1.0 (2019)
Targets
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- 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
- 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
- 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
- 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 at June 13, 2005 13:24 / Updated at June 12, 2020 16:52