data_386
# 
_chem_comp.id                                    386 
_chem_comp.name                                  "N-(2,2-difluoro-5H-[1,3]dioxolo[4,5-f]benzimidazol-6-yl)-2-{[2-(trifluoromethoxy)benzoyl]amino}-1,3-thiazole-4-carboxamide" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H10 F5 N5 O5 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2014-07-03 
_chem_comp.pdbx_modified_date                    2014-09-05 
_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                        527.381 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     386 
_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        4TW9 
_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 
386 N1  N1  N 0 1 N N N 11.470 -14.989 6.430  -3.160 -0.578 0.041  N1  386 1  
386 C2  C1  C 0 1 Y N N 11.931 -16.558 8.741  -5.140 -2.631 0.041  C2  386 2  
386 O2  O1  O 0 1 N N N 12.706 -16.492 5.244  -4.782 0.939  -0.016 O2  386 3  
386 N3  N2  N 0 1 N N N 7.600  -11.104 4.271  1.953  0.020  0.096  N3  386 4  
386 C4  C2  C 0 1 Y N N 12.342 -16.992 9.997  -6.115 -3.604 0.040  C4  386 5  
386 N4  N3  N 0 1 Y N N 6.303  -9.205  3.630  4.171  1.036  0.113  N4  386 6  
386 C5  C3  C 0 1 Y N N 14.555 -17.406 9.142  -7.826 -1.922 -0.032 C5  386 7  
386 C6  C4  C 0 1 Y N N 13.655 -17.418 10.196 -7.455 -3.251 0.003  C6  386 8  
386 F5  F1  F 0 1 N N N 1.656  -5.415  5.902  11.120 -0.558 0.472  F5  386 9  
386 C19 C5  C 0 1 N N N 2.971  -5.088  5.803  9.892  -0.479 -0.194 C19 386 10 
386 F4  F2  F 0 1 N N N 3.214  -3.792  6.119  10.083 -0.513 -1.580 F4  386 11 
386 O4  O2  O 0 1 N N N 3.497  -5.387  4.495  9.183  0.713  0.192  O4  386 12 
386 C15 C6  C 0 1 Y N N 4.252  -6.480  4.702  7.860  0.372  0.178  C15 386 13 
386 C17 C7  C 0 1 Y N N 4.895  -7.240  3.756  6.719  1.152  0.149  C17 386 14 
386 O5  O3  O 0 1 N N N 3.633  -5.902  6.762  9.021  -1.547 0.222  O5  386 15 
386 C16 C8  C 0 1 Y N N 4.322  -6.784  6.037  7.760  -1.021 0.197  C16 386 16 
386 C18 C9  C 0 1 Y N N 5.035  -7.841  6.562  6.521  -1.629 0.187  C18 386 17 
386 C20 C10 C 0 1 Y N N 5.676  -8.598  5.623  5.362  -0.849 0.158  C20 386 18 
386 C14 C11 C 0 1 Y N N 5.592  -8.309  4.284  5.469  0.551  0.140  C14 386 19 
386 N5  N4  N 0 1 Y N N 6.412  -9.690  5.823  4.036  -1.149 0.143  N5  386 20 
386 C13 C12 C 0 1 Y N N 6.784  -10.028 4.578  3.335  -0.044 0.117  C13 386 21 
386 C12 C13 C 0 1 N N N 8.221  -11.844 5.249  1.334  1.217  0.070  C12 386 22 
386 O3  O4  O 0 1 N N N 7.992  -11.619 6.436  1.991  2.241  0.065  O3  386 23 
386 C10 C14 C 0 1 Y N N 9.227  -12.857 4.863  -0.135 1.286  0.048  C10 386 24 
386 C11 C15 C 0 1 Y N N 9.628  -13.280 3.581  -0.806 2.456  0.016  C11 386 25 
386 S   S1  S 0 1 Y N N 10.786 -14.406 3.769  -2.487 2.140  -0.001 S   386 26 
386 N2  N5  N 0 1 Y N N 9.881  -13.454 5.856  -0.905 0.193  0.052  N2  386 27 
386 C9  C16 C 0 1 Y N N 10.779 -14.337 5.401  -2.183 0.407  0.036  C9  386 28 
386 C8  C17 C 0 1 N N N 12.352 -16.041 6.328  -4.463 -0.234 0.011  C8  386 29 
386 C1  C18 C 0 1 Y N N 12.830 -16.546 7.656  -5.502 -1.281 0.010  C1  386 30 
386 C3  C19 C 0 1 Y N N 14.158 -16.965 7.883  -6.858 -0.929 -0.021 C3  386 31 
386 O1  O5  O 0 1 N N N 15.091 -16.977 6.887  -7.222 0.378  -0.052 O1  386 32 
386 C7  C20 C 0 1 N N N 15.757 -15.779 6.540  -8.622 0.661  -0.083 C7  386 33 
386 F3  F3  F 0 1 N N N 16.175 -15.798 5.222  -9.189 0.086  -1.226 F3  386 34 
386 F2  F4  F 0 1 N N N 14.857 -14.802 6.704  -9.231 0.127  1.058  F2  386 35 
386 F1  F5  F 0 1 N N N 16.735 -15.520 7.450  -8.818 2.046  -0.112 F1  386 36 
386 H1  H1  H 0 1 N N N 11.302 -14.648 7.355  -2.906 -1.514 0.063  H1  386 37 
386 H2  H2  H 0 1 N N N 10.913 -16.227 8.596  -4.097 -2.910 0.070  H2  386 38 
386 H3  H3  H 0 1 N N N 7.741  -11.349 3.312  1.429  -0.796 0.101  H3  386 39 
386 H4  H4  H 0 1 N N N 11.643 -16.999 10.820 -5.835 -4.646 0.068  H4  386 40 
386 H5  H5  H 0 1 N N N 6.452  -9.261  2.643  3.905  1.969  0.099  H5  386 41 
