data_A1EDL
# 
_chem_comp.id                                    A1EDL 
_chem_comp.name                                  "4-[6-(2-chloranyl-6-cyclopropyl-phenyl)carbonylimidazo[1,5-a]pyrimidin-8-yl]-2-oxidanyl-benzoic acid" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H16 Cl N3 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "GNE-6468 " 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2024-10-14 
_chem_comp.pdbx_modified_date                    2025-10-10 
_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                        433.844 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     A1EDL 
_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        9JW6 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBC 
_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 
A1EDL C10  C1  C  0 1 N N N N N N 143.322 127.594 117.208 2.455  1.478  -3.371 C10  A1EDL 1  
A1EDL C13  C2  C  0 1 Y N N N N N 139.420 128.200 117.854 3.164  0.701  0.177  C13  A1EDL 2  
A1EDL C15  C3  C  0 1 Y N N N N N 138.383 129.297 117.740 3.254  1.304  1.435  C15  A1EDL 3  
A1EDL C17  C4  C  0 1 Y N N N N N 140.180 130.901 116.632 3.876  3.369  0.394  C17  A1EDL 4  
A1EDL C20  C5  C  0 1 Y N N N N N 138.404 125.723 121.887 -0.472 -2.315 -0.002 C20  A1EDL 5  
A1EDL C21  C6  C  0 1 Y N N N N N 138.580 127.060 122.067 -0.790 -0.942 -0.019 C21  A1EDL 6  
A1EDL C22  C7  C  0 1 Y N N N N N 138.505 127.836 123.375 -2.149 -0.362 -0.060 C22  A1EDL 7  
A1EDL C24  C8  C  0 1 Y N N N N N 138.115 122.973 120.969 0.741  -4.730 0.041  C24  A1EDL 8  
A1EDL C26  C9  C  0 1 Y N N N N N 138.378 127.115 124.708 -3.161 -1.006 -0.781 C26  A1EDL 9  
A1EDL C28  C10 C  0 1 Y N N N N N 138.465 130.166 124.566 -3.693 1.364  0.583  C28  A1EDL 10 
A1EDL C09  C11 C  0 1 N N N N N N 141.848 127.300 117.484 3.352  0.806  -2.330 C09  A1EDL 11 
A1EDL C11  C12 C  0 1 N N N N N N 142.915 126.845 118.475 3.977  1.556  -3.508 C11  A1EDL 12 
A1EDL C12  C13 C  0 1 Y N N N N N 140.829 128.439 117.358 3.441  1.449  -0.970 C12  A1EDL 13 
A1EDL C14  C14 C  0 1 Y N N N N N 141.225 129.782 116.747 3.794  2.777  -0.854 C14  A1EDL 14 
A1EDL C16  C15 C  0 1 N N N N N N 139.055 126.827 118.454 2.785  -0.723 0.061  C16  A1EDL 15 
A1EDL C18  C16 C  0 1 Y N N N N N 138.750 130.652 117.137 3.609  2.634  1.535  C18  A1EDL 16 
A1EDL C19  C17 C  0 1 Y N N N N N 138.830 126.632 119.955 1.373  -1.104 0.034  C19  A1EDL 17 
A1EDL C23  C18 C  0 1 Y N N N N N 138.421 124.072 120.049 1.507  -3.608 0.050  C23  A1EDL 18 
A1EDL C25  C19 C  0 1 Y N N N N N 138.540 129.347 123.298 -2.421 0.823  0.623  C25  A1EDL 19 
A1EDL C27  C20 C  0 1 Y N N N N N 137.952 123.258 122.378 -0.653 -4.610 0.006  C27  A1EDL 20 
A1EDL C29  C21 C  0 1 Y N N N N N 138.302 127.935 125.999 -4.417 -0.477 -0.824 C29  A1EDL 21 
A1EDL C30  C22 C  0 1 Y N N N N N 138.347 129.463 125.912 -4.702 0.715  -0.147 C30  A1EDL 22 
A1EDL C31  C23 C  0 1 N N N N N N 138.272 130.304 127.180 -6.059 1.283  -0.196 C31  A1EDL 23 
A1EDL N06  N1  N  0 1 Y N N N N N 138.558 125.464 120.568 0.896  -2.391 0.032  N06  A1EDL 24 
A1EDL N07  N2  N  0 1 Y N N N N N 138.842 127.621 120.886 0.353  -0.263 0.010  N07  A1EDL 25 
A1EDL N08  N3  N  0 1 Y N N N N N 138.089 124.598 122.857 -1.214 -3.420 -0.017 N08  A1EDL 26 
A1EDL O02  O1  O  0 1 N N N N N N 138.903 125.902 117.744 3.648  -1.579 -0.012 O02  A1EDL 27 
A1EDL O03  O2  O  0 1 N N N N N N 138.501 131.568 124.505 -3.964 2.519  1.240  O03  A1EDL 28 
A1EDL O04  O3  O  0 1 N N N N N N 138.416 131.551 127.097 -6.306 2.315  0.397  O04  A1EDL 29 
A1EDL O05  O4  O  0 1 N N N N N N 138.076 129.752 128.294 -7.026 0.660  -0.897 O05  A1EDL 30 
A1EDL CL01 CL1 CL 0 0 N N N N N N 136.734 129.001 118.324 2.918  0.382  2.867  CL01 A1EDL 31 
A1EDL H1   H1  H  0 1 N N N N N N 143.847 127.064 116.400 1.920  0.832  -4.067 H1   A1EDL 32 
A1EDL H2   H2  H  0 1 N N N N N N 143.699 128.625 117.276 1.929  2.385  -3.073 H2   A1EDL 33 
A1EDL H3   H3  H  0 1 N N N N N N 140.447 131.854 116.200 4.154  4.410  0.477  H3   A1EDL 34 
A1EDL H4   H4  H  0 1 N N N N N N 138.012 121.963 120.600 1.204  -5.706 0.059  H4   A1EDL 35 
A1EDL H5   H5  H  0 1 N N N N N N 138.342 126.036 124.744 -2.946 -1.925 -1.305 H5   A1EDL 36 
A1EDL H6   H6  H  0 1 N N N N N N 141.521 126.445 116.874 3.407  -0.282 -2.340 H6   A1EDL 37 
A1EDL H7   H7  H  0 1 N N N N N N 143.147 125.775 118.580 4.443  0.961  -4.293 H7   A1EDL 38 
A1EDL H8   H8  H  0 1 N N N N N N 143.000 127.336 119.455 4.452  2.515  -3.299 H8   A1EDL 39 
A1EDL H9   H9  H  0 1 N N N N N N 142.234 129.943 116.398 4.004  3.357  -1.741 H9   A1EDL 40 
A1EDL H10  H10 H  0 1 N N N N N N 138.007 131.432 117.066 3.675  3.103  2.505  H10  A1EDL 41 
A1EDL H12  H12 H  0 1 N N N N N N 138.547 123.874 118.995 2.584  -3.680 0.072  H12  A1EDL 42 
A1EDL H13  H13 H  0 1 N N N N N N 138.618 129.839 122.340 -1.640 1.317  1.183  H13  A1EDL 43 
A1EDL H14  H14 H  0 1 N N N N N N 137.727 122.458 123.068 -1.270 -5.496 -0.002 H14  A1EDL 44 
A1EDL H15  H15 H  0 1 N N N N N N 138.218 127.443 126.957 -5.194 -0.979 -1.382 H15  A1EDL 45 
A1EDL H16  H16 H  0 1 N N N N N N 138.481 131.924 125.385 -4.266 2.392  2.150  H16  A1EDL 46 
A1EDL H17  H17 H  0 1 N N N N N N 138.063 130.412 128.977 -7.901 1.071  -0.899 H17  A1EDL 47 
# 
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 
A1EDL C17 C14  DOUB Y N 1  
A1EDL C17 C18  SING Y N 2  
A1EDL C14 C12  SING Y N 3  
A1EDL C18 C15  DOUB Y N 4  
A1EDL C10 C09  SING N N 5  
A1EDL C10 C11  SING N N 6  
A1EDL C12 C09  SING N N 7  
A1EDL C12 C13  DOUB Y N 8  
A1EDL C09 C11  SING N N 9  
A1EDL C15 C13  SING Y N 10 
A1EDL C15 CL01 SING N N 11 
A1EDL O02 C16  DOUB N N 12 
A1EDL C13 C16  SING N N 13 
A1EDL C16 C19  SING N N 14 
A1EDL C19 N06  SING Y N 15 
A1EDL C19 N07  DOUB Y N 16 
A1EDL C23 N06  SING Y N 17 
A1EDL C23 C24  DOUB Y N 18 
A1EDL N06 C20  SING Y N 19 
A1EDL N07 C21  SING Y N 20 
A1EDL C24 C27  SING Y N 21 
A1EDL C20 C21  DOUB Y N 22 
A1EDL C20 N08  SING Y N 23 
A1EDL C21 C22  SING N N 24 
A1EDL C27 N08  DOUB Y N 25 
A1EDL C25 C22  DOUB Y N 26 
A1EDL C25 C28  SING Y N 27 
A1EDL C22 C26  SING Y N 28 
A1EDL O03 C28  SING N N 29 
A1EDL C28 C30  DOUB Y N 30 
A1EDL C26 C29  DOUB Y N 31 
A1EDL C30 C29  SING Y N 32 
A1EDL C30 C31  SING N N 33 
A1EDL O04 C31  DOUB N N 34 
A1EDL C31 O05  SING N N 35 
A1EDL C10 H1   SING N N 36 
A1EDL C10 H2   SING N N 37 
A1EDL C17 H3   SING N N 38 
A1EDL C24 H4   SING N N 39 
A1EDL C26 H5   SING N N 40 
A1EDL C09 H6   SING N N 41 
A1EDL C11 H7   SING N N 42 
A1EDL C11 H8   SING N N 43 
A1EDL C14 H9   SING N N 44 
A1EDL C18 H10  SING N N 45 
A1EDL C23 H12  SING N N 46 
A1EDL C25 H13  SING N N 47 
A1EDL C27 H14  SING N N 48 
A1EDL C29 H15  SING N N 49 
A1EDL O03 H16  SING N N 50 
A1EDL O05 H17  SING N N 51 
# 
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 
A1EDL InChI            InChI                1.06  "InChI=1S/C23H16ClN3O4/c24-16-4-1-3-14(12-5-6-12)18(16)20(29)22-26-19(21-25-9-2-10-27(21)22)13-7-8-15(23(30)31)17(28)11-13/h1-4,7-12,28H,5-6H2,(H,30,31)" 
A1EDL InChIKey         InChI                1.06  GIYKJPISDNWSJD-UHFFFAOYSA-N                                                                                                                               
A1EDL SMILES_CANONICAL CACTVS               3.385 "OC(=O)c1ccc(cc1O)c2nc(n3cccnc23)C(=O)c4c(Cl)cccc4C5CC5"                                                                                                  
A1EDL SMILES           CACTVS               3.385 "OC(=O)c1ccc(cc1O)c2nc(n3cccnc23)C(=O)c4c(Cl)cccc4C5CC5"                                                                                                  
A1EDL SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "c1cc(c(c(c1)Cl)C(=O)c2nc(c3n2cccn3)c4ccc(c(c4)O)C(=O)O)C5CC5"                                                                                            
A1EDL SMILES           "OpenEye OEToolkits" 2.0.7 "c1cc(c(c(c1)Cl)C(=O)c2nc(c3n2cccn3)c4ccc(c(c4)O)C(=O)O)C5CC5"                                                                                            
# 
_pdbx_chem_comp_identifier.comp_id           A1EDL 
_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        "4-[6-(2-chloranyl-6-cyclopropyl-phenyl)carbonylimidazo[1,5-a]pyrimidin-8-yl]-2-oxidanyl-benzoic acid" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
A1EDL "Create component" 2024-10-14 PDBC 
A1EDL "Initial release"  2025-10-15 RCSB 
# 
_pdbx_chem_comp_synonyms.ordinal      1 
_pdbx_chem_comp_synonyms.comp_id      A1EDL 
_pdbx_chem_comp_synonyms.name         "GNE-6468 " 
_pdbx_chem_comp_synonyms.provenance   PUBCHEM 
_pdbx_chem_comp_synonyms.type         ? 
# 
