data_D3S # _chem_comp.id D3S _chem_comp.name "(6S)-3-[(2-chlorophenyl)sulfanyl]-4-hydroxy-6-(2-hydroxyphenyl)-6-phenyl-5,6-dihydro-2H-pyran-2-one" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C23 H17 Cl O4 S" _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 424.897 _chem_comp.one_letter_code ? _chem_comp.three_letter_code D3S _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 6BB0 _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 D3S C4 C1 C 0 1 Y N N -9.176 -18.161 17.701 5.064 -2.634 -0.407 C4 D3S 1 D3S C14 C2 C 0 1 Y N N -12.421 -12.067 22.259 -3.123 -1.125 -0.009 C14 D3S 2 D3S C5 C3 C 0 1 Y N N -10.071 -17.187 18.151 3.699 -2.787 -0.247 C5 D3S 3 D3S C6 C4 C 0 1 Y N N -9.631 -15.925 18.552 2.905 -1.687 0.012 C6 D3S 4 D3S C7 C5 C 0 1 Y N N -8.260 -15.596 18.525 3.478 -0.425 0.111 C7 D3S 5 D3S C9 C6 C 0 1 N N N -9.040 -13.270 19.973 0.837 0.319 0.379 C9 D3S 6 D3S C10 C7 C 0 1 N N N -9.959 -12.474 19.362 0.080 0.276 1.492 C10 D3S 7 D3S C12 C8 C 0 1 N N N -11.106 -11.840 20.096 -1.309 -0.301 1.470 C12 D3S 8 D3S C13 C9 C 0 1 N N S -11.502 -12.776 21.261 -1.860 -0.304 0.043 C13 D3S 9 D3S C3 C10 C 0 1 Y N N -7.819 -17.858 17.658 5.641 -1.381 -0.304 C3 D3S 10 D3S CL1 CL1 CL 0 0 N N N -5.661 -16.270 17.976 5.575 1.298 0.079 CL1 D3S 11 D3S C2 C11 C 0 1 Y N N -7.365 -16.594 18.067 4.852 -0.275 -0.050 C2 D3S 12 D3S S8 S1 S 0 1 N N N -7.698 -13.979 19.078 2.469 0.981 0.441 S8 D3S 13 D3S O11 O1 O 0 1 N N N -9.860 -12.212 18.054 0.578 0.759 2.651 O11 D3S 14 D3S C15 C12 C 0 1 Y N N -13.749 -12.483 22.476 -3.194 -2.232 -0.831 C15 D3S 15 D3S C16 C13 C 0 1 Y N N -14.557 -11.820 23.409 -4.350 -2.989 -0.875 C16 D3S 16 D3S C17 C14 C 0 1 Y N N -14.034 -10.749 24.155 -5.438 -2.640 -0.096 C17 D3S 17 D3S C18 C15 C 0 1 Y N N -12.709 -10.318 23.960 -5.372 -1.533 0.728 C18 D3S 18 D3S C19 C16 C 0 1 Y N N -11.895 -10.982 23.017 -4.213 -0.772 0.774 C19 D3S 19 D3S O20 O2 O 0 1 N N N -10.600 -10.556 22.827 -4.145 0.317 1.584 O20 D3S 20 D3S C21 C17 C 0 1 Y N N -12.096 -14.065 20.670 -2.157 1.110 -0.386 C21 D3S 21 D3S C22 C18 C 0 1 Y N N -12.933 -14.039 19.538 -2.520 2.056 0.555 C22 D3S 22 D3S C23 C19 C 0 1 Y N N -13.463 -15.210 18.985 -2.788 3.354 0.162 C23 D3S 23 D3S C24 C20 C 0 1 Y N N -13.162 -16.447 19.558 -2.691 3.706 -1.171 C24 D3S 24 D3S C25 C21 C 0 1 Y N N -12.322 -16.494 20.681 -2.327 2.761 -2.111 C25 D3S 25 D3S C26 C22 C 0 1 Y N N -11.795 -15.316 21.237 -2.061 1.463 -1.719 C26 D3S 26 D3S O27 O3 O 0 1 N N N -10.263 -12.993 22.023 -0.879 -0.876 -0.834 O27 D3S 27 D3S C28 C23 C 0 1 N N N -9.179 -13.542 21.404 0.294 -0.193 -0.886 C28 D3S 28 D3S O29 O4 O 0 1 N N N -8.390 -14.231 22.020 0.873 -0.013 -1.940 O29 D3S 29 D3S H1 H1 H 0 1 N N N -9.532 -19.133 17.392 5.683 -3.496 -0.610 H1 D3S 30 D3S H2 H2 H 0 1 N N N -11.126 -17.416 18.189 3.254 -3.767 -0.325 H2 D3S 31 D3S H3 H3 H 0 1 N N N -10.349 -15.191 18.887 1.839 -1.808 0.136 H3 D3S 32 D3S H4 H4 H 0 1 N N N -10.800 -10.860 20.492 -1.281 -1.323 1.848 H4 D3S 33 D3S H5 H5 H 0 1 N N N -11.960 -11.710 19.414 -1.959 0.299 2.107 H5 D3S 34 D3S H6 H6 H 0 1 N N N -7.113 -18.597 17.309 6.707 -1.265 -0.429 H6 D3S 35 D3S H7 H7 H 0 1 N N N -10.575 -11.646 17.789 1.444 1.181 2.561 H7 D3S 36 D3S H8 H8 H 0 1 N N N -14.147 -13.319 21.920 -2.346 -2.507 -1.441 H8 D3S 37 D3S H9 H9 H 0 1 N N N -15.581 -12.131 23.555 -4.404 -3.855 -1.519 H9 D3S 38 D3S H10 H10 H 0 1 N N N -14.656 -10.252 24.885 -6.340 -3.233 -0.132 H10 D3S 39 D3S H11 H11 H 0 1 N N N -12.318 -9.486 24.527 -6.222 -1.261 1.337 H11 D3S 40 D3S H12 H12 H 0 1 N N N -10.416 -9.829 23.410 -4.433 1.139 1.163 H12 D3S 41 D3S H13 H13 H 0 1 N N N -13.173 -13.089 19.084 -2.596 1.780 1.596 H13 D3S 42 D3S H14 H14 H 0 1 N N N -14.103 -15.157 18.117 -3.072 4.092 0.897 H14 D3S 43 D3S H15 H15 H 0 1 N N N -13.570 -17.356 19.142 -2.901 4.720 -1.478 H15 D3S 44 D3S H16 H16 H 0 1 N N N -12.077 -17.448 21.124 -2.252 3.036 -3.153 H16 D3S 45 D3S H17 H17 H 0 1 N N N -11.155 -15.372 22.105 -1.773 0.725 -2.453 H17 D3S 46 # 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 D3S C3 C4 DOUB Y N 1 D3S C3 C2 SING Y N 2 D3S C4 C5 SING Y N 3 D3S CL1 C2 SING N N 4 D3S O11 C10 SING N N 5 D3S C2 C7 DOUB Y N 6 D3S C5 C6 DOUB Y N 7 D3S C7 C6 SING Y N 8 D3S C7 S8 SING N N 9 D3S C23 C22 DOUB Y N 10 D3S C23 C24 SING Y N 11 D3S S8 C9 SING N N 12 D3S C10 C9 DOUB N N 13 D3S C10 C12 SING N N 14 D3S C22 C21 SING Y N 15 D3S C24 C25 DOUB Y N 16 D3S C9 C28 SING N N 17 D3S C12 C13 SING N N 18 D3S C21 C26 DOUB Y N 19 D3S C21 C13 SING N N 20 D3S C25 C26 SING Y N 21 D3S C13 O27 SING N N 22 D3S C13 C14 SING N N 23 D3S C28 O29 DOUB N N 24 D3S C28 O27 SING N N 25 D3S C14 C15 DOUB Y N 26 D3S C14 C19 SING Y N 27 D3S C15 C16 SING Y N 28 D3S O20 C19 SING N N 29 D3S C19 C18 DOUB Y N 30 D3S C16 C17 DOUB Y N 31 D3S C18 C17 SING Y N 32 D3S C4 H1 SING N N 33 D3S C5 H2 SING N N 34 D3S C6 H3 SING N N 35 D3S C12 H4 SING N N 36 D3S C12 H5 SING N N 37 D3S C3 H6 SING N N 38 D3S O11 H7 SING N N 39 D3S C15 H8 SING N N 40 D3S C16 H9 SING N N 41 D3S C17 H10 SING N N 42 D3S C18 H11 SING N N 43 D3S O20 H12 SING N N 44 D3S C22 H13 SING N N 45 D3S C23 H14 SING N N 46 D3S C24 H15 SING N N 47 D3S C25 H16 SING N N 48 D3S C26 H17 SING N N 49 # 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 D3S SMILES ACDLabs 12.01 "c4ccc(SC=2C(OC(c1ccccc1O)(CC=2O)c3ccccc3)=O)c(c4)Cl" D3S InChI InChI 1.03 "InChI=1S/C23H17ClO4S/c24-17-11-5-7-13-20(17)29-21-19(26)14-23(28-22(21)27,15-8-2-1-3-9-15)16-10-4-6-12-18(16)25/h1-13,25-26H,14H2/t23-/m0/s1" D3S InChIKey InChI 1.03 ARSBHTFMIZULEW-QHCPKHFHSA-N D3S SMILES_CANONICAL CACTVS 3.385 "OC1=C(Sc2ccccc2Cl)C(=O)O[C@@](C1)(c3ccccc3)c4ccccc4O" D3S SMILES CACTVS 3.385 "OC1=C(Sc2ccccc2Cl)C(=O)O[C](C1)(c3ccccc3)c4ccccc4O" D3S SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "c1ccc(cc1)[C@@]2(CC(=C(C(=O)O2)Sc3ccccc3Cl)O)c4ccccc4O" D3S SMILES "OpenEye OEToolkits" 2.0.6 "c1ccc(cc1)C2(CC(=C(C(=O)O2)Sc3ccccc3Cl)O)c4ccccc4O" # 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 D3S "SYSTEMATIC NAME" ACDLabs 12.01 "(6S)-3-[(2-chlorophenyl)sulfanyl]-4-hydroxy-6-(2-hydroxyphenyl)-6-phenyl-5,6-dihydro-2H-pyran-2-one" D3S "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.6 "(2~{S})-5-(2-chlorophenyl)sulfanyl-2-(2-hydroxyphenyl)-4-oxidanyl-2-phenyl-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 D3S "Create component" 2017-10-17 RCSB D3S "Initial release" 2018-10-24 RCSB #