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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 19:03:46 UTC
HMDB IDHMDB0000977
Secondary Accession Numbers
  • HMDB00977
Metabolite Identification
Common Name3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid
Description3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid is an intermediate in the biosynthesis of Ubiquinone. It is a substrate for Hexaprenyldihydroxybenzoate methyltransferase (mitochondrial).
Structure
Thumb
Synonyms
ValueSource
3-Hexaprenyl-4-hydroxy-5-methoxybenzoateChEBI
3-Methoxy-4-hydroxy-5-hexaprenylbenzoateHMDB
3-Methoxy-4-hydroxy-5-hexaprenylbenzoic acidHMDB
3-MHHBHMDB
Hexaprenyl-4-hydroxy-5-methoxybenzoateHMDB
Hexaprenyl-4-hydroxy-5-methoxybenzoic acidHMDB
Chemical FormulaC38H56O4
Average Molecular Weight576.8488
Monoisotopic Molecular Weight576.41786028
IUPAC Name3-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-4-hydroxy-5-methoxybenzoic acid
Traditional Name3-mhhb
CAS Registry Number66551-60-8
SMILES
COC1=CC(=CC(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C1O)C(O)=O
InChI Identifier
InChI=1S/C38H56O4/c1-28(2)14-9-15-29(3)16-10-17-30(4)18-11-19-31(5)20-12-21-32(6)22-13-23-33(7)24-25-34-26-35(38(40)41)27-36(42-8)37(34)39/h14,16,18,20,22,24,26-27,39H,9-13,15,17,19,21,23,25H2,1-8H3,(H,40,41)/b29-16+,30-18+,31-20+,32-22+,33-24+
InChI KeyYSZSVGFMAJXGMQ-FRICUITQSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as 2-polyprenyl-6-methoxyphenols. These are compounds containing a polyisoprene chain attached at the 2-position of a 6-methoxyphenol group.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassPrenol lipids
Direct Parent2-polyprenyl-6-methoxyphenols
Alternative Parents
Substituents
  • 2-polyprenyl-6-methoxyphenol
  • Sesterterpenoid
  • M-methoxybenzoic acid or derivatives
  • Hydroxybenzoic acid
  • Methoxyphenol
  • Benzoic acid or derivatives
  • Benzoic acid
  • Methoxybenzene
  • Benzoyl
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • 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 Solubility0.00036 g/LALOGPS
logP8.61ALOGPS
logP11.2ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)4.12ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity185.01 m³·mol⁻¹ChemAxon
Polarizability72.35 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, Positivesplash10-08g0-2388590000-89e434c77e88e9089ef4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-003r-3147469000-0708567822e5bfd90a9eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0059-0212090000-055eaf6bf9bb7f66403fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003s-0739160000-67aa4818a2ec38ef35ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gxt-1359210000-0d48ce3c1daca56ef467View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000090000-a22409cb6dbbb1a464f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00o0-0000090000-dda0834068a4ec0b05d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01b9-2200290000-211ab1bf8b89830eeb7eView 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 IDFDB022347
KNApSAcK IDNot Available
Chemspider ID4444339
KEGG Compound IDC05313
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5915
PubChem Compound5280776
PDB IDNot Available
ChEBI ID16835
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