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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:19:46 UTC
Update Date2017-12-07 02:35:53 UTC
HMDB IDHMDB0012133
Secondary Accession Numbers
  • HMDB12133
Metabolite Identification
Common Name1,2-Benzoquinone
Description1,2-Benzoquinone is a reactive electrophile that is an intermediate in benzene metabolism. It is substrate for the enzyme Catechol oxidase (EC 1.10.3.1) and can be generated from the oxidation of catechol. 1,2-Benzoquinone is capable of reacting with blood proteins to produce adducts.
Structure
Thumb
Synonyms
ValueSource
2-BenzoquinoneChEBI
3,5-Cyclohexadiene-1,2-dioneChEBI
Catechol quinoneChEBI
Cyclohexa-3,5-diene-1,2-dioneChEBI
O-BenzoquinoneChEBI
O-QuinoneChEBI
ortho-BenzoquinoneChEBI
3,5-Cyclohexadiene-1,2-dione (9ci)HMDB
benzo-1,2-QuinoneHMDB
Chemical FormulaC6H4O2
Average Molecular Weight108.0948
Monoisotopic Molecular Weight108.021129372
IUPAC Namecyclohexa-3,5-diene-1,2-dione
Traditional Nameo-quinone
CAS Registry Number583-63-1
SMILES
O=C1C=CC=CC1=O
InChI Identifier
InChI=1S/C6H4O2/c7-5-3-1-2-4-6(5)8/h1-4H
InChI KeyWOAHJDHKFWSLKE-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as o-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 2-positions, respectively.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentO-benzoquinones
Alternative Parents
Substituents
  • O-benzoquinone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility16.1 g/LALOGPS
logP0.86ALOGPS
logP1.33ChemAxon
logS-0.83ALOGPS
pKa (Strongest Basic)-8.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity31.18 m³·mol⁻¹ChemAxon
Polarizability9.73 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pb9-9500000000-1a07fadb8f28ea959a28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-59076600ed27ef7ff1adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-03f8747e1c9926da750aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-67fb84b6bf182032b41dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-4fb61a2d97ea508989e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-13ff869a1a7e1a44c970View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9700000000-fc958adc5ffed240f9c2View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004549
KNApSAcK IDNot Available
Chemspider ID10941
KEGG Compound IDC02351
BioCyc IDCPD-385
BiGG IDNot Available
Wikipedia Link1,2-Benzoquinone
METLIN IDNot Available
PubChem Compound11421
PDB IDNot Available
ChEBI ID17253
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Davila LY, Caldas MJ: Applicability of MNDO techniques AM1 and PM3 to ring-structured polymers. J Comput Chem. 2002 Sep;23(12):1135-42. [PubMed:12116382 ]
  2. TAPPI G, FORNI PV: [Mycostatic and mycocidal action of heterocyclic derivatives of obenzoquinone]. Farmaco Sci Tec. 1950 May-Jun;5(3):241-50. [PubMed:15435538 ]
  3. Acharya AS, Manjula BN, Murthy GS, Vithayathil PJ: The influence of esterification of carboxyl groups of ribonuclease-A on its structure and immunological activity. Int J Pept Protein Res. 1977;9(3):213-9. [PubMed:844939 ]
  4. Nicoll K, Robertson J, Lant N, Kelland LR, Rogers PM, Robins DJ: Synthesis and antimelanoma activity of reversed amide analogues of N-acetyl-4-S-cysteaminylphenol. Oncol Res. 2006;16(2):97-106. [PubMed:16898270 ]