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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-10-25 15:25:12 UTC

HMDB ID

HMDB0001200

Secondary Accession Numbers

HMDB01200

Metabolite Identification

Common Name

N'-Formylkynurenine

Description

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'-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0001200
     RDKit          3D
N'-Formylkynurenine
 29 29  0  0  0  0  0  0  0  0999 V2000
    2.0386    1.4963   -3.3198 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6742    1.6264   -1.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6719    0.5565   -1.5741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1645    0.5533   -0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5346    1.4573    0.5445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7312   -0.5069    0.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0445   -1.5147   -0.7105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8583   -2.5569   -0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3988   -2.6502    0.8578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0922   -1.6594    1.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2776   -0.6030    1.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0572    0.3751    2.4773 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4357    0.3722    3.8181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0506   -0.5458    4.3489 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9364    1.5118   -1.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0416    1.2810   -1.7142 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429    1.6349    0.2546 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4563    0.7620   -3.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8728    2.4176   -3.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2640    2.6275   -1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1523    0.5701   -2.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1808   -0.4370   -1.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5995   -1.4232   -1.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0791   -3.3236   -1.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0619   -3.4835    1.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5700   -1.8025    2.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5420    1.2691    2.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1866    1.2170    4.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2589    0.7784    0.7865 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 16  2  0
 15 17  1  0
 11  6  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  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 02231218592D          

 17 17  0  0  0  0            999 V2000
   -0.0643   -0.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6585   -0.9272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0682    0.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7758   -0.9272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6585   -1.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7296   -0.5866    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7796    0.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6472    0.7191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7758   -1.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0643   -2.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4448   -0.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7834    1.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4485   -1.8203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4949    1.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0719    1.9528    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4949    2.7702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2063    1.5328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
 11 13  2  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  2  0  0  0  0
  9 10  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001200

> <DATABASE_NAME>
hmdb

> <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_KEY>
BYHJHXPTQMMKCA-UHFFFAOYSA-N

> <FORMULA>
C11H12N2O4

> <MOLECULAR_WEIGHT>
236.224

> <EXACT_MASS>
236.079706882

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
23.063871931010954

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
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

