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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (15)transporters (4) Show 19 proteins XML

enzymes (15)transporters (4) Show 19 proteins

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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:15 UTC

Update Date

2020-07-06 16:01:13 UTC

HMDB ID

HMDB0013862

Secondary Accession Numbers

HMDB13862

Metabolite Identification

Common Name

N-desmethylimatinib

Description

N-Desmethylimatinib, also called CGP74588, is a metabolite of Imatinib, a tyrosine kinase inhibitor, which is used to treat chronic myelogenous leukemia (CML) with BCR-ABL activity, gastrointestinal stromal tumors and acute lymphocytic leukemia (ALL). N-desmethylimatinib is pharmacologically active and shows a similar potency and selectivity profile as the parent drug. In particular, it shows potent inhibition of BCR-ABL in the nanomolar range (PMID: 21225261 ). The N-demethylation of Imatinib to N-desmethylimatinib is done via the liver cytochrome P450 enzymes CYP2C8, CYP3A4, CYP3A5 and CYP3A7 (PMID: 20977456 ). N-desmethylimatinib is only found in individuals who have consumed or received the drug Imatinib.

Structure

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

619
  Mrv0541 02271201052D          

 36 40  0  0  0  0            999 V2000
    5.9370   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.4751    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.1251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    3.3001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.3001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    4.5376    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    4.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  2  0  0  0  0
  2  9  1  0  0  0  0
  2 10  1  0  0  0  0
  2 13  1  0  0  0  0
  3 11  1  0  0  0  0
  3 12  1  0  0  0  0
  4 20  1  0  0  0  0
  4 21  1  0  0  0  0
  5 22  1  0  0  0  0
  5 28  1  0  0  0  0
  6 28  1  0  0  0  0
  6 29  2  0  0  0  0
  7 28  2  0  0  0  0
  7 32  1  0  0  0  0
  8 34  1  0  0  0  0
  8 36  2  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  2  0  0  0  0
 17 19  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 23  2  0  0  0  0
 21 25  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 25 26  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 30 33  1  0  0  0  0
 30 34  2  0  0  0  0
 31 32  2  0  0  0  0
 33 35  2  0  0  0  0
 35 36  1  0  0  0  0
M  END

HMDB0060621
     RDKit          3D
n-Demethylated piperazine
 65 69  0  0  0  0  0  0  0  0999 V2000
    4.4441   -0.8922    4.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2226   -0.6590    3.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0097   -0.6813    4.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8455   -0.4634    3.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8706   -0.2265    2.4370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2634   -0.0002    1.6421 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6026    0.0582    2.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9215   -0.1021    3.2300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6818    0.3039    1.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9861    0.5276    1.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0375    0.7588    0.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8379    0.7794   -0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9140    1.0184   -1.6517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2388    0.9403   -1.0637 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2567    1.2079   -2.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2297    0.2228   -3.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0815   -1.1434   -2.7337 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4545   -1.1787   -1.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4847   -0.3686   -0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5591    0.5616   -1.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5026    0.3283   -0.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1461   -0.2147    1.8398 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3082   -0.4199    2.5128 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5620   -0.4056    1.9049 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8741   -0.1851    0.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9822    0.0540   -0.3989 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2462    0.2668   -1.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5981    0.2283   -2.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5714   -0.0149   -1.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0114   -0.0613   -1.4717 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4670    0.1319   -2.7353 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8211    0.0729   -2.9855 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6769   -0.1812   -1.9438 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2374   -0.3735   -0.6919 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9212   -0.3157   -0.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1827   -0.2135    0.1513 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9156   -1.8733    4.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2156   -0.1109    4.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2168   -0.8550    5.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9663   -0.8673    5.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0590   -0.4958    4.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0815    0.1502    0.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1259    0.5081    2.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0313    0.9292    1.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7898    0.4182   -2.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7976    2.0938   -1.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2434    1.1853   -1.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0833    2.2283   -2.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3776    0.4276   -3.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1532    0.3420   -3.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1431   -1.5298   -2.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4910   -0.8082   -1.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4541   -2.2216   -0.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0380   -0.2040    0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5840   -0.9441   -0.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3812    0.5741   -2.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5393    0.1656   -0.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1461   -0.0277    0.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4027   -0.5874    2.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4782    0.4596   -2.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8329    0.3952   -3.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7566    0.3350   -3.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2163    0.2214   -3.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7674   -0.2394   -2.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5124   -0.4666    0.5582 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
 18 19  1  0
 12 20  1  0
 20 21  2  0
  5 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 29 36  2  0
 23  2  1  0
 36 25  1  0
 21  9  1  0
 35 30  1  0
 19 14  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  3 40  1  0
  4 41  1  0
  6 42  1  0
 10 43  1  0
 11 44  1  0
 13 45  1  0
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 24 59  1  0
 27 60  1  0
 28 61  1  0
 31 62  1  0
 32 63  1  0
 33 64  1  0
 35 65  1  0
M  END

619
  Mrv0541 02271201052D          

 36 40  0  0  0  0            999 V2000
    5.9370   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.4751    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.1251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    3.3001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.3001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    4.5376    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    4.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  2  0  0  0  0
  2  9  1  0  0  0  0
  2 10  1  0  0  0  0
  2 13  1  0  0  0  0
  3 11  1  0  0  0  0
  3 12  1  0  0  0  0
  4 20  1  0  0  0  0
  4 21  1  0  0  0  0
  5 22  1  0  0  0  0
  5 28  1  0  0  0  0
  6 28  1  0  0  0  0
  6 29  2  0  0  0  0
  7 28  2  0  0  0  0
  7 32  1  0  0  0  0
  8 34  1  0  0  0  0
  8 36  2  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
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 18 19  1  0  0  0  0
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 21 23  2  0  0  0  0
 21 25  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 25 26  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 30 33  1  0  0  0  0
 30 34  2  0  0  0  0
 31 32  2  0  0  0  0
 33 35  2  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013862

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(NC2=NC=CC(=N2)C2=CN=CC=C2)C=C(NC(=O)C2=CC=C(CN3CCNCC3)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H29N7O/c1-20-4-9-24(17-26(20)34-28-31-12-10-25(33-28)23-3-2-11-30-18-23)32-27(36)22-7-5-21(6-8-22)19-35-15-13-29-14-16-35/h2-12,17-18,29H,13-16,19H2,1H3,(H,32,36)(H,31,33,34)

