data_HKI
#

_chem_comp.id                                   HKI
_chem_comp.name                                 "N-(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)butanamide"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C30 H31 Cl N6 O3"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        "Neratinib (HKI-272), bound form"
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2012-12-14
_chem_comp.pdbx_modified_date                   2021-03-13
_chem_comp.pdbx_ambiguous_flag                  N
_chem_comp.pdbx_release_status                  REL
_chem_comp.pdbx_replaced_by                     ?
_chem_comp.pdbx_replaces                        ?
_chem_comp.formula_weight                       559.059
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    HKI
_chem_comp.pdbx_model_coordinates_details       ?
_chem_comp.pdbx_model_coordinates_missing_flag  N
_chem_comp.pdbx_ideal_coordinates_details       Corina
_chem_comp.pdbx_ideal_coordinates_missing_flag  N
_chem_comp.pdbx_model_coordinates_db_code       3W2Q
_chem_comp.pdbx_subcomponent_list               ?
_chem_comp.pdbx_processing_site                 PDBJ
#   #
loop_
_chem_comp_atom.comp_id
_chem_comp_atom.atom_id
_chem_comp_atom.alt_atom_id
_chem_comp_atom.type_symbol
_chem_comp_atom.charge
_chem_comp_atom.pdbx_align
_chem_comp_atom.pdbx_aromatic_flag
_chem_comp_atom.pdbx_leaving_atom_flag
_chem_comp_atom.pdbx_stereo_config
_chem_comp_atom.model_Cartn_x
_chem_comp_atom.model_Cartn_y
_chem_comp_atom.model_Cartn_z
_chem_comp_atom.pdbx_model_Cartn_x_ideal
_chem_comp_atom.pdbx_model_Cartn_y_ideal
_chem_comp_atom.pdbx_model_Cartn_z_ideal
_chem_comp_atom.pdbx_component_atom_id
_chem_comp_atom.pdbx_component_comp_id
_chem_comp_atom.pdbx_ordinal
HKI  CAJ  CAJ  C   0  1  N  N  N   1.654  24.013  52.956  -1.716  -4.729  -1.783  CAJ  HKI   1  
HKI  CAL  CAL  C   0  1  Y  N  N   1.438  32.804  50.984   7.262  -0.657   2.365  CAL  HKI   2  
HKI  CAK  CAK  C   0  1  Y  N  N   0.712  33.151  49.868   8.439  -0.389   1.684  CAK  HKI   3  
HKI  CAO  CAO  C   0  1  Y  N  N  -0.692  25.377  50.586   1.206  -1.496  -2.213  CAO  HKI   4  
HKI  CAP  CAP  C   0  1  Y  N  N  -0.322  26.674  50.279   2.443  -1.303  -1.630  CAP  HKI   5  
HKI  CAN  CAN  C   0  1  Y  N  N   1.518  31.470  51.317   6.098  -0.831   1.630  CAN  HKI   6  
HKI  CAS  CAS  C   0  1  Y  N  N  -0.243  20.239  50.608  -2.813  -0.080  -0.644  CAS  HKI   7  
HKI  CAT  CAT  C   0  1  Y  N  N   1.486  18.601  51.967  -4.954  -1.036   0.889  CAT  HKI   8  
HKI  CAR  CAR  C   0  1  Y  N  N   1.586  24.734  50.460   0.236  -1.843  -0.040  CAR  HKI   9  
