data_SN3 # _chem_comp.id SN3 _chem_comp.name ;(R)-3-((2S,3R)-1-((2S,3AR,5S,6S,7AS)-2-(2-(1-CARBAMIMIDOYL-2,5-DIHYDRO-1H-PYRROL-3-YL)ETHYLCARBAMOYL)-5,6-DIHYDROXYOCTA HYDRO-1H-INDOL-1-YL)-3-CHLORO-4-METHYL-1-OXOPENTAN-2-YLAMINO)-2-METHOXY-3-OXOPROPYL HYDROGEN SULFATE ; _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C26 H43 Cl N6 O10 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms CHLORODYSINOSIN _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2006-03-29 _chem_comp.pdbx_modified_date 2020-06-17 _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 667.172 _chem_comp.one_letter_code ? _chem_comp.three_letter_code SN3 _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 2GDE _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 SN3 C1 C1 C 0 1 N N S 20.655 -15.222 18.446 0.301 2.977 -2.658 C1 SN3 1 SN3 C2 C2 C 0 1 N N N 21.176 -14.095 19.376 -0.705 3.402 -1.591 C2 SN3 2 SN3 C3 C3 C 0 1 N N R 20.219 -13.557 20.437 -0.038 4.299 -0.547 C3 SN3 3 SN3 C4 C4 C 0 1 N N S 19.184 -14.565 20.969 1.197 3.604 0.055 C4 SN3 4 SN3 C5 C5 C 0 1 N N N 18.611 -15.545 19.914 2.143 3.068 -0.995 C5 SN3 5 SN3 C6 C6 C 0 1 N N S 19.753 -16.255 19.181 1.413 2.163 -1.988 C6 SN3 6 SN3 O7 O7 O 0 1 N N N 20.482 -17.049 20.139 2.331 1.696 -2.978 O7 SN3 7 SN3 N8 N8 N 0 1 N N N 18.155 -13.668 21.558 0.671 2.559 0.938 N8 SN3 8 SN3 C9 C9 C 0 1 N N S 18.190 -12.379 20.864 -0.674 2.971 1.378 C9 SN3 9 SN3 C10 C10 C 0 1 N N N 19.318 -12.473 19.817 -0.985 4.320 0.692 C10 SN3 10 SN3 C11 C11 C 0 1 N N N 16.878 -12.130 20.153 -1.689 1.938 0.962 C11 SN3 11 SN3 N12 N12 N 0 1 N N N 16.365 -10.872 20.154 -2.998 2.140 1.212 N12 SN3 12 SN3 C13 C13 C 0 1 N N N 15.098 -10.602 19.449 -3.973 1.089 0.908 C13 SN3 13 SN3 C14 C14 C 0 1 N N N 14.281 -9.611 20.270 -5.357 1.520 1.398 C14 SN3 14 SN3 C15 C15 C 0 1 N N N 13.558 -10.383 21.348 -6.359 0.439 1.084 C15 SN3 15 SN3 C16 C16 C 0 1 N N N 12.961 -9.731 22.550 -7.078 0.285 -0.230 C16 SN3 16 SN3 N17 N17 N 0 1 N N N 12.209 -10.755 23.271 -7.956 -0.888 -0.108 N17 SN3 17 SN3 C18 C18 C 0 1 N N N 12.607 -12.034 22.670 -7.744 -1.398 1.254 C18 SN3 18 SN3 C19 C19 C 0 1 N N N 13.388 -11.683 21.422 -6.726 -0.502 1.909 C19 SN3 19 SN3 C20 C20 C 0 1 N N N 11.347 -10.539 24.238 -8.799 -1.400 -1.066 C20 SN3 20 SN3 N21 N21 N 0 1 N N N 10.664 -11.592 24.821 -8.878 -0.830 -2.236 N21 SN3 21 SN3 N22 N22 N 0 1 N N N 11.086 -9.263 24.653 -9.559 -2.512 -0.790 N22 SN3 22 SN3 O23 O23 O 0 1 N N N 16.305 -13.056 19.582 -1.328 0.925 0.401 O23 SN3 23 SN3 C24 C24 C 0 1 N N N 17.332 -13.971 22.580 1.305 1.422 1.287 C24 SN3 24 SN3 O25 O25 O 0 1 N N N 16.560 -13.112 22.946 0.834 0.703 2.142 O25 SN3 25 SN3 C26 C26 C 0 1 N N S 17.366 -15.327 23.271 2.599 1.044 0.613 C26 SN3 26 SN3 C27 C27 C 0 1 N N R 17.745 -15.115 24.750 3.745 1.857 1.218 C27 SN3 27 SN3 C28 C28 C 0 1 N N N 17.741 -16.408 25.571 5.024 1.612 0.414 C28 SN3 28 SN3 C29 C29 C 0 1 N N N 18.658 -17.501 24.992 4.845 2.154 -1.006 C29 SN3 29 SN3 C30 C30 C 0 1 N N N 18.158 -16.049 26.995 6.195 2.329 1.089 C30 SN3 30 SN3 CL31 CL31 CL 0 0 N N N 19.334 -14.269 24.819 3.330 3.611 1.169 CL31 SN3 31 SN3 N32 N32 N 0 1 N N N 16.043 -15.948 23.241 2.854 -0.384 0.812 N32 SN3 32 SN3 C33 C33 C 0 1 N N N 15.769 -17.033 22.477 3.624 -1.060 -0.064 C33 SN3 33 SN3 C34 C34 C 0 1 N N R 14.389 -17.615 22.522 3.887 -2.530 0.142 C34 SN3 34 SN3 O35 O35 O 0 1 N N N 13.451 -16.603 22.925 4.815 -2.990 -0.843 O35 SN3 35 SN3 C36 C36 C 0 1 N N N 12.928 -15.839 21.824 5.637 -4.073 -0.405 C36 SN3 36 SN3 C37 C37 C 0 1 N N N 14.411 -18.827 23.471 2.575 -3.306 0.008 C37 SN3 37 SN3 O38 O38 O 0 1 N N N 14.486 -18.467 24.862 2.803 -4.682 0.317 O38 SN3 38 SN3 S39 S39 S 0 1 N N N 15.053 -19.563 25.796 1.559 -5.553 0.215 S39 SN3 39 SN3 O40 O40 O 0 1 N N N 15.221 -19.010 27.092 1.277 -5.766 -1.265 O40 SN3 40 SN3 O41 O41 O 0 1 N N N 13.975 -20.620 26.032 1.914 -6.824 0.742 O41 SN3 41 SN3 O42 O42 O 0 1 N N N 16.113 -20.172 25.054 0.482 -4.776 0.721 O42 SN3 42 SN3 O43 O43 O 0 1 N N N 16.601 -17.548 21.750 4.105 -0.485 -1.017 O43 SN3 43 SN3 O46 O46 O 0 1 N N N 19.994 -14.632 17.310 -0.354 2.173 -3.642 O46 SN3 44 SN3 H1 H1 H 0 1 N N N 21.521 -15.804 18.097 0.729 3.861 -3.131 H1 SN3 45 SN3 H21 H21 H 0 1 N N N 22.049 -14.499 19.909 -1.521 3.947 -2.065 H21 SN3 46 SN3 H22 H22 H 0 1 N N N 21.446 -13.247 18.730 -1.104 2.515 -1.100 H22 SN3 47 SN3 H3 H3 H 0 1 N N N 20.894 -13.232 21.242 0.189 5.292 -0.936 H3 SN3 48 SN3 H4 H4 H 0 1 N N N 19.626 -15.275 21.684 1.734 4.325 0.671 H4 SN3 49 SN3 H51 H51 H 0 1 N N N 17.982 -16.294 20.418 2.588 3.904 -1.535 H51 SN3 50 SN3 H52 H52 H 0 1 N N N 18.007 -14.983 19.187 2.933 2.498 -0.507 H52 SN3 51 SN3 H6 H6 H 0 1 N N N 19.359 -16.925 18.403 0.979 1.314 -1.460 H6 SN3 52 SN3 