data_KKO
# 
_chem_comp.id                                    KKO 
_chem_comp.name                                  "(2~{S})-1-(3,4-dichlorophenyl)-4-(4-methoxypyridin-3-yl)carbonyl-~{N}-(thiophen-2-ylmethyl)piperazine-2-carboxamide" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H22 Cl2 N4 O3 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2023-08-15 
_chem_comp.pdbx_modified_date                    2023-12-01 
_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                        505.417 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     KKO 
_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        8Q71 
_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_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 
KKO N3   N1  N  0 1 N N N N N N -12.704 13.435 10.012 -0.300 1.721  0.425  N3   KKO 1  
KKO C4   C1  C  0 1 N N N N N N -13.154 14.712 9.502  0.076  3.094  0.769  C4   KKO 2  
KKO C5   C2  C  0 1 Y N N N N N -12.689 15.796 10.423 -1.051 4.029  0.413  C5   KKO 3  
KKO C6   C3  C  0 1 Y N N N N N -13.113 16.077 11.714 -2.051 4.372  1.226  C6   KKO 4  
KKO C7   C4  C  0 1 Y N N N N N -12.404 17.177 12.279 -2.974 5.247  0.678  C7   KKO 5  
KKO C8   C5  C  0 1 Y N N N N N -11.492 17.685 11.431 -2.723 5.614  -0.579 C8   KKO 6  
KKO C10  C6  C  0 1 N N S N N N -11.120 11.682 10.548 0.167  -0.706 0.314  C10  KKO 7  
KKO N12  N2  N  0 1 N N N N N N -11.110 9.266  10.268 -1.365 -2.523 0.858  N12  KKO 8  
KKO C13  C7  C  0 1 N N N N N N -12.019 9.080  11.397 -0.271 -3.485 1.057  C13  KKO 9  
KKO C17  C8  C  0 1 Y N N N N N -10.670 13.396 12.807 3.582  -0.990 0.901  C17  KKO 10 
KKO C20  C9  C  0 1 Y N N N N N -11.789 14.758 14.445 4.856  -0.363 -1.030 C20  KKO 11 
KKO C21  C10 C  0 1 Y N N N N N -12.902 13.945 14.363 3.748  -0.571 -1.833 C21  KKO 12 
KKO C22  C11 C  0 1 Y N N N N N -12.909 12.861 13.505 2.553  -0.978 -1.272 C22  KKO 13 
KKO C24  C12 C  0 1 N N N N N N -10.112 8.395  10.011 -2.586 -2.935 0.465  C24  KKO 14 
KKO C26  C13 C  0 1 Y N N N N N -8.001  8.894  8.756  -4.030 -1.184 1.500  C26  KKO 15 
KKO C28  C14 C  0 1 Y N N N N N -7.737  8.529  6.519  -5.757 -0.176 0.348  C28  KKO 16 
KKO C11  C15 C  0 1 N N N N N N -11.438 10.520 9.602  -1.090 -1.098 1.097  C11  KKO 17 
KKO C14  C16 C  0 1 N N N N N N -11.783 10.163 12.423 0.954  -2.999 0.275  C14  KKO 18 
KKO C16  C17 C  0 1 Y N N N N N -11.798 12.575 12.717 2.468  -1.194 0.098  C16  KKO 19 
KKO C18  C18 C  0 1 Y N N N N N -10.674 14.480 13.665 4.773  -0.572 0.336  C18  KKO 20 
KKO C2   C19 C  0 1 N N N N N N -11.430 13.042 9.927  0.557  0.708  0.662  C2   KKO 21 
KKO C25  C20 C  0 1 Y N N N N N -9.345  8.525  8.724  -3.703 -1.973 0.397  C25  KKO 22 
KKO C29  C21 C  0 1 Y N N N N N -9.055  8.148  6.363  -5.500 -0.911 -0.790 C29  KKO 23 
KKO C30  C22 C  0 1 Y N N N N N -9.867  8.153  7.485  -4.458 -1.834 -0.782 C30  KKO 24 
KKO C32  C23 C  0 1 N N N N N N -11.745 7.358  6.245  -4.997 -2.368 -3.032 C32  KKO 25 
KKO N15  N3  N  0 1 N N N N N N -11.842 11.501 11.820 1.264  -1.617 0.666  N15  KKO 26 
KKO N27  N4  N  0 1 Y N N N N N -7.200  8.899  7.685  -5.030 -0.330 1.441  N27  KKO 27 
KKO O1   O1  O  0 1 N N N N N N -10.549 13.709 9.391  1.642  0.934  1.154  O1   KKO 28 
KKO O31  O2  O  0 1 N N N N N N -11.196 7.848  7.465  -4.178 -2.578 -1.880 O31  KKO 29 
KKO O33  O3  O  0 1 N N N N N N -9.807  7.516  10.795 -2.768 -4.100 0.168  O33  KKO 30 
KKO S9   S1  S  0 1 Y N N N N N -11.457 16.864 9.937  -1.246 4.838  -1.137 S9   KKO 31 
KKO CL19 CL1 CL 0 0 N N N N N N -9.275  15.505 13.722 6.164  -0.310 1.340  CL19 KKO 32 
KKO CL23 CL2 CL 0 0 N N N N N N -11.841 16.160 15.462 6.352  0.162  -1.737 CL23 KKO 33 
KKO H3   H1  H  0 1 N N N N N N -13.370 12.826 10.443 -1.168 1.540  0.031  H3   KKO 34 
KKO H4B  H2  H  0 1 N N N N N N -12.735 14.876 8.498  0.278  3.159  1.838  H4B  KKO 35 
KKO H4A  H3  H  0 1 N N N N N N -14.253 14.721 9.447  0.971  3.376  0.213  H4A  KKO 36 
KKO H6   H4  H  0 1 N N N N N N -13.887 15.528 12.229 -2.135 3.997  2.235  H6   KKO 37 
KKO H7   H5  H  0 1 N N N N N N -12.579 17.559 13.274 -3.832 5.606  1.228  H7   KKO 38 
KKO H8   H6  H  0 1 N N N N N N -10.852 18.521 11.670 -3.332 6.286  -1.165 H8   KKO 39 
KKO H10  H7  H  0 1 N N N N N N -10.041 11.652 10.758 -0.035 -0.775 -0.755 H10  KKO 40 
KKO H13A H8  H  0 0 N N N N N N -13.059 9.133  11.042 -0.027 -3.547 2.118  H13A KKO 41 
KKO H13B H9  H  0 0 N N N N N N -11.837 8.096  11.855 -0.574 -4.466 0.690  H13B KKO 42 
KKO H17  H10 H  0 1 N N N N N N -9.797  13.184 12.207 3.518  -1.154 1.967  H17  KKO 43 
KKO H21  H11 H  0 1 N N N N N N -13.769 14.156 14.971 3.816  -0.407 -2.898 H21  KKO 44 
KKO H22  H12 H  0 1 N N N N N N -13.784 12.231 13.446 1.689  -1.140 -1.899 H22  KKO 45 
KKO H26  H13 H  0 1 N N N N N N -7.581  9.194  9.704  -3.461 -1.279 2.413  H26  KKO 46 
KKO H28  H14 H  0 1 N N N N N N -7.102  8.528  5.646  -6.567 0.538  0.347  H28  KKO 47 
KKO H11B H15 H  0 0 N N N N N N -10.841 10.618 8.683  -0.925 -0.930 2.162  H11B KKO 48 
KKO H11A H16 H  0 0 N N N N N N -12.508 10.534 9.347  -1.935 -0.500 0.757  H11A KKO 49 
KKO H14B H17 H  0 0 N N N N N N -12.554 10.089 13.204 1.807  -3.640 0.500  H14B KKO 50 
KKO H14A H18 H  0 0 N N N N N N -10.790 10.018 12.873 0.742  -3.037 -0.793 H14A KKO 51 
KKO H29  H19 H  0 1 N N N N N N -9.440  7.856  5.397  -6.102 -0.775 -1.676 H29  KKO 52 
KKO H32C H20 H  0 0 N N N N N N -12.818 7.157  6.380  -6.035 -2.591 -2.784 H32C KKO 53 
KKO H32A H21 H  0 0 N N N N N N -11.609 8.110  5.454  -4.914 -1.330 -3.352 H32A KKO 54 
KKO H32B H22 H  0 0 N N N N N N -11.231 6.428  5.959  -4.667 -3.025 -3.837 H32B KKO 55 
# 
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 
KKO C32 O31  SING N N 1  
KKO C29 C28  DOUB Y N 2  
KKO C29 C30  SING Y N 3  
KKO C28 N27  SING Y N 4  
KKO O31 C30  SING N N 5  
KKO C30 C25  DOUB Y N 6  
KKO N27 C26  DOUB Y N 7  
KKO C25 C26  SING Y N 8  
KKO C25 C24  SING N N 9  
KKO O1  C2   DOUB N N 10 
KKO C4  N3   SING N N 11 
KKO C4  C5   SING N N 12 
KKO C11 N12  SING N N 13 
KKO C11 C10  SING N N 14 
KKO C2  N3   SING N N 15 
KKO C2  C10  SING N N 16 
KKO S9  C5   SING Y N 17 
KKO S9  C8   SING Y N 18 
KKO C24 N12  SING N N 19 
KKO C24 O33  DOUB N N 20 
KKO N12 C13  SING N N 21 
KKO C5  C6   DOUB Y N 22 
KKO C10 N15  SING N N 23 
KKO C13 C14  SING N N 24 
KKO C8  C7   DOUB Y N 25 
KKO C6  C7   SING Y N 26 
KKO N15 C14  SING N N 27 
KKO N15 C16  SING N N 28 
KKO C16 C17  DOUB Y N 29 
KKO C16 C22  SING Y N 30 
KKO C17 C18  SING Y N 31 
KKO C22 C21  DOUB Y N 32 
KKO C18 CL19 SING N N 33 
KKO C18 C20  DOUB Y N 34 
KKO C21 C20  SING Y N 35 
KKO C20 CL23 SING N N 36 
KKO N3  H3   SING N N 37 
KKO C4  H4B  SING N N 38 
KKO C4  H4A  SING N N 39 
KKO C6  H6   SING N N 40 
KKO C7  H7   SING N N 41 
KKO C8  H8   SING N N 42 
KKO C10 H10  SING N N 43 
KKO C13 H13A SING N N 44 
KKO C13 H13B SING N N 45 
KKO C17 H17  SING N N 46 
KKO C21 H21  SING N N 47 
KKO C22 H22  SING N N 48 
KKO C26 H26  SING N N 49 
KKO C28 H28  SING N N 50 
KKO C11 H11B SING N N 51 
KKO C11 H11A SING N N 52 
KKO C14 H14B SING N N 53 
KKO C14 H14A SING N N 54 
KKO C29 H29  SING N N 55 
KKO C32 H32C SING N N 56 
KKO C32 H32A SING N N 57 
KKO C32 H32B SING N N 58 
# 
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 
KKO InChI            InChI                1.06  "InChI=1S/C23H22Cl2N4O3S/c1-32-21-6-7-26-13-17(21)23(31)28-8-9-29(15-4-5-18(24)19(25)11-15)20(14-28)22(30)27-12-16-3-2-10-33-16/h2-7,10-11,13,20H,8-9,12,14H2,1H3,(H,27,30)/t20-/m0/s1" 
KKO InChIKey         InChI                1.06  XAKMNISRDIXWHA-FQEVSTJZSA-N                                                                                                                                                             
KKO SMILES_CANONICAL CACTVS               3.385 "COc1ccncc1C(=O)N2CCN([C@@H](C2)C(=O)NCc3sccc3)c4ccc(Cl)c(Cl)c4"                                                                                                                        
KKO SMILES           CACTVS               3.385 "COc1ccncc1C(=O)N2CCN([CH](C2)C(=O)NCc3sccc3)c4ccc(Cl)c(Cl)c4"                                                                                                                          
KKO SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "COc1ccncc1C(=O)N2CCN([C@@H](C2)C(=O)NCc3cccs3)c4ccc(c(c4)Cl)Cl"                                                                                                                        
KKO SMILES           "OpenEye OEToolkits" 2.0.7 "COc1ccncc1C(=O)N2CCN(C(C2)C(=O)NCc3cccs3)c4ccc(c(c4)Cl)Cl"                                                                                                                             
# 
_pdbx_chem_comp_identifier.comp_id           KKO 
_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        "(2~{S})-1-(3,4-dichlorophenyl)-4-(4-methoxypyridin-3-yl)carbonyl-~{N}-(thiophen-2-ylmethyl)piperazine-2-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 
KKO "Create component" 2023-08-15 PDBE 
KKO "Initial release"  2023-12-06 RCSB 
# 
