data_385
# 
_chem_comp.id                                    385 
_chem_comp.name                                  "(3R,3AS,6AR)-HEXAHYDROFURO[2,3-B]FURAN-3-YL [(1S,2R)-3-[(1,3-BENZODIOXOL-5-YLSULFONYL)(ISOBUTYL)AMINO]-2-HYDROXY-1-{4-[(2-METHYL-1,3-THIAZOL-4-YL)METHOXY]BENZYL}PROPYL]CARBAMATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C33 H41 N3 O10 S2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-01-23 
_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                        703.823 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     385 
_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        2FDD 
_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 
385 C1   C1   C 0 1 N N S 19.112 16.455 -2.668 1.505   -4.687 -1.056 C1   385 1  
385 C2   C2   C 0 1 N N R 19.116 17.832 -3.321 1.070   -5.997 -0.325 C2   385 2  
385 C3   C3   C 0 1 N N R 17.858 15.745 -3.283 1.092   -3.588 -0.055 C3   385 3  
385 C4   C4   C 0 1 N N N 19.173 16.754 -1.138 0.504   -4.692 -2.261 C4   385 4  
385 O5   O5   O 0 1 N N N 18.113 17.838 -4.343 -0.106  -5.611 0.413  O5   385 5  
385 O6   O6   O 0 1 N N N 18.829 18.825 -2.317 0.686   -6.911 -1.361 O6   385 6  
385 C7   C7   C 0 1 N N N 17.705 16.476 -4.613 0.093   -4.274 0.893  C7   385 7  
385 O8   O8   O 0 1 N N N 16.651 15.891 -2.502 0.454   -2.485 -0.751 O8   385 8  
385 C9   C9   C 0 1 N N N 18.542 18.180 -1.065 0.320   -6.198 -2.546 C9   385 9  
385 C10  C10  C 0 1 N N N 16.136 14.953 -1.671 0.526   -1.239 -0.246 C10  385 10 
385 N11  N11  N 0 1 N N N 15.273 15.328 -0.726 -0.066  -0.215 -0.891 N11  385 11 
385 O12  O12  O 0 1 N N N 16.463 13.788 -1.789 1.126   -1.038 0.792  O12  385 12 
385 C13  C13  C 0 1 N N S 14.563 14.558 0.301  0.013   1.141  -0.341 C13  385 13 
385 C14  C14  C 0 1 N N N 14.904 15.185 1.695  -0.622  1.165  1.051  C14  385 14 
385 C15  C15  C 0 1 N N R 13.050 14.433 -0.053 1.479   1.566  -0.241 C15  385 15 
385 C16  C16  C 0 1 Y N N 16.319 15.478 2.019  -2.095  0.866  0.937  C16  385 16 
385 C17  C17  C 0 1 N N N 12.278 13.350 0.724  2.113   1.543  -1.633 C17  385 17 
385 O18  O18  O 0 1 N N N 12.442 15.683 0.164  1.556   2.889  0.295  O18  385 18 
385 C19  C19  C 0 1 Y N N 16.765 16.821 2.171  -2.541  -0.441 1.008  C19  385 19 
385 C20  C20  C 0 1 Y N N 17.254 14.401 2.162  -2.998  1.899  0.766  C20  385 20 
385 N21  N21  N 0 1 N N N 12.779 12.037 0.392  3.513   1.966  -1.539 N21  385 21 
385 C22  C22  C 0 1 Y N N 18.143 17.097 2.459  -3.890  -0.718 0.903  C22  385 22 
385 C23  C23  C 0 1 Y N N 18.608 14.673 2.445  -4.347  1.627  0.656  C23  385 23 
385 S24  S24  S 0 1 N N N 13.607 11.174 1.629  4.712   0.834  -1.392 S24  385 24 
385 C25  C25  C 0 1 N N N 11.963 11.237 -0.519 3.851   3.391  -1.575 C25  385 25 
385 C26  C26  C 0 1 Y N N 19.054 16.018 2.590  -4.798  0.317  0.727  C26  385 26 
385 C27  C27  C 0 1 Y N N 12.400 10.483 2.667  4.959   0.547  0.329  C27  385 27 
385 O28  O28  O 0 1 N N N 14.482 12.019 2.399  4.169   -0.373 -1.911 O28  385 28 
385 O29  O29  O 0 1 N N N 14.394 10.100 1.075  5.899   1.466  -1.853 O29  385 29 
