data_GB8
# 
_chem_comp.id                                    GB8 
_chem_comp.name                                  "(2R,3R,4S,5R)-2-(6-amino-8-((quinolin-7-ylmethyl)amino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H21 N7 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2015-09-24 
_chem_comp.pdbx_modified_date                    2016-05-06 
_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                        423.425 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GB8 
_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        5ar0 
_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 
GB8 C    C    C 0 1 N N R 6.338 7.698  -8.363  1.607  1.048  0.056  C    GB8 1  
GB8 N    N    N 0 1 Y N N 5.052 8.340  -8.162  1.647  -0.416 0.020  N    GB8 2  
GB8 O    O    O 0 1 N N N 6.419 6.584  -7.503  2.516  1.600  -0.921 O    GB8 3  
GB8 C1   C1   C 0 1 N N R 7.546 8.557  -8.021  2.125  1.567  1.416  C1   GB8 4  
GB8 N1   N1   N 0 1 Y N N 3.438 9.567  -7.179  0.975  -2.500 0.013  N1   GB8 5  
GB8 O1   O1   O 0 1 N N N 7.546 7.423  -5.044  3.908  3.605  -2.512 O1   GB8 6  
GB8 C2   C2   C 0 1 N N S 8.604 7.472  -7.837  2.910  2.848  1.054  C2   GB8 7  
GB8 N2   N2   N 0 1 Y N N 4.188 8.313  -10.443 4.078  -0.953 -0.153 N2   GB8 8  
GB8 O2   O2   O 0 1 N N N 9.148 7.077  -9.088  2.326  3.989  1.687  O2   GB8 9  
GB8 C3   C3   C 0 1 N N R 7.808 6.339  -7.184  2.772  2.952  -0.481 C3   GB8 10 
GB8 N3   N3   N 0 1 Y N N 2.162 9.591  -10.659 4.571  -3.210 -0.237 N3   GB8 11 
GB8 O3   O3   O 0 1 N N N 7.858 9.466  -9.068  1.033  1.877  2.283  O3   GB8 12 
GB8 C4   C4   C 0 1 N N N 7.965 6.234  -5.686  4.070  3.476  -1.098 C4   GB8 13 
GB8 N4   N4   N 0 1 N N N 1.182 10.738 -8.918  2.908  -4.883 -0.160 N4   GB8 14 
GB8 C5   C5   C 0 1 Y N N 4.561 8.925  -6.954  0.569  -1.256 0.066  C5   GB8 15 
GB8 N5   N5   N 0 1 N N N 5.161 8.822  -5.762  -0.749 -0.854 0.156  N5   GB8 16 
GB8 C6   C6   C 0 1 Y N N 3.168 9.415  -8.532  2.329  -2.529 -0.073 C6   GB8 17 
GB8 N6   N6   N 0 1 Y N N 7.302 14.403 -3.641  -6.790 0.738  0.610  N6   GB8 18 
GB8 C7   C7   C 0 1 Y N N 4.139 8.649  -9.149  2.775  -1.197 -0.072 C7   GB8 19 
GB8 C8   C8   C 0 1 Y N N 3.156 8.827  -11.112 4.943  -1.943 -0.232 C8   GB8 20 
GB8 C9   C9   C 0 1 Y N N 2.138 9.919  -9.350  3.289  -3.550 -0.155 C9   GB8 21 
GB8 C10  C10  C 0 1 N N N 4.612 9.491  -4.595  -1.819 -1.854 0.197  C10  GB8 22 
GB8 C11  C11  C 0 1 Y N N 5.310 10.800 -4.326  -3.152 -1.159 0.295  C11  GB8 23 
GB8 C12  C12  C 0 1 Y N N 4.598 11.894 -3.907  -3.818 -0.822 -0.844 C12  GB8 24 
GB8 C13  C13  C 0 1 Y N N 5.229 13.135 -3.661  -5.061 -0.174 -0.754 C13  GB8 25 
GB8 C14  C14  C 0 1 Y N N 6.620 13.234 -3.864  -5.607 0.121  0.520  C14  GB8 26 
