data_A1H14
# 
_chem_comp.id                                    A1H14 
_chem_comp.name                                  "Ibrutinib (unbound form)" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C25 H24 N6 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "1-[(3S)-3-[4-azanyl-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2024-01-11 
_chem_comp.pdbx_modified_date                    2024-04-26 
_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                        440.497 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     A1H14 
_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        8RDZ 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBE 
# 
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 
A1H14 N1  N1  N 0 1 Y N N N N N -1.729 -16.615 27.212 -0.890 0.167  -0.713 N1  A1H14 1  
A1H14 N3  N2  N 0 1 Y N N N N N -4.377 -14.815 30.066 -1.096 4.329  1.046  N3  A1H14 2  
A1H14 C4  C1  C 0 1 Y N N N N N 5.699  -13.044 26.146 5.871  -2.780 1.310  C4  A1H14 3  
A1H14 C5  C2  C 0 1 Y N N N N N 4.341  -12.761 26.102 5.324  -1.686 0.669  C5  A1H14 4  
A1H14 C6  C3  C 0 1 Y N N N N N 3.803  -11.958 27.076 6.122  -0.882 -0.132 C6  A1H14 5  
A1H14 C7  C4  C 0 1 Y N N N N N 1.462  -12.615 27.178 4.244  0.389  -0.666 C7  A1H14 6  
A1H14 C8  C5  C 0 1 Y N N N N N 1.709  -13.940 27.480 3.701  0.887  0.511  C8  A1H14 7  
A1H14 C10 C6  C 0 1 Y N N N N N 0.170  -12.171 26.999 3.420  0.096  -1.745 C10 A1H14 8  
A1H14 C13 C7  C 0 1 Y N N N N N -1.796 -15.336 27.495 0.049  1.014  -0.363 C13 A1H14 9  
A1H14 C15 C8  C 0 1 Y N N N N N -3.369 -14.447 29.336 -0.179 3.445  0.665  C15 A1H14 10 
A1H14 C17 C9  C 0 1 Y N N N N N -4.051 -16.118 27.531 -1.998 1.973  0.060  C17 A1H14 11 
A1H14 C20 C10 C 0 1 N N N N N N -2.419 -19.189 25.931 -3.539 -0.260 -2.223 C20 A1H14 12 
A1H14 C21 C11 C 0 1 N N N N N N -2.642 -20.055 24.693 -4.892 -0.916 -2.507 C21 A1H14 13 
A1H14 C22 C12 C 0 1 N N N N N N -4.098 -20.469 24.587 -4.997 -2.223 -1.715 C22 A1H14 14 
A1H14 C24 C13 C 0 1 N N N N N N -5.902 -18.855 22.439 -5.438 -1.924 2.048  C24 A1H14 15 
A1H14 C1  C14 C 0 1 Y N N N N N 4.589  -11.409 28.062 7.469  -1.178 -0.286 C1  A1H14 16 
A1H14 C2  C15 C 0 1 Y N N N N N 5.942  -11.720 28.102 8.011  -2.273 0.358  C2  A1H14 17 
A1H14 C3  C16 C 0 1 Y N N N N N 6.500  -12.532 27.141 7.215  -3.070 1.160  C3  A1H14 18 
A1H14 O1  O1  O 0 1 N N N N N N 2.453  -11.639 27.065 5.585  0.194  -0.765 O1  A1H14 19 
A1H14 C9  C17 C 0 1 Y N N N N N 0.657  -14.837 27.561 2.341  1.091  0.612  C9  A1H14 20 
A1H14 C11 C18 C 0 1 Y N N N N N -0.881 -13.064 27.094 2.060  0.297  -1.650 C11 A1H14 21 
A1H14 C12 C19 C 0 1 Y N N N N N -0.653 -14.405 27.389 1.511  0.797  -0.469 C12 A1H14 22 
A1H14 C14 C20 C 0 1 Y N N N N N -3.177 -14.886 27.910 -0.614 2.213  0.149  C14 A1H14 23 
A1H14 N2  N3  N 0 1 N N N N N N -2.521 -13.470 29.822 1.168  3.731  0.773  N2  A1H14 24 
A1H14 C16 C21 C 0 1 Y N N N N N -5.017 -15.946 29.688 -2.386 4.061  0.943  C16 A1H14 25 
A1H14 N4  N4  N 0 1 Y N N N N N -4.779 -16.719 28.657 -2.839 2.923  0.468  N4  A1H14 26 
A1H14 N5  N5  N 0 1 Y N N N N N -3.027 -16.955 26.896 -2.149 0.724  -0.466 N5  A1H14 27 
A1H14 C18 C22 C 0 1 N N S N N N -3.321 -17.967 25.836 -3.432 0.068  -0.732 C18 A1H14 28 
A1H14 C19 C23 C 0 1 N N N N N N -4.782 -18.426 25.813 -3.521 -1.228 0.080  C19 A1H14 29 
A1H14 N6  N6  N 0 1 N N N N N N -5.024 -19.326 24.678 -4.751 -1.938 -0.295 N6  A1H14 30 
A1H14 C23 C24 C 0 1 N N N N N N -6.104 -19.210 23.874 -5.638 -2.320 0.646  C23 A1H14 31 
A1H14 O2  O2  O 0 1 N N N N N N -7.237 -19.329 24.340 -6.603 -2.991 0.335  O2  A1H14 32 
A1H14 C25 C25 C 0 1 N N N N N N -6.879 -18.388 21.706 -6.252 -2.387 2.992  C25 A1H14 33 
A1H14 H4  H1  H 0 1 N N N N N N 6.134  -13.677 25.387 5.251  -3.406 1.934  H4  A1H14 34 
A1H14 H5  H2  H 0 1 N N N N N N 3.720  -13.165 25.316 4.275  -1.458 0.789  H5  A1H14 35 
A1H14 H6  H3  H 0 1 N N N N N N 2.721  -14.276 27.653 4.345  1.115  1.348  H6  A1H14 36 
A1H14 H8  H4  H 0 1 N N N N N N -0.021 -11.130 26.785 3.846  -0.291 -2.659 H8  A1H14 37 
A1H14 H19 H6  H 0 1 N N N N N N -1.367 -18.871 25.976 -2.738 -0.944 -2.503 H19 A1H14 38 
A1H14 H18 H7  H 0 1 N N N N N N -2.667 -19.764 26.835 -3.452 0.659  -2.803 H18 A1H14 39 
A1H14 H21 H8  H 0 1 N N N N N N -2.363 -19.483 23.796 -5.694 -0.242 -2.204 H21 A1H14 40 
A1H14 H20 H9  H 0 1 N N N N N N -2.014 -20.955 24.764 -4.977 -1.128 -3.572 H20 A1H14 41 
A1H14 H23 H10 H 0 1 N N N N N N -4.252 -20.970 23.620 -5.996 -2.644 -1.836 H23 A1H14 42 
A1H14 H22 H11 H 0 1 N N N N N N -4.324 -21.171 25.403 -4.254 -2.932 -2.080 H22 A1H14 43 
A1H14 H24 H12 H 0 1 N N N N N N -4.926 -18.987 21.995 -4.629 -1.258 2.311  H24 A1H14 44 
A1H14 H1  H13 H 0 1 N N N N N N 4.159  -10.744 28.796 8.091  -0.556 -0.911 H1  A1H14 45 
A1H14 H2  H14 H 0 1 N N N N N N 6.561  -11.322 28.893 9.059  -2.504 0.239  H2  A1H14 46 
A1H14 H3  H15 H 0 1 N N N N N N 7.554  -12.765 27.167 7.641  -3.926 1.662  H3  A1H14 47 
A1H14 H7  H16 H 0 1 N N N N N N 0.856  -15.880 27.759 1.919  1.478  1.528  H7  A1H14 48 
A1H14 H9  H17 H 0 1 N N N N N N -1.892 -12.717 26.937 1.419  0.069  -2.489 H9  A1H14 49 
A1H14 H11 H19 H 0 1 N N N N N N -2.834 -13.175 30.724 1.456  4.607  1.077  H11 A1H14 50 
A1H14 H12 H20 H 0 1 N N N N N N -1.595 -13.839 29.895 1.827  3.057  0.545  H12 A1H14 51 
A1H14 H13 H21 H 0 1 N N N N N N -5.835 -16.253 30.322 -3.097 4.808  1.265  H13 A1H14 52 
A1H14 H15 H22 H 0 1 N N N N N N -3.119 -17.492 24.864 -4.247 0.733  -0.445 H15 A1H14 53 
A1H14 H16 H23 H 0 1 N N N N N N -5.009 -18.956 26.750 -2.656 -1.856 -0.138 H16 A1H14 54 
A1H14 H17 H24 H 0 1 N N N N N N -5.436 -17.546 25.722 -3.545 -0.993 1.144  H17 A1H14 55 
A1H14 H26 H25 H 0 1 N N N N N N -6.705 -18.139 20.670 -6.106 -2.096 4.022  H26 A1H14 56 
A1H14 H25 H26 H 0 1 N N N N N N -7.860 -18.251 22.137 -7.061 -3.053 2.729  H25 A1H14 57 
# 
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 
A1H14 C1  C2  DOUB Y N 1  
A1H14 C1  C6  SING Y N 2  
A1H14 C2  C3  SING Y N 3  
A1H14 C3  C4  DOUB Y N 4  
A1H14 C4  C5  SING Y N 5  
A1H14 C5  C6  DOUB Y N 6  
A1H14 C6  O1  SING N N 7  
A1H14 O1  C7  SING N N 8  
A1H14 C7  C8  DOUB Y N 9  
A1H14 C7  C10 SING Y N 10 
A1H14 C8  C9  SING Y N 11 
A1H14 C9  C12 DOUB Y N 12 
A1H14 C10 C11 DOUB Y N 13 
A1H14 C11 C12 SING Y N 14 
A1H14 C12 C13 SING N N 15 
A1H14 C13 N1  DOUB Y N 16 
A1H14 C13 C14 SING Y N 17 
A1H14 N1  N5  SING Y N 18 
A1H14 C14 C15 SING Y N 19 
