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Record Information
Version3.6
Creation Date2008-08-12 14:32:35 UTC
Update Date2016-02-11 01:07:58 UTC
HMDB IDHMDB06819
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Hexaprenyl-3-methyl-6-methoxy-1,4 benzoquinone
Description2-Hexaprenyl-3-methyl-6-methoxy-1,4 benzoquinone is involved in the ubiquinone biosynthesis pathway. 2-Hexaprenyl-3-methyl-6-methoxy-1,4 benzoquinone is created from 2-Hexaprenyl-6-methoxy-1,4-benzoquinone by ubiquinone biosynthesis methyltransferase [EC:2.1.1.-]. 2-Hexaprenyl-3-methyl-6-methoxy-1,4 benzoquinone is then converted to 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone by ubiquinone biosynthesis monooxygenase Coq7 [EC:1.14.13.-].
Structure
Thumb
Synonyms
ValueSource
2-Hexaprenyl-3-methyl-6-methoxy-1,4-benzoquinoneChEBI
Chemical FormulaC38H56O3
Average Molecular Weight560.8494
Monoisotopic Molecular Weight560.422945658
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-dione
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-dione
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)C1=O
InChI Identifier
InChI=1S/C38H56O3/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/h15,17,19,21,23,25,27H,10-14,16,18,20,22,24,26H2,1-9H3/b29-17+,30-19+,31-21+,32-23+,33-25+
InChI KeyInChIKey=RLVSEUWSBSQQOE-NSUIJKAQSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as polyprenylbenzoquinones. These are compounds containing a polyisoprene chain attached to a quinone at the second ring position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentPolyprenylbenzoquinones
Alternative Parents
Substituents
  • Polyprenylbenzoquinone
  • Sesterterpenoid
  • Quinone
  • P-benzoquinone
  • Vinylogous ester
  • Cyclic ketone
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
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 Solubility0.000374 mg/mLALOGPS
logP8.47ALOGPS
logP10.92ChemAxon
logS-6.2ALOGPS
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 Å2ChemAxon
Rotatable Bond Count18ChemAxon
Refractivity184.68 m3·mol-1ChemAxon
Polarizability70.85 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
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 IDFDB024099
KNApSAcK IDNot Available
Chemspider ID4444376
KEGG Compound IDC05804
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06819
Metagene LinkHMDB06819
METLIN IDNot Available
PubChem Compound5280827
PDB IDNot Available
ChEBI ID28711
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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
General function:
Involved in methyltransferase activity
Specific function:
Methyltransferase required for the conversion of 2-polyprenyl-6-methoxy-1,4-benzoquinol (DDMQH2) to 2-polyprenyl-3-methyl-6-methoxy-1,4-benzoquinol (DMQH2) (By similarity).
Gene Name:
COQ5
Uniprot ID:
Q5HYK3
Molecular weight:
37140.17
Reactions
2-Hexaprenyl-6-methoxy-1,4-benzoquinone + S-Adenosylmethionine → 2-Hexaprenyl-3-methyl-6-methoxy-1,4 benzoquinone + S-Adenosylhomocysteinedetails