data_D91
# 
_chem_comp.id                                    D91 
_chem_comp.name                                  5-CHLORO-2-({3-ISOBUTYL-4-[(5-PYRIDIN-4-YLPYRIMIDIN-2-YL)CARBONYL]PIPERAZIN-1-YL}SULFONYL)-1H-INDOLE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C26 H27 Cl N6 O3 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         4-[(5-CHLOROINDOL-2-YL)SULFONYL]-2-(2-METHYLPROPYL)-1-[[5-(PYRIDIN-4-YL)PYRIMIDIN-2-YL]CARBONYL]PIPERAZINE 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-12-02 
_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                        539.049 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     D91 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   Y 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1WU1 
_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 
D91 C18  C18  C  0 1 N N R 4.287  6.331  22.766 -2.252 0.160  1.522  C18  D91 1  
D91 C19  C19  C  0 1 N N N 5.474  6.794  23.629 -2.311 -1.182 0.770  C19  D91 2  
D91 N17  N17  N  0 1 N N N 5.049  5.816  21.637 -1.540 1.191  0.730  N17  D91 3  
D91 C16  C16  C  0 1 N N N 5.610  6.790  20.714 -0.762 0.680  -0.397 C16  D91 4  
D91 C15  C15  C  0 1 N N N 6.737  7.403  21.551 -1.694 -0.032 -1.372 C15  D91 5  
D91 N12  N12  N  0 1 N N S 6.234  7.805  22.865 -2.623 -0.968 -0.668 N12  D91 6  
D91 S11  S11  S  0 1 N N N 6.809  9.213  23.705 -4.272 -0.896 -1.103 S11  D91 7  
D91 O13  O13  O  0 1 N N N 7.186  10.227 22.754 -4.729 0.473  -0.993 O13  D91 8  
D91 O14  O14  O  0 1 N N N 5.870  9.461  24.780 -4.979 -1.974 -0.446 O14  D91 9  
D91 C8   C8   C  0 1 Y N N 8.244  8.607  24.558 -4.155 -1.289 -2.820 C8   D91 10 
D91 C9   C9   C  0 1 Y N N 9.543  8.963  23.962 -4.347 -0.524 -3.949 C9   D91 11 
D91 C4   C4   C  0 1 Y N N 10.430 8.359  25.023 -4.121 -1.355 -5.081 C4   D91 12 
D91 C5   C5   C  0 1 Y N N 11.747 8.234  25.205 -4.165 -1.149 -6.474 C5   D91 13 
D91 C6   C6   C  0 1 Y N N 12.204 7.562  26.334 -3.879 -2.218 -7.332 C6   D91 14 
D91 CL   CL   CL 0 0 N N N 13.927 7.468  26.423 -3.930 -1.975 -9.037 CL   D91 15 
D91 C3   C3   C  0 1 Y N N 9.571  7.754  25.998 -3.792 -2.624 -4.599 C3   D91 16 
D91 N7   N7   N  0 1 Y N N 8.310  7.934  25.691 -3.820 -2.555 -3.224 N7   D91 17 
D91 C2   C2   C  0 1 Y N N 10.017 7.134  27.132 -3.503 -3.701 -5.444 C2   D91 18 
D91 C1   C1   C  0 1 Y N N 11.376 7.011  27.331 -3.553 -3.473 -6.822 C1   D91 19 
D91 C20  C20  C  0 1 N N N 5.310  4.436  21.609 -1.596 2.573  0.944  C20  D91 20 
D91 O22  O22  O  0 1 N N N 4.886  3.795  22.567 -1.036 3.424  0.253  O22  D91 21 
D91 C21  C21  C  0 1 Y N N 6.109  3.707  20.621 -2.396 3.084  2.067  C21  D91 22 
D91 N23  N23  N  0 1 Y N N 7.393  4.088  20.443 -1.754 3.216  3.239  N23  D91 23 
D91 C24  C24  C  0 1 Y N N 8.155  3.392  19.598 -2.518 3.687  4.247  C24  D91 24 
D91 C25  C25  C  0 1 Y N N 7.662  2.313  18.890 -3.852 4.012  4.110  C25  D91 25 
D91 C26  C26  C  0 1 Y N N 6.341  1.955  19.143 -4.386 3.828  2.852  C26  D91 26 
D91 N27  N27  N  0 1 Y N N 5.560  2.637  19.998 -3.681 3.362  1.799  N27  D91 27 
D91 C28  C28  C  0 1 Y N N 8.541  1.537  17.981 -4.636 4.512  5.211  C28  D91 28 
D91 C29  C29  C  0 1 Y N N 9.794  1.175  18.458 -4.338 4.131  6.518  C29  D91 29 
D91 C30  C30  C  0 1 Y N N 10.672 0.417  17.674 -5.122 4.640  7.541  C30  D91 30 
