data_IIB
# 
_chem_comp.id                                    IIB 
_chem_comp.name                                  1-{[5-(5-CHLORO-2-THIENYL)ISOXAZOL-3-YL]METHYL}-3-CYANO-N-(1-ISOPROPYLPIPERIDIN-4-YL)-7-METHYL-1H-INDOLE-2-CARBOXAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C27 H28 Cl N5 O2 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "1-[5-(5-CHLORO-THIOPHEN-2-YL)-ISOXAZOL-3-YLMETHYL]-3-CYANO-7-METHYL-1H-INDOLE-2-CARBOXYLIC ACID (1-ISOPROPYL-PIPERIDIN-4-YL)-AMIDE" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-04-27 
_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                        522.062 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     IIB 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        2BQ6 
_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 
IIB C1   C1   C  0 1 Y N N 1.483  7.445  25.188 -3.369 -5.287 1.023  C1   IIB 1  
IIB C2   C2   C  0 1 Y N N 2.601  7.734  24.334 -2.560 -4.211 1.311  C2   IIB 2  
IIB C3   C3   C  0 1 Y N N 3.280  6.672  23.618 -2.638 -3.057 0.534  C3   IIB 3  
IIB C4   C4   C  0 1 Y N N 2.786  5.315  23.801 -3.548 -3.014 -0.539 C4   IIB 4  
IIB C5   C5   C  0 1 Y N N 1.664  5.054  24.663 -4.358 -4.117 -0.813 C5   IIB 5  
IIB C6   C6   C  0 1 Y N N 1.013  6.109  25.355 -4.265 -5.237 -0.036 C6   IIB 6  
IIB N7   N7   N  0 1 Y N N 4.390  6.560  22.705 -1.976 -1.853 0.577  N7   IIB 7  
IIB C8   C8   C  0 1 Y N N 4.605  5.209  22.330 -2.420 -1.029 -0.424 C8   IIB 8  
IIB C9   C9   C  0 1 Y N N 3.610  4.452  23.004 -3.400 -1.686 -1.150 C9   IIB 9  
IIB C10  C10  C  0 1 N N N 5.620  4.702  21.455 -1.936 0.337  -0.682 C10  IIB 10 
IIB N11  N11  N  0 1 N N N 5.280  3.771  20.539 -2.473 1.379  -0.017 N11  IIB 11 
IIB C12  C12  C  0 1 N N N 6.271  3.009  19.773 -2.072 2.748  -0.353 C12  IIB 12 
IIB C13  C13  C  0 1 N N N 6.024  1.500  19.873 -0.801 3.114  0.421  C13  IIB 13 
IIB C14  C14  C  0 1 N N N 7.101  0.746  19.044 -0.454 4.580  0.153  C14  IIB 14 
IIB N15  N15  N  0 1 N N N 7.184  1.264  17.626 -1.545 5.442  0.622  N15  IIB 15 
IIB C16  C16  C  0 1 N N N 7.440  2.722  17.537 -2.717 5.154  -0.210 C16  IIB 16 
IIB C17  C17  C  0 1 N N N 6.328  3.477  18.298 -3.189 3.720  0.037  C17  IIB 17 
IIB C27  C27  C  0 1 N N N 8.152  0.571  16.693 -1.146 6.825  0.327  C27  IIB 18 
IIB C28  C28  C  0 1 N N N 7.350  0.062  15.497 -2.276 7.777  0.726  C28  IIB 19 
IIB C32  C32  C  0 1 N N N 8.931  -0.600 17.348 0.116  7.172  1.119  C32  IIB 20 
IIB C37  C37  C  0 1 N N N 5.215  7.720  22.214 -0.944 -1.501 1.555  C37  IIB 21 
IIB C38  C38  C  0 1 Y N N 6.576  7.899  22.839 0.409  -1.895 1.021  C38  IIB 22 
IIB N41  N41  N  0 1 Y N N 7.424  8.878  22.414 0.771  -3.080 0.615  N41  IIB 23 
IIB O42  O42  O  0 1 Y N N 8.500  8.762  23.129 1.919  -3.098 0.235  O42  IIB 24 
IIB C43  C43  C  0 1 Y N N 8.370  7.744  24.000 2.494  -1.886 0.353  C43  IIB 25 
IIB C44  C44  C  0 1 Y N N 7.139  7.132  23.870 1.530  -1.057 0.871  C44  IIB 26 
IIB C45  C45  C  0 1 Y N N 9.412  7.304  24.957 3.874  -1.525 -0.001 C45  IIB 27 
IIB S46  S46  S  0 1 Y N N 11.036 7.527  24.611 4.692  0.056  0.131  S46  IIB 28 
IIB C47  C47  C  0 1 Y N N 11.448 6.772  26.060 6.288  -0.429 -0.505 C47  IIB 29 
IIB C48  C48  C  0 1 Y N N 10.352 6.344  26.841 6.102  -1.750 -0.775 C48  IIB 30 
