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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:11 UTC
HMDB IDHMDB00684
Secondary Accession Numbers
  • HMDB00183
Metabolite Identification
Common NameL-Kynurenine
DescriptionKynurenine is a metabolite of the amino acid tryptophan used in the production of niacin. L-kynurenine is a central compound of the pathway of tryptophan metabolism pathway since it can change to the neuroprotective agent kynurenic acid or to the neurotoxic agent quinolinic acid. The break-up of these endogenous compounds' balance can be observable in many disorders. It can occur in neurodegenerative disorders, such as Parkinson's disease, Huntington's and Alzheimer's disease, in stroke, in epilepsy, in multiple sclerosis, in amyotrophic lateral sclerosis, and in mental failures, such as schizophrenia and depression.
Structure
Thumb
Synonyms
ValueSource
3-Anthraniloyl-L-alanineKegg
(AlphaS)-alpha,2-diamino-3-hydroxy-gamma-oxo-benzenebutanoateHMDB
(AlphaS)-alpha,2-diamino-3-hydroxy-gamma-oxo-benzenebutanoic acidHMDB
(S)-alpha,2-diamino-3-Hydroxy-gamma-oxo-benzenebutanoateHMDB
(S)-alpha,2-diamino-3-Hydroxy-gamma-oxo-benzenebutanoic acidHMDB
3-(3-Hydroxyanthraniloyl)-L-alanineHMDB
3-Anthraniloyl-alanineHMDB
3-AnthraniloylalanineHMDB
3-Hydroxy-L-kynurenineHMDB
alpha,2-diamino-gamma-oxo-BenzenebutanoateHMDB
alpha,2-diamino-gamma-oxo-Benzenebutanoic acidHMDB
DL-KynurenineHMDB
DL-Kynureninefree baseHMDB
KynureninHMDB
KynurenineHMDB
QuinurenineHMDB
Chemical FormulaC10H12N2O3
Average Molecular Weight208.2139
Monoisotopic Molecular Weight208.08479226
IUPAC Name(2S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid
Traditional NameL-kynurenine
CAS Registry Number343-65-7
SMILES
N[C@@H](CC(=O)C1=CC=CC=C1N)C(O)=O
InChI Identifier
InChI=1S/C10H12N2O3/c11-7-4-2-1-3-6(7)9(13)5-8(12)10(14)15/h1-4,8H,5,11-12H2,(H,14,15)/t8-/m0/s1
InChI KeyInChIKey=YGPSJZOEDVAXAB-QMMMGPOBSA-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
  • L-alpha-amino acid
  • Phenylpropylamine
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Acetophenone
  • Substituted aniline
  • Aryl alkyl ketone
  • Aryl ketone
  • Gamma-keto acid
  • Benzoyl
  • 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 Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Tryptophan metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point191 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.67 mg/mLALOGPS
logP-1.9ALOGPS
logP-1.9ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.19ChemAxon
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area106.41 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity55.05 m3·mol-1ChemAxon
Polarizability20.59 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-014l-0931000000-29fa7c323b035cb399d3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-2910000000-366ce08b5736d68dfad0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01bd-5900000000-c18e10be7e029474cf03View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00kf-9300000000-0f8238d38819f6f30d12View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0a4i-0790000000-3fa45266412288bf1c62View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0007-3900000000-a66f45aff81960af7575View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00xv-5900000000-15442ec5aaef005401aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00r7-7900000000-0833fe9d2739d329f197View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9400000000-d5d45364462a730de436View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0006-0900000000-13929f0bde71b6326d3fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0f6w-2900000000-b2d4f361ffee9fd93bb7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-004j-0900000000-96930a886f7bbcc44df3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-2441a358973abdb063daView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0udi-0900000000-dc4fee4751d629575157View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Brain
  • Central Nervous System
  • Epidermis
  • Fibroblasts
  • Intestine
  • Liver
  • Neuron
