Showing metabocard for N'-Formylkynurenine (BMDB0001200)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:42:30 UTC
Update Date2020-05-21 16:28:49 UTC
BMDB IDBMDB0001200
Secondary Accession Numbers
  • BMDB01200
Metabolite Identification
Common NameN'-Formylkynurenine
DescriptionN'-n'-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'-n'-formylkynurenine is possibly soluble (in water) and a very strong basic compound (based on its pKa). N'-n'-formylkynurenine exists in all eukaryotes, ranging from yeast to humans. N'-n'-formylkynurenine participates in a number of enzymatic reactions, within cattle. In particular, N'-n'-formylkynurenine can be biosynthesized from L-tryptophan; which is mediated by the enzyme tryptophan 2,3-dioxygenase. In addition, N'-n'-formylkynurenine can be converted into formylanthranilic acid and L-alanine; which is catalyzed by the enzyme kynureninase. In cattle, n'-n'-formylkynurenine is involved in the metabolic pathway called the tryptophan metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-(2-Formamidobenzoyl)alanineChEBI
FormylkynurenineChEBI
3-(N-Formylanthraniloyl)-alanineHMDB
alpha-Amino-2-(formylamino)-gamma-oxo-benzenebutanoateHMDB
alpha-Amino-2-(formylamino)-gamma-oxo-benzenebutanoic acidHMDB
N'-formyl-kynurenineHMDB
N-Formyl-D-kynurenineHMDB
N-Formyl-delta-kynurenineHMDB
N-Formyl-L-kynurenineHMDB
N'-formylkynurenine, (R)-isomerHMDB
N'-formylkynurenine, (S)-isomerHMDB
N-FormylkynurenineHMDB
Chemical FormulaC11H12N2O4
Average Molecular Weight236.224
Monoisotopic Molecular Weight236.079706882
IUPAC Name2-amino-4-(2-formamidophenyl)-4-oxobutanoic acid
Traditional NameN-formylkynurenine
CAS Registry Number1022-31-7
SMILES
NC(CC(=O)C1=CC=CC=C1NC=O)C(O)=O
InChI Identifier
InChI=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)
InChI KeyBYHJHXPTQMMKCA-UHFFFAOYSA-N
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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01vo-6910000000-4e6cdf4c6c61e2d98da1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-4920000000-af1cb05a967f8d904ba2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052o-0890000000-339c7859f1a6861150c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006w-2910000000-0f48ac25f1cb57097997View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-3900000000-4a9b4b58e68782a6f097View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-6290000000-33116552bdd41736319cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9450000000-a23cde743537668eb731View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-9200000000-a4ce591059cb5d3f790cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0950000000-49699bc381d5dd6e3df1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022d-0900000000-d42ed7b74bd169fc7cd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-6900000000-62029190bf6bbbd9f219View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-010c-0950000000-bf3ca7fe3436c6275730View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-5900000000-075fa36ebbd83bfc9d41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-f99fb07e6bd62afd2894View in MoNA
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001200
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022486
KNApSAcK IDNot Available
Chemspider ID886
KEGG Compound IDC02406
BioCyc IDNot Available
BiGG ID1445551
Wikipedia LinkN'-Formylkynurenine
METLIN IDNot Available
PubChem Compound910
PDB IDNot Available
ChEBI ID18377
References
Synthesis ReferenceJayson, 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.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Tryptophan 2,3-dioxygenase
General function:
Amino acid transport and metabolism
Specific function:
Heme-dependent dioxygenase that catalyzes the oxidative cleavage of the L-tryptophan (L-Trp) pyrrole ring and converts L-tryptophan to N-formyl-L-kynurenine. Catalyzes the oxidative cleavage of the indole moiety.
Gene Name:
TDO2
Uniprot ID:
Q2KIQ5
Molecular weight:
47708.0
Reactions
L-Tryptophan + Oxygen → N'-Formylkynureninedetails
Enzyme Details
2. Kynureninase
General function:
Not Available
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. Has a preference for the L-3-hydroxy form. Also has cysteine-conjugate-beta-lyase activity.
Gene Name:
KYNU
Uniprot ID:
F1MCH2
Molecular weight:
52186.0
Reactions
N'-Formylkynurenine + Water → Formylanthranilic acid + L-Alaninedetails
Enzyme Details
3. Kynurenine formamidase
General function:
Not Available
Specific function:
Catalyzes the hydrolysis of N-formyl-L-kynurenine to L-kynurenine, the second step in the kynurenine pathway of tryptophan degradation. Kynurenine may be further oxidized to nicotinic acid, NAD(H) and NADP(H). Required for elimination of toxic metabolites.
Gene Name:
AFMID
Uniprot ID:
E1BLL5
Molecular weight:
35460.0
Reactions
N'-Formylkynurenine + Water → L-Kynurenine + Formic aciddetails