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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:20:01 UTC
Update Date2017-10-23 19:06:08 UTC
HMDB IDHMDB0013111
Secondary Accession Numbers
  • HMDB13111
Metabolite Identification
Common NameUbiquinol-10
DescriptionUbiquinol-10 is a benzoquinol and is the reduced product of ubiquinone also called coenzyme Q10.The reduction of ubiquinone to ubiquinol occurs in Complexes I&II in the electron transfer chain. The Q cycle is a process that occurs in cytochrome b[, a component of Complex III in the electron transport chain,and that converts ubiquinol to ubiquinone in a cyclic fashion. When ubiquinol binds to cytochrome b, the pKa of the phenolic group decreases so that the proton ionizes and the phenoxide anion is formed (Wikipedia). Ubiquinol-10, the reduced form of ubiquinone-10, efficiently scavenges free radicals generated chemically within liposomal membranes. Ubiquinol-10 is about as effective in preventing peroxidative damage to lipids as alpha-tocopherol, which is considered the best lipid-soluble antioxidant in humans. The number of radicals scavenged by each molecule of ubiquinol-10 is 1.1 under certain experimental conditions. In contrast to alpha-tocopherol, ubiquinol-10 is not recycled by ascorbate. However, it is known that ubiquinol-10 can be recycled by electron transport carriers present in various biomembranes and possibly by some enzymes. It is shown that ubiquinol-10 spares alpha-tocopherol when both antioxidants are present in the same liposomal membranes and that ubiquinol-10, like alpha-tocopherol, does not interact with reduced glutathione.It is suggested that ubiquinol-10 is an important physiological lipid-soluble antioxidant. [PMID: 2352956 ].
Structure
Thumb
Synonyms
ValueSource
Coenzyme Q10-H2ChEBI
CoQ10h2ChEBI
Reduced coenzyme Q10ChEBI
Ubiquinol(10)ChEBI
CoQ(,10)H(,2)HMDB
CoQH(,2)HMDB
Coenzyme Q10, reducedMeSH
Chemical FormulaC59H92O4
Average Molecular Weight865.3594
Monoisotopic Molecular Weight864.699561432
IUPAC Name2-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-5,6-dimethoxy-3-methylbenzene-1,4-diol
Traditional Nameubiquinol(10)
CAS Registry Number5677-55-4
SMILES
COC1=C(OC)C(O)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(C)=C1O
InChI Identifier
InChI=1S/C59H92O4/c1-44(2)24-15-25-45(3)26-16-27-46(4)28-17-29-47(5)30-18-31-48(6)32-19-33-49(7)34-20-35-50(8)36-21-37-51(9)38-22-39-52(10)40-23-41-53(11)42-43-55-54(12)56(60)58(62-13)59(63-14)57(55)61/h24,26,28,30,32,34,36,38,40,42,60-61H,15-23,25,27,29,31,33,35,37,39,41,43H2,1-14H3/b45-26+,46-28+,47-30+,48-32+,49-34+,50-36+,51-38+,52-40+,53-42+
InChI KeyQNTNKSLOFHEFPK-UPTCCGCDSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as polyprenyl quinols. These are compounds containing a polyisoprene chain attached to a quinol(hydroquinone) at the second ring position.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassPrenol lipids
Direct ParentPolyprenyl quinols
Alternative Parents
Substituents
  • Polyterpenoid
  • Tetraterpenoid
  • 2-polyprenyl-6-methoxyphenol
  • Polyprenylbenzoquinol
  • Polyprenylphenol
  • 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

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

Source:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

Role

Industrial application:

  Pharmaceutical industry:

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 Solubility0.00023 g/LALOGPS
logP9.68ALOGPS
logP18.23ChemAxon
logS-6.6ALOGPS
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 Count31ChemAxon
Refractivity286.45 m³·mol⁻¹ChemAxon
Polarizability112.46 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0212122090-5e306e2cf0f1f2a759a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016s-0958587200-fef2b628971a8a4a77b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-1555659310-8eeeca49aeaf08faf8feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-f5379c25b8f0dc4902cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03ds-1000000690-b45be3825182ab04e016View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006t-9100000770-b1fa0941ae35b7012e61View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB029288
KNApSAcK IDNot Available
Chemspider ID8138335
KEGG Compound IDNot Available
BioCyc IDCPD-9958
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9962735
PDB IDNot Available
ChEBI ID64183
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Frei B, Kim MC, Ames BN: Ubiquinol-10 is an effective lipid-soluble antioxidant at physiological concentrations. Proc Natl Acad Sci U S A. 1990 Jun;87(12):4879-83. [PubMed:2352956 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.