NP-MRD: Showing NP-Card for L-Formylkynurenine (NP0055040)

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Record Information

Version

2.0

Created at

2022-04-28 01:12:12 UTC

Updated at

2022-04-28 01:12:12 UTC

NP-MRD ID

NP0055040

Secondary Accession Numbers

None

Natural Product Identification

Common Name

L-Formylkynurenine

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). L-Formylkynurenine is found in Apis cerana and Arabidopsis thaliana. These are compounds containing 1-phenylbutan-1-one moiety.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
    2.9636   -0.3649    1.7747 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9727   -0.1973    0.3346 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7103   -0.7069   -0.3060 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5006    0.0167    0.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6926    0.8974    1.0613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8089   -0.3237   -0.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8724   -1.3708   -1.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0526   -1.8294   -1.7364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2080   -1.2294   -1.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1852   -0.1870   -0.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9898    0.2722    0.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9965    1.3464    0.9880 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1335    1.9460    1.5438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2952    1.5979    1.3261 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2653    1.2016   -0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4609    2.0390    0.8795 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3215    1.5785   -1.3369 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7331   -0.9777    2.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0352   -0.6921    2.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8164   -0.8126   -0.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733   -0.5403   -1.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5990   -1.7809   -0.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0684   -1.8555   -1.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0553   -2.6503   -2.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1579   -1.5798   -1.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1572    0.2176   -0.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0806    1.7949    1.2843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0444    2.8069    2.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1246    1.3833   -1.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
  2 15  1  0
 15 17  1  0
 15 16  2  0
 11  6  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  6
  3 21  1  0
  3 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 17 29  1  0
M  END


  Mrv0541 02241222332D          

 17 17  0  0  1  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578   -0.8249    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5722   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578   -1.6499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5722    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2867   -0.8249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  7  1  0  0  0  0
  4  1  1  0  0  0  0
  3  4  2  0  0  0  0
  2  5  1  0  0  0  0
  6  5  2  0  0  0  0
  6  3  1  0  0  0  0
  6 15  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  1  0  0  0
 11 13  2  0  0  0  0
 11 14  1  0  0  0  0
 15 17  1  0  0  0  0
 17 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0055040

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](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)/t8-/m0/s1

> <INCHI_KEY>
BYHJHXPTQMMKCA-QMMMGPOBSA-N

> <FORMULA>
C11H12N2O4

> <MOLECULAR_WEIGHT>
236.224

> <EXACT_MASS>
236.079706882

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
22.939359210596578

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-(2-formamidophenyl)-4-oxobutanoic acid

> <ALOGPS_LOGP>
-1.85

> <JCHEM_LOGP>
-1.8897022185097685

> <ALOGPS_LOGS>
-2.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.571277072537978

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.6486962765013677

> <JCHEM_PKA_STRONGEST_BASIC>
8.964484139041431

> <JCHEM_POLAR_SURFACE_AREA>
109.49000000000001

> <JCHEM_REFRACTIVITY>
60.722300000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N'-formylkynurenine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       5.335  -3.080   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       6.668   0.770   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       8.002  -1.540   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       0.000  -3.080   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
CONECT    1    2    4                                                       
CONECT    2    1    5                                                       
CONECT    3    7    4    6                                                  
CONECT    4    1    3                                                       
CONECT    5    2    6                                                       
CONECT    6    5    3   15                                                  
CONECT    7    3    8    9                                                  
CONECT    8    7   10                                                       
CONECT    9    7                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10   13   14                                                  
CONECT   12   10                                                            
CONECT   13   11                                                            
CONECT   14   11                                                            
CONECT   15    6   17                                                       
CONECT   16   17                                                            
CONECT   17   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Value	Source
3-(2-Formamidobenzoyl)-L-alanine	ChEBI
N'-formylkynurenine	ChEBI
N-Formylkynurenine	ChEBI
N-Formyl-L-kynurenine	Kegg
L-Formylkynurenine	ChEBI

Chemical Formula

C₁₁H₁₂N₂O₄

Average Mass

236.2240 Da

Monoisotopic Mass

236.07971 Da

IUPAC Name

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

Traditional Name

N'-formylkynurenine

CAS Registry Number

Not Available

SMILES

N[C@@H](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)/t8-/m0/s1

InChI Key

BYHJHXPTQMMKCA-QMMMGPOBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Apis cerana	LOTUS Database	35616633
Arabidopsis thaliana	Plant	KNApSAcK
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon