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
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].
DBLinks
- CAS Registry Number: 5677-55-4
- PubChem CID: 9962735
- ChEBI: 64183
- HMDB: HMDB0013111
- LipidMaps:
- KEGG:
- BioCyc: CPD-9958
- NCBI MeSH: ubiquinol
- Wikipedia: Ubiquinol
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
- WishartLab ClassyFire: [Quinone and hydroquinone lipids] Quinone and hydroquinone lipids
- RefMet: [Ubiquinones] Ubiquinones
- ChEBI: [CHEBI:64183] ubiquinol-10
- Coconut NaturalProduct: [Prenyl quinone meroterpenoids] Prenyl quinone meroterpenoids
| 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 |
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) |