Record Information
Version1.0
Creation Date2016-09-30 23:04:01 UTC
Update Date2020-05-21 16:28:35 UTC
BMDB IDBMDB0003364
Secondary Accession Numbers
  • BMDB03364
Metabolite Identification
Common NameQuinone
DescriptionQuinone, also known as benzoquinone or 1,4-benzochinon, 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. Quinone is an extremely weak basic (essentially neutral) compound (based on its pKa). Quinone exists in all living species, ranging from bacteria to humans. Quinone is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
1,4-BenzochinonChEBI
2,5-Cyclohexadiene-1,4-dioneChEBI
Benzo-1,4-quinoneChEBI
BenzoquinoneChEBI
p-BenzoquinoneChEBI
p-ChinonChEBI
p-QuinoneChEBI
Para-benzoquinoneChEBI
ChinoneKegg
1,4-BenzoquinoneKegg
1,4-BenzoquineHMDB
1,4-Cyclohexadiene dioxideHMDB
1,4-CyclohexadienedioneHMDB
1,4-DiossibenzeneHMDB
1,4-Dioxy-benzolHMDB
1,4-DioxybenzeneHMDB
2,5-Cyclohexadiene-1-4-dioneHMDB
Benzo-chinonHMDB
ChinonHMDB
Cyclohexadiene-1,4-dioneHMDB
CyclohexadienedioneHMDB
EldoquinHMDB
Para-quinoneHMDB
Quinone1,4-benzoquinoneHMDB
Semiquinone anionHMDB
Semiquinone radicalsHMDB
Chemical FormulaC6H4O2
Average Molecular Weight108.0948
Monoisotopic Molecular Weight108.021129372
IUPAC Namecyclohexa-2,5-diene-1,4-dione
Traditional Namequinone
CAS Registry Number106-51-4
SMILES
O=C1C=CC(=O)C=C1
InChI Identifier
InChI=1S/C6H4O2/c7-5-1-2-6(8)4-3-5/h1-4H
InChI KeyAZQWKYJCGOJGHM-UHFFFAOYSA-N
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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point115.7 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility11.1 mg/mL at 18 °CNot Available
LogP0.2HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0zgi-9500000000-c8bfbbc465fad7929f87View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00xr-1900000000-9b99afb0e9c6350434a4View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0zgi-9500000000-c8bfbbc465fad7929f87View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00xr-1900000000-9b99afb0e9c6350434a4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9500000000-6664b553a87d4fc15f94View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-7900000000-fca2433f986ba378f8c9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00or-9000000000-6897ef153b4119e50cebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014u-9000000000-9bddbff45c6d0d3e0cf1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-0zgi-9500000000-c8bfbbc465fad7929f87View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-QFT 7V, negativesplash10-014i-1900000000-6d13549d8c534563dc9bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-QFT 9V, negativesplash10-014i-1900000000-af62dc0334e009fe3e5bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-QFT 14V, negativesplash10-014i-3900000000-1167cf77177c0761168eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-d886efcfed5b0135bcd5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-7f5c75e048ee2f454e33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9100000000-db1ffa9cf092dd5e4551View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-648d78080240a1294e4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-648d78080240a1294e4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5900000000-0f04c7bee6397237ee21View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-2c6cb60a5040c6239920View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-4900000000-f1f9c8ded0fe97bb684dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9000000000-3c2c54b9382bddbdf0dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-62ea0dd9303aae554ccdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2900000000-7966cc06756dd3b8c736View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-28217a7272677bec662aView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0zgi-9200000000-8777cde0dbcbb2157cddView in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Bone Marrow
  • Fibroblasts
  • Kidney
  • Liver
  • Neuron
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Bone MarrowExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0003364
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB005755
KNApSAcK IDNot Available
Chemspider ID4489
KEGG Compound IDC00472
BioCyc IDP-BENZOQUINONE
BiGG IDNot Available
Wikipedia Link1,4-Benzoquinone
METLIN ID6905
PubChem Compound4650
PDB IDNot Available
ChEBI ID16509
References
Synthesis ReferenceHarman, 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.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q29437
Molecular weight:
84757.0
General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
GPD2
Uniprot ID:
A6QLU1
Molecular weight:
80763.0
Reactions
Glycerol 3-phosphate + Quinone → Dihydroxyacetone phosphate + Hydroquinonedetails
Dihydroxyacetone phosphate + Quinone → Glycerol 3-phosphate + Hydroquinonedetails
General function:
Nucleotide transport and metabolism
Specific function:
Catalyzes the conversion of dihydroorotate to orotate with quinone as electron acceptor.
Gene Name:
DHODH
Uniprot ID:
Q5E9W3
Molecular weight:
42776.0
Reactions
L-Dihydroorotic acid + Quinone → Orotic acid + quinoldetails
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity (By similarity).
Gene Name:
AOC3
Uniprot ID:
Q9TTK6
Molecular weight:
84500.0
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
O46406
Molecular weight:
84883.0
General function:
Energy production and conversion
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone.
Gene Name:
NDUFS7
Uniprot ID:
P42026
Molecular weight:
23771.0
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Not Available
Gene Name:
AOC1
Uniprot ID:
Q3MHQ1
Molecular weight:
85533.0
General function:
Energy production and conversion
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone.
Gene Name:
NDUFS2
Uniprot ID:
P17694
Molecular weight:
52556.0
General function:
Involved in copper ion binding
Specific function:
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the initial and rate limiting step in the cascade of reactions leading to melanin production from tyrosine. In addition to hydroxylating tyrosine to DOPA (3,4-dihydroxyphenylalanine), also catalyzes the oxidation of DOPA to DOPA-quinone, and possibly the oxidation of DHI (5,6-dihydroxyindole) to indole-5,6 quinone.
Gene Name:
TYR
Uniprot ID:
Q8MIU0
Molecular weight:
60304.0
Reactions
2 Hydroquinone + Oxygen →2 Quinone +2 Waterdetails
General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
NDUFS7
Uniprot ID:
A8WFQ0
Molecular weight:
20122.0