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Showing NP-Card for L-Kynurenine (NP0001440)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-11-24 22:23:31 UTC
NP-MRD IDNP0001440
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-Kynurenine
DescriptionKynurenine is a metabolite of the amino acid tryptophan used in the production of niacin. L-Kynurenine is a central compound of the tryptophan metabolism pathway since it can change into the neuroprotective agent kynurenic acid or to the neurotoxic agent quinolinic acid. The break-up of these endogenous compounds' balance can be observable in many disorders such as stroke, epilepsy, multiple sclerosis, and amyotrophic lateral sclerosis. It can also occur in neurodegenerative disorders such as Parkinson's disease, Huntington's, and Alzheimer's disease; and in mental disorders such as schizophrenia and depression.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001440 (L-Kynurenine)


  Mrv1652305271900182D          

 15 15  0  0  1  0            999 V2000
   -0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  END
Download

3D MOL for NP0001440 (L-Kynurenine)

HMDB0000684
     RDKit          3D
L-Kynurenine
 27 27  0  0  0  0  0  0  0  0999 V2000
    1.9070    2.2474    0.9358 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2269    0.9257    0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5794    0.5924    0.4118 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9432   -0.6608    0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9671   -1.5800   -0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6312   -1.2342   -0.2405 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383    0.0333    0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1651    0.4265    0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3939    1.6227    0.6490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2970   -0.4433   -0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4475   -0.4283    0.9327 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4037   -1.4273    0.3890 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2035    0.8307    1.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7360    1.9020    1.4467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5598    0.8256    0.5982 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4346    2.3639    1.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1427    3.0824    0.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3314    1.3176    0.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0046   -0.9200   -0.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2451   -2.5855   -0.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9084   -1.9715   -0.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7235   -0.0985   -1.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0114   -1.4978   -0.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1561   -0.7720    1.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1922   -1.6772   -0.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3881   -2.2937    0.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8822    1.4200   -0.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
  7  2  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  4 19  1  0
  5 20  1  0
  6 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  1
 12 25  1  0
 12 26  1  0
 15 27  1  0
M  END
Download

3D SDF for NP0001440 (L-Kynurenine)


  Mrv1652305271900182D          

 15 15  0  0  1  0            999 V2000
   -0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001440

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CC(=O)C1=CC=CC=C1N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N2O3/c11-7-4-2-1-3-6(7)9(13)5-8(12)10(14)15/h1-4,8H,5,11-12H2,(H,14,15)/t8-/m0/s1

> <INCHI_KEY>
YGPSJZOEDVAXAB-QMMMGPOBSA-N

> <FORMULA>
C10H12N2O3

> <MOLECULAR_WEIGHT>
208.2139

> <EXACT_MASS>
208.08479226

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.588301379965444

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.93

> <JCHEM_LOGP>
-1.9081918809836254

> <ALOGPS_LOGS>
-2.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.06926978291992

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.193089749657625

> <JCHEM_PKA_STRONGEST_BASIC>
8.96449885088756

> <JCHEM_POLAR_SURFACE_AREA>
106.41

> <JCHEM_REFRACTIVITY>
55.05020000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-kynurenine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001440 (L-Kynurenine)

HMDB0000684
     RDKit          3D
L-Kynurenine
 27 27  0  0  0  0  0  0  0  0999 V2000
    1.9070    2.2474    0.9358 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2269    0.9257    0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5794    0.5924    0.4118 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9432   -0.6608    0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9671   -1.5800   -0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6312   -1.2342   -0.2405 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383    0.0333    0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1651    0.4265    0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3939    1.6227    0.6490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2970   -0.4433   -0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4475   -0.4283    0.9327 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4037   -1.4273    0.3890 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2035    0.8307    1.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7360    1.9020    1.4467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5598    0.8256    0.5982 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4346    2.3639    1.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1427    3.0824    0.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3314    1.3176    0.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0046   -0.9200   -0.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2451   -2.5855   -0.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9084   -1.9715   -0.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7235   -0.0985   -1.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0114   -1.4978   -0.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1561   -0.7720    1.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1922   -1.6772   -0.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3881   -2.2937    0.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8822    1.4200   -0.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
  7  2  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  4 19  1  0
  5 20  1  0
  6 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  1
 12 25  1  0
 12 26  1  0
 15 27  1  0
M  END
Download

