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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8)transporters (2) Show 10 proteins XML

enzymes (8)transporters (2) Show 10 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:02 UTC

HMDB ID

HMDB0015595

Secondary Accession Numbers

HMDB15595

Metabolite Identification

Common Name

Nilotinib

Description

Nilotinib, also known as AMN107, is a tyrosine kinase inhibitor under investigation as a possible treatment for chronic myelogenous leukemia (CML). In June 2006, a Phase I clinical trial found nilotinib has a relatively favorable safety profile and shows activity in cases of CML resistant to treatment with imatinib (Gleevec®), another tyrosine kinase inhibitor currently used as a first-line treatment. [Wikipedia ]

Structure

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


  Mrv0541 02231217582D          

 39 43  0  0  0  0            999 V2000
    1.9520    2.2210    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    0.7920    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.0941    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.2690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    3.9816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.5066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -1.7935    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810    5.2512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -3.0310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.7935    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -5.5061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    3.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -0.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9370   -0.5560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.6815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610    4.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.6815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    0.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1261    4.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2060    5.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -0.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -2.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6910    5.9186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -3.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -4.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -3.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -4.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -4.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -5.5061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -5.9186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 26  1  0  0  0  0
  2 26  1  0  0  0  0
  3 26  1  0  0  0  0
  4 22  2  0  0  0  0
  5 12  1  0  0  0  0
  5 23  1  0  0  0  0
  5 27  1  0  0  0  0
  6 13  1  0  0  0  0
  6 22  1  0  0  0  0
  7 19  1  0  0  0  0
  7 30  1  0  0  0  0
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 33 36  1  0  0  0  0
 33 37  2  0  0  0  0
 34 35  2  0  0  0  0
 36 38  2  0  0  0  0
 38 39  1  0  0  0  0
M  END

HMDB0015595
     RDKit          3D
Nilotinib
 61 65  0  0  0  0  0  0  0  0999 V2000
  -10.6962   -0.1290   -0.0962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2286   -0.2457    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1955    0.3711   -0.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0121    0.0166   -0.0397 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6786    0.4166   -0.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5941   -0.2914   -0.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2745    0.0439   -0.4005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1978   -0.7375    0.0662 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9020   -0.7168   -0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5431   -0.0083   -1.4067 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1757   -1.5581    0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938   -2.8144    0.6363 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8876   -3.5979    1.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2028   -3.1313    1.2960 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2719   -3.9674    1.8863 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4711   -1.8645    0.7805 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8082   -1.4227    0.9553 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4126   -0.3401    0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7970    0.3751   -0.6937 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3356    1.4155   -1.3505 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6208    1.7519   -0.9965 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3247    1.0732   -0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6579    1.4814    0.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3076    0.8094    1.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5694    1.1954    1.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1942    2.2377    1.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5637    2.8787    0.1526 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3238    2.5121   -0.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6895    0.0433    0.5680 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4749   -1.1036    0.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1820    1.1709   -1.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2503    1.9224   -1.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0492    3.1285   -2.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8705    4.1163   -1.9740 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7213    3.5206   -2.4705 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4917    2.7892   -3.7329 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5120    1.5304   -1.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2673   -0.8217    0.9856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6279   -0.9744    1.0817 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2427   -0.9391    0.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8886   -0.0322   -1.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0631    0.8243    0.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3283    1.0401   -1.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.5165   -1.2749    1.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  3  4  1  0
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  5  6  2  0
  6  7  1  0
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 22 29  2  0
 16 30  2  0
  7 31  2  0
 31 32  1  0
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 33 34  1  0
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 33 36  1  0
 32 37  2  0
  4 38  1  0
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 38 61  1  0
M  END


  Mrv0541 02231217582D          

 39 43  0  0  0  0            999 V2000
    1.9520    2.2210    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    0.7920    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.0941    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.2690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    3.9816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.5066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -1.7935    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810    5.2512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -3.0310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.7935    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -5.5061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    3.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -0.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -0.5560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.5560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.6815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610    4.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5080   -5.5061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -5.9186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 26  1  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0015595

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CN(C=N1)C1=CC(=CC(NC(=O)C2=CC(NC3=NC=CC(=N3)C3=CN=CC=C3)=C(C)C=C2)=C1)C(F)(F)F

> <INCHI_IDENTIFIER>
InChI=1S/C28H22F3N7O/c1-17-5-6-19(10-25(17)37-27-33-9-7-24(36-27)20-4-3-8-32-14-20)26(39)35-22-11-21(28(29,30)31)12-23(13-22)38-15-18(2)34-16-38/h3-16H,1-2H3,(H,35,39)(H,33,36,37)

> <INCHI_KEY>
HHZIURLSWUIHRB-UHFFFAOYSA-N

> <FORMULA>
C28H22F3N7O

> <MOLECULAR_WEIGHT>
529.5158

> <EXACT_MASS>
529.183792976

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
52.346903933188045

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzamide

> <ALOGPS_LOGP>
4.51

> <JCHEM_LOGP>
4.407699999999998

> <ALOGPS_LOGS>
-5.42

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.466664680071862

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.863355086170097

> <JCHEM_PKA_STRONGEST_BASIC>
6.29797186941306

> <JCHEM_POLAR_SURFACE_AREA>
97.62

> <JCHEM_REFRACTIVITY>
152.85009999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.01e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nilotinib

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015595
     RDKit          3D
Nilotinib
 61 65  0  0  0  0  0  0  0  0999 V2000
  -10.6962   -0.1290   -0.0962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2286   -0.2457    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1955    0.3711   -0.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0121    0.0166   -0.0397 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6786    0.4166   -0.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5941   -0.2914   -0.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2745    0.0439   -0.4005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1978   -0.7375    0.0662 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9020   -0.7168   -0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5431   -0.0083   -1.4067 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1757   -1.5581    0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938   -2.8144    0.6363 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8876   -3.5979    1.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2028   -3.1313    1.2960 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2719   -3.9674    1.8863 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4711   -1.8645    0.7805 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8082   -1.4227    0.9553 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4126   -0.3401    0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7970    0.3751   -0.6937 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3356    1.4155   -1.3505 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6208    1.7519   -0.9965 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3247    1.0732   -0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6579    1.4814    0.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3076    0.8094    1.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5694    1.1954    1.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1942    2.2377    1.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5637    2.8787    0.1526 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3238    2.5121   -0.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6895    0.0433    0.5680 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4749   -1.1036    0.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1820    1.1709   -1.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2503    1.9224   -1.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0492    3.1285   -2.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8705    4.1163   -1.9740 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7213    3.5206   -2.4705 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4917    2.7892   -3.7329 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5120    1.5304   -1.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2673   -0.8217    0.9856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6279   -0.9744    1.0817 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2427   -0.9391    0.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8886   -0.0322   -1.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0631    0.8243    0.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3283    1.0401   -1.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7545   -1.1587    0.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3998   -1.3887    0.8843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1248   -3.1861    0.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6641   -4.5816    1.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2287   -3.9326    1.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3713   -3.7797    2.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9238   -5.0355    1.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4508   -1.9197    1.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8387    1.9795   -2.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0613    2.5848   -1.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8276   -0.0276    1.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0387    0.6452    2.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2094    2.5166    1.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8765    3.0784   -1.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7053   -0.1022   -0.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1770    1.5129   -1.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4011    2.1013   -1.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5165   -1.2749    1.6126 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 22 29  2  0
 16 30  2  0
  7 31  2  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  1  0
 33 36  1  0
 32 37  2  0
  4 38  1  0
 38 39  2  0
 39  2  1  0
 37  5  1  0
 30 11  1  0
 29 18  1  0
 28 23  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  3 43  1  0
  6 44  1  0
  8 45  1  0
 12 46  1  0
 13 47  1  0
 15 48  1  0
 15 49  1  0
 15 50  1  0
 17 51  1  0
 20 52  1  0
 21 53  1  0
 24 54  1  0
 25 55  1  0
 26 56  1  0
 28 57  1  0
 30 58  1  0
 31 59  1  0
 37 60  1  0
 38 61  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0       3.644   4.146   0.000  0.00  0.00           F+0
HETATM    2  F   UNK     0       5.184   1.478   0.000  0.00  0.00           F+0
HETATM    3  F   UNK     0       3.080   2.042   0.000  0.00  0.00           F+0
HETATM    4  O   UNK     0       8.415   0.502   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       7.081   7.432   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       9.748   2.812   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      12.416  -3.348   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       6.311   9.802   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      11.082  -5.658   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       9.748  -3.348   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      11.082 -10.278   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       7.081   5.892   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415   3.582   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.748   3.582   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.415   5.122   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748   5.122   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.081   2.812   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.082   0.502   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.416  -1.808   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.750  -1.038   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.082  -1.038   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.748   1.272   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.327   8.338   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.416   1.272   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.750   0.502   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.414   2.812   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.835   8.338   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.851   9.802   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.083  -1.808   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.082  -4.118   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.757  11.048   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.748  -6.428   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.748  -7.968   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.415  -5.658   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.415  -4.118   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.415  -8.738   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      11.082  -8.738   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.415 -10.278   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.748 -11.048   0.000  0.00  0.00           C+0
CONECT    1   26                                                            
CONECT    2   26                                                            
CONECT    3   26                                                            
CONECT    4   22                                                            
CONECT    5   12   23   27                                                  
CONECT    6   13   22                                                       
CONECT    7   19   30                                                       
CONECT    8   27   28                                                       
CONECT    9   30   32                                                       
CONECT   10   30   35                                                       
CONECT   11   37   39                                                       
CONECT   12    5   15   16                                                  
CONECT   13    6   15   17                                                  
CONECT   14   16   17   26                                                  
CONECT   15   12   13                                                       
CONECT   16   12   14                                                       
CONECT   17   13   14                                                       
CONECT   18   21   22   24                                                  
CONECT   19    7   20   21                                                  
CONECT   20   19   25   29                                                  
CONECT   21   18   19                                                       
CONECT   22    4    6   18                                                  
CONECT   23    5   28                                                       
CONECT   24   18   25                                                       
CONECT   25   20   24                                                       
CONECT   26    1    2    3   14                                             
CONECT   27    5    8                                                       
CONECT   28    8   23   31                                                  
CONECT   29   20                                                            
CONECT   30    7    9   10                                                  
CONECT   31   28                                                            
CONECT   32    9   33   34                                                  
CONECT   33   32   36   37                                                  
CONECT   34   32   35                                                       
CONECT   35   10   34                                                       
CONECT   36   33   38                                                       
CONECT   37   11   33                                                       
CONECT   38   36   39                                                       
CONECT   39   11   38                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

COMPND    HMDB0015595
HETATM    1  C1  UNL     1     -10.696  -0.129  -0.096  1.00  0.00           C  
HETATM    2  C2  UNL     1      -9.229  -0.246   0.135  1.00  0.00           C  
HETATM    3  C3  UNL     1      -8.196   0.371  -0.560  1.00  0.00           C  
HETATM    4  N1  UNL     1      -7.012   0.017  -0.040  1.00  0.00           N  
HETATM    5  C4  UNL     1      -5.679   0.417  -0.446  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.594  -0.291  -0.053  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.274   0.044  -0.401  1.00  0.00           C  
HETATM    8  N2  UNL     1      -2.198  -0.738   0.066  1.00  0.00           N  
HETATM    9  C7  UNL     1      -0.902  -0.717  -0.448  1.00  0.00           C  
HETATM   10  O1  UNL     1      -0.543  -0.008  -1.407  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.176  -1.558   0.124  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.094  -2.814   0.636  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.888  -3.598   1.214  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.203  -3.131   1.296  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.272  -3.967   1.886  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.471  -1.864   0.781  1.00  0.00           C  
HETATM   17  N3  UNL     1       3.808  -1.423   0.955  1.00  0.00           N  
HETATM   18  C14 UNL     1       4.413  -0.340   0.262  1.00  0.00           C  
HETATM   19  N4  UNL     1       3.797   0.375  -0.694  1.00  0.00           N  
HETATM   20  C15 UNL     1       4.336   1.415  -1.351  1.00  0.00           C  
HETATM   21  C16 UNL     1       5.621   1.752  -0.996  1.00  0.00           C  
HETATM   22  C17 UNL     1       6.325   1.073  -0.028  1.00  0.00           C  
HETATM   23  C18 UNL     1       7.658   1.481   0.355  1.00  0.00           C  
HETATM   24  C19 UNL     1       8.308   0.809   1.391  1.00  0.00           C  
HETATM   25  C20 UNL     1       9.569   1.195   1.779  1.00  0.00           C  
HETATM   26  C21 UNL     1      10.194   2.238   1.152  1.00  0.00           C  
HETATM   27  N5  UNL     1       9.564   2.879   0.153  1.00  0.00           N  
HETATM   28  C22 UNL     1       8.324   2.512  -0.242  1.00  0.00           C  
HETATM   29  N6  UNL     1       5.689   0.043   0.568  1.00  0.00           N  
HETATM   30  C23 UNL     1       1.475  -1.104   0.210  1.00  0.00           C  
HETATM   31  C24 UNL     1      -3.182   1.171  -1.185  1.00  0.00           C  
HETATM   32  C25 UNL     1      -4.250   1.922  -1.611  1.00  0.00           C  
HETATM   33  C26 UNL     1      -4.049   3.128  -2.481  1.00  0.00           C  
HETATM   34  F1  UNL     1      -4.870   4.116  -1.974  1.00  0.00           F  
HETATM   35  F2  UNL     1      -2.721   3.521  -2.471  1.00  0.00           F  
HETATM   36  F3  UNL     1      -4.492   2.789  -3.733  1.00  0.00           F  
HETATM   37  C27 UNL     1      -5.512   1.530  -1.229  1.00  0.00           C  
HETATM   38  C28 UNL     1      -7.267  -0.822   0.986  1.00  0.00           C  
HETATM   39  N7  UNL     1      -8.628  -0.974   1.082  1.00  0.00           N  
HETATM   40  H1  UNL     1     -11.243  -0.939   0.387  1.00  0.00           H  
HETATM   41  H2  UNL     1     -10.889  -0.032  -1.196  1.00  0.00           H  
HETATM   42  H3  UNL     1     -11.063   0.824   0.373  1.00  0.00           H  
HETATM   43  H4  UNL     1      -8.328   1.040  -1.403  1.00  0.00           H  
HETATM   44  H5  UNL     1      -4.755  -1.159   0.574  1.00  0.00           H  
HETATM   45  H6  UNL     1      -2.400  -1.389   0.884  1.00  0.00           H  
HETATM   46  H7  UNL     1      -1.125  -3.186   0.556  1.00  0.00           H  
HETATM   47  H8  UNL     1       0.664  -4.582   1.598  1.00  0.00           H  
HETATM   48  H9  UNL     1       4.229  -3.933   1.300  1.00  0.00           H  
HETATM   49  H10 UNL     1       3.371  -3.780   2.953  1.00  0.00           H  
HETATM   50  H11 UNL     1       2.924  -5.035   1.783  1.00  0.00           H  
HETATM   51  H12 UNL     1       4.451  -1.920   1.644  1.00  0.00           H  
HETATM   52  H13 UNL     1       3.839   1.979  -2.110  1.00  0.00           H  
HETATM   53  H14 UNL     1       6.061   2.585  -1.525  1.00  0.00           H  
HETATM   54  H15 UNL     1       7.828  -0.028   1.899  1.00  0.00           H  
HETATM   55  H16 UNL     1      10.039   0.645   2.601  1.00  0.00           H  
HETATM   56  H17 UNL     1      11.209   2.517   1.482  1.00  0.00           H  
HETATM   57  H18 UNL     1       7.877   3.078  -1.087  1.00  0.00           H  
HETATM   58  H19 UNL     1       1.705  -0.102  -0.175  1.00  0.00           H  
HETATM   59  H20 UNL     1      -2.177   1.513  -1.502  1.00  0.00           H  
HETATM   60  H21 UNL     1      -6.401   2.101  -1.525  1.00  0.00           H  
HETATM   61  H22 UNL     1      -6.517  -1.275   1.613  1.00  0.00           H  
CONECT    1    2   40   41   42
CONECT    2    3    3   39
CONECT    3    4   43
CONECT    4    5   38
CONECT    5    6    6   37
CONECT    6    7   44
CONECT    7    8   31   31
CONECT    8    9   45
CONECT    9   10   10   11
CONECT   11   12   12   30
CONECT   12   13   46
CONECT   13   14   14   47
CONECT   14   15   16
CONECT   15   48   49   50
CONECT   16   17   30   30
CONECT   17   18   51
CONECT   18   19   19   29
CONECT   19   20
CONECT   20   21   21   52
CONECT   21   22   53
CONECT   22   23   29   29
CONECT   23   24   24   28
CONECT   24   25   54
CONECT   25   26   26   55
CONECT   26   27   56
CONECT   27   28   28
CONECT   28   57
CONECT   30   58
CONECT   31   32   59
CONECT   32   33   37   37
CONECT   33   34   35   36
CONECT   37   60
CONECT   38   39   39   61
END

