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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 10:23:06 UTC
Update Date2020-02-26 21:24:57 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?1582752297
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
Disposition

Source:

Biological location:

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
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 Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available133.91831661259
DarkChem[M-H]-PredictedNot Available131.82731661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
4,6-Dihydroxyquinoline,1TMS,#11869.3848https://arxiv.org/abs/1905.12712
4,6-Dihydroxyquinoline,1TMS,#21843.4673https://arxiv.org/abs/1905.12712
4,6-Dihydroxyquinoline,2TMS,#11884.2534https://arxiv.org/abs/1905.12712
4,6-Dihydroxyquinoline,1TBDMS,#12121.8452https://arxiv.org/abs/1905.12712
4,6-Dihydroxyquinoline,1TBDMS,#22115.3027https://arxiv.org/abs/1905.12712
4,6-Dihydroxyquinoline,2TBDMS,#12417.0999https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01q9-0900000000-5a26ca29602b82b947ec2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ec-4190000000-4bb8d953c5850dd96f482017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-2b4e8673d9953857188d2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-664352c4cf4241c0a1c42017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-2900000000-05e37aff72635356f2cc2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-34a29a4deafcb0ad7c332017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-06fb975c74de0f90f7232017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-0900000000-39deb8142073ba5b68ae2017-09-01View 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
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