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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:09:03 UTC

Update Date

2021-09-26 23:10:21 UTC

HMDB ID

HMDB0255503

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Nefiracetam

Description

Nefiracetam belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Based on a literature review a significant number of articles have been published on Nefiracetam. This compound has been identified in human blood as reported by (PMID: 31557052 ). Nefiracetam is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Nefiracetam is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0255503
     RDKit          3D
Nefiracetam
 36 37  0  0  0  0  0  0  0  0999 V2000
   -0.9255    1.3599   -1.8924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0742    1.0762   -1.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1619    1.9261   -0.9079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2151    1.6233   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1902    0.4459    0.6870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0995   -0.3902    0.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0329   -1.6472    1.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0532   -0.0864   -0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9599   -0.9855   -0.3322 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0364   -0.7816    0.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0461    0.2808    1.3570 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2414   -1.6531    0.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4336   -0.8973    0.1658 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2790   -0.2211    1.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5737    0.0551    0.3909 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625    0.2817   -1.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9733   -0.6921   -1.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6047   -1.2343   -2.2142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3111    1.6546   -2.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3074    2.2143   -1.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3159    0.4711   -2.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1702    2.8289   -1.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0856    2.2614    0.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0160    0.2020    1.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2620   -2.3278    0.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0169   -2.1731    1.1841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9723   -1.4814    2.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6561    1.0093    1.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3406   -2.1897    1.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0784   -2.4420   -0.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5024   -0.8458    2.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8750    0.7553    1.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2285   -0.8352    0.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0593    0.9805    0.7165 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6289    1.3084   -1.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8621    0.1489   -1.7694 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  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
  8  2  1  0
 17 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
M  END


  Mrv1572004221603052D          

 18 19  0  0  0  0            999 V2000
   -1.1196    6.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6759    6.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649    7.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    3.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6780    7.4044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7197    7.7015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5253    4.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    3.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4058    4.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5065    6.5974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8912    6.8945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2343    5.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2781    6.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4497    5.5355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1904    4.2187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8474    5.8326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.5286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  4  1  0  0  0  0
 10  1  1  0  0  0  0
 10  5  1  0  0  0  0
 11  2  1  0  0  0  0
 11  6  2  0  0  0  0
 12  9  1  0  0  0  0
 13  7  1  0  0  0  0
 14 10  2  0  0  0  0
 14 11  1  0  0  0  0
 15 12  2  0  0  0  0
 15 14  1  4  0  0  0
 16  8  1  0  0  0  0
 16  9  1  0  0  0  0
 16 13  1  0  0  0  0
 17 12  1  0  0  0  0
 18 13  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255503

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC=CC(C)=C1N=C(O)CN1CCCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H18N2O2/c1-10-5-3-6-11(2)14(10)15-12(17)9-16-8-4-7-13(16)18/h3,5-6H,4,7-9H2,1-2H3,(H,15,17)

> <INCHI_KEY>
NGHTXZCKLWZPGK-UHFFFAOYSA-N

> <FORMULA>
C14H18N2O2

> <MOLECULAR_WEIGHT>
246.31

> <EXACT_MASS>
246.136827828

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
26.97782285265102

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(2,6-dimethylphenyl)-2-(2-oxopyrrolidin-1-yl)ethanimidic acid

> <ALOGPS_LOGP>
1.31

> <JCHEM_LOGP>
2.3106514223333328

> <ALOGPS_LOGS>
-2.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.720197292085965

> <JCHEM_PKA_STRONGEST_BASIC>
1.1960323530747834

> <JCHEM_POLAR_SURFACE_AREA>
52.9

> <JCHEM_REFRACTIVITY>
72.35400000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nefiracetam

