data_GD9
# 
_chem_comp.id                                    GD9 
_chem_comp.name                                  2-(1H-indazol-4-yl)-6-{[4-(methylsulfonyl)piperazin-1-yl]methyl}-4-morpholin-4-yl-thieno[3,2-d]pyrimidine 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H27 N7 O3 S2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-06-03 
_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                        513.636 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GD9 
_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        3DBS 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBJ 
# 
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 
GD9 O3   O3   O 0 1 N N N 19.686 59.525 24.439 -2.010 5.534  -0.883 O3   GD9 1  
GD9 C4   C4   C 0 1 Y N N 22.255 61.781 22.108 -2.161 1.643  0.424  C4   GD9 2  
GD9 C5   C5   C 0 1 Y N N 21.375 65.398 21.367 0.953  -0.381 1.714  C5   GD9 3  
GD9 C6   C6   C 0 1 Y N N 22.592 65.205 20.863 -0.043 -1.193 1.400  C6   GD9 4  
GD9 N1   N1   N 0 1 Y N N 24.157 63.285 20.755 -2.413 -1.056 0.506  N1   GD9 5  
GD9 C7   C7   C 0 1 N N N 20.691 66.743 21.278 2.290  -0.839 2.237  C7   GD9 6  
GD9 C8   C8   C 0 1 Y N N 25.609 61.469 20.667 -4.665 -0.905 -0.343 C8   GD9 7  
GD9 N2   N2   N 0 1 Y N N 23.448 61.257 21.720 -3.283 1.045  0.051  N2   GD9 8  
GD9 C9   C9   C 0 1 N N N 19.921 68.393 19.672 4.432  -1.742 1.558  C9   GD9 9  
GD9 C10  C10  C 0 1 N N N 19.530 68.524 18.196 5.272  -2.130 0.337  C10  GD9 10 
GD9 C11  C11  C 0 1 N N N 18.885 66.207 18.208 4.308  -0.127 -0.860 C11  GD9 11 
GD9 C12  C12  C 0 1 N N N 18.981 66.172 19.714 3.505  0.182  0.408  C12  GD9 12 
GD9 N3   N3   N 0 1 N N N 21.380 60.990 22.810 -2.050 3.023  0.375  N3   GD9 13 
GD9 C13  C13  C 0 1 N N N 17.257 69.177 15.870 7.225  -1.335 -2.568 C13  GD9 14 
GD9 C14  C14  C 0 1 N N N 21.950 59.888 23.583 -3.292 3.634  -0.120 C14  GD9 15 
GD9 C15  C15  C 0 1 N N N 21.062 59.602 24.789 -3.148 5.158  -0.102 C15  GD9 16 
GD9 N4   N4   N 0 1 N N N 20.161 66.980 19.955 3.203  -1.073 1.110  N4   GD9 17 
GD9 O2   O2   O 0 1 N N N 19.233 67.342 15.453 7.863  -1.047 0.007  O2   GD9 18 
GD9 S2   S2   S 0 1 N N N 18.013 67.564 16.242 7.002  -0.491 -0.977 S2   GD9 19 
GD9 O1   O1   O 0 1 N N N 17.038 66.497 15.981 6.918  0.915  -1.166 O1   GD9 20 
GD9 N5   N5   N 0 1 N N N 18.472 67.555 17.898 5.483  -0.929 -0.486 N5   GD9 21 
GD9 S1   S1   S 0 1 Y N N 20.661 64.068 22.110 0.520  1.296  1.437  S1   GD9 22 
GD9 C2   C2   C 0 1 Y N N 22.993 63.829 21.110 -1.237 -0.532 0.916  C2   GD9 23 
GD9 C1   C1   C 0 1 Y N N 22.032 63.123 21.786 -1.086 0.856  0.876  C1   GD9 24 
GD9 C3   C3   C 0 1 Y N N 24.375 61.989 21.052 -3.396 -0.280 0.095  C3   GD9 25 
GD9 C18  C18  C 0 1 Y N N 26.254 61.914 19.517 -5.718 -0.116 -0.781 C18  GD9 26 
GD9 C19  C19  C 0 1 Y N N 27.490 61.382 19.182 -6.907 -0.698 -1.192 C19  GD9 27 
GD9 C20  C20  C 0 1 Y N N 28.088 60.437 19.990 -7.065 -2.066 -1.174 C20  GD9 28 
GD9 C21  C21  C 0 1 Y N N 27.454 60.012 21.141 -6.025 -2.884 -0.739 C21  GD9 29 
GD9 N6   N6   N 0 1 Y N N 27.863 59.090 22.079 -5.879 -4.241 -0.608 N6   GD9 30 
GD9 C22  C22  C 0 1 Y N N 26.251 60.535 21.438 -4.810 -2.308 -0.324 C22  GD9 31 
