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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 10:04:57 UTC
Update Date2020-04-27 15:50:28 UTC
HMDB IDHMDB0004058
Secondary Accession Numbers
  • HMDB04058
Metabolite Identification
Common Name5,6-Dihydroxyindole
Description5,6-Dihydroxyindole, also known as aminochrome 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 an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, 5,6-dihydroxyindole participates in a number of enzymatic reactions. In particular, 5,6-dihydroxyindole can be biosynthesized from L-dopachrome through the action of the enzyme tyrosinase. In addition, 5,6-dihydroxyindole can be converted into indole-5,6-quinone; which is catalyzed by the enzyme tyrosinase. In humans, 5,6-dihydroxyindole is involved in the metabolic disorder called hawkinsinuria.
Structure
Data?1588002628
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
Physiological effect

Adverse health effect

Disposition

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.78 g/LALOGPS
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+130.45531661259
DarkChem[M-H]-129.58931661259
DeepCCS[M+H]+130.34730932474
DeepCCS[M-H]-127.18430932474
DeepCCS[M-2H]-164.15430932474
DeepCCS[M+Na]+139.52230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5,6-DihydroxyindoleOC1=C(O)C=C2C=CNC2=C13514.5Standard polar33892256
5,6-DihydroxyindoleOC1=C(O)C=C2C=CNC2=C11845.1Standard non polar33892256
5,6-DihydroxyindoleOC1=C(O)C=C2C=CNC2=C11844.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5,6-Dihydroxyindole,1TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C=C[NH]2)C=C1O1897.5Semi standard non polar33892256
5,6-Dihydroxyindole,1TMS,isomer #2C[Si](C)(C)OC1=CC2=C(C=C1O)[NH]C=C21909.4Semi standard non polar33892256
5,6-Dihydroxyindole,1TMS,isomer #3C[Si](C)(C)N1C=CC2=CC(O)=C(O)C=C211954.4Semi standard non polar33892256
5,6-Dihydroxyindole,2TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)[NH]C=C21964.9Semi standard non polar33892256
5,6-Dihydroxyindole,2TMS,isomer #2C[Si](C)(C)OC1=CC2=C(C=CN2[Si](C)(C)C)C=C1O1940.9Semi standard non polar33892256
5,6-Dihydroxyindole,2TMS,isomer #3C[Si](C)(C)OC1=CC2=C(C=C1O)N([Si](C)(C)C)C=C21949.6Semi standard non polar33892256
5,6-Dihydroxyindole,3TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)C=C22024.3Semi standard non polar33892256
5,6-Dihydroxyindole,3TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)C=C21977.1Standard non polar33892256
5,6-Dihydroxyindole,3TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)C=C21892.3Standard polar33892256
5,6-Dihydroxyindole,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C[NH]2)C=C1O2165.6Semi standard non polar33892256
5,6-Dihydroxyindole,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)[NH]C=C22173.8Semi standard non polar33892256
5,6-Dihydroxyindole,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C=CC2=CC(O)=C(O)C=C212229.8Semi standard non polar33892256
5,6-Dihydroxyindole,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[NH]C=C22450.1Semi standard non polar33892256
5,6-Dihydroxyindole,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2=C(C=CN2[Si](C)(C)C(C)(C)C)C=C1O2443.1Semi standard non polar33892256
5,6-Dihydroxyindole,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)N([Si](C)(C)C(C)(C)C)C=C22448.0Semi standard non polar33892256
5,6-Dihydroxyindole,3TBDMS,isomer #1CC(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=C22679.8Semi standard non polar33892256
5,6-Dihydroxyindole,3TBDMS,isomer #1CC(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=C22630.4Standard non polar33892256
5,6-Dihydroxyindole,3TBDMS,isomer #1CC(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=C22263.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5,6-Dihydroxyindole GC-MS (Non-derivatized) - 70eV, Positivesplash10-006t-0900000000-04c8c0b24d6ead789b882017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,6-Dihydroxyindole GC-MS (2 TMS) - 70eV, Positivesplash10-00di-4190000000-0de343d929acc2e0ab2f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,6-Dihydroxyindole 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 - 5,6-Dihydroxyindole 10V, Positive-QTOFsplash10-0udi-0900000000-cd7bde656f825967dce02017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole 20V, Positive-QTOFsplash10-0udi-0900000000-fc1c09de4df4722d5f822017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole 40V, Positive-QTOFsplash10-00sl-4900000000-88e693a5f86ce8b2fc072017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole 10V, Negative-QTOFsplash10-0002-0900000000-48fdac0fa8522c16328b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole 20V, Negative-QTOFsplash10-0002-0900000000-2d3e6f8819c9c5d32c212017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole 40V, Negative-QTOFsplash10-00kg-4900000000-c98c0942f4239d6904b62017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole 10V, Positive-QTOFsplash10-0udi-0900000000-e9c84d792f3855d1e6222021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole 20V, Positive-QTOFsplash10-0udi-2900000000-6476034159460897f4082021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole 40V, Positive-QTOFsplash10-0ufu-9300000000-b351609273dd4b0ae8d62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole 10V, Negative-QTOFsplash10-0002-0900000000-d32a0a3b410ab42005862021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole 20V, Negative-QTOFsplash10-0002-1900000000-7917015f2c051992bf5a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole 40V, Negative-QTOFsplash10-00kf-9300000000-bade444c07fe0e0b86fe2021-09-24Wishart 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 LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH IDCE4888
MarkerDB IDNot Available
Good Scents IDNot Available
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. [PubMed: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. [PubMed: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. [PubMed:6547157 ]
  4. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]

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