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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4)transporters (5) Show 9 proteins XML

enzymes (4)transporters (5) Show 9 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:53 UTC

HMDB ID

HMDB0015169

Secondary Accession Numbers

HMDB15169

Metabolite Identification

Common Name

Procainamide

Description

Procainamide, also known as biocoryl or procanbid, belongs to the class of organic compounds known as aminobenzamides. These are organic compounds containing a benzamide moiety with an amine group attached to the benzene ring. Procainamide is a drug which is used for the treatment of life-threatening ventricular arrhythmias. Procainamide is a very strong basic compound (based on its pKa). In humans, procainamide is involved in the metabolic disorder called the procainamide (antiarrhythmic) action pathway.

Structure

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

HMDB0015169
     RDKit          3D
Procainamide
 38 38  0  0  0  0  0  0  0  0999 V2000
   -4.2899    1.1864   -1.9926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2403    0.0550   -1.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2180    0.2529   -0.0299 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2858   -0.6472    1.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5577   -0.3005    1.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8700    0.2796   -0.6044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8351    0.0700    0.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5032    0.1256   -0.1397 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5508   -0.1450    0.8166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1742   -0.3925    2.0010 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9700   -0.1454    0.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8543   -0.8423    1.3236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2134   -0.8648    1.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7668   -0.2004    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1777   -0.2104   -0.2004 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9000    0.4846   -0.7978 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5178    0.5150   -0.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2831    0.8524   -3.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2507    1.7579   -1.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4476    1.8772   -1.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0015   -0.8610   -1.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2426   -0.1128   -0.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4726   -0.4577    1.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3060   -1.7145    0.8556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2072   -1.1815    2.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3489    0.1099    2.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1441    0.5098    1.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8463   -0.4998   -1.3900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7323    1.3048   -1.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8765    0.8783    1.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8654   -0.9541    0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7303    0.3422   -1.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4086   -1.3715    2.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8962   -1.4016    1.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7856    0.4738    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6510   -0.8444   -0.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3388    1.0195   -1.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8831    1.0523   -1.2449 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
 14 16  1  0
 16 17  2  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
M  END

1035
  Mrv0541 02231215112D          

 17 17  0  0  0  0            999 V2000
    1.6500    0.3341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.3967    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.3341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.3784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    3.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    3.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3 11  1  0  0  0  0
  4 17  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  2  0  0  0  0
 15 17  2  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015169

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H21N3O/c1-3-16(4-2)10-9-15-13(17)11-5-7-12(14)8-6-11/h5-8H,3-4,9-10,14H2,1-2H3,(H,15,17)

> <INCHI_KEY>
REQCZEXYDRLIBE-UHFFFAOYSA-N

> <FORMULA>
C13H21N3O

> <MOLECULAR_WEIGHT>
235.3253

> <EXACT_MASS>
235.168462309

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.685029346227658

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-amino-N-[2-(diethylamino)ethyl]benzamide

> <ALOGPS_LOGP>
1.42

> <JCHEM_LOGP>
0.9508966536666662

> <ALOGPS_LOGS>
-1.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.751574908923946

> <JCHEM_PKA_STRONGEST_BASIC>
9.044348080073618

> <JCHEM_POLAR_SURFACE_AREA>
58.36

> <JCHEM_REFRACTIVITY>
72.24980000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
procainamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015169
     RDKit          3D
Procainamide
 38 38  0  0  0  0  0  0  0  0999 V2000
   -4.2899    1.1864   -1.9926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2403    0.0550   -1.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2180    0.2529   -0.0299 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2858   -0.6472    1.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5577   -0.3005    1.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8700    0.2796   -0.6044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8351    0.0700    0.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5032    0.1256   -0.1397 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5508   -0.1450    0.8166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1742   -0.3925    2.0010 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9700   -0.1454    0.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8543   -0.8423    1.3236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2134   -0.8648    1.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7668   -0.2004    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1777   -0.2104   -0.2004 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9000    0.4846   -0.7978 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5178    0.5150   -0.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2831    0.8524   -3.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2507    1.7579   -1.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4476    1.8772   -1.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0015   -0.8610   -1.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2426   -0.1128   -0.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4726   -0.4577    1.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3060   -1.7145    0.8556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2072   -1.1815    2.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3489    0.1099    2.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1441    0.5098    1.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8463   -0.4998   -1.3900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7323    1.3048   -1.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8765    0.8783    1.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8654   -0.9541    0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7303    0.3422   -1.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4086   -1.3715    2.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8962   -1.4016    1.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7856    0.4738    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6510   -0.8444   -0.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3388    1.0195   -1.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8831    1.0523   -1.2449 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
 14 16  1  0
 16 17  2  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1035                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.080   0.624   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       7.081   4.474   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       5.748   0.624   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       4.414  -6.306   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       7.081   2.934   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.415   5.244   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.748   5.244   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.748   2.164   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415   6.784   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748   6.784   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -0.146   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -1.686   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748  -2.456   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080  -2.456   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.748  -3.996   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.080  -3.996   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -4.766   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2    5    6    7                                                  
CONECT    3    8   11                                                       
CONECT    4   17                                                            
CONECT    5    2    8                                                       
CONECT    6    2    9                                                       
CONECT    7    2   10                                                       
CONECT    8    3    5                                                       
CONECT    9    6                                                            
CONECT   10    7                                                            
CONECT   11    1    3   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   17                                                       
CONECT   17    4   15   16                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0015169
HETATM    1  C1  UNL     1      -4.290   1.186  -1.993  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.240   0.055  -1.004  1.00  0.00           C  
HETATM    3  N1  UNL     1      -3.218   0.253  -0.030  1.00  0.00           N  
HETATM    4  C3  UNL     1      -3.286  -0.647   1.092  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.558  -0.301   1.861  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.870   0.280  -0.604  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.835   0.070   0.428  1.00  0.00           C  
HETATM    8  N2  UNL     1       0.503   0.126  -0.140  1.00  0.00           N  
HETATM    9  C7  UNL     1       1.551  -0.145   0.817  1.00  0.00           C  
HETATM   10  O1  UNL     1       1.174  -0.392   2.001  1.00  0.00           O  
HETATM   11  C8  UNL     1       2.970  -0.145   0.483  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.854  -0.842   1.324  1.00  0.00           C  
HETATM   13  C10 UNL     1       5.213  -0.865   1.099  1.00  0.00           C  
HETATM   14  C11 UNL     1       5.767  -0.200   0.033  1.00  0.00           C  
HETATM   15  N3  UNL     1       7.178  -0.210  -0.200  1.00  0.00           N  
HETATM   16  C12 UNL     1       4.900   0.485  -0.798  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.518   0.515  -0.581  1.00  0.00           C  
HETATM   18  H1  UNL     1      -4.283   0.852  -3.061  1.00  0.00           H  
HETATM   19  H2  UNL     1      -5.251   1.758  -1.784  1.00  0.00           H  
HETATM   20  H3  UNL     1      -3.448   1.877  -1.813  1.00  0.00           H  
HETATM   21  H4  UNL     1      -4.001  -0.861  -1.652  1.00  0.00           H  
HETATM   22  H5  UNL     1      -5.243  -0.113  -0.559  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.473  -0.458   1.828  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.306  -1.714   0.856  1.00  0.00           H  
HETATM   25  H8  UNL     1      -5.207  -1.181   2.014  1.00  0.00           H  
HETATM   26  H9  UNL     1      -4.349   0.110   2.869  1.00  0.00           H  
HETATM   27  H10 UNL     1      -5.144   0.510   1.349  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.846  -0.500  -1.390  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.732   1.305  -1.025  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.877   0.878   1.218  1.00  0.00           H  
HETATM   31  H14 UNL     1      -0.865  -0.954   0.890  1.00  0.00           H  
HETATM   32  H15 UNL     1       0.730   0.342  -1.122  1.00  0.00           H  
HETATM   33  H16 UNL     1       3.409  -1.372   2.165  1.00  0.00           H  
HETATM   34  H17 UNL     1       5.896  -1.402   1.751  1.00  0.00           H  
HETATM   35  H18 UNL     1       7.786   0.474   0.327  1.00  0.00           H  
HETATM   36  H19 UNL     1       7.651  -0.844  -0.852  1.00  0.00           H  
HETATM   37  H20 UNL     1       5.339   1.020  -1.653  1.00  0.00           H  
HETATM   38  H21 UNL     1       2.883   1.052  -1.245  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4    6
CONECT    4    5   23   24
CONECT    5   25   26   27
CONECT    6    7   28   29
CONECT    7    8   30   31
CONECT    8    9   32
CONECT    9   10   10   11
CONECT   11   12   12   17
CONECT   12   13   33
CONECT   13   14   14   34
CONECT   14   15   16
CONECT   15   35   36
CONECT   16   17   17   37
CONECT   17   38
END

