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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:44 UTC

HMDB ID

HMDB0014757

Secondary Accession Numbers

HMDB14757

Metabolite Identification

Common Name

Imatinib

Description

Imatinib is a drug used to treat certain types of cancer. It is currently marketed by Novartis as Gleevec (USA) or Glivec (Europe/Australia) as its mesylate salt, imatinib mesilate (INN). It is occasionally referred to as CGP57148B or STI571 (especially in older publications). It is used in treating chronic myelogenous leukemia (CML), gastrointestinal stromal tumors (GISTs) and a number of other malignancies. It is the first member of a new class of agents that act by inhibiting particular tyrosine kinase enzymes, instead of non-specifically inhibiting rapidly dividing cells.

Structure

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

619
  Mrv0541 02231214492D          

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M  END

HMDB0014757
     RDKit          3D
Imatinib
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M  END

619
  Mrv0541 02231214492D          

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 31 35  2  0  0  0  0
 32 33  2  0  0  0  0
 34 36  2  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014757

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCN(CC2=CC=C(C=C2)C(=O)NC2=CC(NC3=NC=CC(=N3)C3=CN=CC=C3)=C(C)C=C2)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C29H31N7O/c1-21-5-10-25(18-27(21)34-29-31-13-11-26(33-29)24-4-3-12-30-19-24)32-28(37)23-8-6-22(7-9-23)20-36-16-14-35(2)15-17-36/h3-13,18-19H,14-17,20H2,1-2H3,(H,32,37)(H,31,33,34)

> <INCHI_KEY>
KTUFNOKKBVMGRW-UHFFFAOYSA-N

> <FORMULA>
C29H31N7O

> <MOLECULAR_WEIGHT>
493.6027

> <EXACT_MASS>
493.259008649

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
55.53855401250665

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)-4-[(4-methylpiperazin-1-yl)methyl]benzamide

> <ALOGPS_LOGP>
3.47

> <JCHEM_LOGP>
4.377673055

> <ALOGPS_LOGS>
-4.53

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.451730399792329

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.454877943435385

> <JCHEM_PKA_STRONGEST_BASIC>
8.272209679883193

> <JCHEM_POLAR_SURFACE_AREA>
86.28000000000002

> <JCHEM_REFRACTIVITY>
148.92929999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
imatinib

