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2-hexaprenyl-6-methoxyphenol (YMDB00440)

Identification
YMDB IDYMDB00440
Name2-hexaprenyl-6-methoxyphenol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2-Hexaprenyl-6-methoxyphenol belongs to the class of organic compounds known as 2-polyprenyl-6-methoxyphenols. 2-polyprenyl-6-methoxyphenols are compounds containing a polyisoprene chain attached at the 2-position of a 6-methoxyphenol group. Thus, 2-hexaprenyl-6-methoxyphenol is considered to be a quinone lipid molecule. 2-Hexaprenyl-6-methoxyphenol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 2-Hexaprenyl-6-methoxyphenol
  • 2-Methoxy-6-(all-trans-hexaprenyl)phenol
CAS numberNot Available
WeightAverage: 532.8393
Monoisotopic: 532.428031036
InChI KeyWVPRAWNIVDFQBO-DUBIXASGSA-N
InChIInChI=1S/C37H56O2/c1-29(2)15-9-16-30(3)17-10-18-31(4)19-11-20-32(5)21-12-22-33(6)23-13-24-34(7)27-28-35-25-14-26-36(39-8)37(35)38/h14-15,17,19,21,23,25-27,38H,9-13,16,18,20,22,24,28H2,1-8H3/b30-17+,31-19+,32-21+,33-23+,34-27+
IUPAC Name2-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-6-methoxyphenol
Traditional IUPAC Name2-hexaprenyl-6-methoxyphenol
Chemical FormulaC37H56O2
SMILESCOC1=CC=CC(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2-polyprenyl-6-methoxyphenols. 2-polyprenyl-6-methoxyphenols are compounds containing a polyisoprene chain attached at the 2-position of a 6-methoxyphenol group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenylphenols
Direct Parent2-polyprenyl-6-methoxyphenols
Alternative Parents
Substituents
  • 2-polyprenyl-6-methoxyphenol
  • Sesterterpenoid
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00033 g/LALOGPS
logP9.13ALOGPS
logP11.54ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)9.79ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity177.76 m³·mol⁻¹ChemAxon
Polarizability68.47 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
Organoleptic PropertiesNot Available
SMPDB Pathways
Ubiquinone BiosynthesisPW002473 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Ubiquinone and other terpenoid-quinone biosynthesisec00130 Map00130
SMPDB Reactions
2-hexaprenyl-6-methoxyphenol + oxygen → 2-Hexaprenyl-6-methoxy-1,4-benzoquinone + water
KEGG Reactions
oxygen + 2-hexaprenyl-6-methoxyphenol → water + 2-Hexaprenyl-6-methoxy-1,4-benzoquinone
3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid + hydron → Carbon dioxide + 2-hexaprenyl-6-methoxyphenol
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02vj-2679450000-ef75cfff1e30dc7daebfJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000i-2145290000-6daeff85e67cc774659cJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("2-Hexaprenyl-6-methoxyphenol,1TMS,#1" TMS) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0334390000-a68b489f811d58e3a0a3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-054w-0669310000-e9735735720766e04247JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-4369310000-e3fa7830ea4ca0ea25b7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000090000-5d1794e2402e3941fb4fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0100190000-c19b32a72f4a4d68368eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066s-3812970000-848e712cd68525e57486JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-4436950000-281335a4fae014fdf968JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00yr-4915100000-c88aedf3155ffcce51c9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0016-9730000000-77ebf5aed8457e946709JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000090000-83e0d6d5a68b5170e6c5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ayi-0911270000-063e0e3f493564c9e06eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1905250000-cfcce35eec4cce7a941dJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Casey, J., Threlfall, D. R. (1978). "Synthesis of 5-demethoxyubiquinone-6 and ubiquinone-6 from 3-hexaprenyl-4-hydroxybenzoate in yeast mitochondria." FEBS Lett 85:249-253.620805
  • Marbois, B., Gin, P., Faull, K. F., Poon, W. W., Lee, P. T., Strahan, J., Shepherd, J. N., Clarke, C. F. (2005). "Coq3 and Coq4 define a polypeptide complex in yeast mitochondria for the biosynthesis of coenzyme Q." J Biol Chem 280:20231-20238.15792955
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID1109
HMDB IDHMDB06817
Pubchem Compound ID5280825
Kegg IDC05802
ChemSpider ID4444374
FOODB IDFDB024097
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Ubiquinone biosynthesis protein COQ4, mitochondrial
General function:
Involved in ubiquinone biosynthetic process
Specific function:
Component of the coenzyme Q biosynthetic pathway. May play a role in organizing a multi-subunit COQ enzyme complex required for coenzyme Q biosynthesis. Required for steady-state levels of COQ3, COQ4, COQ6, COQ7 and COQ9 polypeptides
Gene Name:
COQ4
Uniprot ID:
O13525
Molecular weight:
38626.80078