Np mrd loader

Record Information
Version2.0
Created at2024-09-11 20:14:49 UTC
Updated at2024-09-11 20:14:50 UTC
NP-MRD IDNP0339185
Secondary Accession NumbersNone
Natural Product Identification
Common NameUbiquinol-10
DescriptionUbiquinol-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).
Structure
Thumb
Synonyms
ValueSource
Coenzyme Q10-H2ChEBI
CoQ10h2ChEBI
Reduced coenzyme Q10ChEBI
Ubiquinol(10)ChEBI
CoQ(,10)H(,2)HMDB
CoQH(,2)HMDB
Coenzyme Q10, reducedHMDB
Ubiquinone hydroquinoneMeSH
Ubiquinol 1MeSH
Ubiquinol 7MeSH
Ubiquinol 50MeSH
UbiquinolsMeSH
Ubiquinol 9MeSH
Ubiquinol 0MeSH
Ubiquinol 6 (ubiquinol 30)MeSH
Chemical FormulaC59H92O4
Average Mass865.3594 Da
Monoisotopic Mass864.69956 Da
IUPAC Name2-[(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
Traditional Nameubiquinol(10)
CAS Registry NumberNot Available
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
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+
InChI KeyQNTNKSLOFHEFPK-UPTCCGCDSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentPolyprenyl quinols
Alternative Parents
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
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP9.68ALOGPS
logP18.23ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)10.27ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 ŲChemAxon
Rotatable Bond Count31ChemAxon
Refractivity286.45 m³·mol⁻¹ChemAxon
Polarizability112.46 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0013111
DrugBank IDDB11340
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029288
KNApSAcK IDNot Available
Chemspider ID8138335
KEGG Compound IDNot Available
BioCyc IDCPD-9958
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9962735
PDB IDNot Available
ChEBI ID64183
Good Scents IDNot Available
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]