data_D4N # _chem_comp.id D4N _chem_comp.name "1-{[(3R)-3-methyl-4-({4-[(1S)-2,2,2-trifluoro-1-hydroxy-1-methylethyl]phenyl}sulfonyl)piperazin-1-yl]methyl}cyclopropanecarboxamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C19 H26 F3 N3 O4 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2008-05-15 _chem_comp.pdbx_modified_date 2011-06-04 _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 449.488 _chem_comp.one_letter_code ? _chem_comp.three_letter_code D4N _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 3D4N _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 D4N O1 O1 O 0 1 N N N 10.660 34.037 6.634 -6.285 1.415 -1.025 O1 D4N 1 D4N C1 C1 C 0 1 N N N 11.050 35.309 4.668 -4.344 2.276 0.006 C1 D4N 2 D4N C2 C2 C 0 1 N N N 10.479 40.032 -0.707 4.380 2.063 0.045 C2 D4N 3 D4N C3 C3 C 0 1 N N N 10.797 34.024 5.420 -5.604 1.449 -0.022 C3 D4N 4 D4N C5 C5 C 0 1 N N S 9.742 39.430 -1.899 4.771 0.592 0.197 C5 D4N 5 D4N C6 C6 C 0 1 N N N 10.636 36.568 5.412 -3.941 2.992 -1.284 C6 D4N 6 D4N C7 C7 C 0 1 N N N 8.766 40.442 -2.487 5.802 0.226 -0.873 C7 D4N 7 D4N C8 C8 C 0 1 Y N N 9.030 38.169 -1.496 3.548 -0.273 0.032 C8 D4N 8 D4N C9 C9 C 0 1 Y N N 9.570 36.941 -1.860 3.044 -0.971 1.114 C9 D4N 9 D4N C10 C10 C 0 1 Y N N 8.941 35.756 -1.498 1.922 -1.764 0.963 C10 D4N 10 D4N C11 C11 C 0 1 Y N N 7.760 35.787 -0.771 1.303 -1.859 -0.269 C11 D4N 11 D4N C12 C12 C 0 1 Y N N 7.218 37.017 -0.410 1.806 -1.160 -1.351 C12 D4N 12 D4N C13 C13 C 0 1 Y N N 7.848 38.206 -0.768 2.925 -0.363 -1.199 C13 D4N 13 D4N C14 C14 C 0 1 N N N 12.113 36.178 5.322 -4.493 3.794 -0.105 C14 D4N 14 D4N C18 C18 C 0 1 N N N 7.467 34.499 2.187 -2.108 -1.166 -1.223 C18 D4N 15 D4N F4 F4 F 0 1 N N N 11.421 39.194 -0.315 3.816 2.268 -1.218 F4 D4N 16 D4N F1 F1 F 0 1 N N N 9.649 40.253 0.295 3.448 2.402 1.033 F1 D4N 17 D4N F3 F3 F 0 1 N N N 11.024 41.179 -1.076 5.518 2.865 0.184 F3 D4N 18 D4N O6 O6 O 0 1 N N N 10.722 39.078 -2.879 5.334 0.380 1.493 O6 D4N 19 D4N S14 S14 S 0 1 N N N 7.038 34.418 -0.361 -0.127 -2.869 -0.461 S14 D4N 20 D4N O15 O15 O 0 1 N N N 7.161 33.503 -1.458 -0.197 -3.208 -1.839 O15 D4N 21 D4N O16 O16 O 0 1 N N N 5.651 34.654 -0.093 -0.075 -3.839 0.576 O16 D4N 22 D4N N17 N17 N 0 1 N N N 7.693 33.715 0.946 -1.446 -1.918 -0.147 N17 D4N 23 D4N C22 C22 C 0 1 N N R 9.093 33.307 0.674 -1.985 -1.802 1.217 C22 D4N 24 D4N C68 C68 C 0 1 N N N 9.313 31.911 1.252 -3.356 -2.477 1.286 C68 D4N 25 D4N C21 C21 C 0 1 N N N 10.139 34.291 1.189 -2.125 -0.315 1.560 C21 D4N 26 D4N C19 C19 C 0 1 N N N 8.642 35.353 2.653 -2.243 0.296 -0.784 C19 D4N 27 D4N N20 N20 N 0 1 N N N 9.884 34.579 2.599 -2.919 0.352 0.520 N20 D4N 28 D4N C23 C23 C 0 1 N N N 11.003 35.363 3.141 -3.222 1.739 0.897 C23 D4N 29 D4N N1 N1 N 0 1 N N N 10.736 32.908 4.702 -5.974 0.748 1.068 N1 D4N 30 D4N H6 H6 H 0 1 N N N 10.105 37.468 5.068 -2.875 3.080 -1.499 H6 D4N 31 D4N H6A H6A H 0 1 N N N 9.930 36.816 6.218 -4.586 2.865 -2.153 H6A D4N 32 D4N H7 H7 H 0 1 N N N 8.531 41.207 -1.732 6.687 0.851 -0.754 H7 D4N 33 D4N H7A H7A H 0 1 N N N 9.221 40.922 -3.366 6.081 -0.823 -0.765 H7A D4N 34 D4N H7B H7B H 0 1 N N N 7.841 39.927 -2.788 5.373 0.388 -1.862 H7B D4N 35 D4N H9 H9 H 0 1 N N N 10.487 36.908 -2.430 3.528 -0.897 2.077 H9 D4N 36 D4N H10 H10 H 0 1 N N N 9.373 34.808 -1.783 1.530 -2.310 1.808 H10 D4N 37 D4N H12 H12 H 0 1 N N N 6.298 37.050 0.155 1.323 -1.234 -2.314 H12 D4N 38 D4N H13 H13 H 0 1 N N N 7.419 39.154 -0.480 3.316 0.186 -2.043 H13 D4N 39 D4N H14 H14 H 0 1 N N N 12.849 35.951 6.107 -5.502 4.196 -0.198 H14 D4N 40 D4N H14A H14A H 0 0 N N N 13.044 36.668 5.001 -3.792 4.411 0.457 H14A D4N 41 D4N H18 H18 H 0 1 N N N 6.621 35.176 2.000 -1.507 -1.221 -2.131 H18 D4N 42 D4N H18A H18A H 0 0 N N N 7.293 33.762 2.984 -3.096 -1.585 -1.408 H18A D4N 43 D4N HO6 HO6 H 0 1 N N N 10.306 39.000 -3.730 4.734 0.592 2.221 HO6 D4N 44 D4N H22 H22 H 0 1 N N N 9.231 33.300 -0.417 -1.305 -2.281 1.921 H22 D4N 45 D4N H68 H68 H 0 1 N N N 9.366 31.179 0.433 -3.256 -3.531 1.024 H68 D4N 46 D4N H68A H68A H 0 0 N N N 10.255 31.894 1.820 -3.754 -2.390 2.297 H68A D4N 47 D4N H68B H68B H 0 0 N N N 8.477 31.655 1.919 -4.036 -1.992 0.585 H68B D4N 48 D4N H21 H21 H 0 1 N N N 11.141 33.851 1.080 -2.626 -0.210 2.523 H21 D4N 49 D4N H21A H21A H 0 0 N N N 10.083 35.223 0.608 -1.137 0.141 1.612 H21A D4N 50 D4N H19 H19 H 0 1 N N N 8.734 36.231 1.997 -1.253 0.744 -0.699 H19 D4N 51 D4N H19A H19A H 0 0 N N N 8.464 35.673 3.690 -2.829 0.845 -1.521 H19A D4N 52 D4N H23 H23 H 0 1 N N N 10.882 36.411 2.829 -2.331 2.353 0.769 H23 D4N 53 D4N H23A H23A H 0 0 N N N 11.940 34.935 2.754 -3.539 1.771 1.939 H23A D4N 54 D4N HN1 HN1 H 0 1 N N N 10.566 32.126 5.302 -6.819 0.272 1.075 HN1 D4N 55 D4N HN1A HN1A H 0 0 N N N 10.844 32.857 3.709 -5.396 0.720 1.847 HN1A D4N 56 # 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 D4N O1 C3 DOUB N N 1 D4N C1 C3 SING N N 2 D4N C1 C6 SING N N 3 D4N C1 C14 SING N N 4 D4N C1 C23 SING N N 5 D4N C2 C5 SING N N 6 D4N C2 F4 SING N N 7 D4N C2 F1 SING N N 8 D4N C2 F3 SING N N 9 D4N C3 N1 SING N N 10 D4N C5 C7 SING N N 11 D4N C5 C8 SING N N 12 D4N C5 O6 SING N N 13 D4N C6 C14 SING N N 14 D4N C8 C9 DOUB Y N 15 D4N C8 C13 SING Y N 16 D4N C9 C10 SING Y N 17 D4N C10 C11 DOUB Y N 18 D4N C11 C12 SING Y N 19 D4N C11 S14 SING N N 20 D4N C12 C13 DOUB Y N 21 D4N C18 N17 SING N N 22 D4N C18 C19 SING N N 23 D4N S14 O15 DOUB N N 24 D4N S14 O16 DOUB N N 25 D4N S14 N17 SING N N 26 D4N N17 C22 SING N N 27 D4N C22 C68 SING N N 28 D4N C22 C21 SING N N 29 D4N C21 N20 SING N N 30 D4N C19 N20 SING N N 31 D4N N20 C23 SING N N 32 D4N C6 H6 SING N N 33 D4N C6 H6A SING N N 34 D4N C7 H7 SING N N 35 D4N C7 H7A SING N N 36 D4N C7 H7B SING N N 37 D4N C9 H9 SING N N 38 D4N C10 H10 SING N N 39 D4N C12 H12 SING N N 40 D4N C13 H13 SING N N 41 D4N C14 H14 SING N N 42 D4N C14 H14A SING N N 43 D4N C18 H18 SING N N 44 D4N C18 H18A SING N N 45 D4N O6 HO6 SING N N 46 D4N C22 H22 SING N N 47 D4N C68 H68 SING N N 48 D4N C68 H68A SING N N 49 D4N C68 H68B SING N N 50 D4N C21 H21 SING N N 51 D4N C21 H21A SING N N 52 D4N C19 H19 SING N N 53 D4N C19 H19A SING N N 54 D4N C23 H23 SING N N 55 D4N C23 H23A SING N N 56 D4N N1 HN1 SING N N 57 D4N N1 HN1A SING N N 58 # 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 D4N SMILES ACDLabs 10.04 "FC(F)(F)C(O)(c1ccc(cc1)S(=O)(=O)N3C(CN(CC2(C(=O)N)CC2)CC3)C)C" D4N SMILES_CANONICAL CACTVS 3.341 "C[C@@H]1CN(CCN1[S](=O)(=O)c2ccc(cc2)[C@](C)(O)C(F)(F)F)CC3(CC3)C(N)=O" D4N SMILES CACTVS 3.341 "C[CH]1CN(CCN1[S](=O)(=O)c2ccc(cc2)[C](C)(O)C(F)(F)F)CC3(CC3)C(N)=O" D4N SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C[C@@H]1C[N@](CC[N@]1S(=O)(=O)c2ccc(cc2)[C@@](C)(C(F)(F)F)O)CC3(CC3)C(=O)N" D4N SMILES "OpenEye OEToolkits" 1.5.0 "CC1CN(CCN1S(=O)(=O)c2ccc(cc2)C(C)(C(F)(F)F)O)CC3(CC3)C(=O)N" D4N InChI InChI 1.03 "InChI=1S/C19H26F3N3O4S/c1-13-11-24(12-18(7-8-18)16(23)26)9-10-25(13)30(28,29)15-5-3-14(4-6-15)17(2,27)19(20,21)22/h3-6,13,27H,7-12H2,1-2H3,(H2,23,26)/t13-,17+/m1/s1" D4N InChIKey InChI 1.03 YJFULAYRAKPBCY-DYVFJYSZSA-N # 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 D4N "SYSTEMATIC NAME" ACDLabs 10.04 "1-{[(3R)-3-methyl-4-({4-[(1S)-2,2,2-trifluoro-1-hydroxy-1-methylethyl]phenyl}sulfonyl)piperazin-1-yl]methyl}cyclopropanecarboxamide" D4N "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "1-[[(1S,3R,4R)-3-methyl-4-[4-[(2S)-1,1,1-trifluoro-2-hydroxy-propan-2-yl]phenyl]sulfonyl-piperazin-1-yl]methyl]cyclopropane-1-carboxamide" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site D4N "Create component" 2008-05-15 RCSB D4N "Modify aromatic_flag" 2011-06-04 RCSB D4N "Modify descriptor" 2011-06-04 RCSB #