GB8 C15  C15  C 0 1 Y N N 7.327 12.093 -4.296  -4.889 -0.244 1.672  C15  GB8 27 
GB8 C16  C16  C 0 1 Y N N 6.679 10.919 -4.515  -3.687 -0.871 1.549  C16  GB8 28 
GB8 C17  C17  C 0 1 Y N N 6.602 15.444 -3.218  -7.463 1.080  -0.461 C17  GB8 29 
GB8 C18  C18  C 0 1 Y N N 5.238 15.430 -2.990  -6.984 0.820  -1.743 C18  GB8 30 
GB8 C19  C19  C 0 1 Y N N 4.550 14.281 -3.211  -5.781 0.192  -1.906 C19  GB8 31 
GB8 H    H    H 0 1 N N N 6.425 7.373  -9.410  0.592  1.404  -0.126 H    GB8 32 
GB8 H1   H1   H 0 1 N N N 7.377 9.082  -7.069  2.785  0.833  1.878  H1   GB8 33 
GB8 HO1  HO1  H 0 1 N N N 7.655 7.331  -4.105  4.694  3.932  -2.970 HO1  GB8 34 
GB8 H2   H2   H 0 1 N N N 9.387 7.824  -7.149  3.957  2.749  1.340  H2   GB8 35 
GB8 HO2  HO2  H 0 1 N N N 9.803 6.403  -8.950  2.779  4.821  1.494  HO2  GB8 36 
GB8 H3   H3   H 0 1 N N N 8.125 5.388  -7.637  1.937  3.601  -0.744 H3   GB8 37 
GB8 HO3  HO3  H 0 1 N N N 8.615 9.985  -8.822  1.302  2.207  3.151  HO3  GB8 38 
GB8 H4   H4   H 0 1 N N N 9.023 6.051  -5.448  4.880  2.777  -0.888 H4   GB8 39 
GB8 H4A  H4A  H 0 1 N N N 7.356 5.394  -5.319  4.309  4.449  -0.670 H4A  GB8 40 
GB8 HN4  HN4  H 0 1 N N N 0.594 10.998 -9.684  3.580  -5.579 -0.223 HN4  GB8 41 
GB8 HN4A HN4A H 0 0 N N N 0.636 10.274 -8.221  1.969  -5.119 -0.100 HN4A GB8 42 
GB8 HN5  HN5  H 0 1 N N N 5.195 7.847  -5.543  -0.966 0.090  0.191  HN5  GB8 43 
GB8 H8   H8   H 0 1 N N N 3.120 8.592  -12.166 5.996  -1.710 -0.297 H8   GB8 44 
GB8 H10  H10  H 0 1 N N N 3.543 9.685  -4.765  -1.788 -2.457 -0.711 H10  GB8 45 
GB8 H10A H10A H 0 0 N N N 4.731 8.836  -3.719  -1.680 -2.498 1.066  H10A GB8 46 
GB8 H12  H12  H 0 1 N N N 3.531 11.806 -3.762  -3.393 -1.050 -1.810 H12  GB8 47 
GB8 H15  H15  H 0 1 N N N 8.394 12.153 -4.454  -5.289 -0.027 2.652  H15  GB8 48 
GB8 H16  H16  H 0 1 N N N 7.243 10.059 -4.844  -3.140 -1.149 2.437  H16  GB8 49 
GB8 H17  H17  H 0 1 N N N 7.132 16.367 -3.039  -8.415 1.577  -0.347 H17  GB8 50 
GB8 H18  H18  H 0 1 N N N 4.730 16.317 -2.642  -7.562 1.114  -2.606 H18  GB8 51 
GB8 H19  H19  H 0 1 N N N 3.484 14.247 -3.042  -5.395 -0.017 -2.893 H19  GB8 52 
# 
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 
GB8 C   N    SING N N 1  
GB8 C   O    SING N N 2  
GB8 C   C1   SING N N 3  
GB8 N   C5   SING Y N 4  
GB8 N   C7   SING Y N 5  
GB8 O   C3   SING N N 6  
GB8 C1  C2   SING N N 7  
GB8 C1  O3   SING N N 8  
GB8 N1  C5   DOUB Y N 9  
GB8 N1  C6   SING Y N 10 
GB8 O1  C4   SING N N 11 
GB8 C2  O2   SING N N 12 
GB8 C2  C3   SING N N 13 
GB8 N2  C7   DOUB Y N 14 
GB8 N2  C8   SING Y N 15 
GB8 C3  C4   SING N N 16 
GB8 N3  C8   DOUB Y N 17 
GB8 N3  C9   SING Y N 18 
GB8 N4  C9   SING N N 19 
GB8 C5  N5   SING N N 20 
GB8 N5  C10  SING N N 21 
GB8 C6  C7   SING Y N 22 
GB8 C6  C9   DOUB Y N 23 