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255503
     RDKit          3D
Nefiracetam
 36 37  0  0  0  0  0  0  0  0999 V2000
   -0.9255    1.3599   -1.8924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0742    1.0762   -1.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1619    1.9261   -0.9079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2151    1.6233   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1902    0.4459    0.6870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0995   -0.3902    0.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0329   -1.6472    1.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0532   -0.0864   -0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9599   -0.9855   -0.3322 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0364   -0.7816    0.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0461    0.2808    1.3570 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2414   -1.6531    0.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4336   -0.8973    0.1658 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2790   -0.2211    1.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5737    0.0551    0.3909 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625    0.2817   -1.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9733   -0.6921   -1.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6047   -1.2343   -2.2142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3111    1.6546   -2.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3074    2.2143   -1.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3159    0.4711   -2.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1702    2.8289   -1.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0856    2.2614    0.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0160    0.2020    1.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2620   -2.3278    0.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0169   -2.1731    1.1841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9723   -1.4814    2.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6561    1.0093    1.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3406   -2.1897    1.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0784   -2.4420   -0.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5024   -0.8458    2.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8750    0.7553    1.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2285   -0.8352    0.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0593    0.9805    0.7165 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6289    1.3084   -1.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8621    0.1489   -1.7694 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  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
  8  2  1  0
 17 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0      -2.090  11.285   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.128  12.394   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.121  14.852   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.105   6.410   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.266  13.822   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.343  14.376   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.581   7.875   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.565   6.410   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.624   8.351   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.945  12.315   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.664  12.870   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.304   9.857   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   8.780   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.519  11.839   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       0.839  10.333   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       4.089   7.875   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       3.448  10.888   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335  10.320   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3    5    6                                                       
CONECT    4    7    8                                                       
CONECT    5    3   10                                                       
CONECT    6    3   11                                                       
CONECT    7    4   13                                                       
CONECT    8    4   16                                                       
CONECT    9   12   16                                                       
CONECT   10    1    5   14                                                  
CONECT   11    2    6   14                                                  
CONECT   12    9   15   17                                                  
CONECT   13    7   16   18                                                  
CONECT   14   10   11   15                                                  
CONECT   15   12   14                                                       
CONECT   16    8    9   13                                                  
CONECT   17   12                                                            
CONECT   18   13                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0255503
HETATM    1  C1  UNL     1      -0.925   1.360  -1.892  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.074   1.076  -1.010  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.162   1.926  -0.908  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.215   1.623  -0.071  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.190   0.446   0.687  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.099  -0.390   0.574  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.033  -1.647   1.359  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.053  -0.086  -0.259  1.00  0.00           C  
HETATM    9  N1  UNL     1      -0.960  -0.986  -0.332  1.00  0.00           N  
HETATM   10  C9  UNL     1       0.036  -0.782   0.460  1.00  0.00           C  
HETATM   11  O1  UNL     1       0.046   0.281   1.357  1.00  0.00           O  
HETATM   12  C10 UNL     1       1.241  -1.653   0.480  1.00  0.00           C  
HETATM   13  N2  UNL     1       2.434  -0.897   0.166  1.00  0.00           N  
HETATM   14  C11 UNL     1       3.279  -0.221   1.133  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.574   0.055   0.391  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.062   0.282  -1.023  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.973  -0.692  -1.135  1.00  0.00           C  
HETATM   18  O2  UNL     1       2.605  -1.234  -2.214  1.00  0.00           O  
HETATM   19  H1  UNL     1      -1.311   1.655  -2.908  1.00  0.00           H  
HETATM   20  H2  UNL     1      -0.307   2.214  -1.553  1.00  0.00           H  
HETATM   21  H3  UNL     1      -0.316   0.471  -2.041  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.170   2.829  -1.495  1.00  0.00           H  
HETATM   23  H5  UNL     1      -5.086   2.261   0.038  1.00  0.00           H  
HETATM   24  H6  UNL     1      -5.016   0.202   1.348  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.262  -2.328   0.956  1.00  0.00           H  
HETATM   26  H8  UNL     1      -4.017  -2.173   1.184  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.972  -1.481   2.437  1.00  0.00           H  
HETATM   28  H10 UNL     1      -0.656   1.009   1.374  1.00  0.00           H  
HETATM   29  H11 UNL     1       1.341  -2.190   1.463  1.00  0.00           H  
HETATM   30  H12 UNL     1       1.078  -2.442  -0.286  1.00  0.00           H  
HETATM   31  H13 UNL     1       3.502  -0.846   2.005  1.00  0.00           H  
HETATM   32  H14 UNL     1       2.875   0.755   1.449  1.00  0.00           H  
HETATM   33  H15 UNL     1       5.228  -0.835   0.407  1.00  0.00           H  
HETATM   34  H16 UNL     1       5.059   0.981   0.717  1.00  0.00           H  
HETATM   35  H17 UNL     1       3.629   1.308  -1.087  1.00  0.00           H  
HETATM   36  H18 UNL     1       4.862   0.149  -1.769  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3    8
CONECT    3    4   22
CONECT    4    5    5   23
CONECT    5    6   24
CONECT    6    7    8    8
CONECT    7   25   26   27
CONECT    8    9
CONECT    9   10   10
CONECT   10   11   12
CONECT   11   28
CONECT   12   13   29   30
CONECT   13   14   17
CONECT   14   15   31   32
CONECT   15   16   33   34
CONECT   16   17   35   36
CONECT   17   18   18
END

HMDB0255503
     RDKit          3D
Nefiracetam
 36 37  0  0  0  0  0  0  0  0999 V2000
   -0.9255    1.3599   -1.8924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0742    1.0762   -1.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1619    1.9261   -0.9079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2151    1.6233   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1902    0.4459    0.6870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0995   -0.3902    0.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0329   -1.6472    1.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0532   -0.0864   -0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9599   -0.9855   -0.3322 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0364   -0.7816    0.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0461    0.2808    1.3570 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2414   -1.6531    0.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4336   -0.8973    0.1658 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2790   -0.2211    1.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5737    0.0551    0.3909 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625    0.2817   -1.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9733   -0.6921   -1.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6047   -1.2343   -2.2142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3111    1.6546   -2.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3074    2.2143   -1.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3159    0.4711   -2.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1702    2.8289   -1.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0856    2.2614    0.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0160    0.2020    1.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2620   -2.3278    0.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0169   -2.1731    1.1841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9723   -1.4814    2.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6561    1.0093    1.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3406   -2.1897    1.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0784   -2.4420   -0.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5024   -0.8458    2.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8750    0.7553    1.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2285   -0.8352    0.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0593    0.9805    0.7165 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6289    1.3084   -1.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8621    0.1489   -1.7694 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  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
  8  2  1  0
 17 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Nefiracetam	MeSH
N-(2,6-Dimethylphenyl)-2-(2-oxo-1-pyrrolidinyl)acetamide	MeSH
N-(2,6-Dimethylphenyl)-2-(2-oxopyrrolidin-1-yl)ethanimidate	Generator

