Ubiquinone-10 (BioCAD00000019036)

blood feces brain kidney leukocyte liver skeletal muscle

Metabolite Card

Formula: C59H90O4 (862.6839)
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)C1=O

Synonyms [en]

coenzyme Q10; ubiquinone-10; ubidecarenone; CoQ10; Adelir; Q10

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Ubiquinone-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: BioCAD00000019036). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Coenzyme Q10 (ubiquinone) is a naturally occurring compound widely distributed in animal organisms and in humans. The primary compounds involved in the biosynthesis of ubiquinone are 4-hydroxybenzoate and the polyprenyl chain. An essential role of coenzyme Q10 is as an electron carrier in the mitochondrial respiratory chain. Moreover, coenzyme Q10 is one of the most important lipophilic antioxidants, preventing the generation of free radicals as well as oxidative modifications of proteins, lipids, and DNA, it and can also regenerate the other powerful lipophilic antioxidant, alpha-tocopherol. Antioxidant action is a property of the reduced form of coenzyme Q10, ubiquinol (CoQ10H2), and the ubisemiquinone radical (CoQ10H*). Paradoxically, independently of the known antioxidant properties of coenzyme Q10, the ubisemiquinone radical anion (CoQ10-) possesses prooxidative properties. Decreased levels of coenzyme Q10 in humans are observed in many pathologies (e.g. cardiac disorders, neurodegenerative diseases, AIDS, cancer) associated with intensive generation of free radicals and their action on cells and tissues. In these cases, treatment involves pharmaceutical supplementation or increased consumption of coenzyme Q10 with meals as well as treatment with suitable chemical compounds (i.e. folic acid or B-group vitamins) which significantly increase ubiquinone biosynthesis in the organism. Estimation of coenzyme Q10 deficiency and efficiency of its supplementation requires a determination of ubiquinone levels in the organism. Therefore, highly selective and sensitive methods must be applied, such as HPLC with UV or coulometric detection. For a number of years, coenzyme Q (CoQ10 in humans) was known for its key role in mitochondrial bioenergetics; later studies demonstrated its presence in other subcellular fractions and in plasma, and extensively investigated its antioxidant role. These two functions constitute the basis on which research supporting the clinical use of CoQ10 is founded. Also at the inner mitochondrial membrane level, coenzyme Q is recognized as an obligatory co-factor for the function of uncoupling proteins and a modulator of the transition pore. Furthermore, recent data reveal that CoQ10 affects expression of genes involved in human cell signalling, metabolism, and transport and some of the effects of exogenously administered CoQ10 may be due to this property. Coenzyme Q is the only lipid soluble antioxidant synthesized endogenously. In its reduced form, CoQH2, ubiquinol, inhibits protein and DNA oxidation but it is the effect on lipid peroxidation that has been most deeply studied. Ubiquinol inhibits the peroxidation of cell membrane lipids and also that of lipoprotein lipids present in the circulation. Dietary supplementation with CoQ10 results in increased levels of ubiquinol-10 within circulating lipoproteins and increased resistance of human low-density lipoproteins to the initiation of lipid peroxidation. Moreover, CoQ10 has a direct anti-atherogenic effect, which has been demonstrated in apolipoprotein E-deficient mice fed with a high-fat diet. (PMID: 15928598, 17914161).

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 303-98-0
  • CAS Registry Number: 4916-59-0
  • PubChem: 5281915
  • PubChem: 5926222
  • ChEBI: ChEBI:46245
  • HMDB: HMDB0001072
  • LipidMaps: LMPR02010001
  • KEGG: C11378
  • BioCyc: UBIQUINONE-10
  • NCBI MeSH: coenzyme Q10
  • Wikipedia: Coenzyme_Q10
  • DrugBank: DB09270
  • RefMet: RM0138857
  • MoNA: CA000184
  • MoNA: LipidBlast2022_134185
  • MoNA: VF-NPL-QEHF026944
  • MoNA: VF-NPL-QEHF026945
  • MoNA: VF-NPL-QEHF026946
  • MoNA: VF-NPL-QEHF026947
  • MoNA: VF-NPL-QEHF026948
  • MoNA: VF-NPL-QEHF026949
  • MoNA: VF-NPL-QEHF026950
  • MoNA: VF-NPL-QEHF026951
  • MoNA: VF-NPL-QEHF026952
  • MoNA: VF-NPL-QEHF026953
  • MoNA: VF-NPL-QEHF026954
  • MoNA: VF-NPL-QEHF026955
  • MoNA: VF-NPL-QEHF026956
  • MoNA: VF-NPL-QEHF026957
  • MoNA: VF-NPL-QEHF026958
  • Metlin: METLIN_227

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: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-9354 UBIQUINONE-10 + AMMONIUM + WATER --> CPD-9613 + CARBON-DIOXIDE
BioCyc:RXN-9348 CPD-9958 + Acceptor<=>UBIQUINONE-10 + Donor-H2
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Organism Source

Taxonomy Source

Pathway Synthetic

pathway id name
BioCyc:PCHR_PWY-5872 ubiquinone-10 biosynthesis (eukaryotic)
BioCyc:CAULONA1000_PWY-5857 ubiquinone-10 biosynthesis (prokaryotic)
BioCyc:META_PWY-5888 rhodoquinone-10 biosynthesis
BioCyc:SCO_ANARESPACC-PWY respiration (anaerobic)-- electron acceptors reaction list
Plant Reactome:R-OGU-1119533 TCA cycle (plant)
Plant Reactome:R-CCA-1119533 TCA cycle (plant)
Plant Reactome:R-JCU-1119533 TCA cycle (plant)
Plant Reactome:R-VAN-1119533 TCA cycle (plant)
Plant Reactome:R-SLY-1119533 TCA cycle (plant)
Plant Reactome:R-OGR-1119533 TCA cycle (plant)
Plant Reactome:R-CAR-1119533 TCA cycle (plant)
Plant Reactome:R-TPR-1119533 TCA cycle (plant)
Plant Reactome:R-OSA-1119533 TCA cycle (plant)
Plant Reactome:R-OBR-1119533 TCA cycle (plant)
Plant Reactome:R-PHH-1119533 TCA cycle (plant)
Plant Reactome:R-OAU-1119533 TCA cycle (plant)
Plant Reactome:R-MES-1119533 TCA cycle (plant)
Plant Reactome:R-TDI-1119533 TCA cycle (plant)
Plant Reactome:R-PTI-1119533 TCA cycle (plant)
Plant Reactome:R-GMA-1119533 TCA cycle (plant)
View All Pathways