Record Information
Version1.0
Creation Date2016-09-30 23:07:30 UTC
Update Date2020-05-21 16:28:46 UTC
BMDB IDBMDB0004058
Secondary Accession Numbers
  • BMDB04058
Metabolite Identification
Common Name5,6-Dihydroxyindole
Description5,6-Dihydroxyindole, also known as 5,6-dihydroxyindole or DHI, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. 5,6-Dihydroxyindole is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 5,6-Dihydroxyindole participates in a number of enzymatic reactions, within cattle. In particular, 5,6-Dihydroxyindole can be biosynthesized from L-dopachrome; which is mediated by the enzyme tyrosinase. In addition, 5,6-Dihydroxyindole can be converted into indole-5,6-quinone; which is catalyzed by the enzyme tyrosinase. In cattle, 5,6-dihydroxyindole is involved in the metabolic pathway called the tyrosine metabolism pathway.
Structure
Thumb
Synonyms
ValueSource
DHIChEBI
Dopamine lutineChEBI
5,6-DihydroxyindoleHMDB
Indole-5,6-diolHMDB
IndolylquinolHMDB
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 KeySGNZYJXNUURYCH-UHFFFAOYSA-N
Chemical Taxonomy
Description 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-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • 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
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 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.11 m³·mol⁻¹ChemAxon
Polarizability14.74 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
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, Positivesplash10-006t-0900000000-04c8c0b24d6ead789b88View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-4190000000-0de343d929acc2e0ab2fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-cd7bde656f825967dce0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-fc1c09de4df4722d5f82View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00sl-4900000000-88e693a5f86ce8b2fc07View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-48fdac0fa8522c16328bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-2d3e6f8819c9c5d32c21View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kg-4900000000-c98c0942f4239d6904b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-e9c84d792f3855d1e622View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-2900000000-6476034159460897f408View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufu-9300000000-b351609273dd4b0ae8d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-d32a0a3b410ab4200586View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1900000000-7917015f2c051992bf5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9300000000-bade444c07fe0e0b86feView in MoNA
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0004058
DrugBank IDDB01811
Phenol Explorer Compound IDNot Available
FooDB IDFDB023293
KNApSAcK IDNot Available
Chemspider ID102690
KEGG Compound IDC05578
BioCyc IDDIHYDROXYINDOLE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7009
PubChem Compound114683
PDB IDNot Available
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 ReferencesNot Available

Enzymes

General function:
Involved in cytokine activity
Specific function:
Pro-inflammatory cytokine. Involved in the innate immune response to bacterial pathogens. The expression of MIF at sites of inflammation suggests a role as mediator in regulating the function of macrophages in host defense. Counteracts the anti-inflammatory activity of glucocorticoids. Has phenylpyruvate tautomerase and dopachrome tautomerase activity (in vitro), but the physiological substrate is not known. It is not clear whether the tautomerase activity has any physiological relevance, and whether it is important for cytokine activity (By similarity).
Gene Name:
MIF
Uniprot ID:
P80177
Molecular weight:
12343.0
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:
A5PK65
Molecular weight:
12877.0
General function:
Involved in dopachrome isomerase activity
Specific function:
Catalyzes the conversion of L-dopachrome into 5,6-dihydroxyindole-2-carboxylic acid (DHICA). Involved in regulating eumelanin and phaeomelanin levels.
Gene Name:
DCT
Uniprot ID:
Q95119
Molecular weight:
58787.0
General function:
Involved in copper ion binding
Specific function:
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the initial and rate limiting step in the cascade of reactions leading to melanin production from tyrosine. In addition to hydroxylating tyrosine to DOPA (3,4-dihydroxyphenylalanine), also catalyzes the oxidation of DOPA to DOPA-quinone, and possibly the oxidation of DHI (5,6-dihydroxyindole) to indole-5,6 quinone.
Gene Name:
TYR
Uniprot ID:
Q8MIU0
Molecular weight:
60304.0
Reactions
L-Dopachrome + Oxygen → 5,6-Dihydroxyindole + Waterdetails
5,6-Dihydroxyindole + Oxygen → Indole-5,6-quinone + Waterdetails