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
Version3.6
Creation Date2009-02-03 11:20:53 UTC
Update Date2017-03-02 21:31:56 UTC
HMDB IDHMDB11661
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol
Description2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol (DMQH2) is an intermediate in coenzyme Q biosynthesis. It is produced by gut microbes. In microbes, the starting compound, 4-hydroxybenzoate, undergoes a prenylation, a decarboxylation and three hydroxylations alternating with three methylation reactions, resulting in the formation of coenzyme Q. In the final step, DMQH2 is converted from 2-octaprenyl-6-methoxy-1,4-benzoquinol (DDMQH2) with the help of Methyltransferase. Coenzyme Q (ubiquinone or Q) is a redox active lipid containing a long polyprenyl tail attached to a fully substituted benzoquinone ring. The number (n) of isoprene units in the polyprenyl tail (Qn) is distinct in different organisms; humans produce Q10, Caenorhabditis elegans Q9, Escherichia coli Q8, and Saccharomyces cerevisiae Q6.
Structure
Thumb
Synonyms
ValueSource
2-Polyprenyl-3-methyl-6-methoxy-1,4-benzoquinolHMDB
5-DemethoxyubiquinolHMDB
DMQH2HMDB
Chemical FormulaC38H60O3
Average Molecular Weight564.8812
Monoisotopic Molecular Weight564.454245786
IUPAC Name3-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-5-methoxy-2-methylcyclohexa-2,5-diene-1,4-diol
Traditional Name3-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-5-methoxy-2-methylcyclohexa-2,5-diene-1,4-diol
CAS Registry NumberNot Available
SMILES
COC1=CC(O)C(C)=C(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
InChI Identifier
InChI=1S/C38H60O3/c1-28(2)15-10-16-29(3)17-11-18-30(4)19-12-20-31(5)21-13-22-32(6)23-14-24-33(7)25-26-35-34(8)36(39)27-37(41-9)38(35)40/h15,17,19,21,23,25,27,36,38-40H,10-14,16,18,20,22,24,26H2,1-9H3/b29-17+,30-19+,31-21+,32-23+,33-25+
InChI KeyVFOCBGJJNKIBIS-NSUIJKAQSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassPrenol lipids
Direct ParentSesterterpenoids
Alternative Parents
Substituents
  • Sesterterpenoid
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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 Solubility0.000558 mg/mLALOGPS
logP7.59ALOGPS
logP9.24ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)13.24ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 Å2ChemAxon
Rotatable Bond Count18ChemAxon
Refractivity185.98 m3·mol-1ChemAxon
Polarizability72.38 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
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 IDFDB028352
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-9871
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB11661
Metagene LinkHMDB11661
METLIN IDNot Available
PubChem Compound53481017
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available