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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2023-02-21 17:18:26 UTC

HMDB ID

HMDB0015189

Secondary Accession Numbers

HMDB15189

Metabolite Identification

Common Name

Tocainide

Description

Tocainide is only found in individuals that have used or taken this drug. It is an antiarrhythmic agent which exerts a potential- and frequency-dependent block of sodium channels. [PubChem]Tocainide acts on sodium channels on the neuronal cell membrane, limiting the spread of seizure activity and reducing seizure propagation. Tocainide binds preferentially to the inactive state of the sodium channels.The antiarrhythmic actions are mediated through effects on sodium channels in Purkinje fibers.

Structure

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

HMDB0015189
     RDKit          3D
Tocainide
 30 30  0  0  0  0  0  0  0  0999 V2000
   -0.7488   -1.5981   -1.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5497   -0.8838   -0.8089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8588   -1.2806   -0.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6359   -0.6351    0.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0824    0.4020    1.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7806    0.8223    0.9053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1984    1.9401    1.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0425    0.1532   -0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2868    0.5650   -0.2612 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3936    0.0116    0.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2328   -0.8902    1.3189 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7846    0.4716    0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0850    0.1552   -1.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7302   -0.2228    1.0384 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4461   -1.7798   -2.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4557   -2.6057   -1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0827   -1.0003   -2.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2711   -2.0909   -1.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6534   -0.9712    0.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6814    0.9087    1.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6388    1.5891    2.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5680    2.6141    1.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0196    2.5874    2.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4956    1.3062   -0.9612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8855    1.5655    0.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8254   -0.8901   -1.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1337    0.3714   -1.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4234    0.8169   -1.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3695   -0.2357    2.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9022   -1.1960    0.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
  8  2  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  4 19  1  0
  5 20  1  0
  7 21  1  0
  7 22  1  0
  7 23  1  0
  9 24  1  0
 12 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
M  END

1056
  Mrv0541 02231215122D          

 14 14  0  0  1  0            999 V2000
    4.5080    0.1568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.1568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.8068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  2  0  0  0  0
  2  4  1  0  0  0  0
  2  8  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  5  9  1  0  0  0  0
  5 11  1  0  0  0  0
  6 10  2  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  7 14  1  0  0  0  0
  9 13  2  0  0  0  0
 10 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015189

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(N)C(=O)NC1=C(C)C=CC=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C11H16N2O/c1-7-5-4-6-8(2)10(7)13-11(14)9(3)12/h4-6,9H,12H2,1-3H3,(H,13,14)

> <INCHI_KEY>
BUJAGSGYPOAWEI-UHFFFAOYSA-N

> <FORMULA>
C11H16N2O

> <MOLECULAR_WEIGHT>
192.2575

> <EXACT_MASS>
192.126263144

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
21.59443600616325

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-amino-N-(2,6-dimethylphenyl)propanamide

