data_424
# 
_chem_comp.id                                    424 
_chem_comp.name                                  "(2S,4R)-1-[1-(4-chlorophenyl)cyclopropyl]carbonyl-4-(2-chlorophenyl)sulfonyl-N-[1-(iminomethyl)cyclopropyl]pyrrolidine-2-carboxamide" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C25 H25 Cl2 N3 O4 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2010-10-15 
_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                        534.455 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     424 
_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        2XU1 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
_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 
424 S1   S1   S  0 1 N N N N N N 64.357 4.920  -35.438 -0.352 2.823  1.317  S1   424 1  
424 N2   N2   N  0 1 N N N N N N 66.667 6.398  -33.499 -0.676 -0.962 0.098  N2   424 2  
424 CL2  CL2  CL 0 0 N N N N N N 64.824 4.625  -38.625 2.288  1.904  -0.098 CL2  424 3  
424 C3   C3   C  0 1 N N N N N N 66.805 8.862  -33.308 0.949  -1.975 -1.467 C3   424 4  
424 CL3  CL3  CL 0 0 N N N N N N 71.999 9.637  -36.475 6.091  -2.687 1.557  CL3  424 5  
424 C4   C4   C  0 1 N N R N N N 66.173 5.009  -35.380 -1.097 1.351  0.563  C4   424 6  
424 C5   C5   C  0 1 N N N N N N 66.675 7.479  -32.720 -0.307 -2.030 -0.636 C5   424 7  
424 C6   C6   C  0 1 N N S N N N 66.541 5.023  -32.998 -1.809 -0.916 1.035  C6   424 8  
424 C7   C7   C  0 1 Y N N N N N 63.822 6.129  -36.629 0.294  3.735  -0.045 C7   424 9  
424 C8   C8   C  0 1 N N N N N N 66.722 6.400  -34.973 -0.007 0.352  0.101  C8   424 10 
424 C9   C9   C  0 1 N N N N N N 66.681 4.100  -34.218 -1.860 0.510  1.622  C9   424 11 
424 C10  C10  C  0 1 N N N N N N 67.628 4.649  -32.015 -3.091 -1.215 0.303  C10  424 12 
424 C11  C11  C  0 1 N N N N N N 65.472 9.482  -33.763 0.881  -2.539 -2.888 C11  424 13 
424 C12  C12  C  0 1 N N N N N N 66.187 10.034 -32.532 0.960  -1.027 -2.668 C12  424 14 
424 C13  C13  C  0 1 N N N N N N 68.197 3.679  -29.833 -5.509 -1.517 0.259  C13  424 15 
424 N14  N14  N  0 1 N N N N N N 67.245 4.131  -30.841 -4.262 -1.226 0.971  N14  424 16 
424 C15  C15  C  0 1 N N N N N N 68.330 2.218  -29.873 -5.398 -2.512 -0.867 C15  424 17 
424 N16  N16  N  0 1 N N N N N N 69.099 1.539  -29.082 -4.464 -3.387 -0.858 N16  424 18 
424 C17  C17  C  0 1 Y N N N N N 68.099 9.076  -34.092 2.239  -2.154 -0.709 C17  424 19 
424 O18  O18  O  0 1 N N N N N N 64.005 3.622  -35.909 -1.357 3.668  1.860  O18  424 20 
424 O19  O19  O  0 1 N N N N N N 63.833 5.482  -34.239 0.795  2.468  2.077  O19  424 21 
424 C20  C20  C  0 1 N N N N N N 69.372 4.559  -29.381 -6.804 -1.512 1.073  C20  424 22 
424 C21  C21  C  0 1 N N N N N N 68.140 4.367  -28.470 -6.511 -0.373 0.094  C21  424 23 
424 O22  O22  O  0 1 N N N N N N 66.579 7.285  -31.528 -0.986 -3.035 -0.628 O22  424 24 
424 C23  C23  C  0 1 Y N N N N N 64.030 6.003  -37.988 1.461  3.322  -0.664 C23  424 25 
424 O24  O24  O  0 1 N N N N N N 68.802 4.806  -32.281 -3.071 -1.446 -0.888 O24  424 26 
424 C25  C25  C  0 1 Y N N N N N 68.101 9.453  -35.425 2.212  -2.390 0.653  C25  424 27 
424 C26  C26  C  0 1 Y N N N N N 69.338 8.852  -33.491 3.447  -2.086 -1.376 C26  424 28 
424 C27  C27  C  0 1 Y N N N N N 70.524 9.426  -35.547 4.605  -2.481 0.683  C27  424 29 
424 C29  C29  C  0 1 Y N N N N N 63.181 7.257  -36.169 -0.367 4.861  -0.499 C29  424 30 
424 C30  C30  C  0 1 Y N N N N N 69.286 9.644  -36.131 3.395  -2.554 1.349  C30  424 31 
424 C31  C31  C  0 1 Y N N N N N 70.525 9.030  -34.207 4.631  -2.251 -0.681 C31  424 32 
424 C33  C33  C  0 1 Y N N N N N 63.603 6.968  -38.868 1.967  4.039  -1.733 C33  424 33 
424 C34  C34  C  0 1 Y N N N N N 62.736 8.236  -37.039 0.140  5.577  -1.567 C34  424 34 
424 C35  C35  C  0 1 Y N N N N N 62.962 8.100  -38.399 1.309  5.167  -2.182 C35  424 35 
424 H4   H4   H  0 1 N N N N N N 66.503 4.733  -36.392 -1.750 1.627  -0.265 H4   424 36 
424 H6   H6   H  0 1 N N N N N N 65.577 4.928  -32.476 -1.658 -1.641 1.834  H6   424 37 
424 H8   H8   H  0 1 N N N N N N 66.107 7.209  -35.393 0.828  0.351  0.801  H8   424 38 
424 H8A  H8A  H  0 1 N N N N N N 67.740 6.575  -35.353 0.338  0.604  -0.902 H8A  424 39 
424 H9   H9   H  0 1 N N N N N N 66.076 3.187  -34.115 -1.350 0.548  2.585  H9   424 40 
424 H9A  H9A  H  0 1 N N N N N N 67.704 3.726  -34.369 -2.890 0.852  1.717  H9A  424 41 
424 H11  H11  H  0 1 N N N N N N 65.190 9.967  -34.709 1.769  -3.039 -3.274 H11  424 42 
424 H11A H11A H  0 0 N N N N N N 64.463 9.108  -33.989 -0.072 -2.950 -3.221 H11A 424 43 
424 H12  H12  H  0 1 N N N N N N 65.859 10.107 -31.485 0.060  -0.443 -2.857 H12  424 44 
424 H12A H12A H  0 0 N N N N N N 66.528 11.024 -32.196 1.901  -0.533 -2.910 H12A 424 45 
424 HN14 HN14 H  0 0 N N N N N N 66.267 4.051  -30.648 -4.279 -1.042 1.923  HN14 424 46 
424 H15  H15  H  0 1 N N N N N N 67.752 1.676  -30.607 -6.106 -2.487 -1.682 H15  424 47 
424 HN16 HN16 H  0 0 N N N N N N 69.030 0.563  -29.289 -4.393 -4.028 -1.582 HN16 424 48 
424 H20  H20  H  0 1 N N N N N N 70.435 4.323  -29.222 -7.577 -2.229 0.794  H20  424 49 
424 H20A H20A H  0 0 N N N N N N 69.931 5.412  -29.793 -6.729 -1.293 2.138  H20A 424 50 
424 H21  H21  H  0 1 N N N N N N 67.426 5.097  -28.061 -6.243 0.596  0.515  H21  424 51 
424 H21A H21A H  0 0 N N N N N N 67.966 4.051  -27.431 -7.091 -0.340 -0.828 H21A 424 52 
424 H25  H25  H  0 1 N N N N N N 67.158 9.603  -35.930 1.267  -2.447 1.173  H25  424 53 
424 H26  H26  H  0 1 N N N N N N 69.380 8.537  -32.459 3.467  -1.906 -2.441 H26  424 54 
424 H29  H29  H  0 1 N N N N N N 63.022 7.380  -35.108 -1.279 5.182  -0.019 H29  424 55 
424 H30  H30  H  0 1 N N N N N N 69.239 9.970  -37.159 3.374  -2.738 2.413  H30  424 56 
424 H31  H31  H  0 1 N N N N N N 71.469 8.857  -33.711 5.575  -2.199 -1.202 H31  424 57 
424 H33  H33  H  0 1 N N N N N N 63.768 6.842  -39.928 2.878  3.716  -2.216 H33  424 58 
424 H34  H34  H  0 1 N N N N N N 62.215 9.102  -36.660 -0.377 6.456  -1.922 H34  424 59 
424 H35  H35  H  0 1 N N N N N N 62.641 8.870  -39.085 1.704  5.727  -3.017 H35  424 60 
# 
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 
424 S1  C4   SING N N 1  
424 S1  C7   SING N N 2  
424 S1  O18  DOUB N N 3  
424 S1  O19  DOUB N N 4  
424 N2  C5   SING N N 5  
424 N2  C6   SING N N 6  
424 N2  C8   SING N N 7  
424 CL2 C23  SING N N 8  
424 C3  C5   SING N N 9  
424 C3  C11  SING N N 10 
424 C3  C12  SING N N 11 
424 C3  C17  SING N N 12 
424 CL3 C27  SING N N 13 
424 C4  C8   SING N N 14 
424 C4  C9   SING N N 15 
424 C5  O22  DOUB N N 16 
424 C6  C9   SING N N 17 
424 C6  C10  SING N N 18 
424 C7  C23  DOUB Y N 19 
424 C7  C29  SING Y N 20 
424 C10 N14  SING N N 21 
424 C10 O24  DOUB N N 22 
424 C11 C12  SING N N 23 
424 C13 N14  SING N N 24 
424 C13 C15  SING N N 25 
424 C13 C20  SING N N 26 
424 C13 C21  SING N N 27 
424 C15 N16  DOUB N N 28 
424 C17 C25  DOUB Y N 29 
424 C17 C26  SING Y N 30 
424 C20 C21  SING N N 31 
424 C23 C33  SING Y N 32 
424 C25 C30  SING Y N 33 
