Showing metabocard for 4,6-Dihydroxyquinoline (BMDB0004077)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:07:42 UTC
Update Date2020-05-21 16:28:50 UTC
BMDB IDBMDB0004077
Secondary Accession Numbers
  • BMDB04077
Metabolite Identification
Common Name4,6-Dihydroxyquinoline
Description4,6-Dihydroxyquinoline, also known as 4,6-dihydroxyquinoline, belongs to the class of organic compounds known as hydroxyquinolones. Hydroxyquinolones are compounds containing a quinoline moiety bearing a hydroxyl group and a ketone. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine. 4,6-Dihydroxyquinoline is possibly soluble (in water) and a moderately basic compound (based on its pKa). 4,6-Dihydroxyquinoline exists in all living organisms, ranging from bacteria to humans. 4,6-Dihydroxyquinoline can be biosynthesized from 5-hydroxykynurenamine through its interaction with the enzyme kynurenine 3-monooxygenase. In cattle, 4,6-dihydroxyquinoline is involved in the metabolic pathway called the tryptophan metabolism pathway.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
6-Hydroxy-1H-quinolin-4-oneChEBI
Quinoline-4,6-diolKegg
4,6-QuinolinediolHMDB
Chemical FormulaC9H7NO2
Average Molecular Weight161.1574
Monoisotopic Molecular Weight161.047678473
IUPAC Namequinoline-4,6-diol
Traditional Name4,6-dihydroxyquinoline
CAS Registry Number3517-61-1
SMILES
OC1=CC2=C(O)C=CN=C2C=C1
InChI Identifier
InChI=1S/C9H7NO2/c11-6-1-2-8-7(5-6)9(12)3-4-10-8/h1-5,11H,(H,10,12)
InChI KeyXFALURCRIGINGT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxyquinolones. Hydroxyquinolones are compounds containing a quinoline moiety bearing a hydroxyl group and a ketone. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinolones and derivatives
Direct ParentHydroxyquinolones
Alternative Parents
Substituents
  • Hydroxyquinolone
  • Dihydroquinolone
  • Hydroxyquinoline
  • Dihydroquinoline
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous amide
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.09ALOGPS
logP1.52ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)9.51ChemAxon
pKa (Strongest Basic)2.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.35 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.94 m³·mol⁻¹ChemAxon
Polarizability15.8 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, Positivesplash10-01q9-0900000000-5a26ca29602b82b947ecView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ec-4190000000-4bb8d953c5850dd96f48View 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, Positivesplash10-03di-0900000000-2b4e8673d9953857188dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-664352c4cf4241c0a1c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-2900000000-05e37aff72635356f2ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-34a29a4deafcb0ad7c33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-06fb975c74de0f90f723View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-0900000000-39deb8142073ba5b68aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-d2b094746088a17847e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-d9bf4aaec04c4b90185aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0159-4900000000-d7445a5c12b24666d75aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-29ea448bd0cee5fb98dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-02e9863a91ed972b84ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-5900000000-f7f1ae1acee5ecfdcc35View 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 Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0004077
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023301
KNApSAcK IDC00055687
Chemspider ID389609
KEGG Compound IDC05639
BioCyc IDNot Available
BiGG ID46176
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440738
PDB IDNot Available
ChEBI ID28799
References
Synthesis ReferenceNoguchi, Tomoo; Kaseda, Hiroki; Kido, Ryo; Matsumura, Yuichi. 5-Hydroxykynurenine decarboxylase in rat intestine. Journal of Biochemistry (Tokyo, Japan) (1970), 67(1), 113-21.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Kynurenine 3-monooxygenase
General function:
Not Available
Specific function:
Not Available
Gene Name:
KMO
Uniprot ID:
E1BN59
Molecular weight:
51032.0
Reactions
5-Hydroxykynurenamine + NADPH + Oxygen → 4,6-Dihydroxyquinoline + NADP + Waterdetails