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Record Information
Version3.6
Creation Date2009-01-30 14:47:12 UTC
Update Date2017-09-21 23:32:48 UTC
HMDB IDHMDB0011631
Secondary Accession Numbers
  • HMDB11631
Metabolite Identification
Common NameL-3-Hydroxykynurenine
DescriptionL-3-Hydroxykynurenine (L-3-HK) is a metabolite in the kynurenine pathway, the major route of tryptophan degradation in mammals. Kynurenine 3-monooxygenase, an NADPH-dependent flavin monooxygenase, catalyses the hydroxylation of L-kynurenine to L-3-hydroxykynurenine. 3-hydroxykynurenine can be converted to 3-hydroxyanthranilate by the enzyme 3-hydroxykinureninase. It may also be converted to 4-(2-amino-3-hydroxphenyl)-2,4-dioxobutanoate by the enzyme kynurenine-oxoglutarate transaminase. L-3-Hydroxykynurenine (L-3-HK) is a known generator of highly reactive free radicals. An elevation of L-3-HK levels has been shown to constitute a significant hazard in situations of excitotoxic injury. In particular, L-3-HK may contribute to the neuronal deficits underlying HIV-associated dementia (PMID: 7830088 ). Pharmacological interventions aimed at decreasing L-3-HK formation may therefore be particularly useful for the treatment of neurological diseases which are associated with an abnormally enhanced flux through the kynurenine pathway (PMID: 10583474 ).
Structure
Thumb
Synonyms
ValueSource
(2S)-2-amino-4-(2-amino-3-Hydroxyphenyl)-4-oxobutanoic acidChEBI
3-(3-Hydroxyanthraniloyl)-L-alanineChEBI
(2S)-2-amino-4-(2-amino-3-Hydroxyphenyl)-4-oxobutanoateGenerator
3-(2-amino-3-Hydroxybenzoyl)-L-alanineHMDB
3-Hydroxy-L-kynurenineHMDB
L-3-HKHMDB
Chemical FormulaC10H12N2O4
Average Molecular Weight224.2133
Monoisotopic Molecular Weight224.079706882
IUPAC Name(2S)-2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid
Traditional Name3-hydroxy-L-kynurenine
CAS Registry Number606-14-4
SMILES
N[C@@H](CC(=O)C1=CC=CC(O)=C1N)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)/t6-/m0/s1
InChI KeyVCKPUUFAIGNJHC-LURJTMIESA-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
  • Butyrophenone
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • O-aminophenol
  • Aminophenol
  • Benzoyl
  • Aniline or substituted anilines
  • Gamma-keto acid
  • Aryl alkyl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Beta-aminoketone
  • Keto acid
  • Benzenoid
  • Primary aromatic amine
  • Vinylogous amide
  • Amino acid
  • Amino acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Primary aliphatic amine
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Primary amine
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and 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 Solubility3.33 mg/mLALOGPS
logP-2.1ALOGPS
logP-2.2ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)0.99ChemAxon
pKa (Strongest Basic)8.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area126.64 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.03 m3·mol-1ChemAxon
Polarizability21.67 Å3ChemAxon
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-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Tryptophan MetabolismPw000163Pw000163 greyscalePw000163 simpleMap00380
Displaying 1 entry
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified2.2 (1.0-3.4) umol/mmol creatinineAdult (>18 years old)BothNormal
      • Geigy Scientific ...
    details
    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 IDFDB028330
    KNApSAcK IDNot Available
    Chemspider ID11318
    KEGG Compound IDC03227
    BioCyc ID3-HYDROXY-L-KYNURENINE
    BiGG IDNot Available
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB0011631
    METLIN IDNot Available
    PubChem Compound11811
    PDB IDNot Available
    ChEBI ID17380
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Sardar AM, Bell JE, Reynolds GP: Increased concentrations of the neurotoxin 3-hydroxykynurenine in the frontal cortex of HIV-1-positive patients. J Neurochem. 1995 Feb;64(2):932-5. [PubMed:7830088 ]
    2. Guidetti P, Schwarcz R: 3-Hydroxykynurenine potentiates quinolinate but not NMDA toxicity in the rat striatum. Eur J Neurosci. 1999 Nov;11(11):3857-63. [PubMed:10583474 ]

    Enzymes

    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
    Reactions
    L-3-Hydroxykynurenine + Water → 3-Hydroxyanthranilic acid + L-Alaninedetails
    General function:
    Involved in transferase activity, transferring nitrogenous groups
    Specific function:
    Transaminase with broad substrate specificity. Has transaminase activity towards aminoadipate, kynurenine, methionine and glutamate. Shows activity also towards tryptophan, aspartate and hydroxykynurenine. Accepts a variety of oxo-acids as amino-group acceptors, with a preference for 2-oxoglutarate, 2-oxocaproic acid, phenylpyruvate and alpha-oxo-gamma-methiol butyric acid. Can also use glyoxylate as amino-group acceptor (in vitro).
    Gene Name:
    AADAT
    Uniprot ID:
    Q8N5Z0
    Molecular weight:
    47351.17
    Reactions
    L-3-Hydroxykynurenine + Oxoglutaric acid → 4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid + L-Glutamic aciddetails
    General function:
    Involved in 1-aminocyclopropane-1-carboxylate synthase activity
    Specific function:
    Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Metabolizes the cysteine conjugates of certain halogenated alkenes and alkanes to form reactive metabolites. Catalyzes the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond.
    Gene Name:
    CCBL1
    Uniprot ID:
    Q16773
    Molecular weight:
    47874.765
    Reactions
    L-3-Hydroxykynurenine + Oxoglutaric acid → 4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid + L-Glutamic aciddetails
    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
    Reactions
    L-Kynurenine + NADPH + Oxygen → L-3-Hydroxykynurenine + NADP + Waterdetails
    L-Kynurenine + Oxygen + NADPH + Hydrogen Ion → L-3-Hydroxykynurenine + NADP + Waterdetails
    General function:
    Involved in transferase activity, transferring nitrogenous groups
    Specific function:
    Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). May catalyze the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond (By similarity). Has transaminase activity towards L-kynurenine, tryptophan, phenylalanine, serine, cysteine, methionine, histidine, glutamine and asparagine with glyoxylate as an amino group acceptor (in vitro). Has lower activity with 2-oxoglutarate as amino group acceptor (in vitro) (By similarity).
    Gene Name:
    CCBL2
    Uniprot ID:
    Q6YP21
    Molecular weight:
    51399.855
    Reactions
    L-3-Hydroxykynurenine + Oxoglutaric acid → 4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid + L-Glutamic aciddetails