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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-08 10:45:44 UTC
Update Date2020-06-16 19:12:19 UTC
HMDB IDHMDB0006779
Secondary Accession Numbers
  • HMDB06779
Metabolite Identification
Common NameIndole-5,6-quinone
DescriptionIndole-5,6-quinone belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Indole-5,6-quinone exists in all living organisms, ranging from bacteria to humans. In humans, indole-5,6-quinone is involved in the metabolic disorder called hawkinsinuria. Indole-5,6-quinone has been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), and milk (cow). This could make indole-5,6-quinone a potential biomarker for the consumption of these foods. Indole-5,6-quinone is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Indole-5,6-quinone.
Structure
Data?1588791369
Synonyms
ValueSource
1H-Indole-5,6-dioneHMDB
Indole-5,6 quinoneHMDB
Chemical FormulaC8H5NO2
Average Molecular Weight147.1308
Monoisotopic Molecular Weight147.032028409
IUPAC Name5,6-dihydro-1H-indole-5,6-dione
Traditional Nameindole-5,6-quinone
CAS Registry Number582-59-2
SMILES
O=C1C=C2NC=CC2=CC1=O
InChI Identifier
InChI=1S/C8H5NO2/c10-7-3-5-1-2-9-6(5)4-8(7)11/h1-4,9H
InChI KeyIGGVVGHJSQSLFO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassNot Available
Direct ParentIndoles and derivatives
Alternative Parents
Substituents
  • Indole or derivatives
  • Pyrrole
  • Vinylogous amide
  • Heteroaromatic compound
  • Ketone
  • Cyclic ketone
  • Azacycle
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

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
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility10.5 g/LALOGPS
logP10(0.09) g/LALOGPS
logP10(0.65) g/LChemAxon
logS10(-1.2) g/LALOGPS
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.17 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.15 m³·mol⁻¹ChemAxon
Polarizability13.76 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]+131.23531661259
DarkChem[M-H]-128.32831661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Indole-5,6-quinoneO=C1C=C2NC=CC2=CC1=O2667.4Standard polar33892256
Indole-5,6-quinoneO=C1C=C2NC=CC2=CC1=O1915.4Standard non polar33892256
Indole-5,6-quinoneO=C1C=C2NC=CC2=CC1=O1887.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Indole-5,6-quinone,1TMS,isomer #1C[Si](C)(C)N1C=CC2=CC(=O)C(=O)C=C211971.1Semi standard non polar33892256
Indole-5,6-quinone,1TMS,isomer #1C[Si](C)(C)N1C=CC2=CC(=O)C(=O)C=C211836.0Standard non polar33892256
Indole-5,6-quinone,1TMS,isomer #1C[Si](C)(C)N1C=CC2=CC(=O)C(=O)C=C212604.2Standard polar33892256
Indole-5,6-quinone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=CC2=CC(=O)C(=O)C=C212189.3Semi standard non polar33892256
Indole-5,6-quinone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=CC2=CC(=O)C(=O)C=C212041.2Standard non polar33892256
Indole-5,6-quinone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=CC2=CC(=O)C(=O)C=C212764.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Indole-5,6-quinone GC-MS (Non-derivatized) - 70eV, Positivesplash10-066v-6900000000-1dca4f608ca5300164122017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indole-5,6-quinone 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 - Indole-5,6-quinone 10V, Positive-QTOFsplash10-0002-0900000000-0cf3a823a731cd4e7a642017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-5,6-quinone 20V, Positive-QTOFsplash10-00dj-0900000000-81eabafffbd73c3732d02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-5,6-quinone 40V, Positive-QTOFsplash10-004i-9400000000-a1268508f67a658cecf52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-5,6-quinone 10V, Negative-QTOFsplash10-0002-0900000000-efe9cb1e2b58b04208a12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-5,6-quinone 20V, Negative-QTOFsplash10-0002-0900000000-37f54dda461b2c0102c32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-5,6-quinone 40V, Negative-QTOFsplash10-014j-0900000000-775f13193ba5fc2154eb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-5,6-quinone 10V, Positive-QTOFsplash10-0002-0900000000-9731758a758f9f924b402021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-5,6-quinone 20V, Positive-QTOFsplash10-006t-1900000000-8e368a3b1e151aabfbfa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-5,6-quinone 40V, Positive-QTOFsplash10-0fxx-9700000000-616921cda808497b0d2c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-5,6-quinone 10V, Negative-QTOFsplash10-0002-0900000000-7c00c3e5508255ca82482021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-5,6-quinone 20V, Negative-QTOFsplash10-0002-0900000000-a13b820d1ef5510928d72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-5,6-quinone 40V, Negative-QTOFsplash10-00kb-0900000000-e18791078884a5a972e82021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart 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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024077
KNApSAcK IDNot Available
Chemspider ID389600
KEGG Compound IDC05579
BioCyc IDCPD-12373
BiGG IDNot Available
Wikipedia LinkIndole-5,6-quinone
METLIN IDNot Available
PubChem Compound440728
PDB IDNot Available
ChEBI ID27406
Food Biomarker OntologyNot Available
VMH IDM03163
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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