data_A1EK0
# 
_chem_comp.id                                    A1EK0 
_chem_comp.name                                  Tirabrutinib 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C25 H22 N6 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "Btk Kinase inhibitor" 
_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                        454.481 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     A1EK0 
_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        9LPD 
_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 
A1EK0 N1  N1  N 0 1 Y N N N N N 17.513 6.040  -0.596 0.031  4.967  -0.422 N1  A1EK0 1  
A1EK0 C2  C1  C 0 1 Y N N N N N 17.939 7.258  -0.947 1.330  4.980  -0.649 C2  A1EK0 2  
A1EK0 N3  N2  N 0 1 Y N N N N N 19.159 7.785  -0.813 2.059  3.882  -0.630 N3  A1EK0 3  
A1EK0 C4  C2  C 0 1 Y N N N N N 20.029 6.922  -0.271 1.500  2.703  -0.377 C4  A1EK0 4  
A1EK0 C7  C3  C 0 1 N N N N N N 23.223 8.106  -1.472 3.498  -0.007 -1.650 C7  A1EK0 5  
A1EK0 C8  C4  C 0 1 N N N N N N 24.021 9.404  -1.410 4.775  -0.789 -1.257 C8  A1EK0 6  
A1EK0 C10 C5  C 0 1 N N N N N N 24.667 10.821 0.608  5.314  -1.859 0.951  C10 A1EK0 7  
A1EK0 C12 C6  C 0 1 N N N N N N 24.155 11.332 1.861  6.106  -2.866 0.312  C12 A1EK0 8  
A1EK0 C13 C7  C 0 1 N N N N N N 23.627 11.721 2.852  6.755  -3.693 -0.211 C13 A1EK0 9  
A1EK0 C14 C8  C 0 1 N N N N N N 23.060 12.102 4.143  7.569  -4.729 -0.867 C14 A1EK0 10 
A1EK0 C15 C9  C 0 1 N N N N N N 22.934 8.972  0.709  3.870  0.180  0.735  C15 A1EK0 11 
A1EK0 C16 C10 C 0 1 N N N N N N 21.946 5.983  0.494  0.952  0.588  -0.002 C16 A1EK0 12 
A1EK0 C19 C11 C 0 1 Y N N N N N 21.157 3.650  0.899  -1.458 0.795  0.390  C19 A1EK0 13 
A1EK0 C20 C12 C 0 1 Y N N N N N 21.681 3.296  2.138  -2.103 -0.022 -0.528 C20 A1EK0 14 
A1EK0 C21 C13 C 0 1 Y N N N N N 21.988 1.971  2.411  -3.355 -0.529 -0.240 C21 A1EK0 15 
A1EK0 C22 C14 C 0 1 Y N N N N N 21.770 0.995  1.442  -3.968 -0.221 0.966  C22 A1EK0 16 
A1EK0 C24 C15 C 0 1 Y N N N N N 23.009 -0.732 2.606  -5.743 -1.612 0.379  C24 A1EK0 17 
A1EK0 C25 C16 C 0 1 Y N N N N N 24.356 -0.495 2.365  -5.297 -2.926 0.363  C25 A1EK0 18 
A1EK0 C26 C17 C 0 1 Y N N N N N 25.293 -0.870 3.314  -5.854 -3.833 -0.518 C26 A1EK0 19 
A1EK0 C27 C18 C 0 1 Y N N N N N 24.894 -1.474 4.491  -6.854 -3.431 -1.385 C27 A1EK0 20 
A1EK0 C28 C19 C 0 1 Y N N N N N 23.548 -1.707 4.724  -7.299 -2.123 -1.372 C28 A1EK0 21 
A1EK0 C29 C20 C 0 1 Y N N N N N 22.597 -1.338 3.786  -6.746 -1.212 -0.492 C29 A1EK0 22 
A1EK0 C30 C21 C 0 1 Y N N N N N 21.244 1.344  0.206  -3.324 0.597  1.883  C30 A1EK0 23 
A1EK0 C31 C22 C 0 1 Y N N N N N 20.938 2.668  -0.064 -2.072 1.103  1.597  C31 A1EK0 24 
A1EK0 C32 C23 C 0 1 Y N N N N N 19.735 5.591  0.130  0.128  2.644  -0.131 C32 A1EK0 25 
A1EK0 C33 C24 C 0 1 Y N N N N N 18.395 5.177  -0.052 -0.607 3.828  -0.160 C33 A1EK0 26 
A1EK0 C6  C25 C 0 1 N N R N N N 22.138 8.339  -0.421 3.374  0.999  -0.476 C6  A1EK0 27 
A1EK0 N18 N3  N 0 1 N N N N N N 20.927 5.030  0.577  -0.184 1.306  0.101  N18 A1EK0 28 
A1EK0 N34 N4  N 0 1 N N N N N N 17.950 3.963  0.257  -1.974 3.820  0.078  N34 A1EK0 29 
A1EK0 N5  N5  N 0 1 N N N N N N 21.379 7.128  -0.041 1.980  1.409  -0.289 N5  A1EK0 30 
A1EK0 N9  N6  N 0 1 N N N N N N 23.923 9.792  0.001  4.707  -0.909 0.211  N9  A1EK0 31 
A1EK0 O11 O1  O 0 1 N N N N N N 25.698 11.270 0.116  5.188  -1.860 2.161  O11 A1EK0 32 
A1EK0 O17 O2  O 0 1 N N N N N N 23.099 5.819  0.855  1.036  -0.617 0.144  O17 A1EK0 33 
A1EK0 O23 O3  O 0 1 N N N N N N 22.074 -0.355 1.638  -5.201 -0.720 1.248  O23 A1EK0 34 
A1EK0 H1  H1  H 0 1 N N N N N N 17.198 7.901  -1.399 1.814  5.923  -0.857 H1  A1EK0 35 
A1EK0 H2  H2  H 0 1 N N N N N N 22.785 7.955  -2.470 3.635  0.514  -2.598 H2  A1EK0 36 
A1EK0 H3  H3  H 0 1 N N N N N N 23.850 7.240  -1.212 2.632  -0.668 -1.691 H3  A1EK0 37 
A1EK0 H4  H4  H 0 1 N N N N N N 25.069 9.237  -1.701 4.773  -1.777 -1.718 H4  A1EK0 38 
A1EK0 H5  H5  H 0 1 N N N N N N 23.577 10.171 -2.062 5.666  -0.234 -1.551 H5  A1EK0 39 
A1EK0 H6  H6  H 0 1 N N N N N N 22.317 12.899 3.997  7.975  -5.403 -0.114 H6  A1EK0 40 
A1EK0 H7  H7  H 0 1 N N N N N N 22.575 11.228 4.602  6.947  -5.293 -1.562 H7  A1EK0 41 
A1EK0 H8  H8  H 0 1 N N N N N N 23.862 12.465 4.803  8.387  -4.258 -1.412 H8  A1EK0 42 
A1EK0 H9  H9  H 0 1 N N N N N N 22.289 9.594  1.346  4.459  0.816  1.396  H9  A1EK0 43 
A1EK0 H10 H10 H 0 1 N N N N N N 23.426 8.204  1.324  3.019  -0.232 1.277  H10 A1EK0 44 
A1EK0 H11 H11 H 0 1 N N N N N N 21.849 4.054  2.889  -1.626 -0.262 -1.467 H11 A1EK0 45 
A1EK0 H12 H12 H 0 1 N N N N N N 22.395 1.697  3.373  -3.857 -1.165 -0.954 H12 A1EK0 46 
A1EK0 H13 H13 H 0 1 N N N N N N 24.670 -0.023 1.446  -4.516 -3.240 1.039  H13 A1EK0 47 
A1EK0 H14 H14 H 0 1 N N N N N N 26.342 -0.689 3.133  -5.507 -4.856 -0.531 H14 A1EK0 48 
A1EK0 H15 H15 H 0 1 N N N N N N 25.629 -1.764 5.227  -7.287 -4.142 -2.073 H15 A1EK0 49 
A1EK0 H16 H16 H 0 1 N N N N N N 23.238 -2.180 5.644  -8.081 -1.812 -2.049 H16 A1EK0 50 
A1EK0 H17 H17 H 0 1 N N N N N N 21.548 -1.519 3.970  -7.095 -0.190 -0.482 H17 A1EK0 51 
A1EK0 H18 H18 H 0 1 N N N N N N 21.074 0.585  -0.544 -3.802 0.837  2.821  H18 A1EK0 52 
A1EK0 H19 H19 H 0 1 N N N N N N 20.528 2.940  -1.025 -1.570 1.739  2.311  H19 A1EK0 53 
A1EK0 H20 H20 H 0 1 N N N N N N 21.436 9.090  -0.812 4.011  1.868  -0.644 H20 A1EK0 54 
A1EK0 H21 H21 H 0 1 N N N N N N 16.981 3.892  0.020  -2.461 4.657  0.138  H21 A1EK0 55 
A1EK0 H22 H22 H 0 1 N N N N N N 18.469 3.278  -0.254 -2.443 2.977  0.184  H22 A1EK0 56 
# 
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 
A1EK0 C7  C8  SING N N 1  
A1EK0 C7  C6  SING N N 2  
A1EK0 C8  N9  SING N N 3  
A1EK0 C2  N3  DOUB Y N 4  
A1EK0 C2  N1  SING Y N 5  
A1EK0 N3  C4  SING Y N 6  
A1EK0 N1  C33 DOUB Y N 7  
A1EK0 C6  N5  SING N N 8  
A1EK0 C6  C15 SING N N 9  
A1EK0 C4  N5  SING N N 10 
A1EK0 C4  C32 DOUB Y N 11 
A1EK0 C31 C30 DOUB Y N 12 
A1EK0 C31 C19 SING Y N 13 
A1EK0 C33 C32 SING Y N 14 
A1EK0 C33 N34 SING N N 15 
A1EK0 N5  C16 SING N N 16 
A1EK0 N9  C10 SING N N 17 
A1EK0 N9  C15 SING N N 18 
A1EK0 O11 C10 DOUB N N 19 
A1EK0 C32 N18 SING N N 20 
A1EK0 C30 C22 SING Y N 21 
A1EK0 C16 N18 SING N N 22 
A1EK0 C16 O17 DOUB N N 23 