$$$$

HMDB0001200
     RDKit          3D
N'-Formylkynurenine
 29 29  0  0  0  0  0  0  0  0999 V2000
    2.0386    1.4963   -3.3198 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6742    1.6264   -1.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6719    0.5565   -1.5741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1645    0.5533   -0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5346    1.4573    0.5445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7312   -0.5069    0.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0445   -1.5147   -0.7105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8583   -2.5569   -0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3988   -2.6502    0.8578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0922   -1.6594    1.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2776   -0.6030    1.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0572    0.3751    2.4773 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4357    0.3722    3.8181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0506   -0.5458    4.3489 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9364    1.5118   -1.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0416    1.2810   -1.7142 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429    1.6349    0.2546 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4563    0.7620   -3.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8728    2.4176   -3.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2640    2.6275   -1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1523    0.5701   -2.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1808   -0.4370   -1.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5995   -1.4232   -1.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0791   -3.3236   -1.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0619   -3.4835    1.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5700   -1.8025    2.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5420    1.2691    2.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1866    1.2170    4.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2589    0.7784    0.7865 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 16  2  0
 15 17  1  0
 11  6  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.120  -0.968   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.229  -1.731   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.127   0.572   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.448  -1.731   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.229  -3.285   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       3.229  -1.095   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -1.455   1.335   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.208   1.342   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.448  -3.285   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.120  -4.069   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.564  -1.865   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.462   2.875   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.571  -3.398   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.790   3.638   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -0.134   3.645   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0      -2.790   5.171   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -4.118   2.861   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10                                                       
CONECT    6    2   11                                                       
CONECT    7    3   12                                                       
CONECT    8    3                                                            
CONECT    9    4   10                                                       
CONECT   10    5    9                                                       
CONECT   11    6   13                                                       
CONECT   12    7   14   15                                                  
CONECT   13   11                                                            
CONECT   14   12   16   17                                                  
CONECT   15   12                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0001200
HETATM    1  N1  UNL     1       2.039   1.496  -3.320  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.674   1.626  -1.885  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.672   0.557  -1.574  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.164   0.553  -0.187  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.535   1.457   0.544  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.731  -0.507   0.222  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.044  -1.515  -0.711  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.858  -2.557  -0.394  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.399  -2.650   0.858  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.092  -1.659   1.776  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.278  -0.603   1.481  1.00  0.00           C  
HETATM   12  N2  UNL     1      -1.057   0.375   2.477  1.00  0.00           N  
HETATM   13  C10 UNL     1      -1.436   0.372   3.818  1.00  0.00           C  
HETATM   14  O2  UNL     1      -2.051  -0.546   4.349  1.00  0.00           O  
HETATM   15  C11 UNL     1       2.936   1.512  -1.109  1.00  0.00           C  
HETATM   16  O3  UNL     1       4.042   1.281  -1.714  1.00  0.00           O  
HETATM   17  O4  UNL     1       3.043   1.635   0.255  1.00  0.00           O  
HETATM   18  H1  UNL     1       1.456   0.762  -3.777  1.00  0.00           H  
HETATM   19  H2  UNL     1       1.873   2.418  -3.784  1.00  0.00           H  
HETATM   20  H3  UNL     1       1.264   2.627  -1.712  1.00  0.00           H  
HETATM   21  H4  UNL     1      -0.152   0.570  -2.325  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.181  -0.437  -1.761  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.600  -1.423  -1.717  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.079  -3.324  -1.149  1.00  0.00           H  
HETATM   25  H8  UNL     1      -3.062  -3.483   1.145  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.570  -1.803   2.757  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.542   1.269   2.192  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.187   1.217   4.456  1.00  0.00           H  
HETATM   29  H12 UNL     1       3.259   0.778   0.787  1.00  0.00           H  
CONECT    1    2   18   19
CONECT    2    3   15   20
CONECT    3    4   21   22
CONECT    4    5    5    6
CONECT    6    7    7   11
CONECT    7    8   23
CONECT    8    9    9   24
CONECT    9   10   25
CONECT   10   11   11   26
CONECT   11   12
CONECT   12   13   27
CONECT   13   14   14   28
CONECT   15   16   16   17
CONECT   17   29
END

HMDB0001200
     RDKit          3D
N'-Formylkynurenine
 29 29  0  0  0  0  0  0  0  0999 V2000
    2.0386    1.4963   -3.3198 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6742    1.6264   -1.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6719    0.5565   -1.5741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1645    0.5533   -0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5346    1.4573    0.5445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7312   -0.5069    0.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0445   -1.5147   -0.7105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8583   -2.5569   -0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3988   -2.6502    0.8578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0922   -1.6594    1.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2776   -0.6030    1.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0572    0.3751    2.4773 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4357    0.3722    3.8181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0506   -0.5458    4.3489 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9364    1.5118   -1.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0416    1.2810   -1.7142 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429    1.6349    0.2546 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4563    0.7620   -3.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8728    2.4176   -3.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2640    2.6275   -1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1523    0.5701   -2.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1808   -0.4370   -1.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5995   -1.4232   -1.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0791   -3.3236   -1.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0619   -3.4835    1.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5700   -1.8025    2.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5420    1.2691    2.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1866    1.2170    4.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2589    0.7784    0.7865 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 16  2  0
 15 17  1  0
 11  6  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-(2-Formamidobenzoyl)alanine	ChEBI
Formylkynurenine	ChEBI
3-(N-Formylanthraniloyl)-alanine	HMDB
alpha-Amino-2-(formylamino)-gamma-oxo-benzenebutanoate	HMDB
alpha-Amino-2-(formylamino)-gamma-oxo-benzenebutanoic acid	HMDB
N'-formyl-kynurenine	HMDB
N-Formyl-D-kynurenine	HMDB
N-Formyl-delta-kynurenine	HMDB
N-Formyl-L-kynurenine	HMDB
N'-formylkynurenine, (R)-isomer	HMDB
N'-formylkynurenine, (S)-isomer	HMDB
N-Formylkynurenine	HMDB

Chemical Formula

C₁₁H₁₂N₂O₄

Average Molecular Weight

236.224

Monoisotopic Molecular Weight

236.079706882

IUPAC Name

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

Traditional Name

N-formylkynurenine

CAS Registry Number

1022-31-7

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 Key

BYHJHXPTQMMKCA-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.

