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Record Information
Version	2.0
Creation Date	2012-05-31 14:05:43 -0600
Update Date	2015-06-03 15:54:45 -0600
Secondary Accession Numbers	ECMDB04120
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 E. Coli. (PMID 10960098)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xace47b98> Close
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.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Prenol lipids
Sub Class	Polyprenylphenols
Direct Parent	Polyprenylphenols
Alternative Parents	Tetraterpenoids 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Organooxygen compounds Hydrocarbon derivatives
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 Framework	Aromatic homomonocyclic compounds
External Descriptors	phenols (CHEBI:40407 ) fatty alcohol (CHEBI:40407 )
Physical Properties
State:	Not Available
Charge:	0
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.00023 g/L ALOGPS logP 10.01 ALOGPS logP 15.02 ChemAxon logS -6.5 ALOGPS pKa (Strongest Acidic) 9.33 ChemAxon pKa (Strongest Basic) -6 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 1 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 20.23 Ų ChemAxon Rotatable Bond Count 23 ChemAxon Refractivity 218.9 m³·mol⁻¹ ChemAxon Polarizability 85.73 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Membrane
Reactions:	3-Octaprenyl-4-hydroxybenzoate + Hydrogen ion > 2-Octaprenylphenol + Carbon dioxide 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 2-Octaprenylphenol + Oxygen + NADPH + Hydrogen ion > 2-Octaprenyl-6-hydroxyphenol + Water + NADP 2-Octaprenylphenol + Hydrogen ion + NADPH + Oxygen + NADPH > NADP + Water + 2-Octaprenyl-6-hydroxyphenol + 2-Octaprenyl-6-hydroxyphenol 2 2-Octaprenylphenol + Oxygen + NADPH + Hydrogen ion <>2 2-Octaprenyl-6-hydroxyphenol + NADP + Water 3 3-Octaprenyl-4-hydroxybenzoate + Hydrogen ion >2 2-Octaprenylphenol + Carbon dioxide 2 2-Octaprenylphenol + Oxygen + NADPH + Hydrogen ion <>2 2-Octaprenyl-6-hydroxyphenol + NADP + Water
SMPDB Pathways:	Secondary Metabolites: Ubiquinol biosynthesis PW000981 Secondary Metabolites: Ubiquinol biosynthesis 2 PW002036
KEGG Pathways:	Ubiquinone and other terpenoid-quinone biosynthesis ec00130
EcoCyc Pathways:	ubiquinol-8 biosynthesis (prokaryotic) PWY-6708
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-000i-0424269000-322a384a3ef02212506c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0564-0566590000-3fdff123d279fcc4802b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-05o1-5658490000-be2af75495c1da39f687 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-000i-0000009000-b29cd31348d5378f342a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-000i-0000009000-14017f8ab990259592e7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-00di-2533249000-d1ebce6dc6c557c1c33f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-000i-1300195000-5b71ab74d3b16ccbbcc9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-004i-1213590000-777cdf2ad7e6a1da815a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a70-2944240000-fd950d84f0c406801d56 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-000i-0000009000-add616e319ed867b71f8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-052r-0611139000-66b5db033732fdb2b146 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0udi-2600392000-db60efbad6bdcbb7085e View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View 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
Links
External Links:	Resource Link CHEBI ID 40407 HMDB ID HMDB0304080 Pubchem Compound ID 5280832 Kegg ID C05810 ChemSpider ID 4444381 Wikipedia ID Not Available BioCyc ID 2-OCTAPRENYLPHENOL EcoCyc ID 2-OCTAPRENYLPHENOL Ligand Expo 8PP

Enzymes