data_DRW # _chem_comp.id DRW _chem_comp.name "(2S,3R,4S)-2-[(2S,3R)-3-hydroxy-1-oxobutan-2-yl]-3-methyl-4-({(3S,5S)-5-[(sulfamoylamino)methyl]pyrrolidin-3-yl}sulfanyl)-3,4-dihydro-2H-pyrrole-5-carboxylic acid" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAD _chem_comp.formula "C15 H26 N4 O6 S2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "Doripenem(open form, pyrroline tautomer form 2, SP3 connection to Thio as S isomer)" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2009-08-24 _chem_comp.pdbx_modified_date 2021-03-13 _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 422.520 _chem_comp.one_letter_code ? _chem_comp.three_letter_code DRW _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 3IQA _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 DRW CAA CAA C 0 1 N N N -8.776 -13.757 4.772 -5.965 -1.439 2.437 CAA DRW 1 DRW CAB CAB C 0 1 N N N -8.889 -11.106 2.422 -3.734 -1.441 -2.035 CAB DRW 2 DRW NAC NAC N 0 1 N N N -4.551 -5.986 -2.641 7.231 -1.846 0.180 NAC DRW 3 DRW OAD OAD O 0 1 N N N -12.526 -10.757 4.370 -6.238 -0.649 -2.134 OAD DRW 4 DRW OAE OAE O 0 1 N N N -11.182 -7.198 5.091 -2.527 3.274 0.328 OAE DRW 5 DRW OAF OAF O 0 1 N N N -5.185 -4.231 -0.850 7.269 0.283 1.428 OAF DRW 6 DRW OAG OAG O 0 1 N N N -3.035 -4.175 -1.942 7.870 0.227 -0.997 OAG DRW 7 DRW OAH OAH O 0 1 N N N -9.998 -6.378 3.628 -0.832 2.372 -0.783 OAH DRW 8 DRW OAI OAI O 0 1 N N N -10.108 -13.266 6.581 -6.041 0.798 1.525 OAI DRW 9 DRW CAJ CAJ C 0 1 N N N -11.739 -11.172 5.154 -5.725 -0.151 -1.161 CAJ DRW 10 DRW CAK CAK C 0 1 N N N -6.224 -5.958 3.494 1.279 0.390 -1.225 CAK DRW 11 DRW CAL CAL C 0 1 N N N -4.633 -6.912 0.288 4.428 -0.222 0.633 CAL DRW 12 DRW CAM CAM C 0 1 N N N -5.506 -7.954 2.381 1.955 0.055 1.107 CAM DRW 13 DRW NAN NAN N 0 1 N N N -9.824 -9.476 5.166 -3.592 0.605 0.468 NAN DRW 14 DRW NAO NAO N 0 1 N N N -6.028 -5.804 2.073 2.727 0.099 -1.143 NAO DRW 15 DRW NAP NAP N 0 1 N N N -3.543 -6.003 -0.188 5.507 0.132 -0.293 NAP DRW 16 DRW SAQ SAQ S 0 1 N N N -6.911 -8.350 4.738 -0.506 -0.965 0.381 SAQ DRW 17 DRW CAR CAR C 0 1 N N N -10.265 -7.252 4.358 -1.892 2.217 -0.212 CAR DRW 18 DRW CAS CAS C 0 1 N N N -9.533 -8.562 4.333 -2.487 0.863 -0.110 CAS DRW 19 DRW CAT CAT C 0 1 N N R -10.078 -13.187 5.204 -6.289 -0.575 1.217 CAT DRW 20 DRW CAU CAU C 0 1 N N R -8.342 -10.482 3.637 -3.022 -1.415 -0.681 CAU DRW 21 DRW CAV CAV C 0 1 N N S -4.954 -6.741 1.781 3.145 0.505 0.223 CAV DRW 22 DRW CAW CAW C 0 1 N N S -5.806 -7.381 3.726 0.729 0.353 0.213 CAW DRW 23 DRW CAX CAX C 0 1 N N S -10.368 -11.761 4.670 -5.406 -1.002 0.042 CAX DRW 24 DRW CAY CAY C 0 1 N N S -9.236 -10.730 4.866 -3.934 -0.821 0.418 CAY DRW 25 DRW CAZ CAZ C 0 1 N N S -8.222 -8.932 3.594 -1.862 -0.391 -0.680 CAZ DRW 26 DRW SBA SBA S 0 1 N N N -4.071 -5.076 -1.411 7.080 -0.199 0.105 SBA DRW 27 DRW HAA HAA H 0 1 N N N -8.703 -13.717 3.675 -6.594 -1.135 3.274 HAA DRW 28 DRW HAAA HAAA H 0 0 N N N -7.955 -13.174 5.216 -6.155 -2.486 2.202 HAAA DRW 29 DRW HAAB HAAB H 0 0 N N N -8.705 -14.803 5.106 -4.917 -1.310 2.705 HAAB DRW 30 DRW HAB HAB H 0 1 N N N -8.220 -10.904 1.572 -3.981 -0.422 -2.335 HAB DRW 31 DRW HABA HABA H 0 0 N N N -8.971 -12.192 2.573 -3.080 -1.891 -2.781 HABA DRW 32 DRW HABB HABB H 0 0 N N N -9.885 -10.689 2.212 -4.650 -2.027 -1.953 HABB DRW 33 DRW HNAC HNAC H 0 0 N N N -5.260 -6.620 -2.331 7.074 -2.309 1.018 HNAC DRW 34 DRW HNAA HNAA H 0 0 N N N -4.920 -5.402 -3.364 7.478 -2.347 -0.613 HNAA DRW 35 DRW HOAE HOAE H 0 0 N N N -11.628 -6.367 4.980 -2.100 4.137 0.236 HOAE DRW 36 DRW HOAI HOAI H 0 0 N N N -10.929 -12.910 6.901 -6.567 1.137 2.262 HOAI DRW 37 DRW HAJ HAJ H 0 1 N N N -11.968 -11.144 6.209 -5.495 0.904 -1.152 HAJ DRW 38 DRW HAK HAK H 0 1 N N N -7.278 -5.803 3.769 1.123 1.379 -1.656 HAK DRW 39 DRW HAKA HAKA H 0 0 N N N -5.590 -5.260 4.061 0.779 -0.363 -1.833 HAKA DRW 40 DRW HAL HAL H 0 1 N N N -4.321 -7.953 0.114 4.261 -1.298 0.602 HAL DRW 41 DRW HALA HALA H 0 0 N N N -5.543 -6.700 -0.292 4.705 0.074 1.645 HALA DRW 42 DRW HAM HAM H 0 1 N N N -4.771 -8.771 2.428 2.021 -1.010 1.329 HAM DRW 43 DRW HAMA HAMA H 0 0 N N N -6.411 -8.304 1.863 1.913 0.638 2.027 HAMA DRW 44 DRW HNAO HNAO H 0 0 N N N -6.858 -6.042 1.569 2.908 -0.881 -1.301 HNAO DRW 45 DRW HNAP HNAP H 0 0 N N N -3.250 -5.416 0.567 5.300 0.559 -1.138 HNAP DRW 46 DRW HAT HAT H 0 1 N N N -10.867 -13.837 4.799 -7.338 -0.703 0.948 HAT DRW 47 DRW HAU HAU H 0 1 N N N -7.345 -10.899 3.843 -2.671 -2.409 -0.406 HAU DRW 48 DRW HAV HAV H 0 1 N N N -4.038 -6.443 2.312 3.281 1.585 0.281 HAV DRW 49 DRW HAW HAW H 0 1 N N N -4.863 -7.357 4.292 0.294 1.316 0.477 HAW DRW 50 DRW HAX HAX H 0 1 N N N -10.473 -11.875 3.581 -5.596 -2.049 -0.193 HAX DRW 51 DRW HAY HAY H 0 1 N N N -8.601 -11.062 5.700 -3.729 -1.296 1.378 HAY DRW 52 DRW HAZ HAZ H 0 1 N N N -8.103 -8.495 2.592 -1.503 -0.213 -1.694 HAZ DRW 53 # # 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 DRW CAA CAT SING N N 1 DRW CAA HAA SING N N 2 DRW CAA HAAA SING N N 3 DRW CAA HAAB SING N N 4 DRW CAB CAU SING N N 5 DRW CAB HAB SING N N 6 DRW CAB HABA SING N N 7 DRW CAB HABB SING N N 8 DRW NAC SBA SING N N 9 DRW NAC HNAC SING N N 10 DRW NAC HNAA SING N N 11 DRW OAD CAJ DOUB N N 12 DRW OAE HOAE SING N N 13 DRW OAG SBA DOUB N N 14 DRW OAH CAR DOUB N N 15 DRW OAI HOAI SING N N 16 DRW CAJ HAJ SING N N 17 DRW CAK CAW SING N N 18 DRW CAK HAK SING N N 19 DRW CAK HAKA SING N N 