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2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol (M2MDB001566)

Record Information
Version2.0
Creation Date2012-07-30 14:54:42 -0600
Update Date2015-06-03 17:20:46 -0600
Secondary Accession Numbers
  • ECMDB21157
Identification
Name:2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol
Description2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol belongs to the class of Tetraterpenes. These are terpene molecules containing 10 consecutively linked isoprene units. (inferred from compound structure)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol
  • 2Oct3Me6Meth1,4BQ
  • 6-Methoxy-3-methyl-2-octaprenyl-1,4-benzoquinol
Chemical Formula:C48H76O3
Weight:Average: 701.1152
Monoisotopic: 700.579446298
InChI Key:GCGITSVDDBZRNB-KFSSTAEESA-N
InChI:InChI=1S/C48H76O3/c1-36(2)19-12-20-37(3)21-13-22-38(4)23-14-24-39(5)25-15-26-40(6)27-16-28-41(7)29-17-30-42(8)31-18-32-43(9)33-34-45-44(10)46(49)35-47(51-11)48(45)50/h19,21,23,25,27,29,31,33,35,46,48-50H,12-18,20,22,24,26,28,30,32,34H2,1-11H3/b37-21+,38-23+,39-25+,40-27+,41-29+,42-31+,43-33+
CAS number:Not Available
IUPAC Name:5-methoxy-2-methyl-3-[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-yl]cyclohexa-2,5-diene-1,4-diol
Traditional IUPAC Name:5-methoxy-2-methyl-3-[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-yl]cyclohexa-2,5-diene-1,4-diol
SMILES:[H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC1=C(C)C(O)C=C(OC)C1O)=C(\C)CCC=C(C)C
Chemical Taxonomy
Description belongs to the class of organic compounds known as polyterpenoids. These are terpenoids consisting of more than eight isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyterpenoids
Direct ParentPolyterpenoids
Alternative Parents
Substituents
  • Polyterpenoid
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00035 g/LALOGPS
logP8.72ALOGPS
logP12.56ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)13.24ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity233.59 m³·mol⁻¹ChemAxon
Polarizability90.99 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol + Oxygen > 2-Octaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol
2-Octaprenyl-6-methoxy-1,4-benzoquinol + S-Adenosylmethionine > 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol + S-Adenosylhomocysteine + Hydrogen ion
2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol + Oxygen + a reduced electron acceptor > 2-octaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone + Water + an oxidized electron acceptor
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:
  • ubiquinol-8 biosynthesis (prokaryotic) PWY-6708
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0201129300-b370fd90c550be15594dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0935473000-8b2674a6e3a93817872dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kaj-1888791000-94ff8725c06c7e8da687View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000009000-d448fee2cccb2ff33d80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-0000009000-92cbfd128078572fcb92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2000019000-b0c83fb8fbb6ae19b855View in MoNA
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:
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID60656
HMDB IDNot Available
Pubchem Compound ID49852330
Kegg IDC05814
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDOCTAPRENYL-METHYL-METHOXY-BENZQ
EcoCyc IDOCTAPRENYL-METHYL-METHOXY-BENZQ

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.