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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:20:03 UTC
HMDB IDHMDB0001200
Secondary Accession Numbers
  • HMDB01200
Metabolite Identification
Common NameN'-Formylkynurenine
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 humans, n'-formylkynurenine participates in a number of enzymatic reactions. In particular, n'-formylkynurenine can be biosynthesized from L-tryptophan through the action of the enzyme tryptophan 2,3-dioxygenase. In addition, n'-formylkynurenine can be converted into formylanthranilic acid and L-alanine; which is catalyzed by the enzyme kynureninase. The formation of N′-formylkynurenine is catalyzed by heme dioxygenases. In humans, n'-formylkynurenine is involved in tryptophan metabolism. It is a formylated derivative of kynurenine. N′-Formylkynurenine is an intermediate in the catabolism of tryptophan.
Structure
Data?1582752184
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
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available152.5431661259
DarkChem[M-H]-PredictedNot Available150.87731661259
AllCCS[M+H]+PredictedNot Available152.76132859911
AllCCS[M-H]-PredictedNot Available151.41132859911

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
N'-Formylkynurenine,1TMS,#12331.9617https://arxiv.org/abs/1905.12712
N'-Formylkynurenine,1TMS,#22331.6365https://arxiv.org/abs/1905.12712
N'-Formylkynurenine,1TMS,#32232.2266https://arxiv.org/abs/1905.12712
N'-Formylkynurenine,1TBDMS,#12594.9963https://arxiv.org/abs/1905.12712
N'-Formylkynurenine,1TBDMS,#22590.7888https://arxiv.org/abs/1905.12712
N'-Formylkynurenine,1TBDMS,#32489.4878https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01vo-6910000000-4e6cdf4c6c61e2d98da12016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-4920000000-af1cb05a967f8d904ba22017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052o-0890000000-339c7859f1a6861150c42016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006w-2910000000-0f48ac25f1cb570979972016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-3900000000-4a9b4b58e68782a6f0972016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-6290000000-33116552bdd41736319c2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9450000000-a23cde743537668eb7312016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-9200000000-a4ce591059cb5d3f790c2016-09-12View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
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 ]
  2. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]

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