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Record Information
Version1.0
Creation date2011-09-21 01:45:10 UTC
Update date2015-07-21 06:59:32 UTC
Primary IDFDB028803
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol
Description2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol is an ubiquinone derivative that is an intermediate in ubiquinone-6 biosynthesis. Ubiquinone (also known as coenzyme Q) is an isoprenoid quinone that functions as an electron carrier in membranes. In eukaryotes ubiquinone is found mostly within the inner mitochondrial membrane, where it functions in respiratory electron transport, transferring two electrons from either complex I (NADH dehydrogenase) or complex II (succinate-ubiquinone reductase) to complex III (bc1 complex). The quinone nucleus of ubiquinone is derived directly from 4-hydroxybenzoate , while the isoprenoid subunits of the polyisoprenoid tail are synthesized via the methylerythritol phosphate pathway , which feeds isoprene units into the Polyprenyl Biosynthesis pathways. The number of isoprenoid subunits in the ubiquinone side chain vary in different species. For example, Saccharomyces cerevisiae subsp (S288c) has 6 such subunits, Escherichia coli K-12 has 8, rat and mouse have 9, and Homo sapiens has 10. The ubiquinones are often named according to the number of carbons in the side chain or the number of isoprenoid subunits. The ubiquinone biosynthesis pathway has been elucidated primarily by the use of mutant strains that accumulate pathway intermediates. 2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol is a substrate for hexaprenyldihydroxybenzoate methyltransferase, mitochondrial precursor (COQ3) and can be generated from 2-hexaprenyl-3-methyl-6-methoxy-1,4-benzoquinol. Then it can be converted to ubiquinol-6.(BioCyc) [HMDB]
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
Demethyl-ubiquinol-6hmdb
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
Polarizability71.95 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC38H58O4
IUPAC name5-(3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl)-3-methoxy-6-methylbenzene-1,2,4-triol
InChI IdentifierInChI=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
InChI KeyZQXNZNKHQXLVCV-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C(O)=C(C)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C1O
Average Molecular Weight578.8647
Monoisotopic Molecular Weight578.433510344
Classification
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 Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0223090000-b88415f8ab98c03b0236Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-057m-0559320000-f6490956093a57f92771Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02ta-2159330000-027f8b5b335675eb54a6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000090000-c564548158d374603de8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1000090000-3b9a39a3ce2d93aecdc9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-074j-7300790000-a42ccf697f15d05021a2Spectrum
NMRNot Available
ChemSpider ID30776599
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53481381
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12146
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference