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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:03 UTC

HMDB ID

HMDB0015641

Secondary Accession Numbers

HMDB15641

Metabolite Identification

Common Name

Dabigatran etexilate

Description

Dabigatran etexilate is an oral prodrug that is metabolized by a serum esterase to dabigatran. It is a synthetic, competitive and reversible direct thrombin inhibitor. Inhibition of thrombin disrupts the coagulation cascade and inhibits the formation of clots. Dabigatran etexilate may be used to decrease the risk of venous thromboembolic events in patients who have undergone total hip or knee replacement surgery, or to prevent stroke and systemic embolism in patients with atrial fibrillation, in whom anticoagulation therapy is indicated.

Structure

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

  Mrv0541 02241212382D          

 46 49  0  0  0  0            999 V2000
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 11 46  1  0  0  0  0
M  END

HMDB0015641
     RDKit          3D
Dabigatran etexilate
 87 90  0  0  0  0  0  0  0  0999 V2000
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M  END

  Mrv0541 02241212382D          

 46 49  0  0  0  0            999 V2000
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   -3.7445    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5695    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1447    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2195    3.4914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  8  1  4  0  0  0
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 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 40 45  1  0  0  0  0
 11 46  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015641

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCOC(=O)N=C(N)C1=CC=C(NCC2=NC3=C(C=CC(=C3)C(=O)N(CCC(=O)OCC)C3=CC=CC=N3)N2C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C34H41N7O5/c1-4-6-7-10-21-46-34(44)39-32(35)24-12-15-26(16-13-24)37-23-30-38-27-22-25(14-17-28(27)40(30)3)33(43)41(20-18-31(42)45-5-2)29-11-8-9-19-36-29/h8-9,11-17,19,22,37H,4-7,10,18,20-21,23H2,1-3H3,(H2,35,39,44)

> <INCHI_KEY>
KSGXQBZTULBEEQ-UHFFFAOYSA-N

> <FORMULA>
C34H41N7O5

> <MOLECULAR_WEIGHT>
627.7332

> <EXACT_MASS>
627.316917457

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
71.1146649339797

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl 3-(1-{2-[({4-[amino({[(hexyloxy)carbonyl]imino})methyl]phenyl}amino)methyl]-1-methyl-1H-1,3-benzodiazol-5-yl}-N-(pyridin-2-yl)formamido)propanoate

> <ALOGPS_LOGP>
5.17

> <JCHEM_LOGP>
4.593332732

> <ALOGPS_LOGS>
-5.13

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.89048494137254

> <JCHEM_PKA_STRONGEST_BASIC>
3.86977496210892

> <JCHEM_POLAR_SURFACE_AREA>
154.03

> <JCHEM_REFRACTIVITY>
176.429

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.66e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dabigatran etexilate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015641
     RDKit          3D
Dabigatran etexilate
 87 90  0  0  0  0  0  0  0  0999 V2000
   14.4370   -0.3695   -1.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.7200   -1.4111    1.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.6149   -2.3465    0.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8828   -2.1166    2.9323 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3341   -1.4609   -3.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1636   -1.8906   -1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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 46 87  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0     -20.850  -1.485   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -20.080  -0.151   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -18.540  -0.151   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -17.770   1.183   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -16.230   1.183   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -15.460   2.516   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0     -13.920   2.516   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0     -13.150   3.850   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0     -13.920   5.184   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0     -11.610   3.850   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0     -10.840   5.184   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -9.300   5.184   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -8.530   6.517   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.990   6.517   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.220   5.184   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.990   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.530   3.850   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -4.680   5.184   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -3.910   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.370   3.850   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      -1.465   2.604   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      -1.465   5.096   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      -1.941   6.561   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   32  N   UNK     0       5.335   3.080   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.336   0.770   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      10.669   3.080   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      13.337   3.080   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       5.335   7.700   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   45  N   UNK     0       6.668   5.390   0.000  0.00  0.00           N+0
HETATM   46  N   UNK     0     -11.610   6.517   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   46                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   29                                                  
CONECT   23   22   24   26                                                  
CONECT   24   23   20   25                                                  
CONECT   25   24                                                            
CONECT   26   23   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28   22                                                       
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   40                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38                                                            
CONECT   40   32   41   45                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   40                                                       
CONECT   46   11                                                            
MASTER        0    0    0    0    0    0    0    0   46    0   98    0
END