A1EK0 N18 C19 SING N N 24 
A1EK0 C10 C12 SING N N 25 
A1EK0 C19 C20 DOUB Y N 26 
A1EK0 C22 O23 SING N N 27 
A1EK0 C22 C21 DOUB Y N 28 
A1EK0 O23 C24 SING N N 29 
A1EK0 C12 C13 TRIP N N 30 
A1EK0 C20 C21 SING Y N 31 
A1EK0 C25 C24 DOUB Y N 32 
A1EK0 C25 C26 SING Y N 33 
A1EK0 C24 C29 SING Y N 34 
A1EK0 C13 C14 SING N N 35 
A1EK0 C26 C27 DOUB Y N 36 
A1EK0 C29 C28 DOUB Y N 37 
A1EK0 C27 C28 SING Y N 38 
A1EK0 C2  H1  SING N N 39 
A1EK0 C7  H2  SING N N 40 
A1EK0 C7  H3  SING N N 41 
A1EK0 C8  H4  SING N N 42 
A1EK0 C8  H5  SING N N 43 
A1EK0 C14 H6  SING N N 44 
A1EK0 C14 H7  SING N N 45 
A1EK0 C14 H8  SING N N 46 
A1EK0 C15 H9  SING N N 47 
A1EK0 C15 H10 SING N N 48 
A1EK0 C20 H11 SING N N 49 
A1EK0 C21 H12 SING N N 50 
A1EK0 C25 H13 SING N N 51 
A1EK0 C26 H14 SING N N 52 
A1EK0 C27 H15 SING N N 53 
A1EK0 C28 H16 SING N N 54 
A1EK0 C29 H17 SING N N 55 
A1EK0 C30 H18 SING N N 56 
A1EK0 C31 H19 SING N N 57 
A1EK0 C6  H20 SING N N 58 
A1EK0 N34 H21 SING N N 59 
A1EK0 N34 H22 SING N N 60 
# 
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 
A1EK0 InChI            InChI                1.06  "InChI=1S/C25H22N6O3/c1-2-6-21(32)29-14-13-18(15-29)31-24-22(23(26)27-16-28-24)30(25(31)33)17-9-11-20(12-10-17)34-19-7-4-3-5-8-19/h3-5,7-12,16,18H,13-15H2,1H3,(H2,26,27,28)/t18-/m1/s1" 
A1EK0 InChIKey         InChI                1.06  SEJLPXCPMNSRAM-GOSISDBHSA-N                                                                                                                                                              
A1EK0 SMILES_CANONICAL CACTVS               3.385 "CC#CC(=O)N1CC[C@H](C1)N2C(=O)N(c3ccc(Oc4ccccc4)cc3)c5c(N)ncnc25"                                                                                                                        
A1EK0 SMILES           CACTVS               3.385 "CC#CC(=O)N1CC[CH](C1)N2C(=O)N(c3ccc(Oc4ccccc4)cc3)c5c(N)ncnc25"                                                                                                                         
A1EK0 SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "CC#CC(=O)N1CC[C@H](C1)N2c3c(c(ncn3)N)N(C2=O)c4ccc(cc4)Oc5ccccc5"                                                                                                                        
A1EK0 SMILES           "OpenEye OEToolkits" 2.0.7 "CC#CC(=O)N1CCC(C1)N2c3c(c(ncn3)N)N(C2=O)c4ccc(cc4)Oc5ccccc5"                                                                                                                            
# 
_pdbx_chem_comp_identifier.comp_id           A1EK0 
_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        "6-azanyl-9-[(3~{R})-1-but-2-ynoylpyrrolidin-3-yl]-7-(4-phenoxyphenyl)purin-8-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 
A1EK0 "Create component" 2025-01-29 PDBC 
A1EK0 "Initial release"  2025-05-07 RCSB 
# 
_pdbx_chem_comp_synonyms.ordinal      1 
_pdbx_chem_comp_synonyms.comp_id      A1EK0 
_pdbx_chem_comp_synonyms.name         "Btk Kinase inhibitor" 
_pdbx_chem_comp_synonyms.provenance   PUBCHEM 
_pdbx_chem_comp_synonyms.type         ? 
# 
