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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 10:14:47 UTC
Update Date2021-09-14 15:45:29 UTC
HMDB IDHMDB0004067
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 1.14.18.1) could be a toxic metabolite in melanin biosynthesis (PMID: 6807981 , 1445949 , 413870 , 11461115 , 11171088 , 12755639 ).
Structure
Data?1588783883
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, MeSH
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
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
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
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.037Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility11.4 g/LALOGPS
logP10(1.1) g/LALOGPS
logP10(-0.95) g/LChemAxon
logS10(-1.2) 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+143.83731661259
DarkChem[M-H]-141.84131661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LeucodopachromeOC(=O)[C@@H]1CC2=CC(O)=C(O)C=C2N13421.2Standard polar33892256
LeucodopachromeOC(=O)[C@@H]1CC2=CC(O)=C(O)C=C2N12156.9Standard non polar33892256
LeucodopachromeOC(=O)[C@@H]1CC2=CC(O)=C(O)C=C2N12156.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Leucodopachrome,1TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]1CC2=CC(O)=C(O)C=C2N12154.9Semi standard non polar33892256
Leucodopachrome,1TMS,isomer #2C[Si](C)(C)OC1=CC2=C(C=C1O)N[C@H](C(=O)O)C22175.7Semi standard non polar33892256
Leucodopachrome,1TMS,isomer #3C[Si](C)(C)OC1=CC2=C(C=C1O)C[C@@H](C(=O)O)N22179.7Semi standard non polar33892256
Leucodopachrome,1TMS,isomer #4C[Si](C)(C)N1C2=CC(O)=C(O)C=C2C[C@H]1C(=O)O2156.6Semi standard non polar33892256
Leucodopachrome,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]1CC2=CC(O[Si](C)(C)C)=C(O)C=C2N12144.6Semi standard non polar33892256
Leucodopachrome,2TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H]1CC2=CC(O)=C(O[Si](C)(C)C)C=C2N12139.1Semi standard non polar33892256
Leucodopachrome,2TMS,isomer #3C[Si](C)(C)OC(=O)[C@@H]1CC2=CC(O)=C(O)C=C2N1[Si](C)(C)C2111.7Semi standard non polar33892256
Leucodopachrome,2TMS,isomer #4C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)N[C@H](C(=O)O)C22192.3Semi standard non polar33892256
Leucodopachrome,2TMS,isomer #5C[Si](C)(C)OC1=CC2=C(C=C1O)N([Si](C)(C)C)[C@H](C(=O)O)C22130.3Semi standard non polar33892256
Leucodopachrome,2TMS,isomer #6C[Si](C)(C)OC1=CC2=C(C=C1O)C[C@@H](C(=O)O)N2[Si](C)(C)C2132.0Semi standard non polar33892256
Leucodopachrome,3TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]1CC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2N12214.7Semi standard non polar33892256
Leucodopachrome,3TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H]1CC2=CC(O[Si](C)(C)C)=C(O)C=C2N1[Si](C)(C)C2149.5Semi standard non polar33892256
Leucodopachrome,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@@H]1CC2=CC(O)=C(O[Si](C)(C)C)C=C2N1[Si](C)(C)C2151.0Semi standard non polar33892256
Leucodopachrome,3TMS,isomer #4C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)[C@H](C(=O)O)C22148.2Semi standard non polar33892256
Leucodopachrome,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]1CC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2N1[Si](C)(C)C2205.2Semi standard non polar33892256
Leucodopachrome,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]1CC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2N1[Si](C)(C)C2167.1Standard non polar33892256
Leucodopachrome,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]1CC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2N1[Si](C)(C)C2156.4Standard polar33892256
Leucodopachrome,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CC2=CC(O)=C(O)C=C2N12437.6Semi standard non polar33892256
Leucodopachrome,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)N[C@H](C(=O)O)C22441.9Semi standard non polar33892256
Leucodopachrome,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)C[C@@H](C(=O)O)N22438.1Semi standard non polar33892256
Leucodopachrome,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C2=CC(O)=C(O)C=C2C[C@H]1C(=O)O2442.6Semi standard non polar33892256
Leucodopachrome,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CC2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C2N12621.1Semi standard non polar33892256
Leucodopachrome,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CC2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C2N12617.9Semi standard non polar33892256
Leucodopachrome,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CC2=CC(O)=C(O)C=C2N1[Si](C)(C)C(C)(C)C2607.9Semi standard non polar33892256
Leucodopachrome,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N[C@H](C(=O)O)C22690.1Semi standard non polar33892256
Leucodopachrome,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)N([Si](C)(C)C(C)(C)C)[C@H](C(=O)O)C22700.2Semi standard non polar33892256
Leucodopachrome,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)C[C@@H](C(=O)O)N2[Si](C)(C)C(C)(C)C2699.2Semi standard non polar33892256
Leucodopachrome,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2N12867.8Semi standard non polar33892256
Leucodopachrome,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CC2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C2N1[Si](C)(C)C(C)(C)C2856.5Semi standard non polar33892256
Leucodopachrome,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CC2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C2N1[Si](C)(C)C(C)(C)C2854.2Semi standard non polar33892256
Leucodopachrome,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[C@H](C(=O)O)C22914.8Semi standard non polar33892256
Leucodopachrome,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2N1[Si](C)(C)C(C)(C)C3051.3Semi standard non polar33892256
Leucodopachrome,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2N1[Si](C)(C)C(C)(C)C2965.2Standard non polar33892256
Leucodopachrome,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2N1[Si](C)(C)C(C)(C)C2648.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Leucodopachrome GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0900000000-35837217fc06e20917362017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Leucodopachrome GC-MS (3 TMS) - 70eV, Positivesplash10-00y3-3139000000-66e1777cafa8b458873d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Leucodopachrome GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucodopachrome 10V, Positive-QTOFsplash10-002b-0900000000-f7c2c2473d302b097c1f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucodopachrome 20V, Positive-QTOFsplash10-0uk9-0900000000-d938ebc784c186dfb0692017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucodopachrome 40V, Positive-QTOFsplash10-00di-5900000000-4af75e87edf64f19771c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucodopachrome 10V, Negative-QTOFsplash10-0006-0900000000-dd70919fd1f080a6e99f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucodopachrome 20V, Negative-QTOFsplash10-0f96-0900000000-6a40b4c319558396bbe02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucodopachrome 40V, Negative-QTOFsplash10-0fxy-2900000000-a4cf73cb9c5d1452df552017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucodopachrome 10V, Negative-QTOFsplash10-0006-0900000000-c1c8336c274a508bda242021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucodopachrome 20V, Negative-QTOFsplash10-0fdo-0900000000-563746630b866f82978f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucodopachrome 40V, Negative-QTOFsplash10-00dl-4900000000-f2f8683579276c5e47f22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucodopachrome 10V, Positive-QTOFsplash10-002b-0900000000-05dbda1a6ead55a72d672021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucodopachrome 20V, Positive-QTOFsplash10-0ufs-0900000000-d217d3c071a30de2b1292021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucodopachrome 40V, Positive-QTOFsplash10-007o-6900000000-dbea51bffeee77cdf0c52021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCCD details
FecesDetected but not QuantifiedNot QuantifiedAdult (>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
FooDB IDFDB023297
KNApSAcK IDC00051835
Chemspider ID141655
KEGG Compound IDC05604
BioCyc IDCPD-8652
BiGG ID46110
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound161255
PDB IDNot Available
ChEBI ID60872
Food Biomarker OntologyNot Available
VMH ID2C23DH56DHOXIN
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]