data_8GN
# 
_chem_comp.id                                    8GN 
_chem_comp.name                                  "~{N}-[5-[[3-cyano-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-[(3~{R})-3-(dimethylamino)pyrrolidin-1-yl]phenyl]ethanamide" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C24 H29 N9 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2017-02-06 
_chem_comp.pdbx_modified_date                    2017-05-12 
_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                        459.547 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     8GN 
_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        5N20 
_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 
8GN C1  C1  C 0 1 N N N 14.991 -0.169 9.294  -2.511 4.054  1.137  C1  8GN 1  
8GN C2  C2  C 0 1 Y N N 16.174 -2.199 10.273 -2.075 2.060  -0.090 C2  8GN 2  
8GN C3  C3  C 0 1 Y N N 16.567 -1.665 11.501 -0.711 2.305  -0.103 C3  8GN 3  
8GN N6  N1  N 0 1 Y N N 14.446 -0.667 17.849 4.790  -2.700 0.518  N6  8GN 4  
8GN C7  C4  C 0 1 Y N N 16.604 -3.488 9.909  -2.564 0.828  -0.522 C7  8GN 5  
8GN C8  C5  C 0 1 N N N 16.829 -3.505 7.360  -4.439 0.276  -1.870 C8  8GN 6  
8GN C9  C6  C 0 1 N N N 16.641 -4.665 6.393  -5.570 -0.758 -1.720 C9  8GN 7  
8GN C10 C7  C 0 1 N N R 15.347 -5.307 6.903  -5.658 -1.043 -0.203 C10 8GN 8  
8GN C11 C8  C 0 1 N N N 15.547 -5.269 8.414  -4.258 -0.621 0.310  C11 8GN 9  
8GN C12 C9  C 0 1 N N N 14.197 -6.533 5.049  -5.883 -2.766 1.483  C12 8GN 10 
8GN C13 C10 C 0 1 N N N 16.001 -7.647 6.202  -7.150 -2.914 -0.575 C13 8GN 11 
8GN C14 C11 C 0 1 Y N N 16.773 -1.624 14.702 2.433  0.541  -0.304 C14 8GN 12 
8GN C15 C12 C 0 1 Y N N 15.410 -1.888 14.544 3.812  0.763  -0.418 C15 8GN 13 
8GN C16 C13 C 0 1 Y N N 14.525 -1.596 15.581 4.676  -0.264 -0.162 C16 8GN 14 
8GN C19 C14 C 0 1 Y N N 15.414 -0.135 18.582 3.880  -3.593 0.803  C19 8GN 15 
8GN C20 C15 C 0 1 N N N 17.896 0.426  18.347 1.346  -3.632 0.910  C20 8GN 16 
8GN C21 C16 C 0 1 N N N 12.548 -2.242 14.253 6.572  1.264  -0.533 C21 8GN 17 
8GN C22 C17 C 0 1 N N N 11.269 -3.002 14.366 7.953  1.356  -1.185 C22 8GN 18 
8GN N7  N2  N 0 1 N N N 18.923 0.850  18.609 0.343  -4.135 1.089  N7  8GN 19 
8GN C18 C18 C 0 1 Y N N 16.653 -0.137 17.928 2.609  -2.998 0.684  C18 8GN 20 
8GN N4  N3  N 0 1 Y N N 15.055 -1.024 16.707 4.171  -1.486 0.201  N4  8GN 21 
8GN N8  N4  N 0 1 N N N 13.205 -1.792 15.483 6.037  -0.074 -0.267 N8  8GN 22 
8GN C23 C19 C 0 1 N N N 12.415 -3.711 14.025 7.778  1.719  0.291  C23 8GN 23 
8GN C17 C20 C 0 1 Y N N 16.407 -0.739 16.726 2.819  -1.659 0.300  C17 8GN 24 
8GN N5  N5  N 0 1 Y N N 17.275 -1.029 15.767 1.980  -0.654 0.049  N5  8GN 25 
8GN N3  N6  N 0 1 N N N 17.615 -2.041 13.699 1.543  1.570  -0.559 N3  8GN 26 
8GN C4  C21 C 0 1 Y N N 17.408 -2.377 12.352 0.165  1.324  -0.546 C4  8GN 27 
8GN C5  C22 C 0 1 Y N N 17.836 -3.646 11.982 -0.325 0.097  -0.975 C5  8GN 28 
8GN C6  C23 C 0 1 Y N N 17.417 -4.206 10.786 -1.684 -0.149 -0.963 C6  8GN 29 
8GN N   N7  N 0 1 N N N 15.428 -1.457 9.317  -2.961 3.048  0.362  N   8GN 30 
8GN O   O1  O 0 1 N N N 15.096 0.596  10.246 -1.361 4.054  1.523  O   8GN 31 