HMDB0015169
     RDKit          3D
Procainamide
 38 38  0  0  0  0  0  0  0  0999 V2000
   -4.2899    1.1864   -1.9926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2403    0.0550   -1.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2180    0.2529   -0.0299 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2858   -0.6472    1.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5577   -0.3005    1.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8700    0.2796   -0.6044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8351    0.0700    0.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5032    0.1256   -0.1397 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5508   -0.1450    0.8166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1742   -0.3925    2.0010 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9700   -0.1454    0.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8543   -0.8423    1.3236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2134   -0.8648    1.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7668   -0.2004    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1777   -0.2104   -0.2004 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9000    0.4846   -0.7978 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5178    0.5150   -0.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2831    0.8524   -3.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2507    1.7579   -1.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4476    1.8772   -1.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0015   -0.8610   -1.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2426   -0.1128   -0.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4726   -0.4577    1.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3060   -1.7145    0.8556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2072   -1.1815    2.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3489    0.1099    2.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1441    0.5098    1.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8463   -0.4998   -1.3900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7323    1.3048   -1.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8765    0.8783    1.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8654   -0.9541    0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7303    0.3422   -1.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4086   -1.3715    2.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8962   -1.4016    1.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7856    0.4738    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6510   -0.8444   -0.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3388    1.0195   -1.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8831    1.0523   -1.2449 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
 14 16  1  0
 16 17  2  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Biocoryl	ChEBI
p-Amino-N-(2-diethylaminoethyl)benzamide	ChEBI
p-Aminobenzoic diethylaminoethylamide	ChEBI
Procainamida	ChEBI
Procainamidum	ChEBI
Apo-procainamide	HMDB
Parke davis brand OF procainamide hydrochloride	HMDB
Procainamide hydrochloride	HMDB
Procamide	HMDB
Procanbid	HMDB
Apotex brand OF procainamide hydrochloride	HMDB
Hydrochloride, procainamide	HMDB
Procan	HMDB
Uriach brand OF procainamide hydrochloride	HMDB
Apothecon brand OF procainamide hydrochloride	HMDB
Novocainamide	HMDB
Novocamid	HMDB
Pfizer brand OF procainamide hydrochloride	HMDB
Procaine amide	HMDB
Procan SR	HMDB
Pronestyl	HMDB
Rhythmin	HMDB
Sidmark brand OF procainamide hydrochloride	HMDB
Amide, procaine	HMDB
Bristol-myers squibb brand OF procainamide hydrochloride	HMDB
Monarch brand OF procainamide hydrochloride	HMDB

Chemical Formula

C₁₃H₂₁N₃O

Average Molecular Weight

235.3253

Monoisotopic Molecular Weight

235.168462309

IUPAC Name

4-amino-N-[2-(diethylamino)ethyl]benzamide

Traditional Name

procainamide

CAS Registry Number

51-06-9

SMILES

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

InChI Identifier

InChI=1S/C13H21N3O/c1-3-16(4-2)10-9-15-13(17)11-5-7-12(14)8-6-11/h5-8H,3-4,9-10,14H2,1-2H3,(H,15,17)

InChI Key

REQCZEXYDRLIBE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminobenzamides. These are organic compounds containing a benzamide moiety with an amine group attached to the benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Aminobenzamides

Alternative Parents

Substituents

Aminobenzamide
Benzamide
Benzoyl
Aniline or substituted anilines
Amino acid or derivatives
Carboxamide group
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Carboxylic acid derivative
Amine
Organooxygen compound
Organonitrogen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzamides (CHEBI:8428 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015169)
Membrane (HMDB: HMDB0015169)