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014757
     RDKit          3D
Imatinib
 68 72  0  0  0  0  0  0  0  0999 V2000
   -5.6613   -4.1850    1.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2496   -3.7830    0.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2312   -4.6920    1.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9293   -4.3151    0.8908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6183   -2.9979    0.5369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596   -2.6491    0.3741 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2504   -1.4086   -0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4180   -0.4078   -0.4116 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7063   -1.2407   -0.1716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2557   -0.2413   -0.9716 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6196   -0.0738   -1.0563 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5056   -0.8719   -0.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9814   -0.6785   -0.4668 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2300    0.6186   -0.9978 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7279    1.6273   -0.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7578    2.2123    0.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0257    2.4135    0.1869 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1033    1.6883    0.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0159    2.1968   -1.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5342    0.8141   -1.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9734   -1.8736    0.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5959   -2.0278    0.5097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6854   -2.1133    0.3758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0019   -2.4474    0.5398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0747   -1.5694    0.3841 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9656   -0.2071    0.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8474    0.4617   -0.2299 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7630    1.7479   -0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9424    2.4971   -0.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1159    1.8444   -0.4199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3839    2.5577   -0.5089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5583    1.8620   -0.2452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7408    2.5394   -0.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7594    3.8908   -0.6705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6247    4.5485   -0.9217 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4299    3.8895   -0.8433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1122    0.5476   -0.0874 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2865   -3.9737    0.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6978   -5.2773    1.2321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1330   -3.7182    1.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4831   -5.7238    1.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1392   -5.0661    1.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4329   -3.4320    0.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5568    0.3841   -1.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0286    0.7207   -1.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3708   -1.5014   -1.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4283   -0.8553    0.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3067    2.4876   -0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8961    1.2790    0.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8141    1.6367    1.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3702    3.2319    1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9807    2.3800    0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7970    1.2933    1.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4461    0.8209    0.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0692    2.2605   -1.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3739    2.9099   -1.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4471    0.7425   -2.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2607    0.0226   -1.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6736   -2.4917    0.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2319   -2.8168    1.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4052   -1.1167    0.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0666   -1.9591    0.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8468    2.2720   -0.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8760    3.5476   -0.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5050    0.8398    0.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6822    2.0483   -0.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7174    4.3820   -0.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5564    4.4983   -1.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 12 21  1  0
 21 22  2  0
  5 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 30 37  2  0
 24  2  1  0
 37 26  1  0
 22  9  1  0
 36 31  1  0
 20 14  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  3 41  1  0
  4 42  1  0
  6 43  1  0
 10 44  1  0
 11 45  1  0
 13 46  1  0
 13 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 18 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  0
 22 60  1  0
 23 61  1  0
 25 62  1  0
 28 63  1  0
 29 64  1  0
 32 65  1  0
 33 66  1  0
 34 67  1  0
 36 68  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 619                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      11.082  -0.770   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       4.414  -4.620   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       4.414  -7.700   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       9.748   1.540   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      12.416   6.160   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       9.748   6.160   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      11.082   8.470   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       5.748   3.850   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       3.080  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.080  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414  -9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.748  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.748  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.415  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.081   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.748   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.082   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.416   4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.082   3.850   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.750   3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.416   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.750   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.083   4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.082   6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.415   6.930   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.081   6.160   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.415   8.470   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.748   9.240   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.748   6.930   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.081   4.620   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.414   6.160   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.414   4.620   0.000  0.00  0.00           C+0
CONECT    1   21                                                            
CONECT    2    9   10   13                                                  
CONECT    3   11   12   14                                                  
CONECT    4   21   22                                                       
CONECT    5   23   29                                                       
CONECT    6   29   30                                                       
CONECT    7   29   33                                                       
CONECT    8   35   37                                                       
CONECT    9    2   11                                                       
CONECT   10    2   12                                                       
CONECT   11    3    9                                                       
CONECT   12    3   10                                                       
CONECT   13    2   15                                                       
CONECT   14    3                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15   18                                                       
CONECT   17   15   19                                                       
CONECT   18   16   20                                                       
CONECT   19   17   20                                                       
CONECT   20   18   19   21                                                  
CONECT   21    1    4   20                                                  
CONECT   22    4   24   26                                                  
CONECT   23    5   24   25                                                  
CONECT   24   22   23                                                       
CONECT   25   23   27   28                                                  
CONECT   26   22   27                                                       
CONECT   27   25   26                                                       
CONECT   28   25                                                            
CONECT   29    5    6    7                                                  
CONECT   30    6   31   32                                                  
CONECT   31   30   34   35                                                  
CONECT   32   30   33                                                       
CONECT   33    7   32                                                       
CONECT   34   31   36                                                       
CONECT   35    8   31                                                       
CONECT   36   34   37                                                       
CONECT   37    8   36                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

