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L-Kynurenine (YMDB00375)

Identification
YMDB IDYMDB00375
NameL-Kynurenine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionL-Kynurenine, also known as quinurenine, 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. L-Kynurenine is a very strong basic compound (based on its pKa). L-Kynurenine exists in all eukaryotes, ranging from yeast to humans. Within yeast, L-kynurenine participates in a number of enzymatic reactions. In particular, L-kynurenine can be converted into 3-hydroxy-L-kynurenine; which is catalyzed by the enzyme kynurenine 3-monooxygenase. In addition, formic acid and L-kynurenine can be biosynthesized from n'-formylkynurenine; which is mediated by the enzyme kynurenine formamidase. In yeast, L-kynurenine is involved in the metabolic pathway called the nad metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (alphaS)-alpha,2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoate
  • (alphaS)-alpha,2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoic acid
  • (S)-alpha,2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoate
  • (S)-alpha,2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoic acid
  • 3-(3-Hydroxyanthraniloyl)-L-alanine
  • 3-anthraniloyl-Alanine
  • 3-anthraniloyl-L-alanine
  • 3-Anthraniloylalanine
  • 3-Hydroxy-L-kynurenine
  • alpha,2-diamino-gamma-oxo-Benzenebutanoate
  • alpha,2-diamino-gamma-oxo-Benzenebutanoic acid
  • Kynurenin
  • Quinurenine
  • (2S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoic acid
  • KYNURENINE
  • (2S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoate
  • DL-Kynurenine
  • L-Kynurenine
  • 3-(2-aminobenzoyl)-L-alanine
  • KYNA
CAS number343-65-7
WeightAverage: 208.2139
Monoisotopic: 208.08479226
InChI KeyYGPSJZOEDVAXAB-QMMMGPOBSA-N
InChIInChI=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
IUPAC Name(2S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid
Traditional IUPAC NameL-kynurenine
Chemical FormulaC10H12N2O3
SMILES[H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])C(=O)C1=C([H])C([H])=C([H])C([H])=C1N([H])[H]
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
  • L-alpha-amino acid
  • Benzoyl
  • Gamma-keto acid
  • Aniline or substituted anilines
  • Aryl alkyl ketone
  • Monocyclic benzene moiety
  • Beta-aminoketone
  • Keto acid
  • 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point191 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.67 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity55.05 m³·mol⁻¹ChemAxon
Polarizability20.59 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
NAD metabolismPW002421 ThumbThumb?image type=greyscaleThumb?image type=simple
Tryptophan metabolismPW002442 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Tryptophan metabolismec00380 Map00380
SMPDB Reactions
L-Kynurenine + water → hydron + L-Alanine + 2-Aminobenzoic acid
hydron + NADPH + oxygen + L-Kynurenine → L-3-Hydroxykynurenine + NADP + water
N'-Formylkynurenine + water → Formic acid + hydron + L-Kynurenine
KEGG Reactions
L-Kynurenine + water → 2-Aminobenzoic acid + L-Alanine + hydron
L-Kynurenine + NADPH + hydron + oxygen → NADP + L-3-Hydroxykynurenine + water
water + N-Formyl-L-kynurenine → Formic acid + L-Kynurenine + hydron
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
16 ± 1 µM YEB media with 0.5 mM glucoseaerobicBaker's yeastExperimentally Determined
Not Available
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014l-0931000000-29fa7c323b035cb399d3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014l-0931000000-29fa7c323b035cb399d3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014l-0931000000-a43ae0acafac266101c4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-1910000000-fdc25d09b4da4b1d7657JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9500000000-d7bf6a26c74e0dcabf40JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-4920000000-cb575b96b16b3ef9130fJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-2910000000-366ce08b5736d68dfad0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01bd-5900000000-c18e10be7e029474cf03JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00kf-9300000000-0f8238d38819f6f30d12JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0a4i-0790000000-3fa45266412288bf1c62JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0007-3900000000-a66f45aff81960af7575JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00xv-5900000000-15442ec5aaef005401aeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00r7-7900000000-0833fe9d2739d329f197JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9400000000-d5d45364462a730de436JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0006-0900000000-13929f0bde71b6326d3fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0f6w-2900000000-b2d4f361ffee9fd93bb7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-004j-0900000000-96930a886f7bbcc44df3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-2441a358973abdb063daJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0udi-0900000000-dc4fee4751d629575157JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0900000000-4ec06cc06a3eab2625d6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0900000000-319acefac99779fa7552JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0059-0890000000-4280b92b875a6f754a91JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0059-0890000000-664e2c8904363418682eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00dj-0139000000-aa6188977ba2f460f5bcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00dj-0139000000-ee71a364df13bd095febJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06r7-0920000000-f2e6efdd3988d3010e33JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022a-3900000000-e1c06099462847ad5b97JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9700000000-a9df2d5ca325f97f69f1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-2490000000-9604ae0cc9d437acd878JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-9520000000-8f0ea7d174290496860dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9400000000-9721076505654380d2deJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Panozzo, C., Nawara, M., Suski, C., Kucharczyka, R., Skoneczny, M., Becam, A. M., Rytka, J., Herbert, C. J. (2002). "Aerobic and anaerobic NAD+ metabolism in Saccharomyces cerevisiae." FEBS Lett 517:97-102.12062417
Synthesis Reference:Hayaishi, Osamu. L-Kynurenine sulfate monohydrate. Biochemical Preparations (1953), 3 108-11.
External Links:
ResourceLink
CHEBI ID16946
HMDB IDHMDB00684
Pubchem Compound ID846
Kegg IDC00328
ChemSpider ID141580
FOODB IDFDB022181
WikipediaKynurenine
BioCyc IDL-KYNURENINE

Enzymes

Protein Details
1. Probable kynurenine--oxoglutarate transaminase BNA3
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)
Gene Name:
BNA3
Uniprot ID:
P47039
Molecular weight:
50081.89844
Reactions
L-kynurenine + 2-oxoglutarate → 4-(2-aminophenyl)-2,4-dioxobutanoate + L-glutamate.
Protein Details
2. Kynurenine 3-monooxygenase
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
Gene Name:
BNA4
Uniprot ID:
P38169
Molecular weight:
52428.89844
Reactions
L-kynurenine + NADPH + O(2) → 3-hydroxy-L-kynurenine + NADP(+) + H(2)O.
Protein Details
3. Kynureninase
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
Gene Name:
BNA5
Uniprot ID:
Q05979
Molecular weight:
51031.60156
Reactions
L-kynurenine + H(2)O → anthranilate + L-alanine.
L-3-hydroxykynurenine + H(2)O → 3-hydroxyanthranilate + L-alanine.
Protein Details
4. Probable kynurenine formamidase
General function:
Involved in hydrolase activity
Specific function:
Catalyzes the hydrolysis of N-formyl-L-kynurenine to L- kynurenine, the second step in the conversion of tryptophan to nicotinic acid, NAD(H) and NADP(H)
Gene Name:
BNA7
Uniprot ID:
Q04066
Molecular weight:
29991.0
Reactions
N-formyl-L-kynurenine + H(2)O → formate + L-kynurenine.