Source

Exogenous

Exogenous (HMDB: HMDB0015169)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Procainamide (Antiarrhythmic) Action Pathway (PathBank: SMP0000324)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	165 - 169 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3.02 g/L	Not Available
LogP	1.3	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	155.813	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000795

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.02 g/L	ALOGPS
logP	1.42	ALOGPS
logP	0.95	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	15.75	ChemAxon
pKa (Strongest Basic)	9.04	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	72.25 m³·mol⁻¹	ChemAxon
Polarizability	27.69 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]+	158.884	31661259
DarkChem	[M-H]-	155.627	31661259
DeepCCS	[M+H]+	157.686	30932474
DeepCCS	[M-H]-	155.328	30932474
DeepCCS	[M-2H]-	188.76	30932474
DeepCCS	[M+Na]+	163.823	30932474
AllCCS	[M+H]+	156.0	32859911
AllCCS	[M+H-H2O]+	152.4	32859911
AllCCS	[M+NH4]+	159.3	32859911
AllCCS	[M+Na]+	160.3	32859911
AllCCS	[M-H]-	159.5	32859911
AllCCS	[M+Na-2H]-	160.1	32859911
AllCCS	[M+HCOO]-	161.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.7 minutes	32390414
Predicted by Siyang on May 30, 2022	9.0212 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.19 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	205.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	369.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	211.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	96.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	156.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	44.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	252.4 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	261.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	594.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	573.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	44.0 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	570.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	160.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	198.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	520.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	513.2 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	165.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Procainamide	CCN(CC)CCNC(=O)C1=CC=C(N)C=C1	3313.1	Standard polar	33892256
Procainamide	CCN(CC)CCNC(=O)C1=CC=C(N)C=C1	2277.0	Standard non polar	33892256
Procainamide	CCN(CC)CCNC(=O)C1=CC=C(N)C=C1	2311.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Procainamide,1TMS,isomer #1	CCN(CC)CCNC(=O)C1=CC=C(N[Si](C)(C)C)C=C1	2529.5	Semi standard non polar	33892256
Procainamide,1TMS,isomer #1	CCN(CC)CCNC(=O)C1=CC=C(N[Si](C)(C)C)C=C1	2431.4	Standard non polar	33892256
Procainamide,1TMS,isomer #1	CCN(CC)CCNC(=O)C1=CC=C(N[Si](C)(C)C)C=C1	2840.5	Standard polar	33892256
Procainamide,1TMS,isomer #2	CCN(CC)CCN(C(=O)C1=CC=C(N)C=C1)[Si](C)(C)C	2246.0	Semi standard non polar	33892256
Procainamide,1TMS,isomer #2	CCN(CC)CCN(C(=O)C1=CC=C(N)C=C1)[Si](C)(C)C	2266.8	Standard non polar	33892256
Procainamide,1TMS,isomer #2	CCN(CC)CCN(C(=O)C1=CC=C(N)C=C1)[Si](C)(C)C	3054.8	Standard polar	33892256
Procainamide,2TMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(N[Si](C)(C)C)C=C1)[Si](C)(C)C	2370.5	Semi standard non polar	33892256
Procainamide,2TMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(N[Si](C)(C)C)C=C1)[Si](C)(C)C	2405.3	Standard non polar	33892256
Procainamide,2TMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(N[Si](C)(C)C)C=C1)[Si](C)(C)C	2602.0	Standard polar	33892256
Procainamide,2TMS,isomer #2	CCN(CC)CCNC(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	2463.6	Semi standard non polar	33892256
Procainamide,2TMS,isomer #2	CCN(CC)CCNC(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	2426.1	Standard non polar	33892256
Procainamide,2TMS,isomer #2	CCN(CC)CCNC(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	2657.7	Standard polar	33892256
Procainamide,3TMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C	2380.4	Semi standard non polar	33892256
Procainamide,3TMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C	2423.5	Standard non polar	33892256
Procainamide,3TMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C	2431.0	Standard polar	33892256
Procainamide,1TBDMS,isomer #1	CCN(CC)CCNC(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	2733.1	Semi standard non polar	33892256
Procainamide,1TBDMS,isomer #1	CCN(CC)CCNC(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	2619.5	Standard non polar	33892256
Procainamide,1TBDMS,isomer #1	CCN(CC)CCNC(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	2875.1	Standard polar	33892256
Procainamide,1TBDMS,isomer #2	CCN(CC)CCN(C(=O)C1=CC=C(N)C=C1)[Si](C)(C)C(C)(C)C	2508.5	Semi standard non polar	33892256
Procainamide,1TBDMS,isomer #2	CCN(CC)CCN(C(=O)C1=CC=C(N)C=C1)[Si](C)(C)C(C)(C)C	2472.5	Standard non polar	33892256
Procainamide,1TBDMS,isomer #2	CCN(CC)CCN(C(=O)C1=CC=C(N)C=C1)[Si](C)(C)C(C)(C)C	3078.9	Standard polar	33892256
Procainamide,2TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2880.1	Semi standard non polar	33892256
Procainamide,2TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2776.1	Standard non polar	33892256
Procainamide,2TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2783.0	Standard polar	33892256
Procainamide,2TBDMS,isomer #2	CCN(CC)CCNC(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2931.7	Semi standard non polar	33892256
Procainamide,2TBDMS,isomer #2	CCN(CC)CCNC(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2798.1	Standard non polar	33892256
Procainamide,2TBDMS,isomer #2	CCN(CC)CCNC(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2772.9	Standard polar	33892256
Procainamide,3TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3073.7	Semi standard non polar	33892256
Procainamide,3TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2970.3	Standard non polar	33892256
Procainamide,3TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2724.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Procainamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-9700000000-95dbcabafddc689c7c51	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Procainamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Procainamide 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Procainamide LC-ESI-qTof , Positive-QTOF	splash10-03dr-1940000000-b9d8d6702d2ec39984a3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Procainamide , positive-QTOF	splash10-03dr-1940000000-b9d8d6702d2ec39984a3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Procainamide 40V, Positive-QTOF	splash10-00dl-5900000000-c7352292c2ca704d6892	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Procainamide 10V, Negative-QTOF	splash10-001i-1090000000-bef3da50733e1140e14a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Procainamide 10V, Positive-QTOF	splash10-03dr-0940000000-98ab06e1b8550215cdaa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Procainamide 20V, Positive-QTOF	splash10-03di-0900000000-3c9d04ec798748cc957a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Procainamide 40V, Negative-QTOF	splash10-0006-9000000000-a32b895dd0eb19dc8813	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Procainamide 20V, Negative-QTOF	splash10-0006-9110000000-20900032e174aab10a1b	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procainamide 10V, Positive-QTOF	splash10-00ri-1790000000-c34ddbb3ff1c0983adcb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procainamide 20V, Positive-QTOF	splash10-0fk9-2910000000-eade1dffa69e386cc91e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procainamide 40V, Positive-QTOF	splash10-00dl-9400000000-40f1c1ebcfeb2029c8d6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procainamide 10V, Negative-QTOF	splash10-001i-0190000000-ec82e6634f5291088253	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procainamide 20V, Negative-QTOF	splash10-001l-6690000000-309e42ec6748fb795a10	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procainamide 40V, Negative-QTOF	splash10-0006-9100000000-0b46b12a4a8fed4dd328	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procainamide 10V, Positive-QTOF	splash10-01p9-0970000000-f20ad5a122356337eb22	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procainamide 20V, Positive-QTOF	splash10-0229-1900000000-554557c10d38fea3d2b0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procainamide 40V, Positive-QTOF	splash10-00dl-8900000000-016dd1ee9cecc2bf22e2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procainamide 10V, Negative-QTOF	splash10-001i-0090000000-b59dd73be5c5027352ce	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procainamide 20V, Negative-QTOF	splash10-001i-4390000000-a08741c73eb9ea2fcfdc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procainamide 40V, Negative-QTOF	splash10-0006-9000000000-800956671d0607615bdd	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Procainamide (Antiarrhythmic) Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01035	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01035	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01035

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4744

KEGG Compound ID

C07401

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Procainamide

METLIN ID

Not Available

PubChem Compound

4913

PDB ID

Not Available

ChEBI ID

8428

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

Enzymes

Enzyme Details

1. Cholinesterase

General function:: Involved in carboxylesterase activity
Specific function:: Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:: BCHE
Uniprot ID:: P06276
Molecular weight:: 68417.575

References

Bailey DN: Amitriptyline and procainamide inhibition of cocaine and cocaethylene degradation in human serum in vitro. J Anal Toxicol. 1999 Mar-Apr;23(2):99-102. [PubMed:10192412 ]
Page JD, Wilson IB, Silman I: Butyrylcholinesterase: inhibition by arsenite, fluoride, and other ligands, cooperativity in binding. Mol Pharmacol. 1985 Apr;27(4):437-43. [PubMed:3982389 ]

Enzyme Details

2. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Lessard E, Hamelin BA, Labbe L, O'Hara G, Belanger PM, Turgeon J: Involvement of CYP2D6 activity in the N-oxidation of procainamide in man. Pharmacogenetics. 1999 Dec;9(6):683-96. [PubMed:10634131 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. DNA (cytosine-5)-methyltransferase 1

General function:: Involved in DNA binding
Specific function:: Methylates CpG residues. Preferentially methylates hemimethylated DNA. Associates with DNA replication sites in S phase maintaining the methylation pattern in the newly synthesized strand, that is essential for epigenetic inheritance. Associates with chromatin during G2 and M phases to maintain DNA methylation independently of replication. It is responsible for maintaining methylation patterns established in development. DNA methylation is coordinated with methylation of histones. Mediates transcriptional repression by direct binding to HDAC2. In association with DNMT3B and via the recruitment of CTCFL/BORIS, involved in activation of BAG1 gene expression by modulating dimethylation of promoter histone H3 at H3K4 and H3K9.
Gene Name:: DNMT1
Uniprot ID:: P26358
Molecular weight:: 184817.425

References

Oelke K, Lu Q, Richardson D, Wu A, Deng C, Hanash S, Richardson B: Overexpression of CD70 and overstimulation of IgG synthesis by lupus T cells and T cells treated with DNA methylation inhibitors. Arthritis Rheum. 2004 Jun;50(6):1850-60. [PubMed:15188362 ]
Januchowski R, Jagodzinski PP: Effect of 5-azacytidine and procainamide on CD3-zeta chain expression in Jurkat T cells. Biomed Pharmacother. 2005 Apr;59(3):122-6. [PubMed:15795105 ]
Lee BH, Yegnasubramanian S, Lin X, Nelson WG: Procainamide is a specific inhibitor of DNA methyltransferase 1. J Biol Chem. 2005 Dec 9;280(49):40749-56. Epub 2005 Oct 17. [PubMed:16230360 ]
Scheinbart LS, Johnson MA, Gross LA, Edelstein SR, Richardson BC: Procainamide inhibits DNA methyltransferase in a human T cell line. J Rheumatol. 1991 Apr;18(4):530-4. [PubMed:2066944 ]

Enzyme Details

4. Sodium channel protein type 5 subunit alpha

General function:: Involved in ion channel activity
Specific function:: This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential in the electrocardiogram
Gene Name:: SCN5A
Uniprot ID:: Q14524
Molecular weight:: 226937.5

References

Weiss R, Barmada MM, Nguyen T, Seibel JS, Cavlovich D, Kornblit CA, Angelilli A, Villanueva F, McNamara DM, London B: Clinical and molecular heterogeneity in the Brugada syndrome: a novel gene locus on chromosome 3. Circulation. 2002 Feb 12;105(6):707-13. [PubMed:11839626 ]
Brugada R, Brugada J, Antzelevitch C, Kirsch GE, Potenza D, Towbin JA, Brugada P: Sodium channel blockers identify risk for sudden death in patients with ST-segment elevation and right bundle branch block but structurally normal hearts. Circulation. 2000 Feb 8;101(5):510-5. [PubMed:10662748 ]
Chen SM, Kuo CT, Lin KH, Chiang FT: Brugada syndrome without mutation of the cardiac sodium channel gene in a Taiwanese patient. J Formos Med Assoc. 2000 Nov;99(11):860-2. [PubMed:11155778 ]
Brugada J, Brugada R, Brugada P: [Brugada syndrome]. Arch Mal Coeur Vaiss. 1999 Jul;92(7):847-50. [PubMed:10443304 ]
Brugada J, Brugada P, Brugada R: The syndrome of right bundle branch block ST segment elevation in V1 to V3 and sudden death--the Brugada syndrome. Europace. 1999 Jul;1(3):156-66. [PubMed:11225790 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 5

