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2-Octaprenyl-6-hydroxyphenol (M2MDB000619)

Record Information
Version2.0
Creation Date2012-05-31 14:05:33 -0600
Update Date2015-09-17 15:42:07 -0600
Secondary Accession Numbers
  • ECMDB04117
Identification
Name:2-Octaprenyl-6-hydroxyphenol
Description2-octaprenyl-6-hydroxyphenol belongs to the class of Tetraterpenes. These are terpene molecules containing 10 consecutively linked isoprene units. (inferred from compound structure)2-octaprenyl-6-hydroxyphenol is invovled in Ubiquinone and other terpenoid-quinone biosynthesis, and Biosynthesis of secondary metabolites. (KEGG)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2-octaprenyl-6-hydroxyphenol
  • 2Oct6Hphe
Chemical Formula:C48H74
Weight:Average: 651.12
Monoisotopic: 650.579052383
InChI Key:QLVBFESDHCWPKC-WQWYCSGDSA-N
InChI:InChI=1S/C48H74/c1-38(2)20-12-21-39(3)22-13-23-40(4)24-14-25-41(5)26-15-27-42(6)28-16-29-43(7)30-17-31-44(8)32-18-33-45(9)36-37-48-35-19-34-46(10)47(48)11/h19-20,22,24,26,28,30,32,34-36H,12-18,21,23,25,27,29,31,33,37H2,1-11H3/b39-22+,40-24+,41-26+,42-28+,43-30+,44-32+,45-36+
CAS number:Not Available
IUPAC Name:3-[(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]benzene-1,2-diol
Traditional IUPAC Name:2-octaprenyl-6-hydroxyphenol
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=C(C)C(C)=CC=C1
Chemical Taxonomy
Description belongs to the class of organic compounds known as polyprenylbenzene-1,2-diols. Polyprenylbenzene-1,2-diols are compounds containing a polyisoprene chain attached to a catechol group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenylphenols
Direct ParentPolyprenylbenzene-1,2-diols
Alternative Parents
Substituents
  • Tetraterpenoid
  • Polyprenylbenzene-1,2-diol
  • Catechol
  • 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 Solubility0.00029 g/LALOGPS
logP9.71ALOGPS
logP14.71ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)9.21ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity220.88 m³·mol⁻¹ChemAxon
Polarizability85.11 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-Octaprenylphenol + Oxygen > 2-Octaprenyl-6-hydroxyphenol
2-Octaprenylphenol + Oxygen + NADPH + Hydrogen ion <> 2-Octaprenyl-6-hydroxyphenol + NADP + Water
2-Octaprenyl-6-hydroxyphenol + S-Adenosylmethionine <> 2-Octaprenyl-6-methoxyphenol + S-Adenosylhomocysteine
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-Octaprenyl-6-hydroxyphenol + S-adenosyl-L-methionine + 2-Octaprenyl-6-hydroxyphenol > Hydrogen ion + S-Adenosylhomocysteine + 2-methoxy-6-(all-trans-octaprenyl)phenol
2 2-Octaprenyl-6-hydroxyphenol + S-Adenosylmethionine >2 2-Octaprenyl-6-methoxyphenol + S-Adenosylhomocysteine + Hydrogen ion
2 2-Octaprenylphenol + Oxygen + NADPH + Hydrogen ion <>2 2-Octaprenyl-6-hydroxyphenol + NADP + Water
2 2-Octaprenylphenol + Oxygen + NADPH + Hydrogen ion <>2 2-Octaprenyl-6-hydroxyphenol + NADP + Water
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 LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0312129000-8437c33863881ba7cea8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00c0-1649470000-47757fd3ad962efe01faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053s-2569570000-1c4e1b069dfcdcd925eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000009000-a53175b2cb988cc5146bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0100019000-c057a57e9add40db6431View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052r-1512159000-823d19cfee76969e3a65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0awj-0101194000-b5bbec2d16e420258dacView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-009l-2013692000-6571234a6177920be7b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05di-0837980000-9f0d8c8c654814d9f342View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000009000-1be28d88036bf99e5c80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0210129000-fcd884fe58e375a3d4c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5i-0912312000-a591ae46754aa6bd1a86View 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 ID1233
HMDB IDHMDB0304113
Pubchem Compound ID5280833
Kegg IDC05811
ChemSpider ID4444382
Wikipedia IDNot Available
BioCyc ID2-OCTAPRENYL-6-HYDROXYPHENOL
EcoCyc ID2-OCTAPRENYL-6-HYDROXYPHENOL

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. 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
Uniprot ID:
P0A6A0
Molecular weight:
63202