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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:20:02 UTC
HMDB IDHMDB0000732
Secondary Accession Numbers
  • HMDB0001152
  • HMDB00732
  • HMDB01152
Metabolite Identification
Common NameHydroxykynurenine
DescriptionHydroxykynurenine, also known as OH-kynurenine, 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. Hydroxykynurenine is a very strong basic compound (based on its pKa). In humans, hydroxykynurenine is involved in tryptophan metabolism.
Structure
Thumb
Synonyms
ValueSource
2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acidChEBI
3-(3-Hydroxyanthraniloyl)alanineChEBI
3-Hydroxy-DL-kynurenineChEBI
2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoateGenerator
3-(3-Hydroxyanthraniloyl)-alanineHMDB
3-Hydroxy-kynurenineHMDB
3-HydroxykynurenineHMDB
DL-3-HydroxykynurenineHMDB
HydroxykinurenineHMDB
OH-KynurenineHMDB
3-Hydroxykynurenine, (DL)-isomerHMDB
3-Hydroxykynurenine, (D)-isomerHMDB
3-Hydroxykynurenine, (L)-isomerHMDB
Chemical FormulaC10H12N2O4
Average Molecular Weight224.2133
Monoisotopic Molecular Weight224.079706882
IUPAC Name2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid
Traditional Namehydroxykynurenine
CAS Registry Number484-78-6
SMILES
NC(CC(=O)C1=C(N)C(O)=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C10H12N2O4/c11-6(10(15)16)4-8(14)5-2-1-3-7(13)9(5)12/h1-3,6,13H,4,11-12H2,(H,15,16)
InChI KeyVCKPUUFAIGNJHC-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
  • Gamma-keto acid
  • O-aminophenol
  • Aryl alkyl ketone
  • Aniline or substituted anilines
  • Benzoyl
  • Aminophenol
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Keto acid
  • Beta-aminoketone
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous amide
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Amine
  • Primary aliphatic amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point217 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available151.367http://allccs.zhulab.cn/database/detail?ID=AllCCS00001841
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Brain
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.05 (0.00-0.10) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.77 (0.46-5.13) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified0.15 (0.06-0.34) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022210
KNApSAcK IDNot Available
Chemspider ID87
KEGG Compound IDC02794
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-Hydroxykynurenine
METLIN ID5700
PubChem Compound89
PDB IDNot Available
ChEBI ID1547
Food Biomarker OntologyNot Available
VMH IDHLKYNR
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceKotake, Munio; Sakan, Takeo; Senoh, Shiro. Amino acids. IV. The synthesis of 3-hydroxykynurenine. J. Inst. Polytech., Osaka. City Univ. (1950), 1(No. 2), 35-41. CAN 46:2639 AN 1952:2639
Material Safety Data Sheet (MSDS)Not Available
General References

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
General function:
Involved in metabolic process
Specific function:
Catalyzes the cleavage of L-kynurenine (L-Kyn) and L-3-hydroxykynurenine (L-3OHKyn) into anthranilic acid (AA) and 3-hydroxyanthranilic acid (3-OHAA), respectively. Has a preference for the L-3-hydroxy form. Also has cysteine-conjugate-beta-lyase activity.
Gene Name:
KYNU
Uniprot ID:
Q16719
Molecular weight:
34634.47
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the hydroxylation of L-kynurenine (L-Kyn) to form 3-hydroxy-L-kynurenine (L-3OHKyn). Required for synthesis of quinolinic acid, a neurotoxic NMDA receptor antagonist and potential endogenous inhibitor of NMDA receptor signaling in axonal targeting, synaptogenesis and apoptosis during brain development. Quinolinic acid may also affect NMDA receptor signaling in pancreatic beta cells, osteoblasts, myocardial cells, and the gastrointestinal tract.
Gene Name:
KMO
Uniprot ID:
O15229
Molecular weight:
55809.445
General function:
Transcription
Specific function:
Not Available
Gene Name:
AADAT
Uniprot ID:
Q4W5N8
Molecular weight:
47351.2
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