> <INCHI_KEY>
BQQYXPHRXIZMDM-UHFFFAOYSA-N

> <FORMULA>
C28H29N7O

> <MOLECULAR_WEIGHT>
479.5762

> <EXACT_MASS>
479.243358585

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
53.39200298871422

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.16

> <JCHEM_LOGP>
3.994625117666667

> <ALOGPS_LOGS>
-4.86

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.451767051933167

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.45508626889983

> <JCHEM_PKA_STRONGEST_BASIC>
9.25323786228519

> <JCHEM_POLAR_SURFACE_AREA>
95.07000000000001

> <JCHEM_REFRACTIVITY>
143.63459999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.65e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060621
     RDKit          3D
n-Demethylated piperazine
 65 69  0  0  0  0  0  0  0  0999 V2000
    4.4441   -0.8922    4.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2226   -0.6590    3.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0097   -0.6813    4.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8455   -0.4634    3.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8706   -0.2265    2.4370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2634   -0.0002    1.6421 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6026    0.0582    2.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9215   -0.1021    3.2300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6818    0.3039    1.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9861    0.5276    1.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0375    0.7588    0.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8379    0.7794   -0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9140    1.0184   -1.6517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2388    0.9403   -1.0637 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2567    1.2079   -2.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2297    0.2228   -3.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0815   -1.1434   -2.7337 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4545   -1.1787   -1.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4847   -0.3686   -0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5591    0.5616   -1.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5026    0.3283   -0.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1461   -0.2147    1.8398 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3082   -0.4199    2.5128 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5620   -0.4056    1.9049 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8741   -0.1851    0.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9822    0.0540   -0.3989 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2462    0.2668   -1.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5981    0.2283   -2.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5714   -0.0149   -1.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0114   -0.0613   -1.4717 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4670    0.1319   -2.7353 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8211    0.0729   -2.9855 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6769   -0.1812   -1.9438 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2374   -0.3735   -0.6919 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9212   -0.3157   -0.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1827   -0.2135    0.1513 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9156   -1.8733    4.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2156   -0.1109    4.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2168   -0.8550    5.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9663   -0.8673    5.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0590   -0.4958    4.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0815    0.1502    0.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1259    0.5081    2.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0313    0.9292    1.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7898    0.4182   -2.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7976    2.0938   -1.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2434    1.1853   -1.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0833    2.2283   -2.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3776    0.4276   -3.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1532    0.3420   -3.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1431   -1.5298   -2.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4910   -0.8082   -1.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4541   -2.2216   -0.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0380   -0.2040    0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5840   -0.9441   -0.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3812    0.5741   -2.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5393    0.1656   -0.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1461   -0.0277    0.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4027   -0.5874    2.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4782    0.4596   -2.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8329    0.3952   -3.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7566    0.3350   -3.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2163    0.2214   -3.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7674   -0.2394   -2.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5124   -0.4666    0.5582 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
 18 19  1  0
 12 20  1  0
 20 21  2  0
  5 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 29 36  2  0
 23  2  1  0
 36 25  1  0
 21  9  1  0
 35 30  1  0
 19 14  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  3 40  1  0
  4 41  1  0
  6 42  1  0
 10 43  1  0
 11 44  1  0
 13 45  1  0
 13 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 21 57  1  0
 22 58  1  0
 24 59  1  0
 27 60  1  0
 28 61  1  0
 31 62  1  0
 32 63  1  0
 33 64  1  0
 35 65  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 619                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-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       5.748  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.415  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.748   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.082   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.416   4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.082   3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.750   3.850   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.416   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.750   2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.083   4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.082   6.930   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.415   6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.081   6.160   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.415   8.470   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.748   9.240   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.748   6.930   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.081   4.620   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.414   6.160   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.414   4.620   0.000  0.00  0.00           C+0
CONECT    1   20                                                            
CONECT    2    9   10   13                                                  
CONECT    3   11   12                                                       
CONECT    4   20   21                                                       
CONECT    5   22   28                                                       
CONECT    6   28   29                                                       
CONECT    7   28   32                                                       
CONECT    8   34   36                                                       
CONECT    9    2   11                                                       
CONECT   10    2   12                                                       
CONECT   11    3    9                                                       
CONECT   12    3   10                                                       
CONECT   13    2   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   17                                                       
CONECT   16   14   18                                                       
CONECT   17   15   19                                                       
CONECT   18   16   19                                                       
CONECT   19   17   18   20                                                  
CONECT   20    1    4   19                                                  
CONECT   21    4   23   25                                                  
CONECT   22    5   23   24                                                  
CONECT   23   21   22                                                       
CONECT   24   22   26   27                                                  
CONECT   25   21   26                                                       
CONECT   26   24   25                                                       
CONECT   27   24                                                            
CONECT   28    5    6    7                                                  
CONECT   29    6   30   31                                                  
CONECT   30   29   33   34                                                  
CONECT   31   29   32                                                       
CONECT   32    7   31                                                       
CONECT   33   30   35                                                       
CONECT   34    8   30                                                       
CONECT   35   33   36                                                       
CONECT   36    8   35                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

COMPND    HMDB0013862
HETATM    1  C1  UNL     1       4.394   3.666  -2.794  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.180   2.902  -2.392  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.993   3.203  -2.963  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.842   2.528  -2.626  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.883   1.522  -1.690  1.00  0.00           C  
HETATM    6  N1  UNL     1      -0.260   0.774  -1.307  1.00  0.00           N  
HETATM    7  C6  UNL     1      -1.499   0.723  -1.956  1.00  0.00           C  
HETATM    8  O1  UNL     1      -1.704   1.375  -3.003  1.00  0.00           O  
HETATM    9  C7  UNL     1      -2.617  -0.090  -1.453  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.686  -0.308  -2.293  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.776  -1.057  -1.889  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.793  -1.596  -0.621  1.00  0.00           C  
HETATM   13  C11 UNL     1      -5.946  -2.410  -0.144  1.00  0.00           C  
HETATM   14  N2  UNL     1      -7.058  -1.576   0.249  1.00  0.00           N  
HETATM   15  C12 UNL     1      -8.132  -2.385   0.714  1.00  0.00           C  
HETATM   16  C13 UNL     1      -9.008  -1.632   1.664  1.00  0.00           C  
HETATM   17  N3  UNL     1      -9.010  -0.233   1.284  1.00  0.00           N  
HETATM   18  C14 UNL     1      -7.714   0.349   1.599  1.00  0.00           C  
HETATM   19  C15 UNL     1      -6.594  -0.603   1.215  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.730  -1.382   0.220  1.00  0.00           C  
HETATM   21  C17 UNL     1      -2.654  -0.635  -0.195  1.00  0.00           C  
HETATM   22  C18 UNL     1       2.118   1.225  -1.111  1.00  0.00           C  
HETATM   23  C19 UNL     1       3.259   1.888  -1.439  1.00  0.00           C  
HETATM   24  N4  UNL     1       4.531   1.626  -0.892  1.00  0.00           N  
HETATM   25  C20 UNL     1       4.785   0.646   0.101  1.00  0.00           C  
HETATM   26  N5  UNL     1       3.882  -0.160   0.661  1.00  0.00           N  
HETATM   27  C21 UNL     1       4.156  -1.077   1.597  1.00  0.00           C  
HETATM   28  C22 UNL     1       5.474  -1.233   2.048  1.00  0.00           C  
HETATM   29  C23 UNL     1       6.426  -0.424   1.495  1.00  0.00           C  
HETATM   30  C24 UNL     1       7.809  -0.542   1.922  1.00  0.00           C  
HETATM   31  C25 UNL     1       8.806   0.274   1.373  1.00  0.00           C  
HETATM   32  C26 UNL     1      10.105   0.158   1.771  1.00  0.00           C  
HETATM   33  C27 UNL     1      10.471  -0.765   2.725  1.00  0.00           C  
HETATM   34  N6  UNL     1       9.518  -1.546   3.251  1.00  0.00           N  
HETATM   35  C28 UNL     1       8.202  -1.443   2.860  1.00  0.00           C  
HETATM   36  N7  UNL     1       6.056   0.469   0.561  1.00  0.00           N  
HETATM   37  H1  UNL     1       4.153   4.362  -3.622  1.00  0.00           H  
HETATM   38  H2  UNL     1       4.733   4.307  -1.941  1.00  0.00           H  
HETATM   39  H3  UNL     1       5.200   3.002  -3.174  1.00  0.00           H  
HETATM   40  H4  UNL     1       1.925   3.996  -3.709  1.00  0.00           H  
HETATM   41  H5  UNL     1      -0.068   2.817  -3.105  1.00  0.00           H  
HETATM   42  H6  UNL     1      -0.156   0.188  -0.418  1.00  0.00           H  
HETATM   43  H7  UNL     1      -3.723   0.095  -3.304  1.00  0.00           H  
HETATM   44  H8  UNL     1      -5.611  -1.217  -2.569  1.00  0.00           H  
HETATM   45  H9  UNL     1      -5.581  -3.051   0.678  1.00  0.00           H  
HETATM   46  H10 UNL     1      -6.215  -3.095  -0.979  1.00  0.00           H  
HETATM   47  H11 UNL     1      -8.719  -2.721  -0.178  1.00  0.00           H  
HETATM   48  H12 UNL     1      -7.713  -3.260   1.254  1.00  0.00           H  
HETATM   49  H13 UNL     1      -8.609  -1.709   2.696  1.00  0.00           H  
HETATM   50  H14 UNL     1     -10.077  -1.967   1.603  1.00  0.00           H  
HETATM   51  H15 UNL     1      -9.235  -0.124   0.275  1.00  0.00           H  
HETATM   52  H16 UNL     1      -7.673   0.668   2.648  1.00  0.00           H  
HETATM   53  H17 UNL     1      -7.613   1.253   0.960  1.00  0.00           H  
HETATM   54  H18 UNL     1      -6.324  -1.156   2.134  1.00  0.00           H  
HETATM   55  H19 UNL     1      -5.724  -0.051   0.841  1.00  0.00           H  
HETATM   56  H20 UNL     1      -3.750  -1.817   1.234  1.00  0.00           H  
HETATM   57  H21 UNL     1      -1.821  -0.470   0.478  1.00  0.00           H  
HETATM   58  H22 UNL     1       2.096   0.421  -0.381  1.00  0.00           H  
HETATM   59  H23 UNL     1       5.371   2.186  -1.229  1.00  0.00           H  
HETATM   60  H24 UNL     1       3.343  -1.680   1.987  1.00  0.00           H  
HETATM   61  H25 UNL     1       5.653  -1.978   2.800  1.00  0.00           H  
HETATM   62  H26 UNL     1       8.500   0.985   0.633  1.00  0.00           H  
HETATM   63  H27 UNL     1      10.900   0.773   1.369  1.00  0.00           H  
HETATM   64  H28 UNL     1      11.516  -0.867   3.051  1.00  0.00           H  
HETATM   65  H29 UNL     1       7.510  -2.118   3.344  1.00  0.00           H  
CONECT    1    2   37   38   39
CONECT    2    3    3   23
CONECT    3    4   40
CONECT    4    5    5   41
CONECT    5    6   22
CONECT    6    7   42
CONECT    7    8    8    9
CONECT    9   10   10   21
CONECT   10   11   43
CONECT   11   12   12   44
CONECT   12   13   20
CONECT   13   14   45   46
CONECT   14   15   19
CONECT   15   16   47   48
CONECT   16   17   49   50
CONECT   17   18   51
CONECT   18   19   52   53
CONECT   19   54   55
CONECT   20   21   21   56
CONECT   21   57
CONECT   22   23   23   58
CONECT   23   24
CONECT   24   25   59
CONECT   25   26   26   36
CONECT   26   27
CONECT   27   28   28   60
CONECT   28   29   61
CONECT   29   30   36   36
CONECT   30   31   31   35
CONECT   31   32   62
CONECT   32   33   33   63
CONECT   33   34   64
CONECT   34   35   35
CONECT   35   65
END

