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Record Information
Version3.6
Creation Date2006-08-13 10:23:06 UTC
Update Date2013-05-13 23:08:44 UTC
HMDB IDHMDB04077
Secondary Accession NumbersNone
Metabolite Identification
Common Name4,6-Dihydroxyquinoline
Description4,6-Dihydroxyquinoline is the product of the conversion of 5-hydroxykynurenamine by the enzyme monoamine oxidase, both metabolites from the 5-hydroxytryptophan metabolism. (PMIDs 7160021, 312499).
Structure
Thumb
Synonyms
  1. 4,6-Quinolinediol
  2. Quinoline-4,6-diol
Chemical FormulaC9H7NO2
Average Molecular Weight161.1574
Monoisotopic Molecular Weight161.047678473
IUPAC Namequinoline-4,6-diol
Traditional Namequinoline-4,6-diol
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
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassQuinolines and Derivatives
Sub ClassHydroxyquinolines
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • dihydroxyquinoline(ChEBI)
Substituents
  • Phenol
  • Phenol Derivative
  • Pyridine
Direct ParentHydroxyquinolines
Ontology
StatusExpected and 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
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 Area53.35ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.94ChemAxon
Polarizability15.8ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063map00380
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023301
KNApSAcK IDNot Available
Chemspider ID389609
KEGG Compound IDC05639
BioCyc IDNot Available
BiGG ID46176
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04077
Metagene LinkHMDB04077
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

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