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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-08-13 10:14:47 UTC
Update Date2017-10-23 19:04:10 UTC
HMDB IDHMDB0004067
Secondary Accession Numbers
  • HMDB04067
  • HMDB06340
Metabolite Identification
Common NameLeucodopachrome
DescriptionLeucodopachrome is an indolic intermediate in the melanogenesis pathway, the non-enzymatically 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 1.14.18.1) could be a toxic metabolite in melanin biosynthesis. (PMID: 6807981 , 1445949 , 413870 , 11461115 , 11171088 , 12755639 ).
Structure
Thumb
Synonyms
ValueSource
(S)-2-Carboxy-5,6-dihydroxyindolineChEBI
(S)-5,6-Dihydroxyindoline-2-carboxylic acidChEBI
cyclo-DopaChEBI
CyclodopaChEBI
L-2-Carboxy-2,3-dihydro-5,6-dihydroxyindoleChEBI
LeukodopachromeChEBI
(S)-5,6-Dihydroxyindoline-2-carboxylateGenerator
2,3-dihydro-5,6-Dihydroxyindole-2-carboxylateHMDB
2-Carboxy-2,3-dihydro-5,6-dihydroxyindoleHMDB
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
SMILES
OC(=O)[C@@H]1CC2=CC(O)=C(O)C=C2N1
InChI Identifier
InChI=1S/C9H9NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h2-3,6,10-12H,1H2,(H,13,14)/t6-/m0/s1
InChI KeyJDWYRSDDJVCWPB-LURJTMIESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as indolecarboxylic acids. These are compounds containing a carboxylic acid group linked to an indole.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassIndoles and derivatives
Direct ParentIndolecarboxylic acids
Alternative Parents
Substituents
  • 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
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.037Not Available
Predicted Properties
PropertyValueSource
Water Solubility11.4 g/LALOGPS
logP1.1ALOGPS
logP-0.95ChemAxon
logS-1.2ALOGPS
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
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, Positivesplash10-0udi-0900000000-35837217fc06e2091736View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00y3-3139000000-66e1777cafa8b458873dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-f7c2c2473d302b097c1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0900000000-d938ebc784c186dfb069View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-5900000000-4af75e87edf64f19771cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-dd70919fd1f080a6e99fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f96-0900000000-6a40b4c319558396bbe0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fxy-2900000000-a4cf73cb9c5d1452df55View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Feces
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
Displaying entries 1 - 5 of 8 in total
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Children (1-13 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothCCD details
FecesDetected but not Quantified Adult (>18 years old)BothICD details
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 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
References
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 ]