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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:22:34 UTC
Update Date2019-01-11 19:31:14 UTC
HMDB IDHMDB0012299
Secondary Accession Numbers
  • HMDB12299
Metabolite Identification
Common NameUbiquinol-6
DescriptionUbUbiquinone(Q) is an essential, lipid soluble, redox component of the mitochondrial respiratory chain. Much evidence suggests that ubiquinol (QH2) functions as an effective antioxidant in a number of membrane and biological systems by preventing peroxidative damage to lipids. It has been proposed that superoxide dismutase (SOD) may protect QH2 from autoxidation by acting either directly as a superoxide−semiquinone oxidoreductase or indirectly by scavenging superoxide. (Biochemistry, 1996, 35 (21), pp 6595 - 6603).
Structure
Data?1547235074
Synonyms
ValueSource
DihydroubiquinoneHMDB
Reduced ubiquinoneHMDB
UbiquinolHMDB
Ubiquinol(30)HMDB
Chemical FormulaC39H60O4
Average Molecular Weight592.8913
Monoisotopic Molecular Weight592.449160408
IUPAC Name2-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-5,6-dimethoxy-3-methylbenzene-1,4-diol
Traditional Nameubiquinol-6
CAS Registry Number5677-58-7
SMILES
COC1=C(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)C(O)=C1OC
InChI Identifier
InChI=1S/C39H60O4/c1-28(2)16-11-17-29(3)18-12-19-30(4)20-13-21-31(5)22-14-23-32(6)24-15-25-33(7)26-27-35-34(8)36(40)38(42-9)39(43-10)37(35)41/h16,18,20,22,24,26,40-41H,11-15,17,19,21,23,25,27H2,1-10H3/b29-18+,30-20+,31-22+,32-24+,33-26+
InChI KeyDYOSCPIQEYRQEO-LPHQIWJTSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 2-polyprenyl-6-methoxyphenols. These 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
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • Anisole
  • Hydroquinone
  • M-cresol
  • Phenoxy compound
  • O-cresol
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • Phenol
  • Toluene
  • Monocyclic benzene moiety
  • Benzenoid
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00035 g/LALOGPS
logP8.49ALOGPS
logP11.59ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)10.27ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity191.24 m³·mol⁻¹ChemAxon
Polarizability75.45 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05dr-2168390000-394910f888dc5f30f46dJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-3128379000-0117b81715e9c07a4c03JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0223190000-d20ae1eccfe0bb20cd4cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0669330000-51dfe9ccd5bc50aa4b9dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fr2-2159340000-bc6056287dbe529b04e3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000090000-bdbe9cf3cbc85ce127e4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kf-0000190000-15019b0edbf51d3e63b8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fr-9200450000-c956803409da86b9394aJSpectraViewer | MoNA
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
FoodDB IDFDB028922
KNApSAcK IDNot Available
Chemspider ID4710167
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5813154
PDB IDNot Available
ChEBI ID52970
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.