Record Information
Version2.0
Creation Date2012-05-31 14:05:43 -0600
Update Date2015-06-03 15:54:45 -0600
Secondary Accession Numbers
  • ECMDB04120
Identification
Name:2-Octaprenylphenol
Description2-octaprenylphenol belongs to the class of Tetraterpenes. These are terpene molecules containing 10 consecutively linked isoprene units. (inferred from compound structure)2-octaprenylphenol is invovled in Ubiquinone and other terpenoid-quinone biosynthesis, and Biosynthesis of secondary metabolites. (KEGG)Octaprenylphenol is the CoQ biosynthetic intermediate found to accumulate in E. Coli. (PMID 10960098)
Structure
Thumb
Synonyms:
  • 2OctPhe
Chemical Formula:C46H70O
Weight:Average: 639.0474
Monoisotopic: 638.542666862
InChI Key:VUNQJPPPTJIREN-CMAXTTDKSA-N
InChI:InChI=1S/C46H70O/c1-37(2)19-12-20-38(3)21-13-22-39(4)23-14-24-40(5)25-15-26-41(6)27-16-28-42(7)29-17-30-43(8)31-18-32-44(9)35-36-45-33-10-11-34-46(45)47/h10-11,19,21,23,25,27,29,31,33-35,47H,12-18,20,22,24,26,28,30,32,36H2,1-9H3/b38-21+,39-23+,40-25+,41-27+,42-29+,43-31+,44-35+
CAS number:42187-47-3
IUPAC Name:2-[(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-octaprenylphenol
SMILES:CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=CC=CC=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
  • Polyprenylphenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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 Solubility0.00023 g/LALOGPS
logP10.01ALOGPS
logP15.02ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)9.33ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity218.9 m³·mol⁻¹ChemAxon
Polarizability85.73 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:
Secondary Metabolites: Ubiquinol biosynthesisPW000981 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolites: Ubiquinol biosynthesis 2PW002036 ThumbThumb?image type=greyscaleThumb?image type=simple
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 GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0424269000-322a384a3ef02212506cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0564-0566590000-3fdff123d279fcc4802bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05o1-5658490000-be2af75495c1da39f687View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000009000-b29cd31348d5378f342aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000009000-14017f8ab990259592e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-2533249000-d1ebce6dc6c557c1c33fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1300195000-5b71ab74d3b16ccbbcc9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1213590000-777cdf2ad7e6a1da815aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a70-2944240000-fd950d84f0c406801d56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000009000-add616e319ed867b71f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-0611139000-66b5db033732fdb2b146View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-2600392000-db60efbad6bdcbb7085eView 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:
  • 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 ID40407
HMDB IDHMDB0304080
Pubchem Compound ID5280832
Kegg IDC05810
ChemSpider ID4444381
Wikipedia IDNot Available
BioCyc ID2-OCTAPRENYLPHENOL
EcoCyc ID2-OCTAPRENYLPHENOL
Ligand Expo8PP

Enzymes

General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the decarboxylation of 3-octaprenyl-4-hydroxy benzoate to 2-octaprenylphenol
Gene Name:
ubiD
Uniprot ID:
P0AAB4
Molecular weight:
55603
General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
Required, probably indirectly, for the hydroxylation of 2-octaprenylphenol to 2-octaprenyl-6-hydroxy-phenol, the fourth step in ubiquinone biosynthesis. Specific for aerobically grown log-phase cells
Gene Name:
ubiB
Uniprot ID:
P0A6A0
Molecular weight:
63202
General function:
Coenzyme transport and metabolism
Specific function:
Specific function unknown
Gene Name:
ubiX
Uniprot ID:
P0AG03
Molecular weight:
20695