Record Information
Version2.0
Creation Date2012-05-31 14:47:17 -0600
Update Date2015-06-03 17:20:05 -0600
Secondary Accession Numbers
  • ECMDB20487
Identification
Name:Ubiquinone-0
DescriptionUbiquinone-1 is a member of the chemical class known as Benzoquinones. Normally in E. coli the active form of Ubiquinone has 8 isoprene units (Ubiquinone-8) and in humans it normally has 10. Ubiquinone-10 is a naked version of Ubiquinone 8 that arises from conjugation by a shortened prenyl tail via 4-hydroxybenzoate polyprenyltransferase. Ubiquionone is involved in cellular respiration. It is fat-soluble and is therefore mobile in cellular membranes; it plays a unique role in the electron transport chain (ETC). In the inner bacterial membrane, electrons from NADH and succinate pass through the ETC to the oxygen, which is then reduced to water. The transfer of electrons through ETC results in the pumping of H+ across the membrane creating a proton gradient across the membrane, which is used by ATP synthase (located on the membrane) to generate ATP.
Structure
Thumb
Synonyms:
  • 2,3-Dimethoxy-5-methyl-1,4-benzoquinone
  • 2,3-Dimethoxy-5-methyl-2,5-Cyclohexadiene-1,4-dione
  • 2,3-Dimethoxy-5-methyl-p-benzoquinone
  • 2,3-Dimethoxy-5-methylbenzo-1,4-quinone
  • 2,3-Dimethoxy-5-methylbenzoquinone
  • 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione
  • 2,3-Dimethyoxyl-5-methyl-1,4-benzoquinone
  • 2-Methyl-4,5-dimethoxy-p-quinone
  • 2-Methyl-5,6-dimethoxybenzoquinone
  • Coenzyme q0
  • Coq0
  • D9150_SIGMA
  • Nchembio.62-comp10
  • Q0
  • Q0
  • Ubiquinone 0
  • Ubiquinone q0
  • Ubiquinone-O
  • Ubiquinone-Q0
  • Ubiquinone-Q0
Chemical Formula:C9H10O4
Weight:Average: 182.1733
Monoisotopic: 182.057908808
InChI Key:UIXPTCZPFCVOQF-UHFFFAOYSA-N
InChI:InChI=1S/C9H10O4/c1-5-4-6(10)8(12-2)9(13-3)7(5)11/h4H,1-3H3
CAS number:605-94-7
IUPAC Name:2,3-dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione
Traditional IUPAC Name:coenzyme Q0
SMILES:COC1=C(OC)C(=O)C(C)=CC1=O
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
  • 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
State:Solid
Charge:0
Melting point:59-60 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.37 g/LALOGPS
logP0.53ALOGPS
logP0.61ChemAxon
logS-1.5ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.82 m³·mol⁻¹ChemAxon
Polarizability17.64 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
TCA cycle (ubiquinol-0)PW002023 ThumbThumb?image type=greyscaleThumb?image type=simple
pyruvate to cytochrome bd terminal oxidase electron transferPW002087 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-2254c47ae8fb318c40d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1900000000-41fba48cebbe97a50219View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9100000000-01d5266ce1b46a31e76bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-9f847c697f47c86325cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-a9bb75a201179aa4a95aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-9300000000-15e8eb3a072ce7d451d0View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID27906
HMDB IDNot Available
Pubchem Compound ID69068
Kegg IDC05251
ChemSpider ID62289
Wikipedia IDNot Available
BioCyc IDCPD0-1464
EcoCyc IDCPD0-1464

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Pyruvate + ferricytochrome b1 + H(2)O = acetate + CO(2) + ferrocytochrome b1
Gene Name:
poxB
Uniprot ID:
P07003
Molecular weight:
62011
Reactions
Pyruvate + ubiquinone + H(2)O = acetate + CO(2) + ubiquinol.
General function:
Involved in electron carrier activity
Specific function:
Two distinct, membrane-bound, FAD-containing enzymes are responsible for the catalysis of fumarate and succinate interconversion; the fumarate reductase is used in anaerobic growth, and the succinate dehydrogenase is used in aerobic growth
Gene Name:
sdhB
Uniprot ID:
P07014
Molecular weight:
26770
Reactions
Succinate + acceptor = fumarate + reduced acceptor.
General function:
Involved in electron carrier activity
Specific function:
Two distinct, membrane-bound, FAD-containing enzymes are responsible for the catalysis of fumarate and succinate interconversion; the fumarate reductase is used in anaerobic growth, and the succinate dehydrogenase is used in aerobic growth
Gene Name:
sdhA
Uniprot ID:
P0AC41
Molecular weight:
64421
Reactions
Succinate + acceptor = fumarate + reduced acceptor.
General function:
Involved in succinate dehydrogenase activity
Specific function:
Membrane-anchoring subunit of succinate dehydrogenase (SDH)
Gene Name:
sdhD
Uniprot ID:
P0AC44
Molecular weight:
12867
General function:
Involved in succinate dehydrogenase activity
Specific function:
Membrane-anchoring subunit of succinate dehydrogenase (SDH)
Gene Name:
sdhC
Uniprot ID:
P69054
Molecular weight:
14299
General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
Required, probably indirectly, for the hydroxylation of 2-octaprenylphenol to 2-octaprenyl-6-hydroxy-phenol, the fourth step in ubiquinone biosynthesis. Specific for aerobically grown log-phase cells
Gene Name:
ubiB
Uniprot ID:
P0A6A0
Molecular weight:
63202