HKI  CAM  CAM  C   0  1  Y  N  N   0.101  32.158  49.137   8.414  -0.303   0.304  CAM  HKI  10  
HKI  CAQ  CAQ  C   0  1  Y  N  N   2.414  21.749  53.291  -3.610  -4.142  -0.326  CAQ  HKI  11  
HKI  CBL  CBL  C   0  1  Y  N  N   1.591  22.631  52.634  -2.519  -3.748  -1.116  CBL  HKI  12  
HKI  CBR  CBR  C   0  1  Y  N  N   0.661  20.790  51.497  -3.049  -1.460  -0.563  CBR  HKI  13  
HKI  CBQ  CBQ  C   0  1  Y  N  N   1.536  19.963  52.199  -4.130  -1.948   0.211  CBQ  HKI  14  
HKI  CBI  CBI  C   0  1  Y  N  N   0.256  24.378  50.677   0.098  -1.763  -1.419  CBI  HKI  15  
HKI  CBM  CBM  C   0  1  Y  N  N  -0.289  18.874  50.388  -3.625   0.789   0.029  CBM  HKI  16  
HKI  CBP  CBP  C   0  1  Y  N  N   0.679  22.164  51.710  -2.221  -2.382  -1.244  CBP  HKI  17  
HKI  CBN  CBN  C   0  1  Y  N  N   1.009  26.999  50.081   2.580  -1.377  -0.252  CBN  HKI  18  
HKI  CBO  CBO  C   0  1  Y  N  N   0.589  18.055  51.071  -4.695   0.313   0.803  CBO  HKI  19  
HKI  CBJ  CBJ  C   0  1  Y  N  N   1.985  26.032  50.174   1.473  -1.645   0.543  CBJ  HKI  20  
HKI  CBK  CBK  C   0  1  Y  N  N   0.874  30.542  50.526   6.150  -0.725   0.253  CBK  HKI  21  
HKI  CBH  CBH  C   0  1  N  N  N  -2.591  18.634  49.703  -2.148   2.622  -0.323  CBH  HKI  22  
HKI  CAA  CAA  C   0  1  N  N  N   1.402  14.519  51.149  -7.342   1.782   2.901  CAA  HKI  23  
HKI  CAB  CAB  C   0  1  N  N  N  -7.831  18.607  48.749   1.478   7.484  -1.594  CAB  HKI  24  
HKI  CAC  CAC  C   0  1  N  N  N  -7.717  17.604  46.668   2.085   5.704  -0.069  CAC  HKI  25  
HKI  CAV  CAV  C   0  1  N  N  N   0.962  29.094  50.896   4.892  -0.911  -0.556  CAV  HKI  26  
HKI  CAX  CAX  C   0  1  N  N  N  -3.554  17.670  49.067  -1.904   4.102  -0.470  CAX  HKI  27  
HKI  CBT  CBT  C   0  1  N  N  N  -5.011  18.123  49.196  -0.424   4.347  -0.772  CBT  HKI  28  
HKI  CAY  CAY  C   0  1  N  N  N  -5.726  17.713  47.913  -0.177   5.850  -0.922  CAY  HKI  29  
HKI  CAU  CAU  C   0  1  N  N  N   1.690  16.001  51.281  -6.563   0.647   2.234  CAU  HKI  30  
HKI  NAD  NAD  N   0  1  N  N  N   1.622  25.129  53.300  -1.080  -5.507  -2.312  NAD  HKI  31  
HKI  NBA  NBA  N   0  1  Y  N  N   2.416  20.432  53.093  -4.360  -3.267   0.294  NBA  HKI  32  
HKI  NAZ  NAZ  N   0  1  Y  N  N   0.164  30.856  49.437   7.289  -0.474  -0.362  NAZ  HKI  33  
HKI  NBC  NBC  N   0  1  N  N  N  -0.176  23.061  51.022  -1.156  -1.953  -2.010  NBC  HKI  34  
HKI  NBB  NBB  N   0  1  N  N  N  -1.237  18.341  49.477  -3.388   2.167  -0.053  NBB  HKI  35  
HKI  NBU  NBU  N   0  1  N  N  N  -6.959  18.439  47.595   1.244   6.085  -1.212  NBU  HKI  36  
HKI  OAG  OAG  O   0  1  N  N  N  -3.018  19.579  50.358  -1.229   1.840  -0.447  OAG  HKI  37  
HKI  OBE  OBE  O   0  1  N  N  N   1.397  28.299  49.780   3.797  -1.183   0.322  OBE  HKI  38  
HKI  OBD  OBD  O   0  1  N  N  N   0.523  16.689  50.833  -5.491   1.193   1.464  OBD  HKI  39  
HKI  CLA  CLA  CL  0  0  N  N  N   3.657  26.498  49.921   1.645  -1.737   2.268  CLA  HKI  40  
HKI  H1   H1   H   0  1  N  N  N   1.931  33.556  51.582   7.252  -0.734   3.442  H1   HKI  41  
HKI  H2   H2   H   0  1  N  N  N   0.623  34.185  49.571   9.363  -0.248   2.224  H2   HKI  42  
HKI  H3   H3   H   0  1  N  N  N  -1.733  25.144  50.756   1.100  -1.434  -3.286  H3   HKI  43  
HKI  H4   H4   H   0  1  N  N  N  -1.078  27.440  50.193   3.304  -1.094  -2.247  H4   HKI  44  
HKI  H5   H5   H   0  1  N  N  N   2.077  31.155  52.186   5.164  -1.045   2.127  H5   HKI  45  
HKI  H6   H6   H   0  1  N  N  N  -0.925  20.885  50.076  -1.989   0.295  -1.233  H6   HKI  46  
HKI  H7   H7   H   0  1  N  N  N   2.164  17.950  52.499  -5.782  -1.392   1.483  H7   HKI  47  
HKI  H8   H8   H   0  1  N  N  N   2.341  23.964  50.517  -0.625  -2.050   0.578  H8   HKI  48  
HKI  H9   H9   H   0  1  N  N  N  -0.466  32.449  48.265   9.328  -0.098  -0.234  H9   HKI  49  
HKI  H10  H10  H   0  1  N  N  N   3.106  22.150  54.017  -3.838  -5.194  -0.229  H10  HKI  50  
HKI  H11  H11  H   0  1  N  N  N   2.277  13.944  51.484  -8.160   1.365   3.489  H11  HKI  51  
HKI  H12  H12  H   0  1  N  N  N   0.532  14.258  51.770  -6.676   2.345   3.555  H12  HKI  52  
HKI  H13  H13  H   0  1  N  N  N   1.187  14.280  50.097  -7.746   2.444   2.135  H13  HKI  53  
HKI  H14  H14  H   0  1  N  N  N  -7.328  19.231  49.502   2.538   7.631  -1.804  H14  HKI  54  
HKI  H15  H15  H   0  1  N  N  N  -8.766  19.094  48.434   0.896   7.719  -2.486  H15  HKI  55  
HKI  H16  H16  H   0  1  N  N  N  -8.059  17.622  49.183   1.175   8.140  -0.779  H16  HKI  56  
HKI  H17  H17  H   0  1  N  N  N  -8.656  18.111  46.400   1.943   4.646   0.150  H17  HKI  57  
HKI  H18  H18  H   0  1  N  N  N  -7.121  17.431  45.759   3.132   5.889  -0.310  H18  HKI  58  
HKI  H19  H19  H   0  1  N  N  N  -7.945  16.640  47.146   1.803   6.296   0.803  H19  HKI  59  
HKI  H20  H20  H   0  1  N  N  N  -0.030  28.745  51.220   4.687  -0.003  -1.122  H20  HKI  60  
HKI  H21  H21  H   0  1  N  N  N   1.680  28.977  51.721   5.022  -1.747  -1.243  H21  HKI  61  
HKI  H22  H22  H   0  1  N  N  N  -3.445  16.690  49.554  -2.511   4.490  -1.288  H22  HKI  62  
HKI  H23  H23  H   0  1  N  N  N  -3.307  17.578  47.999  -2.175   4.609   0.456  H23  HKI  63  
HKI  H24  H24  H   0  1  N  N  N  -5.057  19.215  49.320   0.183   3.958   0.045  H24  HKI  64  
HKI  H25  H25  H   0  1  N  N  N  -5.482  17.635  50.062  -0.154   3.840  -1.699  H25  HKI  65  
HKI  H26  H26  H   0  1  N  N  N  -5.978  16.645  47.996  -0.784   6.238  -1.739  H26  HKI  66  
HKI  H27  H27  H   0  1  N  N  N  -5.026  17.860  47.078  -0.447   6.356   0.005  H27  HKI  67  
HKI  H28  H28  H   0  1  N  N  N   2.554  16.276  50.658  -6.160  -0.016   3.000  H28  HKI  68  
HKI  H29  H29  H   0  1  N  N  N   1.899  16.254  52.331  -7.229   0.083   1.581  H29  HKI  69  
HKI  H30  H30  H   0  1  N  N  N  -1.099  22.766  50.774  -1.277  -1.783  -2.957  H30  HKI  70  
HKI  H31  H31  H   0  1  N  N  N  -0.951  17.777  48.702  -4.115   2.794   0.084  H31  HKI  71  
#   #
loop_
_chem_comp_bond.comp_id
_chem_comp_bond.atom_id_1
_chem_comp_bond.atom_id_2
_chem_comp_bond.value_order
_chem_comp_bond.pdbx_aromatic_flag
_chem_comp_bond.pdbx_stereo_config
_chem_comp_bond.pdbx_ordinal
HKI  CAC  NBU  SING  N  N   1  
HKI  NBU  CAY  SING  N  N   2  
HKI  NBU  CAB  SING  N  N   3  
HKI  CAY  CBT  SING  N  N   4  
HKI  CAX  CBT  SING  N  N   5  
HKI  CAX  CBH  SING  N  N   6  
HKI  CAM  NAZ  DOUB  Y  N   7  
HKI  CAM  CAK  SING  Y  N   8  
HKI  NAZ  CBK  SING  Y  N   9  
HKI  NBB  CBH  SING  N  N  10  
HKI  NBB  CBM  SING  N  N  11  
HKI  CBH  OAG  DOUB  N  N  12  
HKI  OBE  CBN  SING  N  N  13  
HKI  OBE  CAV  SING  N  N  14  
HKI  CAK  CAL  DOUB  Y  N  15  
HKI  CLA  CBJ  SING  N  N  16  
HKI  CBN  CBJ  DOUB  Y  N  17  
HKI  CBN  CAP  SING  Y  N  18  
HKI  CBJ  CAR  SING  Y  N  19  
HKI  CAP  CAO  DOUB  Y  N  20  
HKI  CBM  CAS  DOUB  Y  N  21  
HKI  CBM  CBO  SING  Y  N  22  
HKI  CAR  CBI  DOUB  Y  N  23  
HKI  CBK  CAV  SING  N  N  24  
HKI  CBK  CAN  DOUB  Y  N  25  
HKI  CAO  CBI  SING  Y  N  26  
HKI  CAS  CBR  SING  Y  N  27  
HKI  CBI  NBC  SING  N  N  28  
HKI  OBD  CBO  SING  N  N  29  
HKI  OBD  CAU  SING  N  N  30  
HKI  CAL  CAN  SING  Y  N  31  
HKI  NBC  CBP  SING  N  N  32  
HKI  CBO  CAT  DOUB  Y  N  33  
HKI  CAA  CAU  SING  N  N  34  
HKI  CBR  CBP  DOUB  Y  N  35  
HKI  CBR  CBQ  SING  Y  N  36  
HKI  CBP  CBL  SING  Y  N  37  
HKI  CAT  CBQ  SING  Y  N  38  
HKI  CBQ  NBA  DOUB  Y  N  39  
HKI  CBL  CAJ  SING  N  N  40  
HKI  CBL  CAQ  DOUB  Y  N  41  
HKI  CAJ  NAD  TRIP  N  N  42  
HKI  NBA  CAQ  SING  Y  N  43  
HKI  CAL  H1   SING  N  N  44  
HKI  CAK  H2   SING  N  N  45  
HKI  CAO  H3   SING  N  N  46  
HKI  CAP  H4   SING  N  N  47  
HKI  CAN  H5   SING  N  N  48  
HKI  CAS  H6   SING  N  N  49  
HKI  CAT  H7   SING  N  N  50  
HKI  CAR  H8   SING  N  N  51  
HKI  CAM  H9   SING  N  N  52  
HKI  CAQ  H10  SING  N  N  53  
HKI  CAA  H11  SING  N  N  54  
HKI  CAA  H12  SING  N  N  55  
