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Record Information
Version3.6
Creation Date2006-08-13 10:04:57 UTC
Update Date2016-05-20 17:13:24 UTC
HMDB IDHMDB04058
Secondary Accession NumbersNone
Metabolite Identification
Common Name5,6-Dihydroxyindole
Description5,6-Dihydroxyindole is a substrate for Tyrosinase.
Structure
Thumb
Synonyms
ValueSource
DHIChEBI
Dopamine lutineChEBI
AminochromeHMDB
DopaminochromeHMDB
Chemical FormulaC8H7NO2
Average Molecular Weight149.1467
Monoisotopic Molecular Weight149.047678473
IUPAC Name1H-indole-5,6-diol
Traditional Name5,6-dihydroxyindole
CAS Registry Number3131-52-0
SMILES
OC1=C(O)C=C2C=CNC2=C1
InChI Identifier
InChI=1S/C8H7NO2/c10-7-3-5-1-2-9-6(5)4-8(7)11/h1-4,9-11H
InChI KeyInChIKey=SGNZYJXNUURYCH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassHydroxyindoles
Direct ParentHydroxyindoles
Alternative Parents
Substituents
  • Hydroxyindole
  • Indole
  • 1,2-diphenol
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 Solubility5.78 mg/mLALOGPS
logP1.11ALOGPS
logP1.46ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)8.72ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area56.25 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.11 m3·mol-1ChemAxon
Polarizability14.74 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
AlkaptonuriaSMP00169Not Available
Disulfiram PathwaySMP00429Not Available
Dopamine beta-hydroxylase deficiencySMP00498Not Available
HawkinsinuriaSMP00190Not Available
Monoamine oxidase-a deficiency (MAO-A)SMP00533Not Available
Tyrosine MetabolismSMP00006map00350
Tyrosinemia Type ISMP00218Not Available
Tyrosinemia, transient, of the newbornSMP00494Not 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 IDFDB023293
KNApSAcK IDNot Available
Chemspider ID102690
KEGG Compound IDC05578
BioCyc IDDIHYDROXYINDOLE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04058
Metagene LinkHMDB04058
METLIN ID7009
PubChem Compound114683
PDB ID3ID
ChEBI ID27404
References
Synthesis ReferenceHarley-Mason, John. Melanin and its precursors. VI. Further synthesis of 5,6-dihydroxyindole and its derivatives. Journal of the Chemical Society (1953), 200-3.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pavel S: A new possible pathogenesis of some gallstones. Med Hypotheses. 1984 Jul;14(3):285-92. [6472156 ]
  2. Pavel S, Muskiet FA: Eumelanin (precursor) metabolites as markers for pigmented malignant melanoma: a preliminary report. Cancer Detect Prev. 1983;6(1-2):311-6. [6883388 ]
  3. Pavel S, Boverhof R, Wolthers BG: Identification of 5-hydroxy-6-indolyl-O-sulfate in urine of patients with malignant melanoma. J Invest Dermatol. 1984 Jun;82(6):577-9. [6547157 ]

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
Reactions
5,6-Dihydroxyindole + Oxygen → Indole-5,6-quinone + Waterdetails
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
General function:
Involved in D-dopachrome decarboxylase activity
Specific function:
Tautomerization of D-dopachrome with decarboxylation to give 5,6-dihydroxyindole (DHI).
Gene Name:
DDT
Uniprot ID:
P30046
Molecular weight:
12711.605
Reactions
D-Dopachrome → 5,6-Dihydroxyindole + CO(2)details