> <ALOGPS_LOGP>
0.55

> <JCHEM_LOGP>
1.882433361666667

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.653853954939184

> <JCHEM_PKA_STRONGEST_BASIC>
8.227442379036676

> <JCHEM_POLAR_SURFACE_AREA>
55.120000000000005

> <JCHEM_REFRACTIVITY>
58.857000000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tocainide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015189
     RDKit          3D
Tocainide
 30 30  0  0  0  0  0  0  0  0999 V2000
   -0.7488   -1.5981   -1.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5497   -0.8838   -0.8089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8588   -1.2806   -0.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6359   -0.6351    0.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0824    0.4020    1.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7806    0.8223    0.9053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1984    1.9401    1.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0425    0.1532   -0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2868    0.5650   -0.2612 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3936    0.0116    0.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2328   -0.8902    1.3189 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7846    0.4716    0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0850    0.1552   -1.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7302   -0.2228    1.0384 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4461   -1.7798   -2.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4557   -2.6057   -1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0827   -1.0003   -2.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2711   -2.0909   -1.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6534   -0.9712    0.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6814    0.9087    1.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6388    1.5891    2.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5680    2.6141    1.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0196    2.5874    2.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4956    1.3062   -0.9612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8855    1.5655    0.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8254   -0.8901   -1.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1337    0.3714   -1.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4234    0.8169   -1.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3695   -0.2357    2.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9022   -1.1960    0.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
  8  2  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  4 19  1  0
  5 20  1  0
  7 21  1  0
  7 22  1  0
  7 23  1  0
  9 24  1  0
 12 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1056                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       8.415   0.293   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       5.748   0.293   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       8.415   3.373   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.748  -1.247   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.081  -2.017   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414  -2.017   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081   2.603   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081   1.063   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081  -3.557   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -3.557   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415  -1.247   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080  -1.247   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748  -4.327   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.748   3.373   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    4    8                                                       
CONECT    3    7                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4    9   11                                                  
CONECT    6    4   10   12                                                  
CONECT    7    3    8   14                                                  
CONECT    8    1    2    7                                                  
CONECT    9    5   13                                                       
CONECT   10    6   13                                                       
CONECT   11    5                                                            
CONECT   12    6                                                            
CONECT   13    9   10                                                       
CONECT   14    7                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0015189
HETATM    1  C1  UNL     1      -0.749  -1.598  -1.841  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.550  -0.884  -0.809  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.859  -1.281  -0.599  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.636  -0.635   0.358  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.082   0.402   1.090  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.781   0.822   0.905  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.198   1.940   1.701  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.042   0.153  -0.056  1.00  0.00           C  
HETATM    9  N1  UNL     1       0.287   0.565  -0.261  1.00  0.00           N  
HETATM   10  C9  UNL     1       1.394   0.012   0.453  1.00  0.00           C  
HETATM   11  O1  UNL     1       1.233  -0.890   1.319  1.00  0.00           O  
HETATM   12  C10 UNL     1       2.785   0.472   0.210  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.085   0.155  -1.261  1.00  0.00           C  
HETATM   14  N2  UNL     1       3.730  -0.223   1.038  1.00  0.00           N  
HETATM   15  H1  UNL     1      -1.446  -1.780  -2.696  1.00  0.00           H  
HETATM   16  H2  UNL     1      -0.456  -2.606  -1.477  1.00  0.00           H  
HETATM   17  H3  UNL     1       0.083  -1.000  -2.221  1.00  0.00           H  
HETATM   18  H4  UNL     1      -3.271  -2.091  -1.180  1.00  0.00           H  
HETATM   19  H5  UNL     1      -4.653  -0.971   0.495  1.00  0.00           H  
HETATM   20  H6  UNL     1      -3.681   0.909   1.836  1.00  0.00           H  
HETATM   21  H7  UNL     1      -0.639   1.589   2.582  1.00  0.00           H  
HETATM   22  H8  UNL     1      -0.568   2.614   1.054  1.00  0.00           H  
HETATM   23  H9  UNL     1      -2.020   2.587   2.079  1.00  0.00           H  
HETATM   24  H10 UNL     1       0.496   1.306  -0.961  1.00  0.00           H  
HETATM   25  H11 UNL     1       2.885   1.566   0.323  1.00  0.00           H  
HETATM   26  H12 UNL     1       2.825  -0.890  -1.500  1.00  0.00           H  
HETATM   27  H13 UNL     1       4.134   0.371  -1.469  1.00  0.00           H  
HETATM   28  H14 UNL     1       2.423   0.817  -1.861  1.00  0.00           H  
HETATM   29  H15 UNL     1       3.370  -0.236   2.014  1.00  0.00           H  
HETATM   30  H16 UNL     1       3.902  -1.196   0.738  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    3    8
CONECT    3    4   18
CONECT    4    5    5   19
CONECT    5    6   20
CONECT    6    7    8    8
CONECT    7   21   22   23
CONECT    8    9
CONECT    9   10   24
CONECT   10   11   11   12
CONECT   12   13   14   25
CONECT   13   26   27   28
CONECT   14   29   30
END

