data_XU3 # _chem_comp.id XU3 _chem_comp.name "(2S,4R)-4-(2-chlorophenyl)sulfonyl-1-[1-(5-chlorothiophen-2-yl)cyclopropyl]carbonyl-N-[1-(iminomethyl)cyclopropyl]pyrrolidine-2-carboxamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C23 H23 Cl2 N3 O4 S2" _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 540.482 _chem_comp.one_letter_code ? _chem_comp.three_letter_code XU3 _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 2XU3 _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 XU3 N1 N1 N 0 1 N N N 20.589 6.645 7.601 -0.708 1.284 -0.124 N1 XU3 1 XU3 C2 C2 C 0 1 N N N 20.822 5.417 8.408 -0.784 -0.093 -0.645 C2 XU3 2 XU3 CL2 CL2 CL 0 0 N N N 19.430 1.182 9.679 2.910 -2.031 -2.277 CL2 XU3 3 XU3 C3 C3 C 0 1 N N R 19.552 4.505 8.284 0.622 -0.692 -0.391 C3 XU3 4 XU3 CL3 CL3 CL 0 0 N N N 22.030 9.903 13.190 -5.655 -2.433 1.332 CL3 XU3 5 XU3 C4 C4 C 0 1 N N N 18.506 5.443 7.617 0.988 -0.058 0.977 C4 XU3 6 XU3 C5 C5 C 0 1 N N S 19.335 6.503 6.883 0.357 1.347 0.887 C5 XU3 7 XU3 S6 S6 S 0 1 N N N 19.719 3.014 7.230 0.547 -2.500 -0.273 S6 XU3 8 XU3 C7 C7 C 0 1 N N N 18.548 7.777 6.867 1.401 2.352 0.470 C7 XU3 9 XU3 C8 C8 C 0 1 Y N N 21.131 2.162 7.888 2.188 -2.981 0.154 C8 XU3 10 XU3 O9 O9 O 0 1 N N N 18.521 2.209 7.277 -0.235 -2.895 0.846 O9 XU3 11 XU3 O10 O10 O 0 1 N N N 20.242 3.452 5.977 0.336 -3.076 -1.554 O10 XU3 12 XU3 C11 C11 C 0 1 Y N N 20.998 1.345 8.979 3.225 -2.770 -0.738 C11 XU3 13 XU3 C12 C12 C 0 1 Y N N 22.107 0.681 9.480 4.513 -3.147 -0.402 C12 XU3 14 XU3 C13 C13 C 0 1 Y N N 23.352 0.829 8.885 4.763 -3.736 0.823 C13 XU3 15 XU3 C14 C14 C 0 1 Y N N 23.491 1.654 7.785 3.727 -3.946 1.714 C14 XU3 16 XU3 C15 C15 C 0 1 Y N N 22.377 2.320 7.290 2.440 -3.564 1.381 C15 XU3 17 XU3 O16 O16 O 0 1 N N N 18.351 8.417 7.894 1.275 2.961 -0.571 O16 XU3 18 XU3 N17 N17 N 0 1 N N N 18.046 8.127 5.670 2.474 2.573 1.255 N17 XU3 19 XU3 C18 C18 C 0 1 N N N 17.211 9.292 5.532 3.489 3.549 0.850 C18 XU3 20 XU3 C19 C19 C 0 1 N N N 15.759 8.933 5.585 2.971 4.754 0.107 C19 XU3 21 XU3 N20 N20 N 0 1 N N N 14.900 9.691 5.376 1.764 5.141 0.278 N20 XU3 22 XU3 C21 C21 C 0 1 N N N 17.718 10.602 6.139 4.685 3.753 1.782 C21 XU3 23 XU3 C22 C22 C 0 1 N N N 17.763 10.394 4.629 4.866 3.013 0.454 C22 XU3 24 XU3 C24 C24 C 0 1 N N N 21.400 7.718 7.426 -1.482 2.316 -0.515 C24 XU3 25 XU3 C25 C25 C 0 1 N N N 22.716 7.771 8.138 -2.939 2.088 -0.828 C25 XU3 26 XU3 O26 O26 O 0 1 N N N 21.084 8.655 6.694 -1.007 3.427 -0.616 O26 XU3 27 XU3 C27 C27 C 0 1 Y N N 22.655 7.957 9.612 -3.488 0.744 -0.425 C27 XU3 28 XU3 C28 C28 C 0 1 Y N N 23.032 7.126 10.579 -3.072 -0.430 -0.901 C28 XU3 29 XU3 C29 C29 C 0 1 Y N N 22.867 7.634 11.856 -3.726 -1.535 -0.382 C29 XU3 30 XU3 C30 C30 C 0 1 Y N N 22.395 8.886 11.857 -4.674 -1.257 0.516 C30 XU3 31 XU3 S31 S31 S 0 1 Y N N 22.116 9.481 10.256 -4.770 0.484 0.751 S31 XU3 32 XU3 C33 C33 C 0 1 N N N 23.907 6.984 7.570 -3.878 3.292 -0.733 C33 XU3 33 XU3 C34 C34 C 0 1 N N N 23.810 8.507 7.382 -3.496 2.726 -2.102 C34 XU3 34 XU3 H2 H2 H 0 1 N N N 21.706 4.882 8.031 -1.543 -0.661 -0.105 H2 XU3 35 XU3 H2A H2A H 0 1 N N N 20.999 5.681 9.461 -1.006 -0.084 -1.712 H2A XU3 36 XU3 H3 H3 H 0 1 N N N 19.306 4.105 9.279 1.324 -0.382 -1.165 H3 XU3 37 XU3 H4 H4 H 0 1 N N N 17.826 5.892 8.356 0.547 -0.627 1.796 H4 XU3 38 XU3 H4A H4A H 0 1 N N N 17.868 4.886 6.915 2.070 0.008 1.094 H4A XU3 39 XU3 H5 H5 H 0 1 N N N 19.554 6.225 5.842 -0.064 1.627 1.853 H5 XU3 40 XU3 H12 H12 H 0 1 N N N 22.001 0.041 10.343 5.322 -2.983 -1.098 H12 XU3 41 XU3 H13 H13 H 0 1 N N N 24.208 0.302 9.280 5.768 -4.031 1.085 H13 XU3 42 XU3 H14 H14 H 0 1 N N N 24.455 1.780 7.315 3.923 -4.406 2.671 H14 XU3 43 XU3 H15 H15 H 0 1 N N N 22.479 2.967 6.432 1.632 -3.725 2.079 H15 XU3 44 XU3 HN17 HN17 H 0 0 N N N 18.255 7.571 4.865 2.575 2.086 2.088 HN17 XU3 45 XU3 H21 H21 H 0 1 N N N 17.203 11.361 6.746 5.097 4.759 1.858 H21 XU3 46 XU3 H21A H21A H 0 0 N N N 18.439 10.885 6.920 4.716 3.162 2.697 H21A XU3 47 XU3 H22 H22 H 0 1 N N N 18.611 10.392 3.929 5.018 1.935 0.496 H22 XU3 48 XU3 H22A H22A H 0 0 N N N 17.407 10.943 3.745 5.399 3.533 -0.343 H22A XU3 49 XU3 H28 H28 H 0 1 N N N 23.432 6.142 10.385 -2.285 -0.513 -1.636 H28 XU3 50 XU3 H29 H29 H 0 1 N N N 23.095 7.080 12.754 -3.488 -2.545 -0.682 H29 XU3 51 XU3 H33 H33 H 0 1 N N N 24.045 6.108 6.919 -4.893 3.112 -0.379 H33 XU3 52 XU3 H33A H33A H 0 0 N N N 24.667 6.360 8.063 -3.442 4.249 -0.444 H33A XU3 53 XU3 H34 H34 H 0 1 N N N 24.463 9.370 7.581 -2.809 3.309 -2.715 H34 XU3 54 XU3 H34A H34A H 0 0 N N N 23.765 9.115 6.467 -4.260 2.173 -2.649 H34A XU3 55 XU3 H19 H19 H 0 1 N N N 15.493 7.915 5.830 3.620 5.291 -0.569 H19 XU3 56 XU3 HN20 HN20 H 0 0 N N N 14.000 9.262 5.460 1.431 5.916 -0.200 HN20 XU3 57 # 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 XU3 C5 N1 SING N N 1 XU3 C24 N1 SING N N 2 XU3 N1 C2 SING N N 3 XU3 H2 C2 SING N N 4 XU3 C3 C2 SING N N 5 XU3 C2 H2A SING N N 6 XU3 C11 CL2 SING N N 7 XU3 S6 C3 SING N N 8 XU3 C4 C3 SING N N 9 XU3 C3 H3 SING N N 10 XU3 C30 CL3 SING N N 11 XU3 C5 C4 SING N N 12 XU3 H4A C4 SING N N 13 XU3 C4 H4 SING N N 14 XU3 H5 C5 SING N N 15 XU3 