You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.

Quinone (YMDB00155)

Identification
YMDB IDYMDB00155
NameQuinone
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionQuinones are oxidised derivatives of aromatic compounds and are often readily made from reactive aromatic compounds with electron-donating substituents such as phenols and catechols. They are a common constituent of biologically relevant molecules (e.g. vitamin K1 is phylloquinone). They serve as electron acceptors in electron transport chains (e.g. photosystems I & II of photosynthesis, and aerobic respiration).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1,4-Benzoquine
  • 1,4-Benzoquinone
  • 1,4-Cyclohexadiene dioxide
  • 1,4-Cyclohexadienedione
  • 1,4-Diossibenzene
  • 1,4-Dioxy-benzol
  • 1,4-Dioxybenzene
  • 2,5-Cyclohexadiene-1,4-dione
  • Benzo-1,4-quinone
  • Benzo-chinon
  • Benzoquinone
  • Chinon
  • Chinone
  • Cyclohexadiene-1,4-dione
  • Cyclohexadienedione
  • Eldoquin
  • p-Benzoquinone
  • p-Chinon
  • p-Quinone
  • para-Benzoquinone
  • para-Quinone
  • Quinone1,4-Benzoquinone
  • Semiquinone anion
  • semiquinone radicals
  • 1,4-Benzochinon
  • 2,5-Cyclohexadiene-1-4-dione
CAS number106-51-4
WeightAverage: 108.0948
Monoisotopic: 108.021129372
InChI KeyAZQWKYJCGOJGHM-UHFFFAOYSA-N
InChIInChI=1S/C6H4O2/c7-5-1-2-6(8)4-3-5/h1-4H
IUPAC Namecyclohexa-2,5-diene-1,4-dione
Traditional IUPAC Namequinone
Chemical FormulaC6H4O2
SMILES[H]C1=C([H])C(=O)C([H])=C([H])C1=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentP-benzoquinones
Alternative Parents
Substituents
  • P-benzoquinone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point115.7 °C
Experimental Properties
PropertyValueReference
Water Solubility11.1 mg/mL at 18 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP0.20 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility45.4 g/LALOGPS
logP0.21ALOGPS
logP1.02ChemAxon
logS-0.38ALOGPS
pKa (Strongest Basic)-7.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity31.03 m³·mol⁻¹ChemAxon
Polarizability9.75 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm, Nucleus
Organoleptic PropertiesNot Available
SMPDB Pathways
Riboflavin metabolismPW002443 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Riboflavin metabolismec00740 Map00740
SMPDB Reactions
D-Alanine + water + Quinone → Ammonium + Pyruvic acid + Hydroquinone
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0zgi-9500000000-c8bfbbc465fad7929f87JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00xr-1900000000-9b99afb0e9c6350434a4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0zgi-9500000000-c8bfbbc465fad7929f87JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00xr-1900000000-9b99afb0e9c6350434a4JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9500000000-6664b553a87d4fc15f94JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-7900000000-fca2433f986ba378f8c9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00or-9000000000-6897ef153b4119e50cebJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014u-9000000000-9bddbff45c6d0d3e0cf1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-0zgi-9500000000-c8bfbbc465fad7929f87JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-QFT 7V, negativesplash10-014i-1900000000-6d13549d8c534563dc9bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-QFT 9V, negativesplash10-014i-1900000000-af62dc0334e009fe3e5bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-QFT 14V, negativesplash10-014i-3900000000-1167cf77177c0761168eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-d886efcfed5b0135bcd5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-7f5c75e048ee2f454e33JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9100000000-db1ffa9cf092dd5e4551JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-648d78080240a1294e4cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-648d78080240a1294e4cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5900000000-0f04c7bee6397237ee21JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-2c6cb60a5040c6239920JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-4900000000-f1f9c8ded0fe97bb684dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9000000000-3c2c54b9382bddbdf0dfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-62ea0dd9303aae554ccdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2900000000-7966cc06756dd3b8c736JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-28217a7272677bec662aJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0zgi-9200000000-8777cde0dbcbb2157cddJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Harman, Robert E.; Cason, James. The preparation of quinones from p-aminophenols obtained by electrolytic reduction of aromatic nitro compounds. Journal of Organic Chemistry (1952), 17 1058-62.
External Links:
ResourceLink
CHEBI ID16509
HMDB IDHMDB03364
Pubchem Compound ID4650
Kegg IDC00472
ChemSpider ID4489
FOODB IDFDB005755
WikipediaQuinone
BioCyc IDCPD-8130

Enzymes

Protein Details
1. Glycerol-3-phosphate dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
sn-glycerol 3-phosphate + a quinone = glycerone phosphate + a quinol
Gene Name:
GUT2
Uniprot ID:
P32191
Molecular weight:
72388.29688
Reactions
sn-glycerol 3-phosphate + a quinone → glycerone phosphate + a quinol.
Protein Details
2. Probable quinone oxidoreductase
General function:
Involved in zinc ion binding
Specific function:
NADPH + 2 quinone = NADP(+) + 2 semiquinone
Gene Name:
ZTA1
Uniprot ID:
P38230
Molecular weight:
37018.30078
Reactions
NADPH + 2 quinone → NADP(+) + 2 semiquinone.