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
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 amino acid derivative (CHEBI:18377 )
non-proteinogenic alpha-amino acid (CHEBI:18377 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0001200)

Source

Endogenous

Endogenous (HMDB: HMDB0001200)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tryptophan Metabolism (PathBank: SMP0063693)
Tryptophan Metabolism (HMDB: HMDB0001200)
NAD Metabolism (PathBank: SMP0002338)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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	23.06 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	152.54	31661259
DarkChem	[M-H]-	150.877	31661259
AllCCS	[M+H]+	152.761	32859911
AllCCS	[M-H]-	151.411	32859911
DeepCCS	[M+H]+	144.593	30932474
DeepCCS	[M-H]-	142.235	30932474
DeepCCS	[M-2H]-	176.816	30932474
DeepCCS	[M+Na]+	152.074	30932474
AllCCS	[M+H]+	152.8	32859911
AllCCS	[M+H-H2O]+	149.0	32859911
AllCCS	[M+NH4]+	156.2	32859911
AllCCS	[M+Na]+	157.2	32859911
AllCCS	[M-H]-	151.4	32859911
AllCCS	[M+Na-2H]-	151.6	32859911
AllCCS	[M+HCOO]-	152.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.08 minutes	32390414
Predicted by Siyang on May 30, 2022	10.346 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.55 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	268.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	648.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	262.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	72.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	48.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	244.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	307.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	676.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	655.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	128.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	873.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	200.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	202.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	460.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	354.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	349.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N'-Formylkynurenine	NC(CC(=O)C1=CC=CC=C1NC=O)C(O)=O	3524.5	Standard polar	33892256
N'-Formylkynurenine	NC(CC(=O)C1=CC=CC=C1NC=O)C(O)=O	2245.6	Standard non polar	33892256
N'-Formylkynurenine	NC(CC(=O)C1=CC=CC=C1NC=O)C(O)=O	2472.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N'-Formylkynurenine,1TMS,isomer #1	C[Si](C)(C)OC(=O)C(N)CC(=O)C1=CC=CC=C1NC=O	2332.0	Semi standard non polar	33892256
N'-Formylkynurenine,1TMS,isomer #2	C[Si](C)(C)NC(CC(=O)C1=CC=CC=C1NC=O)C(=O)O	2331.6	Semi standard non polar	33892256
N'-Formylkynurenine,1TMS,isomer #3	C[Si](C)(C)N(C=O)C1=CC=CC=C1C(=O)CC(N)C(=O)O	2232.2	Semi standard non polar	33892256
N'-Formylkynurenine,2TMS,isomer #1	C[Si](C)(C)NC(CC(=O)C1=CC=CC=C1NC=O)C(=O)O[Si](C)(C)C	2335.9	Semi standard non polar	33892256
N'-Formylkynurenine,2TMS,isomer #1	C[Si](C)(C)NC(CC(=O)C1=CC=CC=C1NC=O)C(=O)O[Si](C)(C)C	2286.8	Standard non polar	33892256
N'-Formylkynurenine,2TMS,isomer #1	C[Si](C)(C)NC(CC(=O)C1=CC=CC=C1NC=O)C(=O)O[Si](C)(C)C	3070.2	Standard polar	33892256
N'-Formylkynurenine,2TMS,isomer #2	C[Si](C)(C)OC(=O)C(N)CC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C	2206.6	Semi standard non polar	33892256
N'-Formylkynurenine,2TMS,isomer #2	C[Si](C)(C)OC(=O)C(N)CC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C	2323.5	Standard non polar	33892256
N'-Formylkynurenine,2TMS,isomer #2	C[Si](C)(C)OC(=O)C(N)CC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C	3034.0	Standard polar	33892256
N'-Formylkynurenine,2TMS,isomer #3	C[Si](C)(C)N(C(CC(=O)C1=CC=CC=C1NC=O)C(=O)O)[Si](C)(C)C	2468.0	Semi standard non polar	33892256
N'-Formylkynurenine,2TMS,isomer #3	C[Si](C)(C)N(C(CC(=O)C1=CC=CC=C1NC=O)C(=O)O)[Si](C)(C)C	2444.6	Standard non polar	33892256
N'-Formylkynurenine,2TMS,isomer #3	C[Si](C)(C)N(C(CC(=O)C1=CC=CC=C1NC=O)C(=O)O)[Si](C)(C)C	3284.6	Standard polar	33892256
N'-Formylkynurenine,2TMS,isomer #4	C[Si](C)(C)NC(CC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C)C(=O)O	2243.9	Semi standard non polar	33892256
N'-Formylkynurenine,2TMS,isomer #4	C[Si](C)(C)NC(CC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C)C(=O)O	2399.0	Standard non polar	33892256
N'-Formylkynurenine,2TMS,isomer #4	C[Si](C)(C)NC(CC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C)C(=O)O	2997.0	Standard polar	33892256
N'-Formylkynurenine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC(=O)C1=CC=CC=C1NC=O)N([Si](C)(C)C)[Si](C)(C)C	2489.8	Semi standard non polar	33892256
N'-Formylkynurenine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC(=O)C1=CC=CC=C1NC=O)N([Si](C)(C)C)[Si](C)(C)C	2402.0	Standard non polar	33892256
N'-Formylkynurenine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC(=O)C1=CC=CC=C1NC=O)N([Si](C)(C)C)[Si](C)(C)C	2933.1	Standard polar	33892256
N'-Formylkynurenine,3TMS,isomer #2	C[Si](C)(C)NC(CC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2236.9	Semi standard non polar	33892256
N'-Formylkynurenine,3TMS,isomer #2	C[Si](C)(C)NC(CC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2352.2	Standard non polar	33892256
