2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol (YMDB00953)

Identification
YMDB IDYMDB00953
Name2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol, also known as demethyl-ubiquinol-6, 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. Based on a literature review a small amount of articles have been published on 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • Demethyl-ubiquinol-6
CAS numberNot Available
WeightAverage: 578.8647
Monoisotopic: 578.433510344
InChI KeyZQXNZNKHQXLVCV-HGJBZHBGSA-N
InChIInChI=1S/C38H58O4/c1-27(2)15-10-16-28(3)17-11-18-29(4)19-12-20-30(5)21-13-22-31(6)23-14-24-32(7)25-26-34-33(8)35(39)37(41)38(42-9)36(34)40/h15,17,19,21,23,25,39-41H,10-14,16,18,20,22,24,26H2,1-9H3/b28-17+,29-19+,30-21+,31-23+,32-25+
IUPAC Name5-[(2Z,6E,10E,14E,18Z)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-3-methoxy-6-methylbenzene-1,2,4-triol
Traditional IUPAC Name5-[(2Z,6E,10E,14E,18Z)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-3-methoxy-6-methylbenzene-1,2,4-triol
Chemical FormulaC38H58O4
SMILES[H]OC1=C(OC([H])([H])[H])C(O[H])=C(C(=C1O[H])C([H])([H])[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]
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
  • Polyprenylbenzoquinol
  • Sesterterpenoid
  • Prenylbenzoquinol
  • Ubiquinol skeleton
  • Methoxyphenol
  • Hydroxyquinol derivative
  • Anisole
  • Phenoxy compound
  • M-cresol
  • O-cresol
  • Phenol ether
  • Methoxybenzene
  • Phenol
  • Alkyl aryl ether
  • Toluene
  • Monocyclic benzene moiety
  • Benzenoid
  • Ether
  • Polyol
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00064 g/LALOGPS
logP8.32ALOGPS
logP11.45ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)9.96ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.92 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity186.76 m³·mol⁻¹ChemAxon
Polarizability72.49 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08ml-2298480000-2cbb61853354b11007ecJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000i-3147469000-5fdc766ff10e478f5f01JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol,1TMS,#1" TMS) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0213090000-4a65137eb42195f434deJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0035-1549230000-463e4c4d13762fa9850aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-3269420000-40341ce89f21aa25ad3dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000090000-6ffefbe22ee39bd8d207JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1000190000-c35bad59002e8ccdf17fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-076r-5200980000-8112877d445f435d22c7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00or-5226590000-6dda2e5d3269dc410c73JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9648220000-9470cbdf01957ebc558fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0536-9513000000-2ef87b7732dc77930914JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000090000-121478cabf4ee3db57a1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-0610290000-23fcf10e704d6d40fa38JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-1533920000-0d9f372f51b6e522994eJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB12146
Pubchem Compound ID25203764
Kegg IDNot Available
ChemSpider ID30776599
FOODB IDFDB028803
Wikipedia IDNot Available
BioCyc ID2-HEXAPRENYL-3-METHYL-5-HYDROXY-6-METHOX

Enzymes

Protein Details
1. Hexaprenyldihydroxybenzoate methyltransferase, mitochondrial
General function:
Involved in methyltransferase activity
Specific function:
Non-specific O-methyltransferase that catalyzes the 2 O- methylation steps in the ubiquinone biosynthetic pathway
Gene Name:
COQ3
Uniprot ID:
P27680
Molecular weight:
36330.60156
Reactions
S-adenosyl-L-methionine + 3,4-dihydroxy-5-all-trans-polyprenylbenzoate → S-adenosyl-L-homocysteine + 3-methoxy-4-hydroxy-5-all-trans-polyprenylbenzoate.
S-adenosyl-L-methionine + 3-demethylubiquinone-n → S-adenosyl-L-homocysteine + ubiquinone-n.
S-adenosyl-L-methionine + 2-hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol → S-adenosyl-L-homocysteine + ubiquinol.