General function:: Involved in ion transmembrane transporter activity
Specific function:: Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3
Gene Name:: SLC22A5
Uniprot ID:: O76082
Molecular weight:: 62751.1

References

Wu X, Prasad PD, Leibach FH, Ganapathy V: cDNA sequence, transport function, and genomic organization of human OCTN2, a new member of the organic cation transporter family. Biochem Biophys Res Commun. 1998 May 29;246(3):589-95. [PubMed:9618255 ]
Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [PubMed:10525100 ]
Ohashi R, Tamai I, Nezu Ji J, Nikaido H, Hashimoto N, Oku A, Sai Y, Shimane M, Tsuji A: Molecular and physiological evidence for multifunctionality of carnitine/organic cation transporter OCTN2. Mol Pharmacol. 2001 Feb;59(2):358-66. [PubMed:11160873 ]
Wu X, Huang W, Prasad PD, Seth P, Rajan DP, Leibach FH, Chen J, Conway SJ, Ganapathy V: Functional characteristics and tissue distribution pattern of organic cation transporter 2 (OCTN2), an organic cation/carnitine transporter. J Pharmacol Exp Ther. 1999 Sep;290(3):1482-92. [PubMed:10454528 ]

Enzyme Details

2. Solute carrier family 22 member 4

General function:: Involved in ion transmembrane transporter activity
Specific function:: Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 1.78. A key substrate of this transporter seems to be ergothioneine (ET)
Gene Name:: SLC22A4
Uniprot ID:: Q9H015
Molecular weight:: 62154.5

References

Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. [PubMed:10215651 ]
Wu X, George RL, Huang W, Wang H, Conway SJ, Leibach FH, Ganapathy V: Structural and functional characteristics and tissue distribution pattern of rat OCTN1, an organic cation transporter, cloned from placenta. Biochim Biophys Acta. 2000 Jun 1;1466(1-2):315-27. [PubMed:10825452 ]

Enzyme Details

3. Solute carrier family 22 member 1

General function:: Involved in ion transmembrane transporter activity
Specific function:: Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:: SLC22A1
Uniprot ID:: O15245
Molecular weight:: 61187.4

References

Bednarczyk D, Ekins S, Wikel JH, Wright SH: Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1. Mol Pharmacol. 2003 Mar;63(3):489-98. [PubMed:12606755 ]
Zhang L, Dresser MJ, Gray AT, Yost SC, Terashita S, Giacomini KM: Cloning and functional expression of a human liver organic cation transporter. Mol Pharmacol. 1997 Jun;51(6):913-21. [PubMed:9187257 ]
Zhang L, Schaner ME, Giacomini KM: Functional characterization of an organic cation transporter (hOCT1) in a transiently transfected human cell line (HeLa). J Pharmacol Exp Ther. 1998 Jul;286(1):354-61. [PubMed:9655880 ]
Kakehi M, Koyabu N, Nakamura T, Uchiumi T, Kuwano M, Ohtani H, Sawada Y: Functional characterization of mouse cation transporter mOCT2 compared with mOCT1. Biochem Biophys Res Commun. 2002 Aug 23;296(3):644-50. [PubMed:12176030 ]
Green RM, Lo K, Sterritt C, Beier DR: Cloning and functional expression of a mouse liver organic cation transporter. Hepatology. 1999 May;29(5):1556-62. [PubMed:10216142 ]
Zhang L, Dresser MJ, Chun JK, Babbitt PC, Giacomini KM: Cloning and functional characterization of a rat renal organic cation transporter isoform (rOCT1A). J Biol Chem. 1997 Jun 27;272(26):16548-54. [PubMed:9195965 ]
Goralski KB, Lou G, Prowse MT, Gorboulev V, Volk C, Koepsell H, Sitar DS: The cation transporters rOCT1 and rOCT2 interact with bicarbonate but play only a minor role for amantadine uptake into rat renal proximal tubules. J Pharmacol Exp Ther. 2002 Dec;303(3):959-68. [PubMed:12438515 ]
Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759 ]
Grundemann D, Gorboulev V, Gambaryan S, Veyhl M, Koepsell H: Drug excretion mediated by a new prototype of polyspecific transporter. Nature. 1994 Dec 8;372(6506):549-52. [PubMed:7990927 ]
Ishiguro N, Saito A, Yokoyama K, Morikawa M, Igarashi T, Tamai I: Transport of the dopamine D2 agonist pramipexole by rat organic cation transporters OCT1 and OCT2 in kidney. Drug Metab Dispos. 2005 Apr;33(4):495-9. Epub 2005 Jan 7. [PubMed:15640376 ]

