data_22O # _chem_comp.id 22O _chem_comp.name "N-({(2E)-2-[(3-bromophenyl)methylidene]hydrazino}carbonothioyl)-beta-D-glucopyranosylamine" _chem_comp.type D-saccharide _chem_comp.pdbx_type ATOMS _chem_comp.formula "C14 H18 Br N3 O5 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ;3-bromobenzaldehyde-4-(beta-D-glucopyranosyl) thiosemicarbazone; N-({(2E)-2-[(3-bromophenyl)methylidene]hydrazino}carbonothioyl)-beta-D-glucosylamine; N-({(2E)-2-[(3-bromophenyl)methylidene]hydrazino}carbonothioyl)-D-glucosylamine; N-({(2E)-2-[(3-bromophenyl)methylidene]hydrazino}carbonothioyl)-glucosylamine ; _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2010-05-03 _chem_comp.pdbx_modified_date 2020-07-17 _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 420.279 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 22O _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 3MTA _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site RCSB # # loop_ _pdbx_chem_comp_synonyms.ordinal _pdbx_chem_comp_synonyms.comp_id _pdbx_chem_comp_synonyms.name _pdbx_chem_comp_synonyms.provenance _pdbx_chem_comp_synonyms.type 1 22O "3-bromobenzaldehyde-4-(beta-D-glucopyranosyl) thiosemicarbazone" PDB ? 2 22O "N-({(2E)-2-[(3-bromophenyl)methylidene]hydrazino}carbonothioyl)-beta-D-glucosylamine" PDB ? 3 22O "N-({(2E)-2-[(3-bromophenyl)methylidene]hydrazino}carbonothioyl)-D-glucosylamine" PDB ? 4 22O "N-({(2E)-2-[(3-bromophenyl)methylidene]hydrazino}carbonothioyl)-glucosylamine" PDB ? # # 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 22O C1 C1 C 0 1 N N R 19.176 15.270 56.010 -2.646 -0.391 0.442 C1 22O 1 22O N1 N1 N 0 1 N N N 18.725 13.924 55.566 -1.316 -1.001 0.363 N1 22O 2 22O S1 S1 S 0 1 N N N 18.271 13.211 58.153 -2.571 -3.330 0.598 S1 22O 3 22O BR1 BR1 BR 0 1 N N N 19.241 11.675 49.548 4.358 2.281 -0.303 BR1 22O 4 22O C2 C2 C 0 1 N N R 20.618 15.635 55.578 -2.553 0.940 1.192 C2 22O 5 22O N2 N2 N 0 1 N N N 17.910 11.785 55.948 0.038 -2.902 0.353 N2 22O 6 22O O2 O2 O 0 1 N N N 21.576 14.818 56.264 -2.111 0.705 2.530 O2 22O 7 22O C3 C3 C 0 1 N N S 20.908 17.129 55.834 -3.935 1.600 1.218 C3 22O 8 22O N3 N3 N 0 1 N N N 17.909 11.547 54.743 1.173 -2.092 0.212 N3 22O 9 22O O3 O3 O 0 1 N N N 22.162 17.520 55.259 -3.844 2.876 1.854 O3 22O 10 22O C4 C4 C 0 1 N N S 19.776 17.996 55.265 -4.433 1.776 -0.220 C4 22O 11 22O O4 O4 O 0 1 N N N 20.015 19.370 55.556 -5.752 2.325 -0.205 O4 22O 12 22O C5 C5 C 0 1 N N R 18.440 17.562 55.882 -4.453 0.413 -0.915 C5 22O 13 22O O5 O5 O 0 1 N N N 18.212 16.200 55.435 -3.144 -0.160 -0.877 O5 22O 14 22O C6 C6 C 0 1 N N N 17.225 18.474 55.583 -4.891 0.589 -2.370 C6 22O 15 22O O6 O6 O 0 1 N N N 17.216 18.905 54.216 -5.023 -0.694 -2.987 O6 22O 16 22O C7 C7 C 0 1 N N N 18.310 12.969 56.414 -1.185 -2.341 0.426 C7 22O 17 22O C8 C8 C 0 1 N N N 17.510 10.368 54.315 2.351 -2.632 0.141 C8 22O 18 22O C9 C9 C 0 1 Y N N 17.509 10.080 52.957 3.545 -1.780 -0.007 C9 22O 19 22O C10 C10 C 0 1 Y N N 16.786 8.991 52.472 4.815 -2.358 -0.083 C10 22O 20 22O C11 C11 C 0 1 Y N N 16.796 8.701 51.109 5.928 -1.556 -0.223 C11 22O 21 22O C12 C12 C 0 1 Y N N 17.527 9.500 50.235 5.790 -0.180 -0.288 C12 22O 22 22O C13 C13 C 0 1 Y N N 18.247 10.585 50.724 4.535 0.400 -0.213 C13 22O 23 22O C14 C14 C 0 1 Y N N 18.244 10.876 52.081 3.412 -0.392 -0.079 C14 22O 24 22O H1 H1 H 0 1 N N N 19.214 15.305 57.109 -3.322 -1.061 0.973 H1 22O 25 22O HN1 HN1 H 0 1 N N N 18.731 13.720 54.587 -0.531 -0.440 0.265 HN1 22O 26 22O H2 H2 H 0 1 N N N 20.706 15.445 54.498 -1.846 1.596 0.684 H2 22O 27 22O HN2 HN2 H 0 1 N N N 17.606 11.080 56.589 0.133 -3.866 0.398 HN2 22O 28 22O HO2 HO2 H 0 1 N Y N 22.453 15.056 55.986 -1.242 0.284 2.589 HO2 22O 29 22O H3 H3 H 0 1 N N N 20.967 17.281 56.922 -4.631 0.967 1.770 H3 22O 30 22O HO3 HO3 H 0 1 N Y N 22.316 18.442 55.431 -3.529 2.839 2.768 HO3 22O 31 22O H4 H4 H 0 1 N N N 19.738 17.865 54.173 -3.764 2.450 -0.756 H4 22O 32 22O HO4 HO4 H 0 1 N Y N 19.309 19.897 55.200 -5.815 3.188 0.226 HO4 22O 33 22O H5 H5 H 0 1 N N N 18.526 17.642 56.976 -5.153 -0.247 -0.402 H5 22O 34 22O H61 H6 H 0 1 N N N 16.301 17.911 55.783 -5.850 1.106 -2.401 H61 22O 35 22O H62 H6A H 0 1 N N N 17.278 19.359 56.234 -4.145 1.175 -2.907 H62 22O 36 22O HO6 HO6 H 0 1 N Y N 16.461 19.461 54.064 -5.299 -0.659 -3.913 HO6 22O 37 22O H8 H8 H 0 1 N N N 17.182 9.622 55.023 2.457 -3.706 0.192 H8 22O 38 22O H10 H10 H 0 1 N N N 16.219 8.373 53.152 4.925 -3.431 -0.032 H10 22O 39 22O H11 H11 H 0 1 N N N 16.237 7.857 50.731 6.910 -2.002 -0.281 H11 22O 40 22O H12 H12 H 0 1 N N N 17.535 9.278 49.178 6.665 0.443 -0.396 H12 22O 41 22O H14 H14 H 0 1 N N N 18.809 11.716 52.456 2.433 0.062 -0.025 H14 22O 42 # # 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 22O O5 C1 SING N N 1 22O N1 C1 SING N N 2 22O C2 C1 SING N N 3 22O C1 H1 SING N N 4 22O N1 C7 SING N N 5 22O N1 HN1 SING N N 6 22O C7 S1 DOUB N N 7 22O BR1 C13 SING N N 8 22O C2 C3 SING N N 9 22O C2 O2 SING N N 10 22O C2 H2 SING N N 11 22O N3 N2 SING N N 12 22O N2 C7 SING N N 13 22O N2 HN2 SING N N 14 22O O2 HO2 SING N N 15 22O O3 C3 SING N N 16 22O