data_1J9
# 
_chem_comp.id                                    1J9 
_chem_comp.name                                  "(2S)-2-{[1-(2-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]oxy}-N-(5-chloropyridin-2-yl)-3-(2-hydroxyethoxy)propanamide" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H18 Cl2 N6 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2013-02-14 
_chem_comp.pdbx_modified_date                    2013-04-19 
_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                        489.311 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     1J9 
_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        4IWV 
_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 
1J9 C1  C1  C  0 1 Y N N 52.523 29.646 -21.184 7.674  0.125  -1.572 C1  1J9 1  
1J9 C2  C2  C  0 1 Y N N 51.361 29.949 -20.509 8.508  0.623  -0.588 C2  1J9 2  
1J9 C3  C3  C  0 1 Y N N 51.013 29.287 -19.346 7.982  1.046  0.619  C3  1J9 3  
1J9 C4  C4  C  0 1 Y N N 51.848 28.304 -18.866 6.621  0.970  0.846  C4  1J9 4  
1J9 C5  C5  C  0 1 Y N N 53.003 28.009 -19.553 5.781  0.470  -0.141 C5  1J9 5  
1J9 C6  C6  C  0 1 Y N N 53.358 28.658 -20.713 6.313  0.047  -1.352 C6  1J9 6  
1J9 N1  N1  N  0 1 Y N N 53.858 27.019 -19.056 4.400  0.391  0.085  N1  1J9 7  
1J9 C7  C7  C  0 1 Y N N 53.778 25.684 -19.353 3.470  -0.083 -0.796 C7  1J9 8  
1J9 C8  C8  C  0 1 Y N N 54.495 25.045 -18.368 2.220  0.023  -0.154 C8  1J9 9  
1J9 C9  C9  C  0 1 Y N N 54.974 26.075 -17.519 2.457  0.574  1.125  C9  1J9 10 
1J9 N2  N2  N  0 1 Y N N 54.577 27.275 -17.951 3.737  0.780  1.256  N2  1J9 11 
1J9 C10 C10 C  0 1 Y N N 54.588 23.679 -18.423 1.076  -0.403 -0.851 C10 1J9 12 
1J9 N3  N3  N  0 1 Y N N 53.981 23.036 -19.414 1.226  -0.884 -2.078 N3  1J9 13 
1J9 C11 C11 C  0 1 Y N N 53.325 23.790 -20.308 2.420  -0.965 -2.640 C11 1J9 14 
1J9 N4  N4  N  0 1 Y N N 53.158 25.109 -20.383 3.519  -0.580 -2.030 N4  1J9 15 
1J9 O1  O1  O  0 1 N N N 55.295 22.997 -17.453 -0.151 -0.324 -0.283 O1  1J9 16 
1J9 C12 C12 C  0 1 N N S 55.214 21.615 -17.743 -1.258 -0.779 -1.064 C12 1J9 17 
1J9 C13 C13 C  0 1 N N N 56.505 21.011 -17.205 -1.488 -2.269 -0.803 C13 1J9 18 
1J9 O2  O2  O  0 1 N N N 57.569 21.599 -17.937 -1.882 -2.458 0.558  O2  1J9 19 
1J9 C14 C14 C  0 1 N N N 58.786 21.298 -17.283 -2.123 -3.822 0.909  C14 1J9 20 
1J9 C15 C15 C  0 1 N N N 59.920 21.685 -18.198 -2.536 -3.905 2.380  C15 1J9 21 
1J9 O3  O3  O  0 1 N N N 60.120 20.706 -19.203 -3.788 -3.241 2.561  O3  1J9 22 
1J9 C16 C16 C  0 1 N N N 54.038 21.151 -16.938 -2.493 -0.005 -0.683 C16 1J9 23 
1J9 O4  O4  O  0 1 N N N 53.401 21.890 -16.192 -2.432 0.851  0.173  O4  1J9 24 
1J9 N5  N5  N  0 1 N N N 53.798 19.822 -17.093 -3.667 -0.266 -1.293 N5  1J9 25 
1J9 C17 C17 C  0 1 Y N N 52.650 19.219 -16.520 -4.831 0.374  -0.869 C17 1J9 26 
