data_A1A3O
# 
_chem_comp.id                                    A1A3O 
_chem_comp.name                                  "[(4R)-imidazo[1,5-a]pyridin-8-yl]{4-[(1M)-3'-nitro[1,1'-biphenyl]-2-yl]piperazin-1-yl}methanone" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C24 H21 N5 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2024-08-29 
_chem_comp.pdbx_modified_date                    2025-09-05 
_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                        427.455 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     A1A3O 
_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        9DDG 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
_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 
A1A3O C4   C1  C 0  1 Y N N N N N 9.721  2.925  26.260 4.073  -2.468 -0.754 C4   A1A3O 1  
A1A3O C5   C2  C 0  1 Y N N N N N 11.898 4.829  25.360 2.348  0.654  -1.366 C5   A1A3O 2  
A1A3O C6   C3  C 0  1 Y N N N N N 8.841  1.123  24.283 1.607  -3.420 0.098  C6   A1A3O 3  
A1A3O C7   C4  C 0  1 Y N N N N N 14.277 4.866  24.827 3.664  2.609  -0.939 C7   A1A3O 4  
A1A3O C8   C5  C 0  1 Y N N N N N 12.983 2.813  24.546 4.377  0.493  -0.074 C8   A1A3O 5  
A1A3O C10  C6  C 0  1 Y N N N N N 9.372  -1.508 15.934 -6.363 2.177  -0.938 C10  A1A3O 6  
A1A3O C13  C7  C 0  1 Y N N N N N 10.053 1.832  24.081 1.801  -2.054 -0.050 C13  A1A3O 7  
A1A3O C15  C8  C 0  1 Y N N N N N 10.475 -0.191 17.337 -4.854 0.962  0.099  C15  A1A3O 8  
A1A3O C17  C9  C 0  1 Y N N N N N 12.672 -0.683 18.220 -4.528 -1.448 -0.180 C17  A1A3O 9  
A1A3O C20  C10 C 0  1 N N N N N N 11.589 1.493  18.845 -3.029 -0.258 1.410  C20  A1A3O 10 
A1A3O C21  C11 C 0  1 N N N N N N 10.461 0.459  22.107 -0.394 -1.430 -0.653 C21  A1A3O 11 
A1A3O C22  C12 C 0  1 N N N N N N 10.836 2.899  22.087 0.378  -1.213 1.635  C22  A1A3O 12 
A1A3O C24  C13 C 0  1 N N N N N N 11.850 2.743  20.948 -0.637 -0.102 1.925  C24  A1A3O 13 
A1A3O C1   C14 C 0  1 Y N N N N N 8.525  2.217  26.432 3.869  -3.824 -0.592 C1   A1A3O 14 
A1A3O C2   C15 C 0  1 Y N N N N N 8.088  1.316  25.453 2.640  -4.298 -0.168 C2   A1A3O 15 
A1A3O C3   C16 C 0  1 Y N N N N N 13.119 5.526  25.268 2.554  2.012  -1.508 C3   A1A3O 16 
A1A3O C9   C17 C 0  1 Y N N N N N 9.254  0.359  17.047 -4.746 2.261  0.497  C9   A1A3O 17 
A1A3O C11  C18 C 0  1 Y N N N N N 11.813 3.469  24.993 3.260  -0.114 -0.645 C11  A1A3O 18 
A1A3O C12  C19 C 0  1 Y N N N N N 10.517 2.741  25.101 3.041  -1.572 -0.485 C12  A1A3O 19 
A1A3O C14  C20 C 0  1 Y N N N N N 14.214 3.503  24.468 4.575  1.850  -0.226 C14  A1A3O 20 
A1A3O C16  C21 C 0  1 Y N N N N N 12.694 -1.889 17.464 -5.585 -1.423 -1.098 C16  A1A3O 21 
A1A3O C18  C22 C 0  1 Y N N N N N 11.624 -2.222 16.658 -6.231 -0.277 -1.396 C18  A1A3O 22 
A1A3O C23  C23 C 0  1 N N N N N N 11.546 0.253  21.018 -1.440 -0.328 -0.457 C23  A1A3O 23 
A1A3O C19  C24 C 0  1 Y N N N N N 11.582 0.168  18.142 -4.136 -0.270 0.439  C19  A1A3O 24 
A1A3O N25  N1  N 0  1 Y N N N N N 8.548  -0.472 16.185 -5.676 2.966  -0.153 N25  A1A3O 25 
A1A3O N26  N2  N 0  1 Y N N N N N 10.546 -1.388 16.619 -5.887 0.911  -0.817 N26  A1A3O 26 
A1A3O N27  N3  N 0  1 N N N N N N 10.789 1.665  22.871 0.759  -1.166 0.218  N27  A1A3O 27 
A1A3O N28  N4  N 0  1 N N N N N N 11.680 1.480  20.201 -1.753 -0.230 0.976  N28  A1A3O 28 
A1A3O N29  N5  N 1  1 N N N N N N 15.428 2.799  24.010 5.762  2.496  0.379  N29  A1A3O 29 
A1A3O O31  O1  O 0  1 N N N N N N 11.550 2.530  18.184 -3.267 -0.272 2.602  O31  A1A3O 30 
A1A3O O30  O2  O -1 1 N N N N N N 16.479 3.433  23.991 6.562  1.829  1.011  O30  A1A3O 31 
A1A3O O32  O3  O 0  1 N N N N N N 15.312 1.621  23.676 5.937  3.693  0.246  O32  A1A3O 32 
A1A3O HC4  H1  H 0  1 N N N N N N 10.042 3.621  27.021 5.033  -2.102 -1.086 HC4  A1A3O 33 
A1A3O HC5  H2  H 0  1 N N N N N N 11.017 5.342  25.716 1.481  0.189  -1.811 HC5  A1A3O 34 
A1A3O HC6  H3  H 0  1 N N N N N N 8.494  0.429  23.531 0.650  -3.797 0.428  HC6  A1A3O 35 
A1A3O HC7  H4  H 0  1 N N N N N N 15.213 5.400  24.763 3.821  3.671  -1.052 HC7  A1A3O 36 
A1A3O HC8  H5  H 0  1 N N N N N N 12.935 1.772  24.261 5.087  -0.098 0.486  HC8  A1A3O 37 
A1A3O HC10 H6  H 0  0 N N N N N N 9.134  -2.329 15.274 -7.179 2.482  -1.576 HC10 A1A3O 38 
A1A3O HC17 H7  H 0  0 N N N N N N 13.508 -0.431 18.856 -4.024 -2.376 0.045  HC17 A1A3O 39 
A1A3O H211 H8  H 0  0 N N N N N N 9.476  0.578  21.631 -0.830 -2.395 -0.397 H211 A1A3O 40 
A1A3O H212 H9  H 0  0 N N N N N N 10.441 -0.411 22.779 -0.069 -1.442 -1.694 H212 A1A3O 41 
A1A3O H221 H10 H 0  0 N N N N N N 11.139 3.734  22.736 1.263  -1.068 2.255  H221 A1A3O 42 
A1A3O H222 H11 H 0  0 N N N N N N 9.841  3.104  21.666 -0.068 -2.182 1.860  H222 A1A3O 43 
A1A3O H242 H12 H 0  0 N N N N N N 12.864 2.766  21.374 -1.009 -0.203 2.945  H242 A1A3O 44 
A1A3O H241 H13 H 0  0 N N N N N N 11.727 3.584  20.250 -0.160 0.870  1.804  H241 A1A3O 45 
A1A3O HC1  H14 H 0  1 N N N N N N 7.936  2.367  27.325 4.671  -4.517 -0.797 HC1  A1A3O 46 
A1A3O HC2  H15 H 0  1 N N N N N N 7.169  0.768  25.598 2.488  -5.360 -0.043 HC2  A1A3O 47 
A1A3O HC3  H16 H 0  1 N N N N N N 13.164 6.571  25.537 1.846  2.609  -2.063 HC3  A1A3O 48 
A1A3O HC9  H17 H 0  1 N N N N N N 8.893  1.301  17.432 -4.035 2.650  1.211  HC9  A1A3O 49 
A1A3O HC16 H18 H 0  0 N N N N N N 13.550 -2.545 17.521 -5.891 -2.342 -1.578 HC16 A1A3O 50 
A1A3O HC18 H19 H 0  0 N N N N N N 11.640 -3.127 16.069 -7.041 -0.300 -2.111 HC18 A1A3O 51 
A1A3O H232 H20 H 0  0 N N N N N N 11.257 -0.587 20.369 -1.041 0.623  -0.811 H232 A1A3O 52 
A1A3O H231 H21 H 0  0 N N N N N N 12.509 0.029  21.500 -2.343 -0.576 -1.016 H231 A1A3O 53 
# 
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 
A1A3O C10 N25  DOUB Y N 1  
A1A3O C10 N26  SING Y N 2  
A1A3O N25 C9   SING Y N 3  
A1A3O N26 C18  SING Y N 4  
A1A3O N26 C15  SING Y N 5  
A1A3O C18 C16  DOUB Y N 6  
A1A3O C9  C15  DOUB Y N 7  
A1A3O C15 C19  SING Y N 8  
A1A3O C16 C17  SING Y N 9  
A1A3O C19 C17  DOUB Y N 10 
A1A3O C19 C20  SING N N 11 
A1A3O O31 C20  DOUB N N 12 
A1A3O C20 N28  SING N N 13 
A1A3O N28 C24  SING N N 14 
A1A3O N28 C23  SING N N 15 
A1A3O C24 C22  SING N N 16 
A1A3O C23 C21  SING N N 17 
A1A3O C22 N27  SING N N 18 
A1A3O C21 N27  SING N N 19 
A1A3O N27 C13  SING N N 20 
A1A3O O32 N29  DOUB N N 21 
A1A3O O30 N29  SING N N 22 
A1A3O N29 C14  SING N N 23 
A1A3O C13 C6   DOUB Y N 24 
A1A3O C13 C12  SING Y N 25 
A1A3O C6  C2   SING Y N 26 
A1A3O C14 C8   DOUB Y N 27 
A1A3O C14 C7   SING Y N 28 
A1A3O C8  C11  SING Y N 29 
A1A3O C7  C3   DOUB Y N 30 
A1A3O C11 C12  SING N N 31 
A1A3O C11 C5   DOUB Y N 32 
A1A3O C12 C4   DOUB Y N 33 
A1A3O C3  C5   SING Y N 34 
A1A3O C2  C1   DOUB Y N 35 
A1A3O C4  C1   SING Y N 36 
A1A3O C4  HC4  SING N N 37 
A1A3O C5  HC5  SING N N 38 
A1A3O C6  HC6  SING N N 39 
A1A3O C7  HC7  SING N N 40 
A1A3O C8  HC8  SING N N 41 
A1A3O C10 HC10 SING N N 42 
A1A3O C17 HC17 SING N N 43 
A1A3O C21 H211 SING N N 44 
A1A3O C21 H212 SING N N 45 
A1A3O C22 H221 SING N N 46 
A1A3O C22 H222 SING N N 47 
A1A3O C24 H242 SING N N 48 
A1A3O C24 H241 SING N N 49 
A1A3O C1  HC1  SING N N 50 
A1A3O C2  HC2  SING N N 51 
A1A3O C3  HC3  SING N N 52 
A1A3O C9  HC9  SING N N 53 
A1A3O C16 HC16 SING N N 54 
A1A3O C18 HC18 SING N N 55 
A1A3O C23 H232 SING N N 56 
A1A3O C23 H231 SING N N 57 
# 
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 
A1A3O SMILES           ACDLabs              14.52 "O=C(c1cccn2cncc21)N1CCN(CC1)c1ccccc1c1cccc(c1)[N+]([O-])=O"                                                                                      
A1A3O InChI            InChI                1.06  "InChI=1S/C24H21N5O3/c30-24(21-8-4-10-28-17-25-16-23(21)28)27-13-11-26(12-14-27)22-9-2-1-7-20(22)18-5-3-6-19(15-18)29(31)32/h1-10,15-17H,11-14H2" 
A1A3O InChIKey         InChI                1.06  RAJYUQUPQDWVAH-UHFFFAOYSA-N                                                                                                                       
A1A3O SMILES_CANONICAL CACTVS               3.385 "[O-][N+](=O)c1cccc(c1)c2ccccc2N3CCN(CC3)C(=O)c4cccn5cncc45"                                                                                      
A1A3O SMILES           CACTVS               3.385 "[O-][N+](=O)c1cccc(c1)c2ccccc2N3CCN(CC3)C(=O)c4cccn5cncc45"                                                                                      
A1A3O SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "c1ccc(c(c1)c2cccc(c2)[N+](=O)[O-])N3CCN(CC3)C(=O)c4cccn5c4cnc5"                                                                                  
A1A3O SMILES           "OpenEye OEToolkits" 2.0.7 "c1ccc(c(c1)c2cccc(c2)[N+](=O)[O-])N3CCN(CC3)C(=O)c4cccn5c4cnc5"                                                                                  
# 
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 
A1A3O "SYSTEMATIC NAME" ACDLabs              14.52 "[(4R)-imidazo[1,5-a]pyridin-8-yl]{4-[(1M)-3'-nitro[1,1'-biphenyl]-2-yl]piperazin-1-yl}methanone" 
A1A3O "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.7 "imidazo[1,5-a]pyridin-8-yl-[4-[2-(3-nitrophenyl)phenyl]piperazin-1-yl]methanone"                 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
A1A3O "Create component" 2024-08-29 RCSB 
A1A3O "Initial release"  2025-09-10 RCSB 
# 