  • Placenta
  • Spleen
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063map00380
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.6 +/- 0.1 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.4 (0.7-3.0) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified2.4 +/- 0.5 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0019 +/- 0.00021 umol/mmol creatinineAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.052 +/- 0.0031 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.054 +/- 0.007 uMAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.7503 +/- 0.3831 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.41 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.85 +/- 1.94 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified1.7 (1.1-2.5) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.41 (0.08-1.31) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.56 +/- 0.91 umol/mmol creatinineInfant (0-1 year old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.18 +/- 0.040 uMAdult (>18 years old)Not SpecifiedHydrocephalus details
Cerebrospinal Fluid (CSF)Detected and Quantified0.25 +/- 0.12 uMAdult (>18 years old)Not SpecifiedIntraventricular hemorrhage details
Cerebrospinal Fluid (CSF)Detected and Quantified1.6 +/- 0.58 uMAdult (>18 years old)Not SpecifiedCNS Tumors details
Cerebrospinal Fluid (CSF)Detected and Quantified2.6 +/- 1.06 uMAdult (>18 years old)Not SpecifiedCNS Infections details
UrineDetected and Quantified0.7154 +/- 0.8277 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.6012 +/- 0.6597 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
CNS infections
  1. Heyes MP, Saito K, Milstien S, Schiff SJ: Quinolinic acid in tumors, hemorrhage and bacterial infections of the central nervous system in children. J Neurol Sci. 1995 Nov;133(1-2):112-8. [8583213 ]
CNS tumors
  1. Heyes MP, Saito K, Milstien S, Schiff SJ: Quinolinic acid in tumors, hemorrhage and bacterial infections of the central nervous system in children. J Neurol Sci. 1995 Nov;133(1-2):112-8. [8583213 ]
Hydrocephalus
  1. Heyes MP, Saito K, Milstien S, Schiff SJ: Quinolinic acid in tumors, hemorrhage and bacterial infections of the central nervous system in children. J Neurol Sci. 1995 Nov;133(1-2):112-8. [8583213 ]
Intraventricular hemorrhage
  1. Heyes MP, Saito K, Milstien S, Schiff SJ: Quinolinic acid in tumors, hemorrhage and bacterial infections of the central nervous system in children. J Neurol Sci. 1995 Nov;133(1-2):112-8. [8583213 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022181
KNApSAcK IDNot Available
Chemspider ID141580
KEGG Compound IDC00328
BioCyc IDL-KYNURENINE
BiGG ID1445574
Wikipedia LinkKynurenine
NuGOwiki LinkHMDB00684
Metagene LinkHMDB00684
METLIN ID72
PubChem Compound161166
PDB IDKYN
ChEBI ID16946
References
Synthesis ReferenceHayaishi, Osamu. L-Kynurenine sulfate monohydrate. Biochemical Preparations (1953), 3 108-11.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Medana IM, Day NP, Salahifar-Sabet H, Stocker R, Smythe G, Bwanaisa L, Njobvu A, Kayira K, Turner GD, Taylor TE, Hunt NH: Metabolites of the kynurenine pathway of tryptophan metabolism in the cerebrospinal fluid of Malawian children with malaria. J Infect Dis. 2003 Sep 15;188(6):844-9. Epub 2003 Sep 9. [12964115 ]
  2. Widner B, Sepp N, Kowald E, Ortner U, Wirleitner B, Fritsch P, Baier-Bitterlich G, Fuchs D: Enhanced tryptophan degradation in systemic lupus erythematosus. Immunobiology. 2000 Apr;201(5):621-30. [10834318 ]
  3. Widner B, Sepp N, Kowald E, Kind S, Schmuth M, Fuchs D: Degradation of tryptophan in patients with systemic lupus erythematosus. Adv Exp Med Biol. 1999;467:571-7. [10721102 ]
  4. Joseph MH: Determination of kynurenine by a simple gas-liquid chromatographic method applicable to urine, plasma, brain and cerebrospinal fluid. J Chromatogr. 1978 Jul 1;146(1):33-41. [670356 ]
  5. Heyes MP, Saito K, Lackner A, Wiley CA, Achim CL, Markey SP: Sources of the neurotoxin quinolinic acid in the brain of HIV-1-infected patients and retrovirus-infected macaques. FASEB J. 1998 Jul;12(10):881-96. [9657528 ]
