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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:23:14 UTC
HMDB IDHMDB0001200
Secondary Accession Numbers
  • HMDB01200
Metabolite Identification
Common NameN'-Formylkynurenine
DescriptionPlays an especially improtant role in photobiological responses. The excited states of N-formylkynurenine react to produce hydroxyl radicals.
Structure
Thumb
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)-isomerMeSH
N'-formylkynurenine, (S)-isomerMeSH
N-FormylkynurenineMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen 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
Disposition

Biological Location:

  Subcellular:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
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 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
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Tryptophan MetabolismPw000163Pw000163 greyscalePw000163 simpleMap00380
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022486
KNApSAcK IDNot Available
Chemspider ID886
KEGG Compound IDC02406
BioCyc IDN-FORMYLKYNURENINE
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 References
  1. Wong PW, Forman P, Tabahoff B, Justice P: A defect in tryptophan metabolism. Pediatr Res. 1976 Aug;10(8):725-30. [PubMed:133325 ]

Enzymes

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. Has a preference for the L-3-hydroxy form. Also has cysteine-conjugate-beta-lyase activity.
Gene Name:
KYNU
Uniprot ID:
Q16719
Molecular weight:
34634.47
General function:
Involved in heme binding
Specific function:
Catalyzes the cleavage of the pyrrol ring of tryptophan and incorporates both atoms of a molecule of oxygen.
Gene Name:
IDO1
Uniprot ID:
P14902
Molecular weight:
45325.89
Reactions
D-Tryptophan + Oxygen → N'-Formylkynureninedetails
General function:
Involved in hydrolase activity
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 (By similarity).
Gene Name:
AFMID
Uniprot ID:
Q63HM1
Molecular weight:
33991.5
General function:
Involved in heme binding
Specific function:
Catalyzes the first and rate-limiting step in the kynurenine pathway of tryptophan catabolism.
Gene Name:
IDO2
Uniprot ID:
Q6ZQW0
Molecular weight:
47074.745