HMDB0060621
     RDKit          3D
n-Demethylated piperazine
 65 69  0  0  0  0  0  0  0  0999 V2000
    4.4441   -0.8922    4.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2226   -0.6590    3.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0097   -0.6813    4.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8455   -0.4634    3.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8706   -0.2265    2.4370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2634   -0.0002    1.6421 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6026    0.0582    2.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9215   -0.1021    3.2300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6818    0.3039    1.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9861    0.5276    1.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0375    0.7588    0.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8379    0.7794   -0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9140    1.0184   -1.6517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2388    0.9403   -1.0637 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2567    1.2079   -2.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2297    0.2228   -3.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0815   -1.1434   -2.7337 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4545   -1.1787   -1.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4847   -0.3686   -0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5591    0.5616   -1.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5026    0.3283   -0.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1461   -0.2147    1.8398 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3082   -0.4199    2.5128 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5620   -0.4056    1.9049 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8741   -0.1851    0.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9822    0.0540   -0.3989 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2462    0.2668   -1.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5981    0.2283   -2.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5714   -0.0149   -1.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0114   -0.0613   -1.4717 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4670    0.1319   -2.7353 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8211    0.0729   -2.9855 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6769   -0.1812   -1.9438 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2374   -0.3735   -0.6919 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9212   -0.3157   -0.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1827   -0.2135    0.1513 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9156   -1.8733    4.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2156   -0.1109    4.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2168   -0.8550    5.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9663   -0.8673    5.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0590   -0.4958    4.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0815    0.1502    0.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1259    0.5081    2.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0313    0.9292    1.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7898    0.4182   -2.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7976    2.0938   -1.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2434    1.1853   -1.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0833    2.2283   -2.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3776    0.4276   -3.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1532    0.3420   -3.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1431   -1.5298   -2.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4910   -0.8082   -1.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4541   -2.2216   -0.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0380   -0.2040    0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5840   -0.9441   -0.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3812    0.5741   -2.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5393    0.1656   -0.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1461   -0.0277    0.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4027   -0.5874    2.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4782    0.4596   -2.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8329    0.3952   -3.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7566    0.3350   -3.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2163    0.2214   -3.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7674   -0.2394   -2.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5124   -0.4666    0.5582 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
 18 19  1  0
 12 20  1  0
 20 21  2  0
  5 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 29 36  2  0
 23  2  1  0
 36 25  1  0
 21  9  1  0
 35 30  1  0
 19 14  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  3 40  1  0
  4 41  1  0
  6 42  1  0
 10 43  1  0
 11 44  1  0
 13 45  1  0
 13 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 21 57  1  0
 22 58  1  0
 24 59  1  0
 27 60  1  0
 28 61  1  0
 31 62  1  0
 32 63  1  0
 33 64  1  0
 35 65  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
CGP74588	HMDB
N-Desmethylimatinib	MeSH

Chemical Formula

C₂₈H₂₉N₇O

Average Molecular Weight

479.5762

Monoisotopic Molecular Weight

479.243358585

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC1=C(NC2=NC=CC(=N2)C2=CN=CC=C2)C=C(NC(=O)C2=CC=C(CN3CCNCC3)C=C2)C=C1

InChI Identifier

InChI=1S/C28H29N7O/c1-20-4-9-24(17-26(20)34-28-31-12-10-25(33-28)23-3-2-11-30-18-23)32-27(36)22-7-5-21(6-8-22)19-35-15-13-29-14-16-35/h2-12,17-18,29H,13-16,19H2,1H3,(H,32,36)(H,31,33,34)

InChI Key

BQQYXPHRXIZMDM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Anilides

Direct Parent

Benzanilides

Alternative Parents

Substituents

Benzanilide
Pyridinylpyrimidine
Benzamide
Benzoic acid or derivatives
Diaminotoluene
Benzoyl
Benzylamine
Phenylmethylamine
Aniline or substituted anilines
Aminopyrimidine
Aralkylamine
Toluene
N-alkylpiperazine
1,4-diazinane
Piperazine
Pyridine
Pyrimidine
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Carboxamide group
Amino acid or derivatives
Secondary amine
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Secondary aliphatic amine
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Organonitrogen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060621)

Organ

Kidney (HMDB: HMDB0060621)
Liver (HMDB: HMDB0060621)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060621)

Cellular substructure

Cytoplasm (HMDB: HMDB0060621)
Membrane (HMDB: HMDB0060621)

Source

Endogenous

Endogenous (HMDB: HMDB0060621)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0066 g/L	ALOGPS
logP	3.16	ALOGPS
logP	3.99	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	12.46	ChemAxon
pKa (Strongest Basic)	9.25	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.07 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	143.63 m³·mol⁻¹	ChemAxon
Polarizability	53.39 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]+	215.857	31661259
DarkChem	[M-H]-	212.281	31661259
DeepCCS	[M+H]+	211.506	30932474
DeepCCS	[M-H]-	209.11	30932474
DeepCCS	[M-2H]-	241.993	30932474
DeepCCS	[M+Na]+	217.418	30932474
AllCCS	[M+H]+	219.6	32859911
AllCCS	[M+H-H2O]+	217.7	32859911
AllCCS	[M+NH4]+	221.3	32859911
AllCCS	[M+Na]+	221.8	32859911
AllCCS	[M-H]-	209.2	32859911
AllCCS	[M+Na-2H]-	209.9	32859911
AllCCS	[M+HCOO]-	210.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-desmethylimatinib	CC1=C(NC2=NC=CC(=N2)C2=CN=CC=C2)C=C(NC(=O)C2=CC=C(CN3CCNCC3)C=C2)C=C1	5455.1	Standard polar	33892256
N-desmethylimatinib	CC1=C(NC2=NC=CC(=N2)C2=CN=CC=C2)C=C(NC(=O)C2=CC=C(CN3CCNCC3)C=C2)C=C1	4589.5	Standard non polar	33892256
N-desmethylimatinib	CC1=C(NC2=NC=CC(=N2)C2=CN=CC=C2)C=C(NC(=O)C2=CC=C(CN3CCNCC3)C=C2)C=C1	5103.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-desmethylimatinib,1TMS,isomer #1	CC1=CC=C(NC(=O)C2=CC=C(CN3CCNCC3)C=C2)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C	4549.9	Semi standard non polar	33892256
N-desmethylimatinib,1TMS,isomer #1	CC1=CC=C(NC(=O)C2=CC=C(CN3CCNCC3)C=C2)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C	2943.1	Standard non polar	33892256
N-desmethylimatinib,1TMS,isomer #1	CC1=CC=C(NC(=O)C2=CC=C(CN3CCNCC3)C=C2)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C	5978.5	Standard polar	33892256
N-desmethylimatinib,1TMS,isomer #2	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCNCC3)C=C2)[Si](C)(C)C)C=C1NC1=NC=CC(C2=CC=CN=C2)=N1	4469.6	Semi standard non polar	33892256
N-desmethylimatinib,1TMS,isomer #2	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCNCC3)C=C2)[Si](C)(C)C)C=C1NC1=NC=CC(C2=CC=CN=C2)=N1	2596.2	Standard non polar	33892256
N-desmethylimatinib,1TMS,isomer #2	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCNCC3)C=C2)[Si](C)(C)C)C=C1NC1=NC=CC(C2=CC=CN=C2)=N1	6054.5	Standard polar	33892256
N-desmethylimatinib,1TMS,isomer #3	CC1=CC=C(NC(=O)C2=CC=C(CN3CCN([Si](C)(C)C)CC3)C=C2)C=C1NC1=NC=CC(C2=CC=CN=C2)=N1	4783.7	Semi standard non polar	33892256
N-desmethylimatinib,1TMS,isomer #3	CC1=CC=C(NC(=O)C2=CC=C(CN3CCN([Si](C)(C)C)CC3)C=C2)C=C1NC1=NC=CC(C2=CC=CN=C2)=N1	3041.1	Standard non polar	33892256
N-desmethylimatinib,1TMS,isomer #3	CC1=CC=C(NC(=O)C2=CC=C(CN3CCN([Si](C)(C)C)CC3)C=C2)C=C1NC1=NC=CC(C2=CC=CN=C2)=N1	6254.6	Standard polar	33892256
N-desmethylimatinib,2TMS,isomer #1	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCNCC3)C=C2)[Si](C)(C)C)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C	4253.5	Semi standard non polar	33892256
N-desmethylimatinib,2TMS,isomer #1	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCNCC3)C=C2)[Si](C)(C)C)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C	2762.9	Standard non polar	33892256
N-desmethylimatinib,2TMS,isomer #1	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCNCC3)C=C2)[Si](C)(C)C)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C	5607.5	Standard polar	33892256
N-desmethylimatinib,2TMS,isomer #2	CC1=CC=C(NC(=O)C2=CC=C(CN3CCN([Si](C)(C)C)CC3)C=C2)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C	4625.9	Semi standard non polar	33892256
N-desmethylimatinib,2TMS,isomer #2	CC1=CC=C(NC(=O)C2=CC=C(CN3CCN([Si](C)(C)C)CC3)C=C2)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C	3080.5	Standard non polar	33892256
N-desmethylimatinib,2TMS,isomer #2	CC1=CC=C(NC(=O)C2=CC=C(CN3CCN([Si](C)(C)C)CC3)C=C2)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C	5838.3	Standard polar	33892256
N-desmethylimatinib,2TMS,isomer #3	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN([Si](C)(C)C)CC3)C=C2)[Si](C)(C)C)C=C1NC1=NC=CC(C2=CC=CN=C2)=N1	4528.5	Semi standard non polar	33892256
N-desmethylimatinib,2TMS,isomer #3	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN([Si](C)(C)C)CC3)C=C2)[Si](C)(C)C)C=C1NC1=NC=CC(C2=CC=CN=C2)=N1	2817.7	Standard non polar	33892256
N-desmethylimatinib,2TMS,isomer #3	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN([Si](C)(C)C)CC3)C=C2)[Si](C)(C)C)C=C1NC1=NC=CC(C2=CC=CN=C2)=N1	5930.5	Standard polar	33892256
N-desmethylimatinib,3TMS,isomer #1	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN([Si](C)(C)C)CC3)C=C2)[Si](C)(C)C)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C	4368.8	Semi standard non polar	33892256
N-desmethylimatinib,3TMS,isomer #1	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN([Si](C)(C)C)CC3)C=C2)[Si](C)(C)C)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C	3033.6	Standard non polar	33892256
N-desmethylimatinib,3TMS,isomer #1	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN([Si](C)(C)C)CC3)C=C2)[Si](C)(C)C)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C	5498.0	Standard polar	33892256
N-desmethylimatinib,1TBDMS,isomer #1	CC1=CC=C(NC(=O)C2=CC=C(CN3CCNCC3)C=C2)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C(C)(C)C	4738.7	Semi standard non polar	33892256
N-desmethylimatinib,1TBDMS,isomer #1	CC1=CC=C(NC(=O)C2=CC=C(CN3CCNCC3)C=C2)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C(C)(C)C	3084.1	Standard non polar	33892256
N-desmethylimatinib,1TBDMS,isomer #1	CC1=CC=C(NC(=O)C2=CC=C(CN3CCNCC3)C=C2)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C(C)(C)C	5985.0	Standard polar	33892256
N-desmethylimatinib,1TBDMS,isomer #2	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCNCC3)C=C2)[Si](C)(C)C(C)(C)C)C=C1NC1=NC=CC(C2=CC=CN=C2)=N1	4670.5	Semi standard non polar	33892256
N-desmethylimatinib,1TBDMS,isomer #2	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCNCC3)C=C2)[Si](C)(C)C(C)(C)C)C=C1NC1=NC=CC(C2=CC=CN=C2)=N1	2754.4	Standard non polar	33892256
N-desmethylimatinib,1TBDMS,isomer #2	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCNCC3)C=C2)[Si](C)(C)C(C)(C)C)C=C1NC1=NC=CC(C2=CC=CN=C2)=N1	6080.5	Standard polar	33892256
N-desmethylimatinib,1TBDMS,isomer #3	CC1=CC=C(NC(=O)C2=CC=C(CN3CCN([Si](C)(C)C(C)(C)C)CC3)C=C2)C=C1NC1=NC=CC(C2=CC=CN=C2)=N1	5006.6	Semi standard non polar	33892256
N-desmethylimatinib,1TBDMS,isomer #3	CC1=CC=C(NC(=O)C2=CC=C(CN3CCN([Si](C)(C)C(C)(C)C)CC3)C=C2)C=C1NC1=NC=CC(C2=CC=CN=C2)=N1	3213.5	Standard non polar	33892256
N-desmethylimatinib,1TBDMS,isomer #3	CC1=CC=C(NC(=O)C2=CC=C(CN3CCN([Si](C)(C)C(C)(C)C)CC3)C=C2)C=C1NC1=NC=CC(C2=CC=CN=C2)=N1	6365.1	Standard polar	33892256
N-desmethylimatinib,2TBDMS,isomer #1	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCNCC3)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	4619.8	Semi standard non polar	33892256
N-desmethylimatinib,2TBDMS,isomer #1	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCNCC3)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	3162.5	Standard non polar	33892256
N-desmethylimatinib,2TBDMS,isomer #1	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCNCC3)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	5607.9	Standard polar	33892256
N-desmethylimatinib,2TBDMS,isomer #2	CC1=CC=C(NC(=O)C2=CC=C(CN3CCN([Si](C)(C)C(C)(C)C)CC3)C=C2)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C(C)(C)C	5002.2	Semi standard non polar	33892256
N-desmethylimatinib,2TBDMS,isomer #2	CC1=CC=C(NC(=O)C2=CC=C(CN3CCN([Si](C)(C)C(C)(C)C)CC3)C=C2)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C(C)(C)C	3577.4	Standard non polar	33892256
N-desmethylimatinib,2TBDMS,isomer #2	CC1=CC=C(NC(=O)C2=CC=C(CN3CCN([Si](C)(C)C(C)(C)C)CC3)C=C2)C=C1N(C1=NC=CC(C2=CC=CN=C2)=N1)[Si](C)(C)C(C)(C)C	5879.9	Standard polar	33892256
N-desmethylimatinib,2TBDMS,isomer #3	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN([Si](C)(C)C(C)(C)C)CC3)C=C2)[Si](C)(C)C(C)(C)C)C=C1NC1=NC=CC(C2=CC=CN=C2)=N1	4902.7	Semi standard non polar	33892256
N-desmethylimatinib,2TBDMS,isomer #3	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN([Si](C)(C)C(C)(C)C)CC3)C=C2)[Si](C)(C)C(C)(C)C)C=C1NC1=NC=CC(C2=CC=CN=C2)=N1	3304.2	Standard non polar	33892256
N-desmethylimatinib,2TBDMS,isomer #3	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN([Si](C)(C)C(C)(C)C)CC3)C=C2)[Si](C)(C)C(C)(C)C)C=C1NC1=NC=CC(C2=CC=CN=C2)=N1	6004.8	Standard polar	33892256
N-desmethylimatinib,3TBDMS,isomer #1	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN([Si](C)(C)C(C)(C)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	4895.5	Semi standard non polar	33892256
N-desmethylimatinib,3TBDMS,isomer #1	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN([Si](C)(C)C(C)(C)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	3869.9	Standard non polar	33892256
N-desmethylimatinib,3TBDMS,isomer #1	CC1=CC=C(N(C(=O)C2=CC=C(CN3CCN([Si](C)(C)C(C)(C)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	5569.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-desmethylimatinib GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f9f-9364300000-17e27cc3c2e4a0cb7501	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-desmethylimatinib GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-desmethylimatinib GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-desmethylimatinib GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylimatinib 10V, Positive-QTOF	splash10-001i-0144900000-dbf028ef8689f34d3771	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylimatinib 20V, Positive-QTOF	splash10-0f6x-1698400000-6206b8b45fb71b15fcdf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylimatinib 40V, Positive-QTOF	splash10-00mo-4921000000-dd971eb0dcec023353d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylimatinib 10V, Negative-QTOF	splash10-004i-1110900000-89aea60502d7f5f0c44a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylimatinib 20V, Negative-QTOF	splash10-004i-7535900000-6f9446f0c31d2b676c94	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylimatinib 40V, Negative-QTOF	splash10-0006-9400000000-e4bc361c68b0c77b4951	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylimatinib 10V, Positive-QTOF	splash10-001i-0012900000-e262520629e20a961261	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylimatinib 20V, Positive-QTOF	splash10-000x-0216900000-067251d7c51753fe745b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylimatinib 40V, Positive-QTOF	splash10-014i-1911200000-4f56c2b61ef41b6ae231	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylimatinib 10V, Negative-QTOF	splash10-004i-0000900000-f641f9627d4b7885f542	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylimatinib 20V, Negative-QTOF	splash10-004i-0000900000-1117c5bf89c63689dc39	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylimatinib 40V, Negative-QTOF	splash10-00b9-2555900000-0e278e7e9d60b24dc9aa	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9869737

