data_2KW # _chem_comp.id 2KW _chem_comp.name "3-chloro-5-({1-[(4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]-2-oxo-4-(trifluoromethyl)-1,2-dihydropyridin-3-yl}oxy)benzonitrile" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C17 H11 Cl F3 N5 O3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms Doravirine _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2013-11-21 _chem_comp.pdbx_modified_date 2022-10-03 _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 425.749 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 2KW _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 4NCG _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 2KW C8 C8 C 0 1 N N N 10.906 12.181 15.264 -0.853 -2.534 -0.178 C8 2KW 1 2KW C7 C7 C 0 1 N N N 10.218 11.764 16.335 -0.813 -1.460 0.666 C7 2KW 2 2KW C9 C9 C 0 1 N N N 10.241 12.556 14.055 0.343 -3.179 -0.524 C9 2KW 3 2KW C10 C10 C 0 1 N N N 8.911 12.457 13.984 1.520 -2.734 -0.026 C10 2KW 4 2KW C6 C6 C 0 1 N N N 9.725 10.922 22.072 -4.540 3.259 1.017 C6 2KW 5 2KW C5 C5 C 0 1 Y N N 10.105 13.103 21.123 -2.488 3.061 -0.309 C5 2KW 6 2KW C4 C4 C 0 1 Y N N 10.043 11.735 20.962 -3.412 2.496 0.572 C4 2KW 7 2KW C3 C3 C 0 1 Y N N 10.297 11.160 19.738 -3.234 1.186 1.018 C3 2KW 8 2KW C2 C2 C 0 1 Y N N 10.617 11.972 18.670 -2.140 0.454 0.584 C2 2KW 9 2KW C1 C1 C 0 1 Y N N 10.701 13.340 18.805 -1.226 1.023 -0.292 C1 2KW 10 2KW C13 C13 C 0 1 N N N 12.401 12.254 15.326 -2.169 -3.023 -0.727 C13 2KW 11 2KW C12 C12 C 0 1 N N N 8.714 11.669 16.265 0.431 -1.023 1.166 C12 2KW 12 2KW C24 C24 C 0 1 N N N 5.939 9.318 16.439 5.559 0.278 1.692 C24 2KW 13 2KW C18 C18 C 0 1 N N N 6.517 10.563 14.275 3.437 -0.179 0.397 C18 2KW 14 2KW C17 C17 C 0 1 N N N 6.715 11.945 14.863 2.850 -1.203 1.334 C17 2KW 15 2KW C21 C21 C 0 1 N N N 6.143 8.398 14.145 4.822 1.303 -0.472 C21 2KW 16 2KW C C C 0 1 Y N N 10.422 13.889 20.033 -1.405 2.321 -0.739 C 2KW 17 2KW F F F 0 1 N N N 12.904 11.034 15.548 -2.446 -2.365 -1.931 F 2KW 18 2KW N N N 0 1 N N N 9.507 10.255 22.994 -5.434 3.864 1.370 N 2KW 19 2KW O O O 0 1 N N N 10.923 11.388 17.463 -1.960 -0.820 1.020 O 2KW 20 2KW CL CL CL 0 0 N N N 10.501 15.586 20.173 -0.256 3.024 -1.835 CL 2KW 21 2KW N11 N11 N 0 1 N N N 8.157 12.018 15.042 1.561 -1.663 0.810 N11 2KW 22 2KW F14 F14 F 0 1 N N N 12.819 12.988 16.392 -2.095 -4.402 -0.956 F14 2KW 23 2KW F15 F15 F 0 1 N N N 13.082 12.630 14.209 -3.187 -2.757 0.195 F15 2KW 24 2KW O16 O16 O 0 1 N N N 8.045 11.314 17.235 0.484 -0.065 1.921 O16 2KW 25 2KW N19 N19 N 0 1 N N N 6.651 10.292 13.015 2.891 0.239 -0.699 N19 2KW 26 2KW N20 N20 N 0 1 N N N 6.410 8.958 12.920 3.747 1.185 -1.280 N20 2KW 27 2KW N22 N22 N 0 1 N N N 6.200 9.447 15.015 4.637 0.467 0.570 N22 2KW 28 2KW O23 O23 O 0 1 N N N 5.910 7.220 14.387 5.780 2.034 -0.648 O23 2KW 29 2KW H1 H1 H 0 1 N N N 10.808 12.915 13.209 0.325 -4.031 -1.187 H1 2KW 30 2KW H2 H2 H 0 1 N N N 8.414 12.731 13.065 2.437 -3.236 -0.296 H2 2KW 31 2KW H3 H3 H 0 1 N N N 9.909 13.552 22.085 -2.622 4.074 -0.657 H3 2KW 32 2KW H4 H4 H 0 1 N N N 10.247 10.088 19.615 -3.945 0.744 