Chemical Formula

C₁₄H₁₈N₂O₂

Average Molecular Weight

246.31

Monoisotopic Molecular Weight

246.136827828

IUPAC Name

N-(2,6-dimethylphenyl)-2-(2-oxopyrrolidin-1-yl)ethanimidic acid

Traditional Name

nefiracetam

CAS Registry Number

Not Available

SMILES

CC1=CC=CC(C)=C1N=C(O)CN1CCCC1=O

InChI Identifier

InChI=1S/C14H18N2O2/c1-10-5-3-6-11(2)14(10)15-12(17)9-16-8-4-7-13(16)18/h3,5-6H,4,7-9H2,1-2H3,(H,15,17)

InChI Key

NGHTXZCKLWZPGK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Anilide
N-arylamide
Xylene
M-xylene
2-pyrrolidone
Monocyclic benzene moiety
Benzenoid
N-alkylpyrrolidine
Pyrrolidone
Pyrrolidine
Tertiary carboxylic acid amide
Secondary carboxylic acid amide
Lactam
Carboxamide group
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0255503)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
logP	1.31	ALOGPS
logP	2.31	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	4.72	ChemAxon
pKa (Strongest Basic)	1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.9 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	72.35 m³·mol⁻¹	ChemAxon
Polarizability	26.98 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DeepCCS	[M+H]+	153.85	30932474
DeepCCS	[M-H]-	151.492	30932474
DeepCCS	[M-2H]-	185.333	30932474
DeepCCS	[M+Na]+	160.231	30932474
AllCCS	[M+H]+	156.8	32859911
AllCCS	[M+H-H2O]+	153.0	32859911
AllCCS	[M+NH4]+	160.4	32859911
AllCCS	[M+Na]+	161.4	32859911
AllCCS	[M-H]-	161.0	32859911
AllCCS	[M+Na-2H]-	161.2	32859911
AllCCS	[M+HCOO]-	161.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.3792 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.6 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1432.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	221.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	142.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	56.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	353.1 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	354.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	76.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	814.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	359.0 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	1005.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	229.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	291.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	298.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	125.3 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	105.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nefiracetam	CC1=CC=CC(C)=C1N=C(O)CN1CCCC1=O	3064.4	Standard polar	33892256
Nefiracetam	CC1=CC=CC(C)=C1N=C(O)CN1CCCC1=O	2286.5	Standard non polar	33892256
Nefiracetam	CC1=CC=CC(C)=C1N=C(O)CN1CCCC1=O	2230.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nefiracetam GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9400000000-bb9860d1a2084f6819eb	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nefiracetam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nefiracetam GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nefiracetam GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nefiracetam LC-ESI-qTof , Positive-QTOF	splash10-004j-7920010011-f3cb0b77efee19ef8d89	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nefiracetam , positive-QTOF	splash10-004j-7920010011-f3cb0b77efee19ef8d89	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nefiracetam 10V, Positive-QTOF	splash10-0002-9120000000-83bcf66c8f0160e3cd98	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nefiracetam 20V, Positive-QTOF	splash10-0002-9200000000-303e490a0af024118ac7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nefiracetam 40V, Positive-QTOF	splash10-006t-9100000000-d5d84383a229ca88027b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nefiracetam 10V, Negative-QTOF	splash10-0002-0190000000-b0623bb9a0134062ece8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nefiracetam 20V, Negative-QTOF	splash10-006t-2960000000-11844656b6385ee5ea08	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nefiracetam 40V, Negative-QTOF	splash10-00xu-6900000000-66173968012869cfcf12	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13082

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

64299

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nefiracetam

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Nefiracetam (HMDB0255503)

MOL for HMDB0255503 (Nefiracetam)

3D MOL for HMDB0255503 (Nefiracetam)

3D SDF for HMDB0255503 (Nefiracetam)

3D-SDF for HMDB0255503 (Nefiracetam)

PDB for HMDB0255503 (Nefiracetam)

3D PDB for HMDB0255503 (Nefiracetam)

SMILES for HMDB0255503 (Nefiracetam)

INCHI for HMDB0255503 (Nefiracetam)

Structure for HMDB0255503 (Nefiracetam)

3D Structure for HMDB0255503 (Nefiracetam)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra