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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
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
  • DL-Kynureninefree base
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 + waterhydron + L-Alanine + 2-Aminobenzoic acid
hydron + NADPH + oxygen + L-KynurenineL-3-Hydroxykynurenine + NADP + water
N'-Formylkynurenine + waterFormic acid + hydron + L-Kynurenine
KEGG Reactions
L-Kynurenine + water2-Aminobenzoic acid + L-Alanine + hydron
L-Kynurenine + NADPH + hydron + oxygenNADP + L-3-Hydroxykynurenine + water
water + N-Formyl-L-kynurenineFormic 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
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

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.
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.
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.
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.