385 C30  C30  C 0 1 N N N 12.115 11.521 -2.032 3.577   3.945  -2.974 C30  385 30 
385 O31  O31  O 0 1 N N N 20.347 16.280 2.836  -6.126  0.047  0.624  O31  385 31 
385 C32  C32  C 0 1 Y N N 11.829 9.212  2.343  5.880   1.304  1.028  C32  385 32 
385 C33  C33  C 0 1 Y N N 11.954 11.186 3.830  4.235   -0.438 0.975  C33  385 33 
385 C34  C34  C 0 1 N N N 11.002 10.842 -2.849 3.806   5.458  -2.977 C34  385 34 
385 C35  C35  C 0 1 N N N 13.526 11.192 -2.577 4.523   3.284  -3.978 C35  385 35 
385 C36  C36  C 0 1 N N N 21.231 16.973 2.008  -6.790  1.301  0.451  C36  385 36 
385 C37  C37  C 0 1 Y N N 10.830 8.651  3.165  6.072   1.084  2.383  C37  385 37 
385 C38  C38  C 0 1 Y N N 10.949 10.620 4.656  4.426   -0.666 2.325  C38  385 38 
385 C39  C39  C 0 1 Y N N 22.679 16.629 2.314  -8.274  1.071  0.330  C39  385 39 
385 C40  C40  C 0 1 Y N N 10.383 9.351  4.320  5.343   0.092  3.034  C40  385 40 
385 O41  O41  O 0 1 N N N 10.154 7.485  3.058  6.900   1.682  3.288  O41  385 41 
385 N42  N42  N 0 1 Y N N 23.519 17.466 2.965  -9.102  2.081  0.169  N42  385 42 
385 C43  C43  C 0 1 Y N N 23.224 15.430 1.936  -8.790  -0.183 0.390  C43  385 43 
385 O44  O44  O 0 1 N N N 9.426  8.618  4.932  5.714   0.069  4.347  O44  385 44 
385 C45  C45  C 0 1 N N N 9.251  7.420  4.158  6.377   1.325  4.582  C45  385 45 
385 C46  C46  C 0 1 Y N N 24.709 16.985 3.117  -10.397 1.895  0.056  C46  385 46 
385 S47  S47  S 0 1 Y N N 24.866 15.396 2.437  -10.531 0.169  0.194  S47  385 47 
385 C48  C48  C 0 1 N N N 25.838 17.715 3.807  -11.488 2.917  -0.137 C48  385 48 
385 H1   H1   H 0 1 N N N 19.941 15.753 -2.842 2.553   -4.659 -1.354 H1   385 49 
385 H2   H2   H 0 1 N N N 20.095 18.060 -3.768 1.854   -6.398 0.318  H2   385 50 
385 H3   H3   H 0 1 N N N 18.000 14.656 -3.347 1.961   -3.234 0.500  H3   385 51 
385 H41  1H4  H 0 1 N N N 20.187 16.697 -0.717 0.937   -4.185 -3.123 H41  385 52 
385 H42  2H4  H 0 1 N N N 18.604 16.019 -0.550 -0.444  -4.234 -1.977 H42  385 53 
385 H71  1H7  H 0 1 N N N 16.674 16.424 -4.994 0.499   -4.301 1.904  H71  385 54 
385 H72  2H7  H 0 1 N N N 18.340 16.021 -5.387 -0.854  -3.734 0.887  H72  385 55 
385 H91  1H9  H 0 1 N N N 18.958 18.752 -0.223 0.965   -6.498 -3.372 H91  385 56 
385 H92  2H9  H 0 1 N N N 17.455 18.111 -0.910 -0.721  -6.403 -2.795 H92  385 57 
385 HN11 HN11 H 0 0 N N N 15.075 16.308 -0.716 -0.545  -0.375 -1.719 HN11 385 58 
385 H13  H13  H 0 1 N N N 14.896 13.511 0.347  -0.521  1.830  -0.996 H13  385 59 
385 H141 1H14 H 0 0 N N N 14.614 14.410 2.420  -0.146  0.413  1.680  H141 385 60 
385 H142 2H14 H 0 0 N N N 14.368 16.144 1.745  -0.485  2.150  1.496  H142 385 61 
385 H15  H15  H 0 1 N N N 13.006 14.117 -1.106 2.013   0.877  0.414  H15  385 62 
385 H171 1H17 H 0 0 N N N 11.214 13.405 0.451  1.572   2.222  -2.291 H171 385 63 
385 H172 2H17 H 0 0 N N N 12.403 13.522 1.803  2.066   0.531  -2.037 H172 385 64 
385 HO18 HO18 H 0 0 N N N 12.305 15.812 1.095  1.072   3.465  -0.312 HO18 385 65 
385 H19  H19  H 0 1 N N N 16.063 17.636 2.069  -1.834  -1.246 1.146  H19  385 66 