GD9 C23  C23  C 0 1 Y N N 25.828 59.920 22.652 -3.956 -3.371 0.048  C23  GD9 32 
GD9 N7   N7   N 0 1 Y N N 26.803 59.061 23.031 -4.594 -4.495 -0.113 N7   GD9 33 
GD9 C16  C16  C 0 1 N N N 19.250 60.743 23.850 -0.783 4.957  -0.428 C16  GD9 34 
GD9 C17  C17  C 0 1 N N N 19.955 60.889 22.500 -0.904 3.431  -0.450 C17  GD9 35 
GD9 H6   H6   H 0 1 N N N 23.185 65.950 20.353 0.029  -2.266 1.497  H6   GD9 36 
GD9 H7   H7   H 0 1 N N N 19.863 66.768 22.002 2.707  -0.071 2.889  H7   GD9 37 
GD9 H7A  H7A  H 0 1 N N N 21.433 67.524 21.499 2.163  -1.763 2.800  H7A  GD9 38 
GD9 H9   H9   H 0 1 N N N 20.833 68.975 19.871 4.173  -2.639 2.121  H9   GD9 39 
GD9 H9A  H9A  H 0 1 N N N 19.115 68.778 20.314 5.003  -1.066 2.193  H9A  GD9 40 
GD9 H10  H10  H 0 1 N N N 19.165 69.543 17.999 6.235  -2.522 0.665  H10  GD9 41 
GD9 H10A H10A H 0 0 N N N 20.405 68.327 17.560 4.745  -2.885 -0.246 H10A GD9 42 
GD9 H11  H11  H 0 1 N N N 19.855 65.974 17.744 3.688  -0.690 -1.558 H11  GD9 43 
GD9 H11A H11A H 0 0 N N N 18.178 65.458 17.821 4.633  0.804  -1.324 H11A GD9 44 
GD9 H12  H12  H 0 1 N N N 18.086 66.592 20.196 4.090  0.831  1.059  H12  GD9 45 
GD9 H12A H12A H 0 0 N N N 19.048 65.156 20.130 2.574  0.680  0.137  H12A GD9 46 
GD9 H13  H13  H 0 1 N N N 17.104 69.735 16.805 7.139  -2.412 -2.422 H13  GD9 47 
GD9 H13A H13A H 0 0 N N N 17.922 69.749 15.206 6.459  -1.000 -3.267 H13A GD9 48 
GD9 H13B H13B H 0 0 N N N 16.288 69.022 15.374 8.211  -1.100 -2.969 H13B GD9 49 
GD9 H14  H14  H 0 1 N N N 22.011 58.990 22.951 -3.481 3.299  -1.140 H14  GD9 50 
GD9 H14A H14A H 0 0 N N N 22.958 60.163 23.926 -4.123 3.339  0.520  H14A GD9 51 
GD9 H15  H15  H 0 1 N N N 21.192 60.414 25.520 -3.012 5.498  0.925  H15  GD9 52 
GD9 H15A H15A H 0 0 N N N 21.360 58.629 25.205 -4.044 5.614  -0.522 H15A GD9 53 
GD9 H18  H18  H 0 1 N N N 25.796 62.666 18.892 -5.611 0.959  -0.801 H18  GD9 54 
GD9 H19  H19  H 0 1 N N N 27.988 61.710 18.282 -7.719 -0.072 -1.531 H19  GD9 55 
GD9 H20  H20  H 0 1 N N N 29.052 60.030 19.722 -7.997 -2.505 -1.497 H20  GD9 56 
GD9 HN6  HN6  H 0 1 N N N 28.711 58.561 22.090 -6.550 -4.910 -0.820 HN6  GD9 57 
GD9 H23  H23  H 0 1 N N N 24.901 60.105 23.173 -2.947 -3.267 0.417  H23  GD9 58 
GD9 H16  H16  H 0 1 N N N 18.160 60.722 23.705 0.030  5.267  -1.084 H16  GD9 59 
GD9 H16A H16A H 0 0 N N N 19.494 61.594 24.504 -0.579 5.291  0.589  H16A GD9 60 
GD9 H17  H17  H 0 1 N N N 19.606 61.789 21.972 0.008  2.987  -0.051 H17  GD9 61 
GD9 H17A H17A H 0 0 N N N 19.744 60.036 21.838 -1.055 3.092  -1.475 H17A GD9 62 
# 
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 
GD9 O3  C15  SING N N 1  
GD9 O3  C16  SING N N 2  
GD9 C4  N2   DOUB Y N 3  
GD9 C4  N3   SING N N 4  
GD9 C4  C1   SING Y N 5  
GD9 C5  C6   DOUB Y N 6  
GD9 C5  C7   SING N N 7  
GD9 C5  S1   SING Y N 8  
GD9 C6  C2   SING Y N 9  
GD9 N1  C2   SING N N 10 
GD9 N1  C3   DOUB Y N 11 
GD9 C7  N4   SING Y N 12 
GD9 C8  C3   SING N N 13 
GD9 C8  C18  DOUB N N 14 
GD9 C8  C22  SING N N 15 
GD9 N2  C3   SING N N 16 
GD9 C9  C10  SING Y N 17 
GD9 C9  N4   SING Y N 18 
GD9 C10 N5   SING Y N 19 
GD9 C11 C12  SING N N 20 
GD9 C11 N5   SING N N 21 
GD9 C12 N4   SING N N 22 
GD9 N3  C14  SING N N 23 
