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Record Information
Version3.6
Creation Date2008-08-12 14:36:36 UTC
Update Date2016-02-11 01:07:58 UTC
HMDB IDHMDB06820
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone
Description2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone is involved in the ubiquinone biosynthesis pathway. 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone is created from 2-Hexaprenyl-3-methyl-6-methoxy-1,4-benzoquinone by ubiquinone biosynthesis monooxygenase Coq7 [EC:1.14.13.-]. 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone is then converted to ubiquinone by hexaprenyldihydroxybenzoate methyltransferase [EC:2.1.1.114].
Structure
Thumb
SynonymsNot Available
Chemical FormulaC38H56O4
Average Molecular Weight576.8488
Monoisotopic Molecular Weight576.41786028
IUPAC Name4-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-5-hydroxy-6-methoxy-3-methylcyclohexa-3,5-diene-1,2-dione
Traditional Name4-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-5-hydroxy-6-methoxy-3-methylcyclohexa-3,5-diene-1,2-dione
CAS Registry NumberNot Available
SMILES
COC1=C(O)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)=C(C)C(=O)C1=O
InChI Identifier
InChI=1S/C38H56O4/c1-27(2)15-10-16-28(3)17-11-18-29(4)19-12-20-30(5)21-13-22-31(6)23-14-24-32(7)25-26-34-33(8)35(39)37(41)38(42-9)36(34)40/h15,17,19,21,23,25,40H,10-14,16,18,20,22,24,26H2,1-9H3/b28-17+,29-19+,30-21+,31-23+,32-25+
InChI KeyInChIKey=IALHZQNPELKEGE-HGJBZHBGSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesterterpenoids
Direct ParentSesterterpenoids
Alternative Parents
Substituents
  • Sesterterpenoid
  • Quinone
  • O-benzoquinone
  • Vinylogous acid
  • Cyclic ketone
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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 Solubility0.000351 mg/mLALOGPS
logP8.39ALOGPS
logP10.4ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)7.21ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 Å2ChemAxon
Rotatable Bond Count18ChemAxon
Refractivity186.64 m3·mol-1ChemAxon
Polarizability71.95 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
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 IDFDB024100
KNApSAcK IDNot Available
Chemspider ID4444377
KEGG Compound IDC05805
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06820
Metagene LinkHMDB06820
METLIN IDNot Available
PubChem Compound5280828
PDB IDNot Available
ChEBI IDNot Available
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
2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone + S-Adenosylmethionine → Ubiquinone 6 + S-Adenosylhomocysteinedetails
General function:
Involved in oxidoreductase activity
Specific function:
Involved in lifespan determination in ubiquinone-independent manner. Involved in ubiquinone biosynthesis. Potential central metabolic regulator (By similarity).
Gene Name:
COQ7
Uniprot ID:
Q99807
Molecular weight:
Not Available
Reactions
2-Hexaprenyl-3-methyl-6-methoxy-1,4 benzoquinone + Oxygen + NADPH + Hydrogen Ion → 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone + NADP + Waterdetails