Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-18 01:45:37 UTC
Update Date2022-08-31 18:23:48 UTC
Metabolite IDMMDBc0031718
Metabolite Identification
Common NameUbiquinone-3
DescriptionUbiquinone-3 is a member of the chemical class known as Polyprenylbenzoquinones. These are compounds containing a polyisoprene chain attached to a quinone at the second ring position. Ubiquione-1 has just 3 isoprene units. Normally in E. coli the active form of Ubiquinone has 8 isoprene units (Ubiquinone-8) and in humans it normally has 10. Ubiquinone-3 is a “failed” or incomplete version of Ubiquinone 8 that arises from conjugation by a shortened prenyl tail via 4-hydroxybenzoate polyprenyltransferase. Ubiquionone is involved in cellular respiration. It is fat-soluble and is therefore mobile in cellular membranes; it plays 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
Synonyms
ValueSource
Coenzyme Q3MeSH
CoQ3MeSH
Ubiquinone Q3MeSH
Molecular FormulaC24H34O4
Average Mass386.5244
Monoisotopic Mass386.245709576
IUPAC Name2,3-dimethoxy-5-methyl-6-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]cyclohexa-2,5-diene-1,4-dione
Traditional Name2,3-dimethoxy-5-methyl-6-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]cyclohexa-2,5-diene-1,4-dione
CAS Registry NumberNot Available
SMILES
COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O
InChI Identifier
InChI=1S/C24H34O4/c1-16(2)10-8-11-17(3)12-9-13-18(4)14-15-20-19(5)21(25)23(27-6)24(28-7)22(20)26/h10,12,14H,8-9,11,13,15H2,1-7H3/b17-12+,18-14+
InChI KeyXREILSQAXUAAHP-NXGXIAAHSA-N