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 2011-06-04 _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 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 # 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 424 S1 S1 S 0 1 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 66.667 6.398 -33.499 -0.676 -0.962 0.098 N2 424 2 424 CL2 CL2 CL 0 0 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 66.805 8.862 -33.308 0.949 -1.975 -1.467 C3 424 4 424 CL3 CL3 CL 0 0 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 66.173 5.009 -35.380 -1.097 1.351 0.563 C4 424 6 424 C5 C5 C 0 1 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 66.541 5.023 -32.998 -1.809 -0.916 1.035 C6 424 8 424 C7 C7 C 0 1 Y 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 66.722 6.400 -34.973 -0.007 0.352 0.101 C8 424 10 424 C9 C9 C 0 1 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 67.628 4.649 -32.015 -3.091 -1.215 0.303 C10 424 12 424 C11 C11 C 0 1 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 66.187 10.034 -32.532 0.960 -1.027 -2.668 C12 424 14 424 C13 C13 C 0 1 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 67.245 4.131 -30.841 -4.262 -1.226 0.971 N14 424 16 424 C15 C15 C 0 1 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 69.099 1.539 -29.082 -4.464 -3.387 -0.858 N16 424 18 424 C17 C17 C 0 1 Y 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 64.005 3.622 -35.909 -1.357 3.668 1.860 O18 424 20 424 O19 O19 O 0 1 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 69.372 4.559 -29.381 -6.804 -1.512 1.073 C20 424 22 424 C21 C21 C 0 1 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 66.579 7.285 -31.528 -0.986 -3.035 -0.628 O22 424 24 424 C23 C23 C 0 1 Y 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 68.802 4.806 -32.281 -3.071 -1.446 -0.888 O24 424 26 424 C25 C25 C 0 1 Y 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 69.338 8.852 -33.491 3.447 -2.086 -1.376 C26 424 28 424 C27 C27 C 0 1 Y 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 63.181 7.257 -36.169 -0.367 4.861 -0.499 C29 424 30 424 C30 C30 C 0 1 Y 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 70.525 9.030 -34.207 4.631 -2.251 -0.681 C31 424 32 424 C33 C33 C 0 1 Y 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 62.736 8.236 -37.039 0.140 5.577 -1.567 C34 424 34 424 C35 C35 C 0 1 Y 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 66.503 4.733 -36.392 -1.750 1.627 -0.265 H4 424 36 424 H6 H6 H 0 1 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 66.107 7.209 -35.393 0.828 0.351 0.801 H8 424 38 424 H8A H8A H 0 1 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 66.076 3.187 -34.115 -1.350 0.548 2.585 H9 424 40 424 H9A H9A H 0 1 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 65.190 9.967 -34.709 1.769 -3.039 -3.274 H11 424 42 424 H11A H11A H 0 0 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 65.859 10.107 -31.485 0.060 -0.443 -2.857 H12 424 44 424 H12A H12A H 0 0 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 66.267 4.051 -30.648 -4.279 -1.042 1.923 HN14 424 46 424 H15 H15 H 0 1 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 69.030 0.563 -29.289 -4.393 -4.028 -1.582 HN16 424 48 424 H20 H20 H 0 1 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 69.931 5.412 -29.793 -6.729 -1.293 2.138 H20A 424 50 424 H21 H21 H 0 1 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 67.966 4.051 -27.431 -7.091 -0.340 -0.828 H21A 424 52 424 H25 H25 H 0 1 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 69.380 8.537 -32.459 3.467 -1.906 -2.441 H26 424 54 424 H29 H29 H 0 1 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 69.239 9.970 -37.159 3.374 -2.738 2.413 H30 424 56 424 H31 H31 H 0 1 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 63.768 6.842 -39.928 2.878 3.716 -2.216 H33 424 58 424 H34 H34 H 0 1 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 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 #