HMDB0015595
     RDKit          3D
Nilotinib
 61 65  0  0  0  0  0  0  0  0999 V2000
  -10.6962   -0.1290   -0.0962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2286   -0.2457    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1955    0.3711   -0.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0121    0.0166   -0.0397 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6786    0.4166   -0.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5941   -0.2914   -0.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2745    0.0439   -0.4005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1978   -0.7375    0.0662 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9020   -0.7168   -0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5431   -0.0083   -1.4067 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1757   -1.5581    0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938   -2.8144    0.6363 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8876   -3.5979    1.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2028   -3.1313    1.2960 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2719   -3.9674    1.8863 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4711   -1.8645    0.7805 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8082   -1.4227    0.9553 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4126   -0.3401    0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7970    0.3751   -0.6937 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3356    1.4155   -1.3505 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6208    1.7519   -0.9965 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3247    1.0732   -0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6579    1.4814    0.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3076    0.8094    1.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5694    1.1954    1.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1942    2.2377    1.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5637    2.8787    0.1526 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3238    2.5121   -0.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6895    0.0433    0.5680 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4749   -1.1036    0.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1820    1.1709   -1.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2503    1.9224   -1.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0492    3.1285   -2.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8705    4.1163   -1.9740 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7213    3.5206   -2.4705 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4917    2.7892   -3.7329 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5120    1.5304   -1.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2673   -0.8217    0.9856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6279   -0.9744    1.0817 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2427   -0.9391    0.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8886   -0.0322   -1.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0631    0.8243    0.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3283    1.0401   -1.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7545   -1.1587    0.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3998   -1.3887    0.8843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1248   -3.1861    0.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6641   -4.5816    1.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2287   -3.9326    1.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3713   -3.7797    2.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9238   -5.0355    1.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4508   -1.9197    1.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8387    1.9795   -2.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0613    2.5848   -1.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8276   -0.0276    1.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0387    0.6452    2.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2094    2.5166    1.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8765    3.0784   -1.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7053   -0.1022   -0.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1770    1.5129   -1.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4011    2.1013   -1.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5165   -1.2749    1.6126 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 22 29  2  0
 16 30  2  0
  7 31  2  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  1  0
 33 36  1  0
 32 37  2  0
  4 38  1  0
 38 39  2  0
 39  2  1  0
 37  5  1  0
 30 11  1  0
 29 18  1  0
 28 23  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  3 43  1  0
  6 44  1  0
  8 45  1  0
 12 46  1  0
 13 47  1  0
 15 48  1  0
 15 49  1  0
 15 50  1  0
 17 51  1  0
 20 52  1  0
 21 53  1  0
 24 54  1  0
 25 55  1  0
 26 56  1  0
 28 57  1  0
 30 58  1  0
 31 59  1  0
 37 60  1  0
 38 61  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
AMN 107	ChEBI
AMN107	ChEBI
Nilotinibum	ChEBI
AMN-107	HMDB
4-Methyl-N-(3-(4-methylimidazol-1-yl)-5-(trifluoromethyl)phenyl)-3-((4-pyridin-3-ylpyrimidin-2-yl)amino)benzamide	HMDB
Tasigna	HMDB

Chemical Formula

C₂₈H₂₂F₃N₇O

Average Molecular Weight

529.5158

Monoisotopic Molecular Weight

529.183792976

IUPAC Name

4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzamide

Traditional Name

nilotinib

CAS Registry Number

641571-10-0

SMILES

CC1=CN(C=N1)C1=CC(=CC(NC(=O)C2=CC(NC3=NC=CC(=N3)C3=CN=CC=C3)=C(C)C=C2)=C1)C(F)(F)F

InChI Identifier

InChI=1S/C28H22F3N7O/c1-17-5-6-19(10-25(17)37-27-33-9-7-24(36-27)20-4-3-8-32-14-20)26(39)35-22-11-21(28(29,30)31)12-23(13-22)38-15-18(2)34-16-38/h3-16H,1-2H3,(H,35,39)(H,33,36,37)

