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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:38 UTC
HMDB IDHMDB00977
Secondary Accession NumbersNone
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 KeyInChIKey=YSZSVGFMAJXGMQ-FRICUITQSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 2-polyprenyl-6-methoxyphenols. These are compounds containing a polyisoprene chain attached at the 2-position of a 6-methoxyphenol group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenylphenols
Direct Parent2-polyprenyl-6-methoxyphenols
Alternative Parents
Substituents
  • 2-polyprenyl-6-methoxyphenol
  • Sesterterpenoid
  • M-methoxybenzoic acid or derivatives
  • Methoxyphenol
  • Hydroxybenzoic acid
  • Benzoic acid
  • Benzoic acid or derivatives
  • Methoxybenzene
  • Phenol ether
  • Benzoyl
  • Anisole
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Component of Ubiquinone biosynthesis
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
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 Solubility0.000365 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count19ChemAxon
Refractivity185.01 m3·mol-1ChemAxon
Polarizability72.35 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Ubiquinone BiosynthesisSMP00065map00130
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
NuGOwiki LinkHMDB00977
Metagene LinkHMDB00977
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