HMDB0015189
     RDKit          3D
Tocainide
 30 30  0  0  0  0  0  0  0  0999 V2000
   -0.7488   -1.5981   -1.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5497   -0.8838   -0.8089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8588   -1.2806   -0.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6359   -0.6351    0.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0824    0.4020    1.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7806    0.8223    0.9053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1984    1.9401    1.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0425    0.1532   -0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2868    0.5650   -0.2612 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3936    0.0116    0.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2328   -0.8902    1.3189 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7846    0.4716    0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0850    0.1552   -1.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7302   -0.2228    1.0384 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4461   -1.7798   -2.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4557   -2.6057   -1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0827   -1.0003   -2.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2711   -2.0909   -1.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6534   -0.9712    0.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6814    0.9087    1.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6388    1.5891    2.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5680    2.6141    1.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0196    2.5874    2.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4956    1.3062   -0.9612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8855    1.5655    0.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8254   -0.8901   -1.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1337    0.3714   -1.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4234    0.8169   -1.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3695   -0.2357    2.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9022   -1.1960    0.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
  8  2  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  4 19  1  0
  5 20  1  0
  7 21  1  0
  7 22  1  0
  7 23  1  0
  9 24  1  0
 12 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Amino-2',6'-propionoxylidide	ChEBI
2-Amino-N-(2,6-dimethylphenyl)propanamide	ChEBI
2-Amino-N-(2,6-dimethylphenyl)propionamid	ChEBI
Alanyl-2,6-xylidide	ChEBI
Tocainida	ChEBI
Tocainidum	ChEBI
AstraZeneca brand OF tocainide hydrochloride	HMDB
Tocainide hydrochloride	HMDB
Tocainide monohdyrochloride, (R)-isomer	HMDB
Tocainide monohydrobromide, (R)-isomer	HMDB
Tocainide monohydrochloride	HMDB
Tocainide, (+-)-isomer	HMDB
Tocainide, (R)-isomer	HMDB
Tocainide, (S)-isomer	HMDB
Tonocard	HMDB
Tocainide monohydrochloride, (+-)-isomer	HMDB
Tocainide monohydrochloride, (S)-isomer	HMDB
Xylotocan	HMDB
Hydrochloride, tocainide	HMDB

Chemical Formula

C₁₁H₁₆N₂O

Average Molecular Weight

192.2575

Monoisotopic Molecular Weight

192.126263144

IUPAC Name

2-amino-N-(2,6-dimethylphenyl)propanamide

Traditional Name

tocainide

CAS Registry Number

41708-72-9

SMILES

CC(N)C(=O)NC1=C(C)C=CC=C1C

InChI Identifier

InChI=1S/C11H16N2O/c1-7-5-4-6-8(2)10(7)13-11(14)9(3)12/h4-6,9H,12H2,1-3H3,(H,13,14)

InChI Key

BUJAGSGYPOAWEI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as m-xylenes. These are aromatic compounds that contain a m-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 3-positions.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Xylenes

Direct Parent

m-Xylenes

Alternative Parents

Substituents

M-xylene
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:9611 )

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

Extracellular (HMDB: HMDB0015189)
Membrane (HMDB: HMDB0015189)