InChI Key

HHZIURLSWUIHRB-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
1-phenylimidazole
Trifluoromethylbenzene
Aminobenzoic acid or derivatives
P-toluamide
Toluamide
Benzamide
Benzoic acid or derivatives
Benzoyl
Aniline or substituted anilines
Aminopyrimidine
Toluene
N-substituted imidazole
Pyridine
Pyrimidine
Azole
Heteroaromatic compound
Imidazole
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Secondary amine
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Alkyl fluoride
Amine
Organohalogen compound
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organofluoride
Alkyl halide
Organic oxide
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:52172 )
pyrimidines (CHEBI:52172 )
secondary amino compound (CHEBI:52172 )
pyridines (CHEBI:52172 )
carboxamide (CHEBI:52172 )
(trifluoromethyl)benzenes (CHEBI:52172 )

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: HMDB0015595)
Membrane (HMDB: HMDB0015595)

Source

Exogenous

Exogenous (HMDB: HMDB0015595)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Nilotinib Inhibition of BCR-ABL (PathBank: SMP0031697)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.002 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.002 g/L	ALOGPS
logP	4.51	ALOGPS
logP	4.41	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	11.86	ChemAxon
pKa (Strongest Basic)	6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	97.62 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	152.85 m³·mol⁻¹	ChemAxon
Polarizability	52.35 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	224.138	30932474
DeepCCS	[M-H]-	221.742	30932474
DeepCCS	[M-2H]-	254.73	30932474
DeepCCS	[M+Na]+	230.05	30932474
AllCCS	[M+H]+	226.3	32859911
AllCCS	[M+H-H2O]+	224.5	32859911
AllCCS	[M+NH4]+	227.9	32859911
AllCCS	[M+Na]+	228.4	32859911
AllCCS	[M-H]-	209.8	32859911
AllCCS	[M+Na-2H]-	209.9	32859911
AllCCS	[M+HCOO]-	210.1	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.	4.88 minutes	32390414
Predicted by Siyang on May 30, 2022	10.4746 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.21 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	37.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1243.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	124.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	171.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	123.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	79.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	421.2 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	526.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	75.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	786.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	148.7 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	1162.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	251.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	328.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	123.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	78.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	45.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nilotinib	CC1=CN(C=N1)C1=CC(=CC(NC(=O)C2=CC(NC3=NC=CC(=N3)C3=CN=CC=C3)=C(C)C=C2)=C1)C(F)(F)F	5655.1	Standard polar	33892256
Nilotinib	CC1=CN(C=N1)C1=CC(=CC(NC(=O)C2=CC(NC3=NC=CC(=N3)C3=CN=CC=C3)=C(C)C=C2)=C1)C(F)(F)F	4493.3	Standard non polar	33892256
Nilotinib	CC1=CN(C=N1)C1=CC(=CC(NC(=O)C2=CC(NC3=NC=CC(=N3)C3=CN=CC=C3)=C(C)C=C2)=C1)C(F)(F)F	4726.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nilotinib,1TMS,isomer #1	CC1=CN(C2=CC(N(C(=O)C3=CC=C(C)C(NC4=NC=CC(C5=CC=CN=C5)=N4)=C3)[Si](C)(C)C)=CC(C(F)(F)F)=C2)C=N1	4306.4	Semi standard non polar	33892256
Nilotinib,1TMS,isomer #1	CC1=CN(C2=CC(N(C(=O)C3=CC=C(C)C(NC4=NC=CC(C5=CC=CN=C5)=N4)=C3)[Si](C)(C)C)=CC(C(F)(F)F)=C2)C=N1	4390.3	Standard non polar	33892256
Nilotinib,1TMS,isomer #1	CC1=CN(C2=CC(N(C(=O)C3=CC=C(C)C(NC4=NC=CC(C5=CC=CN=C5)=N4)=C3)[Si](C)(C)C)=CC(C(F)(F)F)=C2)C=N1	5516.3	Standard polar	33892256
Nilotinib,1TMS,isomer #2	CC1=CN(C2=CC(NC(=O)C3=CC=C(C)C(N(C4=NC=CC(C5=CC=CN=C5)=N4)[Si](C)(C)C)=C3)=CC(C(F)(F)F)=C2)C=N1	4385.4	Semi standard non polar	33892256
Nilotinib,1TMS,isomer #2	CC1=CN(C2=CC(NC(=O)C3=CC=C(C)C(N(C4=NC=CC(C5=CC=CN=C5)=N4)[Si](C)(C)C)=C3)=CC(C(F)(F)F)=C2)C=N1	4444.6	Standard non polar	33892256
Nilotinib,1TMS,isomer #2	CC1=CN(C2=CC(NC(=O)C3=CC=C(C)C(N(C4=NC=CC(C5=CC=CN=C5)=N4)[Si](C)(C)C)=C3)=CC(C(F)(F)F)=C2)C=N1	5389.2	Standard polar	33892256
Nilotinib,2TMS,isomer #1	CC1=CN(C2=CC(N(C(=O)C3=CC=C(C)C(N(C4=NC=CC(C5=CC=CN=C5)=N4)[Si](C)(C)C)=C3)[Si](C)(C)C)=CC(C(F)(F)F)=C2)C=N1	4172.1	Semi standard non polar	33892256
Nilotinib,2TMS,isomer #1	CC1=CN(C2=CC(N(C(=O)C3=CC=C(C)C(N(C4=NC=CC(C5=CC=CN=C5)=N4)[Si](C)(C)C)=C3)[Si](C)(C)C)=CC(C(F)(F)F)=C2)C=N1	4357.3	Standard non polar	33892256
Nilotinib,2TMS,isomer #1	CC1=CN(C2=CC(N(C(=O)C3=CC=C(C)C(N(C4=NC=CC(C5=CC=CN=C5)=N4)[Si](C)(C)C)=C3)[Si](C)(C)C)=CC(C(F)(F)F)=C2)C=N1	5025.3	Standard polar	33892256
Nilotinib,1TBDMS,isomer #1	CC1=CN(C2=CC(N(C(=O)C3=CC=C(C)C(NC4=NC=CC(C5=CC=CN=C5)=N4)=C3)[Si](C)(C)C(C)(C)C)=CC(C(F)(F)F)=C2)C=N1	4543.9	Semi standard non polar	33892256
Nilotinib,1TBDMS,isomer #1	CC1=CN(C2=CC(N(C(=O)C3=CC=C(C)C(NC4=NC=CC(C5=CC=CN=C5)=N4)=C3)[Si](C)(C)C(C)(C)C)=CC(C(F)(F)F)=C2)C=N1	4573.7	Standard non polar	33892256
Nilotinib,1TBDMS,isomer #1	CC1=CN(C2=CC(N(C(=O)C3=CC=C(C)C(NC4=NC=CC(C5=CC=CN=C5)=N4)=C3)[Si](C)(C)C(C)(C)C)=CC(C(F)(F)F)=C2)C=N1	5542.1	Standard polar	33892256
Nilotinib,1TBDMS,isomer #2	CC1=CN(C2=CC(NC(=O)C3=CC=C(C)C(N(C4=NC=CC(C5=CC=CN=C5)=N4)[Si](C)(C)C(C)(C)C)=C3)=CC(C(F)(F)F)=C2)C=N1	4563.6	Semi standard non polar	33892256
Nilotinib,1TBDMS,isomer #2	CC1=CN(C2=CC(NC(=O)C3=CC=C(C)C(N(C4=NC=CC(C5=CC=CN=C5)=N4)[Si](C)(C)C(C)(C)C)=C3)=CC(C(F)(F)F)=C2)C=N1	4622.1	Standard non polar	33892256
Nilotinib,1TBDMS,isomer #2	CC1=CN(C2=CC(NC(=O)C3=CC=C(C)C(N(C4=NC=CC(C5=CC=CN=C5)=N4)[Si](C)(C)C(C)(C)C)=C3)=CC(C(F)(F)F)=C2)C=N1	5384.0	Standard polar	33892256
Nilotinib,2TBDMS,isomer #1	CC1=CN(C2=CC(N(C(=O)C3=CC=C(C)C(N(C4=NC=CC(C5=CC=CN=C5)=N4)[Si](C)(C)C(C)(C)C)=C3)[Si](C)(C)C(C)(C)C)=CC(C(F)(F)F)=C2)C=N1	4554.6	Semi standard non polar	33892256
Nilotinib,2TBDMS,isomer #1	CC1=CN(C2=CC(N(C(=O)C3=CC=C(C)C(N(C4=NC=CC(C5=CC=CN=C5)=N4)[Si](C)(C)C(C)(C)C)=C3)[Si](C)(C)C(C)(C)C)=CC(C(F)(F)F)=C2)C=N1	4746.7	Standard non polar	33892256
Nilotinib,2TBDMS,isomer #1	CC1=CN(C2=CC(N(C(=O)C3=CC=C(C)C(N(C4=NC=CC(C5=CC=CN=C5)=N4)[Si](C)(C)C(C)(C)C)=C3)[Si](C)(C)C(C)(C)C)=CC(C(F)(F)F)=C2)C=N1	5092.3	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Nilotinib 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 DB04868	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB04868	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB04868

