Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 10:23:06 UTC
Update Date2023-02-21 17:16:54 UTC
HMDB IDHMDB0004077
Secondary Accession Numbers
  • HMDB04077
Metabolite Identification
Common Name4,6-Dihydroxyquinoline
Description4,6-Dihydroxyquinoline, also known as quinoline-4,6-diol, 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 exists in all living organisms, ranging from bacteria to humans. In humans, 4,6-dihydroxyquinoline is involved in the tryptophan metabolism pathway. 4,6-Dihydroxyquinoline has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 4,6-dihydroxyquinoline a potential biomarker for the consumption of these foods. 4,6-Dihydroxyquinoline 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 4,6-Dihydroxyquinoline.
Structure
Data?1676999814
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
Physiological effectNot Available
Disposition
Process
RoleNot Available
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 Solubility3.96 g/LALOGPS
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.91831661259
DarkChem[M-H]-131.82731661259
DeepCCS[M+H]+131.69330932474
DeepCCS[M-H]-128.94330932474
DeepCCS[M-2H]-165.130932474
DeepCCS[M+Na]+140.49730932474
AllCCS[M+H]+132.632859911
AllCCS[M+H-H2O]+127.932859911
AllCCS[M+NH4]+137.032859911
AllCCS[M+Na]+138.332859911
AllCCS[M-H]-130.732859911
AllCCS[M+Na-2H]-131.232859911
AllCCS[M+HCOO]-131.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4,6-DihydroxyquinolineOC1=CC2=C(O)C=CN=C2C=C12876.0Standard polar33892256
4,6-DihydroxyquinolineOC1=CC2=C(O)C=CN=C2C=C11898.8Standard non polar33892256
4,6-DihydroxyquinolineOC1=CC2=C(O)C=CN=C2C=C11936.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4,6-Dihydroxyquinoline,1TMS,isomer #1C[Si](C)(C)OC1=CC=C2N=CC=C(O)C2=C11869.4Semi standard non polar33892256
4,6-Dihydroxyquinoline,1TMS,isomer #2C[Si](C)(C)OC1=CC=NC2=CC=C(O)C=C121843.5Semi standard non polar33892256
4,6-Dihydroxyquinoline,2TMS,isomer #1C[Si](C)(C)OC1=CC=C2N=CC=C(O[Si](C)(C)C)C2=C11884.3Semi standard non polar33892256
4,6-Dihydroxyquinoline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2N=CC=C(O)C2=C12121.8Semi standard non polar33892256
4,6-Dihydroxyquinoline,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=NC2=CC=C(O)C=C122115.3Semi standard non polar33892256
4,6-Dihydroxyquinoline,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2N=CC=C(O[Si](C)(C)C(C)(C)C)C2=C12417.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4,6-Dihydroxyquinoline GC-MS (Non-derivatized) - 70eV, Positivesplash10-01q9-0900000000-5a26ca29602b82b947ec2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,6-Dihydroxyquinoline GC-MS (2 TMS) - 70eV, Positivesplash10-00ec-4190000000-4bb8d953c5850dd96f482017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,6-Dihydroxyquinoline 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 - 4,6-Dihydroxyquinoline 10V, Positive-QTOFsplash10-03di-0900000000-2b4e8673d9953857188d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,6-Dihydroxyquinoline 20V, Positive-QTOFsplash10-03di-0900000000-664352c4cf4241c0a1c42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,6-Dihydroxyquinoline 40V, Positive-QTOFsplash10-053r-2900000000-05e37aff72635356f2cc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,6-Dihydroxyquinoline 10V, Negative-QTOFsplash10-03di-0900000000-34a29a4deafcb0ad7c332017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,6-Dihydroxyquinoline 20V, Negative-QTOFsplash10-03di-0900000000-06fb975c74de0f90f7232017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,6-Dihydroxyquinoline 40V, Negative-QTOFsplash10-053r-0900000000-39deb8142073ba5b68ae2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,6-Dihydroxyquinoline 10V, Positive-QTOFsplash10-03di-0900000000-d2b094746088a17847e12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,6-Dihydroxyquinoline 20V, Positive-QTOFsplash10-03di-0900000000-d9bf4aaec04c4b90185a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,6-Dihydroxyquinoline 40V, Positive-QTOFsplash10-0159-4900000000-d7445a5c12b24666d75a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,6-Dihydroxyquinoline 10V, Negative-QTOFsplash10-03di-0900000000-29ea448bd0cee5fb98df2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,6-Dihydroxyquinoline 20V, Negative-QTOFsplash10-03di-0900000000-02e9863a91ed972b84eb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,6-Dihydroxyquinoline 40V, Negative-QTOFsplash10-053r-5900000000-f7f1ae1acee5ecfdcc352021-09-22Wishart 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

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothEnthesitis-related arthritis details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH ID46DHOXQUIN
MarkerDB IDNot Available
Good Scents IDNot Available
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

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
Reactions
5-Hydroxykynurenamine + Water + Oxygen → 4,6-Dihydroxyquinoline + Ammonia + Hydrogen peroxide + Waterdetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
Reactions
5-Hydroxykynurenamine + Water + Oxygen → 4,6-Dihydroxyquinoline + Ammonia + Hydrogen peroxide + Waterdetails