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2-Octaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol (M2MDB001565)

Record Information
Version2.0
Creation Date2012-07-30 14:54:42 -0600
Update Date2015-06-03 17:20:46 -0600
Secondary Accession Numbers
  • ECMDB21156
Identification
Name:2-Octaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol
Description2-octaprenyl-3-methyl-5-hydroxy-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)2-octaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol is invovled in Ubiquinone and other terpenoid-quinone biosynthesis, and Biosynthesis of secondary metabolites. (KEGG)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2-Octaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol
  • 2-Octaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone
  • 3-Demethylubiquinol-8
  • 3-Methoxy-6-methyl-5-[(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]benzene-1,2,4-triol
  • OMHMB
Chemical Formula:C48H75O4
Weight:Average: 716.1067
Monoisotopic: 715.566535888
InChI Key:PQRHUHISITYRPH-WDXILIIOSA-M
InChI:InChI=1S/C48H76O4/c1-35(2)19-12-20-36(3)21-13-22-37(4)23-14-24-38(5)25-15-26-39(6)27-16-28-40(7)29-17-30-41(8)31-18-32-42(9)33-34-44-43(10)45(49)47(51)48(52-11)46(44)50/h19,21,23,25,27,29,31,33,45-46,49-51H,12-18,20,22,24,26,28,30,32,34H2,1-11H3/p-1/b36-21+,37-23+,38-25+,39-27+,40-29+,41-31+,42-33+
CAS number:Not Available
IUPAC Name:3,6-dihydroxy-2-methoxy-5-methyl-4-[(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-1,4-dien-1-olate
Traditional IUPAC Name:3,6-dihydroxy-2-methoxy-5-methyl-4-[(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-1,4-dien-1-olate
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([O-])=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
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Organic anion
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00038 g/LALOGPS
logP8.5ALOGPS
logP11.88ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)6.26ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area72.75 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity246.03 m³·mol⁻¹ChemAxon
Polarizability91.39 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-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol + S-Adenosylmethionine > S-Adenosylhomocysteine + Hydrogen ion + Ubiquinol-8
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 LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000900-999aef614d83072a95aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1000000900-3777f4a8adf612c082f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05xu-9011276300-f13f873b17d98bb61e29View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000900-ebf931ad42a361660f85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000000900-14c097c9684bb63bc8adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-6000003900-75a4d2a2fe9f33c4da49View in MoNA
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 ID61705
HMDB IDNot Available
Pubchem Compound ID50986110
Kegg IDC05815
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDOCTAPRENYL-METHYL-OH-METHOXY-BENZQ
EcoCyc IDOCTAPRENYL-METHYL-OH-METHOXY-BENZQ

Enzymes

Protein Details
1. 3-demethylubiquinone-9 3-methyltransferase
General function:
Involved in 2-polyprenyl-6-methoxy-1,4-benzoquinone methyltransferase activity
Specific function:
S-adenosyl-L-methionine + 3- demethylubiquinone-9 = S-adenosyl-L-homocysteine + ubiquinone-9
Gene Name:
ubiG
Uniprot ID:
P17993
Molecular weight:
26555
Reactions
S-adenosyl-L-methionine + 3-demethylubiquinone-n = S-adenosyl-L-homocysteine + ubiquinone-n.
S-adenosyl-L-methionine + 3-(all-trans-polyprenyl)benzene-1,2-diol = S-adenosyl-L-homocysteine + 2-methoxy-6-(all-trans-polyprenyl)phenol.
Protein Details
2. 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