COMPND    HMDB0014757
HETATM    1  C1  UNL     1      -5.661  -4.185   1.082  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.250  -3.783   0.895  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.231  -4.692   1.065  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.929  -4.315   0.891  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.618  -2.998   0.537  1.00  0.00           C  
HETATM    6  N1  UNL     1      -0.260  -2.649   0.374  1.00  0.00           N  
HETATM    7  C6  UNL     1       0.250  -1.409  -0.076  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.418  -0.408  -0.412  1.00  0.00           O  
HETATM    9  C7  UNL     1       1.706  -1.241  -0.172  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.256  -0.241  -0.972  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.620  -0.074  -1.056  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.506  -0.872  -0.366  1.00  0.00           C  
HETATM   13  C11 UNL     1       5.981  -0.678  -0.467  1.00  0.00           C  
HETATM   14  N2  UNL     1       6.230   0.619  -0.998  1.00  0.00           N  
HETATM   15  C12 UNL     1       5.728   1.627  -0.129  1.00  0.00           C  
HETATM   16  C13 UNL     1       6.758   2.212   0.817  1.00  0.00           C  
HETATM   17  N3  UNL     1       8.026   2.414   0.187  1.00  0.00           N  
HETATM   18  C14 UNL     1       9.103   1.688   0.786  1.00  0.00           C  
HETATM   19  C15 UNL     1       8.016   2.197  -1.227  1.00  0.00           C  
HETATM   20  C16 UNL     1       7.534   0.814  -1.526  1.00  0.00           C  
HETATM   21  C17 UNL     1       3.973  -1.874   0.436  1.00  0.00           C  
HETATM   22  C18 UNL     1       2.596  -2.028   0.510  1.00  0.00           C  
HETATM   23  C19 UNL     1      -2.685  -2.113   0.376  1.00  0.00           C  
HETATM   24  C20 UNL     1      -4.002  -2.447   0.540  1.00  0.00           C  
HETATM   25  N4  UNL     1      -5.075  -1.569   0.384  1.00  0.00           N  
HETATM   26  C21 UNL     1      -4.966  -0.207   0.023  1.00  0.00           C  
HETATM   27  N5  UNL     1      -3.847   0.462  -0.230  1.00  0.00           N  
HETATM   28  C22 UNL     1      -3.763   1.748  -0.566  1.00  0.00           C  
HETATM   29  C23 UNL     1      -4.942   2.497  -0.673  1.00  0.00           C  
HETATM   30  C24 UNL     1      -6.116   1.844  -0.420  1.00  0.00           C  
HETATM   31  C25 UNL     1      -7.384   2.558  -0.509  1.00  0.00           C  
HETATM   32  C26 UNL     1      -8.558   1.862  -0.245  1.00  0.00           C  
HETATM   33  C27 UNL     1      -9.741   2.539  -0.329  1.00  0.00           C  
HETATM   34  C28 UNL     1      -9.759   3.891  -0.670  1.00  0.00           C  
HETATM   35  N6  UNL     1      -8.625   4.548  -0.922  1.00  0.00           N  
HETATM   36  C29 UNL     1      -7.430   3.890  -0.843  1.00  0.00           C  
HETATM   37  N7  UNL     1      -6.112   0.548  -0.087  1.00  0.00           N  
HETATM   38  H1  UNL     1      -6.286  -3.974   0.190  1.00  0.00           H  
HETATM   39  H2  UNL     1      -5.698  -5.277   1.232  1.00  0.00           H  
HETATM   40  H3  UNL     1      -6.133  -3.718   1.982  1.00  0.00           H  
HETATM   41  H4  UNL     1      -3.483  -5.724   1.343  1.00  0.00           H  
HETATM   42  H5  UNL     1      -1.139  -5.066   1.034  1.00  0.00           H  
HETATM   43  H6  UNL     1       0.433  -3.432   0.624  1.00  0.00           H  
HETATM   44  H7  UNL     1       1.557   0.384  -1.513  1.00  0.00           H  
HETATM   45  H8  UNL     1       4.029   0.721  -1.696  1.00  0.00           H  
HETATM   46  H9  UNL     1       6.371  -1.501  -1.127  1.00  0.00           H  
HETATM   47  H10 UNL     1       6.428  -0.855   0.532  1.00  0.00           H  
HETATM   48  H11 UNL     1       5.307   2.488  -0.728  1.00  0.00           H  
HETATM   49  H12 UNL     1       4.896   1.279   0.515  1.00  0.00           H  
HETATM   50  H13 UNL     1       6.814   1.637   1.774  1.00  0.00           H  
HETATM   51  H14 UNL     1       6.370   3.232   1.106  1.00  0.00           H  
HETATM   52  H15 UNL     1       9.981   2.380   0.852  1.00  0.00           H  
HETATM   53  H16 UNL     1       8.797   1.293   1.779  1.00  0.00           H  
HETATM   54  H17 UNL     1       9.446   0.821   0.202  1.00  0.00           H  
HETATM   55  H18 UNL     1       9.069   2.260  -1.592  1.00  0.00           H  
HETATM   56  H19 UNL     1       7.374   2.910  -1.777  1.00  0.00           H  
HETATM   57  H20 UNL     1       7.447   0.743  -2.651  1.00  0.00           H  
HETATM   58  H21 UNL     1       8.261   0.023  -1.252  1.00  0.00           H  
HETATM   59  H22 UNL     1       4.674  -2.492   0.971  1.00  0.00           H  
HETATM   60  H23 UNL     1       2.232  -2.817   1.151  1.00  0.00           H  
HETATM   61  H24 UNL     1      -2.405  -1.117   0.109  1.00  0.00           H  
HETATM   62  H25 UNL     1      -6.067  -1.959   0.553  1.00  0.00           H  
HETATM   63  H26 UNL     1      -2.847   2.272  -0.768  1.00  0.00           H  
HETATM   64  H27 UNL     1      -4.876   3.548  -0.947  1.00  0.00           H  
HETATM   65  H28 UNL     1      -8.505   0.840   0.010  1.00  0.00           H  
HETATM   66  H29 UNL     1     -10.682   2.048  -0.134  1.00  0.00           H  
HETATM   67  H30 UNL     1     -10.717   4.382  -0.724  1.00  0.00           H  
HETATM   68  H31 UNL     1      -6.556   4.498  -1.063  1.00  0.00           H  
CONECT    1    2   38   39   40
CONECT    2    3    3   24
CONECT    3    4   41
CONECT    4    5    5   42
CONECT    5    6   23
CONECT    6    7   43
CONECT    7    8    8    9
CONECT    9   10   10   22
CONECT   10   11   44
CONECT   11   12   12   45
CONECT   12   13   21
CONECT   13   14   46   47
CONECT   14   15   20
CONECT   15   16   48   49
CONECT   16   17   50   51
CONECT   17   18   19
CONECT   18   52   53   54
CONECT   19   20   55   56
CONECT   20   57   58
CONECT   21   22   22   59
CONECT   22   60
CONECT   23   24   24   61
CONECT   24   25
CONECT   25   26   62
CONECT   26   27   27   37
CONECT   27   28
CONECT   28   29   29   63
CONECT   29   30   64
CONECT   30   31   37   37
CONECT   31   32   32   36
CONECT   32   33   65
CONECT   33   34   34   66
CONECT   34   35   67
CONECT   35   36   36
CONECT   36   68
END

HMDB0014757
     RDKit          3D
Imatinib
 68 72  0  0  0  0  0  0  0  0999 V2000
   -5.6613   -4.1850    1.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2496   -3.7830    0.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2312   -4.6920    1.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9293   -4.3151    0.8908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6183   -2.9979    0.5369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596   -2.6491    0.3741 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2504   -1.4086   -0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4180   -0.4078   -0.4116 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7063   -1.2407   -0.1716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2557   -0.2413   -0.9716 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6196   -0.0738   -1.0563 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5056   -0.8719   -0.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9814   -0.6785   -0.4668 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2300    0.6186   -0.9978 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7279    1.6273   -0.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7578    2.2123    0.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0257    2.4135    0.1869 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1033    1.6883    0.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0159    2.1968   -1.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5342    0.8141   -1.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9734   -1.8736    0.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5959   -2.0278    0.5097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6854   -2.1133    0.3758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0019   -2.4474    0.5398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0747   -1.5694    0.3841 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9656   -0.2071    0.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8474    0.4617   -0.2299 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7630    1.7479   -0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9424    2.4971   -0.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1159    1.8444   -0.4199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3839    2.5577   -0.5089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5583    1.8620   -0.2452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7408    2.5394   -0.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7594    3.8908   -0.6705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6247    4.5485   -0.9217 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4299    3.8895   -0.8433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1122    0.5476   -0.0874 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2865   -3.9737    0.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6978   -5.2773    1.2321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1330   -3.7182    1.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4831   -5.7238    1.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1392   -5.0661    1.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4329   -3.4320    0.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5568    0.3841   -1.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0286    0.7207   -1.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3708   -1.5014   -1.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4283   -0.8553    0.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3067    2.4876   -0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8961    1.2790    0.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8141    1.6367    1.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3702    3.2319    1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9807    2.3800    0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7970    1.2933    1.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4461    0.8209    0.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0692    2.2605   -1.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3739    2.9099   -1.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4471    0.7425   -2.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2607    0.0226   -1.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6736   -2.4917    0.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2319   -2.8168    1.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4052   -1.1167    0.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0666   -1.9591    0.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8468    2.2720   -0.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8760    3.5476   -0.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5050    0.8398    0.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6822    2.0483   -0.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7174    4.3820   -0.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5564    4.4983   -1.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 12 21  1  0
 21 22  2  0
  5 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 30 37  2  0
 24  2  1  0
 37 26  1  0
 22  9  1  0
 36 31  1  0
 20 14  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  3 41  1  0
  4 42  1  0
  6 43  1  0
 10 44  1  0
 11 45  1  0
 13 46  1  0
 13 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 18 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  0
 22 60  1  0
 23 61  1  0
 25 62  1  0
 28 63  1  0
 29 64  1  0
 32 65  1  0
 33 66  1  0
 34 67  1  0
 36 68  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(4-METHYL-piperazin-1-ylmethyl)-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-benzamide	ChEBI
alpha-(4-Methyl-1-piperazinyl)-3'-((4-(3-pyridyl)-2-pyrimidinyl)amino)-p-toluidide	ChEBI
STI 571	ChEBI
Glamox	Kegg
a-(4-Methyl-1-piperazinyl)-3'-((4-(3-pyridyl)-2-pyrimidinyl)amino)-p-toluidide	Generator
Α-(4-methyl-1-piperazinyl)-3'-((4-(3-pyridyl)-2-pyrimidinyl)amino)-p-toluidide	Generator
Imatinib methansulfonate	HMDB
STI-571	HMDB
Glivec	HMDB
Methanesulfonate, imatinib	HMDB
Imatinib methanesulfonate	HMDB
Imatinib mesylate	HMDB
Gleevec	HMDB
Mesylate, imatinib	HMDB
alpha-(4-Methyl-1-piperazinyl)-3'-((4-(3-pyridyl)-2-pyrimidinyl)amino)-p-tolu-p-toluidide	HMDB

Chemical Formula

C₂₉H₃₁N₇O

Average Molecular Weight

493.6027

Monoisotopic Molecular Weight

493.259008649

IUPAC Name

N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)-4-[(4-methylpiperazin-1-yl)methyl]benzamide

Traditional Name

imatinib

CAS Registry Number

152459-95-5

SMILES

CN1CCN(CC2=CC=C(C=C2)C(=O)NC2=CC(NC3=NC=CC(=N3)C3=CN=CC=C3)=C(C)C=C2)CC1

InChI Identifier

InChI=1S/C29H31N7O/c1-21-5-10-25(18-27(21)34-29-31-13-11-26(33-29)24-4-3-12-30-19-24)32-28(37)23-8-6-22(7-9-23)20-36-16-14-35(2)15-17-36/h3-13,18-19H,14-17,20H2,1-2H3,(H,32,37)(H,31,33,34)

InChI Key

KTUFNOKKBVMGRW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxazolidinediones. Oxazolidinediones are compounds containing an oxazolidine ring which bears two ketones.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolidines

Sub Class

Oxazolidines

Direct Parent

Oxazolidinediones

Alternative Parents

Substituents

Oxazolidinedione
Dicarboximide
Carbamic acid ester
Carbonic acid derivative
Oxacycle
Azacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

oxazolidinone (CHEBI:7921 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014757)
Membrane (HMDB: HMDB0014757)

