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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
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 + QuinoneAmmonium + Pyruvic acid + Hydroquinone
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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

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.
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.