GD9 N3  C17  SING N N 24 
GD9 C13 S2   SING N N 25 
GD9 C14 C15  SING N N 26 
GD9 O2  S2   DOUB N N 27 
GD9 S2  O1   DOUB N N 28 
GD9 S2  N5   SING N N 29 
GD9 S1  C1   SING N N 30 
GD9 C2  C1   DOUB N N 31 
GD9 C18 C19  SING N N 32 
GD9 C19 C20  DOUB N N 33 
GD9 C20 C21  SING N N 34 
GD9 C21 N6   SING N N 35 
GD9 C21 C22  DOUB N N 36 
GD9 N6  N7   SING N N 37 
GD9 C22 C23  SING N N 38 
GD9 C23 N7   DOUB N N 39 
GD9 C16 C17  SING N N 40 
GD9 C6  H6   SING N N 41 
GD9 C7  H7   SING N N 42 
GD9 C7  H7A  SING N N 43 
GD9 C9  H9   SING N N 44 
GD9 C9  H9A  SING N N 45 
GD9 C10 H10  SING N N 46 
GD9 C10 H10A SING N N 47 
GD9 C11 H11  SING Y N 48 
GD9 C11 H11A SING Y N 49 
GD9 C12 H12  SING Y N 50 
GD9 C12 H12A SING N N 51 
GD9 C13 H13  SING Y N 52 
GD9 C13 H13A SING N N 53 
GD9 C13 H13B SING Y N 54 
GD9 C14 H14  SING N N 55 
GD9 C14 H14A SING Y N 56 
GD9 C15 H15  SING Y N 57 
GD9 C15 H15A SING Y N 58 
GD9 C18 H18  SING N N 59 
GD9 C19 H19  SING Y N 60 
GD9 C20 H20  SING Y N 61 
GD9 N6  HN6  SING N N 62 
GD9 C23 H23  SING N N 63 
GD9 C16 H16  SING N N 64 
GD9 C16 H16A SING N N 65 
GD9 C17 H17  SING N N 66 
GD9 C17 H17A SING N N 67 
# 
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 
GD9 SMILES           ACDLabs              10.04 O=S(=O)(N1CCN(CC1)Cc3sc2c(nc(nc2c3)c5cccc4nncc45)N6CCOCC6)C                                                                                                                        
GD9 InChI            InChI                1.02b InChI=1/C23H27N7O3S2/c1-35(31,32)30-7-5-28(6-8-30)15-16-13-20-21(34-16)23(29-9-11-33-12-10-29)26-22(25-20)17-3-2-4-19-18(17)14-24-27-19/h2-4,13-14H,5-12,15H2,1H3,(H,24,27)/f/h27H 
GD9 InChIKey         InChI                1.02b LHNIIDJUOCFXAP-LELJVTLKCB                                                                                                                                                          
GD9 SMILES_CANONICAL CACTVS               3.341 C[S](=O)(=O)N1CCN(CC1)Cc2sc3c(c2)nc(nc3N4CCOCC4)c5cccc6[nH]ncc56                                                                                                                   
GD9 SMILES           CACTVS               3.341 C[S](=O)(=O)N1CCN(CC1)Cc2sc3c(c2)nc(nc3N4CCOCC4)c5cccc6[nH]ncc56                                                                                                                   
GD9 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CS(=O)(=O)N1CCN(CC1)Cc2cc3c(s2)c(nc(n3)c4cccc5c4cn[nH]5)N6CCOCC6                                                                                                                   
GD9 SMILES           "OpenEye OEToolkits" 1.5.0 CS(=O)(=O)N1CCN(CC1)Cc2cc3c(s2)c(nc(n3)c4cccc5c4cn[nH]5)N6CCOCC6                                                                                                                   
# 
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 
GD9 "SYSTEMATIC NAME" ACDLabs              10.04 2-(1H-indazol-4-yl)-6-{[4-(methylsulfonyl)piperazin-1-yl]methyl}-4-morpholin-4-ylthieno[3,2-d]pyrimidine 
GD9 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 2-(1H-indazol-4-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-yl-thieno[2,3-e]pyrimidine  
# 
