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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:55 UTC

HMDB ID

HMDB0015263

Secondary Accession Numbers

HMDB15263

Metabolite Identification

Common Name

Proguanil

Description

Proguanil, also known as chloroguanide, belongs to the class of organic compounds known as 1-arylbiguanides. These are organonitrogen compounds containing a biguanide that is N-arylsubstituted at only the 1-position. Proguanil is a drug which is used for the causal prevention and suppression of malaria caused by susceptible strains of p. falciparum and other species of plasmodium found in some geographical areas of the world. Proguanil is a very strong basic compound (based on its pKa).

Structure

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

HMDB0015263
     RDKit          3D
Proguanil
 33 33  0  0  0  0  0  0  0  0999 V2000
   -4.4460    1.2499    0.9866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6656    0.0972    0.3629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6359   -1.0960    1.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3196    0.5792    0.1465 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6982    0.3666   -0.9482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3262   -0.3547   -1.9822 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903    0.8518   -1.1198 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6636    0.1158   -1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4842   -1.2903   -1.1410 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9184    0.7477   -1.3865 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9627    0.4865   -0.4574 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7789   -0.3705    0.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8101   -0.6212    1.5155 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0429   -0.0208    1.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3717   -0.2970    2.4809 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2278    0.8326    0.3154 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2050    1.0749   -0.5760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2563    1.2377    2.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1200    2.2003    0.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5158    1.1365    0.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1591   -0.1066   -0.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6274   -1.3098    1.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3636   -1.0365    2.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933   -1.9910    0.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9742    0.1744   -2.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2071   -1.3659   -2.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0218   -1.8599   -1.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1161   -1.7683   -0.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1189    1.4076   -2.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8345   -0.8768    0.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6758   -1.2948    2.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1943    1.3344    0.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4038    1.7671   -1.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  3
  8  9  1  0
  8 10  1  0
 10 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
  3 22  1  0
  3 23  1  0
  3 24  1  0
  6 25  1  0
  6 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 16 32  1  0
 17 33  1  0
M  END

1131
  Mrv0541 02231215162D          

 17 17  0  0  0  0            999 V2000
    2.3645   -3.0154    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    1.5221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.2846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.5221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    2.7596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    0.2846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    1.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    2.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    1.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  2  7  1  0  0  0  0
  2 11  2  0  0  0  0
  3 10  1  0  0  0  0
  3 14  1  0  0  0  0
  4 11  1  0  0  0  0
  4 14  2  3  0  0  0
  5 11  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10 12  2  0  0  0  0
 10 13  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 15 17  2  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015263

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H16ClN5/c1-7(2)15-10(13)17-11(14)16-9-5-3-8(12)4-6-9/h3-7H,1-2H3,(H5,13,14,15,16,17)

> <INCHI_KEY>
SSOLNOMRVKKSON-UHFFFAOYSA-N

> <FORMULA>
C11H16ClN5

> <MOLECULAR_WEIGHT>
253.731

> <EXACT_MASS>
253.109423244

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.84067113141314

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(E)-1-({amino[(4-chlorophenyl)amino]methylidene}amino)-N'-(propan-2-yl)methenimidamide

> <ALOGPS_LOGP>
1.90

> <JCHEM_LOGP>
1.8874301803333333

> <ALOGPS_LOGS>
-2.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.76859708058674

> <JCHEM_PKA_STRONGEST_BASIC>
10.122047373021262

> <JCHEM_POLAR_SURFACE_AREA>
88.78999999999999

> <JCHEM_REFRACTIVITY>
71.0676

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.86e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
proguanil

