ubiquinol (YMDB00902)

Identification
YMDB IDYMDB00902
Nameubiquinol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionUbiquinol 8 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. Ubiquinol 8 is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • coenzymes QH2
  • CoQH2
  • QH(2)
  • QH2
  • reduced ubiquinone
  • Ubiquinol
  • ubiquinol-8
  • ubiquinol(8)
  • ubiquinols
  • Reduced coenzyme Q8
CAS number56275-39-9
WeightAverage: 731.1412
Monoisotopic: 730.590010984
InChI KeyFLVUMORHBJZINO-SGHXUWJISA-N
InChIInChI=1S/C49H78O4/c1-36(2)20-13-21-37(3)22-14-23-38(4)24-15-25-39(5)26-16-27-40(6)28-17-29-41(7)30-18-31-42(8)32-19-33-43(9)34-35-45-44(10)46(50)48(52-11)49(53-12)47(45)51/h20,22,24,26,28,30,32,34,46-47,50-51H,13-19,21,23,25,27,29,31,33,35H2,1-12H3/b37-22+,38-24+,39-26+,40-28+,41-30+,42-32+,43-34+
IUPAC Name2,3-dimethoxy-5-methyl-6-[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-yl]benzene-1,4-diol
Traditional IUPAC Nameubiquinol-8
Chemical FormulaC49H78O4
SMILESCOC1=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)CCC=C(C)C)=C(C)C1O
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
  • Tetraterpenoid
  • 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
StateSolid
Charge0
Melting point45.6 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00027 g/LALOGPS
logP9.35ALOGPS
logP14.91ChemAxon
logS-6.4ALOGPS
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 Count25ChemAxon
Refractivity238.85 m³·mol⁻¹ChemAxon
Polarizability94.28 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Citric Acid CyclePW000952 ThumbThumb?image type=greyscaleThumb?image type=simple
Citric Acid Cycle 1434561204PW000970 ThumbThumb?image type=greyscaleThumb?image type=simple
Oxidative phosphorylationPW002461 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA CyclePW002377 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Oxidative phosphorylationec00190 Map00190
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0323324900-8d5262afd36dcbc7148aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0032-1648692100-f4b35e5836e1b0685dbeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0532-5487958100-34e9af02e9a7005e70a4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000900-456744203daa0fca5d76JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0h00-0000009500-add178adb113c4e8faa3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03k9-3000019100-471dfb54d9e8cb8939f8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-057j-6405569600-34b9f4abc22e1814c315JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-4904532000-2ec1e0341ea818671a91JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0036-9613310000-3825f8084c00c72645ecJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000900-753eb68b8e8835d49d63JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00mk-0910108500-1324247480f23e6031eaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0942167000-3f62ea4336556f2f28ceJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Swida-Barteczka, A., Woyda-Ploszczyca, A., Sluse, F. E., Jarmuszkiewicz, W. (2009). "Uncoupling protein 1 inhibition by purine nucleotides is under the control of the endogenous ubiquinone redox state." Biochem J 424:297-306.19747168
  • Schultz, J. R., Ellerby, L. M., Gralla, E. B., Valentine, J. S., Clarke, C. F. (1996). "Autoxidation of ubiquinol-6 is independent of superoxide dismutase." Biochemistry 35:6595-6603.8639607
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17976
HMDB IDHMDB01060
Pubchem Compound ID1154
Kegg IDC00390
ChemSpider ID17216048
FOODB IDFDB022399
WikipediaUbiquinol
BioCyc IDUBIQUINOL-8

Enzymes

Protein Details
1. Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial
General function:
Involved in electron carrier activity
Specific function:
Catalytic subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q). SDH1 and SDH2 form the catalytic dimer. Electrons flow from succinate to the FAD bound to SDH1, and sequentially through the iron-sulfur clusters bound to SDH2 and enter the membrane dimer formed by SDH3 and SDH4
Gene Name:
SDH1
Uniprot ID:
Q00711
Molecular weight:
70228.79688
Reactions
Succinate + ubiquinone → fumarate + ubiquinol.
Protein Details
2. Succinate dehydrogenase [ubiquinone] flavoprotein subunit 2, mitochondrial
General function:
Involved in electron carrier activity
Specific function:
Probable minor catalytic subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q). Probably forms a catalytic dimer with SDH2. Electrons flow from succinate to the FAD bound to the catalytic subunit, and sequentially through the iron-sulfur clusters bound to SDH2 and enter the membrane dimer formed by SDH3 and SDH4
Gene Name:
Not Available
Uniprot ID:
P47052
Molecular weight:
69382.0
Reactions
Succinate + ubiquinone → fumarate + ubiquinol.
Protein Details
3. Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial
General function:
Involved in 2 iron, 2 sulfur cluster binding
Specific function:
Subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q). SDH1 and SDH2 form the catalytic dimer. Electrons flow from succinate to the FAD bound to SDH1, and sequentially through the iron-sulfur clusters bound to SDH2 and enter the membrane dimer formed by SDH3 and SDH4
Gene Name:
SDH2
Uniprot ID:
P21801
Molecular weight:
30230.90039
Reactions
Succinate + ubiquinone → fumarate + ubiquinol.
Protein Details
4. Cytochrome b-c1 complex subunit Rieske, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Component of the ubiquinol-cytochrome c reductase complex (complex III or cytochrome b-c1 complex), which is part of the mitochondrial respiratory chain that generates an electrochemical potential coupled to ATP synthesis. The complex couples electron transfer from ubiquinol to cytochrome c
Gene Name:
RIP1
Uniprot ID:
P08067
Molecular weight:
23364.69922
Reactions
QH(2) + 2 ferricytochrome c → Q + 2 ferrocytochrome c + 2 H(+).