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2-methoxy-6-(all-trans-octaprenyl)phenol (M2MDB003827)

Record Information
Version2.0
Creation Date2012-10-22 13:35:01 -0600
Update Date2015-06-03 17:26:44 -0600
Secondary Accession Numbers
  • ECMDB23437
Identification
Name:2-methoxy-6-(all-trans-octaprenyl)phenol
Description2-methoxy-6-(all-trans-octaprenyl)phenol is involved in the ubiquinol-8 biosynthesis pathway. It is a substrate for the 2-octaprenyl-6-methoxyphenol hydroxylase that catalyses the following reaction: 2-methoxy-6-(all-trans-octaprenyl)phenol + NADPH + oxygen + H+ => 2-methoxy-6-all trans-octaprenyl-2-methoxy-1,4-benzoquinol + NADP+ + H2O
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2-Octaprenyl-6-methoxyphenol
  • 6-methoxy-2-octaprenylphenol
Chemical Formula:C40H58O2
Weight:Average: 570.8873
Monoisotopic: 570.4436811
InChI Key:CSWHQXJYVAFCED-KBSPPPJMSA-N
InChI:InChI=1S/C40H58O2/c1-30(2)14-15-31(3)16-17-32(4)18-19-33(5)20-21-34(6)22-23-35(7)24-25-36(8)26-27-37(9)28-29-38-12-11-13-39(42-10)40(38)41/h11-14,16,18,20,22,24,26,28,41H,15,17,19,21,23,25,27,29H2,1-10H3/b31-16+,32-18+,33-20+,34-22+,35-24+,36-26+,37-28+
CAS number:Not Available
IUPAC Name:2-methoxy-6-[(2E,5E,8E,11E,14E,17E,20E)-3,6,9,12,15,18,21,24-octamethylpentacosa-2,5,8,11,14,17,20,23-octaen-1-yl]phenol
Traditional IUPAC Name:2-methoxy-6-[(2E,5E,8E,11E,14E,17E,20E)-3,6,9,12,15,18,21,24-octamethylpentacosa-2,5,8,11,14,17,20,23-octaen-1-yl]phenol
SMILES:COC1=CC=CC(C\C=C(/C)C\C=C(/C)C\C=C(/C)C\C=C(/C)C\C=C(/C)C\C=C(/C)C\C=C(/C)CC=C(C)C)=C1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00033 g/LALOGPS
logP8.92ALOGPS
logP11.75ChemAxon
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 Count17ChemAxon
Refractivity193.16 m³·mol⁻¹ChemAxon
Polarizability72.6 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-adenosyl-L-methionine + 2-Octaprenyl-6-hydroxyphenol > Hydrogen ion + S-Adenosylhomocysteine + 2-methoxy-6-(all-trans-octaprenyl)phenol
Hydrogen ion + NADPH + Oxygen + 2-methoxy-6-(all-trans-octaprenyl)phenol + NADPH > Water + NADP + 2-Octaprenyl-6-methoxy-1,4-benzoquinol
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:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00fr-0443390000-e2611ffacd6bcc7489d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-1955520000-784bc318b97421df8e6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2937520000-44966b6def682f990704View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00fr-0443390000-e2611ffacd6bcc7489d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-1955520000-784bc318b97421df8e6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2937520000-44966b6def682f990704View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-33b0abfce05062e92c9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000090000-28ae1f4f1bc610a02267View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zg0-0311190000-87e8ca04162634b98b69View in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID1235
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

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. 2-octaprenyl-6-methoxyphenol hydroxylase
General function:
Involved in oxidoreductase activity
Specific function:
Oxygenase that introduces the hydroxyl group at carbon four of 2-octaprenyl-6-methoxyphenol resulting in the formation of 2-octaprenyl-6-methoxy-1,4-benzoquinone
Gene Name:
ubiH
Uniprot ID:
P25534
Molecular weight:
42288