386 H6  H6  H 0 1 N N N 15.570 -17.741 9.298  -8.873 -1.655 -0.061 H6  386 42 
386 H7  H7  H 0 1 N N N 13.971 -17.757 11.172 -8.213 -4.021 0.002  H7  386 43 
386 H8  H8  H 0 1 N N N 4.859  -7.022  2.699  6.800  2.229  0.135  H8  386 44 
386 H9  H9  H 0 1 N N N 5.082  -8.051  7.620  6.448  -2.707 0.201  H9  386 45 
386 H11 H11 H 0 1 N N N 9.236  -12.921 2.641  -0.354 3.436  0.004  H11 386 46 
# 
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 
386 C11 S   SING Y N 1  
386 C11 C10 DOUB Y N 2  
386 N4  C14 SING Y N 3  
386 N4  C13 SING Y N 4  
386 C17 C14 DOUB Y N 5  
386 C17 C15 SING Y N 6  
386 S   C9  SING Y N 7  
386 N3  C13 SING N N 8  
386 N3  C12 SING N N 9  
386 C14 C20 SING Y N 10 
386 O4  C15 SING N N 11 
386 O4  C19 SING N N 12 
386 C13 N5  DOUB Y N 13 
386 C15 C16 DOUB Y N 14 
386 C10 C12 SING N N 15 
386 C10 N2  SING Y N 16 
386 F3  C7  SING N N 17 
386 O2  C8  DOUB N N 18 
386 C12 O3  DOUB N N 19 
386 C9  N2  DOUB Y N 20 
386 C9  N1  SING N N 21 
386 C20 N5  SING Y N 22 
386 C20 C18 DOUB Y N 23 
386 C19 F5  SING N N 24 
386 C19 F4  SING N N 25 
386 C19 O5  SING N N 26 
386 C16 C18 SING Y N 27 
386 C16 O5  SING N N 28 
386 C8  N1  SING N N 29 
386 C8  C1  SING N N 30 
386 C7  F2  SING N N 31 
386 C7  O1  SING N N 32 
386 C7  F1  SING N N 33 
386 O1  C3  SING N N 34 
386 C1  C3  DOUB Y N 35 
386 C1  C2  SING Y N 36 
386 C3  C5  SING Y N 37 
386 C2  C4  DOUB Y N 38 
386 C5  C6  DOUB Y N 39 
386 C4  C6  SING Y N 40 
386 N1  H1  SING N N 41 
386 C2  H2  SING N N 42 
386 N3  H3  SING N N 43 
386 C4  H4  SING N N 44 
386 N4  H5  SING N N 45 
386 C5  H6  SING N N 46 
386 C6  H7  SING N N 47 
386 C17 H8  SING N N 48 
386 C18 H9  SING N N 49 
386 C11 H11 SING N N 50 
# 
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 
386 SMILES           ACDLabs              12.01 "O=C(Nc4nc(C(=O)Nc3nc2cc1OC(F)(F)Oc1cc2n3)cs4)c5ccccc5OC(F)(F)F"                                                                                                              
386 InChI            InChI                1.03  "InChI=1S/C20H10F5N5O5S/c21-19(22,23)33-12-4-2-1-3-8(12)15(31)30-18-28-11(7-36-18)16(32)29-17-26-9-5-13-14(6-10(9)27-17)35-20(24,25)34-13/h1-7H,(H,28,30,31)(H2,26,27,29,32)" 
386 InChIKey         InChI                1.03  DVVVOLSRHWJCHV-UHFFFAOYSA-N                                                                                                                                                   
386 SMILES_CANONICAL CACTVS               3.385 "FC(F)(F)Oc1ccccc1C(=O)Nc2scc(n2)C(=O)Nc3[nH]c4cc5OC(F)(F)Oc5cc4n3"                                                                                                           
386 SMILES           CACTVS               3.385 "FC(F)(F)Oc1ccccc1C(=O)Nc2scc(n2)C(=O)Nc3[nH]c4cc5OC(F)(F)Oc5cc4n3"                                                                                                           
386 SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "c1ccc(c(c1)C(=O)Nc2nc(cs2)C(=O)Nc3[nH]c4cc5c(cc4n3)OC(O5)(F)F)OC(F)(F)F"                                                                                                     
386 SMILES           "OpenEye OEToolkits" 1.9.2 "c1ccc(c(c1)C(=O)Nc2nc(cs2)C(=O)Nc3[nH]c4cc5c(cc4n3)OC(O5)(F)F)OC(F)(F)F"                                                                                                     
# 
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 
386 "SYSTEMATIC NAME" ACDLabs              12.01 "N-(2,2-difluoro-5H-[1,3]dioxolo[4,5-f]benzimidazol-6-yl)-2-{[2-(trifluoromethoxy)benzoyl]amino}-1,3-thiazole-4-carboxamide"                
386 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "N-[2,2-bis(fluoranyl)-5H-[1,3]dioxolo[4,5-f]benzimidazol-6-yl]-2-[[2-(trifluoromethyloxy)phenyl]carbonylamino]-1,3-thiazole-4-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 
386 "Create component"  2014-07-03 RCSB 
386 "Initial release"   2014-07-30 RCSB 
386 "Modify descriptor" 2014-09-05 RCSB 
# 
