data_BMH # _chem_comp.id BMH _chem_comp.name ;5H-PYRAZOLO(1,2-A)(1,2,4)TRIAZOL-4-IUM, 6-((2-CARBOXY-6-(1-HYDROXYETHYL)-4-METHYL-7-OXO-1-AZABICYCLO(3.2.0)HEPT-2-EN-3-YL)THIO)-6,7-DIHYDRO-, HYDROXIDE, INNER SALT, (4R-(4ALPHA,5BETA,6BETA(R*)))- ; _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C15 H22 N4 O5 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "BIAPENEM (HYDLYZED)" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2004-08-25 _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 370.424 _chem_comp.one_letter_code ? _chem_comp.three_letter_code BMH _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 Y _chem_comp.pdbx_model_coordinates_db_code 1X8I _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 BMH O71 O71 O 0 1 N N N 13.677 48.644 70.412 4.356 -1.605 1.597 O71 BMH 1 BMH C7 C7 C 0 1 N N N 14.830 49.020 70.589 3.582 -0.792 0.861 C7 BMH 2 BMH O72 O72 O 0 1 N N N 15.104 50.304 70.547 3.050 0.164 1.374 O72 BMH 3 BMH C6 C6 C 0 1 N N S 15.936 48.035 70.894 3.378 -1.071 -0.606 C6 BMH 4 BMH C61 C61 C 0 1 N N R 17.324 48.648 71.151 4.491 -0.401 -1.413 C61 BMH 5 BMH O62 O62 O 0 1 N N N 18.383 47.673 71.184 4.357 1.019 -1.322 O62 BMH 6 BMH C62 C62 C 0 1 N N N 17.457 49.370 72.484 4.389 -0.830 -2.878 C62 BMH 7 BMH C5 C5 C 0 1 N N S 16.016 46.937 69.823 2.022 -0.514 -1.047 C5 BMH 8 BMH N4 N4 N 0 1 N N N 17.038 46.021 70.350 1.883 0.890 -0.632 N4 BMH 9 BMH C3 C3 C 0 1 N N N 18.313 46.641 70.147 0.798 1.003 0.237 C3 BMH 10 BMH C31 C31 C 0 1 N N S 19.467 45.693 70.305 0.369 2.307 0.857 C31 BMH 11 BMH O31 O31 O -1 1 N N N 20.687 46.231 70.315 -0.088 3.194 -0.167 O31 BMH 12 BMH O32 O32 O 0 1 N N N 19.313 44.463 70.467 1.477 2.898 1.539 O32 BMH 13 BMH C1 C1 C 0 1 N N R 16.650 47.323 68.482 0.877 -1.240 -0.316 C1 BMH 14 BMH C11 C11 C 0 1 N N N 16.119 48.589 67.796 1.433 -2.303 0.633 C11 BMH 15 BMH C2 C2 C 0 1 N N N 18.167 47.291 68.746 0.185 -0.140 0.464 C2 BMH 16 BMH S21 S21 S 0 1 N N N 18.883 46.351 67.344 -1.217 -0.357 1.508 S21 BMH 17 BMH C22 C22 C 0 1 N N N 20.551 46.981 67.148 -2.465 -0.807 0.270 C22 BMH 18 BMH C23 C23 C 0 1 N N N 20.529 48.430 66.708 -3.769 -1.276 0.950 C23 BMH 19 BMH N24 N24 N 1 1 Y N N 21.145 48.443 65.386 -4.850 -0.782 0.086 N24 BMH 20 BMH C25 C25 C 0 1 Y N N 20.462 49.033 64.237 -6.135 -0.927 -0.197 C25 BMH 21 BMH N28 N28 N 0 1 Y N N 21.511 47.142 64.969 -4.361 0.216 -0.769 N28 BMH 22 BMH C27 C27 C 0 1 N N N 21.160 46.164 66.008 -2.931 0.438 -0.516 C27 BMH 23 BMH C29 C29 C 0 1 Y N N 21.055 47.036 63.586 -5.383 0.611 -1.514 C29 BMH 24 BMH N26 N26 N 0 1 Y N N 20.500 48.194 63.179 -6.449 -0.083 -1.163 N26 BMH 25 BMH H71 H71 H 0 1 N N N 13.479 47.715 70.442 4.487 -1.426 2.538 H71 BMH 26 BMH H6 H6 H 0 1 N N N 15.639 47.588 71.871 3.401 -2.147 -0.778 H6 BMH 27 BMH H61 H61 H 0 1 N N N 17.417 49.353 70.292 5.460 -0.701 -1.014 H61 BMH 28 BMH H62 H62 H 0 1 N N N 19.240 48.051 71.343 3.588 1.262 -1.855 H62 BMH 29 BMH H621 1H62 H 0 0 N N N 17.170 48.694 73.323 5.182 -0.352 -3.453 H621 BMH 30 BMH H622 2H62 H 0 0 N N N 18.463 49.814 72.670 4.491 -1.913 -2.948 H622 BMH 31 BMH H623 3H62 H 0 0 N N N 16.664 50.147 72.585 3.420 -0.530 -3.278 H623 BMH 32 BMH H5 H5 H 0 1 N N N 14.969 46.597 69.644 1.906 -0.606 -2.127 H5 BMH 33 BMH HN4 HN4 H 0 1 N N N 16.981 45.086 69.947 2.454 1.620 -0.916 HN4 BMH 34 BMH H31 H31 H 0 1 N N N 19.063 44.813 69.753 -0.439 2.125 1.566 H31 BMH 35 BMH H32 H32 H 0 1 N N N 20.043 43.863 70.567 ? ? ? H32 BMH 36 BMH H1 H1 H 0 1 N N N 16.353 46.595 67.692 0.189 -1.690 -1.032 H1 BMH 37 BMH H111 1H11 H 0 0 N N N 16.189 49.450 68.501 0.608 -2.860 1.078 H111 BMH 