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015263
     RDKit          3D
Proguanil
 33 33  0  0  0  0  0  0  0  0999 V2000
   -4.4460    1.2499    0.9866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6656    0.0972    0.3629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6359   -1.0960    1.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3196    0.5792    0.1465 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6982    0.3666   -0.9482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3262   -0.3547   -1.9822 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903    0.8518   -1.1198 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6636    0.1158   -1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4842   -1.2903   -1.1410 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9184    0.7477   -1.3865 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9627    0.4865   -0.4574 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7789   -0.3705    0.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8101   -0.6212    1.5155 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0429   -0.0208    1.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3717   -0.2970    2.4809 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2278    0.8326    0.3154 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2050    1.0749   -0.5760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2563    1.2377    2.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1200    2.2003    0.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5158    1.1365    0.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1591   -0.1066   -0.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6274   -1.3098    1.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3636   -1.0365    2.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933   -1.9910    0.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9742    0.1744   -2.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2071   -1.3659   -2.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0218   -1.8599   -1.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1161   -1.7683   -0.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1189    1.4076   -2.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8345   -0.8768    0.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6758   -1.2948    2.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1943    1.3344    0.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4038    1.7671   -1.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  3
  8  9  1  0
  8 10  1  0
 10 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
  3 22  1  0
  3 23  1  0
  3 24  1  0
  6 25  1  0
  6 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 16 32  1  0
 17 33  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1131                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       4.414  -5.629   0.000  0.00  0.00          Cl+0
HETATM    2  N   UNK     0       8.415   2.841   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       4.414   0.531   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       5.747   2.841   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       7.081   5.151   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       7.081   0.531   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       9.748   3.611   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.748   5.151   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.082   2.841   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -1.009   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081   3.611   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.747  -1.779   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080  -1.779   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.747   1.301   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.747  -3.319   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.080  -3.319   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -4.089   0.000  0.00  0.00           C+0
CONECT    1   17                                                            
CONECT    2    7   11                                                       
CONECT    3   10   14                                                       
CONECT    4   11   14                                                       
CONECT    5   11                                                            
CONECT    6   14                                                            
CONECT    7    2    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    3   12   13                                                  
CONECT   11    2    4    5                                                  
CONECT   12   10   15                                                       
CONECT   13   10   16                                                       
CONECT   14    3    4    6                                                  
CONECT   15   12   17                                                       
CONECT   16   13   17                                                       
CONECT   17    1   15   16                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0015263
HETATM    1  C1  UNL     1      -4.446   1.250   0.987  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.666   0.097   0.363  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.636  -1.096   1.260  1.00  0.00           C  
HETATM    4  N1  UNL     1      -2.320   0.579   0.146  1.00  0.00           N  
HETATM    5  C4  UNL     1      -1.698   0.367  -0.948  1.00  0.00           C  
HETATM    6  N2  UNL     1      -2.326  -0.355  -1.982  1.00  0.00           N  
HETATM    7  N3  UNL     1      -0.390   0.852  -1.120  1.00  0.00           N  
HETATM    8  C5  UNL     1       0.664   0.116  -1.215  1.00  0.00           C  
HETATM    9  N4  UNL     1       0.484  -1.290  -1.141  1.00  0.00           N  
HETATM   10  N5  UNL     1       1.918   0.748  -1.386  1.00  0.00           N  
HETATM   11  C6  UNL     1       2.963   0.486  -0.457  1.00  0.00           C  
HETATM   12  C7  UNL     1       2.779  -0.371   0.608  1.00  0.00           C  
HETATM   13  C8  UNL     1       3.810  -0.621   1.515  1.00  0.00           C  
HETATM   14  C9  UNL     1       5.043  -0.021   1.375  1.00  0.00           C  
HETATM   15 CL1  UNL     1       6.372  -0.297   2.481  1.00  0.00          CL  
HETATM   16  C10 UNL     1       5.228   0.833   0.315  1.00  0.00           C  
HETATM   17  C11 UNL     1       4.205   1.075  -0.576  1.00  0.00           C  
HETATM   18  H1  UNL     1      -4.256   1.238   2.068  1.00  0.00           H  
HETATM   19  H2  UNL     1      -4.120   2.200   0.514  1.00  0.00           H  
HETATM   20  H3  UNL     1      -5.516   1.137   0.801  1.00  0.00           H  
HETATM   21  H4  UNL     1      -4.159  -0.107  -0.614  1.00  0.00           H  
HETATM   22  H5  UNL     1      -2.627  -1.310   1.677  1.00  0.00           H  
HETATM   23  H6  UNL     1      -4.364  -1.037   2.092  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.893  -1.991   0.626  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.974   0.174  -2.617  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.207  -1.366  -2.175  1.00  0.00           H  
HETATM   27  H10 UNL     1       1.022  -1.860  -1.856  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.116  -1.768  -0.457  1.00  0.00           H  
HETATM   29  H12 UNL     1       2.119   1.408  -2.175  1.00  0.00           H  
HETATM   30  H13 UNL     1       1.835  -0.877   0.778  1.00  0.00           H  
HETATM   31  H14 UNL     1       3.676  -1.295   2.359  1.00  0.00           H  
HETATM   32  H15 UNL     1       6.194   1.334   0.163  1.00  0.00           H  
HETATM   33  H16 UNL     1       4.404   1.767  -1.409  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4   21
CONECT    3   22   23   24
CONECT    4    5    5
CONECT    5    6    7
CONECT    6   25   26
CONECT    7    8    8
CONECT    8    9   10
CONECT    9   27   28
CONECT   10   11   29
CONECT   11   12   12   17
CONECT   12   13   30
CONECT   13   14   14   31
CONECT   14   15   16
CONECT   16   17   17   32
CONECT   17   33
END

HMDB0015263
     RDKit          3D
Proguanil
 33 33  0  0  0  0  0  0  0  0999 V2000
   -4.4460    1.2499    0.9866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6656    0.0972    0.3629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6359   -1.0960    1.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3196    0.5792    0.1465 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6982    0.3666   -0.9482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3262   -0.3547   -1.9822 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903    0.8518   -1.1198 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6636    0.1158   -1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4842   -1.2903   -1.1410 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9184    0.7477   -1.3865 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9627    0.4865   -0.4574 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7789   -0.3705    0.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8101   -0.6212    1.5155 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0429   -0.0208    1.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3717   -0.2970    2.4809 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2278    0.8326    0.3154 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2050    1.0749   -0.5760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2563    1.2377    2.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1200    2.2003    0.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5158    1.1365    0.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1591   -0.1066   -0.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6274   -1.3098    1.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3636   -1.0365    2.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933   -1.9910    0.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9742    0.1744   -2.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2071   -1.3659   -2.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0218   -1.8599   -1.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1161   -1.7683   -0.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1189    1.4076   -2.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8345   -0.8768    0.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6758   -1.2948    2.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1943    1.3344    0.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4038    1.7671   -1.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  3
  8  9  1  0
  8 10  1  0
 10 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
  3 22  1  0
  3 23  1  0
  3 24  1  0
  6 25  1  0
  6 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 16 32  1  0
 17 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(p-Chlorophenyl)-5-isopropylbiguanide	ChEBI
Chlorguanide	ChEBI
Chloroguanide	ChEBI
N-(4-Chlorophenyl)-n'-(isopropyl)-imidodicarbonimidic diamide	ChEBI
Proguanilum	ChEBI

Chemical Formula

C₁₁H₁₆ClN₅

Average Molecular Weight

253.731

Monoisotopic Molecular Weight

253.109423244

IUPAC Name

(E)-1-({amino[(4-chlorophenyl)amino]methylidene}amino)-N'-(propan-2-yl)methenimidamide

Traditional Name

proguanil

CAS Registry Number

500-92-5

SMILES

CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C11H16ClN5/c1-7(2)15-10(13)17-11(14)16-9-5-3-8(12)4-6-9/h3-7H,1-2H3,(H5,13,14,15,16,17)

InChI Key

SSOLNOMRVKKSON-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-arylbiguanides. These are organonitrogen compounds containing a biguanide that is N-arylsubstituted at only the 1-position.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Guanidines

Direct Parent

1-arylbiguanides

Alternative Parents

Substituents

1-arylbiguanide
Halobenzene
Chlorobenzene
Benzenoid
Monocyclic benzene moiety
Aryl halide
Aryl chloride
Carboximidamide
Organopnictogen compound
Hydrocarbon derivative
Organochloride
Organohalogen compound
Imine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monochlorobenzenes (CHEBI:8455 )
biguanides (CHEBI:8455 )

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

Membrane (HMDB: HMDB0015263)

Source

Exogenous

Exogenous (HMDB: HMDB0015263)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	129 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.29 g/L	Not Available
LogP	1.8	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	161.3	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.29 g/L	ALOGPS
logP	1.9	ALOGPS
logP	1.89	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	19.77	ChemAxon
pKa (Strongest Basic)	10.12	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	88.79 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	71.07 m³·mol⁻¹	ChemAxon
Polarizability	26.84 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	169.486	30932474
DeepCCS	[M-H]-	167.129	30932474
DeepCCS	[M-2H]-	200.015	30932474
DeepCCS	[M+Na]+	175.58	30932474
AllCCS	[M+H]+	156.8	32859911
AllCCS	[M+H-H2O]+	153.3	32859911
AllCCS	[M+NH4]+	159.9	32859911
AllCCS	[M+Na]+	160.8	32859911
AllCCS	[M-H]-	158.7	32859911
AllCCS	[M+Na-2H]-	159.4	32859911
AllCCS	[M+HCOO]-	160.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Proguanil	CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1	3332.8	Standard polar	33892256
Proguanil	CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1	1954.4	Standard non polar	33892256
Proguanil	CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1	2452.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Proguanil,1TMS,isomer #1	CC(C)/N=C(/N=C(N)NC1=CC=C(Cl)C=C1)N[Si](C)(C)C	2418.1	Semi standard non polar	33892256
Proguanil,1TMS,isomer #1	CC(C)/N=C(/N=C(N)NC1=CC=C(Cl)C=C1)N[Si](C)(C)C	2178.3	Standard non polar	33892256
Proguanil,1TMS,isomer #1	CC(C)/N=C(/N=C(N)NC1=CC=C(Cl)C=C1)N[Si](C)(C)C	4055.1	Standard polar	33892256
Proguanil,1TMS,isomer #2	CC(C)/N=C(\N)N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C	2431.9	Semi standard non polar	33892256
Proguanil,1TMS,isomer #2	CC(C)/N=C(\N)N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C	2140.7	Standard non polar	33892256
Proguanil,1TMS,isomer #2	CC(C)/N=C(\N)N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C	4092.3	Standard polar	33892256
Proguanil,1TMS,isomer #3	CC(C)/N=C(\N)N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C	2248.3	Semi standard non polar	33892256
Proguanil,1TMS,isomer #3	CC(C)/N=C(\N)N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C	2143.4	Standard non polar	33892256
Proguanil,1TMS,isomer #3	CC(C)/N=C(\N)N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C	4083.9	Standard polar	33892256
Proguanil,2TMS,isomer #1	CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C)N[Si](C)(C)C	2482.5	Semi standard non polar	33892256
Proguanil,2TMS,isomer #1	CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C)N[Si](C)(C)C	2096.2	Standard non polar	33892256
Proguanil,2TMS,isomer #1	CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C)N[Si](C)(C)C	3758.8	Standard polar	33892256
Proguanil,2TMS,isomer #2	CC(C)/N=C(/N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N[Si](C)(C)C	2312.1	Semi standard non polar	33892256
Proguanil,2TMS,isomer #2	CC(C)/N=C(/N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N[Si](C)(C)C	2189.0	Standard non polar	33892256
Proguanil,2TMS,isomer #2	CC(C)/N=C(/N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N[Si](C)(C)C	3750.2	Standard polar	33892256
Proguanil,2TMS,isomer #3	CC(C)/N=C(/N=C(N)NC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2422.1	Semi standard non polar	33892256
Proguanil,2TMS,isomer #3	CC(C)/N=C(/N=C(N)NC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2217.8	Standard non polar	33892256
Proguanil,2TMS,isomer #3	CC(C)/N=C(/N=C(N)NC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C	3802.8	Standard polar	33892256
Proguanil,2TMS,isomer #4	CC(C)/N=C(\N)N=C(N[Si](C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C	2294.4	Semi standard non polar	33892256
Proguanil,2TMS,isomer #4	CC(C)/N=C(\N)N=C(N[Si](C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C	2126.5	Standard non polar	33892256
Proguanil,2TMS,isomer #4	CC(C)/N=C(\N)N=C(N[Si](C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C	3786.2	Standard polar	33892256
Proguanil,2TMS,isomer #5	CC(C)/N=C(\N)N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2429.6	Semi standard non polar	33892256
Proguanil,2TMS,isomer #5	CC(C)/N=C(\N)N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2201.5	Standard non polar	33892256
Proguanil,2TMS,isomer #5	CC(C)/N=C(\N)N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C	3926.7	Standard polar	33892256
Proguanil,3TMS,isomer #1	CC(C)/N=C(/N=C(N[Si](C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N[Si](C)(C)C	2347.6	Semi standard non polar	33892256
Proguanil,3TMS,isomer #1	CC(C)/N=C(/N=C(N[Si](C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N[Si](C)(C)C	2181.4	Standard non polar	33892256
Proguanil,3TMS,isomer #1	CC(C)/N=C(/N=C(N[Si](C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N[Si](C)(C)C	3346.5	Standard polar	33892256
Proguanil,3TMS,isomer #2	CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C	2469.1	Semi standard non polar	33892256
Proguanil,3TMS,isomer #2	CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C	2123.3	Standard non polar	33892256
Proguanil,3TMS,isomer #2	CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C	3495.2	Standard polar	33892256
Proguanil,3TMS,isomer #3	CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2531.6	Semi standard non polar	33892256
Proguanil,3TMS,isomer #3	CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2128.0	Standard non polar	33892256
Proguanil,3TMS,isomer #3	CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3385.9	Standard polar	33892256
Proguanil,3TMS,isomer #4	CC(C)/N=C(/N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2368.5	Semi standard non polar	33892256
Proguanil,3TMS,isomer #4	CC(C)/N=C(/N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2274.0	Standard non polar	33892256
Proguanil,3TMS,isomer #4	CC(C)/N=C(/N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3528.4	Standard polar	33892256
Proguanil,3TMS,isomer #5	CC(C)/N=C(\N)N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2286.5	Semi standard non polar	33892256
Proguanil,3TMS,isomer #5	CC(C)/N=C(\N)N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2318.8	Standard non polar	33892256
Proguanil,3TMS,isomer #5	CC(C)/N=C(\N)N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3650.6	Standard polar	33892256
Proguanil,4TMS,isomer #1	CC(C)/N=C(/N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C	2390.7	Semi standard non polar	33892256
Proguanil,4TMS,isomer #1	CC(C)/N=C(/N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C	2301.9	Standard non polar	33892256
Proguanil,4TMS,isomer #1	CC(C)/N=C(/N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C	3097.4	Standard polar	33892256
Proguanil,4TMS,isomer #2	CC(C)/N=C(/N=C(N[Si](C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2441.4	Semi standard non polar	33892256
Proguanil,4TMS,isomer #2	CC(C)/N=C(/N=C(N[Si](C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2269.7	Standard non polar	33892256
Proguanil,4TMS,isomer #2	CC(C)/N=C(/N=C(N[Si](C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3010.7	Standard polar	33892256
Proguanil,4TMS,isomer #3	CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2550.3	Semi standard non polar	33892256
Proguanil,4TMS,isomer #3	CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2176.6	Standard non polar	33892256
Proguanil,4TMS,isomer #3	CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3162.5	Standard polar	33892256
Proguanil,5TMS,isomer #1	CC(C)/N=C(/N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2529.6	Semi standard non polar	33892256
Proguanil,5TMS,isomer #1	CC(C)/N=C(/N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2378.3	Standard non polar	33892256
Proguanil,5TMS,isomer #1	CC(C)/N=C(/N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2817.3	Standard polar	33892256
Proguanil,1TBDMS,isomer #1	CC(C)/N=C(/N=C(N)NC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C	2576.9	Semi standard non polar	33892256