Enzyme Details

4. Solute carrier family 22 member 2

General function:: Involved in ion transmembrane transporter activity
Specific function:: Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity
Gene Name:: SLC22A2
Uniprot ID:: O15244
Molecular weight:: 62564.0

References

Urakami Y, Akazawa M, Saito H, Okuda M, Inui K: cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. J Am Soc Nephrol. 2002 Jul;13(7):1703-10. [PubMed:12089365 ]
Gorboulev V, Ulzheimer JC, Akhoundova A, Ulzheimer-Teuber I, Karbach U, Quester S, Baumann C, Lang F, Busch AE, Koepsell H: Cloning and characterization of two human polyspecific organic cation transporters. DNA Cell Biol. 1997 Jul;16(7):871-81. [PubMed:9260930 ]
Kakehi M, Koyabu N, Nakamura T, Uchiumi T, Kuwano M, Ohtani H, Sawada Y: Functional characterization of mouse cation transporter mOCT2 compared with mOCT1. Biochem Biophys Res Commun. 2002 Aug 23;296(3):644-50. [PubMed:12176030 ]
Arndt P, Volk C, Gorboulev V, Budiman T, Popp C, Ulzheimer-Teuber I, Akhoundova A, Koppatz S, Bamberg E, Nagel G, Koepsell H: Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1. Am J Physiol Renal Physiol. 2001 Sep;281(3):F454-68. [PubMed:11502595 ]
Goralski KB, Lou G, Prowse MT, Gorboulev V, Volk C, Koepsell H, Sitar DS: The cation transporters rOCT1 and rOCT2 interact with bicarbonate but play only a minor role for amantadine uptake into rat renal proximal tubules. J Pharmacol Exp Ther. 2002 Dec;303(3):959-68. [PubMed:12438515 ]
Ishiguro N, Saito A, Yokoyama K, Morikawa M, Igarashi T, Tamai I: Transport of the dopamine D2 agonist pramipexole by rat organic cation transporters OCT1 and OCT2 in kidney. Drug Metab Dispos. 2005 Apr;33(4):495-9. Epub 2005 Jan 7. [PubMed:15640376 ]
Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759 ]

Enzyme Details

5. Solute carrier family 22 member 3

General function:: Involved in transmembrane transport
Specific function:: Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain
Gene Name:: SLC22A3
Uniprot ID:: O75751
Molecular weight:: 61279.5

References

Wu X, Huang W, Ganapathy ME, Wang H, Kekuda R, Conway SJ, Leibach FH, Ganapathy V: Structure, function, and regional distribution of the organic cation transporter OCT3 in the kidney. Am J Physiol Renal Physiol. 2000 Sep;279(3):F449-58. [PubMed:10966924 ]

Showing metabocard for Procainamide (HMDB0015169)

MOL for HMDB0015169 (Procainamide)

3D MOL for HMDB0015169 (Procainamide)

3D SDF for HMDB0015169 (Procainamide)

3D-SDF for HMDB0015169 (Procainamide)

PDB for HMDB0015169 (Procainamide)

3D PDB for HMDB0015169 (Procainamide)

SMILES for HMDB0015169 (Procainamide)

INCHI for HMDB0015169 (Procainamide)

Structure for HMDB0015169 (Procainamide)

3D Structure for HMDB0015169 (Procainamide)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References

References

Transporters

References

References

References

References

References