COMPND    HMDB0015641
HETATM    1  C1  UNL     1      14.437  -0.369  -1.086  1.00  0.00           C  
HETATM    2  C2  UNL     1      13.234  -0.258  -0.150  1.00  0.00           C  
HETATM    3  C3  UNL     1      13.227  -1.366   0.860  1.00  0.00           C  
HETATM    4  C4  UNL     1      12.068  -1.312   1.804  1.00  0.00           C  
HETATM    5  C5  UNL     1      10.720  -1.411   1.116  1.00  0.00           C  
HETATM    6  C6  UNL     1       9.649  -1.338   2.179  1.00  0.00           C  
HETATM    7  O1  UNL     1       8.346  -1.428   1.699  1.00  0.00           O  
HETATM    8  C7  UNL     1       7.835  -0.530   0.806  1.00  0.00           C  
HETATM    9  O2  UNL     1       8.562   0.410   0.400  1.00  0.00           O  
HETATM   10  N1  UNL     1       6.504  -0.619   0.316  1.00  0.00           N  
HETATM   11  C8  UNL     1       6.035   0.343  -0.381  1.00  0.00           C  
HETATM   12  N2  UNL     1       6.827   1.475  -0.657  1.00  0.00           N  
HETATM   13  C9  UNL     1       4.677   0.272  -0.883  1.00  0.00           C  
HETATM   14  C10 UNL     1       3.897  -0.847  -0.651  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.590  -0.914  -1.092  1.00  0.00           C  
HETATM   16  C12 UNL     1       2.007   0.130  -1.782  1.00  0.00           C  
HETATM   17  N3  UNL     1       0.660   0.084  -2.208  1.00  0.00           N  
HETATM   18  C13 UNL     1      -0.210  -1.056  -2.125  1.00  0.00           C  
HETATM   19  C14 UNL     1      -1.534  -0.571  -1.687  1.00  0.00           C  
HETATM   20  N4  UNL     1      -2.381   0.233  -2.323  1.00  0.00           N  
HETATM   21  C15 UNL     1      -3.485   0.425  -1.533  1.00  0.00           C  
HETATM   22  C16 UNL     1      -4.636   1.148  -1.690  1.00  0.00           C  
HETATM   23  C17 UNL     1      -5.582   1.123  -0.648  1.00  0.00           C  
HETATM   24  C18 UNL     1      -6.772   1.949  -0.738  1.00  0.00           C  
HETATM   25  O3  UNL     1      -6.709   2.932  -1.577  1.00  0.00           O  
HETATM   26  N5  UNL     1      -7.927   1.738   0.008  1.00  0.00           N  
HETATM   27  C19 UNL     1      -8.423   0.463   0.395  1.00  0.00           C  
HETATM   28  C20 UNL     1      -9.445  -0.044  -0.686  1.00  0.00           C  
HETATM   29  C21 UNL     1      -9.878  -1.373  -0.196  1.00  0.00           C  
HETATM   30  O4  UNL     1     -10.758  -1.977  -0.858  1.00  0.00           O  
HETATM   31  O5  UNL     1      -9.372  -1.953   0.919  1.00  0.00           O  
HETATM   32  C22 UNL     1      -9.715  -3.191   1.454  1.00  0.00           C  
HETATM   33  C23 UNL     1     -11.151  -3.339   1.846  1.00  0.00           C  
HETATM   34  C24 UNL     1      -8.796   2.868   0.281  1.00  0.00           C  
HETATM   35  C25 UNL     1      -8.294   4.137   0.478  1.00  0.00           C  
HETATM   36  C26 UNL     1      -9.092   5.229   0.743  1.00  0.00           C  
HETATM   37  C27 UNL     1     -10.455   5.042   0.814  1.00  0.00           C  
HETATM   38  C28 UNL     1     -10.949   3.776   0.616  1.00  0.00           C  
HETATM   39  N6  UNL     1     -10.132   2.741   0.361  1.00  0.00           N  
HETATM   40  C29 UNL     1      -5.318   0.386   0.476  1.00  0.00           C  
HETATM   41  C30 UNL     1      -4.147  -0.345   0.623  1.00  0.00           C  
HETATM   42  C31 UNL     1      -3.229  -0.321  -0.392  1.00  0.00           C  
HETATM   43  N7  UNL     1      -2.043  -0.934  -0.474  1.00  0.00           N  
HETATM   44  C32 UNL     1      -1.416  -1.814   0.498  1.00  0.00           C  
HETATM   45  C33 UNL     1       2.798   1.238  -2.007  1.00  0.00           C  
HETATM   46  C34 UNL     1       4.092   1.320  -1.577  1.00  0.00           C  
HETATM   47  H1  UNL     1      14.143  -0.954  -1.994  1.00  0.00           H  
HETATM   48  H2  UNL     1      14.751   0.633  -1.394  1.00  0.00           H  
HETATM   49  H3  UNL     1      15.225  -0.891  -0.518  1.00  0.00           H  
HETATM   50  H4  UNL     1      13.351   0.734   0.365  1.00  0.00           H  
