2-Octaprenylphenol (PAMDB000622)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000622
Identification
Name: 2-Octaprenylphenol
Description:2-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 Pseudomonas aeruginosa. (PMID 10960098)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2OctPhe
Chemical Formula: C46H70O
Average Molecular Weight: 639.0474
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as polyprenylphenols. These are compounds containing a polyisoprene chain attached to a phenol group.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Prenol lipids
Sub ClassPolyprenylphenols
Direct Parent Polyprenylphenols
Alternative Parents
Substituents
  • Polyprenylphenol
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular Framework Aromatic homomonocyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.000226 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count23ChemAxon
Refractivity218.9 m3·mol-1ChemAxon
Polarizability85.73 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
2-Octaprenylphenol + Oxygen > 2-Octaprenyl-6-hydroxyphenol
3-Octaprenyl-4-hydroxybenzoate <> 2-Octaprenylphenol + Carbon dioxide
2-Octaprenylphenol + Oxygen + NADPH + Hydrogen ion <> 2-Octaprenyl-6-hydroxyphenol + NADP + Water
Hydrogen ion + 3-Octaprenyl-4-hydroxybenzoate > 2-Octaprenylphenol + Carbon dioxide
2-Octaprenylphenol + Hydrogen ion + NADPH + Oxygen + NADPH > NADP + Water + 2-Octaprenyl-6-hydroxyphenol + 2-Octaprenyl-6-hydroxyphenol
Pathways:
  • Ubiquinone and other terpenoid-quinone biosynthesis pae00130
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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
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 IDNot Available
Pubchem Compound ID5280832
Kegg IDC05810
ChemSpider ID4444381
Wikipedia IDNot Available
BioCyc ID2-OCTAPRENYLPHENOL
EcoCyc ID2-OCTAPRENYLPHENOL
Ligand Expo8PP

Enzymes

Protein Details
• 3-octaprenyl-4-hydroxybenzoate carboxy-lyase
General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the decarboxylation of 3-octaprenyl-4-hydroxy benzoate to 2-octaprenylphenol
Gene Name:
ubiD
Locus Tag:
PA5237
Molecular weight:
54.6 kDa
Protein Details
• Probable ubiquinone biosynthesis protein ubiB
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
Locus Tag:
PA5065
Molecular weight:
61.7 kDa