1.700 H4 2KW 33 2KW H5 H5 H 0 1 N N N 10.979 13.964 17.968 -0.375 0.450 -0.628 H5 2KW 34 2KW H6 H6 H 0 1 N N N 6.047 10.300 16.923 6.265 -0.517 1.452 H6 2KW 35 2KW H7 H7 H 0 1 N N N 4.915 8.945 16.592 6.103 1.204 1.875 H7 2KW 36 2KW H8 H8 H 0 1 N N N 6.657 8.611 16.881 4.995 0.005 2.584 H8 2KW 37 2KW H9 H9 H 0 1 N N N 6.362 12.724 14.171 3.530 -2.050 1.420 H9 2KW 38 2KW H10 H10 H 0 1 N N N 6.191 12.045 15.825 2.703 -0.754 2.317 H10 2KW 39 2KW H11 H11 H 0 1 N N N 6.425 8.446 12.061 3.595 1.666 -2.108 H11 2KW 40 # 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 2KW N20 N19 SING N N 1 2KW N20 C21 SING N N 2 2KW N19 C18 DOUB N N 3 2KW C10 C9 DOUB N N 4 2KW C10 N11 SING N N 5 2KW C9 C8 SING N N 6 2KW C21 O23 DOUB N N 7 2KW C21 N22 SING N N 8 2KW F15 C13 SING N N 9 2KW C18 C17 SING N N 10 2KW C18 N22 SING N N 11 2KW C17 N11 SING N N 12 2KW N22 C24 SING N N 13 2KW N11 C12 SING N N 14 2KW C8 C13 SING N N 15 2KW C8 C7 DOUB N N 16 2KW C13 F SING N N 17 2KW C13 F14 SING N N 18 2KW C12 C7 SING N N 19 2KW C12 O16 DOUB N N 20 2KW C7 O SING N N 21 2KW O C2 SING N N 22 2KW C2 C1 DOUB Y N 23 2KW C2 C3 SING Y N 24 2KW C1 C SING Y N 25 2KW C3 C4 DOUB Y N 26 2KW C CL SING N N 27 2KW C C5 DOUB Y N 28 2KW C4 C5 SING Y N 29 2KW C4 C6 SING N N 30 2KW C6 N TRIP N N 31 2KW C9 H1 SING N N 32 2KW C10 H2 SING N N 33 2KW C5 H3 SING N N 34 2KW C3 H4 SING N N 35 2KW C1 H5 SING N N 36 2KW C24 H6 SING N N 37 2KW C24 H7 SING N N 38 2KW C24 H8 SING N N 39 2KW C17 H9 SING N N 40 2KW C17 H10 SING N N 41 2KW N20 H11 SING N N 42 # 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 2KW SMILES ACDLabs 12.01 "FC(F)(F)C2=C(Oc1cc(C#N)cc(Cl)c1)C(=O)N(C=C2)CC3=NNC(=O)N3C" 2KW InChI InChI 1.03 "InChI=1S/C17H11ClF3N5O3/c1-25-13(23-24-16(25)28)8-26-3-2-12(17(19,20)21)14(15(26)27)29-11-5-9(7-22)4-10(18)6-11/h2-6H,8H2,1H3,(H,24,28)" 2KW InChIKey InChI 1.03 ZIAOVIPSKUPPQW-UHFFFAOYSA-N 2KW SMILES_CANONICAL CACTVS 3.385 "CN1C(=O)NN=C1CN2C=CC(=C(Oc3cc(Cl)cc(c3)C#N)C2=O)C(F)(F)F" 2KW SMILES CACTVS 3.385 "CN1C(=O)NN=C1CN2C=CC(=C(Oc3cc(Cl)cc(c3)C#N)C2=O)C(F)(F)F" 2KW SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "CN1C(=NNC1=O)CN2C=CC(=C(C2=O)Oc3cc(cc(c3)Cl)C#N)C(F)(F)F" 2KW SMILES "OpenEye OEToolkits" 1.7.6 "CN1C(=NNC1=O)CN2C=CC(=C(C2=O)Oc3cc(cc(c3)Cl)C#N)C(F)(F)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 2KW "SYSTEMATIC NAME" ACDLabs 12.01 "3-chloro-5-({1-[(4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]-2-oxo-4-(trifluoromethyl)-1,2-dihydropyridin-3-yl}oxy)benzonitrile" 2KW "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "3-chloranyl-5-[1-[(4-methyl-5-oxidanylidene-1H-1,2,4-triazol-3-yl)methyl]-2-oxidanylidene-4-(trifluoromethyl)pyridin-3-yl]oxy-benzenecarbonitrile" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 2KW "Create component" 2013-11-21 RCSB 2KW "Initial release" 2014-02-12 RCSB 2KW "Modify synonyms" 2022-10-03 RCSB # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 2KW _pdbx_chem_comp_synonyms.name Doravirine _pdbx_chem_comp_synonyms.provenance DRUGBANK _pdbx_chem_comp_synonyms.type ? #