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 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 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 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" 385 InChI InChI 1.03 ;InChI=1S/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 ; 385 InChIKey InChI 1.03 JORVRJNILJXMMG-OLNQLETPSA-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 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" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 385 "Create component" 2006-01-23 RCSB 385 "Modify descriptor" 2011-06-04 RCSB #