HO7 HO7 H 0 1 N N N 19.890 -17.662 20.559 1.930 1.128 -3.650 HO7 SN3 53 SN3 H9 H9 H 0 1 N N N 18.359 -11.559 21.577 -0.689 3.094 2.461 H9 SN3 54 SN3 H101 H101 H 0 0 N N N 19.846 -11.517 19.686 -0.742 5.154 1.350 H101 SN3 55 SN3 H102 H102 H 0 0 N N N 18.942 -12.761 18.824 -2.029 4.364 0.380 H102 SN3 56 SN3 HN12 HN12 H 0 0 N N N 16.843 -10.134 20.630 -3.295 2.980 1.594 HN12 SN3 57 SN3 H131 H131 H 0 0 N N N 15.309 -10.176 18.457 -4.004 0.924 -0.169 H131 SN3 58 SN3 H132 H132 H 0 0 N N N 14.533 -11.538 19.329 -3.680 0.166 1.408 H132 SN3 59 SN3 H141 H141 H 0 0 N N N 14.946 -8.862 20.726 -5.325 1.685 2.475 H141 SN3 60 SN3 H142 H142 H 0 0 N N N 13.554 -9.097 19.624 -5.649 2.443 0.897 H142 SN3 61 SN3 H161 H161 H 0 0 N N N 13.754 -9.319 23.192 -7.674 1.174 -0.433 H161 SN3 62 SN3 H162 H162 H 0 0 N N N 12.292 -8.912 22.245 -6.357 0.126 -1.031 H162 SN3 63 SN3 H181 H181 H 0 0 N N N 13.230 -12.613 23.367 -8.680 -1.370 1.811 H181 SN3 64 SN3 H182 H182 H 0 0 N N N 11.722 -12.636 22.417 -7.363 -2.418 1.213 H182 SN3 65 SN3 H192 H192 H 0 0 N N N 13.752 -12.397 20.698 -6.355 -0.620 2.917 H192 SN3 66 SN3 HN21 HN21 H 0 0 N N N 10.020 -11.280 25.520 -9.473 -1.191 -2.911 HN21 SN3 67 SN3 H221 H221 H 0 0 N N N 10.408 -9.099 25.370 -9.500 -2.935 0.081 H221 SN3 68 SN3 H222 H222 H 0 0 N N N 11.573 -8.493 24.240 -10.154 -2.873 -1.465 H222 SN3 69 SN3 H26 H26 H 0 1 N N N 18.093 -15.971 22.754 2.528 1.255 -0.454 H26 SN3 70 SN3 H27 H27 H 0 1 N N N 16.972 -14.490 25.220 3.902 1.550 2.252 H27 SN3 71 SN3 H28 H28 H 0 1 N N N 16.729 -16.837 25.547 5.227 0.542 0.372 H28 SN3 72 SN3 H291 H291 H 0 0 N N N 18.607 -18.397 25.627 4.010 1.643 -1.486 H291 SN3 73 SN3 H292 H292 H 0 0 N N N 18.328 -17.755 23.974 4.641 3.224 -0.964 H292 SN3 74 SN3 H293 H293 H 0 0 N N N 19.694 -17.132 24.961 5.756 1.979 -1.578 H293 SN3 75 SN3 H301 H301 H 0 0 N N N 18.166 -16.957 27.615 6.379 1.883 2.067 H301 SN3 76 SN3 H302 H302 H 0 0 N N N 19.165 -15.606 26.981 7.088 2.228 0.471 H302 SN3 77 SN3 H303 H303 H 0 0 N N N 17.444 -15.325 27.415 5.955 3.385 1.210 H303 SN3 78 SN3 HN32 HN32 H 0 0 N N N 15.314 -15.558 23.804 2.470 -0.844 1.575 HN32 SN3 79 SN3 H34 H34 H 0 1 N N N 14.065 -17.964 21.530 4.303 -2.689 1.136 H34 SN3 80 SN3 H361 H361 H 0 0 N N N 12.220 -15.087 22.202 6.218 -3.761 0.463 H361 SN3 81 SN3 H362 H362 H 0 0 N N N 13.755 -15.335 21.302 5.008 -4.921 -0.135 H362 SN3 82 SN3 H363 H363 H 0 0 N N N 12.409 -16.511 21.125 6.314 -4.364 -1.208 H363 SN3 83 SN3 H371 H371 H 0 0 N N N 13.485 -19.401 23.315 1.838 -2.895 0.698 H371 SN3 84 SN3 H372 H372 H 0 0 N N N 15.294 -19.437 23.227 2.204 -3.219 -1.013 H372 SN3 85 SN3 HO40 HO40 H 0 0 N N N 14.635 -19.445 27.701 0.498 -6.311 -1.443 HO40 SN3 86 SN3 HO46 HO46 H 0 0 N N N 19.673 -15.319 16.738 0.228 1.868 -4.352 HO46 SN3 87 # # 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 SN3 C1 C2 SING N N 1 SN3 C1 C6 SING N N 2 SN3 C1 O46 SING N N 3 SN3 C1 H1 SING N N 4 SN3 C2 C3 SING N N 5 SN3 C2 H21 SING N N 6 SN3 C2 H22 SING N N 7 SN3 C3 C4 SING N N 8 SN3 C3 C10 SING N N 9 SN3 C3 H3 SING N N 10 SN3 C4 C5 SING N N 11 SN3 C4 N8 SING N N 12 SN3 C4 H4 SING N N 13 SN3 C5 C6 SING N N 14 SN3 C5 H51 SING N N 15 SN3 C5 H52 SING N N 16 SN3 C6 O7 SING N N 17 SN3 C6 H6 SING N N 18 SN3 O7 HO7 SING N N 19 SN3 N8 C9 SING N N 20 SN3 N8 C24 SING N N 21 SN3 C9 C10 SING N N 22 SN3 C9 C11 SING N N 23 SN3 C9 H9 SING N N 24 SN3 C10 H101 SING N N 25 SN3 C10 H102 SING N N 26 SN3 C11 N12 SING N N 27 SN3 C11 O23 DOUB N N 28 SN3 N12 C13 SING N N 29 SN3 N12 HN12 SING N N 30 SN3 C13 C14 SING N N 31 SN3 C13 H131 SING N N 32 SN3 C13 H132 SING N N 33 SN3 C14 C15 SING N N 34 SN3 C14 H141 SING N N 35 SN3 C14 H142 SING N N 36 SN3 C15 C16 SING N N 37 SN3 C15 C19 DOUB N N 38 SN3 C16 N17 SING N N 39 SN3 C16 H161 SING N N 40 SN3 C16 H162 SING N N 41 SN3 N17 C18 SING N N 42 SN3 N17 C20 SING N N 43 SN3 C18 C19 SING N N 44 SN3 C18 H181 SING N N 45 SN3 C18 H182 SING N N 46 SN3 C19 H192 SING N N 47 SN3 C20 N21 DOUB N N 48 SN3 C20 N22 SING N N 49 SN3 N21 HN21 SING N N 50 SN3 N22 H221 SING N N 51 SN3 N22 H222 SING N N 52 SN3 C24 O25 DOUB N N 53 SN3 C24 C26 SING N N 54 SN3 C26 C27 SING N N 55 SN3 C26 N32 SING N N 56 SN3 C26 H26 SING N N 57 SN3 C27 C28 SING N N 58 SN3 C27 CL31 SING N N 59 SN3 C27 H27 SING N N 60 SN3 C28 C29 SING N N 61 SN3 C28 C30 SING N N 62 SN3 C28 H28 SING N N 63 SN3 C29 H291 SING N N 64 SN3 C29 H292 SING N N 65 SN3 C29 H293 SING N N 66 SN3 C30 H301 SING N N 67 SN3 C30 H302 SING N N 68 SN3 C30 H303 SING N N 69 SN3 N32 C33 SING N N 70 SN3 N32 HN32 SING N N 71 SN3 C33 C34 SING N N 72 SN3 C33 O43 DOUB N N 73 SN3 C34 O35 SING N N 74 SN3 C34 C37 SING N N 75 SN3 C34 H34 SING N N 76 SN3 O35 C36 SING N N 77 SN3 C36 H361 SING N N 78 SN3 C36 H362 SING N N 79 SN3 C36 H363 SING N N 80 SN3 C37 O38 SING N N 81 SN3 C37 H371 SING N N 82 SN3 C37 H372 SING N N 83 SN3 O38 S39 SING N N 84 SN3 S39 O40 SING N N 85 SN3 S39 O41 DOUB N N 86 SN3 S39 O42 DOUB N N 87 SN3 O40 HO40 SING N N 88 SN3 O46 HO46 SING N N 89 # # 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 SN3 SMILES ACDLabs 12.01 "O=S(=O)(O)OCC(OC)C(=O)NC(C(=O)N2C(C(=O)NCCC1=CCN(C(=[N@H])N)C1)CC3CC(O)C(O)CC23)C(Cl)C(C)C" SN3 SMILES_CANONICAL CACTVS 3.370 "CO[C@H](CO[S](O)(=O)=O)C(=O)N[C@H]([C@H](Cl)C(C)C)C(=O)N1[C@H]2C[C@H](O)[C@@H](O)C[C@H]2C[C@H]1C(=O)NCCC3=CCN(C3)C(N)=N" SN3 SMILES CACTVS 3.370 "CO[CH](CO[S](O)(=O)=O)C(=O)N[CH]([CH](Cl)C(C)C)C(=O)N1[CH]2C[CH](O)[CH](O)C[CH]2C[CH]1C(=O)NCCC3=CCN(C3)C(N)=N" SN3 SMILES_CANONICAL "OpenEye OEToolkits" 1.7.0 "[H]/N=C(\N)/N1CC=C(C1)CCNC(=O)[C@@H]2C[C@@H]3C[C@@H]([C@H](C[C@@H]3N2C(=O)[C@@H]([C@@H](C(C)C)Cl)NC(=O)[C@@H](COS(=O)(=O)O)OC)O)O" SN3 SMILES "OpenEye OEToolkits" 1.7.0 "CC(C)C(C(C(=O)N1C2CC(C(CC2CC1C(=O)NCCC3=CCN(C3)C(=N)N)O)O)NC(=O)C(COS(=O)(=O)O)OC)Cl" SN3 InChI InChI 1.03 "InChI=1S/C26H43ClN6O10S/c1-13(2)21(27)22(31-24(37)20(42-3)12-43-44(39,40)41)25(38)33-16-10-19(35)18(34)9-15(16)8-17(33)23(36)30-6-4-14-5-7-32(11-14)26(28)29/h5,13,15-22,34-35H,4,6-12H2,1-3H3,(H3,28,29)(H,30,36)(H,31,37)(H,39,40,41)/t15-,16+,17+,18+,19+,20-,21-,22-/m1/s1" SN3 InChIKey InChI 1.03 BVKDJAALSHFQTE-WNZJUFNWSA-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 SN3 "SYSTEMATIC NAME" ACDLabs 12.01 "(2R)-3-({(2S,3R)-1-[(2S,3aR,5S,6S,7aS)-2-{[2-(1-carbamimidoyl-2,5-dihydro-1H-pyrrol-3-yl)ethyl]carbamoyl}-5,6-dihydroxyoctahydro-1H-indol-1-yl]-3-chloro-4-methyl-1-oxopentan-2-yl}amino)-2-methoxy-3-oxopropyl hydrogen sulfate (non-preferred name)" SN3 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.0 "[(2R)-3-[[(2S,3R)-1-[(2S,3aR,5S,6S,7aS)-2-[2-(1-carbamimidoyl-2,5-dihydropyrrol-3-yl)ethylcarbamoyl]-5,6-dihydroxy-2,3,3a,4,5,6,7,7a-octahydroindol-1-yl]-3-chloro-4-methyl-1-oxo-pentan-2-yl]amino]-2-methoxy-3-oxo-propyl] hydrogen sulfate" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site SN3 "Create component" 2006-03-29 RCSB SN3 "Other modification" 2010-10-11 RCSB SN3 "Modify descriptor" 2011-06-04 RCSB SN3 "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id SN3 _pdbx_chem_comp_synonyms.name CHLORODYSINOSIN _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##