8GN C   C24 C 0 1 N N N 14.398 0.268  7.988  -3.434 5.182  1.519  C   8GN 32 
8GN N1  N8  N 0 1 N N N 16.273 -4.013 8.620  -3.943 0.577  -0.509 N1  8GN 33 
8GN N2  N9  N 0 1 N N N 14.920 -6.659 6.315  -5.893 -2.472 0.044  N2  8GN 34 
8GN H1  H1  H 0 1 N N N 16.214 -0.687 11.795 -0.330 3.259  0.231  H1  8GN 35 
8GN H2  H2  H 0 1 N N N 17.895 -3.256 7.473  -3.634 -0.139 -2.476 H2  8GN 36 
8GN H3  H3  H 0 1 N N N 16.279 -2.616 7.018  -4.822 1.185  -2.334 H3  8GN 37 
8GN H4  H4  H 0 1 N N N 17.484 -5.370 6.447  -6.511 -0.345 -2.082 H4  8GN 38 
8GN H5  H5  H 0 1 N N N 16.528 -4.308 5.359  -5.323 -1.670 -2.263 H5  8GN 39 
8GN H6  H6  H 0 1 N N N 14.537 -4.599 6.676  -6.437 -0.438 0.259  H6  8GN 40 
8GN H7  H7  H 0 1 N N N 14.581 -5.258 8.940  -4.299 -0.363 1.369  H7  8GN 41 
8GN H8  H8  H 0 1 N N N 16.141 -6.129 8.756  -3.529 -1.411 0.133  H8  8GN 42 
8GN H9  H9  H 0 1 N N N 13.394 -5.789 5.157  -6.060 -3.830 1.638  H9  8GN 43 
8GN H10 H10 H 0 1 N N N 14.892 -6.209 4.260  -4.915 -2.493 1.903  H10 8GN 44 
8GN H11 H11 H 0 1 N N N 13.761 -7.506 4.777  -6.668 -2.192 1.977  H11 8GN 45 
8GN H12 H12 H 0 1 N N N 16.529 -7.725 7.164  -7.989 -2.424 -0.082 H12 8GN 46 
8GN H13 H13 H 0 1 N N N 15.576 -8.626 5.937  -7.146 -2.651 -1.633 H13 8GN 47 
8GN H14 H14 H 0 1 N N N 16.707 -7.330 5.420  -7.247 -3.994 -0.469 H14 8GN 48 
8GN H15 H15 H 0 1 N N N 15.044 -2.316 13.623 4.187  1.734  -0.705 H15 8GN 49 
8GN H16 H16 H 0 1 N N N 15.264 0.258  19.577 4.071  -4.618 1.083  H16 8GN 50 
8GN H17 H17 H 0 1 N N N 12.671 -1.613 13.359 5.835  2.019  -0.807 H17 8GN 51 
8GN H18 H18 H 0 1 N N N 10.479 -2.852 13.615 8.464  0.421  -1.416 H18 8GN 52 
8GN H19 H19 H 0 1 N N N 10.811 -3.152 15.355 8.125  2.171  -1.887 H19 8GN 53 
8GN H20 H20 H 0 1 N N N 12.780 -0.918 15.717 6.641  -0.826 -0.164 H20 8GN 54 
8GN H21 H21 H 0 1 N N N 12.522 -4.115 13.008 7.834  2.774  0.560  H21 8GN 55 
8GN H22 H22 H 0 1 N N N 12.854 -4.415 14.747 8.174  1.024  1.031  H22 8GN 56 
8GN H23 H23 H 0 1 N N N 18.569 -2.121 13.988 1.875  2.462  -0.747 H23 8GN 57 
8GN H24 H24 H 0 1 N N N 18.499 -4.199 12.631 0.358  -0.665 -1.319 H24 8GN 58 
8GN H25 H25 H 0 1 N N N 17.723 -5.210 10.530 -2.063 -1.104 -1.297 H25 8GN 59 
8GN H26 H26 H 0 1 N N N 15.176 -1.983 8.505  -3.899 3.007  0.117  H26 8GN 60 
8GN H27 H27 H 0 1 N N N 14.102 1.325  8.055  -4.285 4.784  2.072  H27 8GN 61 
8GN H28 H28 H 0 1 N N N 15.143 0.145  7.188  -2.897 5.896  2.144  H28 8GN 62 
8GN H29 H29 H 0 1 N N N 13.514 -0.347 7.763  -3.789 5.682  0.618  H29 8GN 63 
# 
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 
8GN C12 N2  SING N N 1  
8GN C13 N2  SING N N 2  
8GN N2  C10 SING N N 3  
8GN C9  C10 SING N N 4  
8GN C9  C8  SING N N 5  
8GN C10 C11 SING N N 6  
8GN C8  N1  SING N N 7  
8GN C   C1  SING N N 8  
8GN C11 N1  SING N N 9  
8GN N1  C7  SING N N 10 
8GN C1  N   SING N N 11 
8GN C1  O   DOUB N N 12 
8GN N   C2  SING N N 13 
8GN C7  C2  DOUB Y N 14 
8GN C7  C6  SING Y N 15 
8GN C2  C3  SING Y N 16 
8GN C6  C5  DOUB Y N 17 
8GN C3  C4  DOUB Y N 18 
8GN C5  C4  SING Y N 19 
8GN C4  N3  SING N N 20 
8GN N3  C14 SING N N 21 