D91 N31  N31  N  0 1 Y N N 10.329 -0.010 16.461 -6.160 5.485  7.350  N31  D91 31 
D91 C32  C32  C  0 1 Y N N 9.102  0.321  16.009 -6.422 5.835  6.071  C32  D91 32 
D91 C33  C33  C  0 1 Y N N 8.173  1.081  16.732 -5.699 5.382  4.979  C33  D91 33 
D91 C7   C7   C  0 1 N N N ?      ?      ?      -1.581 -0.055 2.880  C7   D91 34 
D91 C10  C10  C  0 1 N N N ?      ?      ?      -2.368 -0.998 3.801  C10  D91 35 
D91 C11  C11  C  0 1 N N N ?      ?      ?      -3.792 -0.505 4.066  C11  D91 36 
D91 C12  C12  C  0 1 N N N ?      ?      ?      -2.412 -2.397 3.184  C12  D91 37 
D91 H18  H18  H  0 1 N N N 3.539  6.543  23.545 -3.270 0.528  1.690  H18  D91 38 
D91 H191 1H19 H  0 0 N N N 5.105  7.233  24.568 -1.356 -1.718 0.832  H191 D91 39 
D91 H192 2H19 H  0 0 N N N 6.121  5.939  23.874 -3.058 -1.844 1.225  H192 D91 40 
D91 H161 1H16 H  0 0 N N N 5.987  6.319  19.794 -0.000 -0.000 -0.000 H161 D91 41 
D91 H162 2H16 H  0 0 N N N 4.879  7.527  20.350 -0.234 1.487  -0.914 H162 D91 42 
D91 H151 1H15 H  0 0 N N N 7.536  6.658  21.682 -2.280 0.717  -1.918 H151 D91 43 
D91 H152 2H15 H  0 0 N N N 7.127  8.290  21.031 -1.115 -0.599 -2.108 H152 D91 44 
D91 H9   H9   H  0 1 N N N 9.785  9.491  23.051 -4.623 0.522  -3.957 H9   D91 45 
D91 H5   H5   H  0 1 N N N 12.443 8.646  24.490 -4.419 -0.169 -6.870 H5   D91 46 
D91 HN7  HN7  H  0 1 N N N 7.528  7.615  26.226 -3.620 -3.328 -2.605 HN7  D91 47 
D91 H2   H2   H  0 1 N N N 9.318  6.748  27.859 -3.251 -4.679 -5.048 H2   D91 48 
D91 H1   H1   H  0 1 N N N 11.783 6.520  28.203 -3.333 -4.300 -7.495 H1   D91 49 
D91 H24  H24  H  0 1 N N N 9.187  3.680  19.463 -1.999 3.794  5.195  H24  D91 50 
D91 H26  H26  H  0 1 N N N 5.928  1.097  18.633 -5.426 4.053  2.635  H26  D91 51 
D91 H29  H29  H  0 1 N N N 10.096 1.483  19.448 -3.519 3.455  6.741  H29  D91 52 
D91 H30  H30  H  0 1 N N N 11.650 0.173  18.062 -4.929 4.372  8.574  H30  D91 53 
D91 H32  H32  H  0 1 N N N 8.817  -0.022 15.025 -7.259 6.513  5.941  H32  D91 54 
D91 H33  H33  H  0 1 N N N 7.198  1.303  16.324 -5.963 5.704  3.977  H33  D91 55 
D91 H71  1H7  H  0 1 N N N ?      ?      ?      -0.570 -0.438 2.713  H71  D91 56 
D91 H72  2H7  H  0 1 N N N ?      ?      ?      -1.481 0.923  3.358  H72  D91 57 
D91 H10  H10  H  0 1 N N N ?      ?      ?      -1.846 -1.071 4.764  H10  D91 58 
D91 H111 1H11 H  0 0 N N N ?      ?      ?      -4.340 -0.355 3.130  H111 D91 59 
D91 H112 2H11 H  0 0 N N N ?      ?      ?      -3.790 0.441  4.616  H112 D91 60 
D91 H113 3H11 H  0 0 N N N ?      ?      ?      -4.347 -1.230 4.671  H113 D91 61 
D91 H121 1H12 H  0 0 N N N ?      ?      ?      -2.928 -2.390 2.218  H121 D91 62 
D91 H122 2H12 H  0 0 N N N ?      ?      ?      -2.936 -3.097 3.843  H122 D91 63 
D91 H123 3H12 H  0 0 N N N ?      ?      ?      -1.400 -2.785 3.025  H123 D91 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 
D91 C18 C19  SING N N 1  
D91 C18 N17  SING N N 2  
D91 C18 C7   SING N N 3  
D91 C18 H18  SING N N 4  
D91 C19 N12  SING N N 5  
D91 C19 H191 SING N N 6  
D91 C19 H192 SING N N 7  
D91 N17 C16  SING N N 8  
D91 N17 C20  SING N N 9  
D91 C16 C15  SING N N 10 
D91 C16 H161 SING N N 11 
D91 C16 H162 SING N N 12 
D91 C15 N12  SING N N 13 
D91 C15 H151 SING N N 14 
D91 C15 H152 SING N N 15 
D91 N12 S11  SING N N 16 
D91 S11 O13  DOUB N N 17 
D91 S11 O14  DOUB N N 18 
