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 #