PDB ID

Not Available

ChEBI ID

Not Available

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

Mlejnek P, Dolezel P, Faber E, Kosztyu P: Interactions of N-desmethyl imatinib, an active metabolite of imatinib, with P-glycoprotein in human leukemia cells. Ann Hematol. 2011 Jul;90(7):837-42. doi: 10.1007/s00277-010-1142-7. Epub 2011 Jan 12. [PubMed:21225261 ]
Nebot N, Crettol S, d'Esposito F, Tattam B, Hibbs DE, Murray M: Participation of CYP2C8 and CYP3A4 in the N-demethylation of imatinib in human hepatic microsomes. Br J Pharmacol. 2010 Nov;161(5):1059-69. doi: 10.1111/j.1476-5381.2010.00946.x. [PubMed:20977456 ]

Only showing the first 10 proteins. There are 19 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

2. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

4. Cytochrome P450 2C19

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

Enzyme Details

5. Epithelial discoidin domain-containing receptor 1

General function:: Involved in cell adhesion
Specific function:: May be involved in cell-cell interactions and recognition
Gene Name:: DDR1
Uniprot ID:: Q08345
Molecular weight:: 101126.7

References

Gotlib J, Berube C, Growney JD, Chen CC, George TI, Williams C, Kajiguchi T, Ruan J, Lilleberg SL, Durocher JA, Lichy JH, Wang Y, Cohen PS, Arber DA, Heinrich MC, Neckers L, Galli SJ, Gilliland DG, Coutre SE: Activity of the tyrosine kinase inhibitor PKC412 in a patient with mast cell leukemia with the D816V KIT mutation. Blood. 2005 Oct 15;106(8):2865-70. Epub 2005 Jun 21. [PubMed:15972446 ]
Xu L, Tong R, Cochran DM, Jain RK: Blocking platelet-derived growth factor-D/platelet-derived growth factor receptor beta signaling inhibits human renal cell carcinoma progression in an orthotopic mouse model. Cancer Res. 2005 Jul 1;65(13):5711-9. [PubMed:15994946 ]
Neef M, Ledermann M, Saegesser H, Schneider V, Widmer N, Decosterd LA, Rochat B, Reichen J: Oral imatinib treatment reduces early fibrogenesis but does not prevent progression in the long term. J Hepatol. 2006 Jan;44(1):167-75. Epub 2005 Jul 12. [PubMed:16168515 ]
Jubert C, Geoerger B, Grill J, Hartmann O, Vassal G: [Targeted therapies in pediatric oncology: a new therapeutic approach?]. Arch Pediatr. 2006 Feb;13(2):189-94. Epub 2005 Nov 17. [PubMed:16298518 ]
Benjamin RS, Blanke CD, Blay JY, Bonvalot S, Eisenberg B: Management of gastrointestinal stromal tumors in the imatinib era: selected case studies. Oncologist. 2006 Jan;11(1):9-20. [PubMed:16401709 ]

Enzyme Details

6. Macrophage colony-stimulating factor 1 receptor

General function:: Involved in protein kinase activity
Specific function:: Protein tyrosine-kinase transmembrane receptor for CSF1 and IL34
Gene Name:: CSF1R
Uniprot ID:: P07333
Molecular weight:: 107983.0

References

Dewar AL, Zannettino AC, Hughes TP, Lyons AB: Inhibition of c-fms by imatinib: expanding the spectrum of treatment. Cell Cycle. 2005 Jul;4(7):851-3. Epub 2005 Jul 28. [PubMed:15917650 ]
Taylor JR, Brownlow N, Domin J, Dibb NJ: FMS receptor for M-CSF (CSF-1) is sensitive to the kinase inhibitor imatinib and mutation of Asp-802 to Val confers resistance. Oncogene. 2006 Jan 5;25(1):147-51. [PubMed:16170366 ]
Dewar AL, Farrugia AN, Condina MR, Bik To L, Hughes TP, Vernon-Roberts B, Zannettino AC: Imatinib as a potential antiresorptive therapy for bone disease. Blood. 2006 Jun 1;107(11):4334-7. Epub 2006 Jan 31. [PubMed:16449525 ]
Ando W, Hashimoto J, Nampei A, Tsuboi H, Tateishi K, Ono T, Nakamura N, Ochi T, Yoshikawa H: Imatinib mesylate inhibits osteoclastogenesis and joint destruction in rats with collagen-induced arthritis (CIA). J Bone Miner Metab. 2006;24(4):274-82. [PubMed:16816921 ]
El Hajj Dib I, Gallet M, Mentaverri R, Sevenet N, Brazier M, Kamel S: Imatinib mesylate (Gleevec) enhances mature osteoclast apoptosis and suppresses osteoclast bone resorbing activity. Eur J Pharmacol. 2006 Dec 3;551(1-3):27-33. Epub 2006 Sep 16. [PubMed:17049513 ]

Enzyme Details

7. Alpha-type platelet-derived growth factor receptor

General function:: Involved in protein kinase activity
Specific function:: Receptor that binds both PDGFA and PDGFB and has a tyrosine-protein kinase activity
Gene Name:: PDGFRA
Uniprot ID:: P16234
Molecular weight:: 122668.5

References

Yi ES, Strong CR, Piao Z, Perucho M, Weidner N: Epithelioid gastrointestinal stromal tumor with PDGFRA activating mutation and immunoreactivity. Appl Immunohistochem Mol Morphol. 2005 Jun;13(2):157-61. [PubMed:15894928 ]
Borbenyi Z: [Disorders with eosinophilia, treatment of hypereosinophilic syndrome]. Orv Hetil. 2005 May 1;146(18 Suppl 1):911-6. [PubMed:15921304 ]
Corless CL, Schroeder A, Griffith D, Town A, McGreevey L, Harrell P, Shiraga S, Bainbridge T, Morich J, Heinrich MC: PDGFRA mutations in gastrointestinal stromal tumors: frequency, spectrum and in vitro sensitivity to imatinib. J Clin Oncol. 2005 Aug 10;23(23):5357-64. Epub 2005 May 31. [PubMed:15928335 ]
Chen LL, Sabripour M, Andtbacka RH, Patel SR, Feig BW, Macapinlac HA, Choi H, Wu EF, Frazier ML, Benjamin RS: Imatinib resistance in gastrointestinal stromal tumors. Curr Oncol Rep. 2005 Jul;7(4):293-9. [PubMed:15946589 ]
Tefferi A: Modern diagnosis and treatment of primary eosinophilia. Acta Haematol. 2005;114(1):52-60. [PubMed:15995325 ]

Enzyme Details

8. Tyrosine-protein kinase ABL1

General function:: Involved in non-membrane spanning protein tyrosine kinase activity
Specific function:: Protein kinase that regulates key processes linked to cell growth and survival. Regulates cytoskeleton remodeling during cell differentiation, cell division and cell adhesion. Localizes to dynamic actin structures, and phosphorylates CRK and CRKL, DOK1, and other proteins controlling cytoskeleton dynamics. Regulates DNA repair potentially by activating the proapoptotic pathway when the DNA damage is too severe to be repaired. Phosphorylates PSMA7 that leads to an inhibition of proteasomal activity and cell cycle transition blocks
Gene Name:: ABL1
Uniprot ID:: P00519
Molecular weight:: 122871.4

References

Hoerth E, Kodym R: Involvment of c-Abl in the radiation-induced inhibition of myoblast differentiation. Int J Radiat Biol. 2004 Oct;80(10):729-36. [PubMed:15799618 ]
Dewar AL, Zannettino AC, Hughes TP, Lyons AB: Inhibition of c-fms by imatinib: expanding the spectrum of treatment. Cell Cycle. 2005 Jul;4(7):851-3. Epub 2005 Jul 28. [PubMed:15917650 ]
Agirre X, Roman-Gomez J, Vazquez I, Jimenez-Velasco A, Larrayoz MJ, Lahortiga I, Andreu EJ, Marquez J, Beltran de Heredia JM, Odero MD, Prosper F, Calasanz MJ: Coexistence of different clonal populations harboring the b3a2 (p210) and e1a2 (p190) BCR-ABL1 fusion transcripts in chronic myelogenous leukemia resistant to imatinib. Cancer Genet Cytogenet. 2005 Jul 1;160(1):22-6. [PubMed:15949566 ]
Brueggemeier SB, Wu D, Kron SJ, Palecek SP: Protein-acrylamide copolymer hydrogels for array-based detection of tyrosine kinase activity from cell lysates. Biomacromolecules. 2005 Sep-Oct;6(5):2765-75. [PubMed:16153117 ]
Haberler C, Gelpi E, Marosi C, Rossler K, Birner P, Budka H, Hainfellner JA: Immunohistochemical analysis of platelet-derived growth factor receptor-alpha, -beta, c-kit, c-abl, and arg proteins in glioblastoma: possible implications for patient selection for imatinib mesylate therapy. J Neurooncol. 2006 Jan;76(2):105-9. [PubMed:16205964 ]

Enzyme Details

9. Beta-type platelet-derived growth factor receptor

General function:: Involved in protein kinase activity
Specific function:: Receptor that binds specifically to PDGFB and PDGFD and has a tyrosine-protein kinase activity. Phosphorylates Tyr residues at the C-terminus of PTPN11 creating a binding site for the SH2 domain of GRB2
Gene Name:: PDGFRB
Uniprot ID:: P09619
Molecular weight:: 123966.9