HETATM   51  H5  UNL     1      12.284  -0.206  -0.717  1.00  0.00           H  
HETATM   52  H6  UNL     1      13.266  -2.351   0.343  1.00  0.00           H  
HETATM   53  H7  UNL     1      14.146  -1.291   1.468  1.00  0.00           H  
HETATM   54  H8  UNL     1      12.123  -0.355   2.354  1.00  0.00           H  
HETATM   55  H9  UNL     1      12.163  -2.170   2.517  1.00  0.00           H  
HETATM   56  H10 UNL     1      10.644  -0.550   0.411  1.00  0.00           H  
HETATM   57  H11 UNL     1      10.615  -2.347   0.536  1.00  0.00           H  
HETATM   58  H12 UNL     1       9.883  -2.117   2.932  1.00  0.00           H  
HETATM   59  H13 UNL     1       9.790  -0.359   2.727  1.00  0.00           H  
HETATM   60  H14 UNL     1       7.373   1.566  -1.557  1.00  0.00           H  
HETATM   61  H15 UNL     1       6.873   2.253   0.056  1.00  0.00           H  
HETATM   62  H16 UNL     1       4.360  -1.674  -0.105  1.00  0.00           H  
HETATM   63  H17 UNL     1       2.061  -1.811  -0.871  1.00  0.00           H  
HETATM   64  H18 UNL     1       0.236   0.959  -2.636  1.00  0.00           H  
HETATM   65  H19 UNL     1      -0.334  -1.461  -3.171  1.00  0.00           H  
HETATM   66  H20 UNL     1       0.164  -1.891  -1.534  1.00  0.00           H  
HETATM   67  H21 UNL     1      -4.830   1.724  -2.568  1.00  0.00           H  
HETATM   68  H22 UNL     1      -7.650  -0.310   0.388  1.00  0.00           H  
HETATM   69  H23 UNL     1      -9.006   0.442   1.335  1.00  0.00           H  
HETATM   70  H24 UNL     1     -10.263   0.669  -0.781  1.00  0.00           H  
HETATM   71  H25 UNL     1      -8.822  -0.132  -1.598  1.00  0.00           H  
HETATM   72  H26 UNL     1      -9.492  -3.966   0.693  1.00  0.00           H  
HETATM   73  H27 UNL     1      -9.108  -3.458   2.345  1.00  0.00           H  
HETATM   74  H28 UNL     1     -11.259  -4.386   2.256  1.00  0.00           H  
HETATM   75  H29 UNL     1     -11.414  -2.688   2.729  1.00  0.00           H  
HETATM   76  H30 UNL     1     -11.877  -3.280   1.026  1.00  0.00           H  
HETATM   77  H31 UNL     1      -7.204   4.296   0.421  1.00  0.00           H  
HETATM   78  H32 UNL     1      -8.712   6.220   0.898  1.00  0.00           H  
HETATM   79  H33 UNL     1     -11.131   5.892   1.023  1.00  0.00           H  
HETATM   80  H34 UNL     1     -12.007   3.587   0.664  1.00  0.00           H  
HETATM   81  H35 UNL     1      -5.955   0.349   1.361  1.00  0.00           H  
HETATM   82  H36 UNL     1      -3.938  -0.937   1.526  1.00  0.00           H  
HETATM   83  H37 UNL     1      -2.076  -1.924   1.364  1.00  0.00           H  
HETATM   84  H38 UNL     1      -1.284  -2.798  -0.047  1.00  0.00           H  
HETATM   85  H39 UNL     1      -0.427  -1.442   0.842  1.00  0.00           H  
HETATM   86  H40 UNL     1       2.335   2.066  -2.556  1.00  0.00           H  
HETATM   87  H41 UNL     1       4.684   2.206  -1.771  1.00  0.00           H  
CONECT    1    2   47   48   49
CONECT    2    3   50   51
CONECT    3    4   52   53
CONECT    4    5   54   55
CONECT    5    6   56   57
CONECT    6    7   58   59
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   11   11
CONECT   11   12   13
CONECT   12   60   61
CONECT   13   14   14   46
CONECT   14   15   62
CONECT   15   16   16   63
CONECT   16   17   45
CONECT   17   18   64
CONECT   18   19   65   66
CONECT   19   20   20   43
CONECT   20   21
CONECT   21   22   22   42
CONECT   22   23   67
CONECT   23   24   40   40
CONECT   24   25   25   26
CONECT   26   27   34
CONECT   27   28   68   69
CONECT   28   29   70   71
CONECT   29   30   30   31
CONECT   31   32
CONECT   32   33   72   73
CONECT   33   74   75   76
CONECT   34   35   35   39
CONECT   35   36   77
CONECT   36   37   37   78
CONECT   37   38   79
CONECT   38   39   39   80
CONECT   40   41   81
CONECT   41   42   42   82
CONECT   42   43
CONECT   43   44
CONECT   44   83   84   85
CONECT   45   46   46   86
CONECT   46   87
END