1J9 C18 C18 C  0 1 Y N N 51.674 19.936 -15.843 -6.053 0.023  -1.431 C18 1J9 27 
1J9 C19 C19 C  0 1 Y N N 50.552 19.274 -15.332 -7.201 0.666  -1.000 C19 1J9 28 
1J9 C20 C20 C  0 1 Y N N 50.468 17.911 -15.520 -7.085 1.641  -0.018 C20 1J9 29 
1J9 C21 C21 C  0 1 Y N N 51.497 17.300 -16.185 -5.838 1.938  0.496  C21 1J9 30 
1J9 N6  N6  N  0 1 Y N N 52.571 17.905 -16.691 -4.762 1.305  0.069  N6  1J9 31 
1J9 CL1 CL1 CL 0 0 N N N 49.174 16.880 -14.990 -8.493 2.477  0.557  CL1 1J9 32 
1J9 CL2 CL2 CL 0 0 N N N 51.468 27.454 -17.414 5.962  1.499  2.362  CL2 1J9 33 
1J9 H1  H1  H  0 1 N N N 52.779 30.185 -22.084 8.087  -0.200 -2.516 H1  1J9 34 
1J9 H2  H2  H  0 1 N N N 50.709 30.718 -20.896 9.572  0.683  -0.762 H2  1J9 35 
1J9 H3  H3  H  0 1 N N N 50.102 29.537 -18.823 8.636  1.434  1.386  H3  1J9 36 
1J9 H4  H4  H  0 1 N N N 54.265 28.400 -21.239 5.662  -0.342 -2.122 H4  1J9 37 
1J9 H5  H5  H  0 1 N N N 55.579 25.911 -16.640 1.705  0.785  1.870  H5  1J9 38 
1J9 H6  H6  H  0 1 N N N 52.851 23.233 -21.103 2.495  -1.364 -3.641 H6  1J9 39 
1J9 H7  H7  H  0 1 N N N 55.086 21.403 -18.815 -1.044 -0.625 -2.122 H7  1J9 40 
1J9 H8  H8  H  0 1 N N N 56.502 19.921 -17.351 -2.273 -2.637 -1.463 H8  1J9 41 
1J9 H9  H9  H  0 1 N N N 56.612 21.238 -16.134 -0.566 -2.818 -0.994 H9  1J9 42 
1J9 H10 H10 H  0 1 N N N 58.835 20.221 -17.064 -2.922 -4.222 0.284  H10 1J9 43 
1J9 H11 H11 H  0 1 N N N 58.855 21.866 -16.344 -1.214 -4.404 0.753  H11 1J9 44 
1J9 H12 H12 H  0 1 N N N 60.841 21.786 -17.606 -2.634 -4.951 2.671  H12 1J9 45 
1J9 H13 H13 H  0 1 N N N 59.684 22.647 -18.676 -1.777 -3.426 2.998  H13 1J9 46 
1J9 H14 H14 H  0 1 N N N 60.838 20.971 -19.766 -4.112 -3.254 3.472  H14 1J9 47 
1J9 H15 H15 H  0 1 N N N 54.439 19.263 -17.618 -3.701 -0.898 -2.028 H15 1J9 48 
1J9 H16 H16 H  0 1 N N N 51.780 21.003 -15.711 -6.106 -0.739 -2.193 H16 1J9 49 
1J9 H17 H17 H  0 1 N N N 49.777 19.813 -14.807 -8.164 0.415  -1.419 H17 1J9 50 
1J9 H18 H18 H  0 1 N N N 51.432 16.229 -16.311 -5.742 2.696  1.260  H18 1J9 51 
# 
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 
1J9 C1  C6  DOUB Y N 1  
1J9 C1  C2  SING Y N 2  
1J9 C6  C5  SING Y N 3  
1J9 C2  C3  DOUB Y N 4  
1J9 N4  C11 DOUB Y N 5  
1J9 N4  C7  SING Y N 6  
1J9 C11 N3  SING Y N 7  
1J9 C5  N1  SING N N 8  
1J9 C5  C4  DOUB Y N 9  
1J9 N3  C10 DOUB Y N 10 
1J9 C7  N1  SING Y N 11 
1J9 C7  C8  DOUB Y N 12 
1J9 C3  C4  SING Y N 13 
1J9 O3  C15 SING N N 14 
1J9 N1  N2  SING Y N 15 
1J9 C4  CL2 SING N N 16 
1J9 C10 C8  SING Y N 17 
1J9 C10 O1  SING N N 18 
1J9 C8  C9  SING Y N 19 
1J9 C15 C14 SING N N 20 
1J9 N2  C9  DOUB Y N 21 
1J9 O2  C14 SING N N 22 
1J9 O2  C13 SING N N 23 
1J9 C12 O1  SING N N 24 
1J9 C12 C13 SING N N 25 
1J9 C12 C16 SING N N 26 
1J9 N5  C16 SING N N 27 
1J9 N5  C17 SING N N 28 
1J9 C16 O4  DOUB N N 29 
1J9 N6  C17 DOUB Y N 30 
1J9 N6  C21 SING Y N 31 
1J9 C17 C18 SING Y N 32 
1J9 C21 C20 DOUB Y N 33 
1J9 C18 C19 DOUB Y N 34 
1J9 C20 C19 SING Y N 35 
1J9 C20 CL1 SING N N 36 
1J9 C1  H1  SING N N 37 
1J9 C2  H2  SING N N 38 
1J9 C3  H3  SING N N 39 
1J9 C6  H4  SING N N 40 
1J9 C9  H5  SING N N 41 
1J9 C11 H6  SING N N 42 
1J9 C12 H7  SING N N 43 
1J9 C13 H8  SING N N 44 
1J9 C13 H9  SING N N 45 
1J9 C14 H10 SING N N 46 
1J9 C14 H11 SING N N 47 
1J9 C15 H12 SING N N 48 
1J9 C15 H13 SING N N 49 
1J9 O3  H14 SING N N 50 
1J9 N5  H15 SING N N 51 
1J9 C18 H16 SING N N 52 
1J9 C19 H17 SING N N 53 
1J9 C21 H18 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 
1J9 SMILES           ACDLabs              12.01 "Clc1ccc(nc1)NC(=O)C(Oc2ncnc3c2cnn3c4ccccc4Cl)COCCO"                                                                                                                                 
1J9 InChI            InChI                1.03  "InChI=1S/C21H18Cl2N6O4/c22-13-5-6-18(24-9-13)28-20(31)17(11-32-8-7-30)33-21-14-10-27-29(19(14)25-12-26-21)16-4-2-1-3-15(16)23/h1-6,9-10,12,17,30H,7-8,11H2,(H,24,28,31)/t17-/m0/s1" 
1J9 InChIKey         InChI                1.03  KTWRHJPPIZQGRW-KRWDZBQOSA-N                                                                                                                                                          
1J9 SMILES_CANONICAL CACTVS               3.370 "OCCOC[C@H](Oc1ncnc2n(ncc12)c3ccccc3Cl)C(=O)Nc4ccc(Cl)cn4"                                                                                                                           
1J9 SMILES           CACTVS               3.370 "OCCOC[CH](Oc1ncnc2n(ncc12)c3ccccc3Cl)C(=O)Nc4ccc(Cl)cn4"                                                                                                                            
1J9 SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "c1ccc(c(c1)n2c3c(cn2)c(ncn3)O[C@@H](COCCO)C(=O)Nc4ccc(cn4)Cl)Cl"                                                                                                                    
1J9 SMILES           "OpenEye OEToolkits" 1.7.6 "c1ccc(c(c1)n2c3c(cn2)c(ncn3)OC(COCCO)C(=O)Nc4ccc(cn4)Cl)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 
1J9 "SYSTEMATIC NAME" ACDLabs              12.01 "(2S)-2-{[1-(2-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]oxy}-N-(5-chloropyridin-2-yl)-3-(2-hydroxyethoxy)propanamide" 
1J9 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "(2S)-N-(5-chloranylpyridin-2-yl)-2-[1-(2-chlorophenyl)pyrazolo[3,4-d]pyrimidin-4-yl]oxy-3-(2-hydroxyethyloxy)propanamide"  
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
1J9 "Create component" 2013-02-14 RCSB 
1J9 "Initial release"  2013-04-24 RCSB 
# 