20 DRW CAL CAV SING N N 21 DRW CAL HAL SING N N 22 DRW CAL HALA SING N N 23 DRW CAM CAW SING N N 24 DRW CAM HAM SING N N 25 DRW CAM HAMA SING N N 26 DRW NAO CAK SING N N 27 DRW NAO HNAO SING N N 28 DRW NAP CAL SING N N 29 DRW NAP HNAP SING N N 30 DRW CAR OAE SING N N 31 DRW CAS NAN DOUB N N 32 DRW CAS CAR SING N N 33 DRW CAT OAI SING N N 34 DRW CAT HAT SING N N 35 DRW CAU CAY SING N N 36 DRW CAU HAU SING N N 37 DRW CAV CAM SING N N 38 DRW CAV NAO SING N N 39 DRW CAV HAV SING N N 40 DRW CAW SAQ SING N N 41 DRW CAW HAW SING N N 42 DRW CAX CAJ SING N N 43 DRW CAX CAT SING N N 44 DRW CAX CAY SING N N 45 DRW CAX HAX SING N N 46 DRW CAY NAN SING N N 47 DRW CAY HAY SING N N 48 DRW CAZ SAQ SING N N 49 DRW CAZ CAS SING N N 50 DRW CAZ CAU SING N N 51 DRW CAZ HAZ SING N N 52 DRW SBA OAF DOUB N N 53 DRW SBA NAP SING N N 54 # # 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 DRW SMILES ACDLabs 12.01 "CC(O)C(C=O)C2N=C(C(O)=O)C(SC1CNC(CNS(N)(=O)=O)C1)C2C" DRW InChI InChI 1.03 "InChI=1S/C15H26N4O6S2/c1-7-12(11(6-20)8(2)21)19-13(15(22)23)14(7)26-10-3-9(17-5-10)4-18-27(16,24)25/h6-12,14,17-18,21H,3-5H2,1-2H3,(H,22,23)(H2,16,24,25)/t7-,8-,9+,10+,11-,12-,14+/m1/s1" DRW InChIKey InChI 1.03 RBKUPZPTQNSPAV-CFINEGTKSA-N DRW SMILES_CANONICAL CACTVS 3.385 "C[C@@H](O)[C@@H](C=O)[C@@H]1N=C([C@@H](S[C@@H]2CN[C@H](CN[S](N)(=O)=O)C2)[C@@H]1C)C(O)=O" DRW SMILES CACTVS 3.385 "C[CH](O)[CH](C=O)[CH]1N=C([CH](S[CH]2CN[CH](CN[S](N)(=O)=O)C2)[CH]1C)C(O)=O" DRW SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "C[C@H]1[C@@H](C(=N[C@H]1[C@H](C=O)[C@@H](C)O)C(=O)O)S[C@H]2C[C@H](NC2)CNS(=O)(=O)N" DRW SMILES "OpenEye OEToolkits" 1.7.6 "CC1C(C(=NC1C(C=O)C(C)O)C(=O)O)SC2CC(NC2)CNS(=O)(=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 DRW "SYSTEMATIC NAME" ACDLabs 12.01 "(2S,3R,4S)-2-[(2S,3R)-3-hydroxy-1-oxobutan-2-yl]-3-methyl-4-({(3S,5S)-5-[(sulfamoylamino)methyl]pyrrolidin-3-yl}sulfanyl)-3,4-dihydro-2H-pyrrole-5-carboxylic acid" DRW "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "(2S,3R,4S)-3-methyl-2-[(2S,3R)-3-oxidanyl-1-oxidanylidene-butan-2-yl]-4-[(3S,5S)-5-[(sulfamoylamino)methyl]pyrrolidin-3-yl]sulfanyl-3,4-dihydro-2H-pyrrole-5-carboxylic acid" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site DRW "Create component" 2009-08-24 RCSB DRW "Other modification" 2010-12-21 RCSB DRW "Modify descriptor" 2011-06-04 RCSB DRW "Modify synonyms" 2016-09-19 RCSB DRW "Modify synonyms" 2021-03-13 RCSB # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id DRW _pdbx_chem_comp_synonyms.name "Doripenem(open form, pyrroline tautomer form 2, SP3 connection to Thio as S isomer)" _pdbx_chem_comp_synonyms.provenance PDB _pdbx_chem_comp_synonyms.type ? ##