data_TKF
# 
_chem_comp.id                                    TKF 
_chem_comp.name                                  "(3S)-N-[(1-benzothiophen-5-yl)methyl]-1-{2-[4-(trifluoromethyl)phenyl]-2H-pyrazolo[3,4-d]pyrimidin-4-yl}piperidine-3-carboxamide" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C27 H23 F3 N6 O S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2022-07-26 
_chem_comp.pdbx_modified_date                    2023-03-03 
_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                        536.571 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     TKF 
_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        8DTJ 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
# 
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 
TKF C11 C1  C 0 1 Y N N 11.954 4.071  -5.026  9.188   -1.796 -2.013 C11 TKF 1  
TKF C10 C2  C 0 1 Y N N 10.637 3.930  -4.615  10.084  -2.697 -1.663 C10 TKF 2  
TKF C12 C3  C 0 1 Y N N 12.229 3.347  -6.272  8.516   -1.139 -0.903 C12 TKF 3  
TKF C02 C4  C 0 1 N N N 16.621 0.532  -9.554  3.513   1.551  0.121  C02 TKF 4  
TKF C04 C5  C 0 1 N N N 14.981 2.484  -8.908  5.944   1.418  0.192  C04 TKF 5  
TKF C05 C6  C 0 1 Y N N 13.608 2.554  -8.165  7.009   0.352  0.236  C05 TKF 6  
TKF C06 C7  C 0 1 Y N N 12.473 1.870  -8.658  7.460   -0.119 1.461  C06 TKF 7  
TKF C07 C8  C 0 1 Y N N 11.242 1.922  -7.984  8.431   -1.091 1.513  C07 TKF 8  
TKF C08 C9  C 0 1 Y N N 11.151 2.666  -6.800  8.969   -1.611 0.332  C08 TKF 9  
TKF C13 C10 C 0 1 Y N N 13.464 3.283  -6.962  7.518   -0.140 -0.926 C13 TKF 10 
TKF C14 C11 C 0 1 N N S 17.181 -0.902 -9.291  2.153   0.902  0.092  C14 TKF 11 
TKF C15 C12 C 0 1 N N N 16.092 -1.872 -8.629  1.071   1.984  0.047  C15 TKF 12 
TKF C17 C13 C 0 1 Y N N 14.056 -1.275 -6.929  -1.247  2.291  -0.132 C17 TKF 13 
TKF C19 C14 C 0 1 Y N N 11.752 -1.914 -6.967  -1.901  4.495  -0.440 C19 TKF 14 
TKF C21 C15 C 0 1 Y N N 12.329 -0.305 -5.382  -3.645  2.983  -0.360 C21 TKF 15 
TKF C24 C16 C 0 1 Y N N 13.848 2.209  -3.092  -5.715  0.099  -0.151 C24 TKF 16 
TKF C25 C17 C 0 1 Y N N 13.114 2.321  -1.893  -7.031  0.524  -0.282 C25 TKF 17 
TKF C26 C18 C 0 1 Y N N 13.431 3.279  -0.912  -8.059  -0.398 -0.244 C26 TKF 18 
TKF C27 C19 C 0 1 Y N N 14.499 4.155  -1.094  -7.780  -1.742 -0.076 C27 TKF 19 
TKF C28 C20 C 0 1 N N N 14.836 5.170  -0.048  -8.905  -2.744 -0.036 C28 TKF 20 
TKF C32 C21 C 0 1 Y N N 15.248 4.067  -2.263  -6.471  -2.168 0.054  C32 TKF 21 
TKF C33 C22 C 0 1 Y N N 14.928 3.106  -3.246  -5.438  -1.252 0.017  C33 TKF 22 
TKF C34 C23 C 0 1 Y N N 14.385 0.565  -5.034  -3.366  0.731  -0.080 C34 TKF 23 
TKF C35 C24 C 0 1 Y N N 13.694 -0.366 -5.843  -2.656  1.906  -0.173 C35 TKF 24 
TKF C36 C25 C 0 1 N N N 16.569 -0.617 -6.511  -0.476  0.568  1.261  C36 TKF 25 
TKF C37 C26 C 0 1 N N N 17.993 -1.112 -6.908  0.559   -0.556 1.342  C37 TKF 26 
TKF C38 C27 C 0 1 N N N 18.374 -0.797 -8.362  1.964   0.051  1.351  C38 TKF 27 
TKF F29 F1  F 0 1 N N N 14.754 6.498  -0.397  -8.537  -3.825 0.773  F29 TKF 28 
TKF F30 F2  F 0 1 N N N 14.086 5.152  1.101   -10.051 -2.137 0.489  F30 TKF 29 
TKF F31 F3  F 0 1 N N N 16.106 5.094  0.449   -9.170  -3.200 -1.331 F31 TKF 30 
TKF N03 N1  N 0 1 N N N 15.613 1.150  -8.779  4.622   0.788  0.163  N03 TKF 31 
TKF N16 N2  N 0 1 N N N 15.510 -1.274 -7.356  -0.255  1.352  0.039  N16 TKF 32 
TKF N18 N3  N 0 1 Y N N 13.087 -2.014 -7.465  -0.960  3.580  -0.270 N18 TKF 33 
TKF N20 N4  N 0 1 Y N N 11.326 -1.118 -5.974  -3.182  4.241  -0.490 N20 TKF 34 
TKF N22 N5  N 0 1 Y N N 12.207 0.619  -4.345  -4.829  2.410  -0.366 N22 TKF 35 
TKF N23 N6  N 0 1 Y N N 13.488 1.152  -4.140  -4.670  1.030  -0.195 N23 TKF 36 
TKF O01 O1  O 0 1 N N N 17.093 1.174  -10.512 3.608   2.760  0.108  O01 TKF 37 
TKF S09 S1  S 0 1 Y N N 9.784  2.927  -5.741  10.196  -2.846 0.080  S09 TKF 38 
TKF H1  H1  H 0 1 N N N 12.693 4.648  -4.490  8.974   -1.559 -3.044 H1  TKF 39 
TKF H2  H2  H 0 1 N N N 10.209 4.377  -3.730  10.674  -3.272 -2.362 H2  TKF 40 
TKF H3  H3  H 0 1 N N N 15.656 3.240  -8.480  6.026   2.050  1.076  H3  TKF 41 
TKF H4  H4  H 0 1 N N N 14.819 2.699  -9.975  6.076   2.027  -0.703 H4  TKF 42 
TKF H5  H5  H 0 1 N N N 12.554 1.297  -9.570  7.048   0.280  2.376  H5  TKF 43 
TKF H6  H6  H 0 1 N N N 10.381 1.398  -8.371  8.780   -1.454 2.469  H6  TKF 44 
TKF H7  H7  H 0 1 N N N 14.319 3.805  -6.558  7.158   0.235  -1.872 H7  TKF 45 
TKF H8  H8  H 0 1 N N N 17.500 -1.340 -10.248 2.071   0.269  -0.792 H8  TKF 46 
TKF H9  H9  H 0 1 N N N 15.278 -2.039 -9.350  1.163   2.625  0.923  H9  TKF 47 
TKF H10 H10 H 0 1 N N N 16.570 -2.833 -8.386  1.194   2.583  -0.856 H10 TKF 48 
TKF H11 H11 H 0 1 N N N 11.010 -2.543 -7.437  -1.588  5.523  -0.550 H11 TKF 49 
TKF H12 H12 H 0 1 N N N 12.284 1.652  -1.723  -7.250  1.573  -0.412 H12 TKF 50 
TKF H13 H13 H 0 1 N N N 12.841 3.336  -0.009  -9.083  -0.068 -0.345 H13 TKF 51 
TKF H14 H14 H 0 1 N N N 16.080 4.738  -2.419  -6.256  -3.218 0.185  H14 TKF 52 
TKF H15 H15 H 0 1 N N N 15.527 3.055  -4.143  -4.416  -1.585 0.119  H15 TKF 53 
TKF H16 H16 H 0 1 N N N 15.440 0.787  -5.098  -2.949  -0.255 0.061  H16 TKF 54 
TKF H17 H17 H 0 1 N N N 16.516 0.473  -6.652  -1.478  0.139  1.240  H17 TKF 55 
TKF H18 H18 H 0 1 N N N 16.386 -0.860 -5.454  -0.377  1.217  2.131  H18 TKF 56 
TKF H19 H19 H 0 1 N N N 18.033 -2.202 -6.767  0.404   -1.128 2.256  H19 TKF 57 
TKF H20 H20 H 0 1 N N N 18.726 -0.629 -6.245  0.451   -1.213 0.479  H20 TKF 58 
TKF H21 H21 H 0 1 N N N 19.145 -1.509 -8.691  2.706   -0.748 1.365  H21 TKF 59 
TKF H22 H22 H 0 1 N N N 18.775 0.226  -8.411  2.085   0.677  2.235  H22 TKF 60 
TKF H23 H23 H 0 1 N N N 15.271 0.596  -8.020  4.546   -0.179 0.174  H23 TKF 61 
# 
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 
TKF O01 C02 DOUB N N 1  
TKF C02 C14 SING N N 2  
TKF C02 N03 SING N N 3  
TKF C14 C15 SING N N 4  
TKF C14 C38 SING N N 5  
TKF C04 N03 SING N N 6  
TKF C04 C05 SING N N 7  
TKF C06 C05 DOUB Y N 8  
TKF C06 C07 SING Y N 9  
TKF C15 N16 SING N N 10 
TKF C38 C37 SING N N 11 
TKF C05 C13 SING Y N 12 
TKF C07 C08 DOUB Y N 13 
TKF N18 C19 SING Y N 14 
TKF N18 C17 DOUB Y N 15 
TKF N16 C17 SING N N 16 
TKF N16 C36 SING N N 17 
TKF C19 N20 DOUB Y N 18 
TKF C13 C12 DOUB Y N 19 
TKF C17 C35 SING Y N 20 
TKF C37 C36 SING N N 21 
TKF C08 C12 SING Y N 22 
TKF C08 S09 SING Y N 23 
TKF C12 C11 SING Y N 24 
TKF N20 C21 SING Y N 25 
TKF C35 C21 SING Y N 26 
TKF C35 C34 DOUB Y N 27 
TKF S09 C10 SING Y N 28 
TKF C21 N22 DOUB Y N 29 
TKF C34 N23 SING Y N 30 
TKF C11 C10 DOUB Y N 31 
TKF N22 N23 SING Y N 32 
TKF N23 C24 SING N N 33 
TKF C33 C24 DOUB Y N 34 
TKF C33 C32 SING Y N 35 
TKF C24 C25 SING Y N 36 
TKF C32 C27 DOUB Y N 37 
TKF C25 C26 DOUB Y N 38 
TKF C27 C26 SING Y N 39 
TKF C27 C28 SING N N 40 
TKF F29 C28 SING N N 41 
TKF C28 F31 SING N N 42 
TKF C28 F30 SING N N 43 
TKF C11 H1  SING N N 44 
TKF C10 H2  SING N N 45 
TKF C04 H3  SING N N 46 
TKF C04 H4  SING N N 47 
TKF C06 H5  SING N N 48 
TKF C07 H6  SING N N 49 
TKF C13 H7  SING N N 50 
TKF C14 H8  SING N N 51 
TKF C15 H9  SING N N 52 
TKF C15 H10 SING N N 53 
TKF C19 H11 SING N N 54 
TKF C25 H12 SING N N 55 
TKF C26 H13 SING N N 56 
TKF C32 H14 SING N N 57 
TKF C33 H15 SING N N 58 
TKF C34 H16 SING N N 59 
TKF C36 H17 SING N N 60 
TKF C36 H18 SING N N 61 
TKF C37 H19 SING N N 62 
TKF C37 H20 SING N N 63 
TKF C38 H21 SING N N 64 
TKF C38 H22 SING N N 65 
TKF N03 H23 SING N N 66 
# 
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 
TKF SMILES           ACDLabs              12.01 "FC(F)(F)c1ccc(cc1)n1cc2c(n1)ncnc2N1CCCC(C1)C(=O)NCc1cc2ccsc2cc1"                                                                                                                                            
TKF InChI            InChI                1.06  "InChI=1S/C27H23F3N6OS/c28-27(29,30)20-4-6-21(7-5-20)36-15-22-24(34-36)32-16-33-25(22)35-10-1-2-19(14-35)26(37)31-13-17-3-8-23-18(12-17)9-11-38-23/h3-9,11-12,15-16,19H,1-2,10,13-14H2,(H,31,37)/t19-/m0/s1" 
TKF InChIKey         InChI                1.06  RPVUYLFRBVBINJ-IBGZPJMESA-N                                                                                                                                                                                  
TKF SMILES_CANONICAL CACTVS               3.385 "FC(F)(F)c1ccc(cc1)n2cc3c(ncnc3N4CCC[C@@H](C4)C(=O)NCc5ccc6sccc6c5)n2"                                                                                                                                       
TKF SMILES           CACTVS               3.385 "FC(F)(F)c1ccc(cc1)n2cc3c(ncnc3N4CCC[CH](C4)C(=O)NCc5ccc6sccc6c5)n2"                                                                                                                                         
TKF SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "c1cc(ccc1C(F)(F)F)n2cc3c(n2)ncnc3N4CCC[C@@H](C4)C(=O)NCc5ccc6c(c5)ccs6"                                                                                                                                     
TKF SMILES           "OpenEye OEToolkits" 2.0.7 "c1cc(ccc1C(F)(F)F)n2cc3c(n2)ncnc3N4CCCC(C4)C(=O)NCc5ccc6c(c5)ccs6"                                                                                                                                          
# 
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 
TKF "SYSTEMATIC NAME" ACDLabs              12.01 "(3S)-N-[(1-benzothiophen-5-yl)methyl]-1-{2-[4-(trifluoromethyl)phenyl]-2H-pyrazolo[3,4-d]pyrimidin-4-yl}piperidine-3-carboxamide" 
TKF "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.7 "(3~{S})-~{N}-(1-benzothiophen-5-ylmethyl)-1-[2-[4-(trifluoromethyl)phenyl]pyrazolo[3,4-d]pyrimidin-4-yl]piperidine-3-carboxamide" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
TKF "Create component" 2022-07-26 RCSB 
TKF "Initial release"  2023-03-08 RCSB 
# 
