data_3W4 # _chem_comp.id 3W4 _chem_comp.name "N-[(3R)-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 3W4 _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 3W4 C1 C1 C 0 1 Y N N 56.243 -14.310 22.908 2.804 0.488 0.371 C1 3W4 1 3W4 C2 C2 C 0 1 Y N N 55.431 -13.441 23.600 1.627 1.158 0.112 C2 3W4 2 3W4 C3 C3 C 0 1 Y N N 55.792 -13.038 24.875 1.659 2.443 -0.414 C3 3W4 3 3W4 C4 C4 C 0 1 Y N N 56.949 -13.470 25.491 2.875 3.058 -0.682 C4 3W4 4 3W4 C5 C5 C 0 1 Y N N 57.761 -14.343 24.798 4.056 2.394 -0.427 C5 3W4 5 3W4 C6 C6 C 0 1 Y N N 57.406 -14.752 23.522 4.028 1.103 0.103 C6 3W4 6 3W4 C7 C7 C 0 1 N N N 58.317 -15.651 22.870 5.253 0.411 0.370 C7 3W4 7 3W4 C8 C8 C 0 1 N N N 59.157 -16.366 22.367 6.257 -0.156 0.590 C8 3W4 8 3W4 C9 C9 C 0 1 N N S 60.263 -17.152 21.817 7.516 -0.868 0.865 C9 3W4 9 3W4 C10 C10 C 0 1 N N N 61.139 -17.742 22.939 8.703 0.023 0.484 C10 3W4 10 3W4 N1 N1 N 0 1 N N N 62.545 -17.391 22.612 9.501 -0.646 -0.552 N1 3W4 11 3W4 C11 C11 C 0 1 N N N 62.933 -17.989 21.295 10.054 -1.914 -0.056 C11 3W4 12 3W4 C12 C12 C 0 1 N N N 62.062 -17.371 20.188 8.906 -2.859 0.309 C12 3W4 13 3W4 C13 C13 C 0 1 N N N 61.076 -16.372 20.787 7.574 -2.152 0.029 C13 3W4 14 3W4 C14 C14 C 0 1 N N N 61.898 -15.278 21.444 7.524 -1.773 -1.456 C14 3W4 15 3W4 C15 C15 C 0 1 N N N 62.744 -15.894 22.570 8.711 -0.858 -1.773 C15 3W4 16 3W4 O1 O1 O 0 1 N N N 59.712 -18.207 21.091 7.589 -1.193 2.254 O1 3W4 17 3W4 O2 O2 O 0 1 N N N 55.025 -12.138 25.607 0.497 3.099 -0.668 O2 3W4 18 3W4 C16 C16 C 0 1 Y N N 53.665 -12.262 25.824 -0.669 2.466 -0.380 C16 3W4 19 3W4 C17 C17 C 0 1 Y N N 52.989 -13.460 25.722 -1.243 2.610 0.878 C17 3W4 20 3W4 C18 C18 C 0 1 Y N N 51.635 -13.468 25.959 -2.425 1.969 1.174 C18 3W4 21 3W4 C19 C19 C 0 1 Y N N 50.999 -12.300 26.322 -3.048 1.174 0.209 C19 3W4 22 3W4 C20 C20 C 0 1 Y N N 51.662 -11.110 26.430 -2.468 1.033 -1.055 C20 3W4 23 3W4 C21 C21 C 0 1 Y N N 53.019 -11.095 26.163 -1.288 1.681 -1.345 C21 3W4 24 3W4 C22 C22 C 0 1 N N N 49.562 -12.346 26.620 -4.315 0.485 0.522 C22 3W4 25 3W4 O3 O3 O 0 1 N N N 49.113 -11.656 27.528 -4.818 0.609 1.622 O3 3W4 26 3W4 N2 N2 N 0 1 N N N 48.892 -13.274 25.843 -4.914 -0.281 -0.410 N2 3W4 27 3W4 C23 C23 C 0 1 N N R 47.462 -13.479 25.842 -6.172 -0.965 -0.099 C23 3W4 28 3W4 C24 C24 C 0 1 N N N 46.529 -12.252 25.637 -6.318 -2.190 -0.997 C24 3W4 29 3W4 C25 C25 C 0 1 N N N 45.004 -12.475 25.682 -7.483 -3.061 -0.534 C25 3W4 30 3W4 C26 C26 C 0 1 N N N 44.666 -13.165 26.976 -8.809 -2.352 -0.815 C26 3W4 31 3W4 S1 S1 S 0 1 N N N 45.429 -14.775 26.840 -8.885 -0.826 0.168 S1 3W4 32 3W4 O4 O4 O 0 1 N N N 45.192 -15.177 25.454 -8.796 -1.167 1.545 O4 3W4 33 3W4 O5 O5 O 0 1 N N N 45.230 -15.620 28.005 -9.983 -0.047 -0.286 O5 3W4 34 3W4 C27 C27 C 0 1 N N N 47.155 -14.434 26.976 -7.342 -0.006 -0.328 C27 3W4 35 3W4 H1 H1 H 0 1 N N N 55.982 -14.639 21.913 2.779 -0.509 0.784 H1 3W4 36 3W4 H2 H2 H 0 1 N N N 54.519 -13.076 23.152 0.680 0.682 0.319 H2 3W4 37 3W4 H4 H4 H 0 1 N N N 57.210 -13.135 26.484 2.895 4.057 -1.092 H4 3W4 38 3W4 H5 H5 H 0 1 N N N 58.672 -14.708 25.249 5.001 2.873 -0.636 H5 3W4 39 3W4 H101 H101 H 0 0 N N N 60.856 -17.308 23.909 8.335 0.975 0.102 H101 3W4 40 3W4 H102 H102 H 0 0 N N N 61.020 -18.835 22.978 9.322 0.199 1.364 H102 3W4 41 3W4 H13 H13 H 0 1 N N N 60.421 -15.956 20.008 6.741 -2.806 0.289 H13 3W4 42 3W4 HA HA H 0 1 N N N 60.409 -18.736 20.721 7.562 -0.425 2.840 HA 3W4 43 3W4 H111 H111 H 0 0 N N N 63.993 -17.777 21.092 10.668 -2.371 -0.832 H111 3W4 44 3W4 H112 H112 H 0 0 N N N 62.776 -19.077 21.324 10.664 -1.724 0.827 H112 3W4 45 3W4 H151 H151 H 0 0 N N N 62.439 -15.460 23.533 8.344 0.101 -2.139 H151 3W4 46 3W4 H152 H152 H 0 0 N N N 63.806 -15.674 22.389 9.336 -1.324 -2.534 H152 3W4 47 3W4 H121 H121 H 0 0 N N N 62.708 -16.853 19.464 8.973 -3.765 -0.293 H121 3W4 48 3W4 H122 H122 H 0 0 N N N 61.504 -18.169 19.677 8.968 -3.116 1.367 H122 3W4 49 3W4 H141 H141 H 0 0 N N N 62.560 -14.815 20.697 7.586 -2.674 -2.066 H141 3W4 50 3W4 H142 H142 H 0 0 N N N 61.227 -14.514 21.863 6.593 -1.249 -1.668 H142 3W4 51 3W4 H17 H17 H 0 1 N N N 53.511 -14.369 25.462 -0.761 3.224 1.624 H17 3W4 52 3W4 H21 H21 H 0 1 N N N 53.571 -10.169 26.220 -0.841 1.576 -2.323 H21 3W4 53 3W4 H18 H18 H 0 1 N N N 51.072 -14.385 25.861 -2.870 2.080 2.152 H18 3W4 54 3W4 H20 H20 H 0 1 N N N 51.142 -10.208 26.715 -2.946 0.419 -1.804 H20 3W4 55 3W4 HB HB H 0 1 N N N 49.440 -13.848 25.235 -4.513 -0.380 -1.288 HB 3W4 56 3W4 H23 H23 H 0 1 N N N 47.279 -14.084 24.942 -6.163 -1.280 0.944 H23 3W4 57 3W4 H241 H241 H 0 0 N N N 46.774 -11.522 26.423 -6.498 -1.865 -2.022 H241 3W4 58 3W4 H242 H242 H 0 0 N N N 46.766 -11.824 24.652 -5.398 -2.773 -0.962 H242 3W4 59 3W4 H271 H271 H 0 0 N N N 47.740 -15.359 26.870 -7.198 0.894 0.270 H271 3W4 60 3W4 H272 H272 H 0 0 N N N 47.380 -13.966 27.946 -7.394 0.261 -1.384 H272 3W4 61 3W4 H251 H251 H 0 0 N N N 44.485 -11.507 25.630 -7.459 -4.010 -1.068 H251 3W4 62 3W4 H252 H252 H 0 0 N N N 44.695 -13.103 24.834 -7.392 -3.247 0.536 H252 3W4 63 3W4 H261 H261 H 0 0 N N N 45.079 -12.610 27.831 -8.874 -2.106 -1.875 H261 3W4 64 3W4 H262 H262 H 0 0 N N N 43.576 -13.260 27.092 -9.637 -3.005 -0.539 H262 3W4 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 3W4 C1 C2 SING Y N 1 3W4 C1 C6 DOUB Y N 2 3W4 C2 C3 DOUB Y N 3 3W4 C3 C4 SING Y N 4 3W4 C3 O2 SING N N 5 3W4 C4 C5 DOUB Y N 6 3W4 C5 C6 SING Y N 7 3W4 C6 C7 SING N N 8 3W4 C7 C8 TRIP N N 9 3W4 C8 C9 SING N N 10 3W4 C9 C10 SING N N 11 3W4 C9 C13 SING N N 12 3W4 C9 O1 SING N N 13 3W4 C10 N1 SING N N 14 3W4 N1 C11 SING N N 15 3W4 N1 C15 SING N N 16 3W4 C11 C12 SING N N 17 3W4 C12 C13 SING N N 18 3W4 C13 C14 SING N N 19 3W4 C14 C15 SING N N 20 3W4 O2 C16 SING N N 21 3W4 C16 C17 SING Y N 22 3W4 C16 C21 DOUB Y N 23 3W4 C17 C18 DOUB Y N 24 3W4 C18 C19 SING Y N 25 3W4 C19 C20 DOUB Y N 26 3W4 C19 C22 SING N N 27 3W4 C20 C21 SING Y N 28 3W4 C22 O3 DOUB N N 29 3W4 C22 N2 SING N N 30 3W4 N2 C23 SING N N 31 3W4 C23 C24 SING N N 32 3W4 C23 C27 SING N N 33 3W4 C24 C25 SING N N 34 3W4 C25 C26 SING N N 35 3W4 C26 S1 SING N N 36 3W4 S1 O4 DOUB N N 37 3W4 S1 O5 DOUB N N 38 3W4 S1 C27 SING N N 39 3W4 C1 H1 SING N N 40 3W4 C2 H2 SING N N 41 3W4 C4 H4 SING N N 42 3W4 C5 H5 SING N N 43 3W4 C10 H101 SING N N 44 3W4 C10 H102 SING N N 45 3W4 C13 H13 SING N N 46 3W4 O1 HA SING N N 47 3W4 C11 H111 SING N N 48 3W4 C11 H112 SING N N 49 3W4 C15 H151 SING N N 50 3W4 C15 H152 SING N N 51 3W4 C12 H121 SING N N 52 3W4 C12 H122 SING N N 53 3W4 C14 H141 SING N N 54 3W4 C14 H142 SING N N 55 3W4 C17 H17 SING N N 56 3W4 C21 H21 SING N N 57 3W4 C18 H18 SING N N 58 3W4 C20 H20 SING N N 59 3W4 N2 HB SING N N 60 3W4 C23 H23 SING N N 61 3W4 C24 H241 SING N N 62 3W4 C24 H242 SING N N 63 3W4 C27 H271 SING N N 64 3W4 C27 H272 SING N N 65 3W4 C25 H251 SING N N 66 3W4 C25 H252 SING N N 67 3W4 C26 H261 SING N N 68 3W4 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 3W4 SMILES ACDLabs 12.01 "O=S5(=O)CCCC(NC(=O)c4ccc(Oc3ccc(C#CC2(O)C1CCN(CC1)C2)cc3)cc4)C5" 3W4 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+/m1/s1" 3W4 InChIKey InChI 1.03 IOEYWFCDGXVEFG-KCWPFWIISA-N 3W4 SMILES_CANONICAL CACTVS 3.385 "O[C@]1(CN2CCC1CC2)C#Cc3ccc(Oc4ccc(cc4)C(=O)N[C@@H]5CCC[S](=O)(=O)C5)cc3" 3W4 SMILES CACTVS 3.385 "O[C]1(CN2CCC1CC2)C#Cc3ccc(Oc4ccc(cc4)C(=O)N[CH]5CCC[S](=O)(=O)C5)cc3" 3W4 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" 3W4 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 3W4 "SYSTEMATIC NAME" ACDLabs 12.01 "N-[(3R)-1,1-dioxidotetrahydro-2H-thiopyran-3-yl]-4-(4-{[(3S)-3-hydroxy-1-azabicyclo[2.2.2]oct-3-yl]ethynyl}phenoxy)benzamide" 3W4 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "N-[(3R)-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 3W4 "Create component" 2011-11-11 EBI 3W4 "Modify name" 2011-11-22 EBI 3W4 "Modify descriptor" 2014-09-05 RCSB #