L-Dopaquinone (CHEM003923)

Record Information
Version1.0
Creation Date2014-10-02 19:01:44 UTC
Update Date2026-04-05 15:24:58 UTC
Accession NumberCHEM003923
Identification
Common NameL-Dopaquinone
ClassSmall Molecule
Description
Implicated in food discolouration (enzymatic browning).
Contaminant Sources
  • FooDB Chemicals
  • T3DB toxins
Contaminant Type
  • Animal Toxin
  • Human Neurotoxin
  • Metabolite
  • Natural Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Dopa O-quinoneChEMBL, HMDB
O-DopaquinoneMeSH, HMDB
DopaquinoneMeSH, HMDB
Dopaquinone, (S)-isomerMeSH, HMDB
4-(2-Carboxy-2-aminoethyl)-1,2-benzoquinoneMeSH, HMDB
2-Amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoateGenerator
Chemical FormulaC9H9NO4
Average Molecular Mass195.172 g/mol
Monoisotopic Mass195.053 g/mol
CAS Registry Number110810-88-3
IUPAC Name2-amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid
Traditional Name2-amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid
SMILESNC(CC1=CC(=O)C(=O)C=C1)C(O)=O
InChI IdentifierInChI=1S/C9H9NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6H,3,10H2,(H,13,14)
InChI KeyAHMIDUVKSGCHAU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • O-benzoquinone
  • Quinone
  • Ketone
  • Cyclic ketone
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.58 g/LALOGPS
logP-1.9ALOGPS
logP-2.1ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)9.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area97.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.48 m³·mol⁻¹ChemAxon
Polarizability18.12 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsChronically high levels of DOPA-quinone is associated with Parkinson's disease.
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0039119
FooDB IDFDB018629
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkL-Dopaquinone
Chemspider ID662
ChEBI IDNot Available
PubChem Compound ID682
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.