You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 08:01:57 UTC
HMDB IDHMDB0001063
Secondary Accession Numbers
  • HMDB01063
Metabolite Identification
Common Name3-Hexaprenyl-4,5-Dihydroxybenzoic acid
Description3-Hexaprenyl-4,5-Dihydroxybenzoic acid is an intermediate in the biosynthesis of Ubiquinone. It is a substrate for Hexaprenyldihydroxybenzoate methyltransferase (mitochondrial).
Structure
Thumb
Synonyms
ValueSource
3-Hexaprenyl-4,5-dihydroxybenzoateChEBI
3,4-Dihydroxy-5-hexaprenylbenzoateHMDB
3,4-Dihydroxy-5-hexaprenylbenzoic acidHMDB
DhhpbaHMDB
Chemical FormulaC37H54O4
Average Molecular Weight562.8223
Monoisotopic Molecular Weight562.402210216
IUPAC Name3-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-4,5-dihydroxybenzoic acid
Traditional Namedhhpba
CAS Registry Number63975-40-6
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=C(O)C(O)=CC(=C1)C(O)=O
InChI Identifier
InChI=1S/C37H54O4/c1-27(2)13-8-14-28(3)15-9-16-29(4)17-10-18-30(5)19-11-20-31(6)21-12-22-32(7)23-24-33-25-34(37(40)41)26-35(38)36(33)39/h13,15,17,19,21,23,25-26,38-39H,8-12,14,16,18,20,22,24H2,1-7H3,(H,40,41)/b28-15+,29-17+,30-19+,31-21+,32-23+
InChI KeyVEPICJBQCOUQPI-IRVXXIIISA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as polyprenylbenzene-1,2-diols. These are compounds containing a polyisoprene chain attached to a catechol group.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassPrenol lipids
Direct ParentPolyprenylbenzene-1,2-diols
Alternative Parents
Substituents
  • Polyprenylbenzene-1,2-diol
  • Sesterterpenoid
  • Dihydroxybenzoic acid
  • Hydroxybenzoic acid
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzoyl
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Chemical reaction:

    Biochemical 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 Solubility0.00057 g/LALOGPS
logP8.41ALOGPS
logP11.05ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)4.13ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity180.53 m³·mol⁻¹ChemAxon
Polarizability70.25 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xs-0212090000-04095cbd227edc49a7a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0849150000-639873a7488c1a696007View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00tb-1769200000-4cbbd0cfab58c6dd3764View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000090000-a08e91d9fefaf0f162ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02t9-0000090000-99d552c5bbb95acff7ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfs-1702690000-7f58130fe1eabd49d71cView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Ubiquinone BiosynthesisPw000039Pw000039 greyscalePw000039 simpleMap00130
Displaying 1 entry
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022402
KNApSAcK IDNot Available
Chemspider ID4444330
KEGG Compound IDC05200
BioCyc ID3-HEXAPRENYL-45-DIHYDROXYBENZOATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5976
PubChem Compound5280760
PDB IDNot Available
ChEBI ID18081
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in methyltransferase activity
Specific function:
Not Available
Gene Name:
COQ3
Uniprot ID:
Q9NZJ6
Molecular weight:
41053.76
Reactions
S-Adenosylmethionine + 3-Hexaprenyl-4,5-Dihydroxybenzoic acid → S-Adenosylhomocysteine + 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid + Hydrogen Iondetails