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Showing Compound 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol (FDB028352)

Record Information
Version1.0
Creation date2011-09-21 01:38:25 UTC
Update date2015-07-21 06:59:23 UTC
Primary IDFDB028352
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol
Description2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol (DMQH2) is an intermediate in coenzyme Q biosynthesis. It is produced by gut microbes. In microbes, the starting compound, 4-hydroxybenzoate, undergoes a prenylation, a decarboxylation and three hydroxylations alternating with three methylation reactions, resulting in the formation of coenzyme Q. In the final step, DMQH2 is converted from 2-octaprenyl-6-methoxy-1,4-benzoquinol (DDMQH2) with the help of Methyltransferase. Coenzyme Q (ubiquinone or Q)1 is a redox active lipid containing a long polyprenyl tail attached to a fully substituted benzoquinone ring. The number (n) of isoprene units in the polyprenyl tail (Qn) is distinct in different organisms; humans produce Q10, Caenorhabditis elegans Q9, Escherichia coli Q8, and Saccharomyces cerevisiae Q6. [HMDB]
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.00056 g/LALOGPS
logP7.59ALOGPS
logP9.24ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)13.24ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity185.98 m³·mol⁻¹ChemAxon
Polarizability72.38 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC38H60O3
IUPAC name3-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-5-methoxy-2-methylcyclohexa-2,5-diene-1,4-diol
InChI IdentifierInChI=1S/C38H60O3/c1-28(2)15-10-16-29(3)17-11-18-30(4)19-12-20-31(5)21-13-22-32(6)23-14-24-33(7)25-26-35-34(8)36(39)27-37(41-9)38(35)40/h15,17,19,21,23,25,27,36,38-40H,10-14,16,18,20,22,24,26H2,1-9H3/b29-17+,30-19+,31-21+,32-23+,33-25+
InChI KeyVFOCBGJJNKIBIS-NSUIJKAQSA-N
Isomeric SMILESCOC1=CC(O)C(C)=C(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
Average Molecular Weight564.8812
Monoisotopic Molecular Weight564.454245786
Classification
Description Belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesterterpenoids
Direct ParentSesterterpenoids
Alternative Parents
Substituents
  • Sesterterpenoid
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-3194870000-f376c877f913384df2d9Spectrum
Predicted GC-MS2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-4164649000-df8cfbdde889094079fbSpectrum
Predicted GC-MS2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol, "2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0211090000-a88d70d7fa08aba7f6872016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002e-0948130000-9f045c02a5cc0b076a8e2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6t-3579500000-7f6e268857370ad314db2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000090000-cafd6f4c9ab3e0f8609a2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-0000090000-4477ceedb68c42a6d4192016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-4200290000-e3037013dce1ef0a0c282016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-017j-3004690000-88f080ba1122d62df8e42021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9444810000-2b6eadda4f607a2c8c392021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-9401100000-868076aeb9c12c9dae2c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000090000-0ccc37397e5de7ce56a02021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03g1-0400290000-e41f70cbca1289278f582021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004r-3927840000-da5bbd2edb582bb72beb2021-09-24View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53481017
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB11661
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
Processing...
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