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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:30:22 UTC
HMDB IDHMDB0001430
Secondary Accession Numbers
  • HMDB01430
Metabolite Identification
Common NameL-Dopachrome
DescriptionThe non-decarboxylative tautomerization of L-dopachrome to 5,6-dihydroxyindole-2-carboxylic acid in the melanin biosynthetic pathway is catalyzed by Tyrosinase-related protein-2, a melanocyte-specific enzyme. (PMID 11095412 ).
Structure
Thumb
Synonyms
ValueSource
2-L-Carboxy-2,3-dihydroindole-5,6-quinoneHMDB
Chemical FormulaC9H7NO4
Average Molecular Weight193.1562
Monoisotopic Molecular Weight193.037507717
IUPAC Name(2S)-5,6-dioxo-2,4,5,6-tetrahydro-1H-indole-2-carboxylic acid
Traditional NameL-dopachrome
CAS Registry Number89762-39-0
SMILES
OC(=O)[C@H]1NC2=CC(=O)C(=O)CC2=C1
InChI Identifier
InChI=1S/C9H7NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h1,3,6,10H,2H2,(H,13,14)/t6-/m0/s1
InChI KeyCKZOQLKEDKSKJR-LURJTMIESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Indole or derivatives
  • Pyrroline carboxylic acid
  • Pyrroline carboxylic acid or derivatives
  • Cyclohexenone
  • Pyrroline
  • Vinylogous amide
  • Ketone
  • Amino acid
  • Cyclic ketone
  • Carboxylic acid
  • Secondary aliphatic amine
  • Enamine
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

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
logP0.16ALOGPS
logP-0.48ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.7ChemAxon
pKa (Strongest Basic)1.79ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.47 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.75 m³·mol⁻¹ChemAxon
Polarizability17.55 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-0900000000-b29aeb2f316d1be5cc27View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-4940000000-064b2c27513d736d4a3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0900000000-15655f8c3742466db9e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-7e9500b1b8bb20b775f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00b9-9800000000-7bf7e0ac2182eb92b5b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-ba3610e73ecb5b70f371View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006w-0900000000-e8757ea0a01dda3b8657View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006w-2900000000-905b41c7cddb19052686View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
AlkaptonuriaPw000180Pw000180 greyscalePw000180 simpleNot Available
Disulfiram PathwayPw000431Pw000431 greyscalePw000431 simpleNot Available
Dopamine beta-hydroxylase deficiencyPw000474Pw000474 greyscalePw000474 simpleNot Available
HawkinsinuriaPw000181Pw000181 greyscalePw000181 simpleNot Available
Monoamine oxidase-a deficiency (MAO-A)Pw000509Pw000509 greyscalePw000509 simpleNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022618
KNApSAcK IDNot Available
Chemspider ID17216120
KEGG Compound IDC01693
BioCyc IDL-DOPACHROME
BiGG ID1443253
Wikipedia LinkNot Available
METLIN ID6241
PubChem Compound439549
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 ]

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