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Record Information
Version3.6
Creation Date2009-07-25 00:20:01 UTC
Update Date2013-05-29 19:48:40 UTC
HMDB IDHMDB13111
Secondary Accession NumbersNone
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
  1. CoQ(,10)H(,2)
  2. CoQ10H2
  3. CoQH(,2)
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 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
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
KingdomOrganic Compounds
Super ClassLipids
ClassPrenol Lipids
Sub ClassPolyterpenes
Other Descriptors
  • Aromatic Homomonocyclic Compounds
Substituents
  • Alkyl Aryl Ether
  • Anisole
  • Farnesane Skeleton
  • Hydroquinone
  • Hydroxyquinol Derivative
  • Isoprene
  • M Cresol
  • Methoxyphenol
  • O Cresol
  • Phenol
  • Phenol Derivative
  • Polyprenylbenzoquinol
  • Polyprenylphenol
  • Pyrogallol Derivative
  • Tetraterpene Backbone
  • Toluene
Direct ParentPolyterpenes
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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 Solubility0.000233ALOGPS
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 Å2ChemAxon
Rotatable Bond Count31ChemAxon
Refractivity286.45 m3·mol-1ChemAxon
Polarizability112.46 Å3ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
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-9873
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB13111
Metagene LinkHMDB13111
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