data_XN4
# 
_chem_comp.id                                    XN4 
_chem_comp.name                                  "(5S)-5-butyl-4-({1-[(4-chlorophenyl)methyl]-1H-imidazol-5-yl}methyl)-1-[3-(trifluoromethoxy)phenyl]piperazin-2-one" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C26 H28 Cl F3 N4 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2020-12-21 
_chem_comp.pdbx_modified_date                    2022-11-04 
_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                        520.974 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     XN4 
_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        7L46 
_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 
XN4 C10  C1  C  0 1 Y N N 29.913 -38.510 -6.159 5.188  -1.836 0.001  C10  XN4 1  
XN4 C21  C2  C  0 1 N N N 34.641 -36.087 -2.981 -0.297 -3.075 1.329  C21  XN4 2  
XN4 C24  C3  C  0 1 Y N N 36.336 -33.241 -4.442 -2.535 -1.093 1.544  C24  XN4 3  
XN4 C01  C4  C  0 1 N N N 37.484 -38.558 -8.446 -4.683 -4.386 -3.287 C01  XN4 4  
XN4 C02  C5  C  0 1 N N N 36.841 -38.793 -7.048 -3.544 -3.365 -3.344 C02  XN4 5  
XN4 C03  C6  C  0 1 N N N 35.723 -37.769 -6.724 -2.622 -3.562 -2.138 C03  XN4 6  
XN4 C04  C7  C  0 1 N N N 35.812 -37.183 -5.287 -1.484 -2.542 -2.195 C04  XN4 7  
XN4 C05  C8  C  0 1 N N S 35.031 -35.822 -5.229 -0.495 -2.816 -1.061 C05  XN4 8  
XN4 C06  C9  C  0 1 N N N 33.686 -36.227 -5.702 0.683  -1.852 -1.163 C06  XN4 9  
XN4 C08  C10 C  0 1 Y N N 31.387 -36.980 -5.024 2.819  -1.450 -0.016 C08  XN4 10 
XN4 C09  C11 C  0 1 Y N N 31.224 -38.114 -5.786 3.897  -2.324 0.051  C09  XN4 11 
XN4 C11  C12 C  0 1 Y N N 28.822 -37.776 -5.765 5.411  -0.477 -0.117 C11  XN4 12 
XN4 C12  C13 C  0 1 Y N N 28.971 -36.638 -5.003 4.338  0.401  -0.184 C12  XN4 13 
XN4 C14  C14 C  0 1 N N N 26.541 -36.242 -4.977 5.921  2.168  -0.344 C14  XN4 14 
XN4 C18  C15 C  0 1 Y N N 30.292 -36.240 -4.639 3.041  -0.086 -0.133 C18  XN4 15 
XN4 C19  C16 C  0 1 N N N 33.160 -36.575 -3.228 1.076  -2.483 1.180  C19  XN4 16 
XN4 C23  C17 C  0 1 N N N 36.037 -34.501 -3.585 -1.539 -1.205 0.418  C23  XN4 17 
XN4 C25  C18 C  0 1 Y N N 37.045 -33.212 -5.633 -3.379 -2.053 1.967  C25  XN4 18 
XN4 C27  C19 C  0 1 Y N N 36.459 -31.220 -5.173 -3.720 -0.327 3.217  C27  XN4 19 
XN4 C29  C20 C  0 1 N N N 35.211 -31.457 -3.007 -2.055 1.288  2.250  C29  XN4 20 
XN4 C30  C21 C  0 1 Y N N 33.684 -31.807 -2.969 -2.724 2.153  1.214  C30  XN4 21 
XN4 C31  C22 C  0 1 Y N N 32.833 -31.475 -4.026 -2.327 2.080  -0.108 C31  XN4 22 
XN4 C32  C23 C  0 1 Y N N 31.471 -31.790 -3.983 -2.941 2.873  -1.060 C32  XN4 23 
XN4 C33  C24 C  0 1 Y N N 30.955 -32.433 -2.860 -3.953 3.740  -0.688 C33  XN4 24 
XN4 C35  C25 C  0 1 Y N N 31.786 -32.749 -1.780 -4.351 3.812  0.635  C35  XN4 25 
XN4 C36  C26 C  0 1 Y N N 33.143 -32.431 -1.845 -3.740 3.015  1.584  C36  XN4 26 
XN4 F15  F1  F  0 1 N N N 26.377 -36.331 -6.344 5.966  3.561  -0.463 F15  XN4 27 
XN4 F16  F2  F  0 1 N N N 25.681 -35.294 -4.539 6.558  1.586  -1.446 F16  XN4 28 
XN4 F17  F3  F  0 1 N N N 26.214 -37.454 -4.400 6.573  1.778  0.831  F17  XN4 29 
XN4 N07  N1  N  0 1 N N N 32.707 -36.588 -4.658 1.511  -1.945 0.035  N07  XN4 30 
XN4 N22  N2  N  0 1 N N N 34.991 -35.214 -3.942 -1.162 -2.613 0.235  N22  XN4 31 
XN4 N26  N3  N  0 1 Y N N 37.125 -31.966 -6.074 -4.091 -1.558 2.990  N26  XN4 32 
XN4 N28  N4  N  0 1 Y N N 35.974 -31.959 -4.190 -2.750 0.002  2.337  N28  XN4 33 
XN4 O13  O1  O  0 1 N N N 27.855 -35.863 -4.589 4.559  1.737  -0.299 O13  XN4 34 
XN4 O20  O2  O  0 1 N N N 32.428 -36.839 -2.325 1.820  -2.492 2.137  O20  XN4 35 
XN4 CL34 CL1 CL 0 0 N N N 29.203 -32.859 -2.809 -4.725 4.736  -1.883 CL34 XN4 36 
XN4 H1   H1  H  0 1 N N N 29.773 -39.397 -6.759 6.024  -2.516 0.057  H1   XN4 37 
XN4 H2   H2  H  0 1 N N N 35.321 -36.951 -3.005 -0.227 -4.162 1.300  H2   XN4 38 
XN4 H3   H3  H  0 1 N N N 34.707 -35.597 -1.999 -0.723 -2.765 2.283  H3   XN4 39 
XN4 H4   H4  H  0 1 N N N 38.267 -39.310 -8.621 -5.339 -4.246 -4.146 H4   XN4 40 
XN4 H5   H5  H  0 1 N N N 36.711 -38.645 -9.224 -4.269 -5.394 -3.306 H5   XN4 41 
XN4 H6   H6  H  0 1 N N N 37.928 -37.552 -8.481 -5.252 -4.244 -2.368 H6   XN4 42 
XN4 H7   H7  H  0 1 N N N 36.409 -39.804 -7.025 -2.975 -3.507 -4.263 H7   XN4 43 
XN4 H8   H8  H  0 1 N N N 37.626 -38.712 -6.282 -3.958 -2.357 -3.325 H8   XN4 44 
XN4 H9   H9  H  0 1 N N N 35.793 -36.939 -7.443 -3.191 -3.420 -1.219 H9   XN4 45 
XN4 H10  H10 H  0 1 N N N 34.750 -38.270 -6.835 -2.208 -4.570 -2.158 H10  XN4 46 
XN4 H11  H11 H  0 1 N N N 35.367 -37.892 -4.573 -0.970 -2.624 -3.153 H11  XN4 47 
XN4 H12  H12 H  0 1 N N N 36.867 -37.012 -5.025 -1.891 -1.536 -2.087 H12  XN4 48 
XN4 H13  H13 H  0 1 N N N 35.483 -35.135 -5.959 -0.136 -3.843 -1.130 H13  XN4 49 
XN4 H14  H14 H  0 1 N N N 33.267 -35.389 -6.279 1.284  -2.106 -2.037 H14  XN4 50 
XN4 H15  H15 H  0 1 N N N 33.811 -37.099 -6.360 0.308  -0.833 -1.268 H15  XN4 51 
XN4 H16  H16 H  0 1 N N N 32.081 -38.694 -6.096 3.725  -3.387 0.142  H16  XN4 52 
XN4 H17  H17 H  0 1 N N N 27.832 -38.095 -6.057 6.421  -0.098 -0.156 H17  XN4 53 
XN4 H18  H18 H  0 1 N N N 30.435 -35.344 -4.052 2.205  0.596  -0.185 H18  XN4 54 
XN4 H19  H19 H  0 1 N N N 36.920 -35.155 -3.631 -1.986 -0.826 -0.501 H19  XN4 55 
XN4 H20  H20 H  0 1 N N N 35.879 -34.171 -2.548 -0.651 -0.619 0.658  H20  XN4 56 
XN4 H21  H21 H  0 1 N N N 37.468 -34.075 -6.126 -3.468 -3.047 1.554  H21  XN4 57 
XN4 H22  H22 H  0 1 N N N 36.336 -30.149 -5.244 -4.121 0.320  3.983  H22  XN4 58 
XN4 H23  H23 H  0 1 N N N 35.675 -31.881 -2.104 -1.015 1.121  1.967  H23  XN4 59 
XN4 H24  H24 H  0 1 N N N 35.305 -30.361 -2.988 -2.092 1.787  3.219  H24  XN4 60 
XN4 H25  H25 H  0 1 N N N 33.233 -30.967 -4.891 -1.536 1.403  -0.398 H25  XN4 61 
XN4 H26  H26 H  0 1 N N N 30.826 -31.537 -4.812 -2.630 2.816  -2.092 H26  XN4 62 
XN4 H27  H27 H  0 1 N N N 31.381 -33.234 -0.904 -5.141 4.489  0.925  H27  XN4 63 
XN4 H28  H28 H  0 1 N N N 33.785 -32.672 -1.011 -4.053 3.068  2.616  H28  XN4 64 
# 
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 
XN4 C01 C02  SING N N 1  
XN4 C02 C03  SING N N 2  
XN4 C03 C04  SING N N 3  
XN4 F15 C14  SING N N 4  
XN4 C10 C09  DOUB Y N 5  
XN4 C10 C11  SING Y N 6  
XN4 N26 C25  SING Y N 7  
XN4 N26 C27  DOUB Y N 8  
XN4 C09 C08  SING Y N 9  
XN4 C11 C12  DOUB Y N 10 
XN4 C06 C05  SING N N 11 
XN4 C06 N07  SING N N 12 
XN4 C25 C24  DOUB Y N 13 
XN4 C04 C05  SING N N 14 
XN4 C05 N22  SING N N 15 
XN4 C27 N28  SING Y N 16 
XN4 C08 N07  SING N N 17 
XN4 C08 C18  DOUB Y N 18 
XN4 C12 C18  SING Y N 19 
XN4 C12 O13  SING N N 20 
XN4 C14 O13  SING N N 21 
XN4 C14 F16  SING N N 22 
XN4 C14 F17  SING N N 23 
XN4 N07 C19  SING N N 24 
XN4 C24 N28  SING Y N 25 
XN4 C24 C23  SING N N 26 
XN4 N28 C29  SING N N 27 
XN4 C31 C32  DOUB Y N 28 
XN4 C31 C30  SING Y N 29 
XN4 C32 C33  SING Y N 30 
XN4 N22 C23  SING N N 31 
XN4 N22 C21  SING N N 32 
XN4 C19 C21  SING N N 33 
XN4 C19 O20  DOUB N N 34 
XN4 C29 C30  SING N N 35 
XN4 C30 C36  DOUB Y N 36 
XN4 C33 CL34 SING N N 37 
XN4 C33 C35  DOUB Y N 38 
XN4 C36 C35  SING Y N 39 
XN4 C10 H1   SING N N 40 
XN4 C21 H2   SING N N 41 
XN4 C21 H3   SING N N 42 
XN4 C01 H4   SING N N 43 
XN4 C01 H5   SING N N 44 
XN4 C01 H6   SING N N 45 
XN4 C02 H7   SING N N 46 
XN4 C02 H8   SING N N 47 
XN4 C03 H9   SING N N 48 
XN4 C03 H10  SING N N 49 
XN4 C04 H11  SING N N 50 
XN4 C04 H12  SING N N 51 
XN4 C05 H13  SING N N 52 
XN4 C06 H14  SING N N 53 
XN4 C06 H15  SING N N 54 
XN4 C09 H16  SING N N 55 
XN4 C11 H17  SING N N 56 
XN4 C18 H18  SING N N 57 
XN4 C23 H19  SING N N 58 
XN4 C23 H20  SING N N 59 
XN4 C25 H21  SING N N 60 
XN4 C27 H22  SING N N 61 
XN4 C29 H23  SING N N 62 
XN4 C29 H24  SING N N 63 
XN4 C31 H25  SING N N 64 
XN4 C32 H26  SING N N 65 
XN4 C35 H27  SING N N 66 
XN4 C36 H28  SING N N 67 
# 
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 
XN4 SMILES           ACDLabs              12.01 "c4cc(N1CC(CCCC)N(CC1=O)Cc2n(cnc2)Cc3ccc(cc3)Cl)cc(c4)OC(F)(F)F"                                                                                                                      
XN4 InChI            InChI                1.03  "InChI=1S/C26H28ClF3N4O2/c1-2-3-5-22-16-34(21-6-4-7-24(12-21)36-26(28,29)30)25(35)17-32(22)15-23-13-31-18-33(23)14-19-8-10-20(27)11-9-19/h4,6-13,18,22H,2-3,5,14-17H2,1H3/t22-/m0/s1" 
XN4 InChIKey         InChI                1.03  POBHWQSJZMJUAH-QFIPXVFZSA-N                                                                                                                                                           
XN4 SMILES_CANONICAL CACTVS               3.385 "CCCC[C@H]1CN(C(=O)CN1Cc2cncn2Cc3ccc(Cl)cc3)c4cccc(OC(F)(F)F)c4"                                                                                                                      
XN4 SMILES           CACTVS               3.385 "CCCC[CH]1CN(C(=O)CN1Cc2cncn2Cc3ccc(Cl)cc3)c4cccc(OC(F)(F)F)c4"                                                                                                                       
XN4 SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "CCCC[C@H]1CN(C(=O)CN1Cc2cncn2Cc3ccc(cc3)Cl)c4cccc(c4)OC(F)(F)F"                                                                                                                      
XN4 SMILES           "OpenEye OEToolkits" 2.0.7 "CCCCC1CN(C(=O)CN1Cc2cncn2Cc3ccc(cc3)Cl)c4cccc(c4)OC(F)(F)F"                                                                                                                          
# 
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 
XN4 "SYSTEMATIC NAME" ACDLabs              12.01 "(5S)-5-butyl-4-({1-[(4-chlorophenyl)methyl]-1H-imidazol-5-yl}methyl)-1-[3-(trifluoromethoxy)phenyl]piperazin-2-one"  
XN4 "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.7 "(5~{S})-5-butyl-4-[[3-[(4-chlorophenyl)methyl]imidazol-4-yl]methyl]-1-[3-(trifluoromethyloxy)phenyl]piperazin-2-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 
XN4 "Create component" 2020-12-21 RCSB 
XN4 "Initial release"  2022-11-09 RCSB 
# 
