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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:49:16 UTC

Update Date

2019-07-23 06:35:17 UTC

HMDB ID

HMDB0041944

Secondary Accession Numbers

HMDB41944

Metabolite Identification

Common Name

N-Acetylprocainamide

Description

N-Acetylprocainamide, also known as acecainida or NAPA, 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 a significant number of articles have been published on N-Acetylprocainamide.

Structure

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

HMDB0041944
     RDKit          3D
N-Acetylprocainamide
 43 43  0  0  0  0  0  0  0  0999 V2000
   -5.1873   -2.6467    0.8899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3126   -1.9780   -0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8862   -0.6747    0.1825 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7915    0.3882    0.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3690    0.7611   -1.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5054   -0.4658    0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0928    0.9501    0.6083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6515    1.0642    0.6999 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2417    0.8009   -0.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2200    0.4513   -1.4699 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6879    0.9163   -0.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621    1.5866    0.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6434    1.6439    0.9455 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4892    1.0528    0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9122    1.1329    0.2125 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5942    0.0485    0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0439    0.1052    0.4325 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9623   -1.1667    0.1287 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9014    0.3832   -1.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5294    0.3260   -1.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2802   -2.5635    0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9894   -3.7554    0.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9530   -2.3650    1.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3830   -2.6187   -0.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8108   -2.0763   -1.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3030    1.3082    0.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5998    0.1857    0.9511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8398    0.3229   -1.9923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4597    0.4643   -1.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3992    1.8627   -1.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9130   -0.8117   -0.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1200   -1.1011    1.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5222    1.2983    1.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4855    1.6009   -0.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2327    1.3585    1.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6659    2.0711    1.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0568    2.1755    1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5370   -0.3044   -0.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4186    1.1209    0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3434   -0.5872    1.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3444   -1.9742   -0.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5713   -0.0900   -1.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1025   -0.2010   -1.9592 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
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
 14 19  1  0
 19 20  2  0
 20 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
 12 36  1  0
 13 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
M  END


  Mrv0541 09131211492D          

 20 20  0  0  0  0            999 V2000
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    6.6000    0.0000 C   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
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   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
    2.1434    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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
    3.5724    6.1875    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
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    5.3625    0.0000 N   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    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 11 10  1  0  0  0  0
 12  3  1  0  0  0  0
 13  6  2  0  0  0  0
 13  7  1  0  0  0  0
 14  8  2  0  0  0  0
 14  9  1  0  0  0  0
 15 13  1  0  0  0  0
 16 10  1  0  0  0  0
 16 15  1  0  0  0  0
 17 12  2  0  0  0  0
 17 14  1  4  0  0  0
 18  4  1  0  0  0  0
 18  5  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041944

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN(CC)CCNC(=O)C1=CC=C(C=C1)N=C(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C15H23N3O2/c1-4-18(5-2)11-10-16-15(20)13-6-8-14(9-7-13)17-12(3)19/h6-9H,4-5,10-11H2,1-3H3,(H,16,20)(H,17,19)

> <INCHI_KEY>
KEECCEWTUVWFCV-UHFFFAOYSA-N

> <FORMULA>
C15H23N3O2

> <MOLECULAR_WEIGHT>
277.362

> <EXACT_MASS>
277.179026995

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
32.28918535685388

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(4-{[2-(diethylamino)ethyl]carbamoyl}phenyl)ethanimidic acid

> <ALOGPS_LOGP>
1.61

> <JCHEM_LOGP>
-0.2679877239787675

> <ALOGPS_LOGS>
-2.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.323477067777002

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.031897045624455

> <JCHEM_PKA_STRONGEST_BASIC>
9.048587933357089

> <JCHEM_POLAR_SURFACE_AREA>
64.93

> <JCHEM_REFRACTIVITY>
83.16749999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-(4-{[2-(diethylamino)ethyl]carbamoyl}phenyl)ethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041944
     RDKit          3D
N-Acetylprocainamide
 43 43  0  0  0  0  0  0  0  0999 V2000
   -5.1873   -2.6467    0.8899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3126   -1.9780   -0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8862   -0.6747    0.1825 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7915    0.3882    0.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3690    0.7611   -1.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5054   -0.4658    0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0928    0.9501    0.6083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6515    1.0642    0.6999 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2417    0.8009   -0.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2200    0.4513   -1.4699 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6879    0.9163   -0.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621    1.5866    0.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6434    1.6439    0.9455 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4892    1.0528    0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9122    1.1329    0.2125 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5942    0.0485    0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0439    0.1052    0.4325 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9623   -1.1667    0.1287 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9014    0.3832   -1.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5294    0.3260   -1.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2802   -2.5635    0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9894   -3.7554    0.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9530   -2.3650    1.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3830   -2.6187   -0.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8108   -2.0763   -1.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3030    1.3082    0.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5998    0.1857    0.9511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8398    0.3229   -1.9923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4597    0.4643   -1.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3992    1.8627   -1.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9130   -0.8117   -0.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1200   -1.1011    1.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5222    1.2983    1.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4855    1.6009   -0.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2327    1.3585    1.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6659    2.0711    1.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0568    2.1755    1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5370   -0.3044   -0.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4186    1.1209    0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3434   -0.5872    1.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3444   -1.9742   -0.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5713   -0.0900   -1.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1025   -0.2010   -1.9592 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
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
 14 19  1  0
 19 20  2  0
 20 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
 12 36  1  0
 13 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
M  END

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002  12.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       0.000   7.700   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       6.668  10.010   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      -4.001   6.930   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       5.335  12.320   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334   5.390   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3   12                                                            
CONECT    4    1   18                                                       
CONECT    5    2   18                                                       
CONECT    6    8   13                                                       
CONECT    7    9   13                                                       
CONECT    8    6   14                                                       
CONECT    9    7   14                                                       
CONECT   10   11   16                                                       
CONECT   11   10   18                                                       
CONECT   12    3   17   19                                                  
CONECT   13    6    7   15                                                  
CONECT   14    8    9   17                                                  
CONECT   15   13   16   20                                                  
CONECT   16   10   15                                                       
CONECT   17   12   14                                                       
CONECT   18    4    5   11                                                  
CONECT   19   12                                                            
CONECT   20   15                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0041944
HETATM    1  C1  UNL     1      -5.187  -2.647   0.890  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.313  -1.978  -0.118  1.00  0.00           C  
HETATM    3  N1  UNL     1      -3.886  -0.675   0.182  1.00  0.00           N  
HETATM    4  C3  UNL     1      -4.792   0.388   0.208  1.00  0.00           C  
HETATM    5  C4  UNL     1      -5.369   0.761  -1.144  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.505  -0.466   0.280  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.093   0.950   0.608  1.00  0.00           C  
HETATM    8  N2  UNL     1      -0.651   1.064   0.700  1.00  0.00           N  
HETATM    9  C7  UNL     1       0.242   0.801  -0.360  1.00  0.00           C  
HETATM   10  O1  UNL     1      -0.220   0.451  -1.470  1.00  0.00           O  
HETATM   11  C8  UNL     1       1.688   0.916  -0.216  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.262   1.587   0.836  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.643   1.644   0.946  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.489   1.053   0.037  1.00  0.00           C  
HETATM   15  N3  UNL     1       5.912   1.133   0.213  1.00  0.00           N  
HETATM   16  C12 UNL     1       6.594   0.049   0.253  1.00  0.00           C  
HETATM   17  C13 UNL     1       8.044   0.105   0.432  1.00  0.00           C  
HETATM   18  O2  UNL     1       5.962  -1.167   0.129  1.00  0.00           O  
HETATM   19  C14 UNL     1       3.901   0.383  -1.017  1.00  0.00           C  
HETATM   20  C15 UNL     1       2.529   0.326  -1.127  1.00  0.00           C  
HETATM   21  H1  UNL     1      -6.280  -2.564   0.655  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.989  -3.755   0.827  1.00  0.00           H  
HETATM   23  H3  UNL     1      -4.953  -2.365   1.936  1.00  0.00           H  
HETATM   24  H4  UNL     1      -3.383  -2.619  -0.234  1.00  0.00           H  
HETATM   25  H5  UNL     1      -4.811  -2.076  -1.122  1.00  0.00           H  
HETATM   26  H6  UNL     1      -4.303   1.308   0.585  1.00  0.00           H  
HETATM   27  H7  UNL     1      -5.600   0.186   0.951  1.00  0.00           H  
HETATM   28  H8  UNL     1      -4.840   0.323  -1.992  1.00  0.00           H  
HETATM   29  H9  UNL     1      -6.460   0.464  -1.103  1.00  0.00           H  
HETATM   30  H10 UNL     1      -5.399   1.863  -1.307  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.913  -0.812  -0.595  1.00  0.00           H  
HETATM   32  H12 UNL     1      -2.120  -1.101   1.139  1.00  0.00           H  
HETATM   33  H13 UNL     1      -2.522   1.298   1.558  1.00  0.00           H  
HETATM   34  H14 UNL     1      -2.486   1.601  -0.228  1.00  0.00           H  
HETATM   35  H15 UNL     1      -0.233   1.358   1.603  1.00  0.00           H  
HETATM   36  H16 UNL     1       1.666   2.071   1.584  1.00  0.00           H  
HETATM   37  H17 UNL     1       4.057   2.176   1.778  1.00  0.00           H  
HETATM   38  H18 UNL     1       8.537  -0.304  -0.478  1.00  0.00           H  
HETATM   39  H19 UNL     1       8.419   1.121   0.629  1.00  0.00           H  
HETATM   40  H20 UNL     1       8.343  -0.587   1.268  1.00  0.00           H  
HETATM   41  H21 UNL     1       6.344  -1.974  -0.363  1.00  0.00           H  
HETATM   42  H22 UNL     1       4.571  -0.090  -1.743  1.00  0.00           H  
HETATM   43  H23 UNL     1       2.102  -0.201  -1.959  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4    6
CONECT    4    5   26   27
CONECT    5   28   29   30
CONECT    6    7   31   32
CONECT    7    8   33   34
CONECT    8    9   35
CONECT    9   10   10   11
CONECT   11   12   12   20
CONECT   12   13   36
CONECT   13   14   14   37
CONECT   14   15   19
CONECT   15   16   16
CONECT   16   17   18
CONECT   17   38   39   40
CONECT   18   41
CONECT   19   20   20   42
CONECT   20   43
END

HMDB0041944
     RDKit          3D
N-Acetylprocainamide
 43 43  0  0  0  0  0  0  0  0999 V2000
   -5.1873   -2.6467    0.8899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3126   -1.9780   -0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8862   -0.6747    0.1825 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7915    0.3882    0.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3690    0.7611   -1.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5054   -0.4658    0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0928    0.9501    0.6083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6515    1.0642    0.6999 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2417    0.8009   -0.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2200    0.4513   -1.4699 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6879    0.9163   -0.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621    1.5866    0.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6434    1.6439    0.9455 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4892    1.0528    0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9122    1.1329    0.2125 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5942    0.0485    0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0439    0.1052    0.4325 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9623   -1.1667    0.1287 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9014    0.3832   -1.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5294    0.3260   -1.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2802   -2.5635    0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9894   -3.7554    0.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9530   -2.3650    1.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3830   -2.6187   -0.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8108   -2.0763   -1.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3030    1.3082    0.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5998    0.1857    0.9511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8398    0.3229   -1.9923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4597    0.4643   -1.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3992    1.8627   -1.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9130   -0.8117   -0.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1200   -1.1011    1.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5222    1.2983    1.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4855    1.6009   -0.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2327    1.3585    1.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6659    2.0711    1.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0568    2.1755    1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5370   -0.3044   -0.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4186    1.1209    0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3434   -0.5872    1.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3444   -1.9742   -0.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5713   -0.0900   -1.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1025   -0.2010   -1.9592 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
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
 14 19  1  0
 19 20  2  0
 20 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
 12 36  1  0
 13 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4'-((2-(Diethylamino)ethyl)carbamoyl)acetanilide	ChEBI
Acecainida	ChEBI
Acecainide	ChEBI
Acecainidum	ChEBI
Acekainid	ChEBI
N-Acetyloprokainamid	ChEBI
NAPA	ChEBI
4-Acetamido-N-[2-(diethylamino)ethyl]benzamide	HMDB
Acecainide hydrochloride	HMDB
Acecainide monohydrochloride	HMDB
Monohydrochloride, acecainide	HMDB
Acetylprocainamide	HMDB
N Acetylprocainamide	HMDB
Hydrochloride, acecainide	HMDB

Chemical Formula

C₁₅H₂₃N₃O₂

Average Molecular Weight

277.362

Monoisotopic Molecular Weight

277.179026995

IUPAC Name

N-(4-{[2-(diethylamino)ethyl]carbamoyl}phenyl)ethanimidic acid

Traditional Name

N-(4-{[2-(diethylamino)ethyl]carbamoyl}phenyl)ethanimidic acid

CAS Registry Number

32795-44-1

SMILES

CCN(CC)CCNC(=O)C1=CC=C(C=C1)N=C(C)O

InChI Identifier

InChI=1S/C15H23N3O2/c1-4-18(5-2)11-10-16-15(20)13-6-8-14(9-7-13)17-12(3)19/h6-9H,4-5,10-11H2,1-3H3,(H,16,20)(H,17,19)

InChI Key

KEECCEWTUVWFCV-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
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Carboxylic acid derivative
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

benzamides (CHEBI:60728 )
acetamides (CHEBI:60728 )

Ontology

Not Available

Not Available

Not Available

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	170.519	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000885

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.4 g/L	ALOGPS
logP	1.61	ALOGPS
logP	-0.27	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	7.03	ChemAxon
pKa (Strongest Basic)	9.05	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	64.93 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	83.17 m³·mol⁻¹	ChemAxon
Polarizability	32.29 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
DarkChem	[M+H]+	169.771	31661259
DarkChem	[M-H]-	167.54	31661259
DeepCCS	[M+H]+	171.182	30932474
DeepCCS	[M-H]-	168.824	30932474
DeepCCS	[M-2H]-	201.71	30932474
DeepCCS	[M+Na]+	177.276	30932474
AllCCS	[M+H]+	167.3	32859911
AllCCS	[M+H-H2O]+	164.0	32859911
AllCCS	[M+NH4]+	170.3	32859911
AllCCS	[M+Na]+	171.1	32859911
AllCCS	[M-H]-	170.0	32859911
AllCCS	[M+Na-2H]-	170.5	32859911
AllCCS	[M+HCOO]-	171.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Acetylprocainamide	CCN(CC)CCNC(=O)C1=CC=C(C=C1)N=C(C)O	3301.1	Standard polar	33892256
N-Acetylprocainamide	CCN(CC)CCNC(=O)C1=CC=C(C=C1)N=C(C)O	2568.6	Standard non polar	33892256
N-Acetylprocainamide	CCN(CC)CCNC(=O)C1=CC=C(C=C1)N=C(C)O	2405.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Acetylprocainamide,1TMS,isomer #1	CCN(CC)CCNC(=O)C1=CC=C(N=C(C)O[Si](C)(C)C)C=C1	2484.9	Semi standard non polar	33892256
N-Acetylprocainamide,1TMS,isomer #2	CCN(CC)CCN(C(=O)C1=CC=C(N=C(C)O)C=C1)[Si](C)(C)C	2471.4	Semi standard non polar	33892256
N-Acetylprocainamide,2TMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(N=C(C)O[Si](C)(C)C)C=C1)[Si](C)(C)C	2399.9	Semi standard non polar	33892256
N-Acetylprocainamide,2TMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(N=C(C)O[Si](C)(C)C)C=C1)[Si](C)(C)C	2475.7	Standard non polar	33892256
N-Acetylprocainamide,1TBDMS,isomer #1	CCN(CC)CCNC(=O)C1=CC=C(N=C(C)O[Si](C)(C)C(C)(C)C)C=C1	2722.7	Semi standard non polar	33892256
N-Acetylprocainamide,1TBDMS,isomer #2	CCN(CC)CCN(C(=O)C1=CC=C(N=C(C)O)C=C1)[Si](C)(C)C(C)(C)C	2744.4	Semi standard non polar	33892256
N-Acetylprocainamide,2TBDMS,isomer #1	CCN(CC)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	2877.0	Semi standard non polar	33892256
N-Acetylprocainamide,2TBDMS,isomer #1	CCN(CC)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	2868.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetylprocainamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-9830000000-157c8459a6360292a3ec	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetylprocainamide GC-MS (1 TMS) - 70eV, Positive	splash10-001r-8192000000-dc5afd1bb8f30d799f26	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetylprocainamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 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 - N-Acetylprocainamide 10V, Negative-QTOF	splash10-004i-0090000000-a5489faa4a6e38b65f2c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylprocainamide 20V, Negative-QTOF	splash10-003r-3290000000-7474d308b074ca3edc0e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylprocainamide 40V, Negative-QTOF	splash10-05nf-9400000000-dd008037edfe65a346b6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylprocainamide 10V, Negative-QTOF	splash10-004i-0090000000-275383d20d50219b46b6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylprocainamide 20V, Negative-QTOF	splash10-003r-3290000000-df5803cb908ef5d6fa19	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylprocainamide 40V, Negative-QTOF	splash10-00kf-6900000000-68b5bd928f32460376fe	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylprocainamide 10V, Positive-QTOF	splash10-01u0-0490000000-64caa1ea02dc2de35ecf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylprocainamide 20V, Positive-QTOF	splash10-0il0-1950000000-646feb671873209fc57a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylprocainamide 40V, Positive-QTOF	splash10-00di-6900000000-1dd3b43f11491270cffc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylprocainamide 10V, Positive-QTOF	splash10-056r-0090000000-f9e77889b8f4acf8bee8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylprocainamide 20V, Positive-QTOF	splash10-0bt9-0890000000-a362698f260f0e8d6452	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylprocainamide 40V, Positive-QTOF	splash10-00di-1900000000-6b679c5e7247e834ea03	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4189

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

N-Acetylprocainamide

METLIN ID

Not Available

PubChem Compound

4342

PDB ID

Not Available

ChEBI ID

60728

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

Not Available

Showing metabocard for N-Acetylprocainamide (HMDB0041944)

MOL for HMDB0041944 (N-Acetylprocainamide)

3D MOL for HMDB0041944 (N-Acetylprocainamide)

3D SDF for HMDB0041944 (N-Acetylprocainamide)

3D-SDF for HMDB0041944 (N-Acetylprocainamide)

PDB for HMDB0041944 (N-Acetylprocainamide)

3D PDB for HMDB0041944 (N-Acetylprocainamide)

SMILES for HMDB0041944 (N-Acetylprocainamide)

INCHI for HMDB0041944 (N-Acetylprocainamide)

Structure for HMDB0041944 (N-Acetylprocainamide)

3D Structure for HMDB0041944 (N-Acetylprocainamide)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra