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Record Information
Version4.0
Creation Date2008-08-12 14:36:36 UTC
Update Date2017-10-23 19:04:25 UTC
HMDB IDHMDB0006820
Secondary Accession Numbers
  • HMDB06820
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 KeyIALHZQNPELKEGE-HGJBZHBGSA-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
  • Quinone
  • O-benzoquinone
  • Vinylogous acid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
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 Solubility0.00035 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity186.64 m³·mol⁻¹ChemAxon
Polarizability71.95 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, Positivesplash10-06y9-2197580000-76798e00092a2c131cafView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-003r-3147469000-8e87818f8a300107677eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0213190000-920b7c37f14e9166fd52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-055e-0549230000-d8a6fac96d7d16b96682View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-2124910000-a366c27333a192119553View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000190000-3f54bfed75c669f7dc33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00vi-2000190000-f1b2a4654166322d6bb1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9200760000-68e907ef0147e68a9d30View 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 IDFDB024100
KNApSAcK IDNot Available
Chemspider ID4444377
KEGG Compound IDC05805
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
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