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

559260

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nilotinib

METLIN ID

Not Available

PubChem Compound

644241

PDB ID

NIL

ChEBI ID

52172

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

Maekawa T, Ashihara E, Kimura S: The Bcr-Abl tyrosine kinase inhibitor imatinib and promising new agents against Philadelphia chromosome-positive leukemias. Int J Clin Oncol. 2007 Oct;12(5):327-40. Epub 2007 Oct 22. [PubMed:17929114 ]
Kantarjian HM, Giles F, Gattermann N, Bhalla K, Alimena G, Palandri F, Ossenkoppele GJ, Nicolini FE, O'Brien SG, Litzow M, Bhatia R, Cervantes F, Haque A, Shou Y, Resta DJ, Weitzman A, Hochhaus A, le Coutre P: Nilotinib (formerly AMN107), a highly selective BCR-ABL tyrosine kinase inhibitor, is effective in patients with Philadelphia chromosome-positive chronic myelogenous leukemia in chronic phase following imatinib resistance and intolerance. Blood. 2007 Nov 15;110(10):3540-6. Epub 2007 Aug 22. [PubMed:17715389 ]
Kantarjian H, Giles F, Wunderle L, Bhalla K, O'Brien S, Wassmann B, Tanaka C, Manley P, Rae P, Mietlowski W, Bochinski K, Hochhaus A, Griffin JD, Hoelzer D, Albitar M, Dugan M, Cortes J, Alland L, Ottmann OG: Nilotinib in imatinib-resistant CML and Philadelphia chromosome-positive ALL. N Engl J Med. 2006 Jun 15;354(24):2542-51. [PubMed:16775235 ]
Jabbour E, Cortes J, Giles F, O'Brien S, Kantarijan H: Drug evaluation: Nilotinib - a novel Bcr-Abl tyrosine kinase inhibitor for the treatment of chronic myelocytic leukemia and beyond. IDrugs. 2007 Jul;10(7):468-79. [PubMed:17642017 ]
Breccia M, Cannella L, Nanni M, Stefanizzi C, Alimena G: Nilotinib can override dasatinib resistance in chronic myeloid leukemia patients with secondary resistance to imatinib first-line therapy. Acta Haematol. 2007;118(3):162-4. Epub 2007 Sep 20. [PubMed:17890849 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

