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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 08:13:06 UTC

Update Date

2021-09-26 23:02:49 UTC

HMDB ID

HMDB0251036

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Desethyl-N-acetylprocainamide

Description

Desethyl-N-acetylprocainamide, also known as DENAPA or deethylacecainide, belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated. Based on a literature review very few articles have been published on Desethyl-N-acetylprocainamide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Desethyl-n-acetylprocainamide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Desethyl-N-acetylprocainamide 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

HMDB0251036
     RDKit          3D
Desethyl-N-acetylprocainamide
 37 37  0  0  0  0  0  0  0  0999 V2000
   -4.9915    2.0377   -0.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8666    0.5906   -0.7026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9044   -0.0843    0.1821 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7708   -1.4751   -0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8462   -2.1393    0.8090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5259   -1.5672    0.8504 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6541   -1.5268   -0.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1040   -2.0385   -1.3476 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6689   -0.9442   -0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4069   -0.7902   -1.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6658   -0.2357   -1.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2816    0.2069   -0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5783    0.7855   -0.2493 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3948    1.1842    0.8122 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7228    1.7772    0.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0493    1.0612    1.9970 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5488    0.0527    0.9796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2656   -0.5128    0.9606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0497    2.3776   -0.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4830    2.6388   -1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5645    2.2938    0.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8197    0.0290   -0.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4680    0.4794   -1.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0300    0.4643    0.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4093   -1.5880   -1.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7675   -1.9390   -0.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7700   -3.2080    0.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3591   -2.0558    1.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1956   -1.1596    1.7478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9699   -1.1220   -2.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475   -0.1164   -2.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0019    0.9467   -1.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5219    2.7601    0.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3200    1.8779    1.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2360    1.1714   -0.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9651    0.3770    1.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7352   -0.6093    1.8859 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 12 17  1  0
 17 18  2  0
 18  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
M  END


  Mrv1652309112110132D          

 18 18  0  0  0  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251036

> <DATABASE_NAME>
hmdb

> <SMILES>
CCNCCNC(=O)C1=CC=C(NC(C)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H19N3O2/c1-3-14-8-9-15-13(18)11-4-6-12(7-5-11)16-10(2)17/h4-7,14H,3,8-9H2,1-2H3,(H,15,18)(H,16,17)

> <INCHI_KEY>
JNDZQWRVBINENC-UHFFFAOYSA-N

> <FORMULA>
C13H19N3O2

> <MOLECULAR_WEIGHT>
249.314

> <EXACT_MASS>
249.147726864

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
28.375552324269655

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-acetamido-N-[2-(ethylamino)ethyl]benzamide

> <ALOGPS_LOGP>
0.51

> <JCHEM_LOGP>
0.2776770830000003

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.259214031194503

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.733265067373747

> <JCHEM_PKA_STRONGEST_BASIC>
9.656952295772777

> <JCHEM_POLAR_SURFACE_AREA>
70.22999999999999

> <JCHEM_REFRACTIVITY>
72.3691

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-acetamido-N-[2-(ethylamino)ethyl]benzamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0251036
     RDKit          3D
Desethyl-N-acetylprocainamide
 37 37  0  0  0  0  0  0  0  0999 V2000
   -4.9915    2.0377   -0.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8666    0.5906   -0.7026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9044   -0.0843    0.1821 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7708   -1.4751   -0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8462   -2.1393    0.8090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5259   -1.5672    0.8504 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6541   -1.5268   -0.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1040   -2.0385   -1.3476 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6689   -0.9442   -0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4069   -0.7902   -1.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6658   -0.2357   -1.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2816    0.2069   -0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5783    0.7855   -0.2493 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3948    1.1842    0.8122 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7228    1.7772    0.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0493    1.0612    1.9970 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5488    0.0527    0.9796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2656   -0.5128    0.9606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0497    2.3776   -0.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4830    2.6388   -1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5645    2.2938    0.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8197    0.0290   -0.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4680    0.4794   -1.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0300    0.4643    0.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4093   -1.5880   -1.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7675   -1.9390   -0.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7700   -3.2080    0.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3591   -2.0558    1.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1956   -1.1596    1.7478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9699   -1.1220   -2.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475   -0.1164   -2.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0019    0.9467   -1.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5219    2.7601    0.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3200    1.8779    1.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2360    1.1714   -0.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9651    0.3770    1.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7352   -0.6093    1.8859 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 12 17  1  0
 17 18  2  0
 18  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       4.001  -6.930   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       8.002  -7.700   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      14.670 -10.010   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      16.004 -12.320   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15   12   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0251036
HETATM    1  C1  UNL     1      -4.991   2.038  -0.345  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.867   0.591  -0.703  1.00  0.00           C  
HETATM    3  N1  UNL     1      -3.904  -0.084   0.182  1.00  0.00           N  
HETATM    4  C3  UNL     1      -3.771  -1.475  -0.184  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.846  -2.139   0.809  1.00  0.00           C  
HETATM    6  N2  UNL     1      -1.526  -1.567   0.850  1.00  0.00           N  
HETATM    7  C5  UNL     1      -0.654  -1.527  -0.264  1.00  0.00           C  
HETATM    8  O1  UNL     1      -1.104  -2.038  -1.348  1.00  0.00           O  
HETATM    9  C6  UNL     1       0.669  -0.944  -0.197  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.407  -0.790  -1.355  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.666  -0.236  -1.340  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.282   0.207  -0.165  1.00  0.00           C  
HETATM   13  N3  UNL     1       4.578   0.786  -0.249  1.00  0.00           N  
HETATM   14  C10 UNL     1       5.395   1.184   0.812  1.00  0.00           C  
HETATM   15  C11 UNL     1       6.723   1.777   0.543  1.00  0.00           C  
HETATM   16  O2  UNL     1       5.049   1.061   1.997  1.00  0.00           O  
HETATM   17  C12 UNL     1       2.549   0.053   0.980  1.00  0.00           C  
HETATM   18  C13 UNL     1       1.266  -0.513   0.961  1.00  0.00           C  
HETATM   19  H1  UNL     1      -6.050   2.378  -0.346  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.483   2.639  -1.133  1.00  0.00           H  
HETATM   21  H3  UNL     1      -4.565   2.294   0.657  1.00  0.00           H  
HETATM   22  H4  UNL     1      -5.820   0.029  -0.557  1.00  0.00           H  
HETATM   23  H5  UNL     1      -4.468   0.479  -1.728  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.030   0.464   0.144  1.00  0.00           H  
HETATM   25  H7  UNL     1      -3.409  -1.588  -1.230  1.00  0.00           H  
HETATM   26  H8  UNL     1      -4.768  -1.939  -0.079  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.770  -3.208   0.488  1.00  0.00           H  
HETATM   28  H10 UNL     1      -3.359  -2.056   1.796  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.196  -1.160   1.748  1.00  0.00           H  
HETATM   30  H12 UNL     1       0.970  -1.122  -2.305  1.00  0.00           H  
HETATM   31  H13 UNL     1       3.248  -0.116  -2.256  1.00  0.00           H  
HETATM   32  H14 UNL     1       5.002   0.947  -1.228  1.00  0.00           H  
HETATM   33  H15 UNL     1       6.522   2.760   0.043  1.00  0.00           H  
HETATM   34  H16 UNL     1       7.320   1.878   1.447  1.00  0.00           H  
HETATM   35  H17 UNL     1       7.236   1.171  -0.256  1.00  0.00           H  
HETATM   36  H18 UNL     1       2.965   0.377   1.925  1.00  0.00           H  
HETATM   37  H19 UNL     1       0.735  -0.609   1.886  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4   24
CONECT    4    5   25   26
CONECT    5    6   27   28
CONECT    6    7   29
CONECT    7    8    8    9
CONECT    9   10   10   18
CONECT   10   11   30
CONECT   11   12   12   31
CONECT   12   13   17
CONECT   13   14   32
CONECT   14   15   16   16
CONECT   15   33   34   35
CONECT   17   18   18   36
CONECT   18   37
END

HMDB0251036
     RDKit          3D
Desethyl-N-acetylprocainamide
 37 37  0  0  0  0  0  0  0  0999 V2000
   -4.9915    2.0377   -0.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8666    0.5906   -0.7026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9044   -0.0843    0.1821 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7708   -1.4751   -0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8462   -2.1393    0.8090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5259   -1.5672    0.8504 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6541   -1.5268   -0.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1040   -2.0385   -1.3476 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6689   -0.9442   -0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4069   -0.7902   -1.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6658   -0.2357   -1.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2816    0.2069   -0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5783    0.7855   -0.2493 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3948    1.1842    0.8122 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7228    1.7772    0.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0493    1.0612    1.9970 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5488    0.0527    0.9796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2656   -0.5128    0.9606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0497    2.3776   -0.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4830    2.6388   -1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5645    2.2938    0.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8197    0.0290   -0.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4680    0.4794   -1.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0300    0.4643    0.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4093   -1.5880   -1.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7675   -1.9390   -0.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7700   -3.2080    0.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3591   -2.0558    1.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1956   -1.1596    1.7478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9699   -1.1220   -2.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475   -0.1164   -2.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0019    0.9467   -1.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5219    2.7601    0.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3200    1.8779    1.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2360    1.1714   -0.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9651    0.3770    1.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7352   -0.6093    1.8859 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 12 17  1  0
 17 18  2  0
 18  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
DENAPA	MeSH
Deethyl-N-acetylprocainamide	MeSH
Deethylacecainide	MeSH

Chemical Formula

C₁₃H₁₉N₃O₂

Average Molecular Weight

249.314

Monoisotopic Molecular Weight

249.147726864

IUPAC Name

4-acetamido-N-[2-(ethylamino)ethyl]benzamide

Traditional Name

4-acetamido-N-[2-(ethylamino)ethyl]benzamide

CAS Registry Number

Not Available

SMILES

CCNCCNC(=O)C1=CC=C(NC(C)=O)C=C1

InChI Identifier

InChI=1S/C13H19N3O2/c1-3-14-8-9-15-13(18)11-4-6-12(7-5-11)16-10(2)17/h4-7,14H,3,8-9H2,1-2H3,(H,15,18)(H,16,17)

InChI Key

JNDZQWRVBINENC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Acylaminobenzoic acid and derivatives

Alternative Parents

Substituents

Acylaminobenzoic acid or derivatives
Acetanilide
Benzamide
N-acetylarylamine
Anilide
Benzoyl
N-arylamide
Acetamide
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Secondary amine
Carboxylic acid derivative
Secondary aliphatic amine
Amine
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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	0.51	ALOGPS
logP	0.28	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	13.73	ChemAxon
pKa (Strongest Basic)	9.66	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	70.23 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	72.37 m³·mol⁻¹	ChemAxon
Polarizability	28.38 Å³	ChemAxon
Number of Rings	1	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]+	160.885	30932474
DeepCCS	[M-H]-	158.528	30932474
DeepCCS	[M-2H]-	191.414	30932474
DeepCCS	[M+Na]+	166.979	30932474
AllCCS	[M+H]+	158.5	32859911
AllCCS	[M+H-H2O]+	155.0	32859911
AllCCS	[M+NH4]+	161.7	32859911
AllCCS	[M+Na]+	162.6	32859911
AllCCS	[M-H]-	162.1	32859911
AllCCS	[M+Na-2H]-	162.6	32859911
AllCCS	[M+HCOO]-	163.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Desethyl-N-acetylprocainamide	CCNCCNC(=O)C1=CC=C(NC(C)=O)C=C1	3244.4	Standard polar	33892256
Desethyl-N-acetylprocainamide	CCNCCNC(=O)C1=CC=C(NC(C)=O)C=C1	2489.0	Standard non polar	33892256
Desethyl-N-acetylprocainamide	CCNCCNC(=O)C1=CC=C(NC(C)=O)C=C1	2675.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Desethyl-N-acetylprocainamide,1TMS,isomer #1	CCN(CCNC(=O)C1=CC=C(NC(C)=O)C=C1)[Si](C)(C)C	2710.7	Semi standard non polar	33892256
Desethyl-N-acetylprocainamide,1TMS,isomer #1	CCN(CCNC(=O)C1=CC=C(NC(C)=O)C=C1)[Si](C)(C)C	2605.2	Standard non polar	33892256
Desethyl-N-acetylprocainamide,1TMS,isomer #1	CCN(CCNC(=O)C1=CC=C(NC(C)=O)C=C1)[Si](C)(C)C	3379.3	Standard polar	33892256
Desethyl-N-acetylprocainamide,1TMS,isomer #2	CCNCCN(C(=O)C1=CC=C(NC(C)=O)C=C1)[Si](C)(C)C	2571.9	Semi standard non polar	33892256
Desethyl-N-acetylprocainamide,1TMS,isomer #2	CCNCCN(C(=O)C1=CC=C(NC(C)=O)C=C1)[Si](C)(C)C	2523.7	Standard non polar	33892256
Desethyl-N-acetylprocainamide,1TMS,isomer #2	CCNCCN(C(=O)C1=CC=C(NC(C)=O)C=C1)[Si](C)(C)C	3179.7	Standard polar	33892256
Desethyl-N-acetylprocainamide,1TMS,isomer #3	CCNCCNC(=O)C1=CC=C(N(C(C)=O)[Si](C)(C)C)C=C1	2421.0	Semi standard non polar	33892256
Desethyl-N-acetylprocainamide,1TMS,isomer #3	CCNCCNC(=O)C1=CC=C(N(C(C)=O)[Si](C)(C)C)C=C1	2379.3	Standard non polar	33892256
Desethyl-N-acetylprocainamide,1TMS,isomer #3	CCNCCNC(=O)C1=CC=C(N(C(C)=O)[Si](C)(C)C)C=C1	2980.7	Standard polar	33892256
Desethyl-N-acetylprocainamide,2TMS,isomer #1	CCN(CCN(C(=O)C1=CC=C(NC(C)=O)C=C1)[Si](C)(C)C)[Si](C)(C)C	2663.9	Semi standard non polar	33892256
Desethyl-N-acetylprocainamide,2TMS,isomer #1	CCN(CCN(C(=O)C1=CC=C(NC(C)=O)C=C1)[Si](C)(C)C)[Si](C)(C)C	2591.7	Standard non polar	33892256
Desethyl-N-acetylprocainamide,2TMS,isomer #1	CCN(CCN(C(=O)C1=CC=C(NC(C)=O)C=C1)[Si](C)(C)C)[Si](C)(C)C	3028.2	Standard polar	33892256
Desethyl-N-acetylprocainamide,2TMS,isomer #2	CCN(CCNC(=O)C1=CC=C(N(C(C)=O)[Si](C)(C)C)C=C1)[Si](C)(C)C	2513.7	Semi standard non polar	33892256
Desethyl-N-acetylprocainamide,2TMS,isomer #2	CCN(CCNC(=O)C1=CC=C(N(C(C)=O)[Si](C)(C)C)C=C1)[Si](C)(C)C	2540.4	Standard non polar	33892256
Desethyl-N-acetylprocainamide,2TMS,isomer #2	CCN(CCNC(=O)C1=CC=C(N(C(C)=O)[Si](C)(C)C)C=C1)[Si](C)(C)C	2847.1	Standard polar	33892256
Desethyl-N-acetylprocainamide,2TMS,isomer #3	CCNCCN(C(=O)C1=CC=C(N(C(C)=O)[Si](C)(C)C)C=C1)[Si](C)(C)C	2288.0	Semi standard non polar	33892256
Desethyl-N-acetylprocainamide,2TMS,isomer #3	CCNCCN(C(=O)C1=CC=C(N(C(C)=O)[Si](C)(C)C)C=C1)[Si](C)(C)C	2461.4	Standard non polar	33892256
Desethyl-N-acetylprocainamide,2TMS,isomer #3	CCNCCN(C(=O)C1=CC=C(N(C(C)=O)[Si](C)(C)C)C=C1)[Si](C)(C)C	2698.7	Standard polar	33892256
Desethyl-N-acetylprocainamide,3TMS,isomer #1	CCN(CCN(C(=O)C1=CC=C(N(C(C)=O)[Si](C)(C)C)C=C1)[Si](C)(C)C)[Si](C)(C)C	2463.3	Semi standard non polar	33892256
Desethyl-N-acetylprocainamide,3TMS,isomer #1	CCN(CCN(C(=O)C1=CC=C(N(C(C)=O)[Si](C)(C)C)C=C1)[Si](C)(C)C)[Si](C)(C)C	2532.6	Standard non polar	33892256
Desethyl-N-acetylprocainamide,3TMS,isomer #1	CCN(CCN(C(=O)C1=CC=C(N(C(C)=O)[Si](C)(C)C)C=C1)[Si](C)(C)C)[Si](C)(C)C	2634.2	Standard polar	33892256
Desethyl-N-acetylprocainamide,1TBDMS,isomer #1	CCN(CCNC(=O)C1=CC=C(NC(C)=O)C=C1)[Si](C)(C)C(C)(C)C	2983.2	Semi standard non polar	33892256
Desethyl-N-acetylprocainamide,1TBDMS,isomer #1	CCN(CCNC(=O)C1=CC=C(NC(C)=O)C=C1)[Si](C)(C)C(C)(C)C	2820.1	Standard non polar	33892256
Desethyl-N-acetylprocainamide,1TBDMS,isomer #1	CCN(CCNC(=O)C1=CC=C(NC(C)=O)C=C1)[Si](C)(C)C(C)(C)C	3371.7	Standard polar	33892256
Desethyl-N-acetylprocainamide,1TBDMS,isomer #2	CCNCCN(C(=O)C1=CC=C(NC(C)=O)C=C1)[Si](C)(C)C(C)(C)C	2865.4	Semi standard non polar	33892256
Desethyl-N-acetylprocainamide,1TBDMS,isomer #2	CCNCCN(C(=O)C1=CC=C(NC(C)=O)C=C1)[Si](C)(C)C(C)(C)C	2708.3	Standard non polar	33892256
Desethyl-N-acetylprocainamide,1TBDMS,isomer #2	CCNCCN(C(=O)C1=CC=C(NC(C)=O)C=C1)[Si](C)(C)C(C)(C)C	3196.4	Standard polar	33892256
Desethyl-N-acetylprocainamide,1TBDMS,isomer #3	CCNCCNC(=O)C1=CC=C(N(C(C)=O)[Si](C)(C)C(C)(C)C)C=C1	2648.4	Semi standard non polar	33892256
Desethyl-N-acetylprocainamide,1TBDMS,isomer #3	CCNCCNC(=O)C1=CC=C(N(C(C)=O)[Si](C)(C)C(C)(C)C)C=C1	2601.9	Standard non polar	33892256
Desethyl-N-acetylprocainamide,1TBDMS,isomer #3	CCNCCNC(=O)C1=CC=C(N(C(C)=O)[Si](C)(C)C(C)(C)C)C=C1	3016.2	Standard polar	33892256
Desethyl-N-acetylprocainamide,2TBDMS,isomer #1	CCN(CCN(C(=O)C1=CC=C(NC(C)=O)C=C1)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3218.3	Semi standard non polar	33892256
Desethyl-N-acetylprocainamide,2TBDMS,isomer #1	CCN(CCN(C(=O)C1=CC=C(NC(C)=O)C=C1)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2956.2	Standard non polar	33892256
Desethyl-N-acetylprocainamide,2TBDMS,isomer #1	CCN(CCN(C(=O)C1=CC=C(NC(C)=O)C=C1)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3119.4	Standard polar	33892256
Desethyl-N-acetylprocainamide,2TBDMS,isomer #2	CCN(CCNC(=O)C1=CC=C(N(C(C)=O)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3017.8	Semi standard non polar	33892256
Desethyl-N-acetylprocainamide,2TBDMS,isomer #2	CCN(CCNC(=O)C1=CC=C(N(C(C)=O)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2935.8	Standard non polar	33892256
Desethyl-N-acetylprocainamide,2TBDMS,isomer #2	CCN(CCNC(=O)C1=CC=C(N(C(C)=O)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2974.8	Standard polar	33892256
Desethyl-N-acetylprocainamide,2TBDMS,isomer #3	CCNCCN(C(=O)C1=CC=C(N(C(C)=O)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2818.3	Semi standard non polar	33892256
Desethyl-N-acetylprocainamide,2TBDMS,isomer #3	CCNCCN(C(=O)C1=CC=C(N(C(C)=O)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2824.2	Standard non polar	33892256
Desethyl-N-acetylprocainamide,2TBDMS,isomer #3	CCNCCN(C(=O)C1=CC=C(N(C(C)=O)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2881.1	Standard polar	33892256
Desethyl-N-acetylprocainamide,3TBDMS,isomer #1	CCN(CCN(C(=O)C1=CC=C(N(C(C)=O)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3195.5	Semi standard non polar	33892256
Desethyl-N-acetylprocainamide,3TBDMS,isomer #1	CCN(CCN(C(=O)C1=CC=C(N(C(C)=O)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3045.4	Standard non polar	33892256
Desethyl-N-acetylprocainamide,3TBDMS,isomer #1	CCN(CCN(C(=O)C1=CC=C(N(C(C)=O)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2922.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Desethyl-N-acetylprocainamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-08fr-8910000000-9b9ba1f87e4a354aa81d	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desethyl-N-acetylprocainamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desethyl-N-acetylprocainamide 10V, Positive-QTOF	splash10-0a4i-0090000000-4dd1327c372acb19fdb3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desethyl-N-acetylprocainamide 20V, Positive-QTOF	splash10-0bt9-0980000000-439875657cad06456603	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desethyl-N-acetylprocainamide 40V, Positive-QTOF	splash10-00di-3900000000-dcb71961d0b78c7019da	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desethyl-N-acetylprocainamide 10V, Negative-QTOF	splash10-0002-0090000000-013b077204607426680c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desethyl-N-acetylprocainamide 20V, Negative-QTOF	splash10-0564-5940000000-c757364f9821d6566261	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desethyl-N-acetylprocainamide 40V, Negative-QTOF	splash10-0006-9620000000-898e28794cf56d88d263	2021-10-12	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

137145

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

155689

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 Desethyl-N-acetylprocainamide (HMDB0251036)

MOL for HMDB0251036 (Desethyl-N-acetylprocainamide)

3D MOL for HMDB0251036 (Desethyl-N-acetylprocainamide)

3D SDF for HMDB0251036 (Desethyl-N-acetylprocainamide)

3D-SDF for HMDB0251036 (Desethyl-N-acetylprocainamide)

PDB for HMDB0251036 (Desethyl-N-acetylprocainamide)

3D PDB for HMDB0251036 (Desethyl-N-acetylprocainamide)

SMILES for HMDB0251036 (Desethyl-N-acetylprocainamide)

INCHI for HMDB0251036 (Desethyl-N-acetylprocainamide)

Structure for HMDB0251036 (Desethyl-N-acetylprocainamide)

3D Structure for HMDB0251036 (Desethyl-N-acetylprocainamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra