Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6)transporters (2) Show 8 proteins XML

enzymes (6)transporters (2) Show 8 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 02:51:58 UTC

HMDB ID

HMDB0015388

Secondary Accession Numbers

HMDB15388

Metabolite Identification

Common Name

Lapatinib

Description

Lapatinib, also known as GW 572016 or tykerb, belongs to the class of organic compounds known as quinazolinamines. These are heterocyclic aromatic compounds containing a quianazoline moiety substituted by one or more amine groups. Lapatinib is a very strong basic compound (based on its pKa). Pharmaceutical company GlaxoSmithKline (GSK) markets the drug under the propriety names Tykerb (mostly U.S.) and Tyverb (mostly Europe and Russia). It is used for the treatment of patients with advanced or metastatic breast cancer whose tumors overexpress HER2 (ErbB2). Like sorafenib, lapatinib is a protein kinase inhibitor shown to decrease tumor-causing breast cancer stem cells. Phase III study designed to assess lapatinib in combination with chemotherapy for advanced HER2-positive gastric cancer in 2013 failed to meet the primary endpoint of improved overall survival (OS) against chemotherapy alone. Secondary endpoints of the randomized, double-blinded study, were progression-free survival (PFS), response rate and duration of response. The outcome of this study resulted in a somewhat complex and rather specific initial indication for lapatinib—use only in combination with capecitabine for HER2-positive breast cancer in women whose cancer have progressed following previous chemotherapy with anthracycline, taxanes and trastuzumab.

Structure

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

1259
  Mrv0541 02231215212D          

 40 44  0  0  0  0            999 V2000
   10.2164   -1.8725    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4037   -1.9531    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.7743   -3.1512    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.8584    0.6520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1574   -2.2886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.6174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6548   -1.0640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8953   -0.3594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8161    0.6190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8256    3.1512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5732    1.8679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5598   -1.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7393   -1.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7159   -0.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0514    0.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6591    1.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9447    1.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0881    1.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3736    1.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6389    1.1950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1909    1.8081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0881    2.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6591    2.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8256    1.4439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0682   -2.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3736    3.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5257    0.1983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5732    2.7273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5163   -0.6267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2450    0.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9451   -0.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2259   -1.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9547    0.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3740   -0.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0836   -1.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0741   -1.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8029   -0.6763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7837   -2.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5125   -1.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5030   -1.9220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 32  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  2  0  0  0  0
  2 13  1  0  0  0  0
  2 25  1  0  0  0  0
  3 38  1  0  0  0  0
  4 15  1  0  0  0  0
  4 17  1  0  0  0  0
  7 31  1  0  0  0  0
  7 34  1  0  0  0  0
  8 12  1  0  0  0  0
  8 14  1  0  0  0  0
  9 24  1  0  0  0  0
  9 27  1  0  0  0  0
 10 22  1  0  0  0  0
 10 28  2  0  0  0  0
 11 24  2  0  0  0  0
 11 28  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 20  2  0  0  0  0
 16 17  1  0  0  0  0
 16 19  2  0  0  0  0
 16 23  1  0  0  0  0
 17 21  2  0  0  0  0
 18 19  1  0  0  0  0
 18 22  2  0  0  0  0
 18 24  1  0  0  0  0
 20 21  1  0  0  0  0
 22 26  1  0  0  0  0
 23 26  2  0  0  0  0
 27 29  2  0  0  0  0
 27 30  1  0  0  0  0
 29 32  1  0  0  0  0
 30 33  2  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 36 38  1  0  0  0  0
 37 39  2  0  0  0  0
 38 40  2  0  0  0  0
 39 40  1  0  0  0  0
M  END

HMDB0015388
     RDKit          3D
Lapatinib
 66 70  0  0  0  0  0  0  0  0999 V2000
    9.2420    1.6078    1.6781 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4630    1.9828    0.1234 S   0  0  0  0  0  6  0  0  0  0  0  0
    6.9948    2.0130    0.3246 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8852    3.3418   -0.3699 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9514    0.7844   -1.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5373   -0.6199   -0.6610 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1155   -0.6406   -0.5124 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5897   -1.9044   -0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1102   -1.8215    0.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2294   -2.8207    0.3852 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9753   -2.2521    0.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1285   -0.9420   -0.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1333    0.0928   -0.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4733    1.3651   -0.6061 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5357    2.3457   -0.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2111    2.0665   -0.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7430    3.0114   -0.7460 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0483    2.7679   -0.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4357    1.5519   -0.1718 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5675    0.5510    0.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9772   -0.7404    0.3862 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3614   -1.0185    0.6382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2871   -0.0995    1.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6146   -0.4879    1.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0586   -1.7705    1.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3643   -2.1976    1.2034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3448   -1.2682    1.5842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5291   -0.1867    0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0173   -0.3749   -0.6985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1787    0.6121   -1.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8414    1.7867   -1.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3358    1.9557   -0.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9888    3.1079    0.2725 F   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1851    0.9830    0.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0791   -2.6896    0.6378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6061   -4.3548    0.3980 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7752   -2.3387    0.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2059    0.7899   -0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7713   -0.1580   -0.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4114   -0.7600   -0.2081 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0377    0.8457    1.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4852    1.2111    2.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6277    2.5678    2.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4153    0.9846   -2.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0368    0.8292   -1.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8704   -1.3559   -1.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0469   -0.9045    0.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6829   -0.2595   -1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9000   -2.7129   -0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9691   -2.1078    0.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5019   -3.8277    0.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0328   -2.7111    0.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5487    1.5546   -0.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8326    3.3240   -1.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8101    3.5218   -0.6822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2793   -1.5201    0.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0216    0.9534    1.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3273    0.2852    1.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1036   -0.7782    2.5582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3182   -1.7927    1.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4931   -1.3040   -0.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7753    0.4592   -2.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9490    2.5452   -2.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5948    1.1514    1.8953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0357   -3.0828    0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5063   -1.1469    0.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  2  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
 25 35  1  0
 35 36  1  0
 35 37  2  0
 20 38  1  0
 38 39  2  0
 12 40  1  0
 40  9  1  0
 39 13  1  0
 38 16  1  0
 37 22  1  0
 34 28  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  0
  6 47  1  0
  7 48  1  0
  8 49  1  0
  8 50  1  0
 10 51  1  0
 11 52  1  0
 14 53  1  0
 15 54  1  0
 18 55  1  0
 21 56  1  0
 23 57  1  0
 24 58  1  0
 27 59  1  0
 27 60  1  0
 29 61  1  0
 30 62  1  0
 31 63  1  0
 34 64  1  0
 37 65  1  0
 39 66  1  0
M  END

1259
  Mrv0541 02231215212D          

 40 44  0  0  0  0            999 V2000
   10.2164   -1.8725    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4037   -1.9531    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.7743   -3.1512    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.8584    0.6520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1574   -2.2886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.6174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6548   -1.0640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8953   -0.3594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8161    0.6190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8256    3.1512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5732    1.8679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5598   -1.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7393   -1.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7159   -0.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0514    0.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6591    1.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9447    1.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0881    1.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3736    1.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6389    1.1950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1909    1.8081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0881    2.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6591    2.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8256    1.4439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0682   -2.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3736    3.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5257    0.1983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5732    2.7273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5163   -0.6267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2450    0.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9451   -0.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2259   -1.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9547    0.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3740   -0.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0836   -1.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0741   -1.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8029   -0.6763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7837   -2.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5125   -1.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5030   -1.9220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 32  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  2  0  0  0  0
  2 13  1  0  0  0  0
  2 25  1  0  0  0  0
  3 38  1  0  0  0  0
  4 15  1  0  0  0  0
  4 17  1  0  0  0  0
  7 31  1  0  0  0  0
  7 34  1  0  0  0  0
  8 12  1  0  0  0  0
  8 14  1  0  0  0  0
  9 24  1  0  0  0  0
  9 27  1  0  0  0  0
 10 22  1  0  0  0  0
 10 28  2  0  0  0  0
 11 24  2  0  0  0  0
 11 28  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 20  2  0  0  0  0
 16 17  1  0  0  0  0
 16 19  2  0  0  0  0
 16 23  1  0  0  0  0
 17 21  2  0  0  0  0
 18 19  1  0  0  0  0
 18 22  2  0  0  0  0
 18 24  1  0  0  0  0
 20 21  1  0  0  0  0
 22 26  1  0  0  0  0
 23 26  2  0  0  0  0
 27 29  2  0  0  0  0
 27 30  1  0  0  0  0
 29 32  1  0  0  0  0
 30 33  2  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 36 38  1  0  0  0  0
 37 39  2  0  0  0  0
 38 40  2  0  0  0  0
 39 40  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015388

> <DATABASE_NAME>
hmdb

> <SMILES>
CS(=O)(=O)CCNCC1=CC=C(O1)C1=CC2=C(C=C1)N=CN=C2NC1=CC(Cl)=C(OCC2=CC(F)=CC=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H26ClFN4O4S/c1-40(36,37)12-11-32-16-23-7-10-27(39-23)20-5-8-26-24(14-20)29(34-18-33-26)35-22-6-9-28(25(30)15-22)38-17-19-3-2-4-21(31)13-19/h2-10,13-15,18,32H,11-12,16-17H2,1H3,(H,33,34,35)

> <INCHI_KEY>
BCFGMOOMADDAQU-UHFFFAOYSA-N

> <FORMULA>
C29H26ClFN4O4S

> <MOLECULAR_WEIGHT>
581.058

> <EXACT_MASS>
580.134731942

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
61.18680630534976

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-{3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}-6-(5-{[(2-methanesulfonylethyl)amino]methyl}furan-2-yl)quinazolin-4-amine

> <ALOGPS_LOGP>
5.18

> <JCHEM_LOGP>
4.6385087983333335

> <ALOGPS_LOGS>
-4.42

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.986491865570958

> <JCHEM_PKA_STRONGEST_BASIC>
7.203022895921381

> <JCHEM_POLAR_SURFACE_AREA>
106.35000000000001

> <JCHEM_REFRACTIVITY>
152.41719999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.23e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lapatinib

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015388
     RDKit          3D
Lapatinib
 66 70  0  0  0  0  0  0  0  0999 V2000
    9.2420    1.6078    1.6781 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4630    1.9828    0.1234 S   0  0  0  0  0  6  0  0  0  0  0  0
    6.9948    2.0130    0.3246 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8852    3.3418   -0.3699 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9514    0.7844   -1.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5373   -0.6199   -0.6610 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1155   -0.6406   -0.5124 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5897   -1.9044   -0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1102   -1.8215    0.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2294   -2.8207    0.3852 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9753   -2.2521    0.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1285   -0.9420   -0.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1333    0.0928   -0.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4733    1.3651   -0.6061 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5357    2.3457   -0.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2111    2.0665   -0.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7430    3.0114   -0.7460 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0483    2.7679   -0.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4357    1.5519   -0.1718 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5675    0.5510    0.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9772   -0.7404    0.3862 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3614   -1.0185    0.6382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2871   -0.0995    1.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6146   -0.4879    1.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0586   -1.7705    1.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3643   -2.1976    1.2034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3448   -1.2682    1.5842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5291   -0.1867    0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0173   -0.3749   -0.6985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1787    0.6121   -1.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8414    1.7867   -1.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3358    1.9557   -0.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9888    3.1079    0.2725 F   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1851    0.9830    0.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0791   -2.6896    0.6378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6061   -4.3548    0.3980 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7752   -2.3387    0.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2059    0.7899   -0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7713   -0.1580   -0.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4114   -0.7600   -0.2081 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0377    0.8457    1.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4852    1.2111    2.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6277    2.5678    2.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4153    0.9846   -2.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0368    0.8292   -1.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8704   -1.3559   -1.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0469   -0.9045    0.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6829   -0.2595   -1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9000   -2.7129   -0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9691   -2.1078    0.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5019   -3.8277    0.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0328   -2.7111    0.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5487    1.5546   -0.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8326    3.3240   -1.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8101    3.5218   -0.6822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2793   -1.5201    0.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0216    0.9534    1.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3273    0.2852    1.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1036   -0.7782    2.5582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3182   -1.7927    1.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4931   -1.3040   -0.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7753    0.4592   -2.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9490    2.5452   -2.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5948    1.1514    1.8953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0357   -3.0828    0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5063   -1.1469    0.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  2  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
 25 35  1  0
 35 36  1  0
 35 37  2  0
 20 38  1  0
 38 39  2  0
 12 40  1  0
 40  9  1  0
 39 13  1  0
 38 16  1  0
 37 22  1  0
 34 28  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  0
  6 47  1  0
  7 48  1  0
  8 49  1  0
  8 50  1  0
 10 51  1  0
 11 52  1  0
 14 53  1  0
 15 54  1  0
 18 55  1  0
 21 56  1  0
 23 57  1  0
 24 58  1  0
 27 59  1  0
 27 60  1  0
 29 61  1  0
 30 62  1  0
 31 63  1  0
 34 64  1  0
 37 65  1  0
 39 66  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1259                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      19.071  -3.495   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0       4.487  -3.646   0.000  0.00  0.00           S+0
HETATM    3  F   UNK     0      25.712  -5.882   0.000  0.00  0.00           F+0
HETATM    4  O   UNK     0      10.936   1.217   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.894  -4.272   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.080  -3.019   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      21.756  -1.986   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       7.271  -0.671   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      16.457   1.155   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      16.474   5.882   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      17.870   3.487   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       6.645  -2.078   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.113  -2.239   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.803  -0.510   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.429   0.897   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.430   3.519   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.097   2.749   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.098   3.519   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.764   2.749   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.659   2.231   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.690   3.375   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.098   5.059   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.430   5.059   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.474   2.695   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.861  -5.053   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.764   5.829   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.781   0.370   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.870   5.091   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.764  -1.170   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      19.124   1.124   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      20.431  -1.201   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      19.088  -1.955   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      20.449   0.339   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      23.098  -1.232   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      24.423  -2.017   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      24.405  -3.557   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      25.765  -1.262   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      25.730  -4.342   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      27.090  -2.048   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      27.072  -3.588   0.000  0.00  0.00           C+0
CONECT    1   32                                                            
CONECT    2    5    6   13   25                                             
CONECT    3   38                                                            
CONECT    4   15   17                                                       
CONECT    5    2                                                            
CONECT    6    2                                                            
CONECT    7   31   34                                                       
CONECT    8   12   14                                                       
CONECT    9   24   27                                                       
CONECT   10   22   28                                                       
CONECT   11   24   28                                                       
CONECT   12    8   13                                                       
CONECT   13    2   12                                                       
CONECT   14    8   15                                                       
CONECT   15    4   14   20                                                  
CONECT   16   17   19   23                                                  
CONECT   17    4   16   21                                                  
CONECT   18   19   22   24                                                  
CONECT   19   16   18                                                       
CONECT   20   15   21                                                       
CONECT   21   17   20                                                       
CONECT   22   10   18   26                                                  
CONECT   23   16   26                                                       
CONECT   24    9   11   18                                                  
CONECT   25    2                                                            
CONECT   26   22   23                                                       
CONECT   27    9   29   30                                                  
CONECT   28   10   11                                                       
CONECT   29   27   32                                                       
CONECT   30   27   33                                                       
CONECT   31    7   32   33                                                  
CONECT   32    1   29   31                                                  
CONECT   33   30   31                                                       
CONECT   34    7   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35   38                                                       
CONECT   37   35   39                                                       
CONECT   38    3   36   40                                                  
CONECT   39   37   40                                                       
CONECT   40   38   39                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

COMPND    HMDB0015388
HETATM    1  C1  UNL     1       9.242   1.608   1.678  1.00  0.00           C  
HETATM    2  S1  UNL     1       8.463   1.983   0.123  1.00  0.00           S  
HETATM    3  O1  UNL     1       6.995   2.013   0.325  1.00  0.00           O  
HETATM    4  O2  UNL     1       8.885   3.342  -0.370  1.00  0.00           O  
HETATM    5  C2  UNL     1       8.951   0.784  -1.094  1.00  0.00           C  
HETATM    6  C3  UNL     1       8.537  -0.620  -0.661  1.00  0.00           C  
HETATM    7  N1  UNL     1       7.115  -0.641  -0.512  1.00  0.00           N  
HETATM    8  C4  UNL     1       6.590  -1.904  -0.107  1.00  0.00           C  
HETATM    9  C5  UNL     1       5.110  -1.822   0.018  1.00  0.00           C  
HETATM   10  C6  UNL     1       4.229  -2.821   0.385  1.00  0.00           C  
HETATM   11  C7  UNL     1       2.975  -2.252   0.352  1.00  0.00           C  
HETATM   12  C8  UNL     1       3.128  -0.942  -0.029  1.00  0.00           C  
HETATM   13  C9  UNL     1       2.133   0.093  -0.218  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.473   1.365  -0.606  1.00  0.00           C  
HETATM   15  C11 UNL     1       1.536   2.346  -0.787  1.00  0.00           C  
HETATM   16  C12 UNL     1       0.211   2.066  -0.578  1.00  0.00           C  
HETATM   17  N2  UNL     1      -0.743   3.011  -0.746  1.00  0.00           N  
HETATM   18  C13 UNL     1      -2.048   2.768  -0.548  1.00  0.00           C  
HETATM   19  N3  UNL     1      -2.436   1.552  -0.172  1.00  0.00           N  
HETATM   20  C14 UNL     1      -1.568   0.551   0.020  1.00  0.00           C  
HETATM   21  N4  UNL     1      -1.977  -0.740   0.386  1.00  0.00           N  
HETATM   22  C15 UNL     1      -3.361  -1.019   0.638  1.00  0.00           C  
HETATM   23  C16 UNL     1      -4.287  -0.100   1.018  1.00  0.00           C  
HETATM   24  C17 UNL     1      -5.615  -0.488   1.206  1.00  0.00           C  
HETATM   25  C18 UNL     1      -6.059  -1.770   1.027  1.00  0.00           C  
HETATM   26  O3  UNL     1      -7.364  -2.198   1.203  1.00  0.00           O  
HETATM   27  C19 UNL     1      -8.345  -1.268   1.584  1.00  0.00           C  
HETATM   28  C20 UNL     1      -8.529  -0.187   0.585  1.00  0.00           C  
HETATM   29  C21 UNL     1      -8.017  -0.375  -0.699  1.00  0.00           C  
HETATM   30  C22 UNL     1      -8.179   0.612  -1.631  1.00  0.00           C  
HETATM   31  C23 UNL     1      -8.841   1.787  -1.310  1.00  0.00           C  
HETATM   32  C24 UNL     1      -9.336   1.956  -0.051  1.00  0.00           C  
HETATM   33  F1  UNL     1      -9.989   3.108   0.272  1.00  0.00           F  
HETATM   34  C25 UNL     1      -9.185   0.983   0.893  1.00  0.00           C  
HETATM   35  C26 UNL     1      -5.079  -2.690   0.638  1.00  0.00           C  
HETATM   36 CL1  UNL     1      -5.606  -4.355   0.398  1.00  0.00          CL  
HETATM   37  C27 UNL     1      -3.775  -2.339   0.447  1.00  0.00           C  
HETATM   38  C28 UNL     1      -0.206   0.790  -0.182  1.00  0.00           C  
HETATM   39  C29 UNL     1       0.771  -0.158  -0.014  1.00  0.00           C  
HETATM   40  O4  UNL     1       4.411  -0.760  -0.208  1.00  0.00           O  
HETATM   41  H1  UNL     1      10.038   0.846   1.577  1.00  0.00           H  
HETATM   42  H2  UNL     1       8.485   1.211   2.402  1.00  0.00           H  
HETATM   43  H3  UNL     1       9.628   2.568   2.085  1.00  0.00           H  
HETATM   44  H4  UNL     1       8.415   0.985  -2.042  1.00  0.00           H  
HETATM   45  H5  UNL     1      10.037   0.829  -1.301  1.00  0.00           H  
HETATM   46  H6  UNL     1       8.870  -1.356  -1.416  1.00  0.00           H  
HETATM   47  H7  UNL     1       9.047  -0.905   0.288  1.00  0.00           H  
HETATM   48  H8  UNL     1       6.683  -0.259  -1.378  1.00  0.00           H  
HETATM   49  H9  UNL     1       6.900  -2.713  -0.798  1.00  0.00           H  
HETATM   50  H10 UNL     1       6.969  -2.108   0.931  1.00  0.00           H  
HETATM   51  H11 UNL     1       4.502  -3.828   0.639  1.00  0.00           H  
HETATM   52  H12 UNL     1       2.033  -2.711   0.574  1.00  0.00           H  
HETATM   53  H13 UNL     1       3.549   1.555  -0.765  1.00  0.00           H  
HETATM   54  H14 UNL     1       1.833   3.324  -1.088  1.00  0.00           H  
HETATM   55  H15 UNL     1      -2.810   3.522  -0.682  1.00  0.00           H  
HETATM   56  H16 UNL     1      -1.279  -1.520   0.479  1.00  0.00           H  
HETATM   57  H17 UNL     1      -4.022   0.953   1.206  1.00  0.00           H  
HETATM   58  H18 UNL     1      -6.327   0.285   1.520  1.00  0.00           H  
HETATM   59  H19 UNL     1      -8.104  -0.778   2.558  1.00  0.00           H  
HETATM   60  H20 UNL     1      -9.318  -1.793   1.760  1.00  0.00           H  
HETATM   61  H21 UNL     1      -7.493  -1.304  -0.952  1.00  0.00           H  
HETATM   62  H22 UNL     1      -7.775   0.459  -2.637  1.00  0.00           H  
HETATM   63  H23 UNL     1      -8.949   2.545  -2.076  1.00  0.00           H  
HETATM   64  H24 UNL     1      -9.595   1.151   1.895  1.00  0.00           H  
HETATM   65  H25 UNL     1      -3.036  -3.083   0.142  1.00  0.00           H  
HETATM   66  H26 UNL     1       0.506  -1.147   0.290  1.00  0.00           H  
CONECT    1    2   41   42   43
CONECT    2    3    3    4    4
CONECT    2    5
CONECT    5    6   44   45
CONECT    6    7   46   47
CONECT    7    8   48
CONECT    8    9   49   50
CONECT    9   10   10   40
CONECT   10   11   51
CONECT   11   12   12   52
CONECT   12   13   40
CONECT   13   14   14   39
CONECT   14   15   53
CONECT   15   16   16   54
CONECT   16   17   38
CONECT   17   18   18
CONECT   18   19   55
CONECT   19   20   20
CONECT   20   21   38
CONECT   21   22   56
CONECT   22   23   23   37
CONECT   23   24   57
CONECT   24   25   25   58
CONECT   25   26   35
CONECT   26   27
CONECT   27   28   59   60
CONECT   28   29   29   34
CONECT   29   30   61
CONECT   30   31   31   62
CONECT   31   32   63
CONECT   32   33   34   34
CONECT   34   64
CONECT   35   36   37   37
CONECT   37   65
CONECT   38   39   39
CONECT   39   66
END

HMDB0015388
     RDKit          3D
Lapatinib
 66 70  0  0  0  0  0  0  0  0999 V2000
    9.2420    1.6078    1.6781 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4630    1.9828    0.1234 S   0  0  0  0  0  6  0  0  0  0  0  0
    6.9948    2.0130    0.3246 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8852    3.3418   -0.3699 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9514    0.7844   -1.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5373   -0.6199   -0.6610 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1155   -0.6406   -0.5124 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5897   -1.9044   -0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1102   -1.8215    0.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2294   -2.8207    0.3852 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9753   -2.2521    0.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1285   -0.9420   -0.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1333    0.0928   -0.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4733    1.3651   -0.6061 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5357    2.3457   -0.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2111    2.0665   -0.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7430    3.0114   -0.7460 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0483    2.7679   -0.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4357    1.5519   -0.1718 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5675    0.5510    0.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9772   -0.7404    0.3862 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3614   -1.0185    0.6382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2871   -0.0995    1.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6146   -0.4879    1.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0586   -1.7705    1.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3643   -2.1976    1.2034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3448   -1.2682    1.5842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5291   -0.1867    0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0173   -0.3749   -0.6985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1787    0.6121   -1.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8414    1.7867   -1.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3358    1.9557   -0.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9888    3.1079    0.2725 F   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1851    0.9830    0.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0791   -2.6896    0.6378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6061   -4.3548    0.3980 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7752   -2.3387    0.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2059    0.7899   -0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7713   -0.1580   -0.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4114   -0.7600   -0.2081 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0377    0.8457    1.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4852    1.2111    2.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6277    2.5678    2.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4153    0.9846   -2.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0368    0.8292   -1.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8704   -1.3559   -1.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0469   -0.9045    0.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6829   -0.2595   -1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9000   -2.7129   -0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9691   -2.1078    0.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5019   -3.8277    0.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0328   -2.7111    0.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5487    1.5546   -0.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8326    3.3240   -1.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8101    3.5218   -0.6822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2793   -1.5201    0.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0216    0.9534    1.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3273    0.2852    1.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1036   -0.7782    2.5582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3182   -1.7927    1.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4931   -1.3040   -0.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7753    0.4592   -2.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9490    2.5452   -2.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5948    1.1514    1.8953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0357   -3.0828    0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5063   -1.1469    0.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  2  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
 25 35  1  0
 35 36  1  0
 35 37  2  0
 20 38  1  0
 38 39  2  0
 12 40  1  0
 40  9  1  0
 39 13  1  0
 38 16  1  0
 37 22  1  0
 34 28  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  0
  6 47  1  0
  7 48  1  0
  8 49  1  0
  8 50  1  0
 10 51  1  0
 11 52  1  0
 14 53  1  0
 15 54  1  0
 18 55  1  0
 21 56  1  0
 23 57  1  0
 24 58  1  0
 27 59  1  0
 27 60  1  0
 29 61  1  0
 30 62  1  0
 31 63  1  0
 34 64  1  0
 37 65  1  0
 39 66  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
GW 572016	ChEBI
N-(3-Chloro-4-((3-fluorophenyl)methoxy)phenyl)-6-(5-(((2-(methylsulfonyl)ethyl)amino)methyl)-2-furanyl)-4-quinazolinamine	ChEBI
N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6-[5-({[2-(methylsulfonyl)ethyl]amino}methyl)-2-furyl]-4-quinazolinamine	ChEBI
Tykerb	ChEBI
N-(3-Chloro-4-((3-fluorophenyl)methoxy)phenyl)-6-(5-(((2-(methylsulphonyl)ethyl)amino)methyl)-2-furanyl)-4-quinazolinamine	Generator
N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6-[5-({[2-(methylsulphonyl)ethyl]amino}methyl)-2-furyl]-4-quinazolinamine	Generator
FMM	HMDB
GW572016	HMDB
Lapatinib ditosylate	HMDB
Lapatinib tosilate hydrate	HMDB
N-(3-Chloro-4-(((3-fluorobenzyl)oxy)phenyl)-6-(5-(((2-methylsulfonyl)ethyl)amino)methyl) -2-furyl)-4-quinazolinamine	HMDB

Chemical Formula

C₂₉H₂₆ClFN₄O₄S

Average Molecular Weight

581.058

Monoisotopic Molecular Weight

580.134731942

IUPAC Name

N-{3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}-6-(5-{[(2-methanesulfonylethyl)amino]methyl}furan-2-yl)quinazolin-4-amine

Traditional Name

lapatinib

CAS Registry Number

388082-78-8

SMILES

CS(=O)(=O)CCNCC1=CC=C(O1)C1=CC2=C(C=C1)N=CN=C2NC1=CC(Cl)=C(OCC2=CC(F)=CC=C2)C=C1

InChI Identifier

InChI=1S/C29H26ClFN4O4S/c1-40(36,37)12-11-32-16-23-7-10-27(39-23)20-5-8-26-24(14-20)29(34-18-33-26)35-22-6-9-28(25(30)15-22)38-17-19-3-2-4-21(31)13-19/h2-10,13-15,18,32H,11-12,16-17H2,1H3,(H,33,34,35)

InChI Key

BCFGMOOMADDAQU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinazolinamines. These are heterocyclic aromatic compounds containing a quianazoline moiety substituted by one or more amine groups.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Quinazolinamines

Alternative Parents

Substituents

Quinazolinamine
Phenoxy compound
Aniline or substituted anilines
Phenol ether
Aralkylamine
Halobenzene
Fluorobenzene
Chlorobenzene
Aminopyrimidine
Alkyl aryl ether
Imidolactam
Benzenoid
Pyrimidine
Monocyclic benzene moiety
Aryl halide
Aryl fluoride
Aryl chloride
Heteroaromatic compound
Sulfonyl
Sulfone
Furan
Oxacycle
Azacycle
Secondary amine
Ether
Secondary aliphatic amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organofluoride
Organochloride
Organohalogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organofluorine compound (CHEBI:49603 )
organochlorine compound (CHEBI:49603 )
furans (CHEBI:49603 )
quinazolines (CHEBI:49603 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0015388)
Membrane (HMDB: HMDB0015388)

Process

Not Available

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	0.022 g/L	Not Available
LogP	5.4	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.022 g/L	ALOGPS
logP	5.18	ALOGPS
logP	4.64	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	15.99	ChemAxon
pKa (Strongest Basic)	7.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	106.35 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	152.42 m³·mol⁻¹	ChemAxon
Polarizability	61.19 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	216.741	30932474
DeepCCS	[M-H]-	214.345	30932474
DeepCCS	[M-2H]-	247.389	30932474
DeepCCS	[M+Na]+	222.653	30932474
AllCCS	[M+H]+	233.0	32859911
AllCCS	[M+H-H2O]+	231.7	32859911
AllCCS	[M+NH4]+	234.2	32859911
AllCCS	[M+Na]+	234.5	32859911
AllCCS	[M-H]-	205.8	32859911
AllCCS	[M+Na-2H]-	206.4	32859911
AllCCS	[M+HCOO]-	207.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lapatinib	CS(=O)(=O)CCNCC1=CC=C(O1)C1=CC2=C(C=C1)N=CN=C2NC1=CC(Cl)=C(OCC2=CC(F)=CC=C2)C=C1	7155.0	Standard polar	33892256
Lapatinib	CS(=O)(=O)CCNCC1=CC=C(O1)C1=CC2=C(C=C1)N=CN=C2NC1=CC(Cl)=C(OCC2=CC(F)=CC=C2)C=C1	4901.5	Standard non polar	33892256
Lapatinib	CS(=O)(=O)CCNCC1=CC=C(O1)C1=CC2=C(C=C1)N=CN=C2NC1=CC(Cl)=C(OCC2=CC(F)=CC=C2)C=C1	5346.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lapatinib,1TMS,isomer #1	C[Si](C)(C)N(CCS(C)(=O)=O)CC1=CC=C(C2=CC=C3N=CN=C(NC4=CC=C(OCC5=CC=CC(F)=C5)C(Cl)=C4)C3=C2)O1	5016.2	Semi standard non polar	33892256
Lapatinib,1TMS,isomer #1	C[Si](C)(C)N(CCS(C)(=O)=O)CC1=CC=C(C2=CC=C3N=CN=C(NC4=CC=C(OCC5=CC=CC(F)=C5)C(Cl)=C4)C3=C2)O1	4670.3	Standard non polar	33892256
Lapatinib,1TMS,isomer #1	C[Si](C)(C)N(CCS(C)(=O)=O)CC1=CC=C(C2=CC=C3N=CN=C(NC4=CC=C(OCC5=CC=CC(F)=C5)C(Cl)=C4)C3=C2)O1	6791.7	Standard polar	33892256
Lapatinib,1TMS,isomer #2	C[Si](C)(C)N(C1=CC=C(OCC2=CC=CC(F)=C2)C(Cl)=C1)C1=NC=NC2=CC=C(C3=CC=C(CNCCS(C)(=O)=O)O3)C=C12	4749.0	Semi standard non polar	33892256
Lapatinib,1TMS,isomer #2	C[Si](C)(C)N(C1=CC=C(OCC2=CC=CC(F)=C2)C(Cl)=C1)C1=NC=NC2=CC=C(C3=CC=C(CNCCS(C)(=O)=O)O3)C=C12	4594.4	Standard non polar	33892256
Lapatinib,1TMS,isomer #2	C[Si](C)(C)N(C1=CC=C(OCC2=CC=CC(F)=C2)C(Cl)=C1)C1=NC=NC2=CC=C(C3=CC=C(CNCCS(C)(=O)=O)O3)C=C12	6584.8	Standard polar	33892256
Lapatinib,2TMS,isomer #1	C[Si](C)(C)N(CCS(C)(=O)=O)CC1=CC=C(C2=CC=C3N=CN=C(N(C4=CC=C(OCC5=CC=CC(F)=C5)C(Cl)=C4)[Si](C)(C)C)C3=C2)O1	4735.9	Semi standard non polar	33892256
Lapatinib,2TMS,isomer #1	C[Si](C)(C)N(CCS(C)(=O)=O)CC1=CC=C(C2=CC=C3N=CN=C(N(C4=CC=C(OCC5=CC=CC(F)=C5)C(Cl)=C4)[Si](C)(C)C)C3=C2)O1	4809.5	Standard non polar	33892256
Lapatinib,2TMS,isomer #1	C[Si](C)(C)N(CCS(C)(=O)=O)CC1=CC=C(C2=CC=C3N=CN=C(N(C4=CC=C(OCC5=CC=CC(F)=C5)C(Cl)=C4)[Si](C)(C)C)C3=C2)O1	6089.0	Standard polar	33892256
Lapatinib,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCS(C)(=O)=O)CC1=CC=C(C2=CC=C3N=CN=C(NC4=CC=C(OCC5=CC=CC(F)=C5)C(Cl)=C4)C3=C2)O1	5229.2	Semi standard non polar	33892256
Lapatinib,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCS(C)(=O)=O)CC1=CC=C(C2=CC=C3N=CN=C(NC4=CC=C(OCC5=CC=CC(F)=C5)C(Cl)=C4)C3=C2)O1	4929.4	Standard non polar	33892256
Lapatinib,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCS(C)(=O)=O)CC1=CC=C(C2=CC=C3N=CN=C(NC4=CC=C(OCC5=CC=CC(F)=C5)C(Cl)=C4)C3=C2)O1	6707.0	Standard polar	33892256
Lapatinib,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=C(OCC2=CC=CC(F)=C2)C(Cl)=C1)C1=NC=NC2=CC=C(C3=CC=C(CNCCS(C)(=O)=O)O3)C=C12	4989.0	Semi standard non polar	33892256
Lapatinib,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=C(OCC2=CC=CC(F)=C2)C(Cl)=C1)C1=NC=NC2=CC=C(C3=CC=C(CNCCS(C)(=O)=O)O3)C=C12	4827.1	Standard non polar	33892256
Lapatinib,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=C(OCC2=CC=CC(F)=C2)C(Cl)=C1)C1=NC=NC2=CC=C(C3=CC=C(CNCCS(C)(=O)=O)O3)C=C12	6460.6	Standard polar	33892256
Lapatinib,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCS(C)(=O)=O)CC1=CC=C(C2=CC=C3N=CN=C(N(C4=CC=C(OCC5=CC=CC(F)=C5)C(Cl)=C4)[Si](C)(C)C(C)(C)C)C3=C2)O1	5150.7	Semi standard non polar	33892256
Lapatinib,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCS(C)(=O)=O)CC1=CC=C(C2=CC=C3N=CN=C(N(C4=CC=C(OCC5=CC=CC(F)=C5)C(Cl)=C4)[Si](C)(C)C(C)(C)C)C3=C2)O1	5266.3	Standard non polar	33892256
Lapatinib,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCS(C)(=O)=O)CC1=CC=C(C2=CC=C3N=CN=C(N(C4=CC=C(OCC5=CC=CC(F)=C5)C(Cl)=C4)[Si](C)(C)C(C)(C)C)C3=C2)O1	5994.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lapatinib GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pb9-6920550000-7316e856fd5ec8e04f07	2017-09-01	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lapatinib LC-ESI-qTof , Positive-QTOF	splash10-00lr-0009070000-0d55ba750eaa2fb12020	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lapatinib , positive-QTOF	splash10-00lr-0009070000-0d55ba750eaa2fb12020	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lapatinib , positive-QTOF	splash10-0ab9-0649800000-87742edfe3489dab4ac8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lapatinib 30V, Positive-QTOF	splash10-001i-0002090000-49e599088394c442e60b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lapatinib 40V, Positive-QTOF	splash10-014i-0009020000-1e12983abcdd66482af3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lapatinib 10V, Positive-QTOF	splash10-001i-0000090000-f080a7f403cbfd88c590	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lapatinib 20V, Positive-QTOF	splash10-001i-0000090000-e1a1377443b8f411d997	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lapatinib 50V, Positive-QTOF	splash10-014i-0009000000-0b1867dee117396c1949	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lapatinib 10V, Positive-QTOF	splash10-001i-0000090000-d725217276a0f9a7e793	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lapatinib 10V, Positive-QTOF	splash10-001i-0100290000-631c05424fb5cef349db	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lapatinib 20V, Positive-QTOF	splash10-0a5i-1701890000-169201e0014b0f4031fc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lapatinib 40V, Positive-QTOF	splash10-0a4i-6922200000-21ac033aa8e06fb42b19	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lapatinib 10V, Negative-QTOF	splash10-004i-5100190000-854bae0cfc77e5929d1e	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lapatinib 20V, Negative-QTOF	splash10-004i-9100110000-7b6eac51a2b17a8a0213	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lapatinib 40V, Negative-QTOF	splash10-004i-9100000000-16d9d0819f6dca47cd5c	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lapatinib 10V, Positive-QTOF	splash10-001i-0000290000-c15d2a8b4702b6befdbd	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lapatinib 20V, Positive-QTOF	splash10-001i-0001490000-80635a463a3e3328f17b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lapatinib 40V, Positive-QTOF	splash10-0pbj-2119400000-10638e7b757119205a69	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lapatinib 10V, Negative-QTOF	splash10-004i-0000090000-9043926cc3ed698dc68e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lapatinib 20V, Negative-QTOF	splash10-03fr-1109630000-a046bbec44d7c31559d0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lapatinib 40V, Negative-QTOF	splash10-0059-9204010000-e84077eb1512ec5949ba	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01259	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01259	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01259

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

181006

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lapatinib

METLIN ID

Not Available

PubChem Compound

208908

PDB ID

Not Available

ChEBI ID

49603

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

Burris HA 3rd: Dual kinase inhibition in the treatment of breast cancer: initial experience with the EGFR/ErbB-2 inhibitor lapatinib. Oncologist. 2004;9 Suppl 3:10-5. [PubMed:15163842 ]
Johnston SR, Leary A: Lapatinib: a novel EGFR/HER2 tyrosine kinase inhibitor for cancer. Drugs Today (Barc). 2006 Jul;42(7):441-53. [PubMed:16894399 ]
Tevaarwerk AJ, Kolesar JM: Lapatinib: a small-molecule inhibitor of epidermal growth factor receptor and human epidermal growth factor receptor-2 tyrosine kinases used in the treatment of breast cancer. Clin Ther. 2009;31 Pt 2:2332-48. doi: 10.1016/j.clinthera.2009.11.029. [PubMed:20110044 ]
Medina PJ, Goodin S: Lapatinib: a dual inhibitor of human epidermal growth factor receptor tyrosine kinases. Clin Ther. 2008 Aug;30(8):1426-47. doi: 10.1016/j.clinthera.2008.08.008. [PubMed:18803986 ]
Burris HA 3rd, Hurwitz HI, Dees EC, Dowlati A, Blackwell KL, O'Neil B, Marcom PK, Ellis MJ, Overmoyer B, Jones SF, Harris JL, Smith DA, Koch KM, Stead A, Mangum S, Spector NL: Phase I safety, pharmacokinetics, and clinical activity study of lapatinib (GW572016), a reversible dual inhibitor of epidermal growth factor receptor tyrosine kinases, in heavily pretreated patients with metastatic carcinomas. J Clin Oncol. 2005 Aug 10;23(23):5305-13. Epub 2005 Jun 13. [PubMed:15955900 ]
Nelson MH, Dolder CR: Lapatinib: a novel dual tyrosine kinase inhibitor with activity in solid tumors. Ann Pharmacother. 2006 Feb;40(2):261-9. Epub 2006 Jan 17. [PubMed:16418322 ]
Geyer CE, Forster J, Lindquist D, Chan S, Romieu CG, Pienkowski T, Jagiello-Gruszfeld A, Crown J, Chan A, Kaufman B, Skarlos D, Campone M, Davidson N, Berger M, Oliva C, Rubin SD, Stein S, Cameron D: Lapatinib plus capecitabine for HER2-positive advanced breast cancer. N Engl J Med. 2006 Dec 28;355(26):2733-43. [PubMed:17192538 ]

Enzymes

Enzyme Details

1. 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

Medina PJ, Goodin S: Lapatinib: a dual inhibitor of human epidermal growth factor receptor tyrosine kinases. Clin Ther. 2008 Aug;30(8):1426-47. doi: 10.1016/j.clinthera.2008.08.008. [PubMed:18803986 ]
van Erp NP, Gelderblom H, Guchelaar HJ: Clinical pharmacokinetics of tyrosine kinase inhibitors. Cancer Treat Rev. 2009 Dec;35(8):692-706. doi: 10.1016/j.ctrv.2009.08.004. Epub 2009 Sep 5. [PubMed:19733976 ]
Teng WC, Oh JW, New LS, Wahlin MD, Nelson SD, Ho HK, Chan EC: Mechanism-based inactivation of cytochrome P450 3A4 by lapatinib. Mol Pharmacol. 2010 Oct;78(4):693-703. doi: 10.1124/mol.110.065839. Epub 2010 Jul 12. [PubMed:20624855 ]

Enzyme Details

2. Cytochrome P450 2C19

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

References

Medina PJ, Goodin S: Lapatinib: a dual inhibitor of human epidermal growth factor receptor tyrosine kinases. Clin Ther. 2008 Aug;30(8):1426-47. doi: 10.1016/j.clinthera.2008.08.008. [PubMed:18803986 ]
van Erp NP, Gelderblom H, Guchelaar HJ: Clinical pharmacokinetics of tyrosine kinase inhibitors. Cancer Treat Rev. 2009 Dec;35(8):692-706. doi: 10.1016/j.ctrv.2009.08.004. Epub 2009 Sep 5. [PubMed:19733976 ]

Enzyme Details

3. Epidermal growth factor receptor

General function:: Involved in transmembrane receptor protein tyrosine kinase activity
Specific function:: Isoform 2 may act as an antagonist of EGF action
Gene Name:: EGFR
Uniprot ID:: P00533
Molecular weight:: 134276.2

References

Xia W, Mullin RJ, Keith BR, Liu LH, Ma H, Rusnak DW, Owens G, Alligood KJ, Spector NL: Anti-tumor activity of GW572016: a dual tyrosine kinase inhibitor blocks EGF activation of EGFR/erbB2 and downstream Erk1/2 and AKT pathways. Oncogene. 2002 Sep 12;21(41):6255-63. [PubMed:12214266 ]
Grana TM, Sartor CI, Cox AD: Epidermal growth factor receptor autocrine signaling in RIE-1 cells transformed by the Ras oncogene enhances radiation resistance. Cancer Res. 2003 Nov 15;63(22):7807-14. [PubMed:14633707 ]
Xia W, Liu LH, Ho P, Spector NL: Truncated ErbB2 receptor (p95ErbB2) is regulated by heregulin through heterodimer formation with ErbB3 yet remains sensitive to the dual EGFR/ErbB2 kinase inhibitor GW572016. Oncogene. 2004 Jan 22;23(3):646-53. [PubMed:14737100 ]
Zhou H, Kim YS, Peletier A, McCall W, Earp HS, Sartor CI: Effects of the EGFR/HER2 kinase inhibitor GW572016 on EGFR- and HER2-overexpressing breast cancer cell line proliferation, radiosensitization, and resistance. Int J Radiat Oncol Biol Phys. 2004 Feb 1;58(2):344-52. [PubMed:14751502 ]
Langer CJ: Emerging role of epidermal growth factor receptor inhibition in therapy for advanced malignancy: focus on NSCLC. Int J Radiat Oncol Biol Phys. 2004 Mar 1;58(3):991-1002. [PubMed:14967461 ]
Burris HA 3rd: Dual kinase inhibition in the treatment of breast cancer: initial experience with the EGFR/ErbB-2 inhibitor lapatinib. Oncologist. 2004;9 Suppl 3:10-5. [PubMed:15163842 ]
Wood ER, Truesdale AT, McDonald OB, Yuan D, Hassell A, Dickerson SH, Ellis B, Pennisi C, Horne E, Lackey K, Alligood KJ, Rusnak DW, Gilmer TM, Shewchuk L: A unique structure for epidermal growth factor receptor bound to GW572016 (Lapatinib): relationships among protein conformation, inhibitor off-rate, and receptor activity in tumor cells. Cancer Res. 2004 Sep 15;64(18):6652-9. [PubMed:15374980 ]
Vazquez-Martin A, Oliveras-Ferraros C, Cufi S, Del Barco S, Martin-Castillo B, Menendez JA: Lapatinib, a dual HER1/HER2 tyrosine kinase inhibitor, augments basal cleavage of HER2 extracellular domain (ECD) to inhibit HER2-driven cancer cell growth. J Cell Physiol. 2011 Jan;226(1):52-7. doi: 10.1002/jcp.22333. [PubMed:20658522 ]
Johnston SR, Leary A: Lapatinib: a novel EGFR/HER2 tyrosine kinase inhibitor for cancer. Drugs Today (Barc). 2006 Jul;42(7):441-53. [PubMed:16894399 ]
Tevaarwerk AJ, Kolesar JM: Lapatinib: a small-molecule inhibitor of epidermal growth factor receptor and human epidermal growth factor receptor-2 tyrosine kinases used in the treatment of breast cancer. Clin Ther. 2009;31 Pt 2:2332-48. doi: 10.1016/j.clinthera.2009.11.029. [PubMed:20110044 ]
Medina PJ, Goodin S: Lapatinib: a dual inhibitor of human epidermal growth factor receptor tyrosine kinases. Clin Ther. 2008 Aug;30(8):1426-47. doi: 10.1016/j.clinthera.2008.08.008. [PubMed:18803986 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

4. Receptor tyrosine-protein kinase erbB-2

General function:: Involved in transmembrane receptor protein tyrosine kinase activity
Specific function:: Essential component of a neuregulin-receptor complex, although neuregulins do not interact with it alone. GP30 is a potential ligand for this receptor. Binds to the 5'-TCAAATTC-3' sequence in the MT-CO2 promoter and activates its transcription
Gene Name:: ERBB2
Uniprot ID:: P04626
Molecular weight:: 137909.3

References

Xia W, Liu LH, Ho P, Spector NL: Truncated ErbB2 receptor (p95ErbB2) is regulated by heregulin through heterodimer formation with ErbB3 yet remains sensitive to the dual EGFR/ErbB2 kinase inhibitor GW572016. Oncogene. 2004 Jan 22;23(3):646-53. [PubMed:14737100 ]
Zhou H, Kim YS, Peletier A, McCall W, Earp HS, Sartor CI: Effects of the EGFR/HER2 kinase inhibitor GW572016 on EGFR- and HER2-overexpressing breast cancer cell line proliferation, radiosensitization, and resistance. Int J Radiat Oncol Biol Phys. 2004 Feb 1;58(2):344-52. [PubMed:14751502 ]
Langer CJ: Emerging role of epidermal growth factor receptor inhibition in therapy for advanced malignancy: focus on NSCLC. Int J Radiat Oncol Biol Phys. 2004 Mar 1;58(3):991-1002. [PubMed:14967461 ]
Burris HA 3rd: Dual kinase inhibition in the treatment of breast cancer: initial experience with the EGFR/ErbB-2 inhibitor lapatinib. Oncologist. 2004;9 Suppl 3:10-5. [PubMed:15163842 ]
Wood ER, Truesdale AT, McDonald OB, Yuan D, Hassell A, Dickerson SH, Ellis B, Pennisi C, Horne E, Lackey K, Alligood KJ, Rusnak DW, Gilmer TM, Shewchuk L: A unique structure for epidermal growth factor receptor bound to GW572016 (Lapatinib): relationships among protein conformation, inhibitor off-rate, and receptor activity in tumor cells. Cancer Res. 2004 Sep 15;64(18):6652-9. [PubMed:15374980 ]
Grana TM, Sartor CI, Cox AD: Epidermal growth factor receptor autocrine signaling in RIE-1 cells transformed by the Ras oncogene enhances radiation resistance. Cancer Res. 2003 Nov 15;63(22):7807-14. [PubMed:14633707 ]
Xia W, Mullin RJ, Keith BR, Liu LH, Ma H, Rusnak DW, Owens G, Alligood KJ, Spector NL: Anti-tumor activity of GW572016: a dual tyrosine kinase inhibitor blocks EGF activation of EGFR/erbB2 and downstream Erk1/2 and AKT pathways. Oncogene. 2002 Sep 12;21(41):6255-63. [PubMed:12214266 ]
Vazquez-Martin A, Oliveras-Ferraros C, Cufi S, Del Barco S, Martin-Castillo B, Menendez JA: Lapatinib, a dual HER1/HER2 tyrosine kinase inhibitor, augments basal cleavage of HER2 extracellular domain (ECD) to inhibit HER2-driven cancer cell growth. J Cell Physiol. 2011 Jan;226(1):52-7. doi: 10.1002/jcp.22333. [PubMed:20658522 ]
Johnston SR, Leary A: Lapatinib: a novel EGFR/HER2 tyrosine kinase inhibitor for cancer. Drugs Today (Barc). 2006 Jul;42(7):441-53. [PubMed:16894399 ]
Tevaarwerk AJ, Kolesar JM: Lapatinib: a small-molecule inhibitor of epidermal growth factor receptor and human epidermal growth factor receptor-2 tyrosine kinases used in the treatment of breast cancer. Clin Ther. 2009;31 Pt 2:2332-48. doi: 10.1016/j.clinthera.2009.11.029. [PubMed:20110044 ]
Medina PJ, Goodin S: Lapatinib: a dual inhibitor of human epidermal growth factor receptor tyrosine kinases. Clin Ther. 2008 Aug;30(8):1426-47. doi: 10.1016/j.clinthera.2008.08.008. [PubMed:18803986 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

5. Cytochrome P450 3A5

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.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

References

Medina PJ, Goodin S: Lapatinib: a dual inhibitor of human epidermal growth factor receptor tyrosine kinases. Clin Ther. 2008 Aug;30(8):1426-47. doi: 10.1016/j.clinthera.2008.08.008. [PubMed:18803986 ]
van Erp NP, Gelderblom H, Guchelaar HJ: Clinical pharmacokinetics of tyrosine kinase inhibitors. Cancer Treat Rev. 2009 Dec;35(8):692-706. doi: 10.1016/j.ctrv.2009.08.004. Epub 2009 Sep 5. [PubMed:19733976 ]

Enzyme Details

6. 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

Medina PJ, Goodin S: Lapatinib: a dual inhibitor of human epidermal growth factor receptor tyrosine kinases. Clin Ther. 2008 Aug;30(8):1426-47. doi: 10.1016/j.clinthera.2008.08.008. [PubMed:18803986 ]
van Erp NP, Gelderblom H, Guchelaar HJ: Clinical pharmacokinetics of tyrosine kinase inhibitors. Cancer Treat Rev. 2009 Dec;35(8):692-706. doi: 10.1016/j.ctrv.2009.08.004. Epub 2009 Sep 5. [PubMed:19733976 ]

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

Dai CL, Tiwari AK, Wu CP, Su XD, Wang SR, Liu DG, Ashby CR Jr, Huang Y, Robey RW, Liang YJ, Chen LM, Shi CJ, Ambudkar SV, Chen ZS, Fu LW: Lapatinib (Tykerb, GW572016) reverses multidrug resistance in cancer cells by inhibiting the activity of ATP-binding cassette subfamily B member 1 and G member 2. Cancer Res. 2008 Oct 1;68(19):7905-14. doi: 10.1158/0008-5472.CAN-08-0499. [PubMed:18829547 ]

Enzyme Details

2. Antigen peptide transporter 1

General function:: Involved in ATP binding
Specific function:: Involved in the transport of antigens from the cytoplasm to the endoplasmic reticulum for association with MHC class I molecules. Also acts as a molecular scaffold for the final stage of MHC class I folding, namely the binding of peptide. Nascent MHC class I molecules associate with TAP via tapasin. Inhibited by the covalent attachment of herpes simplex virus ICP47 protein, which blocks the peptide-binding site of TAP. Inhibited by human cytomegalovirus US6 glycoprotein, which binds to the lumenal side of the TAP complex and inhibits peptide translocation by specifically blocking ATP-binding to TAP1 and prevents the conformational rearrangement of TAP induced by peptide binding. Inhibited by human adenovirus E3-19K glycoprotein, which binds the TAP complex and acts as a tapasin inhibitor, preventing MHC class I/TAP association. Expression of TAP1 is down-regulated by human Epstein-Barr virus vIL-10 protein, thereby affecting the transport of peptides into the endoplasmic reticulum and subsequent peptide loading by MHC class I molecules
Gene Name:: TAP1
Uniprot ID:: Q03518
Molecular weight:: 87216.9

References

Dai CL, Tiwari AK, Wu CP, Su XD, Wang SR, Liu DG, Ashby CR Jr, Huang Y, Robey RW, Liang YJ, Chen LM, Shi CJ, Ambudkar SV, Chen ZS, Fu LW: Lapatinib (Tykerb, GW572016) reverses multidrug resistance in cancer cells by inhibiting the activity of ATP-binding cassette subfamily B member 1 and G member 2. Cancer Res. 2008 Oct 1;68(19):7905-14. doi: 10.1158/0008-5472.CAN-08-0499. [PubMed:18829547 ]

Showing metabocard for Lapatinib (HMDB0015388)

MOL for HMDB0015388 (Lapatinib)

3D MOL for HMDB0015388 (Lapatinib)

3D SDF for HMDB0015388 (Lapatinib)

3D-SDF for HMDB0015388 (Lapatinib)

PDB for HMDB0015388 (Lapatinib)

3D PDB for HMDB0015388 (Lapatinib)

SMILES for HMDB0015388 (Lapatinib)

INCHI for HMDB0015388 (Lapatinib)

Structure for HMDB0015388 (Lapatinib)

3D Structure for HMDB0015388 (Lapatinib)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

Transporters

References

References