HKI  CAA  H13  SING  N  N  56  
HKI  CAB  H14  SING  N  N  57  
HKI  CAB  H15  SING  N  N  58  
HKI  CAB  H16  SING  N  N  59  
HKI  CAC  H17  SING  N  N  60  
HKI  CAC  H18  SING  N  N  61  
HKI  CAC  H19  SING  N  N  62  
HKI  CAV  H20  SING  N  N  63  
HKI  CAV  H21  SING  N  N  64  
HKI  CAX  H22  SING  N  N  65  
HKI  CAX  H23  SING  N  N  66  
HKI  CBT  H24  SING  N  N  67  
HKI  CBT  H25  SING  N  N  68  
HKI  CAY  H26  SING  N  N  69  
HKI  CAY  H27  SING  N  N  70  
HKI  CAU  H28  SING  N  N  71  
HKI  CAU  H29  SING  N  N  72  
HKI  NBC  H30  SING  N  N  73  
HKI  NBB  H31  SING  N  N  74  
#   #
loop_
_pdbx_chem_comp_descriptor.comp_id
_pdbx_chem_comp_descriptor.type
_pdbx_chem_comp_descriptor.program
_pdbx_chem_comp_descriptor.program_version
_pdbx_chem_comp_descriptor.descriptor
HKI  SMILES            ACDLabs               12.01  "O=C(Nc4cc1c(ncc(C#N)c1Nc3ccc(OCc2ncccc2)c(Cl)c3)cc4OCC)CCCN(C)C"  
HKI  InChI             InChI                 1.03   "InChI=1S/C30H31ClN6O3/c1-4-39-28-16-25-23(15-26(28)36-29(38)9-7-13-37(2)3)30(20(17-32)18-34-25)35-21-10-11-27(24(31)14-21)40-19-22-8-5-6-12-33-22/h5-6,8,10-12,14-16,18H,4,7,9,13,19H2,1-3H3,(H,34,35)(H,36,38)"  
HKI  InChIKey          InChI                 1.03   MIURWHKJMYMLCP-UHFFFAOYSA-N  
HKI  SMILES_CANONICAL  CACTVS                3.370  "CCOc1cc2ncc(C#N)c(Nc3ccc(OCc4ccccn4)c(Cl)c3)c2cc1NC(=O)CCCN(C)C"  
HKI  SMILES            CACTVS                3.370  "CCOc1cc2ncc(C#N)c(Nc3ccc(OCc4ccccn4)c(Cl)c3)c2cc1NC(=O)CCCN(C)C"  
HKI  SMILES_CANONICAL  "OpenEye OEToolkits"  1.7.6  "CCOc1cc2c(cc1NC(=O)CCCN(C)C)c(c(cn2)C#N)Nc3ccc(c(c3)Cl)OCc4ccccn4"  
HKI  SMILES            "OpenEye OEToolkits"  1.7.6  "CCOc1cc2c(cc1NC(=O)CCCN(C)C)c(c(cn2)C#N)Nc3ccc(c(c3)Cl)OCc4ccccn4"  
#   #
loop_
_pdbx_chem_comp_identifier.comp_id
_pdbx_chem_comp_identifier.type
_pdbx_chem_comp_identifier.program
_pdbx_chem_comp_identifier.program_version
_pdbx_chem_comp_identifier.identifier
HKI  "SYSTEMATIC NAME"  ACDLabs               12.01  "N-(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)butanamide"  
HKI  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.7.6  "N-[4-[[3-chloranyl-4-(pyridin-2-ylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-quinolin-6-yl]-4-(dimethylamino)butanamide"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
HKI  "Create component"  2012-12-14  PDBJ  
HKI  "Initial release"   2013-01-11  RCSB  
HKI  "Modify synonyms"   2021-03-13  RCSB  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     HKI
_pdbx_chem_comp_synonyms.name        "Neratinib (HKI-272), bound form"
_pdbx_chem_comp_synonyms.provenance  PDB
_pdbx_chem_comp_synonyms.type        ?
##
