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                    2008-10-14 
_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 N N 15 
D4N C8  C13  SING N N 16 
D4N C9  C10  SING N N 17 
D4N C10 C11  DOUB N N 18 
D4N C11 C12  SING N N 19 
D4N C11 S14  SING Y N 20 
D4N C12 C13  DOUB Y N 21 
D4N C18 N17  SING Y N 22 
D4N C18 C19  SING N N 23 
D4N S14 O15  DOUB Y N 24 
D4N S14 O16  DOUB N N 25 
D4N S14 N17  SING Y N 26 
D4N N17 C22  SING N N 27 
D4N C22 C68  SING Y 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 InChI            InChI                1.02b InChI=1/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/f/h23H2 
D4N InChIKey         InChI                1.02b YJFULAYRAKPBCY-RAGLUMLBDQ                                                                                                                                                   
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                                                                                                                 
# 
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 
# 