PDB for NP0001440 (L-Kynurenine)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  N   UNK     0      -1.334   2.310   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.002   0.000   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      -6.668   2.310   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334   0.770   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11                                                            
CONECT   13    2   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END
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3D PDB for NP0001440 (L-Kynurenine)

COMPND    HMDB0000684
HETATM    1  N1  UNL     1       1.907   2.247   0.936  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.227   0.926   0.493  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.579   0.592   0.412  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.943  -0.661   0.003  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.967  -1.580  -0.325  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.631  -1.234  -0.240  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.238   0.033   0.173  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.165   0.426   0.275  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.394   1.623   0.649  1.00  0.00           O  
HETATM   10  C8  UNL     1      -1.297  -0.443  -0.009  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.447  -0.428   0.933  1.00  0.00           C  
HETATM   12  N2  UNL     1      -3.404  -1.427   0.389  1.00  0.00           N  
HETATM   13  C10 UNL     1      -3.204   0.831   1.021  1.00  0.00           C  
HETATM   14  O2  UNL     1      -2.736   1.902   1.447  1.00  0.00           O  
HETATM   15  O3  UNL     1      -4.560   0.826   0.598  1.00  0.00           O  
HETATM   16  H1  UNL     1       1.435   2.364   1.849  1.00  0.00           H  
HETATM   17  H2  UNL     1       2.143   3.082   0.350  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.331   1.318   0.670  1.00  0.00           H  
HETATM   19  H4  UNL     1       5.005  -0.920  -0.057  1.00  0.00           H  
HETATM   20  H5  UNL     1       3.245  -2.586  -0.657  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.908  -1.972  -0.503  1.00  0.00           H  
HETATM   22  H7  UNL     1      -1.723  -0.099  -1.008  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.011  -1.498  -0.204  1.00  0.00           H  
HETATM   24  H9  UNL     1      -2.156  -0.772   1.963  1.00  0.00           H  
HETATM   25  H10 UNL     1      -3.192  -1.677  -0.592  1.00  0.00           H  
HETATM   26  H11 UNL     1      -3.388  -2.294   0.959  1.00  0.00           H  
HETATM   27  H12 UNL     1      -4.882   1.420  -0.126  1.00  0.00           H  
CONECT    1    2   16   17
CONECT    2    3    3    7
CONECT    3    4   18
CONECT    4    5    5   19
CONECT    5    6   20
CONECT    6    7    7   21
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   11   22   23
CONECT   11   12   13   24
CONECT   12   25   26
CONECT   13   14   14   15
CONECT   15   27
END
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SMILES for NP0001440 (L-Kynurenine)

N[C@@H](CC(=O)C1=CC=CC=C1N)C(O)=O
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INCHI for NP0001440 (L-Kynurenine)

