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Identification
YMDB IDYMDB00088
NameUbiquinone Q1
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionUbiquinone-1, also known as coenzyme Q1 or COQ1, belongs to the class of organic compounds known as ubiquinones. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methyl(1,4-benzoquinone) moiety to which an isoprenyl group is attached at ring position 2(or 6). Ubiquinone-1 is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
  • Coenzyme Q
  • Coenzyme Q1
  • Coenzyme Q5
  • Coenzymes Q
  • ubiquinone
  • Ubiquinone 1
  • Ubiquinone 5
  • Ubiquinone Q5
  • Ubiquinone-5
  • 2,3-Dimethoxy-5-methyl-6-(3-methyl-2-butenyl)-2,5-cyclohexadiene-1,4-dione
  • 2,3-Dimethoxy-5-methyl-6-(3-methylbut-2-en-1-yl)-1,4-benzoquinone
  • 2,3-Dimethoxy-5-methyl-6-(3-methylbut-2-enyl)benzo-1,4-quinone
  • CoQ1
  • Ubiquinone Q1
  • Ubiquinone-Q1
  • Ubiquionone 1
CAS number727-81-1
WeightAverage: 250.2903
Monoisotopic: 250.120509064
InChI KeySOECUQMRSRVZQQ-UHFFFAOYSA-N
InChIInChI=1S/C14H18O4/c1-8(2)6-7-10-9(3)11(15)13(17-4)14(18-5)12(10)16/h6H,7H2,1-5H3
IUPAC Name2,3-dimethoxy-5-methyl-6-(3-methylbut-2-en-1-yl)cyclohexa-2,5-diene-1,4-dione
Traditional IUPAC Nameubiquinone-1
Chemical FormulaC14H18O4
SMILES[H]C(=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])C1=C(C(=O)C(OC([H])([H])[H])=C(OC([H])([H])[H])C1=O)C([H])([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as ubiquinones. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methyl(1,4-benzoquinone) moiety to which an isoprenyl group is attached at ring position 2(or 6).
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentUbiquinones
Alternative Parents
Substituents
  • Ubiquinone skeleton
  • Monoterpenoid
  • Monocyclic monoterpenoid
  • Quinone
  • P-benzoquinone
  • Vinylogous ester
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.24 g/LALOGPS
logP2.2ALOGPS
logP2.22ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.38 m³·mol⁻¹ChemAxon
Polarizability26.94 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Mitochondrion
Organoleptic PropertiesNot Available
SMPDB Pathways
Oxidative phosphorylationPW002461 ThumbThumb?image type=greyscaleThumb?image type=simple
Proline MetabolismPW002365 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyrimidine metabolismPW002469 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Oxidative phosphorylationec00190 Map00190
Pyrimidine metabolismec00240 Map00240
Ubiquinone and other terpenoid-quinone biosynthesisec00130 Map00130
SMPDB Reactions
L-Proline + Ubiquinone Q1hydron + QH(2) + 1-Pyrroline-5-carboxylic acid
Succinic acid + Ubiquinone Q1QH(2) + Fumaric acid
4,5-Dihydroorotic acid + Ubiquinone Q1QH(2) + Orotic acid
QH(2) + oxygen + hydronUbiquinone Q1 + water + hydron
oxygen + QH(2) + hydronwater + hydron + Ubiquinone Q1
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ri-6690000000-54c21ecf74c316617005JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0190000000-e28dd9a4e1e31fde0aaaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0frt-4790000000-e9b4aa7330c158e93f74JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pw9-9400000000-984285464810c9d07a1aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0190000000-d560b9e909b6d771b748JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0890000000-173d3724196ddfd71b38JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001r-8940000000-6ddd0c7bdddc6aa7ff07JSpectraViewer
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
  • Cavazzoni, M., Svobodova, J., De Santis, A., Fato, R., Lenaz, G. (1993). "Steady-state kinetics of ubiquinol-cytochrome c reductase in Saccharomyces cerevisiae mitochondria: effects of fluidity changes obtained by different growth temperatures." Arch Biochem Biophys 303:246-254.8390217
Synthesis Reference:Naruta, Yoshinori; Maruyama, Kazuhiro. . Ubiquinone-1. Organic Syntheses (1993), 71 125-32.
External Links:
ResourceLink
CHEBI ID16389
HMDB IDHMDB02012
Pubchem Compound ID4462
Kegg IDC00399
ChemSpider ID4307
FOODB IDFDB022794
WikipediaUbiquinone
BioCyc IDNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
External NADH dehydrogenase required for optimum cellular growth with a number of nonfermentable carbon sources, including ethanol. With NDE1, performes the mitochondrial oxidation of cytosolic NADH under these growth conditions. Regulates the mitochondrial glycerol-3-phosphate dehydrogenase, GUT2, also involved in cytosolic NADH oxydation
Gene Name:
NDE2
Uniprot ID:
Q07500
Molecular weight:
61658.69922
Reactions
NADH + ubiquinone → NAD(+) + ubiquinol.
General function:
Involved in oxidoreductase activity
Specific function:
External NADH dehydrogenase required for optimum cellular growth with a number of nonfermentable carbon sources, including ethanol. With NDE2, performes the mitochondrial oxidation of cytosolic NADH under these growth conditions. Regulates the mitochondrial glycerol-3-phosphate dehydrogenase, GUT2, also involved in cytosolic NADH oxydation
Gene Name:
NDE1
Uniprot ID:
P40215
Molecular weight:
62773.60156
Reactions
NADH + ubiquinone → NAD(+) + ubiquinol.
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of NADH generated inside the Mitochondrion
Gene Name:
NDI1
Uniprot ID:
P32340
Molecular weight:
57249.30078
Reactions
NADH + ubiquinone → NAD(+) + ubiquinol.
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.
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.
General function:
Involved in iron-sulfur cluster binding
Specific function:
Accepts electrons from ETF and reduces ubiquinone
Gene Name:
Not Available
Uniprot ID:
Q08822
Molecular weight:
69633.39844
Reactions
Reduced electron-transferring flavoprotein + ubiquinone → electron-transferring flavoprotein + ubiquinol.
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.
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(+).