8GN C23 C21 SING N N 22 
8GN C23 C22 SING N N 23 
8GN C21 C22 SING N N 24 
8GN C21 N8  SING N N 25 
8GN C15 C14 SING Y N 26 
8GN C15 C16 DOUB Y N 27 
8GN C14 N5  DOUB Y N 28 
8GN N8  C16 SING N N 29 
8GN C16 N4  SING Y N 30 
8GN N5  C17 SING Y N 31 
8GN N4  C17 SING Y N 32 
8GN N4  N6  SING Y N 33 
8GN C17 C18 DOUB Y N 34 
8GN N6  C19 DOUB Y N 35 
8GN C18 C20 SING N N 36 
8GN C18 C19 SING Y N 37 
8GN C20 N7  TRIP N N 38 
8GN C3  H1  SING N N 39 
8GN C8  H2  SING N N 40 
8GN C8  H3  SING N N 41 
8GN C9  H4  SING N N 42 
8GN C9  H5  SING N N 43 
8GN C10 H6  SING N N 44 
8GN C11 H7  SING N N 45 
8GN C11 H8  SING N N 46 
8GN C12 H9  SING N N 47 
8GN C12 H10 SING N N 48 
8GN C12 H11 SING N N 49 
8GN C13 H12 SING N N 50 
8GN C13 H13 SING N N 51 
8GN C13 H14 SING N N 52 
8GN C15 H15 SING N N 53 
8GN C19 H16 SING N N 54 
8GN C21 H17 SING N N 55 
8GN C22 H18 SING N N 56 
8GN C22 H19 SING N N 57 
8GN N8  H20 SING N N 58 
8GN C23 H21 SING N N 59 
8GN C23 H22 SING N N 60 
8GN N3  H23 SING N N 61 
8GN C5  H24 SING N N 62 
8GN C6  H25 SING N N 63 
8GN N   H26 SING N N 64 
8GN C   H27 SING N N 65 
8GN C   H28 SING N N 66 
8GN C   H29 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 
8GN InChI            InChI                1.03  "InChI=1S/C24H29N9O/c1-15(34)27-20-10-18(6-7-21(20)32-9-8-19(14-32)31(2)3)28-22-11-23(29-17-4-5-17)33-24(30-22)16(12-25)13-26-33/h6-7,10-11,13,17,19,29H,4-5,8-9,14H2,1-3H3,(H,27,34)(H,28,30)/t19-/m1/s1" 
8GN InChIKey         InChI                1.03  PAKOVKWPBKKYGI-LJQANCHMSA-N                                                                                                                                                                                
8GN SMILES_CANONICAL CACTVS               3.385 "CN(C)[C@@H]1CCN(C1)c2ccc(Nc3cc(NC4CC4)n5ncc(C#N)c5n3)cc2NC(C)=O"                                                                                                                                          
8GN SMILES           CACTVS               3.385 "CN(C)[CH]1CCN(C1)c2ccc(Nc3cc(NC4CC4)n5ncc(C#N)c5n3)cc2NC(C)=O"                                                                                                                                            
8GN SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "CC(=O)Nc1cc(ccc1N2CC[C@H](C2)N(C)C)Nc3cc(n4c(n3)c(cn4)C#N)NC5CC5"                                                                                                                                         
8GN SMILES           "OpenEye OEToolkits" 2.0.6 "CC(=O)Nc1cc(ccc1N2CCC(C2)N(C)C)Nc3cc(n4c(n3)c(cn4)C#N)NC5CC5"                                                                                                                                             
# 
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 
8GN "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.6 "~{N}-[5-[[3-cyano-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-[(3~{R})-3-(dimethylamino)pyrrolidin-1-yl]phenyl]ethanamide" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
8GN "Create component" 2017-02-06 EBI  
8GN "Initial release"  2017-05-17 RCSB 
# 
