data_317 # _chem_comp.id 317 _chem_comp.name "(2S,3S)-3-{3-[2-chloro-4-(methylsulfonyl)phenyl]-1,2,4-oxadiazol-5-yl}-1-cyclopentylidene-4-cyclopropyl-1-fluorobutan-2-amine" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C21 H25 Cl F N3 O3 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2008-01-30 _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 453.958 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 317 _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 3C45 _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site RCSB # 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 317 C1 C1 C 0 1 N N S -4.912 63.397 34.786 2.501 -1.055 0.414 C1 317 1 317 C2 C2 C 0 1 N N S -3.611 64.289 35.096 3.342 -0.206 1.369 C2 317 2 317 C3 C3 C 0 1 N N N -2.553 63.529 35.863 3.711 1.091 0.696 C3 317 3 317 C4 C4 C 0 1 N N N -1.948 63.948 37.022 4.954 1.313 0.335 C4 317 4 317 F5 F5 F 0 1 N N N -2.190 62.345 35.348 2.763 2.025 0.463 F5 317 5 317 N6 N6 N 0 1 N N N -3.044 64.731 33.830 2.568 0.077 2.585 N6 317 6 317 C7 C7 C 0 1 N N N -5.787 64.086 33.713 3.304 -1.341 -0.856 C7 317 7 317 C8 C8 C 0 1 N N N -0.875 63.148 37.771 5.481 2.558 -0.347 C8 317 8 317 C9 C9 C 0 1 N N N -0.309 64.020 38.880 6.992 2.339 -0.571 C9 317 9 317 C10 C10 C 0 1 N N N -1.031 65.367 38.807 7.147 0.798 -0.561 C10 317 10 317 C11 C11 C 0 1 N N N -2.176 65.221 37.804 6.129 0.373 0.531 C11 317 11 317 C18 C18 C 0 1 N N N -6.592 63.080 32.873 4.481 -2.258 -0.520 C18 317 12 317 C19 C19 C 0 1 N N N -7.569 63.610 31.922 5.484 -2.559 -1.635 C19 317 13 317 C20 C20 C 0 1 N N N -8.016 63.002 33.173 4.508 -3.642 -1.172 C20 317 14 317 C26 C26 C 0 1 Y N N -5.806 63.278 36.003 1.242 -0.309 0.055 C26 317 15 317 N27 N27 N 0 1 Y N N -6.186 62.113 36.508 0.013 -0.704 0.278 N27 317 16 317 C28 C28 C 0 1 Y N N -6.940 62.445 37.562 -0.778 0.278 -0.209 C28 317 17 317 N29 N29 N 0 1 Y N N -7.024 63.799 37.709 0.009 1.203 -0.695 N29 317 18 317 O30 O30 O 0 1 Y N N -6.266 64.352 36.667 1.169 0.883 -0.545 O30 317 19 317 C31 C31 C 0 1 Y N N -7.598 61.557 38.564 -2.262 0.303 -0.196 C31 317 20 317 C32 C32 C 0 1 Y N N -6.989 60.265 38.660 -2.949 1.387 -0.737 C32 317 21 317 C33 C33 C 0 1 Y N N -7.442 59.312 39.599 -4.329 1.404 -0.723 C33 317 22 317 C34 C34 C 0 1 Y N N -8.529 59.641 40.460 -5.031 0.347 -0.172 C34 317 23 317 C35 C35 C 0 1 Y N N -9.163 60.903 40.381 -4.356 -0.732 0.367 C35 317 24 317 C36 C36 C 0 1 Y N N -8.714 61.857 39.444 -2.974 -0.763 0.354 C36 317 25 317 S40 S40 S 0 1 N N N -9.082 58.485 41.668 -6.793 0.377 -0.157 S40 317 26 317 O41 O41 O 0 1 N N N -8.010 57.597 41.971 -7.147 -0.444 0.947 O41 317 27 317 O42 O42 O 0 1 N N N -10.278 57.855 41.095 -7.120 1.760 -0.176 O42 317 28 317 C43 C43 C 0 1 N N N -9.520 59.520 43.051 -7.272 -0.413 -1.718 C43 317 29 317 CL47 CL47 CL 0 0 N N N -9.587 63.367 39.506 -2.128 -2.122 1.025 CL47 317 30 317 H1 H1 H 0 1 N N N -4.542 62.413 34.463 2.240 -1.996 0.899 H1 317 31 317 H2 H2 H 0 1 N N N -3.926 65.138 35.721 4.250 -0.748 1.634 H2 317 32 317 HN6 HN6 H 0 1 N N N -3.774 64.832 33.154 3.124 0.581 3.259 HN6 317 33 317 HN6A HN6A H 0 0 N N N -2.585 65.610 33.959 1.721 0.580 2.366 HN6A 317 34 317 H7 H7 H 0 1 N N N -6.493 64.760 34.220 2.662 -1.829 -1.590 H7 317 35 317 H7A H7A H 0 1 N N N -5.116 64.631 33.032 3.679 -0.404 -1.268 H7A 317 36 317 H8 H8 H 0 1 N N N -1.321 62.240 38.202 4.980 2.699 -1.305 H8 317 37 317 H8A H8A H 0 1 N N N -0.073 62.853 37.078 5.321 3.428 0.289 H8A 317 38 317 H9 H9 H 0 1 N N N -0.479 63.549 39.859 7.300 2.749 -1.533 H9 317 39 317 H9A H9A H 0 1 N N N 0.776 64.152 38.757 7.568 2.787 0.239 H9A 317 40 317 H10 H10 H 0 1 N N N -1.427 65.639 39.797 6.881 0.375 -1.529 H10 317 41 317 H10A H10A H 0 0 N N N -0.338 66.160 38.490 8.159 0.511 -0.276 H10A 317 42 317 H11 H11 H 0 1 N N N -2.191 66.084 37.122 6.558 0.501 1.525 H11 317 43 317 H11A H11A H 0 0 N N N -3.142 65.180 38.329 5.819 -0.661 0.380 H11A 317 44 317 H18 H18 H 0 1 N N N -5.759 62.365 32.797 4.869 -2.173 0.496 H18 317 45 317 H19 H19 H 0 1 N N N -7.710 64.625 31.522 5.305 -2.103 -2.609 H19 317 46 317 H19A H19A H 0 0 N N N -7.788 63.475 30.852 6.531 -2.671 -1.354 H19A 317 47 317 H20 H20 H 0 1 N N N -8.665 62.133 33.358 4.913 -4.467 -0.586 H20 317 48 317 H20A H20A H 0 0 N N N -8.665 63.301 34.009 3.687 -3.899 -1.841 H20A 317 49 317 H32 H32 H 0 1 N N N -6.169 60.015 38.003 -2.402 2.213 -1.167 H32 317 50 317 H33 H33 H 0 1 N N N -6.969 58.343 39.664 -4.861 2.245 -1.142 H33 317 51 317 H35 H35 H 0 1 N N N -9.989 61.136 41.037 -4.909 -1.555 0.796 H35 317 52 317 H43 H43 H 0 1 N N N -9.610 58.903 43.957 -6.883 -1.430 -1.745 H43 317 53 317 H43A H43A H 0 0 N N N -8.739 60.280 43.201 -8.359 -0.438 -1.793 H43A 317 54 317 H43B H43B H 0 0 N N N -10.481 60.016 42.848 -6.863 0.155 -2.553 H43B 317 55 # 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 317 C1 C2 SING N N 1 317 C1 C7 SING N N 2 317 C1 C26 SING N N 3 317 C2 C3 SING N N 4 317 C2 N6 SING N N 5 317 C3 C4 DOUB N N 6 317 C3 F5 SING N N 7 317 C4 C8 SING N N 8 317 C4 C11 SING N N 9 317 C7 C18 SING N N 10 317 C8 C9 SING N N 11 317 C9 C10 SING N N 12 317 C10 C11 SING N N 13 317 C18 C19 SING N N 14 317 C18 C20 SING N N 15 317 C19 C20 SING N N 16 317 C26 N27 DOUB Y N 17 317 C26 O30 SING Y N 18 317 N27 C28 SING Y N 19 317 C28 N29 DOUB Y N 20 317 C28 C31 SING Y N 21 317 N29 O30 SING Y N 22 317 C31 C32 DOUB Y N 23 317 C31 C36 SING Y N 24 317 C32 C33 SING Y N 25 317 C33 C34 DOUB Y N 26 317 C34 C35 SING Y N 27 317 C34 S40 SING N N 28 317 C35 C36 DOUB Y N 29 317 C36 CL47 SING N N 30 317 S40 O41 DOUB N N 31 317 S40 O42 DOUB N N 32 317 S40 C43 SING N N 33 317 C1 H1 SING N N 34 317 C2 H2 SING N N 35 317 N6 HN6 SING N N 36 317 N6 HN6A SING N N 37 317 C7 H7 SING N N 38 317 C7 H7A SING N N 39 317 C8 H8 SING N N 40 317 C8 H8A SING N N 41 317 C9 H9 SING N N 42 317 C9 H9A SING N N 43 317 C10 H10 SING N N 44 317 C10 H10A SING N N 45 317 C11 H11 SING N N 46 317 C11 H11A SING N N 47 317 C18 H18 SING N N 48 317 C19 H19 SING N N 49 317 C19 H19A SING N N 50 317 C20 H20 SING N N 51 317 C20 H20A SING N N 52 317 C32 H32 SING N N 53 317 C33 H33 SING N N 54 317 C35 H35 SING N N 55 317 C43 H43 SING N N 56 317 C43 H43A SING N N 57 317 C43 H43B SING N N 58 # 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 317 SMILES ACDLabs 10.04 "F/C(=C1/CCCC1)C(N)C(c2nc(no2)c3c(Cl)cc(cc3)S(=O)(=O)C)CC4CC4" 317 SMILES_CANONICAL CACTVS 3.341 "C[S](=O)(=O)c1ccc(c(Cl)c1)c2noc(n2)[C@@H](CC3CC3)[C@H](N)C(F)=C4CCCC4" 317 SMILES CACTVS 3.341 "C[S](=O)(=O)c1ccc(c(Cl)c1)c2noc(n2)[CH](CC3CC3)[CH](N)C(F)=C4CCCC4" 317 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CS(=O)(=O)c1ccc(c(c1)Cl)c2nc(on2)[C@@H](CC3CC3)[C@@H](C(=C4CCCC4)F)N" 317 SMILES "OpenEye OEToolkits" 1.5.0 "CS(=O)(=O)c1ccc(c(c1)Cl)c2nc(on2)C(CC3CC3)C(C(=C4CCCC4)F)N" 317 InChI InChI 1.03 "InChI=1S/C21H25ClFN3O3S/c1-30(27,28)14-8-9-15(17(22)11-14)20-25-21(29-26-20)16(10-12-6-7-12)19(24)18(23)13-4-2-3-5-13/h8-9,11-12,16,19H,2-7,10,24H2,1H3/t16-,19-/m0/s1" 317 InChIKey InChI 1.03 XCCSSVMRGIQMGF-LPHOPBHVSA-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 317 "SYSTEMATIC NAME" ACDLabs 10.04 "(2S,3S)-3-{3-[2-chloro-4-(methylsulfonyl)phenyl]-1,2,4-oxadiazol-5-yl}-1-cyclopentylidene-4-cyclopropyl-1-fluorobutan-2-amine" 317 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S,3S)-3-[3-(2-chloro-4-methylsulfonyl-phenyl)-1,2,4-oxadiazol-5-yl]-1-cyclopentylidene-4-cyclopropyl-1-fluoro-butan-2-amine" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 317 "Create component" 2008-01-30 RCSB 317 "Modify aromatic_flag" 2011-06-04 RCSB 317 "Modify descriptor" 2011-06-04 RCSB #