Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-18 01:45:28 UTC
Update Date2022-08-31 18:23:46 UTC
Metabolite IDMMDBc0031714
Metabolite Identification
Common NameUbiquinol-4
DescriptionUbiquinol-4 is a member of the chemical class known as Polyprenylbenzoquinols. They are reduced forms of polyprenylbenzoquinines (ubiquinones). These are compounds containing a polyisoprene chain attached to a quinol at the second ring position. Ubiquiol-4 has just 4 isoprene units. Normally in E. coli the active form of Ubiquinol has 8 isoprene units (Ubiquinol-8) and in humans it normally has 10. Ubiquinol-4 is a “failed” or incomplete version of Ubiquinol 8 that arises from conjugation by a shortened prenyl tail via 4-hydroxybenzoate polyprenyltransferase. Coenzyme Q(n) exists in three redox states, fully oxidized (ubiquinone), partially reduced (semiquinones or ubisemiquinones), and fully reduced (ubiquinols). The redox functions of ubiquinol in cellular energy production and antioxidant protection are based on the ability to exchange two electrons in a redox cycle between ubiquinol (reduced) and the ubiquinone (oxidized) form. Ubiquionols are important in cellular respiration. They are fat-soluble and therefore mobile in cellular membranes; they play a unique role in the electron transport chain (ETC). In the inner bacterial membrane, electrons from NADH and succinate pass through the ETC to the oxygen, which is then reduced to water. The transfer of electrons through ETC results in the pumping of H+ across the membrane creating a proton gradient across the membrane, which is used by ATP synthase (located on the membrane) to generate ATP.
Structure
SynonymsNot Available
Molecular FormulaC29H44O4
Average Mass456.6573
Monoisotopic Mass456.323959896
IUPAC Name2,3-dimethoxy-5-methyl-6-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzene-1,4-diol
Traditional Name2,3-dimethoxy-5-methyl-6-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzene-1,4-diol
CAS Registry NumberNot Available
SMILES
COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC
InChI Identifier
InChI=1S/C29H44O4/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-17-23(5)18-19-25-24(6)26(30)28(32-7)29(33-8)27(25)31/h12,14,16,18,30-31H,9-11,13,15,17,19H2,1-8H3/b21-14+,22-16+,23-18+
InChI KeyMNDMLSPMVVCPJU-INVBOZNNSA-N