Record Information |
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Version | 2.0 |
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Created at | 2024-09-11 20:14:49 UTC |
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Updated at | 2024-09-11 20:14:50 UTC |
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NP-MRD ID | NP0339185 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Ubiquinol-10 |
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Description | Ubiquinol-10, also known as coenzyme Q10-H2 or COQ10H2, belongs to the class of organic compounds known as polyprenyl quinols. Polyprenyl quinols are compounds containing a polyisoprene chain attached to a quinol(hydroquinone) at the second ring position. The reduction of ubiquinone to ubiquinol occurs in Complexes I&II in the electron transfer chain. Ubiquinol-10 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Ubiquinol-10 has been detected, but not quantified in, several different foods, such as sweet marjorams, jostaberries, common thymes, devilfish, and atlantic herrings. This could make ubiquinol-10 a potential biomarker for the consumption of these foods. There are varying concentrations of ubiquinol in foods, OTC products and dietary supplement products. Ubiquinol (CoQH2) is a reduced form of coenzyme Q10 (CoQ10) that acts as an active antioxidant that prevents the initiation and propagation of lipid peroxidation in biological membranes and human low-density lipoprotein (LDL). Ubiquinol-10 is a benzoquinol and is the reduced product of ubiquinone also called coenzyme Q10. It plays an essential role in maintaining cellular defense against oxidative damage and also sustains the effects of vitamin E by regenerating the vitamin from the tocopheroxyl radical, but ubiquinol is not classified as a vitamin because it is synthesized by humans. Ubiquinol-10 was first documented in 1999 (PMID: 10416034). The Q cycle is a process that occurs in cytochrome b (PMID: 10993485) (PMID: 11319712) (PMID: 15942122) (PMID: 17228924). |
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Structure | 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 InChI=1S/C59H92O4/c1-44(2)24-15-25-45(3)26-16-27-46(4)28-17-29-47(5)30-18-31-48(6)32-19-33-49(7)34-20-35-50(8)36-21-37-51(9)38-22-39-52(10)40-23-41-53(11)42-43-55-54(12)56(60)58(62-13)59(63-14)57(55)61/h24,26,28,30,32,34,36,38,40,42,60-61H,15-23,25,27,29,31,33,35,37,39,41,43H2,1-14H3/b45-26+,46-28+,47-30+,48-32+,49-34+,50-36+,51-38+,52-40+,53-42+ |
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Synonyms | Value | Source |
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Coenzyme Q10-H2 | ChEBI | CoQ10h2 | ChEBI | Reduced coenzyme Q10 | ChEBI | Ubiquinol(10) | ChEBI | CoQ(,10)H(,2) | HMDB | CoQH(,2) | HMDB | Coenzyme Q10, reduced | HMDB | Ubiquinone hydroquinone | MeSH | Ubiquinol 1 | MeSH | Ubiquinol 7 | MeSH | Ubiquinol 50 | MeSH | Ubiquinols | MeSH | Ubiquinol 9 | MeSH | Ubiquinol 0 | MeSH | Ubiquinol 6 (ubiquinol 30) | MeSH |
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Chemical Formula | C59H92O4 |
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Average Mass | 865.3594 Da |
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Monoisotopic Mass | 864.69956 Da |
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IUPAC Name | 2-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-5,6-dimethoxy-3-methylbenzene-1,4-diol |
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Traditional Name | ubiquinol(10) |
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CAS Registry Number | Not Available |
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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 |
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InChI Identifier | InChI=1S/C59H92O4/c1-44(2)24-15-25-45(3)26-16-27-46(4)28-17-29-47(5)30-18-31-48(6)32-19-33-49(7)34-20-35-50(8)36-21-37-51(9)38-22-39-52(10)40-23-41-53(11)42-43-55-54(12)56(60)58(62-13)59(63-14)57(55)61/h24,26,28,30,32,34,36,38,40,42,60-61H,15-23,25,27,29,31,33,35,37,39,41,43H2,1-14H3/b45-26+,46-28+,47-30+,48-32+,49-34+,50-36+,51-38+,52-40+,53-42+ |
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InChI Key | QNTNKSLOFHEFPK-UPTCCGCDSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | Not Available |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as polyprenyl quinols. Polyprenyl quinols are compounds containing a polyisoprene chain attached to a quinol(hydroquinone) at the second ring position. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Quinone and hydroquinone lipids |
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Direct Parent | Polyprenyl quinols |
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Alternative Parents | |
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Substituents | - Polyterpenoid
- 2-polyprenyl-6-methoxyphenol
- Polyprenylbenzoquinol
- Polyprenylphenol
- Ubiquinol skeleton
- Methoxyphenol
- O-dimethoxybenzene
- Dimethoxybenzene
- Anisole
- Hydroquinone
- M-cresol
- Phenoxy compound
- O-cresol
- Phenol ether
- Methoxybenzene
- Alkyl aryl ether
- Phenol
- Toluene
- Monocyclic benzene moiety
- Benzenoid
- Ether
- Organooxygen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Junqueira VB, Carrasquedo F, Azzalis LA, Giavarotti KA, Giavarotti L, Rodrigues L, Fraga CG, Boveris A, Videla LA: Content of liver and brain ubiquinol-9 and ubiquinol-10 after chronic ethanol intake in rats subjected to two levels of dietary alpha-tocopherol. Free Radic Res. 2000 Sep;33(3):313-9. doi: 10.1080/10715760000301481. [PubMed:10993485 ]
- Kontush A, Schippling S, Spranger T, Beisiegel U: Plasma ubiquinol-10 as a marker for disease: is the assay worthwhile? Biofactors. 1999;9(2-4):225-9. doi: 10.1002/biof.5520090217. [PubMed:10416034 ]
- Plat J, Mensink RP: Effects of diets enriched with two different plant stanol ester mixtures on plasma ubiquinol-10 and fat-soluble antioxidant concentrations. Metabolism. 2001 May;50(5):520-9. doi: 10.1053/meta.2001.22509. [PubMed:11319712 ]
- Mabuchi H, Higashikata T, Kawashiri M, Katsuda S, Mizuno M, Nohara A, Inazu A, Koizumi J, Kobayashi J: Reduction of serum ubiquinol-10 and ubiquinone-10 levels by atorvastatin in hypercholesterolemic patients. J Atheroscler Thromb. 2005;12(2):111-9. doi: 10.5551/jat.12.111. [PubMed:15942122 ]
- Mukai K, Tokunaga A, Itoh S, Kanesaki Y, Ohara K, Nagaoka S, Abe K: Structure-activity relationship of the free-radical-scavenging reaction by vitamin E (alpha-, beta-, gamma-, delta-Tocopherols) and ubiquinol-10: pH dependence of the reaction rates. J Phys Chem B. 2007 Jan 25;111(3):652-62. doi: 10.1021/jp0650580. [PubMed:17228924 ]
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