Showing metabocard for 4-Hydroxybenzoic acid (BMDB0000500)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:31:42 UTC
Update Date2020-05-21 16:28:36 UTC
BMDB IDBMDB0000500
Secondary Accession Numbers
  • BMDB00500
Metabolite Identification
Common Name4-Hydroxybenzoic acid
Description4-Hydroxybenzoic acid, also known as p-hydroxybenzoate or 4-carboxyphenol, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 4-Hydroxybenzoic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. 4-Hydroxybenzoic acid exists in all living species, ranging from bacteria to humans. In cattle, 4-hydroxybenzoic acid is involved in the metabolic pathway called ubiquinone biosynthesis pathway.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
4-CarboxyphenolChEBI
p-HYDROXYBENZOIC ACIDChEBI
p-Salicylic acidChEBI
Hydroxybenzoic acidKegg
Hydroxybenzenecarboxylic acidKegg
p-HYDROXYBENZOateGenerator
p-SalicylateGenerator
HydroxybenzoateGenerator
HydroxybenzenecarboxylateGenerator
4-HydroxybenzoateGenerator
4-Hydroxy-benzoateHMDB
4-Hydroxy-benzoesaeureHMDB
4-Hydroxy-benzoic acidHMDB
p-CarboxyphenolHMDB
p-Hydroxy-benzoateHMDB
p-Hydroxy-benzoic acidHMDB
Paraben-acidHMDB
4-Hydroxybenzoic acid, calcium saltHMDB
4-Hydroxybenzoic acid, dilithium saltHMDB
4-Hydroxybenzoic acid, disodium saltHMDB
Para-hydroxybenzoic acidHMDB
Sodium p-hydroxybenzoate tetrahydrateHMDB
4-Hydroxybenzoic acid, copper(2+)(1:1) saltHMDB
4-Hydroxybenzoic acid, dipotassium saltHMDB
4-Hydroxybenzoic acid, monopotassium saltHMDB
4-Hydroxybenzoic acid, monosodium saltHMDB
4-Hydroxybenzoic acid, monosodium salt, 11C-labeledHMDB
4-Hydroxybenzene carboxylic acidHMDB
p-Hydroxyl benzoic acidHMDB
4-Hydroxybenzoic acidHMDB
Chemical FormulaC7H6O3
Average Molecular Weight138.122
Monoisotopic Molecular Weight138.031694053
IUPAC Name4-hydroxybenzoic acid
Traditional NameP-hydroxybenzoic acid
CAS Registry Number99-96-7
SMILES
OC(=O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10)
InChI KeyFJKROLUGYXJWQN-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives 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
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.0 mg/mLNot Available
LogP1.58HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.3 m³·mol⁻¹ChemAxon
Polarizability12.94 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Mammary Gland
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000500
DrugBank IDDB04242
Phenol Explorer Compound ID418
FooDB IDFDB010508
KNApSAcK IDC00000856
Chemspider ID132
KEGG Compound IDC00156
BioCyc ID4-hydroxybenzoate
BiGG ID34069
Wikipedia Link4-Hydroxybenzoic_acid
METLIN ID5486
PubChem Compound135
PDB IDNot Available
ChEBI ID30763
References
Synthesis ReferenceIvanov, G. E.; Slavcheva, L. Preparation, properties, and applications of p-hydroxy-benzoic acid. Khimiya i Industriya (1922-1988) (1966), 38(10), 458-63.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  2. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]

Enzymes

Enzyme Details
1. 4-hydroxybenzoate polyprenyltransferase, mitochondrial
General function:
Not Available
Specific function:
Catalyzes the prenylation of para-hydroxybenzoate (PHB) with an all-trans polyprenyl group. Mediates the second step in the final reaction sequence of coenzyme Q (CoQ) biosynthesis, which is the condensation of the polyisoprenoid side chain with PHB, generating the first membrane-bound Q intermediate.
Gene Name:
COQ2
Uniprot ID:
Q2KIQ4
Molecular weight:
40628.0
Reactions
4-Hydroxybenzoic acid + All-trans-hexaprenyl diphosphate → 3-hexaprenyl-4-hydroxybenzoic acid + Pyrophosphatedetails