D91 S11 C8   SING N N 19 
D91 C8  C9   DOUB Y N 20 
D91 C8  N7   SING Y N 21 
D91 C9  C4   SING Y N 22 
D91 C9  H9   SING N N 23 
D91 C4  C5   DOUB Y N 24 
D91 C4  C3   SING Y N 25 
D91 C5  C6   SING Y N 26 
D91 C5  H5   SING N N 27 
D91 C6  CL   SING N N 28 
D91 C6  C1   DOUB Y N 29 
D91 C3  N7   SING Y N 30 
D91 C3  C2   DOUB Y N 31 
D91 N7  HN7  SING N N 32 
D91 C2  C1   SING Y N 33 
D91 C2  H2   SING N N 34 
D91 C1  H1   SING N N 35 
D91 C20 O22  DOUB N N 36 
D91 C20 C21  SING N N 37 
D91 C21 N23  DOUB Y N 38 
D91 C21 N27  SING Y N 39 
D91 N23 C24  SING Y N 40 
D91 C24 C25  DOUB Y N 41 
D91 C24 H24  SING N N 42 
D91 C25 C26  SING Y N 43 
D91 C25 C28  SING N N 44 
D91 C26 N27  DOUB Y N 45 
D91 C26 H26  SING N N 46 
D91 C28 C29  DOUB Y N 47 
D91 C28 C33  SING Y N 48 
D91 C29 C30  SING Y N 49 
D91 C29 H29  SING N N 50 
D91 C30 N31  DOUB Y N 51 
D91 C30 H30  SING N N 52 
D91 N31 C32  SING Y N 53 
D91 C32 C33  DOUB Y N 54 
D91 C32 H32  SING N N 55 
D91 C33 H33  SING N N 56 
D91 C7  C10  SING N N 57 
D91 C7  H71  SING N N 58 
D91 C7  H72  SING N N 59 
D91 C10 C11  SING N N 60 
D91 C10 C12  SING N N 61 
D91 C10 H10  SING N N 62 
D91 C11 H111 SING N N 63 
D91 C11 H112 SING N N 64 
D91 C11 H113 SING N N 65 
D91 C12 H121 SING N N 66 
D91 C12 H122 SING N N 67 
D91 C12 H123 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 
D91 SMILES           ACDLabs              10.04 O=S(=O)(c2cc1cc(Cl)ccc1n2)N5CCN(C(=O)c4ncc(c3ccncc3)cn4)C(CC(C)C)C5                                                                                                                         
D91 InChI            InChI                1.02b InChI=1/C26H27ClN6O3S/c1-17(2)11-22-16-32(37(35,36)24-13-19-12-21(27)3-4-23(19)31-24)9-10-33(22)26(34)25-29-14-20(15-30-25)18-5-7-28-8-6-18/h3-8,12-15,17,22,31H,9-11,16H2,1-2H3/t22-/m1/s1 
D91 InChIKey         InChI                1.02b JUUFKVAFKAKWRV-JOCHJYFZBD                                                                                                                                                                   
D91 SMILES_CANONICAL CACTVS               3.341 CC(C)C[C@@H]1CN(CCN1C(=O)c2ncc(cn2)c3ccncc3)[S](=O)(=O)c4[nH]c5ccc(Cl)cc5c4                                                                                                                 
D91 SMILES           CACTVS               3.341 CC(C)C[CH]1CN(CCN1C(=O)c2ncc(cn2)c3ccncc3)[S](=O)(=O)c4[nH]c5ccc(Cl)cc5c4                                                                                                                   
D91 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(C)C[C@@H]1C[N@](CCN1C(=O)c2ncc(cn2)c3ccncc3)S(=O)(=O)c4cc5cc(ccc5[nH]4)Cl                                                                                                                
D91 SMILES           "OpenEye OEToolkits" 1.5.0 CC(C)CC1CN(CCN1C(=O)c2ncc(cn2)c3ccncc3)S(=O)(=O)c4cc5cc(ccc5[nH]4)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 
D91 "SYSTEMATIC NAME" ACDLabs              10.04 5-chloro-2-({(3R)-3-(2-methylpropyl)-4-[(5-pyridin-4-ylpyrimidin-2-yl)carbonyl]piperazin-1-yl}sulfonyl)-1H-indole       
D91 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 [(2R,4S)-4-[(5-chloro-1H-indol-2-yl)sulfonyl]-2-(2-methylpropyl)piperazin-1-yl]-(5-pyridin-4-ylpyrimidin-2-yl)methanone 
# 
