You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
StatusDetected but not Quantified
Creation Date2006-08-13 10:14:47 UTC
Update Date2019-07-23 05:46:02 UTC
Secondary Accession Numbers
  • HMDB0006340
  • HMDB04067
  • HMDB06340
Metabolite Identification
Common NameLeucodopachrome
DescriptionLeucodopachrome is an indolic intermediate in the melanogenesis pathway, the non-enzymatic product of dopaquinone through cyclization in a reaction whose operation is determined by a pH greater than 4 (melanin synthesis in human pigment cell lysates is maximal at pH 6.8). Leucodopachrome participates in redox exchange with dopaquinone to give the eumelanin precursor dopachrome plus DOPA. Dopaquinone (the quinone intermediate resulting from tyrosinase-mediated oxidation of tyrosine, monophenol dihydroxyphenylalanine:oxygen oxidoreductase, EC could be a toxic metabolite in melanin biosynthesis (PMID: 6807981 , 1445949 , 413870 , 11461115 , 11171088 , 12755639 ).
(S)-5,6-Dihydroxyindoline-2-carboxylic acidChEBI
Chemical FormulaC9H9NO4
Average Molecular Weight195.1721
Monoisotopic Molecular Weight195.053157781
IUPAC Name(2S)-5,6-dihydroxy-2,3-dihydro-1H-indole-2-carboxylic acid
Traditional Namecyclodopa
CAS Registry Number18766-67-1
InChI Identifier
Chemical Taxonomy
Description belongs to the class of organic compounds known as indolecarboxylic acids. Indolecarboxylic acids are compounds containing a carboxylic acid group linked to an indole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolecarboxylic acids and derivatives
Direct ParentIndolecarboxylic acids
Alternative Parents
  • Indolecarboxylic acid
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Dihydroindole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Secondary aliphatic/aromatic amine
  • Aralkylamine
  • Benzenoid
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Secondary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Route of exposure:

Biological location:


Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.037Not Available
Predicted Properties
Water Solubility11.4 g/LALOGPS
pKa (Strongest Acidic)5.16ChemAxon
pKa (Strongest Basic)1.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area89.79 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.35 m³·mol⁻¹ChemAxon
Polarizability18.45 ųChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0900000000-35837217fc06e2091736JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00y3-3139000000-66e1777cafa8b458873dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-f7c2c2473d302b097c1fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0900000000-d938ebc784c186dfb069JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-5900000000-4af75e87edf64f19771cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-dd70919fd1f080a6e99fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f96-0900000000-6a40b4c319558396bbe0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fxy-2900000000-a4cf73cb9c5d1452df55JSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Normal Concentrations
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Children (1-13 years old)BothNormal details
Abnormal Concentrations
FecesDetected but not Quantified Adult (>18 years old)BothCCD details
FecesDetected but not Quantified Adult (>18 years old)BothIleal Crohn's disease details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023297
KNApSAcK IDNot Available
Chemspider ID141655
KEGG Compound IDC05604
BioCyc IDNot Available
BiGG ID46110
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound161255
PDB IDNot Available
ChEBI ID60872
Food Biomarker OntologyNot Available
VMH IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Canovas FG, Garcia-Carmona F, Sanchez JV, Pastor JL, Teruel JA: The role of pH in the melanin biosynthesis pathway. J Biol Chem. 1982 Aug 10;257(15):8738-44. [PubMed:6807981 ]
  2. Rodriguez-Lopez JN, Banon-Arnao M, Martinez-Ortiz F, Tudela J, Acosta M, Varon R, Garcia-Canovas F: Catalytic oxidation of 2,4,5-trihydroxyphenylalanine by tyrosinase: identification and evolution of intermediates. Biochim Biophys Acta. 1992 Nov 20;1160(2):221-8. [PubMed:1445949 ]
  3. Graham DG, Tiffany SM, Vogel FS: The toxicity of melanin precursors. J Invest Dermatol. 1978 Feb;70(2):113-6. [PubMed:413870 ]
  4. Ancans J, Tobin DJ, Hoogduijn MJ, Smit NP, Wakamatsu K, Thody AJ: Melanosomal pH controls rate of melanogenesis, eumelanin/phaeomelanin ratio and melanosome maturation in melanocytes and melanoma cells. Exp Cell Res. 2001 Aug 1;268(1):26-35. [PubMed:11461115 ]
  5. Olivares C, Jimenez-Cervantes C, Lozano JA, Solano F, Garcia-Borron JC: The 5,6-dihydroxyindole-2-carboxylic acid (DHICA) oxidase activity of human tyrosinase. Biochem J. 2001 Feb 15;354(Pt 1):131-9. [PubMed:11171088 ]
  6. Land EJ, Ramsden CA, Riley PA: Tyrosinase autoactivation and the chemistry of ortho-quinone amines. Acc Chem Res. 2003 May;36(5):300-8. [PubMed:12755639 ]