You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2009-04-06 16:21:13 UTC
Update Date2016-02-11 01:23:54 UTC
HMDB IDHMDB12219
Secondary Accession NumbersNone
Metabolite Identification
Common NameDopamine quinone
DescriptionDopamine-quinone is synthesized by oxidation of the catechol ring of dopamine. If this occurs within the neuronal cytosol, the quinone may react with cytosolic components, particularly with cysteine residues. (PMID: 12835101 ). Dopamine quinone is produce by the reaction between dopamine and oxygen, with water as the byproduct. The reaction is catalyzed by the tyrosinase precursor.
Structure
Thumb
Synonyms
ValueSource
4-(2-Aminoethyl)-1,2-benzoquinoneChEBI
4-(2-Aminoethyl)-O-benzoquinoneChEBI
Dopamine O-quinoneChEBI
DoQChEBI
4-(2-Aminoethyl)-3,5-cyclohexadiene-1,2-dioneHMDB
DopaminoquinoneHMDB
Chemical FormulaC8H9NO2
Average Molecular Weight151.1626
Monoisotopic Molecular Weight151.063328537
IUPAC Name4-(2-aminoethyl)cyclohexa-3,5-diene-1,2-dione
Traditional Name4-(2-aminoethyl)cyclohexa-3,5-diene-1,2-dione
CAS Registry Number50673-96-6
SMILES
NCCC1=CC(=O)C(=O)C=C1
InChI Identifier
InChI=1S/C8H9NO2/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5H,3-4,9H2
InChI KeyInChIKey=PQPXZWUZIOASKS-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 ClassOrganooxygen compounds
ClassCarbonyl compounds
Sub ClassKetones
Direct ParentO-benzoquinones
Alternative Parents
Substituents
  • O-benzoquinone
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 Solubility6.8 mg/mLALOGPS
logP-0.29ALOGPS
logP0.47ChemAxon
logS-1.4ALOGPS
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area60.16 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.65 m3·mol-1ChemAxon
Polarizability15.25 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00614
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB028863
KNApSAcK IDNot Available
Chemspider ID142759
KEGG Compound IDNot Available
BioCyc IDCPD-8851
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12219
Metagene LinkHMDB12219
METLIN IDNot Available
PubChem Compound162602
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sulzer D, Zecca L: Intraneuronal dopamine-quinone synthesis: a review. Neurotox Res. 2000 Feb;1(3):181-95. [12835101 ]