data_Q3A # _chem_comp.id Q3A _chem_comp.name "8-(2,6-dimethylpyridin-3-yl)-N-[(5-fluoro-2,3-dihydro-1-benzofuran-4-yl)methyl]-1-(methylsulfonyl)imidazo[1,5-c]pyrimidin-5-amine" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C23 H22 F N5 O3 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2019-09-11 _chem_comp.pdbx_modified_date 2020-07-03 _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 467.516 _chem_comp.one_letter_code ? _chem_comp.three_letter_code Q3A _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 6U93 _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 Q3A C16 C1 C 0 1 Y N N 13.301 26.173 20.008 5.196 -0.019 -1.758 C16 Q3A 1 Q3A C12 C2 C 0 1 N N N 10.339 25.522 23.530 6.058 0.442 2.816 C12 Q3A 2 Q3A C11 C3 C 0 1 N N N 11.417 24.632 22.979 4.947 1.069 1.942 C11 Q3A 3 Q3A C10 C4 C 0 1 Y N N 11.962 25.437 21.828 5.312 0.564 0.560 C10 Q3A 4 Q3A C15 C5 C 0 1 Y N N 12.678 27.399 19.985 6.493 -0.498 -1.697 C15 Q3A 5 Q3A C14 C6 C 0 1 Y N N 11.676 27.663 20.907 7.201 -0.444 -0.514 C14 Q3A 6 Q3A C13 C7 C 0 1 Y N N 11.342 26.677 21.820 6.616 0.093 0.630 C13 Q3A 7 Q3A C6 C8 C 0 1 Y N N 15.008 23.745 24.710 -0.822 1.728 -0.631 C6 Q3A 8 Q3A C9 C9 C 0 1 Y N N 12.971 25.157 20.883 4.606 0.513 -0.622 C9 Q3A 9 Q3A C1 C10 C 0 1 Y N N 17.476 22.982 29.070 -5.864 1.763 -0.272 C1 Q3A 10 Q3A C2 C11 C 0 1 Y N N 17.722 22.019 28.105 -5.387 1.034 -1.346 C2 Q3A 11 Q3A C7 C12 C 0 1 Y N N 15.464 23.806 22.416 0.907 0.198 -0.351 C7 Q3A 12 Q3A C3 C13 C 0 1 Y N N 17.355 22.262 26.796 -4.046 0.695 -1.393 C3 Q3A 13 Q3A C4 C14 C 0 1 Y N N 16.761 23.480 26.455 -3.220 1.108 -0.341 C4 Q3A 14 Q3A C5 C15 C 0 1 Y N N 16.338 23.711 25.047 -1.778 0.774 -0.341 C5 Q3A 15 Q3A O2 O1 O 0 1 N N N 21.071 24.659 24.311 -4.170 -0.739 0.795 O2 Q3A 16 Q3A S S1 S 0 1 N N N 19.981 24.106 25.053 -3.652 -2.018 0.457 S Q3A 17 Q3A O1 O2 O 0 1 N N N 19.496 24.833 26.186 -3.757 -3.112 1.358 O1 Q3A 18 Q3A C20 C16 C 0 1 N N N 20.433 22.496 25.570 -4.195 -2.507 -1.203 C20 Q3A 19 Q3A C18 C17 C 0 1 Y N N 18.668 23.916 23.878 -1.917 -1.755 0.293 C18 Q3A 20 Q3A C17 C18 C 0 1 Y N N 17.302 23.789 23.994 -1.313 -0.582 -0.032 C17 Q3A 21 Q3A C21 C19 C 0 1 Y N N 16.534 24.415 27.492 -3.779 1.841 0.707 C21 Q3A 22 Q3A C22 C20 C 0 1 N N N 15.934 25.771 27.270 -2.907 2.295 1.849 C22 Q3A 23 Q3A N4 N1 N 0 1 Y N N 16.875 24.143 28.764 -5.061 2.143 0.703 N4 Q3A 24 Q3A C C21 C 0 1 N N N 17.909 22.798 30.499 -7.324 2.133 -0.217 C Q3A 25 Q3A N3 N2 N 0 1 Y N N 19.025 23.990 22.549 -0.961 -2.675 0.465 N3 Q3A 26 Q3A C19 C22 C 0 1 Y N N 17.920 23.926 21.857 0.214 -2.135 0.271 C19 Q3A 27 Q3A N2 N3 N 0 1 Y N N 16.827 23.820 22.669 0.050 -0.825 -0.050 N2 Q3A 28 Q3A N N4 N 0 1 Y N N 14.584 23.781 23.412 0.473 1.403 -0.631 N Q3A 29 Q3A N1 N5 N 0 1 N N N 15.010 23.807 21.143 2.259 -0.044 -0.360 N1 Q3A 30 Q3A C8 C23 C 0 1 N N N 13.590 23.775 20.821 3.194 1.037 -0.680 C8 Q3A 31 Q3A F F1 F 0 1 N N N 14.337 25.960 19.170 4.509 -0.066 -2.920 F Q3A 32 Q3A O O3 O 0 1 N N N 10.382 26.778 22.804 7.133 0.257 1.879 O Q3A 33 Q3A H12 H1 H 0 1 N N N 10.515 25.703 24.601 6.354 1.124 3.613 H12 Q3A 34 Q3A H11 H2 H 0 1 N N N 9.356 25.046 23.395 5.736 -0.515 3.228 H11 Q3A 35 Q3A H10 H3 H 0 1 N N N 11.001 23.675 22.631 3.964 0.706 2.242 H10 Q3A 36 Q3A H9 H4 H 0 1 N N N 12.196 24.441 23.732 4.987 2.158 1.983 H9 Q3A 37 Q3A H14 H5 H 0 1 N N N 12.965 28.146 19.259 6.953 -0.916 -2.580 H14 Q3A 38 Q3A H13 H6 H 0 1 N N N 11.168 28.616 20.913 8.213 -0.820 -0.475 H13 Q3A 39 Q3A H5 H7 H 0 1 N N N 14.271 23.743 25.499 -1.123 2.739 -0.864 H5 Q3A 40 Q3A H3 H8 H 0 1 N N N 18.196 21.087 28.374 -6.054 0.732 -2.140 H3 Q3A 41 Q3A H4 H9 H 0 1 N N N 17.527 21.512 26.038 -3.647 0.126 -2.219 H4 Q3A 42 Q3A H18 H10 H 0 1 N N N 21.249 22.562 26.304 -3.970 -1.707 -1.909 H18 Q3A 43 Q3A H17 H11 H 0 1 N N N 19.565 22.002 26.031 -3.672 -3.415 -1.504 H17 Q3A 44 Q3A H16 H12 H 0 1 N N N 20.768 21.912 24.700 -5.269 -2.692 -1.194 H16 Q3A 45 Q3A H21 H13 H 0 1 N N N 15.883 26.311 28.227 -2.494 3.278 1.622 H21 Q3A 46 Q3A H20 H14 H 0 1 N N N 16.558 26.337 26.563 -3.503 2.353 2.760 H20 Q3A 47 Q3A H19 H15 H 0 1 N N N 14.920 25.660 26.857 -2.094 1.583 1.991 H19 Q3A 48 Q3A H1 H16 H 0 1 N N N 17.645 23.694 31.081 -7.878 1.349 0.299 H1 Q3A 49 Q3A H2 H17 H 0 1 N N N 17.401 21.921 30.926 -7.440 3.074 0.321 H2 Q3A 50 Q3A H H18 H 0 1 N N N 18.998 22.645 30.535 -7.709 2.244 -1.231 H Q3A 51 Q3A H15 H19 H 0 1 N N N 17.876 23.953 20.778 1.161 -2.648 0.345 H15 Q3A 52 Q3A H6 H20 H 0 1 N N N 15.413 23.004 20.703 2.595 -0.931 -0.155 H6 Q3A 53 Q3A H7 H21 H 0 1 N N N 13.076 23.121 21.541 3.077 1.845 0.042 H7 Q3A 54 Q3A H8 H22 H 0 1 N N N 13.464 23.373 19.805 2.987 1.412 -1.683 H8 Q3A 55 # # 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 Q3A F C16 SING N N 1 Q3A C15 C16 DOUB Y N 2 Q3A C15 C14 SING Y N 3 Q3A C16 C9 SING Y N 4 Q3A C8 C9 SING N N 5 Q3A C8 N1 SING N N 6 Q3A C9 C10 DOUB Y N 7 Q3A C14 C13 DOUB Y N 8 Q3A N1 C7 SING N N 9 Q3A C13 C10 SING Y N 10 Q3A C13 O SING N N 11 Q3A C10 C11 SING N N 12 Q3A C19 N3 DOUB Y N 13 Q3A C19 N2 SING Y N 14 Q3A C7 N2 SING Y N 15 Q3A C7 N DOUB Y N 16 Q3A N3 C18 SING Y N 17 Q3A N2 C17 SING Y N 18 Q3A O C12 SING N N 19 Q3A C11 C12 SING N N 20 Q3A N C6 SING Y N 21 Q3A C18 C17 DOUB Y N 22 Q3A C18 S SING N N 23 Q3A C17 C5 SING Y N 24 Q3A O2 S DOUB N N 25 Q3A C6 C5 DOUB Y N 26 Q3A C5 C4 SING N N 27 Q3A S C20 SING N N 28 Q3A S O1 DOUB N N 29 Q3A C4 C3 DOUB Y N 30 Q3A C4 C21 SING Y N 31 Q3A C3 C2 SING Y N 32 Q3A C22 C21 SING N N 33 Q3A C21 N4 DOUB Y N 34 Q3A C2 C1 DOUB Y N 35 Q3A N4 C1 SING Y N 36 Q3A C1 C SING N N 37 Q3A C12 H12 SING N N 38 Q3A C12 H11 SING N N 39 Q3A C11 H10 SING N N 40 Q3A C11 H9 SING N N 41 Q3A C15 H14 SING N N 42 Q3A C14 H13 SING N N 43 Q3A C6 H5 SING N N 44 Q3A C2 H3 SING N N 45 Q3A C3 H4 SING N N 46 Q3A C20 H18 SING N N 47 Q3A C20 H17 SING N N 48 Q3A C20 H16 SING N N 49 Q3A C22 H21 SING N N 50 Q3A C22 H20 SING N N 51 Q3A C22 H19 SING N N 52 Q3A C H1 SING N N 53 Q3A C H2 SING N N 54 Q3A C H SING N N 55 Q3A C19 H15 SING N N 56 Q3A N1 H6 SING N N 57 Q3A C8 H7 SING N N 58 Q3A C8 H8 SING N N 59 # # 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 Q3A SMILES ACDLabs 12.01 "c2(c(c1CCOc1cc2)CNc3n5c(c(cn3)c4ccc(C)nc4C)c(S(=O)(C)=O)nc5)F" Q3A InChI InChI 1.03 "InChI=1S/C23H22FN5O3S/c1-13-4-5-15(14(2)28-13)18-11-26-23(29-12-27-22(21(18)29)33(3,30)31)25-10-17-16-8-9-32-20(16)7-6-19(17)24/h4-7,11-12H,8-10H2,1-3H3,(H,25,26)" Q3A InChIKey InChI 1.03 BXNZBHMPQIUISX-UHFFFAOYSA-N Q3A SMILES_CANONICAL CACTVS 3.385 "Cc1ccc(c(C)n1)c2cnc(NCc3c(F)ccc4OCCc34)n5cnc(c25)[S](C)(=O)=O" Q3A SMILES CACTVS 3.385 "Cc1ccc(c(C)n1)c2cnc(NCc3c(F)ccc4OCCc34)n5cnc(c25)[S](C)(=O)=O" Q3A SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "Cc1ccc(c(n1)C)c2cnc(n3c2c(nc3)S(=O)(=O)C)NCc4c(ccc5c4CCO5)F" Q3A SMILES "OpenEye OEToolkits" 2.0.7 "Cc1ccc(c(n1)C)c2cnc(n3c2c(nc3)S(=O)(=O)C)NCc4c(ccc5c4CCO5)F" # # 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 Q3A "SYSTEMATIC NAME" ACDLabs 12.01 "8-(2,6-dimethylpyridin-3-yl)-N-[(5-fluoro-2,3-dihydro-1-benzofuran-4-yl)methyl]-1-(methylsulfonyl)imidazo[1,5-c]pyrimidin-5-amine" Q3A "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.7 "8-(2,6-dimethylpyridin-3-yl)-~{N}-[(5-fluoranyl-2,3-dihydro-1-benzofuran-4-yl)methyl]-1-methylsulfonyl-imidazo[1,5-c]pyrimidin-5-amine" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site Q3A "Create component" 2019-09-11 RCSB Q3A "Initial release" 2020-07-08 RCSB ##