N'-Formylkynurenine,3TMS,isomer #2	C[Si](C)(C)NC(CC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2706.9	Standard polar	33892256
N'-Formylkynurenine,3TMS,isomer #3	C[Si](C)(C)N(C=O)C1=CC=CC=C1C(=O)CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2393.1	Semi standard non polar	33892256
N'-Formylkynurenine,3TMS,isomer #3	C[Si](C)(C)N(C=O)C1=CC=CC=C1C(=O)CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2519.1	Standard non polar	33892256
N'-Formylkynurenine,3TMS,isomer #3	C[Si](C)(C)N(C=O)C1=CC=CC=C1C(=O)CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2870.6	Standard polar	33892256
N'-Formylkynurenine,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2440.9	Semi standard non polar	33892256
N'-Formylkynurenine,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2476.0	Standard non polar	33892256
N'-Formylkynurenine,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2656.6	Standard polar	33892256
N'-Formylkynurenine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(N)CC(=O)C1=CC=CC=C1NC=O	2595.0	Semi standard non polar	33892256
N'-Formylkynurenine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CC(=O)C1=CC=CC=C1NC=O)C(=O)O	2590.8	Semi standard non polar	33892256
N'-Formylkynurenine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C=O)C1=CC=CC=C1C(=O)CC(N)C(=O)O	2489.5	Semi standard non polar	33892256
N'-Formylkynurenine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC(=O)C1=CC=CC=C1NC=O)C(=O)O[Si](C)(C)C(C)(C)C	2833.3	Semi standard non polar	33892256
N'-Formylkynurenine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC(=O)C1=CC=CC=C1NC=O)C(=O)O[Si](C)(C)C(C)(C)C	2746.6	Standard non polar	33892256
N'-Formylkynurenine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC(=O)C1=CC=CC=C1NC=O)C(=O)O[Si](C)(C)C(C)(C)C	3171.3	Standard polar	33892256
N'-Formylkynurenine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(N)CC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C(C)(C)C	2670.2	Semi standard non polar	33892256
N'-Formylkynurenine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(N)CC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C(C)(C)C	2740.1	Standard non polar	33892256
N'-Formylkynurenine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(N)CC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C(C)(C)C	3166.9	Standard polar	33892256
N'-Formylkynurenine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(CC(=O)C1=CC=CC=C1NC=O)C(=O)O)[Si](C)(C)C(C)(C)C	2968.5	Semi standard non polar	33892256
N'-Formylkynurenine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(CC(=O)C1=CC=CC=C1NC=O)C(=O)O)[Si](C)(C)C(C)(C)C	2841.9	Standard non polar	33892256
N'-Formylkynurenine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(CC(=O)C1=CC=CC=C1NC=O)C(=O)O)[Si](C)(C)C(C)(C)C	3293.1	Standard polar	33892256
N'-Formylkynurenine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(CC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C(C)(C)C)C(=O)O	2721.6	Semi standard non polar	33892256
N'-Formylkynurenine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(CC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C(C)(C)C)C(=O)O	2777.5	Standard non polar	33892256
N'-Formylkynurenine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(CC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C(C)(C)C)C(=O)O	3151.7	Standard polar	33892256
N'-Formylkynurenine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC(=O)C1=CC=CC=C1NC=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3185.0	Semi standard non polar	33892256
N'-Formylkynurenine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC(=O)C1=CC=CC=C1NC=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3023.4	Standard non polar	33892256
N'-Formylkynurenine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC(=O)C1=CC=CC=C1NC=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3132.9	Standard polar	33892256
N'-Formylkynurenine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2877.9	Semi standard non polar	33892256
N'-Formylkynurenine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2947.7	Standard non polar	33892256
N'-Formylkynurenine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3017.5	Standard polar	33892256
N'-Formylkynurenine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C=O)C1=CC=CC=C1C(=O)CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3071.4	Semi standard non polar	33892256
N'-Formylkynurenine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C=O)C1=CC=CC=C1C(=O)CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3048.0	Standard non polar	33892256
N'-Formylkynurenine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C=O)C1=CC=CC=C1C(=O)CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3102.5	Standard polar	33892256
N'-Formylkynurenine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3302.1	Semi standard non polar	33892256
N'-Formylkynurenine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3214.4	Standard non polar	33892256
N'-Formylkynurenine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC(=O)C1=CC=CC=C1N(C=O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2986.9	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Tryptophan metabolism	Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022486