References

Haouala A, Widmer N, Duchosal MA, Montemurro M, Buclin T, Decosterd LA: Drug interactions with the tyrosine kinase inhibitors imatinib, dasatinib, and nilotinib. Blood. 2011 Feb 24;117(8):e75-87. doi: 10.1182/blood-2010-07-294330. Epub 2010 Sep 1. [PubMed:20810928 ]

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

Tanaka C, Yin OQ, Smith T, Sethuraman V, Grouss K, Galitz L, Harrell R, Schran H: Effects of rifampin and ketoconazole on the pharmacokinetics of nilotinib in healthy participants. J Clin Pharmacol. 2011 Jan;51(1):75-83. doi: 10.1177/0091270010367428. Epub 2010 Aug 11. [PubMed:20702754 ]
Haouala A, Widmer N, Duchosal MA, Montemurro M, Buclin T, Decosterd LA: Drug interactions with the tyrosine kinase inhibitors imatinib, dasatinib, and nilotinib. Blood. 2011 Feb 24;117(8):e75-87. doi: 10.1182/blood-2010-07-294330. Epub 2010 Sep 1. [PubMed:20810928 ]
Yin OQ, Gallagher N, Tanaka C, Fisher D, Sethuraman V, Zhou W, Lin TH, Heuman D, Schran H: Effects of hepatic impairment on the pharmacokinetics of nilotinib: an open-label, single-dose, parallel-group study. Clin Ther. 2009;31 Pt 2:2459-69. doi: 10.1016/j.clinthera.2009.11.015. [PubMed:20110053 ]
Deremer DL, Ustun C, Natarajan K: Nilotinib: a second-generation tyrosine kinase inhibitor for the treatment of chronic myelogenous leukemia. Clin Ther. 2008 Nov;30(11):1956-75. doi: 10.1016/j.clinthera.2008.11.014. [PubMed:19108785 ]

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

Yin OQ, Gallagher N, Fischer D, Zhao L, Zhou W, Leroy E, Golor G, Schran H: Effects of nilotinib on single-dose warfarin pharmacokinetics and pharmacodynamics: a randomized, single-blind, two-period crossover study in healthy subjects. Clin Drug Investig. 2011;31(3):169-79. doi: 10.2165/11538700-000000000-00000. [PubMed:21184622 ]
Haouala A, Widmer N, Duchosal MA, Montemurro M, Buclin T, Decosterd LA: Drug interactions with the tyrosine kinase inhibitors imatinib, dasatinib, and nilotinib. Blood. 2011 Feb 24;117(8):e75-87. doi: 10.1182/blood-2010-07-294330. Epub 2010 Sep 1. [PubMed:20810928 ]

Enzyme Details

4. 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

Maekawa T, Ashihara E, Kimura S: The Bcr-Abl tyrosine kinase inhibitor imatinib and promising new agents against Philadelphia chromosome-positive leukemias. Int J Clin Oncol. 2007 Oct;12(5):327-40. Epub 2007 Oct 22. [PubMed:17929114 ]
Kantarjian HM, Giles F, Gattermann N, Bhalla K, Alimena G, Palandri F, Ossenkoppele GJ, Nicolini FE, O'Brien SG, Litzow M, Bhatia R, Cervantes F, Haque A, Shou Y, Resta DJ, Weitzman A, Hochhaus A, le Coutre P: Nilotinib (formerly AMN107), a highly selective BCR-ABL tyrosine kinase inhibitor, is effective in patients with Philadelphia chromosome-positive chronic myelogenous leukemia in chronic phase following imatinib resistance and intolerance. Blood. 2007 Nov 15;110(10):3540-6. Epub 2007 Aug 22. [PubMed:17715389 ]
Weisberg E, Manley P, Mestan J, Cowan-Jacob S, Ray A, Griffin JD: AMN107 (nilotinib): a novel and selective inhibitor of BCR-ABL. Br J Cancer. 2006 Jun 19;94(12):1765-9. Epub 2006 May 23. [PubMed:16721371 ]
Swords R, Mahalingam D, Padmanabhan S, Carew J, Giles F: Nilotinib: optimal therapy for patients with chronic myeloid leukemia and resistance or intolerance to imatinib. Drug Des Devel Ther. 2009 Sep 21;3:89-101. [PubMed:19920925 ]
Rosti G, Palandri F, Castagnetti F, Breccia M, Levato L, Gugliotta G, Capucci A, Cedrone M, Fava C, Intermesoli T, Cambrin GR, Stagno F, Tiribelli M, Amabile M, Luatti S, Poerio A, Soverini S, Testoni N, Martinelli G, Alimena G, Pane F, Saglio G, Baccarani M: Nilotinib for the frontline treatment of Ph(+) chronic myeloid leukemia. Blood. 2009 Dec 3;114(24):4933-8. doi: 10.1182/blood-2009-07-232595. Epub 2009 Oct 12. [PubMed:19822896 ]

Enzyme Details

5. Mast/stem cell growth factor receptor

General function:: Involved in protein kinase activity
Specific function:: This is the receptor for stem cell factor (mast cell growth factor). It has a tyrosine-protein kinase activity. Binding of the ligands leads to the autophosphorylation of KIT and its association with substrates such as phosphatidylinositol 3-kinase (Pi3K)
Gene Name:: KIT
Uniprot ID:: P10721
Molecular weight:: 109863.7

References

Guo T, Agaram NP, Wong GC, Hom G, D'Adamo D, Maki RG, Schwartz GK, Veach D, Clarkson BD, Singer S, DeMatteo RP, Besmer P, Antonescu CR: Sorafenib inhibits the imatinib-resistant KITT670I gatekeeper mutation in gastrointestinal stromal tumor. Clin Cancer Res. 2007 Aug 15;13(16):4874-81. [PubMed:17699867 ]

Enzyme Details

6. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Haouala A, Widmer N, Duchosal MA, Montemurro M, Buclin T, Decosterd LA: Drug interactions with the tyrosine kinase inhibitors imatinib, dasatinib, and nilotinib. Blood. 2011 Feb 24;117(8):e75-87. doi: 10.1182/blood-2010-07-294330. Epub 2010 Sep 1. [PubMed:20810928 ]
Deremer DL, Ustun C, Natarajan K: Nilotinib: a second-generation tyrosine kinase inhibitor for the treatment of chronic myelogenous leukemia. Clin Ther. 2008 Nov;30(11):1956-75. doi: 10.1016/j.clinthera.2008.11.014. [PubMed:19108785 ]

Enzyme Details

7. Cytochrome P450 2B6

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. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

References

Haouala A, Widmer N, Duchosal MA, Montemurro M, Buclin T, Decosterd LA: Drug interactions with the tyrosine kinase inhibitors imatinib, dasatinib, and nilotinib. Blood. 2011 Feb 24;117(8):e75-87. doi: 10.1182/blood-2010-07-294330. Epub 2010 Sep 1. [PubMed:20810928 ]

Enzyme Details

8. Cytochrome P450 2C8

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. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

Haouala A, Widmer N, Duchosal MA, Montemurro M, Buclin T, Decosterd LA: Drug interactions with the tyrosine kinase inhibitors imatinib, dasatinib, and nilotinib. Blood. 2011 Feb 24;117(8):e75-87. doi: 10.1182/blood-2010-07-294330. Epub 2010 Sep 1. [PubMed:20810928 ]
Deremer DL, Ustun C, Natarajan K: Nilotinib: a second-generation tyrosine kinase inhibitor for the treatment of chronic myelogenous leukemia. Clin Ther. 2008 Nov;30(11):1956-75. doi: 10.1016/j.clinthera.2008.11.014. [PubMed:19108785 ]

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

Tiwari AK, Sodani K, Wang SR, Kuang YH, Ashby CR Jr, Chen X, Chen ZS: Nilotinib (AMN107, Tasigna) reverses multidrug resistance by inhibiting the activity of the ABCB1/Pgp and ABCG2/BCRP/MXR transporters. Biochem Pharmacol. 2009 Jul 15;78(2):153-61. doi: 10.1016/j.bcp.2009.04.002. Epub 2009 Apr 11. [PubMed:19427995 ]
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 ]
Haouala A, Widmer N, Duchosal MA, Montemurro M, Buclin T, Decosterd LA: Drug interactions with the tyrosine kinase inhibitors imatinib, dasatinib, and nilotinib. Blood. 2011 Feb 24;117(8):e75-87. doi: 10.1182/blood-2010-07-294330. Epub 2010 Sep 1. [PubMed:20810928 ]

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

Tiwari AK, Sodani K, Wang SR, Kuang YH, Ashby CR Jr, Chen X, Chen ZS: Nilotinib (AMN107, Tasigna) reverses multidrug resistance by inhibiting the activity of the ABCB1/Pgp and ABCG2/BCRP/MXR transporters. Biochem Pharmacol. 2009 Jul 15;78(2):153-61. doi: 10.1016/j.bcp.2009.04.002. Epub 2009 Apr 11. [PubMed:19427995 ]
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 ]
Haouala A, Widmer N, Duchosal MA, Montemurro M, Buclin T, Decosterd LA: Drug interactions with the tyrosine kinase inhibitors imatinib, dasatinib, and nilotinib. Blood. 2011 Feb 24;117(8):e75-87. doi: 10.1182/blood-2010-07-294330. Epub 2010 Sep 1. [PubMed:20810928 ]

Showing metabocard for Nilotinib (HMDB0015595)

MOL for HMDB0015595 (Nilotinib)

3D MOL for HMDB0015595 (Nilotinib)

3D SDF for HMDB0015595 (Nilotinib)

3D-SDF for HMDB0015595 (Nilotinib)

PDB for HMDB0015595 (Nilotinib)

3D PDB for HMDB0015595 (Nilotinib)

SMILES for HMDB0015595 (Nilotinib)

INCHI for HMDB0015595 (Nilotinib)

Structure for HMDB0015595 (Nilotinib)

3D Structure for HMDB0015595 (Nilotinib)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

References

References

References

References

References

References

References

References

Transporters

References

References