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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-03-05 03:47:09 UTC
HMDB IDHMDB0001430
Secondary Accession Numbers
  • HMDB01430
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
Thumb
Synonyms
ValueSource
2-L-Carboxy-2,3-dihydroindole-5,6-quinoneChEBI
Chemical FormulaC9H7NO4
Average Molecular Weight193.158
Monoisotopic Molecular Weight193.037507709
IUPAC Name(2S)-5,6-dioxo-2,3,5,6-tetrahydro-1H-indole-2-carboxylic acid
Traditional NameL-dopachrome
CAS Registry Number89762-39-0
SMILES
OC(=O)[C@@H]1CC2=CC(=O)C(=O)C=C2N1
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
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentD-alpha-amino acids
Alternative Parents
Substituents
  • D-alpha-amino acid
  • Dihydroindole
  • Indole or derivatives
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine carboxylic acid
  • Vinylogous amide
  • Pyrrolidine
  • Cyclic ketone
  • Ketone
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Enamine
  • Secondary aliphatic amine
  • Carboxylic acid
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

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 Solubility11.9 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
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
AlkaptonuriaThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Disulfiram Action PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Dopamine beta-hydroxylase deficiencyThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
HawkinsinuriaThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Monoamine oxidase-a deficiency (MAO-A)ThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4573572
KEGG Compound IDC01693
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5459802
PDB IDNot Available
ChEBI ID15772
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pak BJ, Li Q, Kerbel RS, Ben-David Y: TYRP2-mediated resistance to cis-diamminedichloroplatinum (II) in human melanoma cells is independent of tyrosinase and TYRP1 expression and melanin content. Melanoma Res. 2000 Oct;10(5):499-505. [PubMed:11095412 ]
  2. Graham DG, Tiffany SM, Vogel FS: The toxicity of melanin precursors. J Invest Dermatol. 1978 Feb;70(2):113-6. [PubMed:413870 ]
  3. Hattoria N, Wanga M, Taka H, Fujimura T, Yoritaka A, Kubo S, Mochizuki H: Toxic effects of dopamine metabolism in Parkinson's disease. Parkinsonism Relat Disord. 2009 Jan;15 Suppl 1:S35-8. doi: 10.1016/S1353-8020(09)70010-0. [PubMed:19131041 ]
  4. Kostrzewa RM, Kostrzewa JP, Brus R: Neuroprotective and neurotoxic roles of levodopa (L-DOPA) in neurodegenerative disorders relating to Parkinson's disease. Amino Acids. 2002;23(1-3):57-63. doi: 10.1007/s00726-001-0110-x. [PubMed:12373519 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:
TYR
Uniprot ID:
P14679
Molecular weight:
60392.69
General function:
Involved in cell surface binding
Specific function:
Pro-inflammatory cytokine. Involved in the innate immune response to bacterial pathogens. The expression of MIF at sites of inflammation suggests a role as mediator in regulating the function of macrophages in host defense. Counteracts the anti-inflammatory activity of glucocorticoids. Has phenylpyruvate tautomerase and dopachrome tautomerase activity (in vitro), but the physiological substrate is not known. It is not clear whether the tautomerase activity has any physiological relevance, and whether it is important for cytokine activity.
Gene Name:
MIF
Uniprot ID:
P14174
Molecular weight:
12476.19
Reactions
L-Dopachrome → 5,6-Dihydroxyindole-2-carboxylic aciddetails
General function:
Involved in oxidoreductase activity
Specific function:
Involved in regulating eumelanin and phaeomelanin levels.
Gene Name:
DCT
Uniprot ID:
P40126
Molecular weight:
62928.215
Reactions
L-Dopachrome → 5,6-Dihydroxyindole-2-carboxylic aciddetails