data_O5I
# 
_chem_comp.id                                    O5I 
_chem_comp.name                                  "2-chloranyl-~{N}-[[1-[1-[(4-chlorophenyl)amino]cyclopentyl]carbonylpiperidin-4-yl]methyl]ethanamide" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H27 Cl2 N3 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2022-08-30 
_chem_comp.pdbx_modified_date                    2024-09-27 
_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                        412.353 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     O5I 
_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        8ATS 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBE 
_chem_comp.pdbx_pcm                              Y 
# 
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_backbone_atom_flag 
_chem_comp_atom.pdbx_n_terminal_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 
O5I C1  C1  C  0 1 N N N N N N 21.737 26.152 -2.824 5.665  0.551  0.003  C1  O5I 1  
O5I C2  C2  C  0 1 N N N N N N 21.356 27.132 -3.912 6.364  1.217  -1.154 C2  O5I 2  
O5I N3  N1  N  0 1 N N N N N N 17.383 19.778 0.745  -2.245 -0.900 -1.301 N3  O5I 3  
O5I C4  C3  C  0 1 N N N N N N 19.556 23.292 -2.133 2.133  0.187  1.109  C4  O5I 4  
O5I C5  C4  C  0 1 N N N N N N 19.568 21.876 -1.559 1.615  -0.530 -0.140 C5  O5I 5  
O5I C7  C5  C  0 1 N N N N N N 16.081 21.470 -0.644 -1.582 -1.557 0.948  C7  O5I 6  
O5I C8  C6  C  0 1 N N N N N N 16.124 20.058 -0.013 -2.146 -2.026 -0.369 C8  O5I 7  
O5I C9  C7  C  0 1 Y N N N N N 18.068 20.693 1.557  -2.964 0.243  -0.943 C9  O5I 8  
O5I C10 C8  C  0 1 Y N N N N N 19.394 20.427 1.897  -2.957 1.358  -1.771 C10 O5I 9  
O5I C11 C9  C  0 1 Y N N N N N 20.106 21.309 2.686  -3.668 2.487  -1.415 C11 O5I 10 
O5I C12 C10 C  0 1 Y N N N N N 19.495 22.455 3.136  -4.389 2.508  -0.233 C12 O5I 11 
O5I C13 C11 C  0 1 Y N N N N N 18.185 22.738 2.825  -4.397 1.398  0.594  C13 O5I 12 
O5I C14 C12 C  0 1 Y N N N N N 17.470 21.862 2.036  -3.693 0.265  0.240  C14 O5I 13 
O5I C15 C13 C  0 1 N N N N N N 15.864 18.938 -1.051 -3.537 -2.657 -0.153 C15 O5I 14 
O5I C16 C14 C  0 1 N N N N N N 14.941 17.922 -0.378 -3.577 -3.840 -1.151 C16 O5I 15 
O5I C17 C15 C  0 1 N N N N N N 14.697 18.416 1.038  -2.130 -4.389 -1.088 C17 O5I 16 
O5I C18 C16 C  0 1 N N N N N N 14.926 19.900 0.951  -1.251 -3.126 -0.964 C18 O5I 17 
O5I C19 C17 C  0 1 N N N N N N 17.058 23.267 -1.973 -0.073 -0.125 2.238  C19 O5I 18 
O5I O1  O1  O  0 1 N N N N N N 22.855 26.120 -2.196 6.311  -0.036 0.845  O1  O5I 19 
O5I N1  N2  N  0 1 N N N N N N 20.751 25.280 -2.669 4.322  0.612  0.105  N1  O5I 20 
O5I C3  C18 C  0 1 N N N N N N 20.811 24.094 -1.829 3.643  -0.031 1.232  C3  O5I 21 
O5I C6  C19 C  0 1 N N N N N N 18.280 21.135 -1.887 0.110  -0.282 -0.279 C6  O5I 22 
O5I N2  N3  N  0 1 N N N N N N 17.094 21.893 -1.439 -0.553 -0.687 0.968  N2  O5I 23 
O5I O2  O2  O  0 1 N N N N N N 15.115 22.198 -0.385 -2.055 -1.962 1.989  O2  O5I 24 
O5I CL2 CL1 CL 0 0 N N N N N N 20.394 23.576 4.115  -5.282 3.928  0.212  CL2 O5I 25 
O5I C20 C20 C  0 1 N N N N N N 18.324 24.006 -1.586 1.435  -0.375 2.349  C20 O5I 26 
O5I H1  H1  H  0 1 N N N N N N 20.360 27.580 -3.780 6.010  0.786  -2.090 H1  O5I 27 
O5I H2  H2  H  0 1 N N N N N N 22.097 27.928 -4.075 6.149  2.286  -1.141 H2  O5I 28 
O5I H4  H4  H  0 1 N N N N N N 17.165 19.007 1.343  -1.811 -0.948 -2.168 H4  O5I 29 
O5I H5  H5  H  0 1 N N N N N N 19.452 23.217 -3.226 1.926  1.254  1.028  H5  O5I 30 
O5I H6  H6  H  0 1 N N N N N N 20.418 21.323 -1.986 2.130  -0.146 -1.020 H6  O5I 31 
O5I H7  H7  H  0 1 N N N N N N 19.680 21.933 -0.466 1.801  -1.600 -0.048 H7  O5I 32 
O5I H8  H8  H  0 1 N N N N N N 19.868 19.524 1.541  -2.395 1.343  -2.693 H8  O5I 33 
O5I H9  H9  H  0 1 N N N N N N 21.133 21.100 2.947  -3.663 3.354  -2.058 H9  O5I 34 
O5I H10 H10 H  0 1 N N N N N N 17.720 23.639 3.196  -4.960 1.418  1.516  H10 O5I 35 
O5I H11 H11 H  0 1 N N N N N N 16.442 22.080 1.787  -3.704 -0.602 0.883  H11 O5I 36 
O5I H12 H12 H  0 1 N N N N N N 16.812 18.458 -1.337 -3.638 -3.017 0.871  H12 O5I 37 
O5I H13 H13 H  0 1 N N N N N N 15.380 19.356 -1.946 -4.323 -1.937 -0.383 H13 O5I 38 
O5I H14 H14 H  0 1 N N N N N N 13.989 17.856 -0.925 -4.292 -4.596 -0.826 H14 O5I 39 
O5I H15 H15 H  0 1 N N N N N N 15.420 16.932 -0.356 -3.813 -3.490 -2.156 H15 O5I 40 
O5I H16 H16 H  0 1 N N N N N N 13.667 18.197 1.356  -2.003 -5.030 -0.215 H16 O5I 41 
O5I H17 H17 H  0 1 N N N N N N 15.404 17.952 1.741  -1.889 -4.935 -2.000 H17 O5I 42 
O5I H18 H18 H  0 1 N N N N N N 15.168 20.314 1.941  -0.890 -2.823 -1.947 H18 O5I 43 
O5I H19 H19 H  0 1 N N N N N N 14.036 20.407 0.550  -0.408 -3.321 -0.301 H19 O5I 44 
O5I H20 H20 H  0 1 N N N N N N 16.186 23.796 -1.560 -0.268 0.947  2.261  H20 O5I 45 
O5I H21 H21 H  0 1 N N N N N N 16.978 23.230 -3.069 -0.586 -0.610 3.069  H21 O5I 46 
O5I H22 H22 H  0 1 N N N N N N 19.901 25.450 -3.168 3.806  1.082  -0.569 H22 O5I 47 
O5I H23 H23 H  0 1 N N N N N N 21.708 23.503 -2.068 3.998  0.405  2.166  H23 O5I 48 
O5I H24 H24 H  0 1 N N N N N N 20.832 24.380 -0.767 3.858  -1.099 1.225  H24 O5I 49 
O5I H25 H25 H  0 1 N N N N N N 18.220 20.986 -2.975 -0.070 0.777  -0.461 H25 O5I 50 
O5I H26 H26 H  0 1 N N N N N N 18.291 20.157 -1.383 -0.282 -0.870 -1.109 H26 O5I 51 
O5I H27 H27 H  0 1 N N N N N N 18.392 24.054 -0.489 1.622  -1.447 2.418  H27 O5I 52 
O5I H28 H28 H  0 1 N N N N N N 18.286 25.026 -1.996 1.821  0.119  3.240  H28 O5I 53 
O5I CL1 CL2 CL 0 0 N Y N N N N 21.413 25.748 -5.213 8.143  0.960  -1.009 CL1 O5I 54 
# 
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 
O5I C2  C1  SING N N 1  
O5I C1  N1  SING N N 2  
O5I C1  O1  DOUB N N 3  
O5I N1  C3  SING N N 4  
O5I C4  C3  SING N N 5  
O5I C4  C20 SING N N 6  
O5I C4  C5  SING N N 7  
O5I C19 C20 SING N N 8  
O5I C19 N2  SING N N 9  
O5I C6  C5  SING N N 10 
O5I C6  N2  SING N N 11 
O5I N2  C7  SING N N 12 
O5I C15 C16 SING N N 13 
O5I C15 C8  SING N N 14 
O5I C7  O2  DOUB N N 15 
O5I C7  C8  SING N N 16 
O5I C16 C17 SING N N 17 
O5I C8  N3  SING N N 18 
O5I C8  C18 SING N N 19 
O5I N3  C9  SING N N 20 
O5I C18 C17 SING N N 21 
O5I C9  C10 DOUB Y N 22 
O5I C9  C14 SING Y N 23 
O5I C10 C11 SING Y N 24 
O5I C14 C13 DOUB Y N 25 
O5I C11 C12 DOUB Y N 26 
O5I C13 C12 SING Y N 27 
O5I C12 CL2 SING N N 28 
O5I C2  H1  SING N N 29 
O5I C2  H2  SING N N 30 
O5I N3  H4  SING N N 31 
O5I C4  H5  SING N N 32 
O5I C5  H6  SING N N 33 
O5I C5  H7  SING N N 34 
O5I C10 H8  SING N N 35 
O5I C11 H9  SING N N 36 
O5I C13 H10 SING N N 37 
O5I C14 H11 SING N N 38 
O5I C15 H12 SING N N 39 
O5I C15 H13 SING N N 40 
O5I C16 H14 SING N N 41 
O5I C16 H15 SING N N 42 
O5I C17 H16 SING N N 43 
O5I C17 H17 SING N N 44 
O5I C18 H18 SING N N 45 
O5I C18 H19 SING N N 46 
O5I C19 H20 SING N N 47 
O5I C19 H21 SING N N 48 
O5I N1  H22 SING N N 49 
O5I C3  H23 SING N N 50 
O5I C3  H24 SING N N 51 
O5I C6  H25 SING N N 52 
O5I C6  H26 SING N N 53 
O5I C20 H27 SING N N 54 
O5I C20 H28 SING N N 55 
O5I C2  CL1 SING N N 56 
# 
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 
O5I InChI            InChI                1.06    "InChI=1S/C20H27Cl2N3O2/c21-13-18(26)23-14-15-7-11-25(12-8-15)19(27)20(9-1-2-10-20)24-17-5-3-16(22)4-6-17/h3-6,15,24H,1-2,7-14H2,(H,23,26)" 
O5I InChIKey         InChI                1.06    NJCJNBJGRFJESB-UHFFFAOYSA-N                                                                                                                 
O5I SMILES_CANONICAL CACTVS               3.385   "ClCC(=O)NCC1CCN(CC1)C(=O)C2(CCCC2)Nc3ccc(Cl)cc3"                                                                                           
O5I SMILES           CACTVS               3.385   "ClCC(=O)NCC1CCN(CC1)C(=O)C2(CCCC2)Nc3ccc(Cl)cc3"                                                                                           
O5I SMILES_CANONICAL "OpenEye OEToolkits" 3.1.0.0 "c1cc(ccc1NC2(CCCC2)C(=O)N3CCC(CC3)CNC(=O)CCl)Cl"                                                                                           
O5I SMILES           "OpenEye OEToolkits" 3.1.0.0 "c1cc(ccc1NC2(CCCC2)C(=O)N3CCC(CC3)CNC(=O)CCl)Cl"                                                                                           
# 
_pdbx_chem_comp_identifier.comp_id           O5I 
_pdbx_chem_comp_identifier.type              "SYSTEMATIC NAME" 
_pdbx_chem_comp_identifier.program           "OpenEye OEToolkits" 
_pdbx_chem_comp_identifier.program_version   3.1.0.0 
_pdbx_chem_comp_identifier.identifier        "2-chloranyl-~{N}-[[1-[1-[(4-chlorophenyl)amino]cyclopentyl]carbonylpiperidin-4-yl]methyl]ethanamide" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
O5I "Create component" 2022-08-30 PDBE 
O5I "Initial release"  2023-09-20 RCSB 
O5I "Modify PCM"       2024-09-27 PDBE 
# 
_pdbx_chem_comp_pcm.pcm_id                             1 
_pdbx_chem_comp_pcm.comp_id                            O5I 
_pdbx_chem_comp_pcm.modified_residue_id                CYS 
_pdbx_chem_comp_pcm.type                               None 
_pdbx_chem_comp_pcm.category                           "Covalent chemical modification" 
_pdbx_chem_comp_pcm.position                           "Amino-acid side chain" 
_pdbx_chem_comp_pcm.polypeptide_position               "Any position" 
_pdbx_chem_comp_pcm.comp_id_linking_atom               C2 
_pdbx_chem_comp_pcm.modified_residue_id_linking_atom   SG 
_pdbx_chem_comp_pcm.uniprot_specific_ptm_accession     ? 
_pdbx_chem_comp_pcm.uniprot_generic_ptm_accession      ? 
# 