385 H20  H20  H 0 1 N N N 16.921 13.380 2.053  -2.646  2.919  0.711  H20  385 67 
385 H22  H22  H 0 1 N N N 18.483 18.116 2.575  -4.239  -1.738 0.959  H22  385 68 
385 H23  H23  H 0 1 N N N 19.309 13.859 2.552  -5.052  2.434  0.518  H23  385 69 
385 H251 1H25 H 0 0 N N N 10.921 11.496 -0.279 4.906   3.520  -1.332 H251 385 70 
385 H252 2H25 H 0 0 N N N 12.240 10.184 -0.359 3.243   3.927  -0.846 H252 385 71 
385 H30  H30  H 0 1 N N N 11.998 12.608 -2.155 2.545   3.733  -3.253 H30  385 72 
385 H32  H32  H 0 1 N N N 12.164 8.680  1.465  6.448   2.069  0.520  H32  385 73 
385 H33  H33  H 0 1 N N N 12.382 12.146 4.079  3.519   -1.029 0.424  H33  385 74 
385 H341 1H34 H 0 0 N N N 11.363 9.874  -3.227 3.611   5.853  -3.974 H341 385 75 
385 H342 2H34 H 0 0 N N N 10.724 11.486 -3.696 3.132   5.929  -2.262 H342 385 76 
385 H343 3H34 H 0 0 N N N 10.123 10.680 -2.208 4.839   5.670  -2.698 H343 385 77 
385 H351 1H35 H 0 0 N N N 13.869 10.236 -2.154 5.555   3.496  -3.699 H351 385 78 
385 H352 2H35 H 0 0 N N N 14.225 11.992 -2.291 4.360   2.206  -3.976 H352 385 79 
385 H353 3H35 H 0 0 N N N 13.487 11.114 -3.674 4.328   3.679  -4.976 H353 385 80 
385 H361 1H36 H 0 0 N N N 21.090 18.050 2.181  -6.590  1.939  1.312  H361 385 81 
385 H362 2H36 H 0 0 N N N 21.018 16.705 0.963  -6.422  1.785  -0.453 H362 385 82 
385 H38  H38  H 0 1 N N N 10.612 11.147 5.537  3.858   -1.436 2.827  H38  385 83 
385 H43  H43  H 0 1 N N N 22.708 14.640 1.411  -8.289  -1.131 0.521  H43  385 84 
385 H451 1H45 H 0 0 N N N 9.453  6.530  4.772  5.666   2.075  4.928  H451 385 85 
385 H452 2H45 H 0 0 N N N 8.215  7.352  3.794  7.187   1.202  5.301  H452 385 86 
385 H481 1H48 H 0 0 N N N 26.212 17.105 4.643  -12.453 2.413  -0.185 H481 385 87 
385 H482 2H48 H 0 0 N N N 25.471 18.678 4.191  -11.484 3.615  0.700  H482 385 88 
385 H483 3H48 H 0 0 N N N 26.653 17.892 3.090  -11.315 3.461  -1.065 H483 385 89 
# 
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 
385 C1  C2   SING N N 1  
385 C1  C3   SING N N 2  
385 C1  C4   SING N N 3  
385 C1  H1   SING N N 4  
385 C2  O5   SING N N 5  
385 C2  O6   SING N N 6  
385 C2  H2   SING N N 7  
385 C3  C7   SING N N 8  
385 C3  O8   SING N N 9  
385 C3  H3   SING N N 10 
385 C4  C9   SING N N 11 
385 C4  H41  SING N N 12 
385 C4  H42  SING N N 13 
385 O5  C7   SING N N 14 
385 O6  C9   SING N N 15 
385 C7  H71  SING N N 16 
385 C7  H72  SING N N 17 
385 O8  C10  SING N N 18 
385 C9  H91  SING N N 19 
385 C9  H92  SING N N 20 
385 C10 N11  SING N N 21 
385 C10 O12  DOUB N N 22 
385 N11 C13  SING N N 23 
385 N11 HN11 SING N N 24 
385 C13 C14  SING N N 25 
385 C13 C15  SING N N 26 
385 C13 H13  SING N N 27 
385 C14 C16  SING N N 28 
385 C14 H141 SING N N 29 
385 C14 H142 SING N N 30 
385 C15 C17  SING N N 31 
385 C15 O18  SING N N 32 
385 C15 H15  SING N N 33 
385 C16 C19  SING Y N 34 
385 C16 C20  DOUB Y N 35 
385 C17 N21  SING N N 36 
385 C17 H171 SING N N 37 
385 C17 H172 SING N N 38 
385 O18 HO18 SING N N 39 
385 C19 C22  DOUB Y N 40 
385 C19 H19  SING N N 41 
385 C20 C23  SING Y N 42 
385 C20 H20  SING N N 43 
385 N21 S24  SING N N 44 
385 N21 C25  SING N N 45 
385 C22 C26  SING Y N 46 
385 C22 H22  SING N N 47 
385 C23 C26  DOUB Y N 48 
385 C23 H23  SING N N 49 
385 S24 C27  SING N N 50 
385 S24 O28  DOUB N N 51 
385 S24 O29  DOUB N N 52 
385 C25 C30  SING N N 53 
385 C25 H251 SING N N 54 
385 C25 H252 SING N N 55 
385 C26 O31  SING N N 56 
385 C27 C32  DOUB Y N 57 
385 C27 C33  SING Y N 58 
385 C30 C34  SING N N 59 
385 C30 C35  SING N N 60 
385 C30 H30  SING N N 61 
385 O31 C36  SING N N 62 
385 C32 C37  SING Y N 63 
385 C32 H32  SING N N 64 
385 C33 C38  DOUB Y N 65 
385 C33 H33  SING N N 66 
385 C34 H341 SING N N 67 
385 C34 H342 SING N N 68 
385 C34 H343 SING N N 69 
385 C35 H351 SING N N 70 
385 C35 H352 SING N N 71 
385 C35 H353 SING N N 72 
385 C36 C39  SING N N 73 
385 C36 H361 SING N N 74 
385 C36 H362 SING N N 75 
385 C37 C40  DOUB Y N 76 
385 C37 O41  SING N N 77 
385 C38 C40  SING Y N 78 
385 C38 H38  SING N N 79 
385 C39 N42  SING Y N 80 
385 C39 C43  DOUB Y N 81 
385 C40 O44  SING N N 82 
385 O41 C45  SING N N 83 
385 N42 C46  DOUB Y N 84 
385 C43 S47  SING Y N 85 
385 C43 H43  SING N N 86 
385 O44 C45  SING N N 87 
385 C45 H451 SING N N 88 
385 C45 H452 SING N N 89 
385 C46 S47  SING Y N 90 
385 C46 C48  SING N N 91 
385 C48 H481 SING N N 92 
385 C48 H482 SING N N 93 
385 C48 H483 SING N N 94 
# 
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 
385 SMILES           ACDLabs              10.04 O=S(=O)(c2ccc1OCOc1c2)N(CC(C)C)CC(O)C(NC(=O)OC3C4CCOC4OC3)Cc6ccc(OCc5nc(sc5)C)cc6 
385 InChI            InChI                1.02b 
;InChI=1/C33H41N3O10S2/c1-20(2)14-36(48(39,40)25-8-9-29-30(13-25)45-19-44-29)15-28(37)27(35-33(38)46-31-17-43-32-26(31)10-11-41-32)12-22-4-6-24(7-5-22)42-16-23-18-47-21(3)34-23/h4-9,13,18,20,26-28,31-32,37H,10-12,14-17,19H2,1-3H3,(H,35,38)/t26-,27-,28+,31-,32+/m0/s1/f/h35H
;
385 InChIKey         InChI                1.02b JORVRJNILJXMMG-GFDBGLLFDN 
385 SMILES_CANONICAL CACTVS               3.341 CC(C)CN(C[C@@H](O)[C@H](Cc1ccc(OCc2csc(C)n2)cc1)NC(=O)O[C@H]3CO[C@H]4OCC[C@@H]34)[S](=O)(=O)c5ccc6OCOc6c5 
385 SMILES           CACTVS               3.341 CC(C)CN(C[CH](O)[CH](Cc1ccc(OCc2csc(C)n2)cc1)NC(=O)O[CH]3CO[CH]4OCC[CH]34)[S](=O)(=O)c5ccc6OCOc6c5 
385 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1nc(cs1)COc2ccc(cc2)C[C@@H]([C@@H](C[N@](CC(C)C)S(=O)(=O)c3ccc4c(c3)OCO4)O)NC(=O)O[C@H]5CO[C@@H]6[C@H]5CCO6 
385 SMILES           "OpenEye OEToolkits" 1.5.0 Cc1nc(cs1)COc2ccc(cc2)CC(C(CN(CC(C)C)S(=O)(=O)c3ccc4c(c3)OCO4)O)NC(=O)OC5COC6C5CCO6 
# 
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 
385 "SYSTEMATIC NAME" ACDLabs              10.04 "(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl [(1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-{4-[(2-methyl-1,3-thiazol-4-yl)methoxy]benzyl}propyl]carbamate" 
385 "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-(1,3-benzodioxol-5-ylsulfonyl-(2-methylpropyl)amino)-3-hydroxy-1-[4-[(2-methyl-1,3-thiazol-4-yl)methoxy]phenyl]butan-2-yl]carbamate" 
# 
