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Record Information
Version4.0
Creation Date2008-08-12 14:29:56 UTC
Update Date2017-09-27 08:24:48 UTC
HMDB IDHMDB0006818
Secondary Accession Numbers
  • HMDB06818
Metabolite Identification
Common Name2-Hexaprenyl-6-methoxy-1,4-benzoquinone
Description2-Hexaprenyl-6-methoxy-1,4-benzoquinone is involved in the ubiquinone biosynthesis pathway. 2-Hexaprenyl-6-methoxy-1,4-benzoquinone is created from 2-Hexaprenyl-6-methoxyphenol by ubiquinone biosynthesis monooxygenase Coq6 [EC:1.14.13.-]. 2-Hexaprenyl-6-methoxy-1,4-benzoquinone is then converted into 2-Hexaprenyl-3-methyl-6-methoxy-1,4-benzoquinone by ubiquinone biosynthesis methyltransferase [EC:2.1.1.-].
Structure
Thumb
Synonyms
ValueSource
2-Polyprenyl-6-methoxy-1,4-benzoquinolHMDB
DDMQH2HMDB
Chemical FormulaC37H54O3
Average Molecular Weight546.8229
Monoisotopic Molecular Weight546.407295594
IUPAC Name2-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-6-methoxycyclohexa-2,5-diene-1,4-dione
Traditional Name2-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-6-methoxycyclohexa-2,5-diene-1,4-dione
CAS Registry NumberNot Available
SMILES
COC1=CC(=O)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/C37H54O3/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)27-36(40-8)37(34)39/h14,16,18,20,22,24,26-27H,9-13,15,17,19,21,23,25H2,1-8H3/b29-16+,30-18+,31-20+,32-22+,33-24+
InChI KeySCPRZSDIZDIQOW-FRICUITQSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as polyprenylbenzoquinones. These are compounds containing a polyisoprene chain attached to a quinone at the second ring position.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassPrenol lipids
Direct ParentPolyprenylbenzoquinones
Alternative Parents
Substituents
  • Polyprenylbenzoquinone
  • Sesterterpenoid
  • Quinone
  • P-benzoquinone
  • Vinylogous ester
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic 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
logP8.41ALOGPS
logP10.53ChemAxon
logS-6.2ALOGPS
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity180.32 m³·mol⁻¹ChemAxon
Polarizability69.04 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, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1122090000-ba2655d411b93ef8fbb5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0479520000-8e7c5aaeb9fd993e7e59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lj-5389820000-c681b8bdedfe3c9481bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000090000-4487eac63a220f28941bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0000190000-3901c58bd6201adcfdf1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06vi-5210490000-9fa6e69a66925ea89c1fView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB024098
KNApSAcK IDNot Available
Chemspider ID4444375
KEGG Compound IDC05803
BioCyc IDCPD-11655
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280826
PDB IDNot Available
ChEBI ID27752
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
COQ6
Uniprot ID:
Q9Y2Z9
Molecular weight:
Not Available
Reactions
2-Hexaprenyl-6-methoxyphenol + Oxygen → 2-Hexaprenyl-6-methoxy-1,4-benzoquinone + Waterdetails