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2-Octaprenyl-6-methoxyphenol (M2MDB000621)

Record Information
Version2.0
Creation Date2012-05-31 14:05:40 -0600
Update Date2015-09-17 16:24:11 -0600
Secondary Accession Numbers
  • ECMDB04119
Identification
Name:2-Octaprenyl-6-methoxyphenol
Description2-octaprenyl-6-methoxyphenol belongs to the class of Tetraterpenes. These are terpene molecules containing 10 consecutively linked isoprene units. (inferred from compound structure)2-octaprenyl-6-methoxyphenol is invovled in Ubiquinone and other terpenoid-quinone biosynthesis, and Biosynthesis of secondary metabolites. (KEGG)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2Oct6MethPhe
Chemical Formula:C47H72O2
Weight:Average: 669.0734
Monoisotopic: 668.553231548
InChI Key:MARGKPIMNMASKJ-UHFFFAOYSA-N
InChI:InChI=1S/C47H72O2/c1-37(2)19-11-20-38(3)21-12-22-39(4)23-13-24-40(5)25-14-26-41(6)27-15-28-42(7)29-16-30-43(8)31-17-32-44(9)35-36-45-33-18-34-46(49-10)47(45)48/h18-19,21,23,25,27,29,31,33-35,48H,11-17,20,22,24,26,28,30,32,36H2,1-10H3
CAS number:Not Available
IUPAC Name:2-methoxy-6-[(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]phenol
Traditional IUPAC Name:2-octaprenyl-6-methoxyphenol
SMILES:COC1=CC=CC(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as polyprenylphenols. Polyprenylphenols are compounds containing a polyisoprene chain attached to a phenol group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenylphenols
Direct ParentPolyprenylphenols
Alternative Parents
Substituents
  • Tetraterpenoid
  • 2-polyprenyl-6-methoxyphenol
  • Polyprenylphenol
  • Methoxyphenol
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00022 g/LALOGPS
logP9.82ALOGPS
logP14.86ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)9.79ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity225.36 m³·mol⁻¹ChemAxon
Polarizability87.2 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-hydroxyphenol + S-Adenosylmethionine > 2-Octaprenyl-6-methoxyphenol + S-Adenosylhomocysteine + Hydrogen ion
2-Octaprenyl-6-methoxyphenol + Oxygen > 2-Octaprenyl-6-methoxy-1,4-benzoquinol
2-Octaprenyl-6-hydroxyphenol + S-Adenosylmethionine <> 2-Octaprenyl-6-methoxyphenol + S-Adenosylhomocysteine
2-Octaprenyl-6-methoxyphenol + Oxygen + NADPH <> 2-octaprenyl-6-methoxy-1,4-benzoquinone + NADP + Water
2-Octaprenyl-6-methoxyphenol + Oxygen + NADPH + Hydrogen ion > 2-Octaprenyl-6-methoxy-1,4-benzoquinol + Water + NADP
2 2-Octaprenyl-6-hydroxyphenol + S-Adenosylmethionine >2 2-Octaprenyl-6-methoxyphenol + S-Adenosylhomocysteine + Hydrogen ion
SMPDB Pathways:Not Available
KEGG Pathways:
  • Ubiquinone and other terpenoid-quinone biosynthesis ec00130
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-0322129000-085ed40d6f05b416c88aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0040-1868693000-fe780219954b71dad65eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5a-2459861000-fe3030ebe2cdae6a3265View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000009000-c5dcfefef14d1d6e7b72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000009000-de948d73be7513e03b59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbi-1200029000-53d3c277985257b24d42View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID1235
HMDB IDNot Available
Pubchem Compound ID5280834
Kegg IDC05812
ChemSpider ID4444383
Wikipedia IDNot Available
BioCyc ID2-OCTAPRENYL-6-METHOXYPHENOL
EcoCyc ID2-OCTAPRENYL-6-METHOXYPHENOL

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-6-methoxyphenol hydroxylase
General function:
Involved in oxidoreductase activity
Specific function:
Oxygenase that introduces the hydroxyl group at carbon four of 2-octaprenyl-6-methoxyphenol resulting in the formation of 2-octaprenyl-6-methoxy-1,4-benzoquinone
Gene Name:
ubiH
Uniprot ID:
P25534
Molecular weight:
42288