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Record Information
Version3.6
Creation Date2009-07-25 00:07:57 UTC
Update Date2016-02-11 01:25:14 UTC
HMDB IDHMDB12819
Secondary Accession NumbersNone
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
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 KeyInChIKey=OTDQYOVYQQZAJL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as butyrophenones. These are compounds containing 1-phenylbutan-1-one moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassButyrophenones
Direct ParentButyrophenones
Alternative Parents
Substituents
  • Butyrophenone
  • Phenylpropylamine
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Acetophenone
  • Substituted aniline
  • Aryl alkyl ketone
  • Aryl ketone
  • Gamma-keto acid
  • Benzoyl
  • Aminophenol
  • Phenol
  • Aniline
  • Amino fatty acid
  • Fatty acyl
  • Primary aromatic amine
  • Keto acid
  • Beta-aminoketone
  • Vinylogous amide
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.03 m3·mol-1ChemAxon
Polarizability21.53 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID389616
KEGG Compound IDC05651
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12819
Metagene LinkHMDB12819
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