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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2009-07-25 00:07:57 UTC
Update Date2018-05-20 07:04:39 UTC
HMDB IDHMDB0012819
Secondary Accession Numbers
  • HMDB12819
Metabolite Identification
Common Name5-Hydroxykynurenine
Description5-Hydroxykynurenine is found in the tryptophan metabolism pathway. It is created from 5-Hydroxy-N-formylkynurenine through the action of arylformamidase [EC:3.5.1.9]. 5-Hydroxykynurenine is then converted to 5-Hydroxykynurenamine by the action of dopa decarboxylase [EC:4.1.1.28].
Structure
Thumb
Synonyms
ValueSource
2-amino-4-(2-amino-5-Hydroxyphenyl)-4-oxobutanoic acidChEBI
2-amino-4-(2-amino-5-Hydroxyphenyl)-4-oxobutanoateGenerator
5-Hydroxy-L-kynurenineHMDB
5-Hydroxykynurenine, (L)-isomerMeSH
Chemical FormulaC10H12N2O4
Average Molecular Weight224.2133
Monoisotopic Molecular Weight224.079706882
IUPAC Name2-amino-4-(2-amino-5-hydroxyphenyl)-4-oxobutanoic acid
Traditional Name5-hydroxykynurenine
CAS Registry Number720-00-3
SMILES
NC(CC(=O)C1=C(N)C=CC(O)=C1)C(O)=O
InChI Identifier
InChI=1S/C10H12N2O4/c11-7-2-1-5(13)3-6(7)9(14)4-8(12)10(15)16/h1-3,8,13H,4,11-12H2,(H,15,16)
InChI KeyOTDQYOVYQQZAJL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Butyrophenone
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • P-aminophenol
  • Aminophenol
  • Benzoyl
  • Gamma-keto acid
  • Aryl alkyl ketone
  • Aniline or substituted anilines
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Beta-aminoketone
  • Keto acid
  • Vinylogous amide
  • Amino acid
  • Amino acid or derivatives
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic oxide
  • Amine
  • Organonitrogen compound
  • Primary amine
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Process

Naturally occurring process:

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 Solubility3.12 g/LALOGPS
logP-2.2ALOGPS
logP-2.2ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)0.98ChemAxon
pKa (Strongest Basic)8.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area126.64 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.03 m³·mol⁻¹ChemAxon
Polarizability21.53 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, Positivesplash10-000i-2900000000-759106525958c7559c0eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9167000000-abb2f436c993df4c1d30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0890000000-dfa042db46858117582cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03mr-2900000000-c8e51ba13da85857d00bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-5900000000-a8fdd6f4771588adc784View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1090000000-1b6f8b69fc5d1440121fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-9560000000-3a0c724edce767136c71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-6900000000-43fed4337f093b9e8e92View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Children (6 - 18 years old)Bothenthesitis-related arthritis details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID389616
KEGG Compound IDC05651
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440745
PDB IDNot Available
ChEBI ID2076
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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
General function:
Involved in hydrolase activity
Specific function:
Catalyzes the hydrolysis of N-formyl-L-kynurenine to L-kynurenine, the second step in the kynurenine pathway of tryptophan degradation. Kynurenine may be further oxidized to nicotinic acid, NAD(H) and NADP(H). Required for elimination of toxic metabolites (By similarity).
Gene Name:
AFMID
Uniprot ID:
Q63HM1
Molecular weight:
33991.5
Reactions
5-Hydroxy-N-formylkynurenine + Water → 5-Hydroxykynurenine + Formic aciddetails