data_017
# 
_chem_comp.id                                    017 
_chem_comp.name                                  (3R,3AS,6AR)-HEXAHYDROFURO[2,3-B]FURAN-3-YL(1S,2R)-3-[[(4-AMINOPHENYL)SULFONYL](ISOBUTYL)AMINO]-1-BENZYL-2-HYDROXYPROPYLCARBAMATE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C27 H37 N3 O7 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "TMC114; UIC-94017" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-01-27 
_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                        547.664 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     017 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        ? 
_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 
017 N1   N1   N 0 1 N N N 21.091 28.735 14.067 -2.427 -0.346 -8.620 N1   017 1  
017 C2   C2   C 0 1 Y N N 20.540 27.566 14.519 -1.619 -0.037 -7.524 C2   017 2  
017 C3   C3   C 0 1 Y N N 19.188 27.333 14.210 -2.191 0.418  -6.343 C3   017 3  
017 C4   C4   C 0 1 Y N N 18.626 26.160 14.675 -1.388 0.724  -5.262 C4   017 4  
017 C5   C5   C 0 1 Y N N 19.384 25.216 15.345 -0.017 0.575  -5.353 C5   017 5  
017 C6   C6   C 0 1 Y N N 20.711 25.423 15.721 0.556  0.127  -6.529 C6   017 6  
017 C7   C7   C 0 1 Y N N 21.263 26.646 15.292 -0.240 -0.185 -7.612 C7   017 7  
017 S8   S8   S 0 1 N N N 18.450 23.799 15.993 1.003  0.966  -3.971 S8   017 8  
017 O9   O9   O 0 1 N N N 17.257 23.466 15.069 0.244  1.864  -3.172 O9   017 9  
017 O10  O10  O 0 1 N N N 19.481 22.638 16.240 2.293  1.230  -4.505 O10  017 10 
017 N11  N11  N 0 1 N N N 17.794 24.157 17.584 1.163  -0.412 -3.068 N11  017 11 
017 C12  C12  C 0 1 N N N 18.783 24.426 18.632 2.263  -1.341 -3.338 C12  017 12 
017 C13  C13  C 0 1 N N N 18.400 23.856 20.006 3.134  -1.477 -2.088 C13  017 13 
017 C14  C14  C 0 1 N N N 18.368 22.352 19.893 4.283  -2.447 -2.370 C14  017 14 
017 C15  C15  C 0 1 N N N 19.503 24.335 20.920 3.703  -0.108 -1.711 C15  017 15 
017 C16  C16  C 0 1 N N N 16.505 24.894 17.564 0.204  -0.703 -1.999 C16  017 16 
017 C17  C17  C 0 1 N N R 15.394 23.964 18.158 0.702  -0.093 -0.687 C17  017 17 
017 O18  O18  O 0 1 N N N 14.232 24.764 18.409 0.831  1.321  -0.839 O18  017 18 
017 C19  C19  C 0 1 N N S 15.013 22.828 17.177 -0.298 -0.397 0.428  C19  017 19 
017 N20  N20  N 0 1 N N N 14.132 21.941 17.887 0.177  0.186  1.684  N20  017 20 
017 C21  C21  C 0 1 N N N 14.488 20.675 18.223 -0.135 -0.394 2.859  C21  017 21 
017 O22  O22  O 0 1 N N N 15.587 20.086 17.955 -0.812 -1.403 2.877  O22  017 22 
017 O23  O23  O 0 1 N N N 13.421 20.066 18.952 0.303  0.142  4.014  O23  017 23 
017 C24  C24  C 0 1 N N R 13.505 18.602 19.102 -0.034 -0.483 5.280  C24  017 24 
017 C25  C25  C 0 1 N N N 12.839 18.351 20.485 1.073  -1.464 5.704  C25  017 25 
017 O26  O26  O 0 1 N N N 11.412 18.470 20.284 1.656  -0.957 6.912  O26  017 26 
017 C27  C27  C 0 1 N N R 11.220 17.978 18.968 0.668  -0.145 7.574  C27  017 27 
017 O28  O28  O 0 1 N N N 10.297 18.806 18.291 1.337  0.895  8.301  O28  017 28 
017 C29  C29  C 0 1 N N N 11.042 19.444 17.241 1.542  2.036  7.463  C29  017 29 
017 C30  C30  C 0 1 N N N 12.131 18.432 16.818 0.935  1.717  6.081  C30  017 30 
017 C31  C31  C 0 1 N N S 12.470 17.887 18.213 -0.080 0.570  6.405  C31  017 31 
017 C32  C32  C 0 1 N N N 14.294 23.285 15.896 -1.659 0.203  0.070  C32  017 32 
017 C33  C33  C 0 1 Y N N 12.549 21.750 14.881 -2.793 0.784  2.225  C33  017 33 
017 C34  C34  C 0 1 Y N N 12.148 20.661 14.069 -3.697 0.509  3.233  C34  017 34 
017 C35  C35  C 0 1 Y N N 13.119 19.933 13.391 -4.455 -0.646 3.187  C35  017 35 
017 C36  C36  C 0 1 Y N N 14.471 20.240 13.517 -4.308 -1.526 2.131  C36  017 36 
017 C37  C37  C 0 1 Y N N 14.860 21.326 14.314 -3.406 -1.249 1.120  C37  017 37 
017 C38  C38  C 0 1 Y N N 13.902 22.114 14.968 -2.645 -0.096 1.170  C38  017 38 
017 H11  1H1  H 0 1 N N N 21.928 28.931 14.259 -2.026 -0.665 -9.444 H11  017 39 
017 H12  2H1  H 0 1 N N N 20.610 29.291 13.584 -3.390 -0.243 -8.557 H12  017 40 
017 H3   H3   H 0 1 N N N 18.682 27.956 13.702 -3.262 0.534  -6.271 H3   017 41 
017 H4   H4   H 0 1 N N N 17.701 25.998 14.533 -1.833 1.078  -4.343 H4   017 42 
017 H6   H6   H 0 1 N N N 21.205 24.788 16.227 1.628  0.013  -6.597 H6   017 43 
017 H7   H7   H 0 1 N N N 22.157 26.855 15.535 0.207  -0.540 -8.529 H7   017 44 
017 H121 1H12 H 0 0 N N N 18.902 25.406 18.715 1.857  -2.316 -3.607 H121 017 45 
017 H122 2H12 H 0 0 N N N 19.652 24.040 18.357 2.867  -0.959 -4.161 H122 017 46 
017 H13  H13  H 0 1 N N N 17.513 24.210 20.303 2.530  -1.859 -1.264 H13  017 47 
017 H141 1H14 H 0 0 N N N 17.660 22.086 19.270 4.903  -2.545 -1.479 H141 017 48 
017 H142 2H14 H 0 0 N N N 18.190 21.962 20.775 3.877  -3.423 -2.639 H142 017 49 
017 H143 3H14 H 0 0 N N N 19.232 22.031 19.562 4.887  -2.066 -3.193 H143 017 50 
017 H151 1H15 H 0 0 N N N 19.488 25.314 20.965 4.307  0.272  -2.534 H151 017 51 
017 H152 2H15 H 0 0 N N N 20.369 24.038 20.570 2.885  0.582  -1.509 H152 017 52 
017 H153 3H15 H 0 0 N N N 19.368 23.965 21.817 4.324  -0.206 -0.820 H153 017 53 
017 H161 1H16 H 0 0 N N N 16.273 25.147 16.635 0.106  -1.783 -1.883 H161 017 54 
017 H162 2H16 H 0 0 N N N 16.579 25.721 18.103 -0.764 -0.275 -2.254 H162 017 55 
017 H17  H17  H 0 1 N N N 15.717 23.568 19.018 1.671  -0.521 -0.432 H17  017 56 
017 H18  H18  H 0 1 N N N 13.558 24.200 18.769 -0.046 1.659  -1.063 H18  017 57 
017 H19  H19  H 0 1 N N N 15.841 22.328 16.923 -0.397 -1.477 0.544  H19  017 58 
017 H20  H20  H 0 1 N N N 13.331 22.230 18.111 0.718  0.991  1.670  H20  017 59 
017 H24  H24  H 0 1 N N N 14.433 18.236 19.023 -0.990 -1.000 5.204  H24  017 60 
017 H251 1H25 H 0 0 N N N 13.067 17.448 20.819 1.832  -1.526 4.924  H251 017 61 
017 H252 2H25 H 0 0 N N N 13.152 19.020 21.145 0.644  -2.450 5.886  H252 017 62 
017 H27  H27  H 0 1 N N N 10.827 17.060 19.033 -0.001 -0.731 8.204  H27  017 63 
017 H291 1H29 H 0 0 N N N 11.455 20.283 17.568 2.609  2.233  7.362  H291 017 64 
017 H292 2H29 H 0 0 N N N 10.451 19.659 16.476 1.044  2.905  7.894  H292 017 65 
017 H301 1H30 H 0 0 N N N 11.775 17.729 16.219 1.705  1.368  5.392  H301 017 66 
017 H302 2H30 H 0 0 N N N 12.907 18.875 16.392 0.418  2.586  5.676  H302 017 67 
017 H31  H31  H 0 1 N N N 12.727 16.924 18.129 -1.080 0.924  6.655  H31  017 68 
017 H321 1H32 H 0 0 N N N 14.884 23.905 15.400 -2.014 -0.231 -0.863 H321 017 69 
017 H322 2H32 H 0 0 N N N 13.476 23.783 16.148 -1.561 1.282  -0.044 H322 017 70 
017 H33  H33  H 0 1 N N N 11.898 22.238 15.371 -2.201 1.687  2.261  H33  017 71 
017 H34  H34  H 0 1 N N N 11.230 20.432 13.989 -3.812 1.197  4.058  H34  017 72 
017 H35  H35  H 0 1 N N N 12.855 19.212 12.831 -5.161 -0.861 3.975  H35  017 73 
017 H36  H36  H 0 1 N N N 15.125 19.718 13.067 -4.899 -2.429 2.095  H36  017 74 
017 H37  H37  H 0 1 N N N 15.783 21.530 14.412 -3.292 -1.937 0.296  H37  017 75 
# 
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 
017 N1  C2   SING N N 1  
017 N1  H11  SING N N 2  
017 N1  H12  SING N N 3  
017 C2  C3   DOUB Y N 4  
017 C2  C7   SING Y N 5  
017 C3  C4   SING Y N 6  
017 C3  H3   SING N N 7  
017 C4  C5   DOUB Y N 8  
017 C4  H4   SING N N 9  
017 C5  C6   SING Y N 10 
017 C5  S8   SING N N 11 
017 C6  C7   DOUB Y N 12 
017 C6  H6   SING N N 13 
017 C7  H7   SING N N 14 
017 S8  O9   DOUB N N 15 
017 S8  O10  DOUB N N 16 
017 S8  N11  SING N N 17 
017 N11 C12  SING N N 18 
017 N11 C16  SING N N 19 
017 C12 C13  SING N N 20 
017 C12 H121 SING N N 21 
017 C12 H122 SING N N 22 
017 C13 C14  SING N N 23 
017 C13 C15  SING N N 24 
017 C13 H13  SING N N 25 
017 C14 H141 SING N N 26 
017 C14 H142 SING N N 27 
017 C14 H143 SING N N 28 
017 C15 H151 SING N N 29 
017 C15 H152 SING N N 30 
017 C15 H153 SING N N 31 
017 C16 C17  SING N N 32 
017 C16 H161 SING N N 33 
017 C16 H162 SING N N 34 
017 C17 O18  SING N N 35 
017 C17 C19  SING N N 36 
017 C17 H17  SING N N 37 
017 O18 H18  SING N N 38 
017 C19 N20  SING N N 39 
017 C19 C32  SING N N 40 
017 C19 H19  SING N N 41 
017 N20 C21  SING N N 42 
017 N20 H20  SING N N 43 
017 C21 O22  DOUB N N 44 
017 C21 O23  SING N N 45 
017 O23 C24  SING N N 46 
017 C24 C25  SING N N 47 
017 C24 C31  SING N N 48 
017 C24 H24  SING N N 49 
017 C25 O26  SING N N 50 
017 C25 H251 SING N N 51 
017 C25 H252 SING N N 52 
017 O26 C27  SING N N 53 
017 C27 O28  SING N N 54 
017 C27 C31  SING N N 55 
017 C27 H27  SING N N 56 
017 O28 C29  SING N N 57 
017 C29 C30  SING N N 58 
017 C29 H291 SING N N 59 
017 C29 H292 SING N N 60 
017 C30 C31  SING N N 61 
017 C30 H301 SING N N 62 
017 C30 H302 SING N N 63 
017 C31 H31  SING N N 64 
017 C32 C38  SING N N 65 
017 C32 H321 SING N N 66 
017 C32 H322 SING N N 67 
017 C33 C34  DOUB Y N 68 
017 C33 C38  SING Y N 69 
017 C33 H33  SING N N 70 
017 C34 C35  SING Y N 71 
017 C34 H34  SING N N 72 
017 C35 C36  DOUB Y N 73 
017 C35 H35  SING N N 74 
017 C36 C37  SING Y N 75 
017 C36 H36  SING N N 76 
017 C37 C38  DOUB Y N 77 
017 C37 H37  SING N N 78 
# 
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 
017 SMILES           ACDLabs              10.04 O=S(=O)(c1ccc(N)cc1)N(CC(C)C)CC(O)C(NC(=O)OC2COC3OCCC23)Cc4ccccc4 
017 InChI            InChI                1.02b 
InChI=1/C27H37N3O7S/c1-18(2)15-30(38(33,34)21-10-8-20(28)9-11-21)16-24(31)23(14-19-6-4-3-5-7-19)29-27(32)37-25-17-36-26-22(25)12-13-35-26/h3-11,18,22-26,31H,12-17,28H2,1-2H3,(H,29,32)/t22-,23-,24+,25-,26+/m0/s1/f/h29H 
017 InChIKey         InChI                1.02b CJBJHOAVZSMMDJ-QSHSPGAWDK 
017 SMILES_CANONICAL CACTVS               3.341 CC(C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O[C@H]2CO[C@H]3OCC[C@@H]23)[S](=O)(=O)c4ccc(N)cc4 
017 SMILES           CACTVS               3.341 CC(C)CN(C[CH](O)[CH](Cc1ccccc1)NC(=O)O[CH]2CO[CH]3OCC[CH]23)[S](=O)(=O)c4ccc(N)cc4 
017 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(C)C[N@@](C[C@H]([C@H](Cc1ccccc1)NC(=O)O[C@H]2CO[C@@H]3[C@H]2CCO3)O)S(=O)(=O)c4ccc(cc4)N 
017 SMILES           "OpenEye OEToolkits" 1.5.0 CC(C)CN(CC(C(Cc1ccccc1)NC(=O)OC2COC3C2CCO3)O)S(=O)(=O)c4ccc(cc4)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 
017 "SYSTEMATIC NAME" ACDLabs              10.04 "(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl [(1S,2R)-3-{[(4-aminophenyl)sulfonyl](2-methylpropyl)amino}-1-benzyl-2-hydroxypropyl]carbamate"                       
017 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(3R,3aS,6aR)-2,3,3a,4,5,6a-hexahydrofuro[5,4-b]furan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenyl-butan-2-yl]carbamate" 
# 