  6. Fujigaki S, Saito K, Takemura M, Fujii H, Wada H, Noma A, Seishima M: Species differences in L-tryptophan-kynurenine pathway metabolism: quantification of anthranilic acid and its related enzymes. Arch Biochem Biophys. 1998 Oct 15;358(2):329-35. [9784247 ]
  7. Widner B, Werner ER, Schennach H, Fuchs D: An HPLC method to determine tryptophan and kynurenine in serum simultaneously. Adv Exp Med Biol. 1999;467:827-32. [10721136 ]
  8. Saito K, Fujigaki S, Heyes MP, Shibata K, Takemura M, Fujii H, Wada H, Noma A, Seishima M: Mechanism of increases in L-kynurenine and quinolinic acid in renal insufficiency. Am J Physiol Renal Physiol. 2000 Sep;279(3):F565-72. [10966936 ]
  9. Heyes MP, Saito K, Milstien S, Schiff SJ: Quinolinic acid in tumors, hemorrhage and bacterial infections of the central nervous system in children. J Neurol Sci. 1995 Nov;133(1-2):112-8. [8583213 ]
  10. Martinsons A, Rudzite V, Groma V, Bratslavska O, Widner B, Fuchs D: Kynurenine and neopterin in chronic glomerulonephritis. Adv Exp Med Biol. 1999;467:579-86. [10721103 ]
  11. Heyes MP, Saito K, Crowley JS, Davis LE, Demitrack MA, Der M, Dilling LA, Elia J, Kruesi MJ, Lackner A, et al.: Quinolinic acid and kynurenine pathway metabolism in inflammatory and non-inflammatory neurological disease. Brain. 1992 Oct;115 ( Pt 5):1249-73. [1422788 ]
  12. Moroni F, Carpenedo R, Chiarugi A: Kynurenine hydroxylase and kynureninase inhibitors as tools to study the role of kynurenine metabolites in the central nervous system. Adv Exp Med Biol. 1996;398:203-10. [8906267 ]
  13. Calandra P: Research on tryptophan metabolites "via kynurenine" in epidermis of man and mouse. Acta Vitaminol Enzymol. 1975;29(1-6):158-60. [1244085 ]
  14. Manuelpillai U, Nicholls T, Wallace EM, Phillips DJ, Guillemin G, Walker D: Increased mRNA expression of kynurenine pathway enzymes in human placentae exposed to bacterial endotoxin. Adv Exp Med Biol. 2003;527:85-9. [15206719 ]
  15. Greengard O: Relationship between urinary excretion of kynurenine and liver tryptophan oxygenase activity. Am J Clin Nutr. 1971 Jun;24(6):709-11. [5581008 ]
  16. Heinmets F: Computer simulation and analysis of tryptophan metabolism via kynurenine pathway in liver. Comput Biol Med. 1974 Sep;1(4):323-36. [4600391 ]
  17. Okuno E, Nakamura M, Schwarcz R: Two kynurenine aminotransferases in human brain. Brain Res. 1991 Mar 1;542(2):307-12. [2029638 ]
  18. Altman K, Greengard O: Correlation of kynurenine excretion with liver tryptophan pyrrolase levels in disease and after hydrocortisone induction. J Clin Invest. 1966 Oct;45(10):1527-34. [5925511 ]
  19. Pearson SJ, Meldrum A, Reynolds GP: An investigation of the activities of 3-hydroxykynureninase and kynurenine aminotransferase in the brain in Huntington's disease. J Neural Transm Gen Sect. 1995;102(1):67-73. [8785025 ]
  20. Hartai Z, Klivenyi P, Janaky T, Penke B, Dux L, Vecsei L: Kynurenine metabolism in plasma and in red blood cells in Parkinson's disease. J Neurol Sci. 2005 Dec 15;239(1):31-5. Epub 2005 Aug 15. [16099471 ]

Enzymes

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). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:
GOT2
Uniprot ID:
P00505
Molecular weight:
47517.285
Reactions
L-Kynurenine + Oxoglutaric acid → 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + L-Glutamic aciddetails
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-Kynurenine + Water → 2-Aminobenzoic 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-Kynurenine + Oxoglutaric acid → 4-(2-Aminophenyl)-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-Kynurenine + Oxoglutaric acid → 4-(2-Aminophenyl)-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:
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
Reactions
L-Formylkynurenine + Water → Formic acid + L-Kynureninedetails
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-Kynurenine + Oxoglutaric acid → 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + L-Glutamic aciddetails
L-Kynurenine + Glyoxylic acid → 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + Glycinedetails