data_A1EKY
# 
_chem_comp.id                                    A1EKY 
_chem_comp.name                                  "3-(4-phenoxyphenyl)-1-piperidin-4-yl-pyrazolo[3,4-d]pyrimidin-4-amine" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H22 N6 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "N-piperidine Ibrutinib" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2025-01-29 
_chem_comp.pdbx_modified_date                    2025-05-02 
_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                        386.450 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     A1EKY 
_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        9LOT 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBC 
_chem_comp.pdbx_pcm                              ? 
# 
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.pdbx_n_terminal_atom_flag 
_chem_comp_atom.pdbx_backbone_atom_flag 
_chem_comp_atom.pdbx_c_terminal_atom_flag 
_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 
A1EKY C5  C1  C 0 1 Y N N N N N -10.490 7.089  -0.180 -3.044 1.213  0.232  C5  A1EKY 1  
A1EKY C7  C2  C 0 1 Y N N N N N -12.525 7.638  -0.858 -3.704 3.381  0.635  C7  A1EKY 2  
A1EKY C1  C3  C 0 1 N N N N N N -7.334  10.119 -1.507 -5.567 -2.685 -1.142 C1  A1EKY 3  
A1EKY C11 C4  C 0 1 Y N N N N N -10.896 5.789  0.162  -1.720 1.665  0.081  C11 A1EKY 4  
A1EKY C12 C5  C 0 1 Y N N N N N -9.710  5.146  0.627  -0.910 0.483  -0.214 C12 A1EKY 5  
A1EKY C13 C6  C 0 1 Y N N N N N -9.461  3.732  1.006  0.553  0.459  -0.453 C13 A1EKY 6  
A1EKY C14 C7  C 0 1 Y N N N N N -8.688  3.418  2.119  1.407  1.198  0.364  C14 A1EKY 7  
A1EKY C15 C8  C 0 1 Y N N N N N -8.389  2.101  2.421  2.767  1.173  0.139  C15 A1EKY 8  
A1EKY C16 C9  C 0 1 Y N N N N N -8.863  1.085  1.608  3.286  0.413  -0.901 C16 A1EKY 9  
A1EKY C18 C10 C 0 1 Y N N N N N -7.589  -0.619 2.740  5.395  -0.374 -0.301 C18 A1EKY 10 
A1EKY C19 C11 C 0 1 Y N N N N N -7.984  -1.270 3.897  6.778  -0.325 -0.401 C19 A1EKY 11 
A1EKY C2  C12 C 0 1 N N N N N N -8.530  9.261  -1.137 -4.381 -1.723 -1.237 C2  A1EKY 12 
A1EKY C20 C13 C 0 1 Y N N N N N -7.021  -1.701 4.793  7.557  -1.100 0.437  C20 A1EKY 13 
A1EKY C21 C14 C 0 1 Y N N N N N -5.680  -1.484 4.536  6.960  -1.923 1.374  C21 A1EKY 14 
A1EKY C22 C15 C 0 1 Y N N N N N -5.297  -0.834 3.382  5.582  -1.973 1.474  C22 A1EKY 15 
A1EKY C23 C16 C 0 1 Y N N N N N -6.246  -0.395 2.474  4.798  -1.201 0.639  C23 A1EKY 16 
A1EKY C24 C17 C 0 1 Y N N N N N -9.636  1.383  0.499  2.438  -0.324 -1.716 C24 A1EKY 17 
A1EKY C25 C18 C 0 1 Y N N N N N -9.932  2.700  0.203  1.077  -0.308 -1.492 C25 A1EKY 18 
A1EKY C27 C19 C 0 1 N N N N N N -7.543  8.743  1.128  -3.985 -2.066 1.203  C27 A1EKY 19 
A1EKY C28 C20 C 0 1 N N N N N N -6.560  9.854  0.813  -5.182 -3.019 1.227  C28 A1EKY 20 
A1EKY C3  C21 C 0 1 N N N N N N -8.116  8.172  -0.163 -4.196 -1.016 0.109  C3  A1EKY 21 
A1EKY C9  C22 C 0 1 Y N N N N N -12.265 5.485  -0.061 -1.458 3.037  0.228  C9  A1EKY 22 
A1EKY N10 N1  N 0 1 N N N N N N -12.820 4.307  0.254  -0.176 3.532  0.089  N10 A1EKY 23 
A1EKY N26 N2  N 0 1 Y N N N N N -8.682  5.984  0.576  -1.717 -0.551 -0.226 N26 A1EKY 24 
A1EKY N29 N3  N 0 1 N N N N N N -6.178  9.809  -0.623 -5.317 -3.670 -0.082 N29 A1EKY 25 
A1EKY N4  N4  N 0 1 Y N N N N N -9.158  7.166  0.077  -3.026 -0.136 0.043  N4  A1EKY 26 
A1EKY N6  N5  N 0 1 Y N N N N N -11.267 8.053  -0.683 -3.996 2.105  0.505  N6  A1EKY 27 
A1EKY N8  N6  N 0 1 Y N N N N N -13.058 6.443  -0.584 -2.475 3.848  0.505  N8  A1EKY 28 
A1EKY O17 O1  O 0 1 N N N N N N -8.567  -0.255 1.823  4.627  0.391  -1.120 O17 A1EKY 29 
A1EKY H1  H1  H 0 1 N N N N N N -13.203 8.367  -1.278 -4.501 4.075  0.855  H1  A1EKY 30 
A1EKY H2  H2  H 0 1 N N N N N N -7.055  9.919  -2.552 -6.473 -2.125 -0.910 H2  A1EKY 31 
A1EKY H3  H3  H 0 1 N N N N N N -7.601  11.180 -1.395 -5.693 -3.201 -2.094 H3  A1EKY 32 
A1EKY H4  H4  H 0 1 N N N N N N -8.318  4.210  2.754  1.004  1.790  1.173  H4  A1EKY 33 
A1EKY H5  H5  H 0 1 N N N N N N -7.788  1.866  3.287  3.429  1.745  0.772  H5  A1EKY 34 
A1EKY H6  H6  H 0 1 N N N N N N -9.032  -1.439 4.098  7.245  0.317  -1.132 H6  A1EKY 35 
A1EKY H7  H7  H 0 1 N N N N N N -9.299  9.893  -0.669 -3.478 -2.281 -1.482 H7  A1EKY 36 
A1EKY H8  H8  H 0 1 N N N N N N -8.940  8.798  -2.047 -4.574 -0.983 -2.013 H8  A1EKY 37 
A1EKY H9  H9  H 0 1 N N N N N N -7.319  -2.210 5.698  8.634  -1.062 0.360  H9  A1EKY 38 
A1EKY H10 H10 H 0 1 N N N N N N -4.933  -1.823 5.239  7.571  -2.528 2.027  H10 A1EKY 39 
A1EKY H11 H11 H 0 1 N N N N N N -4.249  -0.666 3.185  5.117  -2.618 2.207  H11 A1EKY 40 
A1EKY H12 H12 H 0 1 N N N N N N -5.945  0.115  1.571  3.722  -1.241 0.718  H12 A1EKY 41 
A1EKY H13 H13 H 0 1 N N N N N N -10.006 0.589  -0.133 2.845  -0.914 -2.524 H13 A1EKY 42 
A1EKY H14 H14 H 0 1 N N N N N N -10.536 2.930  -0.662 0.418  -0.882 -2.127 H14 A1EKY 43 
A1EKY H15 H15 H 0 1 N N N N N N -8.362  9.145  1.743  -3.895 -1.571 2.170  H15 A1EKY 44 
A1EKY H16 H16 H 0 1 N N N N N N -7.026  7.945  1.681  -3.075 -2.630 0.997  H16 A1EKY 45 
A1EKY H17 H17 H 0 1 N N N N N N -5.660  9.729  1.433  -5.029 -3.776 1.996  H17 A1EKY 46 
A1EKY H18 H18 H 0 1 N N N N N N -7.026  10.825 1.035  -6.090 -2.456 1.448  H18 A1EKY 47 
A1EKY H19 H19 H 0 1 N N N N N N -7.283  7.642  -0.647 -5.083 -0.425 0.336  H19 A1EKY 48 
A1EKY H20 H20 H 0 1 N N N N N N -13.796 4.329  0.037  0.525  2.969  -0.277 H20 A1EKY 49 
A1EKY H21 H21 H 0 1 N N N N N N -12.378 3.579  -0.271 0.024  4.443  0.357  H21 A1EKY 50 
A1EKY H22 H22 H 0 1 N N N N N N -5.840  8.893  -0.840 -6.041 -4.373 -0.063 H22 A1EKY 51 
# 
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 
A1EKY C1  C2  SING N N 1  
A1EKY C1  N29 SING N N 2  
A1EKY C2  C3  SING N N 3  
A1EKY C7  N6  DOUB Y N 4  
A1EKY C7  N8  SING Y N 5  
A1EKY N6  C5  SING Y N 6  
A1EKY N29 C28 SING N N 7  
A1EKY N8  C9  DOUB Y N 8  
A1EKY C5  N4  SING Y N 9  
A1EKY C5  C11 DOUB Y N 10 
A1EKY C3  N4  SING N N 11 
A1EKY C3  C27 SING N N 12 
A1EKY C9  C11 SING Y N 13 
A1EKY C9  N10 SING N N 14 
A1EKY N4  N26 SING Y N 15 
A1EKY C11 C12 SING Y N 16 
A1EKY C25 C24 DOUB Y N 17 
A1EKY C25 C13 SING Y N 18 
A1EKY C24 C16 SING Y N 19 
A1EKY N26 C12 DOUB Y N 20 
A1EKY C12 C13 SING N N 21 
A1EKY C28 C27 SING N N 22 
A1EKY C13 C14 DOUB Y N 23 
A1EKY C16 O17 SING N N 24 
A1EKY C16 C15 DOUB Y N 25 
A1EKY O17 C18 SING N N 26 
A1EKY C14 C15 SING Y N 27 
A1EKY C23 C18 DOUB Y N 28 
A1EKY C23 C22 SING Y N 29 
A1EKY C18 C19 SING Y N 30 
A1EKY C22 C21 DOUB Y N 31 
A1EKY C19 C20 DOUB Y N 32 
A1EKY C21 C20 SING Y N 33 
A1EKY C7  H1  SING N N 34 
A1EKY C1  H2  SING N N 35 
A1EKY C1  H3  SING N N 36 
A1EKY C14 H4  SING N N 37 
A1EKY C15 H5  SING N N 38 
A1EKY C19 H6  SING N N 39 
A1EKY C2  H7  SING N N 40 
A1EKY C2  H8  SING N N 41 
A1EKY C20 H9  SING N N 42 
A1EKY C21 H10 SING N N 43 
A1EKY C22 H11 SING N N 44 
A1EKY C23 H12 SING N N 45 
A1EKY C24 H13 SING N N 46 
A1EKY C25 H14 SING N N 47 
A1EKY C27 H15 SING N N 48 
A1EKY C27 H16 SING N N 49 
A1EKY C28 H17 SING N N 50 
A1EKY C28 H18 SING N N 51 
A1EKY C3  H19 SING N N 52 
A1EKY N10 H20 SING N N 53 
A1EKY N10 H21 SING N N 54 
A1EKY N29 H22 SING N N 55 
# 
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 
A1EKY InChI            InChI                1.06  "InChI=1S/C22H22N6O/c23-21-19-20(15-6-8-18(9-7-15)29-17-4-2-1-3-5-17)27-28(22(19)26-14-25-21)16-10-12-24-13-11-16/h1-9,14,16,24H,10-13H2,(H2,23,25,26)" 
A1EKY InChIKey         InChI                1.06  LGWZZMCTBPCKHR-UHFFFAOYSA-N                                                                                                                             
A1EKY SMILES_CANONICAL CACTVS               3.385 "Nc1ncnc2n(nc(c3ccc(Oc4ccccc4)cc3)c12)C5CCNCC5"                                                                                                         
A1EKY SMILES           CACTVS               3.385 "Nc1ncnc2n(nc(c3ccc(Oc4ccccc4)cc3)c12)C5CCNCC5"                                                                                                         
A1EKY SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "c1ccc(cc1)Oc2ccc(cc2)c3c4c(ncnc4n(n3)C5CCNCC5)N"                                                                                                       
A1EKY SMILES           "OpenEye OEToolkits" 2.0.7 "c1ccc(cc1)Oc2ccc(cc2)c3c4c(ncnc4n(n3)C5CCNCC5)N"                                                                                                       
# 
_pdbx_chem_comp_identifier.comp_id           A1EKY 
_pdbx_chem_comp_identifier.type              "SYSTEMATIC NAME" 
_pdbx_chem_comp_identifier.program           "OpenEye OEToolkits" 
_pdbx_chem_comp_identifier.program_version   2.0.7 
_pdbx_chem_comp_identifier.identifier        "3-(4-phenoxyphenyl)-1-piperidin-4-yl-pyrazolo[3,4-d]pyrimidin-4-amine" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
A1EKY "Create component" 2025-01-29 PDBC 
A1EKY "Initial release"  2025-05-07 RCSB 
# 
_pdbx_chem_comp_synonyms.ordinal      1 
_pdbx_chem_comp_synonyms.comp_id      A1EKY 
_pdbx_chem_comp_synonyms.name         "N-piperidine Ibrutinib" 
_pdbx_chem_comp_synonyms.provenance   PUBCHEM 
_pdbx_chem_comp_synonyms.type         ? 
# 
