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Record Information
Version2.0
Creation Date2018-03-21 18:00:09 UTC
Update Date2018-03-21 18:07:51 UTC
Accession NumberT3D5002
Identification
Common NameL-Dopachrome
ClassSmall Molecule
DescriptionDopachrome is a cyclization product of L-DOPA and is an intermediate in the biosynthesis of melanin. Dopaquinone has an ortho-quinone ring, which is known to be neurotoxic and highly reactive with many other compounds (PMID: 413870). Dopachrome spontaneously gives rise to 5,6-dihydroxyindole (DHI) or it can be enzymatically metabolized by dopachrome tautomerase to give 5,6-dihydroxyindole-2-carboxylic acid (DHICA). DHI and its oxidation products are also toxic to cells. Many Parkinson's patients are treated with L-DOPA. However, long-term treatment with L-DOPA may actually worsen symptoms or may result in neurotic and psychotic symptoms. These may be due to dopachrome and dopaquinone accumulating in the brain of L-DOPA treated patients (PMID: 19131041, PMID: 12373519).
Compound TypeNot Available
Chemical Structure
Thumb
SynonymsNot Available
Chemical FormulaC9H7NO4
Average Molecular Mass193.158 g/mol
Monoisotopic Mass193.038 g/mol
CAS Registry Number89762-39-0
IUPAC Name(2S)-5,6-dioxo-2,3,5,6-tetrahydro-1H-indole-2-carboxylic acid
Traditional NameL-dopachrome
SMILESOC(=O)[C@@H]1CC2=CC(=O)C(=O)C=C2N1
InChI IdentifierInChI=1S/C9H7NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h2-3,6,10H,1H2,(H,13,14)/t6-/m0/s1
InChI KeyVJNCICVKUHKIIV-LURJTMIESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Indole or derivatives
  • Dihydroindole
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine
  • Vinylogous amide
  • Amino acid
  • Ketone
  • Cyclic ketone
  • Carboxylic acid
  • Secondary aliphatic amine
  • Enamine
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Secondary amine
  • Organoheterocyclic compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility10.2 g/LALOGPS
logP0.22ALOGPS
logP-0.087ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.67ChemAxon
pKa (Strongest Basic)-8.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.47 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.88 m³·mol⁻¹ChemAxon
Polarizability17.48 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0900000000-7d241073b22105a8fd50JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-323f4bcd8528fb467c2bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ba-7900000000-13c63b10c546db28b452JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-7278b78e7703333d1049JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006w-0900000000-37fa92b16a4a5557156cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006w-2900000000-a811e0992f3245b7b855JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-becbc589150d5f7b8591JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-96e2a94dd742e6e1937cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006w-1900000000-1956f467b1b38dab6842JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-ae6d437a06113eb43338JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004m-0900000000-5329f1d5b80270050bbbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006y-8900000000-bfc43ab0afc8b1b28dafJSpectraViewer
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001430
PubChem Compound IDNot Available
ChEMBL IDNot Available
ChemSpider IDNot Available
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available