data_R9P
# 
_chem_comp.id                                    R9P 
_chem_comp.name                                  "8-bromo-2-{2-chloro-4-[(piperidin-4-ylmethyl)amino]phenyl}[1]benzofuro[3,2-d]pyrimidin-4(3H)-one" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H20 Br Cl N4 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2012-03-05 
_chem_comp.pdbx_modified_date                    2014-04-28 
_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                        487.777 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     R9P 
_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        4ALV 
_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 
R9P C13  C13  C  0 1 N N N -22.656 32.919 7.815  -8.667  -0.326 0.508  C13  R9P 1  
R9P C14  C14  C  0 1 N N N -23.523 34.125 8.201  -9.940  0.524  0.531  C14  R9P 2  
R9P N3   N3   N  0 1 N N N -24.638 33.764 9.122  -10.023 1.316  -0.703 N3   R9P 3  
R9P C15  C15  C  0 1 N N N -24.190 32.949 10.294 -8.888  2.240  -0.818 C15  R9P 4  
R9P C16  C16  C  0 1 N N N -23.377 31.710 9.851  -7.583  1.442  -0.881 C16  R9P 5  
R9P C12  C12  C  0 1 N N N -23.369 31.670 8.325  -7.448  0.594  0.386  C12  R9P 6  
R9P C11  C11  C  0 1 N N N -22.838 30.336 7.787  -6.176  -0.252 0.302  C11  R9P 7  
R9P N2   N2   N  0 1 N N N -21.825 30.456 6.738  -5.004  0.627  0.305  N2   R9P 8  
R9P C10  C10  C  0 1 Y N N -21.918 30.807 5.443  -3.725  0.081  0.235  C10  R9P 9  
R9P C17  C17  C  0 1 Y N N -21.108 31.857 5.052  -2.613  0.918  0.239  C17  R9P 10 
R9P C18  C18  C  0 1 Y N N -21.042 32.325 3.758  -1.345  0.381  0.170  C18  R9P 11 
R9P CL1  CL1  CL 0 0 N N N -19.986 33.617 3.444  0.042   1.425  0.175  CL1  R9P 12 
R9P C9   C9   C  0 1 Y N N -22.650 30.174 4.449  -3.561  -1.299 0.168  C9   R9P 13 
R9P C8   C8   C  0 1 Y N N -22.571 30.656 3.133  -2.298  -1.842 0.099  C8   R9P 14 
R9P C7   C7   C  0 1 Y N N -21.749 31.732 2.762  -1.179  -1.006 0.097  C7   R9P 15 
R9P C6   C6   C  0 1 N N N -21.741 32.150 1.436  0.177   -1.585 0.023  C6   R9P 16 
R9P N4   N4   N  0 1 N N N -22.043 33.407 1.107  1.219   -0.783 0.027  N4   R9P 17 
R9P C19  C19  C  0 1 Y N N -22.084 33.735 -0.185 2.465   -1.269 -0.038 C19  R9P 18 
R9P C20  C20  C  0 1 Y N N -22.371 34.890 -0.835 3.804   -0.659 -0.053 C20  R9P 19 
R9P C21  C21  C  0 1 Y N N -22.698 36.097 -0.364 4.272   0.652  -0.004 C21  R9P 20 
R9P C22  C22  C  0 1 Y N N -22.938 37.152 -1.248 5.629   0.895  -0.037 C22  R9P 21 
R9P BR1  BR1  BR 0 0 N N N -23.385 38.856 -0.440 6.270   2.672  0.029  BR1  R9P 22 
R9P C1   C1   C  0 1 Y N N -22.855 36.989 -2.627 6.525   -0.162 -0.118 C1   R9P 23 
R9P C2   C2   C  0 1 Y N N -22.520 35.736 -3.080 6.074   -1.463 -0.167 C2   R9P 24 
R9P C3   C3   C  0 1 Y N N -22.284 34.712 -2.190 4.709   -1.729 -0.134 C3   R9P 25 
R9P O1   O1   O  0 1 Y N N -21.955 33.436 -2.398 4.004   -2.880 -0.167 O1   R9P 26 
R9P C4   C4   C  0 1 Y N N -21.840 32.834 -1.202 2.676   -2.644 -0.112 C4   R9P 27 
R9P C5   C5   C  0 1 N N N -21.528 31.554 -0.920 1.549   -3.495 -0.116 C5   R9P 28 
R9P O2   O2   O  0 1 N N N -21.312 30.807 -1.870 1.684   -4.706 -0.179 O2   R9P 29 
R9P N1   N1   N  0 1 N N N -21.474 31.201 0.429  0.320   -2.942 -0.043 N1   R9P 30 
R9P H131 H131 H  0 0 N N N -22.544 32.869 6.722  -8.597  -0.902 1.431  H131 R9P 31 
R9P H132 H132 H  0 0 N N N -21.663 33.003 8.282  -8.697  -1.004 -0.344 H132 R9P 32 
R9P H141 H141 H  0 0 N N N -22.885 34.872 8.697  -10.810 -0.129 0.603  H141 R9P 33 
R9P H142 H142 H  0 0 N N N -23.950 34.558 7.285  -9.915  1.192  1.391  H142 R9P 34 
R9P H12  H12  H  0 1 N N N -24.417 31.747 8.000  -7.395  1.246  1.258  H12  R9P 35 
R9P H3   H3   H  0 1 N N N -25.056 34.607 9.461  -10.087 0.718  -1.513 H3   R9P 36 
R9P H151 H151 H  0 0 N N N -23.561 33.575 10.944 -8.994  2.835  -1.725 H151 R9P 37 
R9P H152 H152 H  0 0 N N N -25.075 32.613 10.854 -8.868  2.901  0.049  H152 R9P 38 
R9P H161 H161 H  0 0 N N N -22.346 31.786 10.228 -7.597  0.791  -1.755 H161 R9P 39 
R9P H162 H162 H  0 0 N N N -23.845 30.796 10.246 -6.740  2.129  -0.951 H162 R9P 40 
R9P H111 H111 H  0 0 N N N -22.396 29.780 8.627  -6.129  -0.924 1.158  H111 R9P 41 
R9P H112 H112 H  0 0 N N N -23.688 29.769 7.379  -6.189  -0.837 -0.618 H112 R9P 42 
R9P H2   H2   H  0 1 N N N -21.171 31.112 7.115  -5.119  1.588  0.356  H2   R9P 43 
R9P H17  H17  H  0 1 N N N -20.494 32.336 5.801  -2.743  1.988  0.295  H17  R9P 44 
R9P H9   H9   H  0 1 N N N -23.272 29.323 4.684  -4.427  -1.945 0.169  H9   R9P 45 
R9P H8   H8   H  0 1 N N N -23.169 30.178 2.372  -2.173  -2.914 0.047  H8   R9P 46 
R9P H1   H1   H  0 1 N N N -21.243 30.262 0.684  -0.465  -3.511 -0.040 H1   R9P 47 
R9P H21  H21  H  0 1 N N N -22.777 36.257 0.701  3.576   1.475  0.058  H21  R9P 48 
R9P HA   HA   H  0 1 N N N -23.044 37.806 -3.307 7.586   0.038  -0.144 HA   R9P 49 
R9P HB   HB   H  0 1 N N N -22.441 35.553 -4.141 6.781   -2.277 -0.230 HB   R9P 50 
# 
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 
R9P C13 C14  SING N N 1  
R9P C13 C12  SING N N 2  
R9P C14 N3   SING N N 3  
R9P N3  C15  SING N N 4  
R9P C15 C16  SING N N 5  
R9P C16 C12  SING N N 6  
R9P C12 C11  SING N N 7  
R9P C11 N2   SING N N 8  
R9P N2  C10  SING N N 9  
R9P C10 C17  SING Y N 10 
R9P C10 C9   DOUB Y N 11 
R9P C17 C18  DOUB Y N 12 
R9P C18 CL1  SING N N 13 
R9P C18 C7   SING Y N 14 
R9P C9  C8   SING Y N 15 
R9P C8  C7   DOUB Y N 16 
R9P C7  C6   SING N N 17 
R9P C6  N4   DOUB N N 18 
R9P C6  N1   SING N N 19 
R9P N4  C19  SING N N 20 
R9P C19 C20  SING Y N 21 
R9P C19 C4   DOUB Y N 22 
R9P C20 C21  SING Y N 23 
R9P C20 C3   DOUB Y N 24 
R9P C21 C22  DOUB Y N 25 
R9P C22 BR1  SING N N 26 
R9P C22 C1   SING Y N 27 