Source

Exogenous

Exogenous (HMDB: HMDB0015189)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Tocainide Action Pathway (PathBank: SMP0000330)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	246 - 266 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.6 g/L	Not Available
LogP	1.1	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.6 g/L	ALOGPS
logP	0.55	ALOGPS
logP	1.88	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	13.65	ChemAxon
pKa (Strongest Basic)	8.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	55.12 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	58.86 m³·mol⁻¹	ChemAxon
Polarizability	21.59 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]+	145.22	31661259
DarkChem	[M-H]-	142.484	31661259
DeepCCS	[M+H]+	147.166	30932474
DeepCCS	[M-H]-	144.808	30932474
DeepCCS	[M-2H]-	179.348	30932474
DeepCCS	[M+Na]+	153.98	30932474
AllCCS	[M+H]+	144.3	32859911
AllCCS	[M+H-H2O]+	140.2	32859911
AllCCS	[M+NH4]+	148.0	32859911
AllCCS	[M+Na]+	149.1	32859911
AllCCS	[M-H]-	145.8	32859911
AllCCS	[M+Na-2H]-	146.7	32859911
AllCCS	[M+HCOO]-	147.8	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.	2.42 minutes	32390414
Predicted by Siyang on May 30, 2022	9.9719 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.53 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	94.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1036.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	262.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	116.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	47.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	278.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	354.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	186.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	754.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	264.5 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	772.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	204.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	251.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	342.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	371.8 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	186.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tocainide	CC(N)C(=O)NC1=C(C)C=CC=C1C	2494.0	Standard polar	33892256
Tocainide	CC(N)C(=O)NC1=C(C)C=CC=C1C	1703.0	Standard non polar	33892256
Tocainide	CC(N)C(=O)NC1=C(C)C=CC=C1C	1736.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tocainide,1TMS,isomer #1	CC1=CC=CC(C)=C1NC(=O)C(C)N[Si](C)(C)C	1787.5	Semi standard non polar	33892256
Tocainide,1TMS,isomer #1	CC1=CC=CC(C)=C1NC(=O)C(C)N[Si](C)(C)C	1763.5	Standard non polar	33892256
Tocainide,1TMS,isomer #1	CC1=CC=CC(C)=C1NC(=O)C(C)N[Si](C)(C)C	2366.1	Standard polar	33892256
Tocainide,1TMS,isomer #2	CC1=CC=CC(C)=C1N(C(=O)C(C)N)[Si](C)(C)C	1640.5	Semi standard non polar	33892256
Tocainide,1TMS,isomer #2	CC1=CC=CC(C)=C1N(C(=O)C(C)N)[Si](C)(C)C	1762.0	Standard non polar	33892256
Tocainide,1TMS,isomer #2	CC1=CC=CC(C)=C1N(C(=O)C(C)N)[Si](C)(C)C	2417.7	Standard polar	33892256
Tocainide,2TMS,isomer #1	CC1=CC=CC(C)=C1N(C(=O)C(C)N[Si](C)(C)C)[Si](C)(C)C	1752.5	Semi standard non polar	33892256
Tocainide,2TMS,isomer #1	CC1=CC=CC(C)=C1N(C(=O)C(C)N[Si](C)(C)C)[Si](C)(C)C	1810.5	Standard non polar	33892256
Tocainide,2TMS,isomer #1	CC1=CC=CC(C)=C1N(C(=O)C(C)N[Si](C)(C)C)[Si](C)(C)C	2054.9	Standard polar	33892256
Tocainide,2TMS,isomer #2	CC1=CC=CC(C)=C1NC(=O)C(C)N([Si](C)(C)C)[Si](C)(C)C	1945.4	Semi standard non polar	33892256
Tocainide,2TMS,isomer #2	CC1=CC=CC(C)=C1NC(=O)C(C)N([Si](C)(C)C)[Si](C)(C)C	1877.4	Standard non polar	33892256
Tocainide,2TMS,isomer #2	CC1=CC=CC(C)=C1NC(=O)C(C)N([Si](C)(C)C)[Si](C)(C)C	2324.5	Standard polar	33892256
Tocainide,3TMS,isomer #1	CC1=CC=CC(C)=C1N(C(=O)C(C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	1881.4	Semi standard non polar	33892256
Tocainide,3TMS,isomer #1	CC1=CC=CC(C)=C1N(C(=O)C(C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	1943.9	Standard non polar	33892256
Tocainide,3TMS,isomer #1	CC1=CC=CC(C)=C1N(C(=O)C(C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2055.4	Standard polar	33892256
Tocainide,1TBDMS,isomer #1	CC1=CC=CC(C)=C1NC(=O)C(C)N[Si](C)(C)C(C)(C)C	2044.9	Semi standard non polar	33892256
Tocainide,1TBDMS,isomer #1	CC1=CC=CC(C)=C1NC(=O)C(C)N[Si](C)(C)C(C)(C)C	1984.4	Standard non polar	33892256
Tocainide,1TBDMS,isomer #1	CC1=CC=CC(C)=C1NC(=O)C(C)N[Si](C)(C)C(C)(C)C	2467.2	Standard polar	33892256
Tocainide,1TBDMS,isomer #2	CC1=CC=CC(C)=C1N(C(=O)C(C)N)[Si](C)(C)C(C)(C)C	1874.4	Semi standard non polar	33892256
Tocainide,1TBDMS,isomer #2	CC1=CC=CC(C)=C1N(C(=O)C(C)N)[Si](C)(C)C(C)(C)C	1955.5	Standard non polar	33892256
Tocainide,1TBDMS,isomer #2	CC1=CC=CC(C)=C1N(C(=O)C(C)N)[Si](C)(C)C(C)(C)C	2503.6	Standard polar	33892256
