2-Octaprenyl-6-methoxyphenol (PAMDB000621)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000621
Identification
Name: 2-Octaprenyl-6-methoxyphenol
Description:2-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
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2Oct6MethPhe
Chemical Formula: C47H72O2
Average Molecular Weight: 669.0734
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionNot Available
Kingdom Not Available
Super ClassNot Available
Class Not Available
Sub ClassNot Available
Direct Parent Not Available
Alternative Parents Not Available
Substituents Not Available
Molecular Framework Not Available
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.000216 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count24ChemAxon
Refractivity225.36 m3·mol-1ChemAxon
Polarizability87.2 Å3ChemAxon
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 + Hydrogen ion > 2-Octaprenyl-6-methoxy-1,4-benzoquinol + Water + NADP
Pathways:
  • Ubiquinone and other terpenoid-quinone biosynthesis pae00130
Spectra
Spectra:
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
• 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
Locus Tag:
PA3171
Molecular weight:
25.9 kDa
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-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
Locus Tag:
PA5223
Molecular weight:
43 kDa