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Showing Compound Leucodopachrome (FDB023297)

Record Information
Version1.0
Creation date2011-09-21 00:27:41 UTC
Update date2019-11-26 03:21:08 UTC
Primary IDFDB023297
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]. Leucodopachrome is found in many foods, some of which are chives, saffron, leek, and red beetroot.
CAS Number18766-67-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(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
2,3-Dihydro-5,6-dihydroxyindole-2-carboxylatehmdb
cyclo-DopaChEBI
cyclodopahmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H9NO4
IUPAC name(2S)-5,6-dihydroxy-2,3-dihydro-1H-indole-2-carboxylic acid
InChI IdentifierInChI=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
Isomeric SMILESOC(=O)[C@@H]1CC2=CC(O)=C(O)C=C2N1
Average Molecular Weight195.1721
Monoisotopic Molecular Weight195.053157781
Classification
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
Disposition

Route of exposure:

Biological location:

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSLeucodopachrome, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-0900000000-35837217fc06e2091736Spectrum
Predicted GC-MSLeucodopachrome, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00y3-3139000000-66e1777cafa8b458873dSpectrum
Predicted GC-MSLeucodopachrome, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-f7c2c2473d302b097c1f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0900000000-d938ebc784c186dfb0692017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-5900000000-4af75e87edf64f19771c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-dd70919fd1f080a6e99f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f96-0900000000-6a40b4c319558396bbe02017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fxy-2900000000-a4cf73cb9c5d1452df552017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-c1c8336c274a508bda242021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fdo-0900000000-563746630b866f82978f2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-4900000000-f2f8683579276c5e47f22021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-05dbda1a6ead55a72d672021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ufs-0900000000-d217d3c071a30de2b1292021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-007o-6900000000-dbea51bffeee77cdf0c52021-09-25View Spectrum
NMRNot Available
ChemSpider ID141655
ChEMBL IDNot Available
KEGG Compound IDC05604
Pubchem Compound ID161255
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04067
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID46110
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Tyrosine MetabolismSMP00006 map00350
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference