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Record Information
Version4.0
Creation Date2006-08-13 10:22:27 UTC
Update Date2017-09-27 08:24:25 UTC
HMDB IDHMDB0004076
Secondary Accession Numbers
  • HMDB04076
Metabolite Identification
Common Name5-Hydroxykynurenamine
Description5-Hydroxykynurenamine is an intermediate in the tryptophan metabolic pathway [Kegg: C05638]. It is generated from 5-hydroxykynurenine via the enzyme DOPA decarboxylase.
Structure
Thumb
Synonyms
ValueSource
3-amino-1-(2-amino-5-Hydroxyphenyl)-1-propanoneChEBI
MausamineChEBI
MousamineChEBI
5-HydroxykynuramineHMDB
5-Hydroxykynuramine monohydrobromideMeSH
5-Hydroxykynuramine dihydrochlorideMeSH
5-Hydroxykynuramine dihydrobromideMeSH
Chemical FormulaC9H12N2O2
Average Molecular Weight180.2038
Monoisotopic Molecular Weight180.089877638
IUPAC Name3-amino-1-(2-amino-5-hydroxyphenyl)propan-1-one
Traditional Name5-hydroxykynurenamine
CAS Registry Number708-23-6
SMILES
NCCC(=O)C1=C(N)C=CC(O)=C1
InChI Identifier
InChI=1S/C9H12N2O2/c10-4-3-9(13)7-5-6(12)1-2-8(7)11/h1-2,5,12H,3-4,10-11H2
InChI KeyJANBBPTXDKFOQR-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Aminophenol
  • P-aminophenol
  • Benzoyl
  • Aryl alkyl ketone
  • Aniline or substituted anilines
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Beta-aminoketone
  • Primary aromatic amine
  • Benzenoid
  • Vinylogous amide
  • Primary amine
  • Organic oxide
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Amine
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.354Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.59 g/LALOGPS
logP-0.47ALOGPS
logP-0.13ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)10.01ChemAxon
pKa (Strongest Basic)9.34ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area89.34 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity51.2 m³·mol⁻¹ChemAxon
Polarizability18.71 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
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, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0900000000-fdcafa493a3a3738f189View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-1900000000-cc40b42cbe0bab3e9572View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aba-8900000000-b0f4a5f21f7abe4af468View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-c870ac2fb24b5478768eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-0900000000-c0a66828c2d20d72fea2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4900000000-e62241e70455598c384aView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Tryptophan MetabolismPw000163Pw000163 greyscalePw000163 simpleMap00380
Displaying 1 entry
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 IDFDB023300
KNApSAcK IDNot Available
Chemspider ID144400
KEGG Compound IDC05638
BioCyc IDNot Available
BiGG ID46174
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound164719
PDB IDNot Available
ChEBI ID28715
References
Synthesis ReferenceNot Available
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
General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:
DDC
Uniprot ID:
P20711
Molecular weight:
53893.755
Reactions
5-Hydroxykynurenamine + Carbon dioxide → 5-Hydroxykynureninedetails