Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-23 23:16:17 UTC
Update Date2022-09-01 02:02:02 UTC
MiMeDB IDMMDBc0047930
Metabolite Identification
Common NameL-Dopachrome
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 ).
Structure
SynonymsNot Available
Chemical FormulaC9H7NO4
Average Molecular Weight193.158
Monoisotopic Molecular Weight193.037507709
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number89762-39-0
SMILESNot Available
InChI Identifier
InChI=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