data_D4A # _chem_comp.id D4A _chem_comp.name "(6R)-3-[(2-chlorophenyl)sulfanyl]-6-{6-[(4-fluorophenyl)amino]pyridin-2-yl}-4-hydroxy-6-(thiophen-3-yl)-5,6-dihydro-2H-pyran-2-one" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C26 H18 Cl F N2 O3 S2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2017-10-17 _chem_comp.pdbx_modified_date 2018-10-19 _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 525.014 _chem_comp.one_letter_code ? _chem_comp.three_letter_code D4A _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 6BB3 _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 D4A C4 C1 C 0 1 Y N N -15.588 -13.532 17.099 -5.340 -0.921 0.032 C4 D4A 1 D4A C14 C2 C 0 1 Y N N -13.733 -11.965 22.651 -0.493 4.266 -1.210 C14 D4A 2 D4A C5 C3 C 0 1 Y N N -13.210 -13.709 16.831 -4.508 -3.053 -0.704 C5 D4A 3 D4A C6 C4 C 0 1 Y N N -15.645 -12.575 16.108 -6.549 -1.507 0.354 C6 D4A 4 D4A C11 C5 C 0 1 Y N N -13.355 -16.163 20.312 -3.081 0.068 1.270 C11 D4A 5 D4A C7 C6 C 0 1 Y N N -13.250 -12.745 15.844 -5.720 -3.634 -0.386 C7 D4A 6 D4A C8 C7 C 0 1 Y N N -10.189 -15.635 18.573 4.598 -0.290 0.186 C8 D4A 7 D4A C9 C8 C 0 1 Y N N -8.578 -17.674 17.660 6.314 -2.458 0.364 C9 D4A 8 D4A C10 C9 C 0 1 Y N N -11.961 -14.948 21.784 -1.398 1.711 1.645 C10 D4A 9 D4A C12 C10 C 0 1 Y N N -11.926 -10.581 23.015 0.263 4.490 0.942 C12 D4A 10 D4A C13 C11 C 0 1 Y N N -12.838 -9.977 23.849 -0.061 5.770 0.752 C13 D4A 11 D4A C3 C12 C 0 1 Y N N -12.539 -16.146 21.420 -2.508 1.012 2.102 C3 D4A 12 D4A C1 C13 C 0 1 Y N N -10.742 -16.842 18.189 5.940 -0.091 0.445 C1 D4A 13 D4A C2 C14 C 0 1 Y N N -9.940 -17.869 17.736 6.797 -1.173 0.533 C2 D4A 14 D4A C15 C15 C 0 1 Y N N -12.414 -11.724 22.322 0.021 3.660 -0.139 C15 D4A 15 D4A C16 C16 C 0 1 Y N N -14.380 -14.097 17.468 -4.316 -1.693 -0.501 C16 D4A 16 D4A C17 C17 C 0 1 Y N N -14.469 -12.191 15.496 -6.740 -2.862 0.146 C17 D4A 17 D4A C18 C18 C 0 1 Y N N -8.822 -15.440 18.514 4.108 -1.580 0.020 C18 D4A 18 D4A C19 C19 C 0 1 Y N N -8.018 -16.467 18.045 4.972 -2.666 0.110 C19 D4A 19 D4A C20 C20 C 0 1 Y N N -12.222 -13.808 21.045 -0.896 1.436 0.389 C20 D4A 20 D4A C21 C21 C 0 1 Y N N -13.566 -14.994 19.610 -2.526 -0.154 0.014 C21 D4A 21 D4A C22 C22 C 0 1 N N N -9.309 -13.114 19.887 1.744 -0.202 -0.329 C22 D4A 22 D4A C23 C23 C 0 1 N N N -10.224 -12.287 19.367 1.228 0.304 -1.464 C23 D4A 23 D4A C24 C24 C 0 1 N N N -9.327 -13.370 21.350 1.756 0.618 0.889 C24 D4A 24 D4A C25 C25 C 0 1 N N N -11.312 -11.657 