InChI=1S/C10H12N2O3/c11-7-4-2-1-3-6(7)9(13)5-8(12)10(14)15/h1-4,8H,5,11-12H2,(H,14,15)/t8-/m0/s1
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Synonyms
ValueSource
(2S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoic acidChEBI
3-Anthraniloyl-L-alanineChEBI
KYNURENINEChEBI
(2S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoateGenerator
(AlphaS)-alpha,2-diamino-3-hydroxy-gamma-oxo-benzenebutanoateHMDB
(AlphaS)-alpha,2-diamino-3-hydroxy-gamma-oxo-benzenebutanoic acidHMDB
(S)-alpha,2-Diamino-3-hydroxy-gamma-oxo-benzenebutanoateHMDB
(S)-alpha,2-Diamino-3-hydroxy-gamma-oxo-benzenebutanoic acidHMDB
3-(3-Hydroxyanthraniloyl)-L-alanineHMDB
3-Anthraniloyl-alanineHMDB
3-AnthraniloylalanineHMDB
3-Hydroxy-L-kynurenineHMDB
alpha,2-Diamino-gamma-oxo-benzenebutanoateHMDB
alpha,2-Diamino-gamma-oxo-benzenebutanoic acidHMDB
DL-KynurenineHMDB
DL-Kynureninefree baseHMDB
KynureninHMDB
QuinurenineHMDB
Chemical FormulaC10H12N2O3
Average Mass208.2139 Da
Monoisotopic Mass208.08479 Da
IUPAC Name(2S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid
Traditional NameL-kynurenine
CAS Registry Number2922-83-0
SMILES
N[C@@H](CC(=O)C1=CC=CC=C1N)C(O)=O
InChI Identifier
InChI=1S/C10H12N2O3/c11-7-4-2-1-3-6(7)9(13)5-8(12)10(14)15/h1-4,8H,5,11-12H2,(H,14,15)/t8-/m0/s1
InChI KeyYGPSJZOEDVAXAB-QMMMGPOBSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Apis ceranaKNApSAcK Database
Arabidopsis thalianaPlant
Bison bisonFooDB
Bombyx moriLOTUS Database
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Daphnia pulexLOTUS Database
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Homo sapiensLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mus musculusLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Species Where Detected
Species NameSourceReference
Agaricus campestrisKNApSAcK Database
Homo sapiens (Blood/serum)KNApSAcK Database
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
  • L-alpha-amino acid
  • Benzoyl
  • Gamma-keto acid
  • Aniline or substituted anilines
  • Aryl alkyl ketone
  • Monocyclic benzene moiety
  • Beta-aminoketone
  • Keto acid
  • Benzenoid
  • Vinylogous amide
  • Amino acid
  • Amino acid or derivatives
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Primary aliphatic amine
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organonitrogen compound
  • Primary amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point191 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.67 g/LALOGPS
logP-1.9ALOGPS
logP-1.9ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.19ChemAxon
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area106.41 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity55.05 m³·mol⁻¹ChemAxon
Polarizability20.59 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000684
DrugBank IDDB02070
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022181
KNApSAcK IDC00007604
Chemspider ID141580
KEGG Compound IDC00328
BioCyc IDCPD-14736
BiGG ID1445574
Wikipedia LinkKynurenine
METLIN ID72
PubChem Compound161166
PDB IDNot Available
ChEBI ID16946
Good Scents IDNot Available
References
General References
  1. Medana IM, Day NP, Salahifar-Sabet H, Stocker R, Smythe G, Bwanaisa L, Njobvu A, Kayira K, Turner GD, Taylor TE, Hunt NH: Metabolites of the kynurenine pathway of tryptophan metabolism in the cerebrospinal fluid of Malawian children with malaria. J Infect Dis. 2003 Sep 15;188(6):844-9. Epub 2003 Sep 9. [PubMed:12964115 ]
  2. Widner B, Sepp N, Kowald E, Ortner U, Wirleitner B, Fritsch P, Baier-Bitterlich G, Fuchs D: Enhanced tryptophan degradation in systemic lupus erythematosus. Immunobiology. 2000 Apr;201(5):621-30. [PubMed:10834318 ]