Source

Exogenous

Exogenous (HMDB: HMDB0014757)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Imatinib Inhibition of BCR-ABL (PathBank: SMP0031694)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	226 °C (mesylate salt)	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.015 g/L	Not Available
LogP	3	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	214.6	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.015 g/L	ALOGPS
logP	3.47	ALOGPS
logP	4.38	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	12.45	ChemAxon
pKa (Strongest Basic)	8.27	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	86.28 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	148.93 m³·mol⁻¹	ChemAxon
Polarizability	55.54 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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]+	223.415	31661259
DarkChem	[M-H]-	219.191	31661259
DeepCCS	[M+H]+	218.298	30932474
DeepCCS	[M-H]-	215.902	30932474
DeepCCS	[M-2H]-	248.786	30932474
DeepCCS	[M+Na]+	224.211	30932474
AllCCS	[M+H]+	224.1	32859911
AllCCS	[M+H-H2O]+	222.3	32859911
AllCCS	[M+NH4]+	225.8	32859911
AllCCS	[M+Na]+	226.3	32859911
AllCCS	[M-H]-	212.9	32859911
AllCCS	[M+Na-2H]-	213.8	32859911
AllCCS	[M+HCOO]-	215.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.62 minutes	32390414
Predicted by Siyang on May 30, 2022	9.3086 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.79 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	63.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	766.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	121.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	143.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	126.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	61.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	293.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	400.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	193.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	715.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	57.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	764.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	208.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	273.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	223.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	347.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	242.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Imatinib	CN1CCN(CC2=CC=C(C=C2)C(=O)NC2=CC(NC3=NC=CC(=N3)C3=CN=CC=C3)=C(C)C=C2)CC1	5474.1	Standard polar	33892256
Imatinib	CN1CCN(CC2=CC=C(C=C2)C(=O)NC2=CC(NC3=NC=CC(=N3)C3=CN=CC=C3)=C(C)C=C2)CC1	4494.6	Standard non polar	33892256
Imatinib	CN1CCN(CC2=CC=C(C=C2)C(=O)NC2=CC(NC3=NC=CC(=N3)C3=CN=CC=C3)=C(C)C=C2)CC1	5034.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Imatinib,1TMS,isomer #1	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)[Si](C)(C)C)C=C1NC1=NC=CC(C2=CC=CN=C2)=N1	4439.7	Semi standard non polar	33892256
Imatinib,1TMS,isomer #1	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)[Si](C)(C)C)C=C1NC1=NC=CC(C2=CC=CN=C2)=N1	2643.1	Standard non polar	33892256
Imatinib,1TMS,isomer #1	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)[Si](C)(C)C)C=C1NC1=NC=CC(C2=CC=CN=C2)=N1	5873.1	Standard polar	33892256
Imatinib,1TMS,isomer #2	CC1=CC=C(NC(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C	4540.1	Semi standard non polar	33892256
Imatinib,1TMS,isomer #2	CC1=CC=C(NC(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C	2926.8	Standard non polar	33892256
Imatinib,1TMS,isomer #2	CC1=CC=C(NC(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C	5795.6	Standard polar	33892256
Imatinib,2TMS,isomer #1	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)[Si](C)(C)C)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C	4272.2	Semi standard non polar	33892256
Imatinib,2TMS,isomer #1	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)[Si](C)(C)C)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C	2829.6	Standard non polar	33892256
Imatinib,2TMS,isomer #1	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)[Si](C)(C)C)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C	5475.5	Standard polar	33892256
Imatinib,1TBDMS,isomer #1	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)[Si](C)(C)C(C)(C)C)C=C1NC1=NC=CC(C2=CC=CN=C2)=N1	4604.1	Semi standard non polar	33892256
Imatinib,1TBDMS,isomer #1	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)[Si](C)(C)C(C)(C)C)C=C1NC1=NC=CC(C2=CC=CN=C2)=N1	2843.4	Standard non polar	33892256
Imatinib,1TBDMS,isomer #1	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)[Si](C)(C)C(C)(C)C)C=C1NC1=NC=CC(C2=CC=CN=C2)=N1	5915.7	Standard polar	33892256
Imatinib,1TBDMS,isomer #2	CC1=CC=C(NC(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C(C)(C)C	4693.6	Semi standard non polar	33892256
Imatinib,1TBDMS,isomer #2	CC1=CC=C(NC(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C(C)(C)C	3126.6	Standard non polar	33892256
Imatinib,1TBDMS,isomer #2	CC1=CC=C(NC(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C(C)(C)C	5815.5	Standard polar	33892256
Imatinib,2TBDMS,isomer #1	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)[Si](C)(C)C(C)(C)C)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C(C)(C)C	4603.2	Semi standard non polar	33892256
Imatinib,2TBDMS,isomer #1	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)[Si](C)(C)C(C)(C)C)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C(C)(C)C	3324.7	Standard non polar	33892256
Imatinib,2TBDMS,isomer #1	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN(C)CC3)C=C2)[Si](C)(C)C(C)(C)C)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C(C)(C)C	5509.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Imatinib GC-MS (Non-derivatized) - 70eV, Positive	splash10-01bd-9863300000-bf69c843c9ad9179bcdb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Imatinib GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imatinib LC-ESI-qTof , Positive-QTOF	splash10-0006-0036900000-e06abe669a9b1b57e2c3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imatinib LC-ESI-QFT , negative-QTOF	splash10-0006-0000900000-3974d719909aa7a75039	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imatinib LC-ESI-QFT , negative-QTOF	splash10-0006-0000900000-dd386ae17930da36c11f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imatinib LC-ESI-QFT , negative-QTOF	splash10-0f6x-0159500000-576f293e026deaa1ec7f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imatinib LC-ESI-QFT , negative-QTOF	splash10-0ik9-0495000000-06102c4afd3c2e88cf87	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imatinib LC-ESI-QFT , negative-QTOF	splash10-03ka-0971000000-b487f693e17cba198e37	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imatinib LC-ESI-QFT , negative-QTOF	splash10-05fs-0930000000-9319811c561fd5cc8f2f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imatinib LC-ESI-QFT , negative-QTOF	splash10-0159-4910000000-25480eb9451aee843c26	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imatinib LC-ESI-QFT , negative-QTOF	splash10-014i-9000000000-0638bee21655c0e0ca00	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imatinib LC-ESI-QFT , negative-QTOF	splash10-014i-9000000000-76f9b62b017fe8241e67	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imatinib LC-ESI-QFT , positive-QTOF	splash10-0006-0000900000-9825e12c65f9bf36d72f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imatinib LC-ESI-QFT , positive-QTOF	splash10-0006-1029200000-acd76280414e767f0280	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imatinib LC-ESI-QFT , positive-QTOF	splash10-0006-2269000000-f55e5c707c9de5ba2d0f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imatinib LC-ESI-QFT , positive-QTOF	splash10-00ba-3494000000-19e7d8361f050ec8b637	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imatinib LC-ESI-QFT , positive-QTOF	splash10-00ba-3693000000-c1e011113081e3341bba	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imatinib LC-ESI-QFT , positive-QTOF	splash10-0596-5981000000-a0f689cd067d45644bcd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imatinib LC-ESI-QFT , positive-QTOF	splash10-0f9f-5930000000-71f05e812cf29e11cc69	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imatinib LC-ESI-QFT , positive-QTOF	splash10-00ku-5910000000-3f91ea6a6f7402767a78	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Imatinib LC-ESI-QFT , positive-QTOF	splash10-029i-7900000000-507c771376ea4b799b6d	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imatinib 10V, Positive-QTOF	splash10-0006-0144900000-2c1268fe741d4e07f7a4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imatinib 20V, Positive-QTOF	splash10-00kf-0698300000-b23d90ff38472b542f79	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imatinib 40V, Positive-QTOF	splash10-02tc-3911000000-88d44a81ccb6cf024cbc	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imatinib 10V, Negative-QTOF	splash10-0006-1110900000-e7ed25c6dc02f44eff1e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imatinib 20V, Negative-QTOF	splash10-002g-7534900000-56f8e35b9d7416fcc95f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imatinib 40V, Negative-QTOF	splash10-0006-9610100000-772d808632d87b2ad3e5	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Imatinib Inhibition of BCR-ABL		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00619	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00619	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00619