20.154 0.672 1.701 -1.515 C25 D4A 25 D4A C26 C26 C 0 1 N N R -11.572 -12.493 21.392 0.316 2.182 -0.108 C26 D4A 26 D4A N27 N1 N 0 1 Y N N -13.019 -13.825 19.969 -1.464 0.529 -0.384 N27 D4A 27 D4A N28 N2 N 0 1 N N N -14.382 -15.075 18.475 -3.093 -1.101 -0.832 N28 D4A 28 D4A O29 O1 O 0 1 N N N -8.527 -14.099 21.910 2.051 0.140 1.969 O29 D4A 29 D4A O30 O2 O 0 1 N N N -10.316 -12.717 22.040 1.426 1.930 0.766 O30 D4A 30 D4A O31 O3 O 0 1 N N N -10.274 -12.021 18.023 1.208 -0.458 -2.580 O31 D4A 31 D4A F32 F1 F 0 1 N N N -14.522 -11.261 14.539 -7.925 -3.432 0.457 F32 D4A 32 D4A S33 S1 S 0 1 Y N N -14.325 -10.819 23.783 -0.697 5.981 -0.875 S33 D4A 33 D4A S34 S2 S 0 1 N N N -8.080 -13.903 18.978 2.395 -1.839 -0.302 S34 D4A 34 D4A CL35 CL1 CL 0 0 N N N -6.297 -16.271 17.903 4.367 -4.279 -0.102 CL35 D4A 35 D4A H1 H1 H 0 1 N N N -16.496 -13.844 17.593 -5.193 0.137 0.191 H1 D4A 36 D4A H2 H2 H 0 1 N N N -14.320 -12.776 22.246 -0.741 3.780 -2.142 H2 D4A 37 D4A H3 H3 H 0 1 N N N -12.269 -14.161 17.107 -3.713 -3.655 -1.119 H3 D4A 38 D4A H4 H4 H 0 1 N N N -16.588 -12.136 15.817 -7.346 -0.907 0.768 H4 D4A 39 D4A H5 H5 H 0 1 N N N -13.825 -17.082 19.995 -3.945 -0.494 1.594 H5 D4A 40 D4A H6 H6 H 0 1 N N N -12.343 -12.428 15.351 -5.871 -4.691 -0.544 H6 D4A 41 D4A H7 H7 H 0 1 N N N -10.830 -14.838 18.922 3.929 0.555 0.118 H7 D4A 42 D4A H8 H8 H 0 1 N N N -7.942 -18.468 17.297 6.987 -3.300 0.434 H8 D4A 43 D4A H9 H9 H 0 1 N N N -11.307 -14.900 22.642 -0.927 2.455 2.270 H9 D4A 44 D4A H10 H10 H 0 1 N N N -10.917 -10.216 22.895 0.675 4.128 1.872 H10 D4A 45 D4A H11 H11 H 0 1 N N N -12.644 -9.103 24.454 0.050 6.556 1.484 H11 D4A 46 D4A H12 H12 H 0 1 N N N -12.356 -17.046 21.989 -2.914 1.202 3.084 H12 D4A 47 D4A H13 H13 H 0 1 N N N -11.811 -16.982 18.244 6.320 0.911 0.578 H13 D4A 48 D4A H14 H14 H 0 1 N N N -10.374 -18.814 17.445 7.846 -1.014 0.736 H14 D4A 49 D4A H15 H15 H 0 1 N N N -11.012 -10.641 20.451 1.416 2.370 -1.948 H15 D4A 50 D4A H16 H16 H 0 1 N N N -12.226 -11.606 19.545 -0.223 1.711 -2.138 H16 D4A 51 D4A H17 H17 H 0 1 N N N -14.991 -15.862 18.378 -2.640 -1.351 -1.653 H17 D4A 52 D4A H18 H18 H 0 1 N N N -10.985 -11.416 17.846 1.511 -1.366 -2.442 H18 D4A 53 # 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 D4A F32 C17 SING N N 1 D4A C17 C7 DOUB Y N 2 D4A C17 C6 SING Y N 3 D4A C7 C5 SING Y N 4 D4A C6 C4 DOUB Y N 5 D4A C5 C16 DOUB Y N 6 D4A C4 C16 SING Y N 7 D4A C16 N28 SING N N 8 D4A C9 C2 DOUB Y N 9 D4A C9 C19 SING Y N 10 D4A C2 C1 SING Y N 11 D4A CL35 C19 SING N N 12 D4A O31 C23 SING N N 13 D4A C19 C18 DOUB Y N 14 D4A C1 C8 DOUB Y N 15 D4A N28 C21 SING N N 16 D4A C18 C8 SING Y N 17 D4A C18 S34 SING N N 18 D4A S34 C22 SING N N 19 D4A C23 C22 DOUB N N 20 D4A C23 C25 SING N N 21 D4A C21 N27 DOUB Y N 22 D4A C21 C11 SING Y N 23 D4A C22 C24 SING N N 24 D4A N27 C20 SING Y N 25 D4A C25 C26 SING N N 26 D4A C11 C3 DOUB Y N 27 D4A C20 C26 SING N N 28 D4A C20 C10 DOUB Y N 29 D4A C24 O29 DOUB N N 30 D4A C24 O30 SING N N 31 D4A C26 O30 SING N N 32 D4A C26 C15 SING N N 33 D4A C3 C10 SING Y N 34 D4A C15 C14 DOUB Y N 35 D4A C15 C12 SING Y N 36 D4A C14 S33 SING Y N 37 D4A C12 C13 DOUB Y N 38 D4A S33 C13 SING Y N 39 D4A C4 H1 SING N N 40 D4A C14 H2 SING N N 41 D4A C5 H3 SING N N 42 D4A C6 H4 SING N N 43 D4A C11 H5 SING N N 44 D4A C7 H6 SING N N 45 D4A C8 H7 SING N N 46 D4A C9 H8 SING N N 47 D4A C10 H9 SING N N 48 D4A C12 H10 SING N N 49 D4A C13 H11 SING N N 50 D4A C3 H12 SING N N 51 D4A C1 H13 SING N N 52 D4A C2 H14 SING N N 53 D4A C25 H15 SING N N 54 D4A C25 H16 SING N N 55 D4A N28 H17 SING N N 56 D4A O31 H18 SING N N 57 # 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 D4A SMILES ACDLabs 12.01 "c1c(ccc(c1)F)Nc5cccc(C3(c2cscc2)CC(=C(C(=O)O3)Sc4ccccc4Cl)O)n5" D4A InChI InChI 1.03 "InChI=1S/C26H18ClFN2O3S2/c27-19-4-1-2-5-21(19)35-24-20(31)14-26(33-25(24)32,16-12-13-34-15-16)22-6-3-7-23(30-22)29-18-10-8-17(28)9-11-18/h1-13,15,31H,14H2,(H,29,30)/t26-/m1/s1" D4A InChIKey InChI 1.03 FGGVZLMILAHJIQ-AREMUKBSSA-N D4A SMILES_CANONICAL CACTVS 3.385 "OC1=C(Sc2ccccc2Cl)C(=O)O[C@](C1)(c3cscc3)c4cccc(Nc5ccc(F)cc5)n4" D4A SMILES CACTVS 3.385 "OC1=C(Sc2ccccc2Cl)C(=O)O[C](C1)(c3cscc3)c4cccc(Nc5ccc(F)cc5)n4" D4A SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "c1ccc(c(c1)SC2=C(C[C@@](OC2=O)(c3ccsc3)c4cccc(n4)Nc5ccc(cc5)F)O)Cl" D4A SMILES "OpenEye OEToolkits" 2.0.6 "c1ccc(c(c1)SC2=C(CC(OC2=O)(c3ccsc3)c4cccc(n4)Nc5ccc(cc5)F)O)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 D4A "SYSTEMATIC NAME" ACDLabs 12.01 "(6R)-3-[(2-chlorophenyl)sulfanyl]-6-{6-[(4-fluorophenyl)amino]pyridin-2-yl}-4-hydroxy-6-(thiophen-3-yl)-5,6-dihydro-2H-pyran-2-one" D4A "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.6 "(2~{R})-5-(2-chlorophenyl)sulfanyl-2-[6-[(4-fluorophenyl)amino]pyridin-2-yl]-4-oxidanyl-2-thiophen-3-yl-3~{H}-pyran-6-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 D4A "Create component" 2017-10-17 RCSB D4A "Initial release" 2018-10-24 RCSB #