  3. Widner B, Sepp N, Kowald E, Kind S, Schmuth M, Fuchs D: Degradation of tryptophan in patients with systemic lupus erythematosus. Adv Exp Med Biol. 1999;467:571-7. [PubMed:10721102 ]
  4. Joseph MH: Determination of kynurenine by a simple gas-liquid chromatographic method applicable to urine, plasma, brain and cerebrospinal fluid. J Chromatogr. 1978 Jul 1;146(1):33-41. [PubMed:670356 ]
  5. Heyes MP, Saito K, Lackner A, Wiley CA, Achim CL, Markey SP: Sources of the neurotoxin quinolinic acid in the brain of HIV-1-infected patients and retrovirus-infected macaques. FASEB J. 1998 Jul;12(10):881-96. [PubMed:9657528 ]
  6. Fujigaki S, Saito K, Takemura M, Fujii H, Wada H, Noma A, Seishima M: Species differences in L-tryptophan-kynurenine pathway metabolism: quantification of anthranilic acid and its related enzymes. Arch Biochem Biophys. 1998 Oct 15;358(2):329-35. [PubMed:9784247 ]
  7. Widner B, Werner ER, Schennach H, Fuchs D: An HPLC method to determine tryptophan and kynurenine in serum simultaneously. Adv Exp Med Biol. 1999;467:827-32. [PubMed:10721136 ]
  8. Saito K, Fujigaki S, Heyes MP, Shibata K, Takemura M, Fujii H, Wada H, Noma A, Seishima M: Mechanism of increases in L-kynurenine and quinolinic acid in renal insufficiency. Am J Physiol Renal Physiol. 2000 Sep;279(3):F565-72. [PubMed:10966936 ]
  9. Heyes MP, Saito K, Milstien S, Schiff SJ: Quinolinic acid in tumors, hemorrhage and bacterial infections of the central nervous system in children. J Neurol Sci. 1995 Nov;133(1-2):112-8. [PubMed:8583213 ]
  10. Martinsons A, Rudzite V, Groma V, Bratslavska O, Widner B, Fuchs D: Kynurenine and neopterin in chronic glomerulonephritis. Adv Exp Med Biol. 1999;467:579-86. [PubMed:10721103 ]
  11. Heyes MP, Saito K, Crowley JS, Davis LE, Demitrack MA, Der M, Dilling LA, Elia J, Kruesi MJ, Lackner A, et al.: Quinolinic acid and kynurenine pathway metabolism in inflammatory and non-inflammatory neurological disease. Brain. 1992 Oct;115 ( Pt 5):1249-73. [PubMed:1422788 ]
  12. Moroni F, Carpenedo R, Chiarugi A: Kynurenine hydroxylase and kynureninase inhibitors as tools to study the role of kynurenine metabolites in the central nervous system. Adv Exp Med Biol. 1996;398:203-10. [PubMed:8906267 ]
  13. Calandra P: Research on tryptophan metabolites "via kynurenine" in epidermis of man and mouse. Acta Vitaminol Enzymol. 1975;29(1-6):158-60. [PubMed:1244085 ]
  14. Manuelpillai U, Nicholls T, Wallace EM, Phillips DJ, Guillemin G, Walker D: Increased mRNA expression of kynurenine pathway enzymes in human placentae exposed to bacterial endotoxin. Adv Exp Med Biol. 2003;527:85-9. [PubMed:15206719 ]
  15. Greengard O: Relationship between urinary excretion of kynurenine and liver tryptophan oxygenase activity. Am J Clin Nutr. 1971 Jun;24(6):709-11. [PubMed:5581008 ]
  16. Heinmets F: Computer simulation and analysis of tryptophan metabolism via kynurenine pathway in liver. Comput Biol Med. 1974 Sep;1(4):323-36. [PubMed:4600391 ]
  17. Okuno E, Nakamura M, Schwarcz R: Two kynurenine aminotransferases in human brain. Brain Res. 1991 Mar 1;542(2):307-12. [PubMed:2029638 ]
  18. Altman K, Greengard O: Correlation of kynurenine excretion with liver tryptophan pyrrolase levels in disease and after hydrocortisone induction. J Clin Invest. 1966 Oct;45(10):1527-34. [PubMed:5925511 ]
  19. Pearson SJ, Meldrum A, Reynolds GP: An investigation of the activities of 3-hydroxykynureninase and kynurenine aminotransferase in the brain in Huntington's disease. J Neural Transm Gen Sect. 1995;102(1):67-73. [PubMed:8785025 ]
  20. Hartai Z, Klivenyi P, Janaky T, Penke B, Dux L, Vecsei L: Kynurenine metabolism in plasma and in red blood cells in Parkinson's disease. J Neurol Sci. 2005 Dec 15;239(1):31-5. Epub 2005 Aug 15. [PubMed:16099471 ]