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5101

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Imatinib

METLIN ID

Not Available

PubChem Compound

5291

PDB ID

STI

ChEBI ID

45783

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

Droogendijk HJ, Kluin-Nelemans HJ, van Doormaal JJ, Oranje AP, van de Loosdrecht AA, van Daele PL: Imatinib mesylate in the treatment of systemic mastocytosis: a phase II trial. Cancer. 2006 Jul 15;107(2):345-51. [PubMed:16779792 ]
Vigneri P, Wang JY: Induction of apoptosis in chronic myelogenous leukemia cells through nuclear entrapment of BCR-ABL tyrosine kinase. Nat Med. 2001 Feb;7(2):228-34. [PubMed:11175855 ]
Deininger MW, Druker BJ: Specific targeted therapy of chronic myelogenous leukemia with imatinib. Pharmacol Rev. 2003 Sep;55(3):401-23. Epub 2003 Jul 17. [PubMed:12869662 ]
Lassila M, Allen TJ, Cao Z, Thallas V, Jandeleit-Dahm KA, Candido R, Cooper ME: Imatinib attenuates diabetes-associated atherosclerosis. Arterioscler Thromb Vasc Biol. 2004 May;24(5):935-42. Epub 2004 Feb 26. [PubMed:14988091 ]
Reeves PM, Bommarius B, Lebeis S, McNulty S, Christensen J, Swimm A, Chahroudi A, Chavan R, Feinberg MB, Veach D, Bornmann W, Sherman M, Kalman D: Disabling poxvirus pathogenesis by inhibition of Abl-family tyrosine kinases. Nat Med. 2005 Jul;11(7):731-9. Epub 2005 Jun 26. [PubMed:15980865 ]

Showing metabocard for Imatinib (HMDB0014757)

MOL for HMDB0014757 (Imatinib)

3D MOL for HMDB0014757 (Imatinib)

3D SDF for HMDB0014757 (Imatinib)

3D-SDF for HMDB0014757 (Imatinib)

PDB for HMDB0014757 (Imatinib)

3D PDB for HMDB0014757 (Imatinib)

SMILES for HMDB0014757 (Imatinib)

INCHI for HMDB0014757 (Imatinib)

Structure for HMDB0014757 (Imatinib)

3D Structure for HMDB0014757 (Imatinib)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra