Ubiquinol-10 (BioCAD00000025559)

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Metabolite Card

Formula: C59H92O4 (864.6995)
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

Synonyms [en]

Ubiquinol-10; Ubiquinol(10); Ubiquinol; CoQ10H2; coenzyme Q10-H2; reduced coenzyme Q10

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Ubiquinol-10. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000025559). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Ubiquinol-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].

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 5677-55-4
  • CAS Registry Number: 992-78-9
  • PubChem: 9962735
  • ChEBI: ChEBI:64183
  • HMDB: HMDB0013111
  • BioCyc: CPD-9958
  • NCBI MeSH: ubiquinol
  • Wikipedia: Ubiquinol
  • DrugBank: DB11340
  • RefMet: RM0118478
  • Coconut NaturalProduct: CNP0224337.0

Class / Ontology

Metabolic Network
ID EC Number Name
Rhea:RHEA:38360 ubiquinone-10 + hydrogen sulfide + sulfite + 2 H+ => ubiquinol-10 + thiosulfate
Rhea:RHEA:38361 ubiquinol-10 + thiosulfate => ubiquinone-10 + hydrogen sulfide + sulfite + 2 H+
Rhea:RHEA:38362 ubiquinone-10 + hydrogen sulfide + sulfite + 2 H+ <=> ubiquinol-10 + thiosulfate
Rhea:RHEA:44413 2.1.1.64 3-demethylubiquinol-10 + S-adenosyl-L-methionine => ubiquinol-10 + S-adenosyl-L-homocysteine + H+
Rhea:RHEA:44414 2.1.1.64 ubiquinol-10 + S-adenosyl-L-homocysteine + H+ => 3-demethylubiquinol-10 + S-adenosyl-L-methionine
Rhea:RHEA:44415 2.1.1.64 3-demethylubiquinol-10 + S-adenosyl-L-methionine <=> ubiquinol-10 + S-adenosyl-L-homocysteine + H+
Rhea:RHEA:52517 ubiquinone-10 + trans-4-hydroxy-L-proline => (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + ubiquinol-10 + H+
Rhea:RHEA:52518 (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + ubiquinol-10 + H+ => ubiquinone-10 + trans-4-hydroxy-L-proline
Rhea:RHEA:52519 ubiquinone-10 + trans-4-hydroxy-L-proline <=> (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + ubiquinol-10 + H+
Rhea:RHEA:61981 ubiquinone-10 + NADPH + H+ => ubiquinol-10 + NADP+
Rhea:RHEA:61982 ubiquinol-10 + NADP+ => ubiquinone-10 + NADPH + H+
Rhea:RHEA:61983 ubiquinone-10 + NADPH + H+ <=> ubiquinol-10 + NADP+
Rhea:RHEA:61985 ubiquinone-10 + NADH + H+ => ubiquinol-10 + NAD+
Rhea:RHEA:61986 ubiquinol-10 + NAD+ => ubiquinone-10 + NADH + H+
Rhea:RHEA:61987 ubiquinone-10 + NADH + H+ <=> ubiquinol-10 + NAD+
Rhea:RHEA:62609 ubiquinone-10 + hydrogen sulfide + glutathione + H+ => S-sulfanylglutathione + ubiquinol-10
Rhea:RHEA:62610 S-sulfanylglutathione + ubiquinol-10 => ubiquinone-10 + hydrogen sulfide + glutathione + H+
Rhea:RHEA:62611 ubiquinone-10 + hydrogen sulfide + glutathione + H+ <=> S-sulfanylglutathione + ubiquinol-10
BioCyc:RXN-9237 2.1.1.64 S-ADENOSYLMETHIONINE + CPD-9873 --> PROTON + CPD-9958 + ADENOSYL-HOMO-CYS
BioCyc:RXN-9348 CPD-9958 + Acceptor<=>UBIQUINONE-10 + Donor-H2
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Organism Source

Taxonomy Source

Pathway Synthetic

pathway id name
BioCyc:HUMAN_PWY-5872 ubiquinol-10 biosynthesis
BioCyc:META_PWY-5872 ubiquinol-10 biosynthesis (eukaryotic)
BioCyc:META_PWY-5857 ubiquinol-10 biosynthesis (prokaryotic)
BioCyc:SCO_ANARESPACC-PWY respiration (anaerobic)-- electron acceptors reaction list
PathBank:SMP0001026 TCA cycle (ubiquinol-10)
PlantCyc:BREADWHEAT_PWY-5686 UMP biosynthesis I
PlantCyc:BREADWHEAT_PWY-7211 superpathway of pyrimidine deoxyribonucleotides de novo biosynthesis
PlantCyc:CVARIABILIS_PWY-5872 ubiquinol-10 biosynthesis (late decarboxylation)
PlantCyc:CHLAMY_PWY-5872 ubiquinol-10 biosynthesis (late decarboxylation)
PlantCyc:PLANT_PWY-5386 methylglyoxal degradation I
PlantCyc:PLANT_PWY-3781 aerobic respiration I (cytochrome c)
PlantCyc:AHALLERI_PWY-5872 ubiquinol-10 biosynthesis (late decarboxylation)
PlantCyc:AHYPOCHONDRIACUS_PWY-5872 ubiquinol-10 biosynthesis (late decarboxylation)
PlantCyc:ALYRATA_PWY-5872 ubiquinol-10 biosynthesis (late decarboxylation)
PlantCyc:ZMARINA_PWY-4302 aerobic respiration III (alternative oxidase pathway)
PlantCyc:BREADWHEAT_PWY-6118 glycerol-3-phosphate shuttle
PlantCyc:BREADWHEAT_PWY-4261 glycerol degradation I
PlantCyc:BREADWHEAT_PWY-6475 trans-lycopene biosynthesis II (oxygenic phototrophs and green sulfur bacteria)
PlantCyc:SPIRODELA_PWY-5872 ubiquinol-10 biosynthesis (eukaryotic)
PlantCyc:CORN_PWY-5872 ubiquinol-10 biosynthesis (late decarboxylation)
View All Pathways