424 C26 C31  DOUB Y N 34 
424 C27 C30  DOUB Y N 35 
424 C27 C31  SING Y N 36 
424 C29 C34  DOUB Y N 37 
424 C33 C35  DOUB Y N 38 
424 C34 C35  SING Y N 39 
424 C4  H4   SING N N 40 
424 C6  H6   SING N N 41 
424 C8  H8   SING N N 42 
424 C8  H8A  SING N N 43 
424 C9  H9   SING N N 44 
424 C9  H9A  SING N N 45 
424 C11 H11  SING N N 46 
424 C11 H11A SING N N 47 
424 C12 H12  SING N N 48 
424 C12 H12A SING N N 49 
424 N14 HN14 SING N N 50 
424 C15 H15  SING N N 51 
424 N16 HN16 SING N N 52 
424 C20 H20  SING N N 53 
424 C20 H20A SING N N 54 
424 C21 H21  SING N N 55 
424 C21 H21A SING N N 56 
424 C25 H25  SING N N 57 
424 C26 H26  SING N N 58 
424 C29 H29  SING N N 59 
424 C30 H30  SING N N 60 
424 C31 H31  SING N N 61 
424 C33 H33  SING N N 62 
424 C34 H34  SING N N 63 
424 C35 H35  SING N N 64 
# 
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 
424 SMILES           ACDLabs              10.04 "O=S(=O)(c1ccccc1Cl)C5CC(C(=O)NC2(C=[N@H])CC2)N(C(=O)C4(c3ccc(Cl)cc3)CC4)C5"                                                                                                                        
424 SMILES_CANONICAL CACTVS               3.352 "Clc1ccc(cc1)C2(CC2)C(=O)N3C[C@@H](C[C@H]3C(=O)NC4(CC4)C=N)[S](=O)(=O)c5ccccc5Cl"                                                                                                                   
424 SMILES           CACTVS               3.352 "Clc1ccc(cc1)C2(CC2)C(=O)N3C[CH](C[CH]3C(=O)NC4(CC4)C=N)[S](=O)(=O)c5ccccc5Cl"                                                                                                                      
424 SMILES_CANONICAL "OpenEye OEToolkits" 1.6.1 "[H]/N=C/C1(CC1)NC(=O)[C@@H]2C[C@H](CN2C(=O)C3(CC3)c4ccc(cc4)Cl)S(=O)(=O)c5ccccc5Cl"                                                                                                                
424 SMILES           "OpenEye OEToolkits" 1.6.1 "[H]N=CC1(CC1)NC(=O)C2CC(CN2C(=O)C3(CC3)c4ccc(cc4)Cl)S(=O)(=O)c5ccccc5Cl"                                                                                                                           
424 InChI            InChI                1.03  "InChI=1S/C25H25Cl2N3O4S/c26-17-7-5-16(6-8-17)25(11-12-25)23(32)30-14-18(35(33,34)21-4-2-1-3-19(21)27)13-20(30)22(31)29-24(15-28)9-10-24/h1-8,15,18,20,28H,9-14H2,(H,29,31)/b28-15+/t18-,20+/m1/s1" 
424 InChIKey         InChI                1.03  JSCXGRUVBVSETN-OIRADOGLSA-N                                                                                                                                                                         
# 
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 
424 "SYSTEMATIC NAME" ACDLabs              10.04 "(4R)-1-{[1-(4-chlorophenyl)cyclopropyl]carbonyl}-4-[(2-chlorophenyl)sulfonyl]-N-{1-[(E)-iminomethyl]cyclopropyl}-L-prolinamide"       
424 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.6.1 "(2S,4R)-1-[1-(4-chlorophenyl)cyclopropyl]carbonyl-4-(2-chlorophenyl)sulfonyl-N-[1-(iminomethyl)cyclopropyl]pyrrolidine-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 
424 "Create component"     2010-10-15 EBI  
424 "Modify aromatic_flag" 2011-06-04 RCSB 
424 "Modify descriptor"    2011-06-04 RCSB 
424 "Modify PCM"           2024-09-27 PDBE 
# 
_pdbx_chem_comp_pcm.pcm_id                             1 
_pdbx_chem_comp_pcm.comp_id                            424 
_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               C15 
_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      ? 
# 