IIB C49  C49  C  0 1 Y N N 9.131  6.658  26.187 4.878  -2.323 -0.518 C49  IIB 31 
IIB CL50 CL50 CL 0 0 N N N 13.088 6.554  26.487 7.714  0.536  -0.722 CL50 IIB 32 
IIB O56  O56  O  0 1 N N N 6.784  5.073  21.573 -1.052 0.526  -1.496 O56  IIB 33 
IIB C7   C7   C  0 1 N N N 3.394  3.014  22.948 -4.124 -1.173 -2.275 C7   IIB 34 
IIB N1   N1   N  0 1 N N N 3.185  1.889  22.885 -4.698 -0.766 -3.167 N1   IIB 35 
IIB C11  C11  C  0 1 N N N 2.949  9.174  24.289 -1.594 -4.280 2.465  C11  IIB 36 
IIB H1   H1   H  0 1 N N N 0.991  8.251  25.711 -3.306 -6.180 1.628  H1   IIB 37 
IIB H5   H5   H  0 1 N N N 1.312  4.040  24.785 -5.057 -4.085 -1.636 H5   IIB 38 
IIB H6   H6   H  0 1 N N N 0.172  5.902  26.000 -4.892 -6.090 -0.249 H6   IIB 39 
IIB H11  H11  H  0 1 N N N 4.310  3.593  20.376 -3.125 1.223  0.684  H11  IIB 40 
IIB H12  H12  H  0 1 N N N 7.255  3.209  20.222 -1.881 2.822  -1.423 H12  IIB 41 
IIB H131 1H13 H  0 0 N N N 5.024  1.264  19.479 -0.970 2.969  1.488  H131 IIB 42 
IIB H132 2H13 H  0 0 N N N 6.085  1.187  20.926 0.021  2.479  0.092  H132 IIB 43 
IIB H141 1H14 H  0 0 N N N 6.821  -0.317 19.005 -0.310 4.729  -0.917 H141 IIB 44 
IIB H142 2H14 H  0 0 N N N 8.079  0.885  19.528 0.464  4.838  0.681  H142 IIB 45 
IIB H161 1H16 H  0 0 N N N 7.445  3.034  16.482 -3.520 5.848  0.041  H161 IIB 46 
IIB H162 2H16 H  0 0 N N N 8.417  2.953  17.986 -2.454 5.273  -1.261 H162 IIB 47 
IIB H171 1H17 H  0 0 N N N 6.546  4.555  18.273 -3.430 3.593  1.093  H171 IIB 48 
IIB H172 2H17 H  0 0 N N N 5.360  3.275  17.817 -4.074 3.519  -0.566 H172 IIB 49 
IIB H27  H27  H  0 1 N N N 8.920  1.301  16.397 -0.946 6.926  -0.739 H27  IIB 50 
IIB H281 1H28 H  0 0 N N N 7.755  -0.907 15.170 -1.981 8.803  0.507  H281 IIB 51 
IIB H282 2H28 H  0 0 N N N 7.422  0.787  14.673 -3.175 7.530  0.162  H282 IIB 52 
IIB H283 3H28 H  0 0 N N N 6.296  -0.060 15.787 -2.477 7.676  1.792  H283 IIB 53 
IIB H321 1H32 H  0 0 N N N 8.338  -1.017 18.175 0.336  8.233  1.005  H321 IIB 54 
IIB H322 2H32 H  0 0 N N N 9.892  -0.230 17.735 -0.042 6.944  2.173  H322 IIB 55 
IIB H323 3H32 H  0 0 N N N 9.115  -1.383 16.598 0.954  6.585  0.742  H323 IIB 56 
IIB H371 1H37 H  0 0 N N N 4.646  8.620  22.489 -0.965 -0.426 1.735  H371 IIB 57 
IIB H372 2H37 H  0 0 N N N 5.371  7.572  21.135 -1.133 -2.029 2.490  H372 IIB 58 
IIB H44  H44  H  0 1 N N N 6.724  6.295  24.412 1.612  -0.006 1.107  H44  IIB 59 
IIB H48  H48  H  0 1 N N N 10.431 5.849  27.798 6.907  -2.342 -1.184 H48  IIB 60 
IIB H49  H49  H  0 1 N N N 8.144  6.439  26.567 4.704  -3.368 -0.723 H49  IIB 61 
IIB H111 1H11 H  0 0 N N N 2.162  9.725  23.753 -2.048 -3.829 3.347  H111 IIB 62 
IIB H112 2H11 H  0 0 N N N 3.908  9.303  23.766 -1.351 -5.322 2.674  H112 IIB 63 
IIB H113 3H11 H  0 0 N N N 3.035  9.563  25.314 -0.683 -3.739 2.209  H113 IIB 64 
# 
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 
IIB C1  C2   DOUB Y N 1  
IIB C1  C6   SING Y N 2  
IIB C1  H1   SING N N 3  
IIB C2  C3   SING Y N 4  
IIB C2  C11  SING N N 5  
IIB C3  C4   DOUB Y N 6  
IIB C3  N7   SING Y N 7  
IIB C4  C5   SING Y N 8  
IIB C4  C9   SING Y N 9  
IIB C5  C6   DOUB Y N 10 
IIB C5  H5   SING N N 11 
IIB C6  H6   SING N N 12 
IIB N7  C8   SING Y N 13 
IIB N7  C37  SING N N 14 
IIB C8  C9   DOUB Y N 15 
IIB C8  C10  SING N N 16 
IIB C9  C7   SING N N 17 
IIB C10 N11  SING N N 18 
IIB C10 O56  DOUB N N 19 
IIB N11 C12  SING N N 20 
IIB N11 H11  SING N N 21 
IIB C12 C13  SING N N 22 
IIB C12 C17  SING N N 23 
IIB C12 H12  SING N N 24 
IIB C13 C14  SING N N 25 
IIB C13 H131 SING N N 26 
IIB C13 H132 SING N N 27 
IIB C14 N15  SING N N 28 
IIB C14 H141 SING N N 29 
IIB C14 H142 SING N N 30 
IIB N15 C16  SING N N 31 
IIB N15 C27  SING N N 32 
IIB C16 C17  SING N N 33 
IIB C16 H161 SING N N 34 
IIB C16 H162 SING N N 35 
IIB C17 H171 SING N N 36 
IIB C17 H172 SING N N 37 
IIB C27 C28  SING N N 38 
IIB C27 C32  SING N N 39 
IIB C27 H27  SING N N 40 
IIB C28 H281 SING N N 41 
IIB C28 H282 SING N N 42 
IIB C28 H283 SING N N 43 
IIB C32 H321 SING N N 44 
IIB C32 H322 SING N N 45 
IIB C32 H323 SING N N 46 
IIB C37 C38  SING N N 47 
IIB C37 H371 SING N N 48 
IIB C37 H372 SING N N 49 
IIB C38 N41  DOUB Y N 50 
IIB C38 C44  SING Y N 51 
IIB N41 O42  SING Y N 52 
IIB O42 C43  SING Y N 53 
IIB C43 C44  DOUB Y N 54 
IIB C43 C45  SING N N 55 
IIB C44 H44  SING N N 56 
IIB C45 S46  SING Y N 57 
IIB C45 C49  DOUB Y N 58 
IIB S46 C47  SING Y N 59 
IIB C47 C48  DOUB Y N 60 
IIB C47 CL50 SING N N 61 
IIB C48 C49  SING Y N 62 
IIB C48 H48  SING N N 63 
IIB C49 H49  SING N N 64 
IIB C7  N1   TRIP N N 65 
IIB C11 H111 SING N N 66 
IIB C11 H112 SING N N 67 
IIB C11 H113 SING N N 68 
# 
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 
IIB SMILES           ACDLabs              10.04 Clc5sc(c1onc(c1)Cn4c2c(cccc2c(C#N)c4C(=O)NC3CCN(C(C)C)CC3)C)cc5                                                                                                                          
IIB InChI            InChI                1.02b InChI=1/C27H28ClN5O2S/c1-16(2)32-11-9-18(10-12-32)30-27(34)26-21(14-29)20-6-4-5-17(3)25(20)33(26)15-19-13-22(35-31-19)23-7-8-24(28)36-23/h4-8,13,16,18H,9-12,15H2,1-3H3,(H,30,34)/f/h30H 
IIB InChIKey         InChI                1.02b MCLVKEPZVPUETD-SREBMQDQCI                                                                                                                                                                
IIB SMILES_CANONICAL CACTVS               3.341 CC(C)N1CCC(CC1)NC(=O)c2n(Cc3cc(on3)c4sc(Cl)cc4)c5c(C)cccc5c2C#N                                                                                                                          
IIB SMILES           CACTVS               3.341 CC(C)N1CCC(CC1)NC(=O)c2n(Cc3cc(on3)c4sc(Cl)cc4)c5c(C)cccc5c2C#N                                                                                                                          
IIB SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1cccc2c1n(c(c2C#N)C(=O)NC3CCN(CC3)C(C)C)Cc4cc(on4)c5ccc(s5)Cl                                                                                                                          
IIB SMILES           "OpenEye OEToolkits" 1.5.0 Cc1cccc2c1n(c(c2C#N)C(=O)NC3CCN(CC3)C(C)C)Cc4cc(on4)c5ccc(s5)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 
IIB "SYSTEMATIC NAME" ACDLabs              10.04 1-{[5-(5-chlorothiophen-2-yl)isoxazol-3-yl]methyl}-3-cyano-7-methyl-N-[1-(1-methylethyl)piperidin-4-yl]-1H-indole-2-carboxamide 
IIB "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-3-cyano-7-methyl-N-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide      
# 
