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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-02-03 11:20:53 UTC
Update Date2022-03-07 02:51:12 UTC
HMDB IDHMDB0011661
Secondary Accession Numbers
  • HMDB11661
Metabolite Identification
Common 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) 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.
Structure
Data?1582752935
Synonyms
ValueSource
2-Polyprenyl-3-methyl-6-methoxy-1,4-benzoquinolHMDB
5-DemethoxyubiquinolHMDB
DMQH2HMDB
Chemical FormulaC38H60O3
Average Molecular Weight564.8812
Monoisotopic Molecular Weight564.454245786
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
Traditional 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
CAS Registry NumberNot Available
SMILES
COC1=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
InChI Identifier
InChI=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
Chemical Taxonomy
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

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+234.53231661259
DarkChem[M-H]-228.91731661259
DeepCCS[M+H]+247.97530932474
DeepCCS[M-H]-245.57930932474
DeepCCS[M-2H]-278.50230932474
DeepCCS[M+Na]+253.88830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinolCOC1=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)C1O4532.0Standard polar33892256
2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinolCOC1=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)C1O3793.9Standard non polar33892256
2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinolCOC1=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)C1O4048.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol,1TMS,isomer #1COC1=CC(O[Si](C)(C)C)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)C1O3941.4Semi standard non polar33892256
2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol,1TMS,isomer #2COC1=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[Si](C)(C)C3920.0Semi standard non polar33892256
2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol,2TMS,isomer #1COC1=CC(O[Si](C)(C)C)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[Si](C)(C)C3897.5Semi standard non polar33892256
2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol,1TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)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)C1O4159.8Semi standard non polar33892256
2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol,1TBDMS,isomer #2COC1=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[Si](C)(C)C(C)(C)C4133.5Semi standard non polar33892256
2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol,2TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)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[Si](C)(C)C(C)(C)C4321.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-3194870000-f376c877f913384df2d92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol GC-MS (1 TMS) - 70eV, Positivesplash10-00di-4164649000-df8cfbdde889094079fb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol GC-MS ("2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol 10V, Positive-QTOFsplash10-00kb-0211090000-a88d70d7fa08aba7f6872016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol 20V, Positive-QTOFsplash10-002e-0948130000-9f045c02a5cc0b076a8e2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol 40V, Positive-QTOFsplash10-0f6t-3579500000-7f6e268857370ad314db2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol 10V, Negative-QTOFsplash10-03di-0000090000-cafd6f4c9ab3e0f8609a2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol 20V, Negative-QTOFsplash10-03dj-0000090000-4477ceedb68c42a6d4192016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol 40V, Negative-QTOFsplash10-000t-4200290000-e3037013dce1ef0a0c282016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol 10V, Positive-QTOFsplash10-017j-3004690000-88f080ba1122d62df8e42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol 20V, Positive-QTOFsplash10-001i-9444810000-2b6eadda4f607a2c8c392021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol 40V, Positive-QTOFsplash10-000x-9401100000-868076aeb9c12c9dae2c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol 10V, Negative-QTOFsplash10-03di-0000090000-0ccc37397e5de7ce56a02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol 20V, Negative-QTOFsplash10-03g1-0400290000-e41f70cbca1289278f582021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol 40V, Negative-QTOFsplash10-004r-3927840000-da5bbd2edb582bb72beb2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028352
KNApSAcK IDNot Available
Chemspider ID35032083
KEGG Compound IDNot Available
BioCyc IDCPD-9871
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481017
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.