data_276
# 
_chem_comp.id                                    276 
_chem_comp.name                                  4-[[2-[[4-chloro-3-(trifluoromethyl)phenyl]amino]-3H-benzimidazol-5-yl]oxy]-N-methyl-pyridine-2-carboxamide 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H15 Cl F3 N5 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-08-09 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        461.824 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     276 
_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        2QU5 
_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 
276 C1   C1   C  0 1 Y N N 67.022 90.619  42.448 -4.490  0.644  -0.414 C1   276 1  
276 C2   C2   C  0 1 Y N N 66.825 90.064  41.175 -5.292  1.665  -0.889 C2   276 2  
276 N3   N3   N  0 1 Y N N 67.835 89.926  40.265 -6.604  1.577  -0.833 N3   276 3  
276 C4   C4   C  0 1 Y N N 69.093 90.343  40.602 -7.213  0.513  -0.323 C4   276 4  
276 C5   C5   C  0 1 Y N N 69.366 90.903  41.845 -6.474  -0.555 0.176  C5   276 5  
276 C6   C6   C  0 1 Y N N 68.334 91.050  42.783 -5.083  -0.492 0.130  C6   276 6  
276 C10  C10  C  0 1 N N N 70.212 90.210  39.645 -8.694  0.463  -0.282 C10  276 7  
276 O11  O11  O  0 1 N N N 71.304 90.798  39.775 -9.256  -0.508 0.184  O11  276 8  
276 N12  N12  N  0 1 N N N 69.937 89.378  38.601 -9.416  1.495  -0.763 N12  276 9  
276 C13  C13  C  0 1 N N N 70.931 89.127  37.557 -10.880 1.445  -0.723 C13  276 10 
276 O17  O17  O  0 1 N N N 68.765 91.619  43.981 -4.326  -1.515 0.601  O17  276 11 
276 C18  C18  C  0 1 Y N N 67.941 92.125  44.977 -2.977  -1.432 0.451  C18  276 12 
276 C19  C19  C  0 1 Y N N 67.223 93.337  44.821 -2.236  -0.638 1.309  C19  276 13 
276 C20  C20  C  0 1 Y N N 66.454 93.815  45.869 -0.861  -0.554 1.156  C20  276 14 
276 C21  C21  C  0 1 Y N N 66.384 93.084  47.106 -0.223  -1.273 0.132  C21  276 15 
276 C22  C22  C  0 1 Y N N 67.079 91.900  47.257 -0.983  -2.071 -0.727 C22  276 16 
276 C23  C23  C  0 1 Y N N 67.862 91.411  46.194 -2.347  -2.150 -0.561 C23  276 17 
276 N27  N27  N  0 1 Y N N 65.671 94.935  46.021 0.139   0.130  1.828  N27  276 18 
276 C28  C28  C  0 1 Y N N 65.166 94.893  47.263 1.322   -0.179 1.217  C28  276 19 
276 N29  N29  N  0 1 Y N N 65.568 93.804  47.938 1.107   -1.003 0.222  N29  276 20 
276 N32  N32  N  0 1 N N N 64.282 95.903  47.862 2.559   0.305  1.593  N32  276 21 
276 C33  C33  C  0 1 Y N N 63.277 96.609  47.272 3.697   -0.037 0.856  C33  276 22 
276 C34  C34  C  0 1 Y N N 62.818 97.712  47.991 4.765   0.848  0.773  C34  276 23 
276 C35  C35  C  0 1 Y N N 61.776 98.545  47.526 5.887   0.508  0.045  C35  276 24 
276 C36  C36  C  0 1 Y N N 61.188 98.210  46.255 5.950   -0.713 -0.603 C36  276 25 
276 C37  C37  C  0 1 Y N N 61.644 97.095  45.509 4.888   -1.597 -0.523 C37  276 26 
276 C38  C38  C  0 1 Y N N 62.689 96.295  46.020 3.765   -1.265 0.209  C38  276 27 
276 C43  C43  C  0 1 N N N 61.345 99.724  48.394 7.045   1.468  -0.046 C43  276 28 
276 CL44 CL44 CL 0 0 N N N 59.890 99.121  45.528 7.363   -1.137 -1.518 CL44 276 29 
276 F45  F45  F  0 1 N N N 60.152 99.412  48.855 6.750   2.625  0.684  F45  276 30 
276 F46  F46  F  0 1 N N N 61.295 100.824 47.667 8.193   0.865  0.480  F46  276 31 
276 F47  F47  F  0 1 N N N 62.204 99.919  49.403 7.268   1.806  -1.385 F47  276 32 
276 H1   H1   H  0 1 N N N 66.206 90.715  43.149 -3.414  0.724  -0.469 H1   276 33 
276 H2   H2   H  0 1 N N N 65.834 89.732  40.903 -4.836  2.547  -1.312 H2   276 34 
276 H5   H5   H  0 1 N N N 70.369 91.223  42.087 -6.971  -1.419 0.591  H5   276 35 
276 HN12 HN12 H  0 0 N N N 69.043 88.933  38.548 -8.967  2.270  -1.135 HN12 276 36 
276 H131 1H13 H  0 0 N N N 70.429 89.064  36.580 -11.212 1.350  0.310  H131 276 37 
276 H132 2H13 H  0 0 N N N 71.662 89.949  37.542 -11.286 2.361  -1.153 H132 276 38 
276 H133 3H13 H  0 0 N N N 71.449 88.179  37.765 -11.230 0.588  -1.298 H133 276 39 
276 H19  H19  H  0 1 N N N 67.275 93.884  43.891 -2.728  -0.085 2.096  H19  276 40 
276 H22  H22  H  0 1 N N N 67.022 91.352  48.186 -0.501  -2.627 -1.517 H22  276 41 
276 H23  H23  H  0 1 N N N 68.405 90.485  46.309 -2.933  -2.770 -1.223 H23  276 42 
276 HN27 HN27 H  0 0 N N N 65.509 95.645  45.336 0.022   0.719  2.590  HN27 276 43 
276 HN32 HN32 H  0 0 N N N 64.439 96.098  48.830 2.639   0.881  2.369  HN32 276 44 
276 H34  H34  H  0 1 N N N 63.278 97.939  48.942 4.716   1.801  1.278  H34  276 45 
276 H37  H37  H  0 1 N N N 61.195 96.859  44.556 4.941   -2.551 -1.026 H37  276 46 
276 H38  H38  H  0 1 N N N 63.041 95.443  45.457 2.937   -1.955 0.272  H38  276 47 
# 
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 
276 C13  N12  SING Y N 1  
276 N12  C10  SING N N 2  
276 C10  O11  DOUB Y N 3  
276 C10  C4   SING N N 4  
276 N3   C4   DOUB Y N 5  
276 N3   C2   SING Y N 6  
276 C4   C5   SING Y N 7  
276 C2   C1   DOUB Y N 8  
276 C5   C6   DOUB N N 9  
276 C1   C6   SING N N 10 
276 C6   O17  SING N N 11 
276 O17  C18  SING N N 12 
276 C19  C18  DOUB N N 13 
276 C19  C20  SING N N 14 
276 C18  C23  SING N N 15 
276 C37  C38  DOUB N N 16 
276 C37  C36  SING N N 17 
276 CL44 C36  SING N N 18 
276 C20  N27  SING N N 19 
276 C20  C21  DOUB Y N 20 
276 C38  C33  SING Y N 21 
276 N27  C28  SING Y N 22 
276 C23  C22  DOUB N N 23 
276 C36  C35  DOUB Y N 24 
276 C21  C22  SING Y N 25 
276 C21  N29  SING Y N 26 
276 C28  N32  SING Y N 27 
276 C28  N29  DOUB N N 28 
276 C33  N32  SING Y N 29 
276 C33  C34  DOUB N N 30 
276 C35  C34  SING Y N 31 
276 C35  C43  SING N N 32 
276 F46  C43  SING N N 33 
276 C43  F45  SING Y N 34 
276 C43  F47  SING N N 35 
276 C1   H1   SING N N 36 
276 C2   H2   SING Y N 37 
276 C5   H5   SING N N 38 
276 N12  HN12 SING Y N 39 
276 C13  H131 SING N N 40 
276 C13  H132 SING Y N 41 
276 C13  H133 SING Y N 42 
276 C19  H19  SING Y N 43 
276 C22  H22  SING N N 44 
276 C23  H23  SING Y N 45 
276 N27  HN27 SING N N 46 
276 N32  HN32 SING N N 47 
276 C34  H34  SING N N 48 
276 C37  H37  SING N N 49 
276 C38  H38  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 
276 SMILES           ACDLabs              10.04 FC(F)(F)c1cc(ccc1Cl)Nc4nc3ccc(Oc2ccnc(C(=O)NC)c2)cc3n4                                                                                                                    
276 InChI            InChI                1.02b InChI=1/C21H15ClF3N5O2/c1-26-19(31)18-10-13(6-7-27-18)32-12-3-5-16-17(9-12)30-20(29-16)28-11-2-4-15(22)14(8-11)21(23,24)25/h2-10H,1H3,(H,26,31)(H2,28,29,30)/f/h26,28,30H 
276 InChIKey         InChI                1.02b ZJLSMLDOCGOURY-MCGURSJECB                                                                                                                                                 
276 SMILES_CANONICAL CACTVS               3.341 CNC(=O)c1cc(Oc2ccc3nc(Nc4ccc(Cl)c(c4)C(F)(F)F)[nH]c3c2)ccn1                                                                                                               
276 SMILES           CACTVS               3.341 CNC(=O)c1cc(Oc2ccc3nc(Nc4ccc(Cl)c(c4)C(F)(F)F)[nH]c3c2)ccn1                                                                                                               
276 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CNC(=O)c1cc(ccn1)Oc2ccc3c(c2)[nH]c(n3)Nc4ccc(c(c4)C(F)(F)F)Cl                                                                                                             
276 SMILES           "OpenEye OEToolkits" 1.5.0 CNC(=O)c1cc(ccn1)Oc2ccc3c(c2)[nH]c(n3)Nc4ccc(c(c4)C(F)(F)F)Cl                                                                                                             
# 
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 
276 "SYSTEMATIC NAME" ACDLabs              10.04 4-[(2-{[4-chloro-3-(trifluoromethyl)phenyl]amino}-1H-benzimidazol-6-yl)oxy]-N-methylpyridine-2-carboxamide  
276 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 4-[[2-[[4-chloro-3-(trifluoromethyl)phenyl]amino]-3H-benzimidazol-5-yl]oxy]-N-methyl-pyridine-2-carboxamide 
# 