38 BMH H112 2H11 H 0 0 N N N 16.580 48.870 66.821 2.075 -2.986 0.078 H112 BMH 39 BMH H113 3H11 H 0 0 N N N 15.014 48.510 67.675 2.011 -1.820 1.421 H113 BMH 40 BMH H22 H22 H 0 1 N N N 21.116 46.907 68.107 -2.082 -1.573 -0.403 H22 BMH 41 BMH H231 1H23 H 0 0 N N N 21.009 49.127 67.434 -3.797 -2.364 1.007 H231 BMH 42 BMH H232 2H23 H 0 0 N N N 19.515 48.892 66.735 -3.854 -0.842 1.947 H232 BMH 43 BMH H25 H25 H 0 1 N N N 19.966 50.016 64.174 -6.813 -1.619 0.282 H25 BMH 44 BMH H271 1H27 H 0 0 N N N 20.502 45.341 65.645 -2.787 1.339 0.081 H271 BMH 45 BMH H272 2H27 H 0 0 N N N 22.013 45.520 66.324 -2.388 0.516 -1.458 H272 BMH 46 BMH H29 H29 H 0 1 N N N 21.123 46.165 62.913 -5.349 1.372 -2.279 H29 BMH 47 # # 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 BMH O71 C7 SING N N 1 BMH O71 H71 SING N N 2 BMH C7 O72 DOUB N N 3 BMH C7 C6 SING N N 4 BMH C6 C61 SING N N 5 BMH C6 C5 SING N N 6 BMH C6 H6 SING N N 7 BMH C61 O62 SING N N 8 BMH C61 C62 SING N N 9 BMH C61 H61 SING N N 10 BMH O62 H62 SING N N 11 BMH C62 H621 SING N N 12 BMH C62 H622 SING N N 13 BMH C62 H623 SING N N 14 BMH C5 N4 SING N N 15 BMH C5 C1 SING N N 16 BMH C5 H5 SING N N 17 BMH N4 C3 SING N N 18 BMH N4 HN4 SING N N 19 BMH C3 C31 SING N N 20 BMH C3 C2 DOUB N N 21 BMH C31 O31 SING N N 22 BMH C31 O32 SING N N 23 BMH C31 H31 SING N N 24 BMH O32 H32 SING N N 25 BMH C1 C11 SING N N 26 BMH C1 C2 SING N N 27 BMH C1 H1 SING N N 28 BMH C11 H111 SING N N 29 BMH C11 H112 SING N N 30 BMH C11 H113 SING N N 31 BMH C2 S21 SING N N 32 BMH S21 C22 SING N N 33 BMH C22 C23 SING N N 34 BMH C22 C27 SING N N 35 BMH C22 H22 SING N N 36 BMH C23 N24 SING N N 37 BMH C23 H231 SING N N 38 BMH C23 H232 SING N N 39 BMH N24 C25 DOUB Y N 40 BMH N24 N28 SING Y N 41 BMH C25 N26 SING Y N 42 BMH C25 H25 SING N N 43 BMH N28 C27 SING N N 44 BMH N28 C29 SING Y N 45 BMH C27 H271 SING N N 46 BMH C27 H272 SING N N 47 BMH C29 N26 DOUB Y N 48 BMH C29 H29 SING N N 49 # # 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 BMH SMILES ACDLabs 10.04 "O=C(O)C(C(O)C)C3NC(=C(SC2C[n+]1cncn1C2)C3C)C([O-])O" BMH SMILES_CANONICAL CACTVS 3.341 "C[C@@H](O)[C@H]([C@@H]1NC(=C(S[C@H]2Cn3cnc[n+]3C2)[C@@H]1C)[C@H](O)[O-])C(O)=O" BMH SMILES CACTVS 3.341 "C[CH](O)[CH]([CH]1NC(=C(S[CH]2Cn3cnc[n+]3C2)[CH]1C)[CH](O)[O-])C(O)=O" BMH SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C[C@@H]1[C@@H](NC(=C1S[C@H]2Cn3cnc[n+]3C2)C(O)[O-])[C@@H]([C@@H](C)O)C(=O)O" BMH SMILES "OpenEye OEToolkits" 1.5.0 "CC1C(NC(=C1SC2Cn3cnc[n+]3C2)C(O)[O-])C(C(C)O)C(=O)O" BMH InChI InChI 1.03 "InChI=1S/C15H22N4O5S/c1-7-11(10(8(2)20)14(21)22)17-12(15(23)24)13(7)25-9-3-18-5-16-6-19(18)4-9/h5-11,15,17,20,23H,3-4H2,1-2H3,(H,21,22)/t7-,8-,10-,11-,15-/m1/s1" BMH InChIKey InChI 1.03 GJACIOMQYIQIKX-FGOODDOWSA-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 BMH "SYSTEMATIC NAME" ACDLabs 10.04 "(S)-[(4R,5S)-5-[(1S,2R)-1-carboxy-2-hydroxypropyl]-3-(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazol-4-ium-6-ylsulfanyl)-4-methyl-4,5-dihydro-1H-pyrrol-2-yl](hydroxy)methanolate" BMH "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(4R,5S)-3-[[(6S)-6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazol-8-ium-6-yl]sulfanyl]-5-[(2S,3R)-1,3-dihydroxy-1-oxo-butan-2-yl]-4-methyl-4,5-dihydro-1H-pyrrol-2-yl]-hydroxy-methanolate" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site BMH "Create component" 2004-08-25 RCSB BMH "Modify descriptor" 2011-06-04 RCSB BMH "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id BMH _pdbx_chem_comp_synonyms.name "BIAPENEM (HYDLYZED)" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##