R9P C1  C2   DOUB Y N 28 
R9P C2  C3   SING Y N 29 
R9P C3  O1   SING Y N 30 
R9P O1  C4   SING Y N 31 
R9P C4  C5   SING N N 32 
R9P C5  O2   DOUB N N 33 
R9P C5  N1   SING N N 34 
R9P C13 H131 SING N N 35 
R9P C13 H132 SING N N 36 
R9P C14 H141 SING N N 37 
R9P C14 H142 SING N N 38 
R9P C12 H12  SING N N 39 
R9P N3  H3   SING N N 40 
R9P C15 H151 SING N N 41 
R9P C15 H152 SING N N 42 
R9P C16 H161 SING N N 43 
R9P C16 H162 SING N N 44 
R9P C11 H111 SING N N 45 
R9P C11 H112 SING N N 46 
R9P N2  H2   SING N N 47 
R9P C17 H17  SING N N 48 
R9P C9  H9   SING N N 49 
R9P C8  H8   SING N N 50 
R9P N1  H1   SING N N 51 
R9P C21 H21  SING N N 52 
R9P C1  HA   SING N N 53 
R9P C2  HB   SING N N 54 
# 
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 
R9P SMILES           ACDLabs              12.01 "Clc5cc(NCC1CCNCC1)ccc5C3=Nc2c4c(oc2C(=O)N3)ccc(Br)c4"                                                                                                               
R9P InChI            InChI                1.03  "InChI=1S/C22H20BrClN4O2/c23-13-1-4-18-16(9-13)19-20(30-18)22(29)28-21(27-19)15-3-2-14(10-17(15)24)26-11-12-5-7-25-8-6-12/h1-4,9-10,12,25-26H,5-8,11H2,(H,27,28,29)" 
R9P InChIKey         InChI                1.03  RUIXFIILMZVAAF-UHFFFAOYSA-N                                                                                                                                          
R9P SMILES_CANONICAL CACTVS               3.370 "Clc1cc(NCC2CCNCC2)ccc1C3=Nc4c(oc5ccc(Br)cc45)C(=O)N3"                                                                                                               
R9P SMILES           CACTVS               3.370 "Clc1cc(NCC2CCNCC2)ccc1C3=Nc4c(oc5ccc(Br)cc45)C(=O)N3"                                                                                                               
R9P SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "c1cc(c(cc1NCC2CCNCC2)Cl)C3=Nc4c5cc(ccc5oc4C(=O)N3)Br"                                                                                                               
R9P SMILES           "OpenEye OEToolkits" 1.7.6 "c1cc(c(cc1NCC2CCNCC2)Cl)C3=Nc4c5cc(ccc5oc4C(=O)N3)Br"                                                                                                               
# 
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 
R9P "SYSTEMATIC NAME" ACDLabs              12.01 "8-bromo-2-{2-chloro-4-[(piperidin-4-ylmethyl)amino]phenyl}[1]benzofuro[3,2-d]pyrimidin-4(3H)-one"     
R9P "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "8-bromanyl-2-[2-chloranyl-4-(piperidin-4-ylmethylamino)phenyl]-3H-[1]benzofuro[3,2-d]pyrimidin-4-one" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
R9P "Create component"   2012-03-05 EBI  
R9P "Initial release"    2013-01-11 RCSB 
R9P "Other modification" 2014-04-28 EBI  
# 
