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Record Information
Version4.0
Creation Date2009-04-06 16:21:13 UTC
Update Date2017-09-22 00:16:33 UTC
HMDB IDHMDB0012219
Secondary Accession Numbers
  • HMDB12219
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 KeyPQPXZWUZIOASKS-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as o-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 2-positions, respectively.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentO-benzoquinones
Alternative Parents
Substituents
  • O-benzoquinone
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • 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
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      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 LinkHMDB0012219
      METLIN IDNot Available
      PubChem Compound162602
      PDB IDNot Available
      ChEBI ID74684
      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. [PubMed:12835101 ]