C4 C3 SING N N 17 22O C3 H3 SING N N 18 22O C8 N3 DOUB N N 19 22O O3 HO3 SING N N 20 22O C4 O4 SING N N 21 22O C4 C5 SING N N 22 22O C4 H4 SING N N 23 22O O4 HO4 SING N N 24 22O O5 C5 SING N N 25 22O C6 C5 SING N N 26 22O C5 H5 SING N N 27 22O O6 C6 SING N N 28 22O C6 H61 SING N N 29 22O C6 H62 SING N N 30 22O O6 HO6 SING N E 31 22O C9 C8 SING N N 32 22O C8 H8 SING N N 33 22O C14 C9 DOUB Y N 34 22O C10 C9 SING Y N 35 22O C11 C10 DOUB Y N 36 22O C10 H10 SING N N 37 22O C12 C11 SING Y N 38 22O C11 H11 SING N N 39 22O C12 C13 DOUB Y N 40 22O C12 H12 SING N N 41 22O C13 C14 SING Y N 42 22O C14 H14 SING N N 43 # # 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 22O SMILES ACDLabs 12.01 "S=C(NC1OC(C(O)C(O)C1O)CO)N/N=C/c2cccc(Br)c2" 22O SMILES_CANONICAL CACTVS 3.370 "OC[C@H]1O[C@@H](NC(=S)N/N=C/c2cccc(Br)c2)[C@H](O)[C@@H](O)[C@@H]1O" 22O SMILES CACTVS 3.370 "OC[CH]1O[CH](NC(=S)NN=Cc2cccc(Br)c2)[CH](O)[CH](O)[CH]1O" 22O SMILES_CANONICAL "OpenEye OEToolkits" 1.7.0 "c1cc(cc(c1)Br)/C=N/NC(=S)N[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O" 22O SMILES "OpenEye OEToolkits" 1.7.0 "c1cc(cc(c1)Br)C=NNC(=S)NC2C(C(C(C(O2)CO)O)O)O" 22O InChI InChI 1.03 "InChI=1S/C14H18BrN3O5S/c15-8-3-1-2-7(4-8)5-16-18-14(24)17-13-12(22)11(21)10(20)9(6-19)23-13/h1-5,9-13,19-22H,6H2,(H2,17,18,24)/b16-5+/t9-,10-,11+,12-,13-/m1/s1" 22O InChIKey InChI 1.03 PGBHKZPXJWINSR-QCOQDYPWSA-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 22O "SYSTEMATIC NAME" ACDLabs 12.01 "N-{[(2E)-2-(3-bromobenzylidene)hydrazinyl]carbothioyl}-beta-D-glucopyranosylamine" 22O "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.0 "1-[(E)-(3-bromophenyl)methylideneamino]-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]thiourea" # # loop_ _pdbx_chem_comp_feature.comp_id _pdbx_chem_comp_feature.type _pdbx_chem_comp_feature.value _pdbx_chem_comp_feature.source _pdbx_chem_comp_feature.support 22O "CARBOHYDRATE ISOMER" D PDB ? 22O "CARBOHYDRATE RING" pyranose PDB ? 22O "CARBOHYDRATE ANOMER" beta PDB ? 22O "CARBOHYDRATE PRIMARY CARBONYL GROUP" aldose PDB ? # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 22O "Create component" 2010-05-03 RCSB 22O "Modify aromatic_flag" 2011-06-04 RCSB 22O "Modify descriptor" 2011-06-04 RCSB 22O "Other modification" 2020-07-03 RCSB 22O "Modify synonyms" 2020-07-17 RCSB 22O "Modify internal type" 2020-07-17 RCSB 22O "Modify linking type" 2020-07-17 RCSB 22O "Modify atom id" 2020-07-17 RCSB 22O "Modify component atom id" 2020-07-17 RCSB 22O "Modify leaving atom flag" 2020-07-17 RCSB ##