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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-01-30 14:47:12 UTC
Update Date2021-09-14 15:20:32 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
Data?1582752931
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
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
  • L-alpha-amino acid
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • O-aminophenol
  • Gamma-keto acid
  • Aminophenol
  • Aniline or substituted anilines
  • Aryl alkyl ketone
  • Benzoyl
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Keto acid
  • Beta-aminoketone
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous amide
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.33 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.03 m³·mol⁻¹ChemAxon
Polarizability21.67 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available152.09131661259
DarkChem[M-H]-PredictedNot Available150.7631661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
L-3-Hydroxykynurenine,1TMS,#12341.4836https://arxiv.org/abs/1905.12712
L-3-Hydroxykynurenine,1TMS,#22305.193https://arxiv.org/abs/1905.12712
L-3-Hydroxykynurenine,1TMS,#32355.8486https://arxiv.org/abs/1905.12712
L-3-Hydroxykynurenine,1TMS,#42395.2537https://arxiv.org/abs/1905.12712
L-3-Hydroxykynurenine,2TMS,#12300.65https://arxiv.org/abs/1905.12712
L-3-Hydroxykynurenine,2TMS,#22346.059https://arxiv.org/abs/1905.12712
L-3-Hydroxykynurenine,2TMS,#32414.4346https://arxiv.org/abs/1905.12712
L-3-Hydroxykynurenine,2TMS,#42314.537https://arxiv.org/abs/1905.12712
L-3-Hydroxykynurenine,2TMS,#52341.392https://arxiv.org/abs/1905.12712
L-3-Hydroxykynurenine,2TMS,#62376.4978https://arxiv.org/abs/1905.12712
L-3-Hydroxykynurenine,2TMS,#72516.2537https://arxiv.org/abs/1905.12712
L-3-Hydroxykynurenine,2TMS,#82387.8354https://arxiv.org/abs/1905.12712
L-3-Hydroxykynurenine,1TBDMS,#12612.3672https://arxiv.org/abs/1905.12712
L-3-Hydroxykynurenine,1TBDMS,#22593.6335https://arxiv.org/abs/1905.12712
L-3-Hydroxykynurenine,1TBDMS,#32611.8076https://arxiv.org/abs/1905.12712
L-3-Hydroxykynurenine,1TBDMS,#42665.6997https://arxiv.org/abs/1905.12712
L-3-Hydroxykynurenine,2TBDMS,#12809.289https://arxiv.org/abs/1905.12712
L-3-Hydroxykynurenine,2TBDMS,#22855.8037https://arxiv.org/abs/1905.12712
L-3-Hydroxykynurenine,2TBDMS,#32894.8809https://arxiv.org/abs/1905.12712
L-3-Hydroxykynurenine,2TBDMS,#42819.7144https://arxiv.org/abs/1905.12712
L-3-Hydroxykynurenine,2TBDMS,#52843.231https://arxiv.org/abs/1905.12712
L-3-Hydroxykynurenine,2TBDMS,#62888.0757https://arxiv.org/abs/1905.12712
L-3-Hydroxykynurenine,2TBDMS,#72956.6853https://arxiv.org/abs/1905.12712
L-3-Hydroxykynurenine,2TBDMS,#82844.5977https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-057u-7910000000-88ad37433d9fe2009b5e2016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0596-8379000000-0b0a9595aae2502a55ac2017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0960000000-c33d63911a63b0e550592016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0209-2900000000-733debea97f59a15a6202016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-6900000000-908957a56bc62255065a2016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1290000000-49db02e2f97330c6041f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9650000000-45bd0384724255104d6c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-7900000000-e62c0de8b7c63b9e40662016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0890000000-24d8093dfa7cd74719592021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-070i-1900000000-3159845d0fd09fc5476c2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9700000000-c823da7e7ec85255fba02021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ab9-0690000000-e55cff3d90188bbe1b4f2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1910000000-15ef15dcef2ce9fdfef52021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6900000000-2b99b24490fd7fc7a3f92021-09-08View Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.2 (1.0-3.4) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0984 uMInfant (0-1 year old)FemaleNicotinamide Adenine Dinucleotide Deficiency details
Associated Disorders and Diseases
Disease References
Nicotinamide Adenine Dinucleotide Deficiency
  1. Shi H, Enriquez A, Rapadas M, Martin EMMA, Wang R, Moreau J, Lim CK, Szot JO, Ip E, Hughes JN, Sugimoto K, Humphreys DT, McInerney-Leo AM, Leo PJ, Maghzal GJ, Halliday J, Smith J, Colley A, Mark PR, Collins F, Sillence DO, Winlaw DS, Ho JWK, Guillemin GJ, Brown MA, Kikuchi K, Thomas PQ, Stocker R, Giannoulatou E, Chapman G, Duncan EL, Sparrow DB, Dunwoodie SL: NAD Deficiency, Congenital Malformations, and Niacin Supplementation. N Engl J Med. 2017 Aug 10;377(6):544-552. doi: 10.1056/NEJMoa1616361. [PubMed:28792876 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028330
KNApSAcK IDC00007443
Chemspider ID11318
KEGG Compound IDC03227
BioCyc ID3-HYDROXY-L-KYNURENINE
BiGG IDNot Available
Wikipedia Link3-Hydroxykynurenine
METLIN IDNot Available
PubChem Compound11811
PDB ID3DJ
ChEBI ID17380
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
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