C7 C5 SING N N 16 XU3 O10 S6 DOUB N N 17 XU3 S6 O9 DOUB N N 18 XU3 S6 C8 SING N N 19 XU3 N17 C7 SING N N 20 XU3 C7 O16 DOUB N N 21 XU3 C15 C8 DOUB Y N 22 XU3 C8 C11 SING Y N 23 XU3 C11 C12 DOUB Y N 24 XU3 C13 C12 SING Y N 25 XU3 C12 H12 SING N N 26 XU3 C14 C13 DOUB Y N 27 XU3 C13 H13 SING N N 28 XU3 C15 C14 SING Y N 29 XU3 H14 C14 SING N N 30 XU3 H15 C15 SING N N 31 XU3 HN17 N17 SING N N 32 XU3 C18 N17 SING N N 33 XU3 C22 C18 SING N N 34 XU3 C18 C19 SING N N 35 XU3 C18 C21 SING N N 36 XU3 N20 C19 DOUB N N 37 XU3 C19 H19 SING N N 38 XU3 N20 HN20 SING N N 39 XU3 C22 C21 SING N N 40 XU3 C21 H21 SING N N 41 XU3 C21 H21A SING N N 42 XU3 H22 C22 SING N N 43 XU3 H22A C22 SING N N 44 XU3 O26 C24 DOUB N N 45 XU3 C24 C25 SING N N 46 XU3 C34 C25 SING N N 47 XU3 C33 C25 SING N N 48 XU3 C25 C27 SING N N 49 XU3 C27 S31 SING Y N 50 XU3 C27 C28 DOUB Y N 51 XU3 H28 C28 SING N N 52 XU3 C28 C29 SING Y N 53 XU3 C29 C30 DOUB Y N 54 XU3 C29 H29 SING N N 55 XU3 S31 C30 SING Y N 56 XU3 H33A C33 SING N N 57 XU3 C34 C33 SING N N 58 XU3 C33 H33 SING N N 59 XU3 H34A C34 SING N N 60 XU3 C34 H34 SING N N 61 # 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 XU3 SMILES ACDLabs 10.04 "Clc1sc(cc1)C5(C(=O)N4C(C(=O)NC2(C=[N@H])CC2)CC(S(=O)(=O)c3ccccc3Cl)C4)CC5" XU3 SMILES_CANONICAL CACTVS 3.352 "Clc1sc(cc1)C2(CC2)C(=O)N3C[C@@H](C[C@H]3C(=O)NC4(CC4)C=N)[S](=O)(=O)c5ccccc5Cl" XU3 SMILES CACTVS 3.352 "Clc1sc(cc1)C2(CC2)C(=O)N3C[CH](C[CH]3C(=O)NC4(CC4)C=N)[S](=O)(=O)c5ccccc5Cl" XU3 SMILES_CANONICAL "OpenEye OEToolkits" 1.6.1 "[H]/N=C/C1(CC1)NC(=O)[C@@H]2C[C@H](CN2C(=O)C3(CC3)c4ccc(s4)Cl)S(=O)(=O)c5ccccc5Cl" XU3 SMILES "OpenEye OEToolkits" 1.6.1 "[H]N=CC1(CC1)NC(=O)C2CC(CN2C(=O)C3(CC3)c4ccc(s4)Cl)S(=O)(=O)c5ccccc5Cl" XU3 InChI InChI 1.03 "InChI=1S/C23H23Cl2N3O4S2/c24-15-3-1-2-4-17(15)34(31,32)14-11-16(20(29)27-22(13-26)7-8-22)28(12-14)21(30)23(9-10-23)18-5-6-19(25)33-18/h1-6,13-14,16,26H,7-12H2,(H,27,29)/b26-13+/t14-,16+/m1/s1" XU3 InChIKey InChI 1.03 UKVPZPACPGTUIO-UPJLJTPPSA-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 XU3 "SYSTEMATIC NAME" ACDLabs 10.04 "(4R)-4-[(2-chlorophenyl)sulfonyl]-1-{[1-(5-chlorothiophen-2-yl)cyclopropyl]carbonyl}-N-{1-[(E)-iminomethyl]cyclopropyl}-L-prolinamide" XU3 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.6.1 "(2S,4R)-4-(2-chlorophenyl)sulfonyl-1-[1-(5-chlorothiophen-2-yl)cyclopropyl]carbonyl-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 XU3 "Create component" 2010-10-15 EBI XU3 "Modify aromatic_flag" 2011-06-04 RCSB XU3 "Modify descriptor" 2011-06-04 RCSB #