N-Formyl-L-kynurenine (YMDB00725)

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Identification

YMDB ID

YMDB00725

Name

N-Formyl-L-kynurenine

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

L-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. L-Formylkynurenine is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

Synonyms

3-(2-formamidobenzoyl)-L-alanine
3-(N-formylanthraniloyl)-Alanine
alpha-amino-2-(formylamino)-gamma-oxo-Benzenebutanoate
alpha-amino-2-(formylamino)-gamma-oxo-Benzenebutanoic acid
Formylkynurenine
L-Formylkynurenine
N-Formyl-L-kynurenine
N-Formylkynurenine
N'-formyl-Kynurenine
N'-Formylkynurenine

CAS number

1022-31-7

Weight

Average: 236.224
Monoisotopic: 236.079706882

InChI Key

BYHJHXPTQMMKCA-QMMMGPOBSA-N

InChI

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)/t8-/m0/s1

IUPAC Name

(2S)-2-amino-4-(2-formamidophenyl)-4-oxobutanoic acid

Traditional IUPAC Name

N'-formylkynurenine

Chemical Formula

C₁₁H₁₂N₂O₄

SMILES

[H]C(=O)NC1=CC=CC=C1C(=O)C[C@H](N)C(O)=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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Butyrophenone
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
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 Framework

Aromatic homomonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:30249 )
non-proteinogenic amino acid derivative (CHEBI:30249 )
N-formylkynurenine (CHEBI:30249 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	1.05 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-1.9	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	1.65	ChemAxon
pKa (Strongest Basic)	8.96	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	109.49 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	60.72 m³·mol⁻¹	ChemAxon
Polarizability	22.94 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

NAD metabolism	PW002421
Tryptophan metabolism	PW002442

KEGG Pathways

Tryptophan metabolism

ec00380

SMPDB Reactions

Not Available

KEGG Reactions

oxygen + L-Tryptophan → N-Formyl-L-kynurenine

water + N-Formyl-L-kynurenine → Formic acid + L-Kynurenine + hydron

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01vo-6910000000-4e6cdf4c6c61e2d98da1	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0007-3900000000-9e7fb4d194aa098ac501	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052o-0890000000-339c7859f1a6861150c4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006w-2910000000-0f48ac25f1cb57097997	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-3900000000-4a9b4b58e68782a6f097	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-6290000000-33116552bdd41736319c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9450000000-a23cde743537668eb731	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004l-9200000000-a4ce591059cb5d3f790c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052f-0950000000-49699bc381d5dd6e3df1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-022d-0900000000-d42ed7b74bd169fc7cd3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dl-6900000000-62029190bf6bbbd9f219	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-010c-0950000000-bf3ca7fe3436c6275730	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-5900000000-075fa36ebbd83bfc9d41	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9300000000-f99fb07e6bd62afd2894	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

References

References:

Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Panozzo, C., Nawara, M., Suski, C., Kucharczyka, R., Skoneczny, M., Becam, A. M., Rytka, J., Herbert, C. J. (2002). "Aerobic and anaerobic NAD+ metabolism in Saccharomyces cerevisiae." FEBS Lett 517:97-102.12062417

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	30249
HMDB ID	HMDB01200
Pubchem Compound ID	25202092
Kegg ID	C02700
ChemSpider ID	388843
FOODB ID	Not Available
Wikipedia	N'-Formylkynurenine
BioCyc ID	N-FORMYLKYNURENINE

Enzymes

Protein Details

1. Probable kynurenine--oxoglutarate transaminase BNA3

General function:: Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:: Catalyzes the irreversible transamination of the L- tryptophan metabolite L-kynurenine to form kynurenic acid (KA)
Gene Name:: BNA3
Uniprot ID:: P47039
Molecular weight:: 50081.89844

Reactions

L-kynurenine + 2-oxoglutarate → 4-(2-aminophenyl)-2,4-dioxobutanoate + L-glutamate.

Protein Details

2. 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

3. 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.

Structure for #<Compound:0xa9ff8aa8>

Enzymes

Reactions

Reactions

Reactions