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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2009-07-25 00:07:57 UTC
Update Date2021-09-14 15:20:32 UTC
HMDB IDHMDB0012819
Secondary Accession Numbers
  • HMDB12819
Metabolite Identification
Common Name5-Hydroxykynurenine
Description5-Hydroxykynurenine 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. A hydroxykynurenine that is kynurenine bearing a hydroxy group at the position 5. 5-Hydroxykynurenine is a very strong basic compound (based on its pKa). Within humans, 5-hydroxykynurenine participates in a number of enzymatic reactions. In particular, 5-hydroxykynurenine and formic acid can be biosynthesized from 5-hydroxy-N-formylkynurenine; which is mediated by the enzyme kynurenine formamidase. In addition, 5-hydroxykynurenine can be converted into 5-hydroxykynurenamine; which is mediated by the enzyme aromatic-L-amino-acid decarboxylase. In humans, 5-hydroxykynurenine is involved in tryptophan metabolism.
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)-isomerHMDB
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
Description 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
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
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
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 IDFDB029180
KNApSAcK IDNot Available
Chemspider ID389616
KEGG Compound IDC05651
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-Hydroxykynurenine
METLIN IDNot Available
PubChem Compound440745
PDB IDNot Available
ChEBI ID2076
Food Biomarker OntologyNot Available
VMH ID5HXKYN
MarkerDB IDNot Available
Good Scents IDNot Available
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