data_SMX # _chem_comp.id SMX _chem_comp.name "(6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C18 H18 N6 O5 S2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "CEFAMANDOLE, free form" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2010-09-17 _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 462.503 _chem_comp.one_letter_code ? _chem_comp.three_letter_code SMX _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 3NY4 _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 SMX C C C 0 1 N N N 0.128 -6.873 -4.316 1.067 2.297 -0.512 C SMX 1 SMX N N N 0 1 N N N -1.639 -7.015 -6.018 2.981 0.757 -0.112 N SMX 2 SMX O O O 0 1 N N N 0.938 -7.738 -4.407 1.090 3.426 -0.069 O SMX 3 SMX CA CA C 0 1 N N R -0.733 -6.105 -5.297 2.115 1.397 -1.105 CA SMX 4 SMX CB CB C 0 1 N N R -1.299 -5.493 -3.995 0.943 0.545 -1.538 CB SMX 5 SMX NBD NBD N 0 1 N N N -0.411 -6.385 -3.243 0.108 1.392 -0.651 NBD SMX 6 SMX NBE NBE N 0 1 Y N N 1.412 -3.977 0.587 -6.882 -1.052 -0.264 NBE SMX 7 SMX NAN NAN N 0 1 Y N N 1.527 -3.098 -1.197 -6.873 -1.084 1.901 NAN SMX 8 SMX NAO NAO N 0 1 Y N N 0.328 -3.154 -1.004 -5.670 -0.878 1.500 NAO SMX 9 SMX NAP NAP N 0 1 Y N N 2.156 -3.556 -0.252 -7.668 -1.198 0.892 NAP SMX 10 SMX CAA CAA C 0 1 N N N 1.757 -4.566 1.828 -7.331 -1.103 -1.658 CAA SMX 11 SMX OAB OAB O 0 1 N N N 1.831 -6.911 -1.549 -2.753 2.773 -0.302 OAB SMX 12 SMX OAC OAC O 0 1 N N N -1.942 -5.549 -7.697 4.657 2.130 -0.589 OAC SMX 13 SMX OAE OAE O 0 1 N N N 0.486 -7.958 -0.209 -1.967 2.428 1.745 OAE SMX 14 SMX OAF OAF O 0 1 N N N -3.600 -8.663 -7.606 6.365 1.259 1.180 OAF SMX 15 SMX CAG CAG C 0 1 Y N N -1.839 -8.188 -11.911 5.905 -3.490 -0.083 CAG SMX 16 SMX CAH CAH C 0 1 Y N N -3.057 -7.625 -11.628 4.878 -3.212 0.799 CAH SMX 17 SMX CAI CAI C 0 1 Y N N -0.967 -8.572 -10.890 6.684 -2.463 -0.583 CAI SMX 18 SMX CAJ CAJ C 0 1 Y N N -3.432 -7.453 -10.332 4.628 -1.907 1.179 CAJ SMX 19 SMX CAK CAK C 0 1 Y N N -1.343 -8.404 -9.582 6.433 -1.158 -0.203 CAK SMX 20 SMX CAL CAL C 0 1 N N N -1.426 -5.906 0.385 -2.938 -0.408 0.497 CAL SMX 21 SMX CAM CAM C 0 1 N N N -2.522 -5.072 -1.787 -0.907 -1.381 -0.680 CAM SMX 22 SMX SAR SAR S 0 1 N N N -1.199 -4.101 0.896 -4.185 -0.593 -0.802 SAR SMX 23 SMX SAS SAS S 0 1 N N N -2.979 -5.748 -3.452 0.889 -1.139 -0.837 SAS SMX 24 SMX CAT CAT C 0 1 N N N 0.674 -7.203 -1.157 -2.011 2.147 0.428 CAT SMX 25 SMX CAU CAU C 0 1 N N N -2.128 -6.674 -7.201 4.241 1.201 0.070 CAU SMX 26 SMX CAV CAV C 0 1 N N N -1.435 -5.952 -1.114 -1.589 -0.174 -0.132 CAV SMX 27 SMX CAX CAX C 0 1 N N N -0.439 -6.537 -1.876 -1.160 1.079 -0.127 CAX SMX 28 SMX CAY CAY C 0 1 Y N N -2.584 -7.854 -9.310 5.405 -0.880 0.678 CAY SMX 29 SMX CAZ CAZ C 0 1 Y N N 0.230 -3.726 0.160 -5.621 -0.847 0.186 CAZ SMX 30 SMX CBA CBA C 0 1 N N R -3.047 -7.619 -7.903 5.132 0.543 1.092 CBA SMX 31 SMX H1 H1 H 0 1 N N N -1.886 -7.895 -5.612 2.648 0.014 0.415 H1 SMX 32 SMX H2 H2 H 0 1 N N N -0.183 -5.390 -5.927 2.669 1.845 -1.930 H2 SMX 33 SMX H3 H3 H 0 1 N N N -1.043 -4.428 -3.890 0.712 0.590 -2.602 H3 SMX 34 SMX H4 H4 H 0 1 N N N 2.852 -4.590 1.931 -7.609 -0.101 -1.987 H4 SMX 35 SMX H5 H5 H 0 1 N N N 1.325 -3.974 2.648 -6.525 -1.482 -2.286 H5 SMX 36 SMX H6 H6 H 0 1 N N N 1.362 -5.592 1.869 -8.195 -1.763 -1.737 H6 SMX 37 SMX H7 H7 H 0 1 N N N 1.322 -8.249 0.135 -2.543 3.136 2.063 H7 SMX 38 SMX H8 H8 H 0 1 N N N -1.549 -8.337 -12.941 6.104 -4.510 -0.377 H8 SMX 39 SMX H9 H9 H 0 1 N N N -3.714 -7.320 -12.429 4.269 -4.015 1.189 H9 SMX 40 SMX H10 H10 H 0 1 N N N -0.004 -8.998 -11.129 7.487 -2.680 -1.272 H10 SMX 41 SMX H11 H11 H 0 1 N N N -4.387 -7.006 -10.099 3.824 -1.690 1.868 H11 SMX 42 SMX H12 H12 H 0 1 N N N -0.683 -8.696 -8.778 7.041 -0.355 -0.594 H12 SMX 43 SMX H13 H13 H 0 1 N N N -2.378 -6.291 0.778 -3.196 0.440 1.130 H13 SMX 44 SMX H14 H14 H 0 1 N N N -0.596 -6.514 0.774 -2.906 -1.315 1.100 H14 SMX 45 SMX H15 H15 H 0 1 N N N -2.135 -4.049 -1.907 -1.321 -1.606 -1.663 H15 SMX 46 SMX H16 H16 H 0 1 N N N -3.417 -5.053 -1.148 -1.094 -2.226 -0.016 H16 SMX 47 SMX H17 H17 H 0 1 N N N -3.930 -8.605 -6.717 6.860 1.293 0.350 H17 SMX 48 SMX H18 H18 H 0 1 N N N -3.899 -6.950 -8.093 4.637 0.550 2.063 H18 SMX 49 # # 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 SMX CAG CAH DOUB Y N 1 SMX CAG CAI SING Y N 2 SMX CAH CAJ SING Y N 3 SMX CAI CAK DOUB Y N 4 SMX CAJ CAY DOUB Y N 5 SMX CAK CAY SING Y N 6 SMX CAY CBA SING N N 7 SMX CBA OAF SING N N 8 SMX CBA CAU SING N N 9 SMX OAC CAU DOUB N N 10 SMX CAU N SING N N 11 SMX N CA SING N N 12 SMX CA C SING N N 13 SMX CA CB SING N N 14 SMX O C DOUB N N 15 SMX C NBD SING N N 16 SMX CB SAS SING N N 17 SMX CB NBD SING N N 18 SMX SAS CAM SING N N 19 SMX NBD CAX SING N N 20 SMX CAX CAT SING N N 21 SMX CAX CAV DOUB N N 22 SMX CAM CAV SING N N 23 SMX OAB CAT DOUB N N 24 SMX NAN NAO SING Y N 25 SMX NAN NAP DOUB Y N 26 SMX CAT OAE SING N N 27 SMX CAV CAL SING N N 28 SMX NAO CAZ DOUB Y N 29 SMX NAP NBE SING Y N 30 SMX CAZ NBE SING Y N 31 SMX CAZ SAR SING N N 32 SMX CAL SAR SING N N 33 SMX NBE CAA SING N N 34 SMX N H1 SING N N 35 SMX CA H2 SING N N 36 SMX CB H3 SING N N 37 SMX CAA H4 SING N N 38 SMX CAA H5 SING N N 39 SMX CAA H6 SING N N 40 SMX OAE H7 SING N N 41 SMX CAG H8 SING N N 42 SMX CAH H9 SING N N 43 SMX CAI H10 SING N N 44 SMX CAJ H11 SING N N 45 SMX CAK H12 SING N N 46 SMX CAL H13 SING N N 47 SMX CAL H14 SING N N 48 SMX CAM H15 SING N N 49 SMX CAM H16 SING N N 50 SMX OAF H17 SING N N 51 SMX CBA H18 SING N N 52 # # 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 SMX SMILES ACDLabs 12.01 "O=C(O)C=2N4C(=O)C(NC(=O)C(O)c1ccccc1)C4SCC=2CSc3nnnn3C" SMX InChI InChI 1.03 "InChI=1S/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1" SMX InChIKey InChI 1.03 OLVCFLKTBJRLHI-AXAPSJFSSA-N SMX SMILES_CANONICAL CACTVS 3.370 "Cn1nnnc1SCC2=C(N3[C@H](SC2)[C@H](NC(=O)[C@H](O)c4ccccc4)C3=O)C(O)=O" SMX SMILES CACTVS 3.370 "Cn1nnnc1SCC2=C(N3[CH](SC2)[CH](NC(=O)[CH](O)c4ccccc4)C3=O)C(O)=O" SMX SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "Cn1c(nnn1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)C(c4ccccc4)O)SC2)C(=O)O" SMX SMILES "OpenEye OEToolkits" 1.7.6 "Cn1c(nnn1)SCC2=C(N3C(C(C3=O)NC(=O)C(c4ccccc4)O)SC2)C(=O)O" # # 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 SMX "SYSTEMATIC NAME" ACDLabs 12.01 "(6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid" SMX "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "(6R,7R)-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanylmethyl]-8-oxidanylidene-7-[(2-oxidanyl-2-phenyl-ethanoyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-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 SMX "Create component" 2010-09-17 RCSB SMX "Modify aromatic_flag" 2011-06-04 RCSB SMX "Modify descriptor" 2011-06-04 RCSB SMX "Other modification" 2012-05-16 RCSB SMX "Modify synonyms" 2021-03-13 RCSB # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id SMX _pdbx_chem_comp_synonyms.name "CEFAMANDOLE, free form" _pdbx_chem_comp_synonyms.provenance PDB _pdbx_chem_comp_synonyms.type ? ##