Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110620
Identification
Name: L-kynurenine
Description:Zwitterionic form of L-kynurenine arising from transfer of a proton from the carboxy to the amino group; major species at pH 7.3.
Structure
Thumb
Synonyms:
  • kynurenine
Chemical Formula: C10H12N2O3
Average Molecular Weight: 208.22
Monoisotopic Molecular Weight: 209.092617294
InChI Key: YGPSJZOEDVAXAB-QMMMGPOBSA-N
InChI: 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
CAS number: 343-65-7
IUPAC Name:(2S)-4-(2-aminophenyl)-2-azaniumyl-4-oxobutanoate
Traditional IUPAC Name: L-kynurenine
SMILES:C(=O)([O-])C([N+])CC(=O)C1(=C(N)C=CC=C1)
Chemical Taxonomy
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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic oxygen compounds
Sub ClassOrganooxygen compounds
Direct Parent Alkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Butyrophenone
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Benzoyl
  • Gamma-keto acid
  • Aniline or substituted anilines
  • Aryl alkyl ketone
  • Monocyclic benzene moiety
  • Beta-aminoketone
  • Keto acid
  • Primary aromatic amine
  • Benzenoid
  • Vinylogous amide
  • Amino acid
  • Amino acid or derivatives
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Primary aliphatic amine
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organonitrogen compound
  • Primary amine
  • Aromatic homomonocyclic compound
Molecular Framework Aromatic homomonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 191 °C
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
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
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
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
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • Calandra P: Research on tryptophan metabolites "via kynurenine" in epidermis of man and mouse. Acta Vitaminol Enzymol. 1975;29(1-6):158-60. [1244085 ]
  • 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 ]
  • Greengard O: Relationship between urinary excretion of kynurenine and liver tryptophan oxygenase activity. Am J Clin Nutr. 1971 Jun;24(6):709-11. [5581008 ]
  • Heinmets F: Computer simulation and analysis of tryptophan metabolism via kynurenine pathway in liver. Comput Biol Med. 1974 Sep;1(4):323-36. [4600391 ]
  • Okuno E, Nakamura M, Schwarcz R: Two kynurenine aminotransferases in human brain. Brain Res. 1991 Mar 1;542(2):307-12. [2029638 ]
  • 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 ]
  • 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 ]
  • 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 ]
Synthesis Reference: Hayaishi, Osamu. L-Kynurenine sulfate monohydrate. Biochemical Preparations (1953), 3 108-11.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CAS343-65-7
ChEBI57959
HMDBHMDB00684
KEGGC01718
MetaboLightsMTBLC57959
PubChem25245862