A1H14 C14 C17 DOUB Y N 20 
A1H14 C15 N2  SING N N 21 
A1H14 C15 N3  DOUB Y N 22 
A1H14 N3  C16 SING Y N 23 
A1H14 C16 N4  DOUB Y N 24 
A1H14 N4  C17 SING Y N 25 
A1H14 C17 N5  SING Y N 26 
A1H14 N5  C18 SING N N 27 
A1H14 C18 C19 SING N N 28 
A1H14 C18 C20 SING N N 29 
A1H14 C19 N6  SING N N 30 
A1H14 C20 C21 SING N N 31 
A1H14 C21 C22 SING N N 32 
A1H14 C22 N6  SING N N 33 
A1H14 N6  C23 SING N N 34 
A1H14 C23 O2  DOUB N N 35 
A1H14 C23 C24 SING N N 36 
A1H14 C24 C25 DOUB N N 37 
A1H14 C4  H4  SING N N 38 
A1H14 C5  H5  SING N N 39 
A1H14 C8  H6  SING N N 40 
A1H14 C10 H8  SING N N 41 
A1H14 C20 H19 SING N N 42 
A1H14 C20 H18 SING N N 43 
A1H14 C21 H21 SING N N 44 
A1H14 C21 H20 SING N N 45 
A1H14 C22 H23 SING N N 46 
A1H14 C22 H22 SING N N 47 
A1H14 C24 H24 SING N N 48 
A1H14 C1  H1  SING N N 49 
A1H14 C2  H2  SING N N 50 
A1H14 C3  H3  SING N N 51 
A1H14 C9  H7  SING N N 52 
A1H14 C11 H9  SING N N 53 
A1H14 N2  H11 SING N N 54 
A1H14 N2  H12 SING N N 55 
A1H14 C16 H13 SING N N 56 
A1H14 C18 H15 SING N N 57 
A1H14 C19 H16 SING N N 58 
A1H14 C19 H17 SING N N 59 
A1H14 C25 H26 SING N N 60 
A1H14 C25 H25 SING N N 61 
# 
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 
A1H14 InChI            InChI                1.06  "InChI=1S/C25H24N6O2/c1-2-21(32)30-14-6-7-18(15-30)31-25-22(24(26)27-16-28-25)23(29-31)17-10-12-20(13-11-17)33-19-8-4-3-5-9-19/h2-5,8-13,16,18H,1,6-7,14-15H2,(H2,26,27,28)/t18-/m0/s1" 
A1H14 InChIKey         InChI                1.06  XYFPWWZEPKGCCK-SFHVURJKSA-N                                                                                                                                                             
A1H14 SMILES_CANONICAL CACTVS               3.385 "Nc1ncnc2n(nc(c3ccc(Oc4ccccc4)cc3)c12)[C@H]5CCCN(C5)C(=O)C=C"                                                                                                                           
A1H14 SMILES           CACTVS               3.385 "Nc1ncnc2n(nc(c3ccc(Oc4ccccc4)cc3)c12)[CH]5CCCN(C5)C(=O)C=C"                                                                                                                            
A1H14 SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "C=CC(=O)N1CCC[C@@H](C1)n2c3c(c(n2)c4ccc(cc4)Oc5ccccc5)c(ncn3)N"                                                                                                                        
A1H14 SMILES           "OpenEye OEToolkits" 2.0.7 "C=CC(=O)N1CCCC(C1)n2c3c(c(n2)c4ccc(cc4)Oc5ccccc5)c(ncn3)N"                                                                                                                             
# 
_pdbx_chem_comp_identifier.comp_id           A1H14 
_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        "1-[(3~{S})-3-[4-azanyl-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
A1H14 "Create component" 2024-01-11 PDBE 
A1H14 "Initial release"  2024-05-01 RCSB 
# 
_pdbx_chem_comp_synonyms.ordinal      1 
_pdbx_chem_comp_synonyms.comp_id      A1H14 
_pdbx_chem_comp_synonyms.name         "1-[(3S)-3-[4-azanyl-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one" 
_pdbx_chem_comp_synonyms.provenance   PDB 
_pdbx_chem_comp_synonyms.type         ? 
# 