KNApSAcK ID

Not Available

Chemspider ID

886

KEGG Compound ID

C02406

BioCyc ID

Not Available

BiGG ID

1445551

Wikipedia Link

N'-Formylkynurenine

METLIN ID

Not Available

PubChem Compound

910

PDB ID

Not Available

ChEBI ID

18377

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Jayson, 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

Wong PW, Forman P, Tabahoff B, Justice P: A defect in tryptophan metabolism. Pediatr Res. 1976 Aug;10(8):725-30. [PubMed:133325 ]
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

Enzyme Details

1. Kynureninase

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

Enzyme Details

2. Indoleamine 2,3-dioxygenase 1

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'-Formylkynurenine	details

Enzyme Details

3. 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 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

Enzyme Details

4. Indoleamine 2,3-dioxygenase 2

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

Showing metabocard for N'-Formylkynurenine (HMDB0001200)

MOL for HMDB0001200 (N'-Formylkynurenine)

3D MOL for HMDB0001200 (N'-Formylkynurenine)

3D SDF for HMDB0001200 (N'-Formylkynurenine)

3D-SDF for HMDB0001200 (N'-Formylkynurenine)

PDB for HMDB0001200 (N'-Formylkynurenine)

3D PDB for HMDB0001200 (N'-Formylkynurenine)

SMILES for HMDB0001200 (N'-Formylkynurenine)

INCHI for HMDB0001200 (N'-Formylkynurenine)

Structure for HMDB0001200 (N'-Formylkynurenine)

3D Structure for HMDB0001200 (N'-Formylkynurenine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions