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N'-Formylkynurenine (YMDB00234)

Identification
YMDB IDYMDB00234
NameN'-Formylkynurenine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionN'-Formylkynurenine 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. N'-Formylkynurenine is a very strong basic compound (based on its pKa). N'-Formylkynurenine exists in all eukaryotes, ranging from yeast to humans. Within yeast, n'-formylkynurenine participates in a number of enzymatic reactions. In particular, n'-formylkynurenine can be converted into formic acid and L-kynurenine through its interaction with the enzyme kynurenine formamidase. In addition, n'-formylkynurenine can be biosynthesized from L-tryptophan through its interaction with the enzyme indoleamine 2,3-dioxygenase. In yeast, n'-formylkynurenine is involved in the metabolic pathway called the nad metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 3-(N-formylanthraniloyl)-Alanine
  • alpha-amino-2-(formylamino)-gamma-oxo-Benzenebutanoate
  • alpha-amino-2-(formylamino)-gamma-oxo-Benzenebutanoic acid
  • Formylkynurenine
  • N-Formyl-L-kynurenine
  • N'-formyl-Kynurenine
  • N'-Formylkynurenine
  • 3-(2-Formamidobenzoyl)alanine
  • N-Formyl-D-kynurenine
  • N-Formyl-delta-kynurenine
  • N'-formylkynurenine, (R)-isomer
  • N'-formylkynurenine, (S)-isomer
  • N-Formylkynurenine
CAS number1022-31-7
WeightAverage: 236.224
Monoisotopic: 236.079706882
InChI KeyBYHJHXPTQMMKCA-UHFFFAOYSA-N
InChIInChI=1S/C11H12N2O4/c12-8(11(16)17)5-10(15)7-3-1-2-4-9(7)13-6-14/h1-4,6,8H,5,12H2,(H,13,14)(H,16,17)
IUPAC Name2-amino-4-(2-formamidophenyl)-4-oxobutanoic acid
Traditional IUPAC NameN-formylkynurenine
Chemical FormulaC11H12N2O4
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])C([H])=O
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
  • Anilide
  • Benzoyl
  • Aryl alkyl ketone
  • N-arylamide
  • Gamma-keto acid
  • Monocyclic benzene moiety
  • Beta-aminoketone
  • Benzenoid
  • Keto acid
  • Vinylogous amide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Amino acid
  • Amino acid or derivatives
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Primary aliphatic amine
  • Primary amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.05 g/LALOGPS
logP-1.8ALOGPS
logP-1.9ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)1.65ChemAxon
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area109.49 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity60.72 m³·mol⁻¹ChemAxon
Polarizability23.06 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
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
N'-Formylkynurenine + water → Formic acid + hydron + L-Kynurenine
L-Tryptophan + oxygen → N'-Formylkynurenine
L-Tryptophan → oxygen + N'-Formylkynurenine
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01vo-6910000000-4e6cdf4c6c61e2d98da1JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-4920000000-af1cb05a967f8d904ba2JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052o-0890000000-339c7859f1a6861150c4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006w-2910000000-0f48ac25f1cb57097997JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-3900000000-4a9b4b58e68782a6f097JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-6290000000-33116552bdd41736319cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9450000000-a23cde743537668eb731JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-9200000000-a4ce591059cb5d3f790cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0950000000-49699bc381d5dd6e3df1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022d-0900000000-d42ed7b74bd169fc7cd3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-6900000000-62029190bf6bbbd9f219JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-010c-0950000000-bf3ca7fe3436c6275730JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-5900000000-075fa36ebbd83bfc9d41JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-f99fb07e6bd62afd2894JSpectraViewer
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
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Jayson, G. G.; Scholes, G.; Weiss, J. Formation of formylkynurenine by the action of x-rays on tryptophan in aqueous solution. Biochemical Journal (1954), 57 386-90.
External Links:
ResourceLink
CHEBI ID18377
HMDB IDHMDB01200
Pubchem Compound ID910
Kegg IDC02406
ChemSpider ID886
FOODB IDFDB022486
WikipediaN'-Formylkynurenine
BioCyc IDN-FORMYLKYNURENINE

Enzymes

Protein Details
1. Indoleamine 2,3-dioxygenase family protein
General function:
Involved in heme binding
Specific function:
Required for biosynthesis of nicotinic acid
Gene Name:
BNA2
Uniprot ID:
P47125
Molecular weight:
50774.80078
Reactions
Protein Details
2. 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.