References

Basciani S, Brama M, Mariani S, De Luca G, Arizzi M, Vesci L, Pisano C, Dolci S, Spera G, Gnessi L: Imatinib mesylate inhibits Leydig cell tumor growth: evidence for in vitro and in vivo activity. Cancer Res. 2005 Mar 1;65(5):1897-903. [PubMed:15753388 ]
Jones RL, Judson IR: The development and application of imatinib. Expert Opin Drug Saf. 2005 Mar;4(2):183-91. [PubMed:15794712 ]
Modi S, Seidman AD, Dickler M, Moasser M, D'Andrea G, Moynahan ME, Menell J, Panageas KS, Tan LK, Norton L, Hudis CA: A phase II trial of imatinib mesylate monotherapy in patients with metastatic breast cancer. Breast Cancer Res Treat. 2005 Mar;90(2):157-63. [PubMed:15803362 ]
Johnson FM, Saigal B, Donato NJ: Induction of heparin-binding EGF-like growth factor and activation of EGF receptor in imatinib mesylate-treated squamous carcinoma cells. J Cell Physiol. 2005 Nov;205(2):218-27. [PubMed:15887238 ]
Chen J, Rocken C, Nitsche B, Hosius C, Gschaidmeier H, Kahl S, Malfertheiner P, Ebert MP: The tyrosine kinase inhibitor imatinib fails to inhibit pancreatic cancer progression. Cancer Lett. 2006 Feb 28;233(2):328-37. [PubMed:15893416 ]

Enzyme Details

10. High affinity nerve growth factor receptor

General function:: Involved in protein kinase activity
Specific function:: Required for high-affinity binding to nerve growth factor (NGF), neurotrophin-3 and neurotrophin-4/5 but not brain- derived neurotrophic factor (BDNF). Known substrates for the Trk receptors are SHC1, PI 3-kinase, and PLC-gamma-1. Has a crucial role in the development and function of the nociceptive reception system as well as establishment of thermal regulation via sweating. Activates ERK1 by either SHC1- or PLC-gamma-1-dependent signaling pathway
Gene Name:: NTRK1
Uniprot ID:: P04629
Molecular weight:: 87496.5

References

Catani M, De Milito R, Simi M: [New orientations in the management of advanced, metastatic gastrointestinal stromal tumors (GIST): combination of surgery and systemic therapy with imatinib in a case of primary gastric location]. Chir Ital. 2005 Jan-Feb;57(1):127-33. [PubMed:15832750 ]
Kovacs M, Nagy P, Pak G, Feher J: [Gastrointestinal stromal tumors (GISTs): clinical and pathological features]. Orv Hetil. 2005 Jun 26;146(26):1375-81. [PubMed:16052979 ]
de Groot JW, Plaza Menacho I, Schepers H, Drenth-Diephuis LJ, Osinga J, Plukker JT, Links TP, Eggen BJ, Hofstra RM: Cellular effects of imatinib on medullary thyroid cancer cells harboring multiple endocrine neoplasia Type 2A and 2B associated RET mutations. Surgery. 2006 Jun;139(6):806-14. [PubMed:16782438 ]
de Groot JW, Zonnenberg BA, van Ufford-Mannesse PQ, de Vries MM, Links TP, Lips CJ, Voest EE: A phase II trial of imatinib therapy for metastatic medullary thyroid carcinoma. J Clin Endocrinol Metab. 2007 Sep;92(9):3466-9. Epub 2007 Jun 19. [PubMed:17579194 ]
Delbaldo C: [Pharmacokinetic-pharmacodynamics relationships of imatinib (Glivec)]. Therapie. 2007 Mar-Apr;62(2):87-90. Epub 2007 Jun 21. [PubMed:17582306 ]

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

Davies A, Jordanides NE, Giannoudis A, Lucas CM, Hatziieremia S, Harris RJ, Jorgensen HG, Holyoake TL, Pirmohamed M, Clark RE, Mountford JC: Nilotinib concentration in cell lines and primary CD34(+) chronic myeloid leukemia cells is not mediated by active uptake or efflux by major drug transporters. Leukemia. 2009 Nov;23(11):1999-2006. doi: 10.1038/leu.2009.166. Epub 2009 Aug 27. [PubMed:19710702 ]
Dohse M, Scharenberg C, Shukla S, Robey RW, Volkmann T, Deeken JF, Brendel C, Ambudkar SV, Neubauer A, Bates SE: Comparison of ATP-binding cassette transporter interactions with the tyrosine kinase inhibitors imatinib, nilotinib, and dasatinib. Drug Metab Dispos. 2010 Aug;38(8):1371-80. doi: 10.1124/dmd.109.031302. Epub 2010 Apr 27. [PubMed:20423956 ]
Hamada A, Miyano H, Watanabe H, Saito H: Interaction of imatinib mesilate with human P-glycoprotein. J Pharmacol Exp Ther. 2003 Nov;307(2):824-8. Epub 2003 Sep 15. [PubMed:12975485 ]
Thomas J, Wang L, Clark RE, Pirmohamed M: Active transport of imatinib into and out of cells: implications for drug resistance. Blood. 2004 Dec 1;104(12):3739-45. Epub 2004 Aug 17. [PubMed:15315971 ]
Hegedus C, Ozvegy-Laczka C, Apati A, Magocsi M, Nemet K, Orfi L, Keri G, Katona M, Takats Z, Varadi A, Szakacs G, Sarkadi B: Interaction of nilotinib, dasatinib and bosutinib with ABCB1 and ABCG2: implications for altered anti-cancer effects and pharmacological properties. Br J Pharmacol. 2009 Oct;158(4):1153-64. doi: 10.1111/j.1476-5381.2009.00383.x. Epub 2009 Sep 28. [PubMed:19785662 ]
Giannoudis A, Davies A, Lucas CM, Harris RJ, Pirmohamed M, Clark RE: Effective dasatinib uptake may occur without human organic cation transporter 1 (hOCT1): implications for the treatment of imatinib-resistant chronic myeloid leukemia. Blood. 2008 Oct 15;112(8):3348-54. doi: 10.1182/blood-2007-10-116236. Epub 2008 Jul 31. [PubMed:18669873 ]
Breedveld P, Pluim D, Cipriani G, Wielinga P, van Tellingen O, Schinkel AH, Schellens JH: The effect of Bcrp1 (Abcg2) on the in vivo pharmacokinetics and brain penetration of imatinib mesylate (Gleevec): implications for the use of breast cancer resistance protein and P-glycoprotein inhibitors to enable the brain penetration of imatinib in patients. Cancer Res. 2005 Apr 1;65(7):2577-82. [PubMed:15805252 ]
Oka M, Fukuda M, Soda H: [Anticancer drugs and ABC transporters]. Gan To Kagaku Ryoho. 2005 May;32(5):585-92. [PubMed:15918555 ]
Burger H, van Tol H, Brok M, Wiemer EA, de Bruijn EA, Guetens G, de Boeck G, Sparreboom A, Verweij J, Nooter K: Chronic imatinib mesylate exposure leads to reduced intracellular drug accumulation by induction of the ABCG2 (BCRP) and ABCB1 (MDR1) drug transport pumps. Cancer Biol Ther. 2005 Jul;4(7):747-52. Epub 2005 Jul 9. [PubMed:15970668 ]
Galimberti S, Cervetti G, Guerrini F, Testi R, Pacini S, Fazzi R, Simi P, Petrini M: Quantitative molecular monitoring of BCR-ABL and MDR1 transcripts in patients with chronic myeloid leukemia during Imatinib treatment. Cancer Genet Cytogenet. 2005 Oct 1;162(1):57-62. [PubMed:16157201 ]
Gardner ER, Burger H, van Schaik RH, van Oosterom AT, de Bruijn EA, Guetens G, Prenen H, de Jong FA, Baker SD, Bates SE, Figg WD, Verweij J, Sparreboom A, Nooter K: Association of enzyme and transporter genotypes with the pharmacokinetics of imatinib. Clin Pharmacol Ther. 2006 Aug;80(2):192-201. [PubMed:16890580 ]