HMDB0015641
     RDKit          3D
Dabigatran etexilate
 87 90  0  0  0  0  0  0  0  0999 V2000
   14.4370   -0.3695   -1.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2338   -0.2583   -0.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2267   -1.3659    0.8598 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0679   -1.3124    1.8038 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7200   -1.4111    1.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6487   -1.3377    2.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3459   -1.4279    1.6989 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8353   -0.5302    0.8063 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5622    0.4099    0.3996 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5044   -0.6193    0.3157 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0348    0.3434   -0.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8266    1.4747   -0.6572 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6767    0.2723   -0.8829 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8965   -0.8467   -0.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5901   -0.9141   -1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0074    0.1301   -1.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6602    0.0841   -2.2081 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2097   -1.0564   -2.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5344   -0.5712   -1.6869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3813    0.2334   -2.3229 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4853    0.4252   -1.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6360    1.1482   -1.6903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5819    1.1228   -0.6475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7719    1.9490   -0.7383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7091    2.9321   -1.5771 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9266    1.7383    0.0077 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4230    0.4633    0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4450   -0.0436   -0.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8781   -1.3726   -0.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7576   -1.9774   -0.8584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3719   -1.9533    0.9191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7147   -3.1911    1.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1505   -3.3385    1.8457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7956    2.8683    0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2944    4.1371    0.4780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0918    5.2286    0.7428 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4553    5.0418    0.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9485    3.7755    0.6164 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1321    2.7412    0.3610 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3178    0.3856    0.4764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1467   -0.3448    0.6231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2289   -0.3209   -0.3919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0428   -0.9338   -0.4741 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4157   -1.8135    0.4982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7977    1.2376   -2.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0923    1.3200   -1.5774 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1429   -0.9541   -1.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.7514    0.6334   -1.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.2255   -0.8907   -0.5182 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3510    0.7337    0.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2840   -0.2064   -0.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2664   -2.3508    0.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1461   -1.2913    1.4679 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1233   -0.3552    2.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1628   -2.1696    2.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6437   -0.5499    0.4108 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6149   -2.3465    0.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8828   -2.1166    2.9323 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7897   -0.3589    2.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3733    1.5660   -1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8732    2.2534    0.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3602   -1.6736   -0.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0613   -1.8112   -0.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2363    0.9585   -2.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3341   -1.4609   -3.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1636   -1.8906   -1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8299    1.7236   -2.5684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6498   -0.3098    0.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0057    0.4420    1.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2629    0.6694   -0.7810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8224   -0.1320   -1.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4920   -3.9663    0.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1079   -3.4580    2.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2587   -4.3865    2.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4144   -2.6883    2.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8769   -3.2801    1.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2035    4.2958    0.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7121    6.2199    0.8985 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1312    5.8923    1.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0068    3.5874    0.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9546    0.3486    1.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9383   -0.9373    1.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0761   -1.9245    1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2843   -2.7976   -0.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4270   -1.4416    0.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3350    2.0665   -2.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6835    2.2055   -1.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  3
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 26 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
 23 40  2  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
 43 44  1  0
 16 45  1  0
 45 46  2  0
 46 13  1  0
 43 19  1  0
 42 21  1  0
 39 34  1  0
  1 47  1  0
  1 48  1  0
  1 49  1  0
  2 50  1  0
  2 51  1  0
  3 52  1  0
  3 53  1  0
  4 54  1  0
  4 55  1  0
  5 56  1  0
  5 57  1  0
  6 58  1  0
  6 59  1  0
 12 60  1  0
 12 61  1  0
 14 62  1  0
 15 63  1  0
 17 64  1  0
 18 65  1  0
 18 66  1  0
 22 67  1  0
 27 68  1  0
 27 69  1  0
 28 70  1  0
 28 71  1  0
 32 72  1  0
 32 73  1  0
 33 74  1  0
 33 75  1  0
 33 76  1  0
 35 77  1  0
 36 78  1  0
 37 79  1  0
 38 80  1  0
 40 81  1  0
 41 82  1  0
 44 83  1  0
 44 84  1  0
 44 85  1  0
 45 86  1  0
 46 87  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Pradaxa	Kegg
Dabigatran etexilic acid	Generator
Dabigatran	HMDB
Ethyl 3-[[[4-[[[(hexyloxyl)carbonyl]amino]iminomethyl]phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino] propanoate	HMDB
Etexilate mesylate, dabigatran	HMDB
Etexilate, dabigatran	HMDB
BIBR 1048	HMDB
Mesylate, dabigatran etexilate	HMDB
N-((2-(((4-(Aminoiminomethyl)phenyl)amino)methyl)-1-methyl-1H-benzimidazol-5-yl)carbonyl)-N-2-pyridinyl-beta-alanine	HMDB
Dabigatran etexilate mesylate	HMDB

Chemical Formula

C₃₄H₄₁N₇O₅

Average Molecular Weight

627.7332

Monoisotopic Molecular Weight

627.316917457

IUPAC Name

ethyl 3-(1-{2-[({4-[amino({[(hexyloxy)carbonyl]imino})methyl]phenyl}amino)methyl]-1-methyl-1H-1,3-benzodiazol-5-yl}-N-(pyridin-2-yl)formamido)propanoate

Traditional Name

dabigatran etexilate

CAS Registry Number

211915-06-9

SMILES

CCCCCCOC(=O)N=C(N)C1=CC=C(NCC2=NC3=C(C=CC(=C3)C(=O)N(CCC(=O)OCC)C3=CC=CC=N3)N2C)C=C1

InChI Identifier

InChI=1S/C34H41N7O5/c1-4-6-7-10-21-46-34(44)39-32(35)24-12-15-26(16-13-24)37-23-30-38-27-22-25(14-17-28(27)40(30)3)33(43)41(20-18-31(42)45-5-2)29-11-8-9-19-36-29/h8-9,11-17,19,22,37H,4-7,10,18,20-21,23H2,1-3H3,(H2,35,39,44)

InChI Key

KSGXQBZTULBEEQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzimidazoles

Sub Class

Not Available

Direct Parent

Benzimidazoles

Alternative Parents

Substituents

Benzimidazole
Aniline or substituted anilines
Phenylalkylamine
Secondary aliphatic/aromatic amine
Aralkylamine
Monocyclic benzene moiety
N-substituted imidazole
Pyridine
Benzenoid
Imidolactam
Azole
Imidazole
Tertiary carboxylic acid amide
Heteroaromatic compound
Carboxylic acid ester
Carboxamide group
Carbonic acid derivative
Amino acid or derivatives
Monocarboxylic acid or derivatives
Amidine
Carboxylic acid amidine
Organic 1,3-dipolar compound
Carboxylic acid derivative
Azacycle
Secondary amine
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Organic oxygen compound
Amine
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

carboxylic ester (CHEBI:70746 )
carboxamidine (CHEBI:70746 )
beta-alanine derivative (CHEBI:70746 )
pyridines (CHEBI:70746 )
aromatic amide (CHEBI:70746 )
benzimidazoles (CHEBI:70746 )

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: HMDB0015641)
Membrane (HMDB: HMDB0015641)

Source

Exogenous

Exogenous (HMDB: HMDB0015641)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	180 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	3.8	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0047 g/L	ALOGPS
logP	5.17	ALOGPS
logP	4.59	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	17.89	ChemAxon
pKa (Strongest Basic)	3.87	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	154.03 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	176.43 m³·mol⁻¹	ChemAxon
Polarizability	71.11 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	251.444	31661259
DarkChem	[M-H]-	245.269	31661259
DeepCCS	[M+H]+	246.608	30932474
DeepCCS	[M-H]-	244.783	30932474
DeepCCS	[M-2H]-	278.026	30932474
DeepCCS	[M+Na]+	252.214	30932474
AllCCS	[M+H]+	246.0	32859911
AllCCS	[M+H-H2O]+	245.3	32859911
AllCCS	[M+NH4]+	246.7	32859911
AllCCS	[M+Na]+	246.8	32859911
AllCCS	[M-H]-	224.6	32859911
AllCCS	[M+Na-2H]-	227.8	32859911
AllCCS	[M+HCOO]-	231.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dabigatran etexilate	CCCCCCOC(=O)N=C(N)C1=CC=C(NCC2=NC3=C(C=CC(=C3)C(=O)N(CCC(=O)OCC)C3=CC=CC=N3)N2C)C=C1	5929.8	Standard polar	33892256
Dabigatran etexilate	CCCCCCOC(=O)N=C(N)C1=CC=C(NCC2=NC3=C(C=CC(=C3)C(=O)N(CCC(=O)OCC)C3=CC=CC=N3)N2C)C=C1	5027.4	Standard non polar	33892256
Dabigatran etexilate	CCCCCCOC(=O)N=C(N)C1=CC=C(NCC2=NC3=C(C=CC(=C3)C(=O)N(CCC(=O)OCC)C3=CC=CC=N3)N2C)C=C1	5413.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dabigatran etexilate,1TMS,isomer #1	CCCCCCOC(=O)N=C(N[Si](C)(C)C)C1=CC=C(NCC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)C=C1	5514.7	Semi standard non polar	33892256
Dabigatran etexilate,1TMS,isomer #1	CCCCCCOC(=O)N=C(N[Si](C)(C)C)C1=CC=C(NCC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)C=C1	4497.6	Standard non polar	33892256
Dabigatran etexilate,1TMS,isomer #1	CCCCCCOC(=O)N=C(N[Si](C)(C)C)C1=CC=C(NCC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)C=C1	7254.9	Standard polar	33892256
Dabigatran etexilate,1TMS,isomer #2	CCCCCCOC(=O)N=C(N)C1=CC=C(N(CC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)[Si](C)(C)C)C=C1	5258.7	Semi standard non polar	33892256
Dabigatran etexilate,1TMS,isomer #2	CCCCCCOC(=O)N=C(N)C1=CC=C(N(CC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)[Si](C)(C)C)C=C1	4362.4	Standard non polar	33892256
Dabigatran etexilate,1TMS,isomer #2	CCCCCCOC(=O)N=C(N)C1=CC=C(N(CC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)[Si](C)(C)C)C=C1	7466.8	Standard polar	33892256
Dabigatran etexilate,2TMS,isomer #1	CCCCCCOC(=O)N=C(C1=CC=C(NCC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)C=C1)N([Si](C)(C)C)[Si](C)(C)C	5385.6	Semi standard non polar	33892256
Dabigatran etexilate,2TMS,isomer #1	CCCCCCOC(=O)N=C(C1=CC=C(NCC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)C=C1)N([Si](C)(C)C)[Si](C)(C)C	4403.1	Standard non polar	33892256
Dabigatran etexilate,2TMS,isomer #1	CCCCCCOC(=O)N=C(C1=CC=C(NCC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)C=C1)N([Si](C)(C)C)[Si](C)(C)C	6925.3	Standard polar	33892256
Dabigatran etexilate,2TMS,isomer #2	CCCCCCOC(=O)N=C(N[Si](C)(C)C)C1=CC=C(N(CC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)[Si](C)(C)C)C=C1	5322.8	Semi standard non polar	33892256
Dabigatran etexilate,2TMS,isomer #2	CCCCCCOC(=O)N=C(N[Si](C)(C)C)C1=CC=C(N(CC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)[Si](C)(C)C)C=C1	4320.0	Standard non polar	33892256
Dabigatran etexilate,2TMS,isomer #2	CCCCCCOC(=O)N=C(N[Si](C)(C)C)C1=CC=C(N(CC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)[Si](C)(C)C)C=C1	6732.6	Standard polar	33892256
Dabigatran etexilate,3TMS,isomer #1	CCCCCCOC(=O)N=C(C1=CC=C(N(CC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)[Si](C)(C)C)C=C1)N([Si](C)(C)C)[Si](C)(C)C	5218.7	Semi standard non polar	33892256
Dabigatran etexilate,3TMS,isomer #1	CCCCCCOC(=O)N=C(C1=CC=C(N(CC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)[Si](C)(C)C)C=C1)N([Si](C)(C)C)[Si](C)(C)C	4204.1	Standard non polar	33892256
Dabigatran etexilate,3TMS,isomer #1	CCCCCCOC(=O)N=C(C1=CC=C(N(CC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)[Si](C)(C)C)C=C1)N([Si](C)(C)C)[Si](C)(C)C	6435.7	Standard polar	33892256
Dabigatran etexilate,1TBDMS,isomer #1	CCCCCCOC(=O)N=C(N[Si](C)(C)C(C)(C)C)C1=CC=C(NCC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)C=C1	5670.6	Semi standard non polar	33892256
Dabigatran etexilate,1TBDMS,isomer #1	CCCCCCOC(=O)N=C(N[Si](C)(C)C(C)(C)C)C1=CC=C(NCC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)C=C1	4617.3	Standard non polar	33892256
Dabigatran etexilate,1TBDMS,isomer #1	CCCCCCOC(=O)N=C(N[Si](C)(C)C(C)(C)C)C1=CC=C(NCC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)C=C1	7162.7	Standard polar	33892256
Dabigatran etexilate,1TBDMS,isomer #2	CCCCCCOC(=O)N=C(N)C1=CC=C(N(CC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)[Si](C)(C)C(C)(C)C)C=C1	5450.1	Semi standard non polar	33892256
Dabigatran etexilate,1TBDMS,isomer #2	CCCCCCOC(=O)N=C(N)C1=CC=C(N(CC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)[Si](C)(C)C(C)(C)C)C=C1	4444.6	Standard non polar	33892256
Dabigatran etexilate,1TBDMS,isomer #2	CCCCCCOC(=O)N=C(N)C1=CC=C(N(CC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)[Si](C)(C)C(C)(C)C)C=C1	7435.3	Standard polar	33892256
Dabigatran etexilate,2TBDMS,isomer #1	CCCCCCOC(=O)N=C(C1=CC=C(NCC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	5667.1	Semi standard non polar	33892256
Dabigatran etexilate,2TBDMS,isomer #1	CCCCCCOC(=O)N=C(C1=CC=C(NCC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4645.0	Standard non polar	33892256
Dabigatran etexilate,2TBDMS,isomer #1	CCCCCCOC(=O)N=C(C1=CC=C(NCC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	6793.9	Standard polar	33892256
Dabigatran etexilate,2TBDMS,isomer #2	CCCCCCOC(=O)N=C(N[Si](C)(C)C(C)(C)C)C1=CC=C(N(CC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)[Si](C)(C)C(C)(C)C)C=C1	5590.0	Semi standard non polar	33892256
Dabigatran etexilate,2TBDMS,isomer #2	CCCCCCOC(=O)N=C(N[Si](C)(C)C(C)(C)C)C1=CC=C(N(CC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)[Si](C)(C)C(C)(C)C)C=C1	4528.5	Standard non polar	33892256
Dabigatran etexilate,2TBDMS,isomer #2	CCCCCCOC(=O)N=C(N[Si](C)(C)C(C)(C)C)C1=CC=C(N(CC2=NC3=CC(C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)=CC=C3N2C)[Si](C)(C)C(C)(C)C)C=C1	6683.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dabigatran etexilate GC-MS (Non-derivatized) - 70eV, Positive	splash10-001v-3234390000-c2177c303cbef52afbdf	2017-09-01	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dabigatran etexilate LC-ESI-qTof , Positive-QTOF	splash10-004r-0292116000-55b368cbe92da888e681	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dabigatran etexilate , positive-QTOF	splash10-00kk-0981100000-78856b63936cf67ebce2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dabigatran etexilate , positive-QTOF	splash10-004r-0292116000-55b368cbe92da888e681	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dabigatran etexilate 10V, Positive-QTOF	splash10-0ufs-4720194000-b25f304a4eefb48ffb14	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dabigatran etexilate 20V, Positive-QTOF	splash10-0uds-9634660000-7ac6e0cd9b01e5cd8430	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dabigatran etexilate 40V, Positive-QTOF	splash10-0fba-4942200000-823214c2258288f41cbb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dabigatran etexilate 10V, Negative-QTOF	splash10-00e9-2200592000-91bb2cde7f5a1c074cff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dabigatran etexilate 20V, Negative-QTOF	splash10-008d-3500940000-5f6725f159c9fa1d9ac1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dabigatran etexilate 40V, Negative-QTOF	splash10-0007-4504930000-e756884bbf82c6cfced2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dabigatran etexilate 10V, Positive-QTOF	splash10-004i-0000019000-b01a3a5bf142faf27699	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dabigatran etexilate 20V, Positive-QTOF	splash10-004l-0001960000-f016ad334f1f10cd9561	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dabigatran etexilate 40V, Positive-QTOF	splash10-005i-3913404000-8193e59d4a4ff6967cd9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dabigatran etexilate 10V, Negative-QTOF	splash10-004i-0000259000-c2af6ee3f89a87dfae64	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dabigatran etexilate 20V, Negative-QTOF	splash10-004i-1000921000-06293e9a87d653604565	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dabigatran etexilate 40V, Negative-QTOF	splash10-0fk9-1001900000-49277b2224b211f8de10	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
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 DB06695	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB06695	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06695

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4948999

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dabigatran

METLIN ID

Not Available

PubChem Compound

213023

PDB ID

Not Available

ChEBI ID

70746

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

Di Nisio M, Middeldorp S, Buller HR: Direct thrombin inhibitors. N Engl J Med. 2005 Sep 8;353(10):1028-40. [PubMed:16148288 ]
Eriksson BI, Dahl OE, Buller HR, Hettiarachchi R, Rosencher N, Bravo ML, Ahnfelt L, Piovella F, Stangier J, Kalebo P, Reilly P: A new oral direct thrombin inhibitor, dabigatran etexilate, compared with enoxaparin for prevention of thromboembolic events following total hip or knee replacement: the BISTRO II randomized trial. J Thromb Haemost. 2005 Jan;3(1):103-11. [PubMed:15634273 ]
Stangier J, Eriksson BI, Dahl OE, Ahnfelt L, Nehmiz G, Stahle H, Rathgen K, Svard R: Pharmacokinetic profile of the oral direct thrombin inhibitor dabigatran etexilate in healthy volunteers and patients undergoing total hip replacement. J Clin Pharmacol. 2005 May;45(5):555-63. [PubMed:15831779 ]
Eriksson BI, Dahl OE, Rosencher N, Kurth AA, van Dijk CN, Frostick SP, Kalebo P, Christiansen AV, Hantel S, Hettiarachchi R, Schnee J, Buller HR: Oral dabigatran etexilate vs. subcutaneous enoxaparin for the prevention of venous thromboembolism after total knee replacement: the RE-MODEL randomized trial. J Thromb Haemost. 2007 Nov;5(11):2178-85. [PubMed:17764540 ]
Eriksson BI, Dahl OE, Rosencher N, Kurth AA, van Dijk CN, Frostick SP, Prins MH, Hettiarachchi R, Hantel S, Schnee J, Buller HR: Dabigatran etexilate versus enoxaparin for prevention of venous thromboembolism after total hip replacement: a randomised, double-blind, non-inferiority trial. Lancet. 2007 Sep 15;370(9591):949-56. [PubMed:17869635 ]
Ezekowitz MD, Reilly PA, Nehmiz G, Simmers TA, Nagarakanti R, Parcham-Azad K, Pedersen KE, Lionetti DA, Stangier J, Wallentin L: Dabigatran with or without concomitant aspirin compared with warfarin alone in patients with nonvalvular atrial fibrillation (PETRO Study). Am J Cardiol. 2007 Nov 1;100(9):1419-26. Epub 2007 Aug 17. [PubMed:17950801 ]
Ginsberg JS, Davidson BL, Comp PC, Francis CW, Friedman RJ, Huo MH, Lieberman JR, Muntz JE, Raskob GE, Clements ML, Hantel S, Schnee JM, Caprini JA: Oral thrombin inhibitor dabigatran etexilate vs North American enoxaparin regimen for prevention of venous thromboembolism after knee arthroplasty surgery. J Arthroplasty. 2009 Jan;24(1):1-9. doi: 10.1016/j.arth.2008.01.132. Epub 2008 Apr 14. [PubMed:18534438 ]
Wolowacz SE, Roskell NS, Plumb JM, Caprini JA, Eriksson BI: Efficacy and safety of dabigatran etexilate for the prevention of venous thromboembolism following total hip or knee arthroplasty. A meta-analysis. Thromb Haemost. 2009 Jan;101(1):77-85. [PubMed:19132192 ]
Connolly SJ, Ezekowitz MD, Yusuf S, Eikelboom J, Oldgren J, Parekh A, Pogue J, Reilly PA, Themeles E, Varrone J, Wang S, Alings M, Xavier D, Zhu J, Diaz R, Lewis BS, Darius H, Diener HC, Joyner CD, Wallentin L: Dabigatran versus warfarin in patients with atrial fibrillation. N Engl J Med. 2009 Sep 17;361(12):1139-51. doi: 10.1056/NEJMoa0905561. Epub 2009 Aug 30. [PubMed:19717844 ]
Bauer KA: New oral anticoagulants in development: potential for improved safety profiles. Rev Neurol Dis. 2010;7(1):1-8. [PubMed:20410856 ]
Scaglione F: New oral anticoagulants: comparative pharmacology with vitamin K antagonists. Clin Pharmacokinet. 2013 Feb;52(2):69-82. doi: 10.1007/s40262-012-0030-9. [PubMed:23292752 ]
European Medicines Agency [Link]
Abrams P and Marzella N: Dabigatran (Rendix): A Promising New Oral Direct Thrombin Inhibitor. Drug Forecast. 2007;32(5):271-5. [Link]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Galanis T, Thomson L, Palladino M, Merli GJ: New oral anticoagulants. J Thromb Thrombolysis. 2011 Apr;31(3):310-20. doi: 10.1007/s11239-011-0559-8. [PubMed:21327511 ]

Showing metabocard for Dabigatran etexilate (HMDB0015641)

MOL for HMDB0015641 (Dabigatran etexilate)

3D MOL for HMDB0015641 (Dabigatran etexilate)

3D SDF for HMDB0015641 (Dabigatran etexilate)

3D-SDF for HMDB0015641 (Dabigatran etexilate)

PDB for HMDB0015641 (Dabigatran etexilate)

3D PDB for HMDB0015641 (Dabigatran etexilate)

SMILES for HMDB0015641 (Dabigatran etexilate)

INCHI for HMDB0015641 (Dabigatran etexilate)

Structure for HMDB0015641 (Dabigatran etexilate)

3D Structure for HMDB0015641 (Dabigatran etexilate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Transporters

References