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                    2008-10-14 
_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 N N 17 
317 C26 O30  SING N N 18 
317 N27 C28  SING N N 19 
317 C28 N29  DOUB N N 20 
317 C28 C31  SING N N 21 
317 N29 O30  SING N N 22 
317 C31 C32  DOUB N N 23 
317 C31 C36  SING N N 24 
317 C32 C33  SING N N 25 
317 C33 C34  DOUB N N 26 
317 C34 C35  SING N N 27 
317 C34 S40  SING N N 28 
317 C35 C36  DOUB N 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 Y N 36 
317 N6  HN6A SING Y N 37 
317 C7  H7   SING Y N 38 
317 C7  H7A  SING Y N 39 
317 C8  H8   SING N N 40 
317 C8  H8A  SING Y N 41 
317 C9  H9   SING Y N 42 
317 C9  H9A  SING Y N 43 
317 C10 H10  SING Y N 44 
317 C10 H10A SING N N 45 
317 C11 H11  SING Y N 46 
317 C11 H11A SING N N 47 
317 C18 H18  SING Y N 48 
317 C19 H19  SING N N 49 
317 C19 H19A SING Y 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 InChI            InChI                1.02b InChI=1/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                1.02b XCCSSVMRGIQMGF-LPHOPBHVBD                                                                                                                                             
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                                                                                                            
# 
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 
# 
