6-Methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol (ECMDB23436) (M2MDB003826)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (2)
Record Information
Version2.0
Creation Date2012-10-22 13:35:01 -0600
Update Date2015-06-03 17:26:44 -0600
Secondary Accession Numbers
  • ECMDB23436
Identification
Name:6-Methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol
Description6-Methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol is involved in the ubiquinol-8 biosynthesis pathway. It is a substrate of 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinone hydroxylase that catalyses the following reaction: 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol + a reduced electron acceptor + oxygen => 3-demethylubiquinol-8 + an oxidized electron acceptor + H2O
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:Not Available
Chemical Formula:C46H70O3
Weight:Average: 671.0462
Monoisotopic: 670.532496106
InChI Key:CRUUXCIHJFUTIZ-WZVGXJGASA-N
InChI:InChI=1S/C46H70O3/c1-34(2)27-28-41(9)30-29-39(7)25-15-23-37(5)21-13-19-35(3)17-12-18-36(4)20-14-22-38(6)24-16-26-40(8)31-32-43-42(10)44(47)33-45(49-11)46(43)48/h17,20-21,24-25,27,30-31,33,47-48H,12-16,18-19,22-23,26,28-29,32H2,1-11H3/b35-17+,36-20+,37-21+,38-24+,39-25+,40-31+,41-30+
CAS number:Not Available
IUPAC Name:5-methoxy-2-methyl-3-[(2E,6E,10E,14E,18E,22E,25E)-3,7,11,15,19,23,26,29-octamethyltriaconta-2,6,10,14,18,22,25,28-octaen-1-yl]benzene-1,4-diol
Traditional IUPAC Name:5-methoxy-2-methyl-3-[(2E,6E,10E,14E,18E,22E,25E)-3,7,11,15,19,23,26,29-octamethyltriaconta-2,6,10,14,18,22,25,28-octaen-1-yl]benzene-1,4-diol
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)CC\C=C(/C)C\C=C(/C)CC=C(C)C)=C(C)C(O)=C1
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2-polyprenyl-6-methoxyphenols. 2-polyprenyl-6-methoxyphenols are compounds containing a polyisoprene chain attached at the 2-position of a 6-methoxyphenol group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenylphenols
Direct Parent2-polyprenyl-6-methoxyphenols
Alternative Parents
Substituents
  • 2-polyprenyl-6-methoxyphenol
  • Polyprenylbenzoquinol
  • Sesterterpenoid
  • Prenylbenzoquinol
  • Methoxyphenol
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • O-cresol
  • M-cresol
  • Hydroquinone
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Toluene
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00028 g/LALOGPS
logP9.24ALOGPS
logP14.18ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)9.98ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity223.18 m³·mol⁻¹ChemAxon
Polarizability85.91 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
2-Octaprenyl-6-methoxy-1,4-benzoquinol + S-adenosyl-L-methionine > S-Adenosylhomocysteine + Hydrogen ion + 6-Methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol
Oxygen + Reduced acceptor + 6-Methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol > Water + oxidized electron acceptor + 3-demethylubiquinol-8
SMPDB Pathways:
Secondary Metabolites: Ubiquinol biosynthesisPW000981 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0221229000-fc661d3ce4b8ec708206View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-0697784000-61ea24af909b8f4eaeaaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1299-0497741000-99e4dc3be0546c0018d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000009000-7ec3740028f154d9651fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000009000-30798e5bd8328f980a0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-2400079000-a2f5bffa69a3a8b673c0View in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol hydroxylase
General function:
Involved in oxidoreductase activity
Specific function:
Oxygenase that introduces the hydroxyl group at carbon five of 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol resulting in the formation of 2-octaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4- benzoquinol
Gene Name:
ubiF
Uniprot ID:
P75728
Molecular weight:
42953
Protein Details
2. Ubiquinone/menaquinone biosynthesis methyltransferase ubiE
General function:
Involved in methyltransferase activity
Specific function:
Methyltransferase required for the conversion of dimethylmenaquinone (DMKH2) to menaquinone (MKH2) and the conversion of 2-polyprenyl-6-methoxy-1,4-benzoquinol (DDMQH2) to 2-polyprenyl-3-methyl-6-methoxy-1,4-benzoquinol (DMQH2)
Gene Name:
ubiE
Uniprot ID:
P0A887
Molecular weight:
28073
Reactions
A demethylmenaquinone + S-adenosyl-L-methionine = a menaquinol + S-adenosyl-L-homocysteine.
S-adenosyl-L-methionine + 2-methoxy-6-all-trans-polyprenyl-1,4-benzoquinol = S-adenosyl-L-homocysteine + 6-methoxy-3-methyl-2-all-trans-polyprenyl-1,4-benzoquinol.