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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-08-12 14:21:20 UTC
Update Date2020-02-26 21:26:47 UTC
HMDB IDHMDB0006816
Secondary Accession Numbers
  • HMDB06816
Metabolite Identification
Common Name3-Hexaprenyl-4-hydroxybenzoic acid
Description3-hexaprenyl-4-hydroxybenzoate is an intermediate in ubiquinone biosynthesis and is produced from 4-hydroxybenzoate by the enzyme 4-hydroxybenzoate hexaprenyltransferase.
Structure
Data?1582752407
Synonyms
ValueSource
(all-e)-3-(3,7,11,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaenyl)-4-hydroxybenzoic acidChEBI
all-trans-3-(3,7,11,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaenyl)-4-hydroxybenzoic acidChEBI
(all-e)-3-(3,7,11,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaenyl)-4-hydroxybenzoateGenerator
all-trans-3-(3,7,11,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaenyl)-4-hydroxybenzoateGenerator
3-Hexaprenyl-4-hydroxybenzoateGenerator
3-(3,7,11,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaenyl)-4-hydroxy-benzoateHMDB
3-(3,7,11,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaenyl)-4-hydroxy-benzoic acidHMDB
Chemical FormulaC37H54O3
Average Molecular Weight546.8229
Monoisotopic Molecular Weight546.407295594
IUPAC Name3-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-4-hydroxybenzoic acid
Traditional Name3-hexaprenyl-4-hydroxybenzoate
CAS Registry Number65848-03-5
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=CC(=CC=C1O)C(O)=O
InChI Identifier
InChI=1S/C37H54O3/c1-28(2)13-8-14-29(3)15-9-16-30(4)17-10-18-31(5)19-11-20-32(6)21-12-22-33(7)23-24-34-27-35(37(39)40)25-26-36(34)38/h13,15,17,19,21,23,25-27,38H,8-12,14,16,18,20,22,24H2,1-7H3,(H,39,40)/b29-15+,30-17+,31-19+,32-21+,33-23+
InChI KeyLKMQQQABIGIHGL-LAAQXVIISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as polyprenylphenols. Polyprenylphenols are compounds containing a polyisoprene chain attached to a phenol group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenylphenols
Direct ParentPolyprenylphenols
Alternative Parents
Substituents
  • Polyprenylphenol
  • Sesterterpenoid
  • Hydroxybenzoic acid
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00036 g/LALOGPS
logP8.74ALOGPS
logP11.35ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)4.35ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity178.55 m³·mol⁻¹ChemAxon
Polarizability68.67 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05ai-3496450000-5b468805ae29a5f59a42Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-3222219000-0638b89fa0bde34d7abbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f92-0111090000-0efba026d858a4ae0c57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ufs-0749360000-6112d4d11f00cf6a1fbdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-2579200000-1a695b7874053d38599aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000090000-451426c2227e9a66c0aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-0000190000-4173c10b0b5d3133deabSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-2112920000-b9b9e484d8dc60509991Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030426
KNApSAcK IDNot Available
Chemspider ID10128306
KEGG Compound IDC13425
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11954011
PDB IDNot Available
ChEBI ID31116
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in prenyltransferase activity
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.
Gene Name:
COQ2
Uniprot ID:
Q96H96
Molecular weight:
45593.67
Reactions
all-trans-Hexaprenyl diphosphate + 4-Hydroxybenzoic acid → 3-Hexaprenyl-4-hydroxybenzoic acid + Pyrophosphatedetails