You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
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 the action of the enzyme kynurenine formamidase. In addition, n'-formylkynurenine can be biosynthesized from L-tryptophan; which is mediated by the enzyme indoleamine 2,3-dioxygenase. In yeast, n'-formylkynurenine is involved in the metabolic pathway called the nad metabolism pathway.
Structure
Thumb
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-1.9ALOGPS
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 + waterFormic acid + hydron + L-Kynurenine
L-Tryptophan + oxygenN'-Formylkynurenine
L-Tryptophanoxygen + N'-Formylkynurenine
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
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
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

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
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.