Tocainide,2TBDMS,isomer #1	CC1=CC=CC(C)=C1N(C(=O)C(C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2203.0	Semi standard non polar	33892256
Tocainide,2TBDMS,isomer #1	CC1=CC=CC(C)=C1N(C(=O)C(C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2232.8	Standard non polar	33892256
Tocainide,2TBDMS,isomer #1	CC1=CC=CC(C)=C1N(C(=O)C(C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2325.9	Standard polar	33892256
Tocainide,2TBDMS,isomer #2	CC1=CC=CC(C)=C1NC(=O)C(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2406.0	Semi standard non polar	33892256
Tocainide,2TBDMS,isomer #2	CC1=CC=CC(C)=C1NC(=O)C(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2277.6	Standard non polar	33892256
Tocainide,2TBDMS,isomer #2	CC1=CC=CC(C)=C1NC(=O)C(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2487.9	Standard polar	33892256
Tocainide,3TBDMS,isomer #1	CC1=CC=CC(C)=C1N(C(=O)C(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2607.6	Semi standard non polar	33892256
Tocainide,3TBDMS,isomer #1	CC1=CC=CC(C)=C1N(C(=O)C(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2532.5	Standard non polar	33892256
Tocainide,3TBDMS,isomer #1	CC1=CC=CC(C)=C1N(C(=O)C(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2398.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tocainide GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9700000000-90d7f8cfadbf5c481615	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tocainide 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 - Tocainide LC-ESI-qTof , Positive-QTOF	splash10-004i-0510000090-3faef8c50f47e62f2ac1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tocainide , positive-QTOF	splash10-00dl-0900000000-e3e09337d1b754b4c59c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tocainide 35V, Positive-QTOF	splash10-0006-9400000000-578c55abffed08967f95	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tocainide 10V, Positive-QTOF	splash10-006x-1900000000-c7d5dc77b594bd4bfb29	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tocainide 20V, Positive-QTOF	splash10-00dl-8900000000-54724c25ef578bc89366	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tocainide 40V, Positive-QTOF	splash10-006x-9500000000-794c0ef462fb9d8c4369	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tocainide 10V, Negative-QTOF	splash10-0006-0900000000-700b3726d7cb4618c003	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tocainide 20V, Negative-QTOF	splash10-00dl-2900000000-4e4c7ecdb9ff631f04ea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tocainide 40V, Negative-QTOF	splash10-00xr-3900000000-01c23922110972f5982f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tocainide 10V, Positive-QTOF	splash10-006x-0900000000-32ecf76928a4f2d8612f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tocainide 20V, Positive-QTOF	splash10-0006-9800000000-6806af9483651aae91f1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tocainide 40V, Positive-QTOF	splash10-0006-9100000000-39dc3374e1a4d42414ac	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tocainide 10V, Negative-QTOF	splash10-0006-0900000000-4dd4451b1f851e3d0321	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tocainide 20V, Negative-QTOF	splash10-0006-1900000000-6ddceb9e7f7ebd980bdd	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tocainide 40V, Negative-QTOF	splash10-014i-4900000000-2d6249a6af4ddf806fba	2021-10-11	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Tocainide 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 DB01056	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01056	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01056

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

35632

KEGG Compound ID

C07142

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tocainide

METLIN ID

Not Available

PubChem Compound

38945

PDB ID

Not Available

ChEBI ID

9611

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. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

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

2. 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

Georgijevic Milic L: [Molecular genetics in the hereditary form of long QT syndrome]. Med Pregl. 2000 Jan-Feb;53(1-2):51-4. [PubMed:10953551 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Tocainide (HMDB0015189)

MOL for HMDB0015189 (Tocainide)

3D MOL for HMDB0015189 (Tocainide)

3D SDF for HMDB0015189 (Tocainide)

3D-SDF for HMDB0015189 (Tocainide)

PDB for HMDB0015189 (Tocainide)

3D PDB for HMDB0015189 (Tocainide)

SMILES for HMDB0015189 (Tocainide)

INCHI for HMDB0015189 (Tocainide)

Structure for HMDB0015189 (Tocainide)

3D Structure for HMDB0015189 (Tocainide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

References

References