Enzyme Details

2. ATP-binding cassette sub-family G member 2

General function:: Involved in ATP binding
Specific function:: Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:: ABCG2
Uniprot ID:: Q9UNQ0
Molecular weight:: 72313.5

References

Houghton PJ, Germain GS, Harwood FC, Schuetz JD, Stewart CF, Buchdunger E, Traxler P: Imatinib mesylate is a potent inhibitor of the ABCG2 (BCRP) transporter and reverses resistance to topotecan and SN-38 in vitro. Cancer Res. 2004 Apr 1;64(7):2333-7. [PubMed:15059881 ]
An Y, Ongkeko WM: ABCG2: the key to chemoresistance in cancer stem cells? Expert Opin Drug Metab Toxicol. 2009 Dec;5(12):1529-42. doi: 10.1517/17425250903228834. [PubMed:19708828 ]
Davies A, Jordanides NE, Giannoudis A, Lucas CM, Hatziieremia S, Harris RJ, Jorgensen HG, Holyoake TL, Pirmohamed M, Clark RE, Mountford JC: Nilotinib concentration in cell lines and primary CD34(+) chronic myeloid leukemia cells is not mediated by active uptake or efflux by major drug transporters. Leukemia. 2009 Nov;23(11):1999-2006. doi: 10.1038/leu.2009.166. Epub 2009 Aug 27. [PubMed:19710702 ]
Dohse M, Scharenberg C, Shukla S, Robey RW, Volkmann T, Deeken JF, Brendel C, Ambudkar SV, Neubauer A, Bates SE: Comparison of ATP-binding cassette transporter interactions with the tyrosine kinase inhibitors imatinib, nilotinib, and dasatinib. Drug Metab Dispos. 2010 Aug;38(8):1371-80. doi: 10.1124/dmd.109.031302. Epub 2010 Apr 27. [PubMed:20423956 ]
Burger H, van Tol H, Boersma AW, Brok M, Wiemer EA, Stoter G, Nooter K: Imatinib mesylate (STI571) is a substrate for the breast cancer resistance protein (BCRP)/ABCG2 drug pump. Blood. 2004 Nov 1;104(9):2940-2. Epub 2004 Jul 13. [PubMed:15251980 ]
Hegedus C, Ozvegy-Laczka C, Apati A, Magocsi M, Nemet K, Orfi L, Keri G, Katona M, Takats Z, Varadi A, Szakacs G, Sarkadi B: Interaction of nilotinib, dasatinib and bosutinib with ABCB1 and ABCG2: implications for altered anti-cancer effects and pharmacological properties. Br J Pharmacol. 2009 Oct;158(4):1153-64. doi: 10.1111/j.1476-5381.2009.00383.x. Epub 2009 Sep 28. [PubMed:19785662 ]
Breedveld P, Pluim D, Cipriani G, Wielinga P, van Tellingen O, Schinkel AH, Schellens JH: The effect of Bcrp1 (Abcg2) on the in vivo pharmacokinetics and brain penetration of imatinib mesylate (Gleevec): implications for the use of breast cancer resistance protein and P-glycoprotein inhibitors to enable the brain penetration of imatinib in patients. Cancer Res. 2005 Apr 1;65(7):2577-82. [PubMed:15805252 ]
Oka M, Fukuda M, Soda H: [Anticancer drugs and ABC transporters]. Gan To Kagaku Ryoho. 2005 May;32(5):585-92. [PubMed:15918555 ]
Burger H, van Tol H, Brok M, Wiemer EA, de Bruijn EA, Guetens G, de Boeck G, Sparreboom A, Verweij J, Nooter K: Chronic imatinib mesylate exposure leads to reduced intracellular drug accumulation by induction of the ABCG2 (BCRP) and ABCB1 (MDR1) drug transport pumps. Cancer Biol Ther. 2005 Jul;4(7):747-52. Epub 2005 Jul 9. [PubMed:15970668 ]
Yanase K, Tsukahara S, Mitsuhashi J, Sugimoto Y: Functional SNPs of the breast cancer resistance protein-therapeutic effects and inhibitor development. Cancer Lett. 2006 Mar 8;234(1):73-80. Epub 2005 Nov 21. [PubMed:16303243 ]
Nakanishi T, Shiozawa K, Hassel BA, Ross DD: Complex interaction of BCRP/ABCG2 and imatinib in BCR-ABL-expressing cells: BCRP-mediated resistance to imatinib is attenuated by imatinib-induced reduction of BCRP expression. Blood. 2006 Jul 15;108(2):678-84. Epub 2006 Mar 16. [PubMed:16543472 ]

Enzyme Details

3. Solute carrier family 22 member 1

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

References

Davies A, Jordanides NE, Giannoudis A, Lucas CM, Hatziieremia S, Harris RJ, Jorgensen HG, Holyoake TL, Pirmohamed M, Clark RE, Mountford JC: Nilotinib concentration in cell lines and primary CD34(+) chronic myeloid leukemia cells is not mediated by active uptake or efflux by major drug transporters. Leukemia. 2009 Nov;23(11):1999-2006. doi: 10.1038/leu.2009.166. Epub 2009 Aug 27. [PubMed:19710702 ]
Engler JR, Frede A, Saunders VA, Zannettino AC, Hughes TP, White DL: Chronic myeloid leukemia CD34+ cells have reduced uptake of imatinib due to low OCT-1 activity. Leukemia. 2010 Apr;24(4):765-70. doi: 10.1038/leu.2010.16. Epub 2010 Feb 11. [PubMed:20147974 ]
Ahlin G, Karlsson J, Pedersen JM, Gustavsson L, Larsson R, Matsson P, Norinder U, Bergstrom CA, Artursson P: Structural requirements for drug inhibition of the liver specific human organic cation transport protein 1. J Med Chem. 2008 Oct 9;51(19):5932-42. doi: 10.1021/jm8003152. Epub 2008 Sep 13. [PubMed:18788725 ]

Enzyme Details

4. Solute carrier family 22 member 2

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

References

Tanihara Y, Masuda S, Katsura T, Inui K: Protective effect of concomitant administration of imatinib on cisplatin-induced nephrotoxicity focusing on renal organic cation transporter OCT2. Biochem Pharmacol. 2009 Nov 1;78(9):1263-71. doi: 10.1016/j.bcp.2009.06.014. Epub 2009 Jun 18. [PubMed:19540211 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Only showing the first 10 proteins. There are 19 proteins in total.

Show all enzymes and transporters

Showing metabocard for N-desmethylimatinib (HMDB0013862)

MOL for HMDB0013862 (N-desmethylimatinib)

3D MOL for HMDB0013862 (N-desmethylimatinib)

3D SDF for HMDB0013862 (N-desmethylimatinib)

3D-SDF for HMDB0013862 (N-desmethylimatinib)

PDB for HMDB0013862 (N-desmethylimatinib)

3D PDB for HMDB0013862 (N-desmethylimatinib)

SMILES for HMDB0013862 (N-desmethylimatinib)

INCHI for HMDB0013862 (N-desmethylimatinib)

Structure for HMDB0013862 (N-desmethylimatinib)

3D Structure for HMDB0013862 (N-desmethylimatinib)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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Transporters

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