Common NameUbiquinol-8
DescriptionUbiquinol 8 is a ubiquinol in which the polyprenyl substituent is octaprenyl. Ubiquinol-8 is the reduced form of ubiquinone-8. Ubiquinone (also known as coenzyme Q) is an isoprenoid quinone that functions as an electron carrier in membranes. In eukaryotes, ubiquinone is found mostly within the inner mitochondrial membrane where it functions in respiratory electron transport, transferring two electrons from either complex I (NADH dehydrogenase) or complex II (succinate-ubiquinone reductase) to complex III (bc1 complex). The quinone nucleus of ubiquinone is derived directly from 4-hydroxybenzoate, while the isoprenoid subunits of the polyisoprenoid tail are synthesized via the methylerythritol phosphate pathway, which feeds isoprene units into the polyprenyl biosynthesis pathways. The number of isoprenoid subunits in the ubiquinone side chain varies in different species. For example, Saccharomyces cerevisiae has 6 such subunits, Escherichia coli K-12 has 8, rat and mouse have 9, and Homo sapiens has 10. Ubiquinol-8 is effective as an anti-oxidant. By donating one of its hydrogen atoms to become the free-radical semiquinone (.Q-), it can neutralize a lipid peroxyl radical. The free-radical semiquinone is then restored to a non-free-radical state by the respiratory chain Q cycle. Ubiquinol or the free-radical semiquinone can also regenerate the Vitamin E tocopheroxyl radical by electron donation (http://www.benbest.com/nutrceut/CoEnzymeQ.html).
Structure
Molecular FormulaC49H76O4
Average Mass729.12530
Monoisotopic Mass728.57436
IUPAC Name2,3-dimethoxy-5-methyl-6-[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-yl]benzene-1,4-diol
Traditional NameUbiquinol-8
CAS Registry Number74075-00-6
SMILESCOc1c(O)c(C)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)CCC=C(C)C)c(O)c1OC
InChI IdentifierInChI=1S/C49H76O4/c1-36(2)20-13-21-37(3)22-14-23-38(4)24-15-25-39(5)26-16-27-40(6)28-17-29-41(7)30-18-31-42(8)32-19-33-43(9)34-35-45-44(10)46(50)48(52-11)49(53-12)47(45)51/h20,22,24,26,28,30,32,34,50-51H,13-19,21,23,25,27,29,31,33,35H2,1-12H3/b37-22+,38-24+,39-26+,40-28+,41-30+,42-32+,43-34+
InChI KeyLOJUQFSPYHMHEO-SGHXUWJISA-N
CHEBI IDCHEBI:61682
HMDB IDHMDB0001060
Pathways
NameSMPDB/PathBank
Oxidative phosphorylation
StateSolid
Water Solubility3.45e-04 g/l
logP8.66
logS-6.33
pKa (Strongest Acidic)12.91
pKa (Strongest Basic)-3.58
Hydrogen Acceptor Count4
Hydrogen Donor Count2
Polar Surface Area58.92 Ų
Rotatable Bond Count25
Physiological Charge0
Formal Charge0
Refractivity240.23 m³·mol⁻¹
Polarizability95.00

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