GB8 N6  C14  DOUB Y N 24 
GB8 N6  C17  SING Y N 25 
GB8 C10 C11  SING N N 26 
GB8 C11 C12  DOUB Y N 27 
GB8 C11 C16  SING Y N 28 
GB8 C12 C13  SING Y N 29 
GB8 C13 C14  SING Y N 30 
GB8 C13 C19  DOUB Y N 31 
GB8 C14 C15  SING Y N 32 
GB8 C15 C16  DOUB Y N 33 
GB8 C17 C18  DOUB Y N 34 
GB8 C18 C19  SING Y N 35 
GB8 C   H    SING N N 36 
GB8 C1  H1   SING N N 37 
GB8 O1  HO1  SING N N 38 
GB8 C2  H2   SING N N 39 
GB8 O2  HO2  SING N N 40 
GB8 C3  H3   SING N N 41 
GB8 O3  HO3  SING N N 42 
GB8 C4  H4   SING N N 43 
GB8 C4  H4A  SING N N 44 
GB8 N4  HN4  SING N N 45 
GB8 N4  HN4A SING N N 46 
GB8 N5  HN5  SING N N 47 
GB8 C8  H8   SING N N 48 
GB8 C10 H10  SING N N 49 
GB8 C10 H10A SING N N 50 
GB8 C12 H12  SING N N 51 
GB8 C15 H15  SING N N 52 
GB8 C16 H16  SING N N 53 
GB8 C17 H17  SING N N 54 
GB8 C18 H18  SING N N 55 
GB8 C19 H19  SING N N 56 
# 
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 
GB8 InChI            InChI                1.03  "InChI=1S/C20H21N7O4/c21-17-14-18(25-9-24-17)27(19-16(30)15(29)13(8-28)31-19)20(26-14)23-7-10-3-4-12-11(6-10)2-1-5-22-12/h1-6,9,13,15-16,19,28-30H,7-8H2,(H,23,26)(H2,21,24,25)/t13-,15-,16-,19-/m1/s1" 
GB8 InChIKey         InChI                1.03  ZPAVHMFARWZWPX-NVQRDWNXSA-N                                                                                                                                                                             
GB8 SMILES_CANONICAL CACTVS               3.385 "Nc1ncnc2n([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c(NCc4ccc5ncccc5c4)nc12"                                                                                                                                   
GB8 SMILES           CACTVS               3.385 "Nc1ncnc2n([CH]3O[CH](CO)[CH](O)[CH]3O)c(NCc4ccc5ncccc5c4)nc12"                                                                                                                                         
GB8 SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "c1cc2cc(ccc2nc1)CNc3nc4c(ncnc4n3[C@H]5[C@@H]([C@@H]([C@H](O5)CO)O)O)N"                                                                                                                                 
GB8 SMILES           "OpenEye OEToolkits" 1.7.6 "c1cc2cc(ccc2nc1)CNc3nc4c(ncnc4n3C5C(C(C(O5)CO)O)O)N"                                                                                                                                                   
# 
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 
GB8 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "(2R,3R,4S,5R)-2-[6-azanyl-8-(quinolin-6-ylmethylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
GB8 "Create component" 2015-09-24 EBI  
GB8 "Initial release"  2016-05-11 RCSB 
# 
