data_ISX # _chem_comp.id ISX _chem_comp.name "(3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)piperidin-3-yl beta-D-glucopyranoside" _chem_comp.type D-saccharide _chem_comp.pdbx_type ATOMS _chem_comp.formula "C12 H23 N O8" _chem_comp.mon_nstd_parent_comp_id BGC _chem_comp.pdbx_synonyms ;GLUCOSE BETA-1,3-ISOFAGAMINE; (3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)piperidin-3-yl beta-D-glucoside; (3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)piperidin-3-yl D-glucoside; (3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)piperidin-3-yl glucoside ; _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2005-06-27 _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 309.313 _chem_comp.one_letter_code ? _chem_comp.three_letter_code ISX _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 N _chem_comp.pdbx_model_coordinates_db_code 2BVD _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site EBI # # 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 ISX "GLUCOSE BETA-1,3-ISOFAGAMINE" PDB ? 2 ISX "(3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)piperidin-3-yl beta-D-glucoside" PDB ? 3 ISX "(3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)piperidin-3-yl D-glucoside" PDB ? 4 ISX "(3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)piperidin-3-yl glucoside" 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 ISX O6A O6 O 0 1 N N N 15.149 34.662 17.145 0.793 0.426 5.960 O6A ISX 1 ISX C5A C5 C 0 1 N N N 19.211 34.266 14.622 -0.998 -1.584 1.677 C5A ISX 2 ISX N5 N5 N 0 1 N N N 17.955 33.988 13.934 -0.158 -2.132 2.748 N5 ISX 3 ISX C4A C4 C 0 1 N N R 19.290 33.605 16.002 -0.473 -0.208 1.261 C4A ISX 4 ISX O1 O4 O 0 1 N N N 20.350 34.228 16.743 -1.276 0.305 0.196 O1 ISX 5 ISX C3A C3 C 0 1 N N R 18.016 33.777 16.818 -0.541 0.741 2.460 C3A ISX 6 ISX O3A O3 O 0 1 N N N 18.149 33.037 18.043 0.042 1.998 2.109 O3A ISX 7 ISX C2A C2 C 0 1 N N R 16.819 33.315 15.979 0.229 0.122 3.630 C2A ISX 8 ISX C1A C1 C 0 1 N N N 16.715 34.139 14.697 -0.331 -1.270 3.922 C1A ISX 9 ISX C1 C1A C 0 1 N N R 21.598 33.581 16.550 -0.678 -0.137 -1.023 C1 ISX 10 ISX C2 C2A C 0 1 N N R 22.695 34.565 16.946 -1.496 0.379 -2.208 C2 ISX 11 ISX O2 O2A O 0 1 N N N 22.742 35.676 16.037 -2.839 -0.097 -2.106 O2 ISX 12 ISX C3 C3A C 0 1 N N S 24.059 33.881 17.040 -0.867 -0.131 -3.509 C3 ISX 13 ISX O3 O3A O 0 1 N N N 25.009 34.810 17.573 -1.528 0.461 -4.629 O3 ISX 14 ISX C4 C4A C 0 1 N N S 23.987 32.622 17.908 0.615 0.257 -3.522 C4 ISX 15 ISX O4 O4A O 0 1 N N N 25.250 31.945 17.917 1.256 -0.333 -4.654 O4 ISX 16 ISX C5 C5A C 0 1 N N R 22.881 31.717 17.348 1.274 -0.249 -2.237 C5 ISX 17 ISX C6A C6 C 0 1 N N N 15.484 33.333 16.732 0.076 1.006 4.869 C6A ISX 18 ISX C6 C6A C 0 1 N N N 22.702 30.437 18.149 2.762 0.105 -2.256 C6 ISX 19 ISX O6 O6A O 0 1 N N N 22.178 30.776 19.439 3.381 -0.373 -1.061 O6 ISX 20 ISX O5 O5A O 0 1 N N N 21.658 32.442 17.413 0.656 0.358 -1.105 O5 ISX 21 ISX H6 H6 H 0 1 N N N 14.322 34.673 17.612 0.671 1.012 6.719 H6 ISX 22 ISX H5C1 H5C1 H 0 0 N N N 19.393 35.364 14.694 -0.975 -2.256 0.819 H5C1 ISX 23 ISX H5C2 H5C2 H 0 0 N N N 20.084 33.979 13.991 -2.023 -1.488 2.034 H5C2 ISX 24 ISX H5A H5 H 0 1 N N N 17.991 33.051 13.533 -0.546 -3.031 2.989 H5A ISX 25 ISX H4A H4 H 0 1 N N N 19.510 32.519 15.881 0.560 -0.299 0.927 H4A ISX 26 ISX H3A H3 H 0 1 N N N 17.888 34.857 17.062 -1.581 0.891 2.749 H3A ISX 27 ISX HA HA H 0 1 N N N 17.354 33.144 18.552 -0.469 2.346 1.366 HA ISX 28 ISX H2A H2 H 0 1 N N N 17.014 32.259 15.678 1.285 0.042 3.368 H2A ISX 29 ISX H1C1 H1C1 H 0 0 N N N 15.812 33.879 14.097 0.198 -1.703 4.771 H1C1 ISX 30 ISX H1C2 H1C2 H 0 0 N N N 16.466 35.207 14.897 -1.392 -1.191 4.161 H1C2 ISX 31 ISX H1 H1A H 0 1 N N N 21.717 33.271 15.486 -0.661 -1.227 -1.042 H1 ISX 32 ISX H2 H2A H 0 1 N N N 22.445 34.964 17.957 -1.495 1.469 -2.206 H2 ISX 33 ISX HO2 HB H 0 1 N Y N 23.425 36.289 16.284 -3.195 0.246 -1.276 HO2 ISX 34 ISX H3 H3A H 0 1 N N N 24.383 33.589 16.014 -0.961 -1.215 -3.561 H3 ISX 35 ISX HO3 HC H 0 1 N Y N 25.857 34.385 17.631 -2.455 0.191 -4.582 HO3 ISX 36 ISX H4 H4A H 0 1 N N N 23.724 32.914 18.951 0.707 1.342 -3.576 H4 ISX 37 ISX HO4 HD H 0 1 N Y N 25.205 31.164 18.456 0.811 0.012 -5.439 HO4 ISX 38 ISX H5 H5A H 0 1 N N N 23.108 31.464 16.286 1.160 -1.331 -2.174 H5 ISX 39 ISX H6C1 H6C1 H 0 0 N N N 14.666 32.869 16.132 -0.979 1.085 5.130 H6C1 ISX 40 ISX H6C2 H6C2 H 0 0 N N N 15.486 32.623 17.591 0.474 1.998 4.659 H6C2 ISX 41 ISX H61 H6A1 H 0 1 N N N 23.640 29.838 18.212 3.235 -0.358 -3.122 H61 ISX 42 ISX H62 H6A2 H 0 1 N N N 22.075 29.684 17.617 2.877 1.187 -2.317 H62 ISX 43 ISX HO6 H6A H 0 1 N Y N 22.066 29.976 19.939 4.316 -0.129 -1.113 HO6 ISX 44 # # 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 ISX O6A C6A SING N N 1 ISX O6A H6 SING N N 2 ISX C5A N5 SING N N 3 ISX C5A C4A SING N N 4 ISX C5A H5C1 SING N N 5 ISX C5A H5C2 SING N N 6 ISX N5 C1A SING N N 7 ISX N5 H5A SING N N 8 ISX C4A O1 SING N N 9 ISX C4A C3A SING N N 10 ISX C4A H4A SING N N 11 ISX O1 C1 SING N N 12 ISX C3A O3A SING N N 13 ISX C3A C2A SING N N 14 ISX C3A H3A SING N N 15 ISX O3A HA SING N N 16 ISX C2A C1A SING N N 17 ISX C2A C6A SING N N 18 ISX C2A H2A SING N N 19 ISX C1A H1C1 SING N N 20 ISX C1A H1C2 SING N N 21 ISX C1 C2 SING N N 22 ISX C1 O5 SING N N 23 ISX C1 H1 SING N N 24 ISX C2 O2 SING N N 25 ISX C2 C3 SING N N 26 ISX C2 H2 SING N N 27 ISX O2 HO2 SING N N 28 ISX C3 O3 SING N N 29 ISX C3 C4 SING N N 30 ISX C3 H3 SING N N 31 ISX O3 HO3 SING N N 32 ISX C4 O4 SING N N 33 ISX C4 C5 SING N N 34 ISX C4 H4 SING N N 35 ISX O4 HO4 SING N N 36 ISX C5 C6 SING N N 37 ISX C5 O5 SING N N 38 ISX C5 H5 SING N N 39 ISX C6A H6C1 SING N N 40 ISX C6A H6C2 SING N N 41 ISX C6 O6 SING N N 42 ISX C6 H61 SING N N 43 ISX C6 H62 SING N N 44 ISX O6 HO6 SING N N 45 # # 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 ISX SMILES ACDLabs 10.04 "O(C1CNCC(CO)C1O)C2OC(C(O)C(O)C2O)CO" ISX SMILES_CANONICAL