Proguanil,1TBDMS,isomer #1	CC(C)/N=C(/N=C(N)NC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C	2316.4	Standard non polar	33892256
Proguanil,1TBDMS,isomer #1	CC(C)/N=C(/N=C(N)NC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C	4032.5	Standard polar	33892256
Proguanil,1TBDMS,isomer #2	CC(C)/N=C(\N)N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C	2621.8	Semi standard non polar	33892256
Proguanil,1TBDMS,isomer #2	CC(C)/N=C(\N)N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C	2275.3	Standard non polar	33892256
Proguanil,1TBDMS,isomer #2	CC(C)/N=C(\N)N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C	4063.8	Standard polar	33892256
Proguanil,1TBDMS,isomer #3	CC(C)/N=C(\N)N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	2422.3	Semi standard non polar	33892256
Proguanil,1TBDMS,isomer #3	CC(C)/N=C(\N)N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	2357.0	Standard non polar	33892256
Proguanil,1TBDMS,isomer #3	CC(C)/N=C(\N)N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	4116.6	Standard polar	33892256
Proguanil,2TBDMS,isomer #1	CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	2860.7	Semi standard non polar	33892256
Proguanil,2TBDMS,isomer #1	CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	2422.7	Standard non polar	33892256
Proguanil,2TBDMS,isomer #1	CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3659.5	Standard polar	33892256
Proguanil,2TBDMS,isomer #2	CC(C)/N=C(/N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	2698.6	Semi standard non polar	33892256
Proguanil,2TBDMS,isomer #2	CC(C)/N=C(/N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	2535.3	Standard non polar	33892256
Proguanil,2TBDMS,isomer #2	CC(C)/N=C(/N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3740.4	Standard polar	33892256
Proguanil,2TBDMS,isomer #3	CC(C)/N=C(/N=C(N)NC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2780.3	Semi standard non polar	33892256
Proguanil,2TBDMS,isomer #3	CC(C)/N=C(/N=C(N)NC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2552.1	Standard non polar	33892256
Proguanil,2TBDMS,isomer #3	CC(C)/N=C(/N=C(N)NC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3764.3	Standard polar	33892256
Proguanil,2TBDMS,isomer #4	CC(C)/N=C(\N)N=C(N[Si](C)(C)C(C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	2683.6	Semi standard non polar	33892256
Proguanil,2TBDMS,isomer #4	CC(C)/N=C(\N)N=C(N[Si](C)(C)C(C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	2536.9	Standard non polar	33892256
Proguanil,2TBDMS,isomer #4	CC(C)/N=C(\N)N=C(N[Si](C)(C)C(C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	3807.7	Standard polar	33892256
Proguanil,2TBDMS,isomer #5	CC(C)/N=C(\N)N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2790.8	Semi standard non polar	33892256
Proguanil,2TBDMS,isomer #5	CC(C)/N=C(\N)N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2589.8	Standard non polar	33892256
Proguanil,2TBDMS,isomer #5	CC(C)/N=C(\N)N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3897.1	Standard polar	33892256
Proguanil,3TBDMS,isomer #1	CC(C)/N=C(/N=C(N[Si](C)(C)C(C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	2947.6	Semi standard non polar	33892256
Proguanil,3TBDMS,isomer #1	CC(C)/N=C(/N=C(N[Si](C)(C)C(C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	2653.4	Standard non polar	33892256
Proguanil,3TBDMS,isomer #1	CC(C)/N=C(/N=C(N[Si](C)(C)C(C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3382.1	Standard polar	33892256
Proguanil,3TBDMS,isomer #2	CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3064.2	Semi standard non polar	33892256
Proguanil,3TBDMS,isomer #2	CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	2712.2	Standard non polar	33892256
Proguanil,3TBDMS,isomer #2	CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3480.2	Standard polar	33892256
Proguanil,3TBDMS,isomer #3	CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3086.2	Semi standard non polar	33892256
Proguanil,3TBDMS,isomer #3	CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2679.1	Standard non polar	33892256
Proguanil,3TBDMS,isomer #3	CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3382.3	Standard polar	33892256
Proguanil,3TBDMS,isomer #4	CC(C)/N=C(/N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2958.2	Semi standard non polar	33892256
Proguanil,3TBDMS,isomer #4	CC(C)/N=C(/N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2735.9	Standard non polar	33892256
Proguanil,3TBDMS,isomer #4	CC(C)/N=C(/N=C(N)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3594.6	Standard polar	33892256
Proguanil,3TBDMS,isomer #5	CC(C)/N=C(\N)N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2962.0	Semi standard non polar	33892256
Proguanil,3TBDMS,isomer #5	CC(C)/N=C(\N)N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2827.1	Standard non polar	33892256
Proguanil,3TBDMS,isomer #5	CC(C)/N=C(\N)N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3716.4	Standard polar	33892256
Proguanil,4TBDMS,isomer #1	CC(C)/N=C(/N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3234.1	Semi standard non polar	33892256
Proguanil,4TBDMS,isomer #1	CC(C)/N=C(/N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	2961.6	Standard non polar	33892256
Proguanil,4TBDMS,isomer #1	CC(C)/N=C(/N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3277.3	Standard polar	33892256
Proguanil,4TBDMS,isomer #2	CC(C)/N=C(/N=C(N[Si](C)(C)C(C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3202.8	Semi standard non polar	33892256
Proguanil,4TBDMS,isomer #2	CC(C)/N=C(/N=C(N[Si](C)(C)C(C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2918.0	Standard non polar	33892256
Proguanil,4TBDMS,isomer #2	CC(C)/N=C(/N=C(N[Si](C)(C)C(C)(C)C)N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3213.8	Standard polar	33892256
Proguanil,4TBDMS,isomer #3	CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3321.0	Semi standard non polar	33892256
Proguanil,4TBDMS,isomer #3	CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2964.8	Standard non polar	33892256
Proguanil,4TBDMS,isomer #3	CC(C)/N=C(/N=C(NC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3287.5	Standard polar	33892256
Proguanil,5TBDMS,isomer #1	CC(C)/N=C(/N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3502.7	Semi standard non polar	33892256
Proguanil,5TBDMS,isomer #1	CC(C)/N=C(/N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3242.3	Standard non polar	33892256
Proguanil,5TBDMS,isomer #1	CC(C)/N=C(/N=C(N(C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3123.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Proguanil GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9820000000-cb5312c89efbffe9e258	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Proguanil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Proguanil 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 - Proguanil 10V, Positive-QTOF	splash10-0udi-0690000000-77111e4056e6fd55dd00	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proguanil 20V, Positive-QTOF	splash10-0h90-2920000000-d8728ebf8c07ca389fa5	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proguanil 40V, Positive-QTOF	splash10-0h93-7900000000-fd5b681d853f5a600e4e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proguanil 10V, Negative-QTOF	splash10-0udi-4890000000-9cd845da8e9126cab5cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proguanil 20V, Negative-QTOF	splash10-0kdi-5930000000-180eb772ddf87acf8839	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proguanil 40V, Negative-QTOF	splash10-056u-9700000000-782e67963a3309771479	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proguanil 10V, Positive-QTOF	splash10-0udi-0490000000-68ae471c348c1e55ed83	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proguanil 20V, Positive-QTOF	splash10-0fka-2910000000-8cebe23f69e7fa7655c2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proguanil 40V, Positive-QTOF	splash10-0fb9-4900000000-2b8c7a01743760b29b3e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proguanil 10V, Negative-QTOF	splash10-0f8d-4900000000-3f8bd7947322c308f710	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proguanil 20V, Negative-QTOF	splash10-0ue9-5900000000-ca547f95f87c9d9ebe7a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proguanil 40V, Negative-QTOF	splash10-001i-9200000000-81212b3c9362bcd2da62	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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 DB01131	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01131	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01131

