data_3W5 # _chem_comp.id 3W5 _chem_comp.name "N-[(3S)-1,1-dioxidotetrahydro-2H-thiopyran-3-yl]-4-(4-{[(3S)-3-hydroxy-1-azabicyclo[2.2.2]oct-3-yl]ethynyl}phenoxy)benzamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C27 H30 N2 O5 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2011-11-11 _chem_comp.pdbx_modified_date 2014-09-05 _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 494.603 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 3W5 _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 4A7B _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site EBI # 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 3W5 C1 C1 C 0 1 Y N N 23.911 14.205 12.781 3.016 1.047 -1.111 C1 3W5 1 3W5 C2 C2 C 0 1 Y N N 24.288 13.659 13.985 1.930 1.895 -1.085 C2 3W5 2 3W5 C3 C3 C 0 1 Y N N 23.366 12.900 14.689 1.609 2.579 0.080 C3 3W5 3 3W5 C4 C4 C 0 1 Y N N 22.084 12.688 14.245 2.379 2.411 1.223 C4 3W5 4 3W5 C5 C5 C 0 1 Y N N 21.700 13.236 13.035 3.467 1.565 1.205 C5 3W5 5 3W5 C6 C6 C 0 1 Y N N 22.633 13.979 12.335 3.793 0.875 0.036 C6 3W5 6 3W5 C7 C7 C 0 1 N N N 22.185 14.481 11.112 4.922 -0.005 0.013 C7 3W5 7 3W5 C8 C8 C 0 1 N N N 21.840 14.878 10.037 5.847 -0.728 -0.005 C8 3W5 8 3W5 C9 C9 C 0 1 N N S 21.392 15.299 8.737 7.008 -1.633 -0.028 C9 3W5 9 3W5 C10 C10 C 0 1 N N N 19.885 15.089 8.754 7.681 -1.639 1.347 C10 3W5 10 3W5 N1 N1 N 0 1 N N N 19.519 14.248 7.569 9.070 -1.178 1.212 N1 3W5 11 3W5 C11 C11 C 0 1 N N N 19.879 14.955 6.287 9.844 -2.079 0.347 C11 3W5 12 3W5 C12 C12 C 0 1 N N N 21.400 15.078 6.276 9.231 -2.086 -1.057 C12 3W5 13 3W5 C13 C13 C 0 1 N N N 22.022 14.512 7.566 8.019 -1.146 -1.073 C13 3W5 14 3W5 C14 C14 C 0 1 N N N 21.632 13.012 7.658 8.487 0.262 -0.682 C14 3W5 15 3W5 C15 C15 C 0 1 N N N 20.088 12.856 7.696 9.121 0.203 0.711 C15 3W5 16 3W5 O1 O1 O 0 1 N N N 21.795 16.664 8.678 6.577 -2.956 -0.356 O1 3W5 17 3W5 O2 O2 O 0 1 N N N 23.646 12.308 15.878 0.538 3.415 0.101 O2 3W5 18 3W5 C16 C16 C 0 1 Y N N 24.255 12.987 16.900 -0.699 2.869 -0.017 C16 3W5 19 3W5 C21 C21 C 0 1 Y N N 24.789 12.178 17.880 -1.812 3.693 -0.134 C21 3W5 20 3W5 C20 C20 C 0 1 Y N N 25.422 12.739 18.979 -3.069 3.143 -0.253 C20 3W5 21 3W5 C19 C19 C 0 1 Y N N 25.485 14.100 19.083 -3.224 1.754 -0.257 C19 3W5 22 3W5 C18 C18 C 0 1 Y N N 24.958 14.915 18.111 -2.102 0.929 -0.140 C18 3W5 23 3W5 C17 C17 C 0 1 Y N N 24.335 14.360 17.004 -0.848 1.487 -0.026 C17 3W5 24 3W5 C22 C22 C 0 1 N N N 26.200 14.653 20.240 -4.569 1.161 -0.384 C22 3W5 25 3W5 O3 O3 O 0 1 N N N 26.229 14.041 21.300 -5.544 1.880 -0.486 O3 3W5 26 3W5 N2 N2 N 0 1 N N N 26.885 15.821 19.893 -4.717 -0.179 -0.388 N2 3W5 27 3W5 C23 C23 C 0 1 N N S 27.357 16.895 20.752 -6.052 -0.769 -0.514 C23 3W5 28 3W5 C24 C24 C 0 1 N N N 26.442 17.262 21.893 -5.933 -2.172 -1.102 C24 3W5 29 3W5 C25 C25 C 0 1 N N N 26.978 18.406 22.755 -7.308 -2.716 -1.479 C25 3W5 30 3W5 C26 C26 