CACTVS 3.341 "OC[C@H]1CNC[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]1O" ISX SMILES CACTVS 3.341 "OC[CH]1CNC[CH](O[CH]2O[CH](CO)[CH](O)[CH](O)[CH]2O)[CH]1O" ISX SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C1[C@@H]([C@H]([C@@H](CN1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)CO" ISX SMILES "OpenEye OEToolkits" 1.5.0 "C1C(C(C(CN1)OC2C(C(C(C(O2)CO)O)O)O)O)CO" ISX InChI InChI 1.03 "InChI=1S/C12H23NO8/c14-3-5-1-13-2-6(8(5)16)20-12-11(19)10(18)9(17)7(4-15)21-12/h5-19H,1-4H2/t5-,6-,7-,8-,9-,10+,11-,12-/m1/s1" ISX InChIKey InChI 1.03 BEXVSXHKIARRKH-FYKVHUBJSA-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 ISX "SYSTEMATIC NAME" ACDLabs 10.04 "(3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)piperidin-3-yl beta-D-glucopyranoside" ISX "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2R,3R,4S,5S,6R)-2-[(3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)piperidin-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol" # _pdbx_chem_comp_related.comp_id ISX _pdbx_chem_comp_related.related_comp_id BGC _pdbx_chem_comp_related.relationship_type "Carbohydrate core" _pdbx_chem_comp_related.details ? # # loop_ _pdbx_chem_comp_atom_related.ordinal _pdbx_chem_comp_atom_related.comp_id _pdbx_chem_comp_atom_related.atom_id _pdbx_chem_comp_atom_related.related_comp_id _pdbx_chem_comp_atom_related.related_atom_id _pdbx_chem_comp_atom_related.related_type 1 ISX C1 BGC C1 "Carbohydrate core" 2 ISX C2 BGC C2 "Carbohydrate core" 3 ISX C3 BGC C3 "Carbohydrate core" 4 ISX C4 BGC C4 "Carbohydrate core" 5 ISX C5 BGC C5 "Carbohydrate core" 6 ISX C6 BGC C6 "Carbohydrate core" 7 ISX O2 BGC O2 "Carbohydrate core" 8 ISX O3 BGC O3 "Carbohydrate core" 9 ISX O1 BGC O1 "Carbohydrate core" 10 ISX O4 BGC O4 "Carbohydrate core" 11 ISX O5 BGC O5 "Carbohydrate core" 12 ISX O6 BGC O6 "Carbohydrate core" 13 ISX H1 BGC H1 "Carbohydrate core" 14 ISX H2 BGC H2 "Carbohydrate core" 15 ISX H3 BGC H3 "Carbohydrate core" 16 ISX H4 BGC H4 "Carbohydrate core" 17 ISX H5 BGC H5 "Carbohydrate core" 18 ISX HO6 BGC HO6 "Carbohydrate core" 19 ISX H61 BGC H61 "Carbohydrate core" 20 ISX H62 BGC H62 "Carbohydrate core" 21 ISX HO2 BGC HO2 "Carbohydrate core" 22 ISX HO3 BGC HO3 "Carbohydrate core" 23 ISX HO4 BGC HO4 "Carbohydrate core" # # 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 ISX "CARBOHYDRATE ISOMER" D PDB ? ISX "CARBOHYDRATE RING" pyranose PDB ? ISX "CARBOHYDRATE ANOMER" beta PDB ? ISX "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 ISX "Create component" 2005-06-27 EBI ISX "Modify descriptor" 2011-06-04 RCSB ISX "Other modification" 2020-07-03 RCSB ISX "Modify parent residue" 2020-07-17 RCSB ISX "Modify name" 2020-07-17 RCSB ISX "Modify synonyms" 2020-07-17 RCSB ISX "Modify internal type" 2020-07-17 RCSB ISX "Modify linking type" 2020-07-17 RCSB ISX "Modify atom id" 2020-07-17 RCSB ISX "Modify component atom id" 2020-07-17 RCSB ISX "Modify leaving atom flag" 2020-07-17 RCSB ##