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4754

KEGG Compound ID

C07631

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Proguanil

METLIN ID

Not Available

PubChem Compound

4923

PDB ID

Not Available

ChEBI ID

8455

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. Dihydrofolate reductase

General function:: Involved in dihydrofolate reductase activity
Specific function:: Key enzyme in folate metabolism. Contributes to the de novo mitochondrial thymidylate biosynthesis pathway. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA precursor synthesis. Binds its own mRNA and that of DHFRL1.
Gene Name:: DHFR
Uniprot ID:: P00374
Molecular weight:: 21452.61

References

Kaneko A, Bergqvist Y, Takechi M, Kalkoa M, Kaneko O, Kobayakawa T, Ishizaki T, Bjorkman A: Intrinsic efficacy of proguanil against falciparum and vivax malaria independent of the metabolite cycloguanil. J Infect Dis. 1999 Apr;179(4):974-9. [PubMed:10068594 ]
Vasconcelos KF, Plowe CV, Fontes CJ, Kyle D, Wirth DF, Pereira da Silva LH, Zalis MG: Mutations in Plasmodium falciparum dihydrofolate reductase and dihydropteroate synthase of isolates from the Amazon region of Brazil. Mem Inst Oswaldo Cruz. 2000 Sep-Oct;95(5):721-8. [PubMed:10998224 ]
Tahar R, de Pecoulas PE, Basco LK, Chiadmi M, Mazabraud A: Kinetic properties of dihydrofolate reductase from wild-type and mutant Plasmodium vivax expressed in Escherichia coli. Mol Biochem Parasitol. 2001 Apr 6;113(2):241-9. [PubMed:11295178 ]
Durand R, Jafari S, Bouchaud O, Ralaimazava P, Keundjian A, Le Bras J: Plasmodium falciparum: pfcrt and DHFR mutations are associated with failure of chloroquine plus proguanil prophylaxis in travelers. J Infect Dis. 2001 Dec 15;184(12):1633-4. [PubMed:11740746 ]
Le Bras J, Durand R: The mechanisms of resistance to antimalarial drugs in Plasmodium falciparum. Fundam Clin Pharmacol. 2003 Apr;17(2):147-53. [PubMed:12667224 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. Cytochrome P450 3A4

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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

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

3. Cytochrome P450 2C9

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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

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

4. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Lu AH, Shu Y, Huang SL, Wang W, Ou-Yang DS, Zhou HH: In vitro proguanil activation to cycloguanil is mediated by CYP2C19 and CYP3A4 in adult Chinese liver microsomes. Acta Pharmacol Sin. 2000 Aug;21(8):747-52. [PubMed:11501186 ]
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

5. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

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

6. 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

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

7. 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 ]

Showing metabocard for Proguanil (HMDB0015263)

MOL for HMDB0015263 (Proguanil)

3D MOL for HMDB0015263 (Proguanil)

3D SDF for HMDB0015263 (Proguanil)

3D-SDF for HMDB0015263 (Proguanil)

PDB for HMDB0015263 (Proguanil)

3D PDB for HMDB0015263 (Proguanil)

SMILES for HMDB0015263 (Proguanil)

INCHI for HMDB0015263 (Proguanil)

Structure for HMDB0015263 (Proguanil)

3D Structure for HMDB0015263 (Proguanil)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

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References

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References