C 0 1 N N N 28.014 17.853 23.707 -8.117 -3.014 -0.215 C26 3W5 31 3W5 S1 S1 S 0 1 N N N 29.326 17.590 22.572 -8.406 -1.461 0.682 S1 3W5 32 3W5 O5 O5 O 0 1 N N N 29.398 18.940 22.028 -9.131 -0.577 -0.161 O5 3W5 33 3W5 O4 O4 O 0 1 N N N 30.450 16.814 23.092 -8.919 -1.769 1.971 O4 3W5 34 3W5 C27 C27 C 0 1 N N N 28.734 16.541 21.238 -6.711 -0.834 0.866 C27 3W5 35 3W5 H1 H1 H 0 1 N N N 24.603 14.797 12.201 3.263 0.512 -2.016 H1 3W5 36 3W5 H2 H2 H 0 1 N N N 25.283 13.818 14.375 1.329 2.029 -1.973 H2 3W5 37 3W5 H4 H4 H 0 1 N N N 21.389 12.104 14.830 2.126 2.945 2.127 H4 3W5 38 3W5 H5 H5 H 0 1 N N N 20.702 13.088 12.649 4.067 1.436 2.094 H5 3W5 39 3W5 H101 H101 H 0 0 N N N 19.591 14.575 9.681 7.141 -0.974 2.020 H101 3W5 40 3W5 H102 H102 H 0 0 N N N 19.372 16.060 8.694 7.673 -2.651 1.752 H102 3W5 41 3W5 H13 H13 H 0 1 N N N 23.116 14.630 7.559 7.563 -1.140 -2.063 H13 3W5 42 3W5 HA HA H 0 1 N N N 21.538 17.035 7.842 5.938 -3.327 0.268 HA 3W5 43 3W5 H111 H111 H 0 0 N N N 19.538 14.369 5.421 10.876 -1.733 0.292 H111 3W5 44 3W5 H112 H112 H 0 0 N N N 19.416 15.953 6.260 9.820 -3.088 0.759 H112 3W5 45 3W5 H151 H151 H 0 0 N N N 19.774 12.402 8.647 8.570 0.856 1.389 H151 3W5 46 3W5 H152 H152 H 0 0 N N N 19.748 12.228 6.860 10.159 0.530 0.653 H152 3W5 47 3W5 H121 H121 H 0 0 N N N 21.797 14.522 5.414 9.971 -1.742 -1.780 H121 3W5 48 3W5 H122 H122 H 0 0 N N N 21.672 16.140 6.184 8.912 -3.097 -1.311 H122 3W5 49 3W5 H141 H141 H 0 0 N N N 22.029 12.480 6.781 9.224 0.616 -1.403 H141 3W5 50 3W5 H142 H142 H 0 0 N N N 22.063 12.581 8.574 7.634 0.939 -0.666 H142 3W5 51 3W5 H17 H17 H 0 1 N N N 23.919 14.993 16.235 0.020 0.850 0.061 H17 3W5 52 3W5 H21 H21 H 0 1 N N N 24.714 11.104 17.792 -1.691 4.766 -0.131 H21 3W5 53 3W5 H18 H18 H 0 1 N N N 25.029 15.988 18.209 -2.218 -0.145 -0.142 H18 3W5 54 3W5 H20 H20 H 0 1 N N N 25.858 12.110 19.741 -3.933 3.784 -0.343 H20 3W5 55 3W5 HB HB H 0 1 N N N 27.077 15.934 18.918 -3.939 -0.753 -0.307 HB 3W5 56 3W5 H23 H23 H 0 1 N N N 27.461 17.794 20.127 -6.660 -0.150 -1.174 H23 3W5 57 3W5 H241 H241 H 0 0 N N N 25.470 17.564 21.477 -5.304 -2.136 -1.992 H241 3W5 58 3W5 H242 H242 H 0 0 N N N 26.308 16.377 22.532 -5.475 -2.832 -0.366 H242 3W5 59 3W5 H271 H271 H 0 0 N N N 28.719 15.501 21.596 -6.142 -1.504 1.510 H271 3W5 60 3W5 H272 H272 H 0 0 N N N 29.433 16.628 20.393 -6.736 0.163 1.306 H272 3W5 61 3W5 H251 H251 H 0 0 N N N 27.438 19.170 22.111 -7.836 -1.977 -2.081 H251 3W5 62 3W5 H252 H252 H 0 0 N N N 26.153 18.856 23.327 -7.188 -3.632 -2.057 H252 3W5 63 3W5 H261 H261 H 0 0 N N N 28.285 18.579 24.488 -9.073 -3.460 -0.490 H261 3W5 64 3W5 H262 H262 H 0 0 N N N 27.682 16.915 24.177 -7.560 -3.703 0.420 H262 3W5 65 # 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 3W5 C1 C2 SING Y N 1 3W5 C1 C6 DOUB Y N 2 3W5 C2 C3 DOUB Y N 3 3W5 C3 C4 SING Y N 4 3W5 C3 O2 SING N N 5 3W5 C4 C5 DOUB Y N 6 3W5 C5 C6 SING Y N 7 3W5 C6 C7 SING N N 8 3W5 C7 C8 TRIP N N 9 3W5 C8 C9 SING N N 10 3W5 C9 C10 SING N N 11 3W5 C9 C13 SING N N 12 3W5 C9 O1 SING N N 13 3W5 C10 N1 SING N N 14 3W5 N1 C11 SING N N 15 3W5 N1 C15 SING N N 16 3W5 C11 C12 SING N N 17 3W5 C12 C13 SING N N 18 3W5 C13 C14 SING N N 19 3W5 C14 C15 SING N N 20 3W5 O2 C16 SING N N 21 3W5 C16 C17 DOUB Y N 22 3W5 C16 C21 SING Y N 23 3W5 C17 C18 SING Y N 24 3W5 C18 C19 DOUB Y N 25 3W5 C19 C20 SING Y N 26 3W5 C19 C22 SING N N 27 3W5 C20 C21 DOUB Y N 28 3W5 C22 O3 DOUB N N 29 3W5 C22 N2 SING N N 30 3W5 N2 C23 SING N N 31 3W5 C23 C24 SING N N 32 3W5 C23 C27 SING N N 33 3W5 C24 C25 SING N N 34 3W5 C25 C26 SING N N 35 3W5 C26 S1 SING N N 36 3W5 S1 O4 DOUB N N 37 3W5 S1 O5 DOUB N N 38 3W5 S1 C27 SING N N 39 3W5 C1 H1 SING N N 40 3W5 C2 H2 SING N N 41 3W5 C4 H4 SING N N 42 3W5 C5 H5 SING N N 43 3W5 C10 H101 SING N N 44 3W5 C10 H102 SING N N 45 3W5 C13 H13 SING N N 46 3W5 O1 HA SING N N 47 3W5 C11 H111 SING N N 48 3W5 C11 H112 SING N N 49 3W5 C15 H151 SING N N 50 3W5 C15 H152 SING N N 51 3W5 C12 H121 SING N N 52 3W5 C12 H122 SING N N 53 3W5 C14 H141 SING N N 54 3W5 C14 H142 SING N N 55 3W5 C17 H17 SING N N 56 3W5 C21 H21 SING N N 57 3W5 C18 H18 SING N N 58 3W5 C20 H20 SING N N 59 3W5 N2 HB SING N N 60 3W5 C23 H23 SING N N 61 3W5 C24 H241 SING N N 62 3W5 C24 H242 SING N N 63 3W5 C27 H271 SING N N 64 3W5 C27 H272 SING N N 65 3W5 C25 H251 SING N N 66 3W5 C25 H252 SING N N 67 3W5 C26 H261 SING N N 68 3W5 C26 H262 SING N N 69 # 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 3W5 SMILES ACDLabs 12.01 "O=S5(=O)CCCC(NC(=O)c4ccc(Oc3ccc(C#CC2(O)C1CCN(CC1)C2)cc3)cc4)C5" 3W5 InChI InChI 1.03 "InChI=1S/C27H30N2O5S/c30-26(28-23-2-1-17-35(32,33)18-23)21-5-9-25(10-6-21)34-24-7-3-20(4-8-24)11-14-27(31)19-29-15-12-22(27)13-16-29/h3-10,22-23,31H,1-2,12-13,15-19H2,(H,28,30)/t23-,27-/m0/s1" 3W5 InChIKey InChI 1.03 IOEYWFCDGXVEFG-HOFKKMOUSA-N 3W5 SMILES_CANONICAL CACTVS 3.385 "O[C@]1(CN2CCC1CC2)C#Cc3ccc(Oc4ccc(cc4)C(=O)N[C@H]5CCC[S](=O)(=O)C5)cc3" 3W5 SMILES CACTVS 3.385 "O[C]1(CN2CCC1CC2)C#Cc3ccc(Oc4ccc(cc4)C(=O)N[CH]5CCC[S](=O)(=O)C5)cc3" 3W5 SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "c1cc(ccc1C#C[C@@]2(CN3CCC2CC3)O)Oc4ccc(cc4)C(=O)N[C@H]5CCCS(=O)(=O)C5" 3W5 SMILES "OpenEye OEToolkits" 1.9.2 "c1cc(ccc1C#CC2(CN3CCC2CC3)O)Oc4ccc(cc4)C(=O)NC5CCCS(=O)(=O)C5" # 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 3W5 "SYSTEMATIC NAME" ACDLabs 12.01 "N-[(3S)-1,1-dioxidotetrahydro-2H-thiopyran-3-yl]-4-(4-{[(3S)-3-hydroxy-1-azabicyclo[2.2.2]oct-3-yl]ethynyl}phenoxy)benzamide" 3W5 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "N-[(3S)-1,1-bis(oxidanylidene)thian-3-yl]-4-[4-[2-[(3S)-3-oxidanyl-1-azabicyclo[2.2.2]octan-3-yl]ethynyl]phenoxy]benzamide" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 3W5 "Create component" 2011-11-11 EBI 3W5 "Modify descriptor" 2014-09-05 RCSB #