data_GPQ # _chem_comp.id GPQ _chem_comp.name "5-chloro-1-(beta-D-glucopyranosyl)pyrimidine-2,4(1H,3H)-dione" _chem_comp.type D-saccharide _chem_comp.pdbx_type ATOMS _chem_comp.formula "C10 H13 Cl N2 O7" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ;5-chloro-1-(beta-D-glucosyl)pyrimidine-2,4(1H,3H)-dione; 5-chloro-1-(D-glucosyl)pyrimidine-2,4(1H,3H)-dione; 5-chloro-1-(glucosyl)pyrimidine-2,4(1H,3H)-dione ; _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2011-08-10 _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 308.672 _chem_comp.one_letter_code ? _chem_comp.three_letter_code GPQ _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 3T3E _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 GPQ "5-chloro-1-(beta-D-glucosyl)pyrimidine-2,4(1H,3H)-dione" PDB ? 2 GPQ "5-chloro-1-(D-glucosyl)pyrimidine-2,4(1H,3H)-dione" PDB ? 3 GPQ "5-chloro-1-(glucosyl)pyrimidine-2,4(1H,3H)-dione" 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 GPQ N1 N1 N 0 1 N N N 34.091 23.415 28.762 0.832 0.228 0.545 N1 GPQ 1 GPQ CL1 CL1 CL 0 1 N N N 37.941 23.947 29.641 3.550 -0.994 -2.062 CL1 GPQ 2 GPQ C2A C2 C 0 1 N N N 33.418 24.141 29.751 1.575 0.621 1.595 C2A GPQ 3 GPQ O2A O2 O 0 1 N N N 32.199 24.199 29.753 1.025 1.059 2.587 O2A GPQ 4 GPQ N3 N3 N 0 1 N N N 34.132 24.845 30.682 2.918 0.534 1.565 N3 GPQ 5 GPQ C4A C4 C 0 1 N N N 35.529 24.818 30.656 3.543 0.050 0.473 C4A GPQ 6 GPQ O4A O4 O 0 1 N N N 36.090 25.483 31.509 4.758 -0.029 0.444 O4A GPQ 7 GPQ C5A C5 C 0 1 N N N 36.217 24.077 29.687 2.773 -0.367 -0.641 C5A GPQ 8 GPQ C6A C6 C 0 1 N N N 35.496 23.380 28.735 1.428 -0.270 -0.583 C6A GPQ 9 GPQ C1 "C1'" C 0 1 N N R 33.268 22.726 27.804 -0.628 0.327 0.611 C1 GPQ 10 GPQ C2 "C2'" C 0 1 N N R 33.695 23.039 26.337 -1.118 1.343 -0.426 C2 GPQ 11 GPQ O2 "O2'" O 0 1 N N N 33.820 24.452 26.169 -0.587 2.633 -0.117 O2 GPQ 12 GPQ C3 "C3'" C 0 1 N N S 32.637 22.405 25.390 -2.648 1.397 -0.392 C3 GPQ 13 GPQ O3 "O3'" O 0 1 N N N 33.068 22.343 24.041 -3.117 2.288 -1.406 O3 GPQ 14 GPQ C4 "C4'" C 0 1 N N S 32.368 20.953 25.846 -3.204 -0.007 -0.647 C4 GPQ 15 GPQ O4 "O4'" O 0 1 N N N 31.290 20.479 25.090 -4.629 0.017 -0.546 O4 GPQ 16 GPQ C5 "C5'" C 0 1 N N R 32.065 20.799 27.369 -2.634 -0.971 0.398 C5 GPQ 17 GPQ O5 "O5'" O 0 1 N N N 33.199 21.288 28.089 -1.206 -0.950 0.334 O5 GPQ 18 GPQ C6 "C6'" C 0 1 N N N 32.050 19.352 27.805 -3.136 -2.387 0.113 C6 GPQ 19 GPQ O6 "O6'" O 0 1 N N N 33.208 18.656 27.304 -2.700 -3.265 1.153 O6 GPQ 20 GPQ HN3 HN3 H 0 1 N N N 33.655 25.378 31.380 3.438 0.822 2.331 HN3 GPQ 21 GPQ H6 H6 H 0 1 N N N 36.010 22.811 27.974 0.824 -0.584 -1.423 H6 GPQ 22 GPQ H1 "H1'" H 0 1 N N N 32.243 23.111 27.907 -0.926 0.653 1.607 H1 GPQ 23 GPQ H2 "H2'" H 0 1 N N N 34.677 22.607 26.094 -0.785 1.040 -1.418 H2 GPQ 24 GPQ HO2 "HO2'" H 0 1 N Y N 34.080 24.643 25.276 -0.857 3.327 -0.734 HO2 GPQ 25 GPQ H3 "H3'" H 0 1 N N N 31.741 23.041 25.443 -2.979 1.750 0.585 H3 GPQ 26 GPQ HO3 "HO3'" H 0 1 N Y N 32.387 21.949 23.508 -4.080 2.371 -1.442 HO3 GPQ 27 GPQ H4 "H4'" H 0 1 N N N 33.286 20.370 25.683 -2.915 -0.338 -1.645 H4 GPQ 28 GPQ HO4 "HO4'" H 0 1 N Y N 31.094 19.585 25.343 -5.057 0.612 -1.177 HO4 GPQ 29 GPQ H5 "H5'" H 0 1 N N N 31.106 21.306 27.549 -2.958 -0.662 1.391 H5 GPQ 30 GPQ H61 "H6'" H 0 1 N N N 32.052 19.308 28.904 -4.226 -2.385 0.073 H61 GPQ 31 GPQ H62 "H6'A" H 0 1 N N N 31.143 18.868 27.413 -2.738 -2.730 -0.842 H62 GPQ 32 GPQ HO6 "HO6'" H 0 1 N Y N 33.181 17.750 27.588 -2.983 -4.182 1.038 HO6 GPQ 33 # # 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 GPQ N1 C2A SING N N 1 GPQ N1 C6A SING N N 2 GPQ N1 C1 SING N N 3 GPQ CL1 C5A SING N N 4 GPQ C2A O2A DOUB N N 5 GPQ C2A N3 SING N N 6 GPQ N3 C4A SING N N 7 GPQ C4A O4A DOUB N N 8 GPQ C4A C5A SING N N 9 GPQ C5A C6A DOUB N N 10 GPQ C1 C2 SING N N 11 GPQ C1 O5 SING N N 12 GPQ C2 O2 SING N N 13 GPQ C2 C3 SING N N 14 GPQ C3 O3 SING N N 15 GPQ C3 C4 SING N N 16 GPQ C4 O4 SING N N 17 GPQ C4 C5 SING N N 18 GPQ C5 O5 SING N N 19 GPQ C5 C6 SING N N 20 GPQ C6 O6 SING N N 21 GPQ N3 HN3 SING N N 22 GPQ C6A H6 SING N N 23 GPQ C1 H1 SING N N 24 GPQ C2 H2 SING N N 25 GPQ O2 HO2 SING N N 26 GPQ C3 H3 SING N N 27 GPQ O3 HO3 SING N N 28 GPQ C4 H4 SING N N 29 GPQ O4 HO4 SING N N 30 GPQ C5 H5 SING N N 31 GPQ C6 H61 SING N N 32 GPQ C6 H62 SING N N 33 GPQ O6 HO6 SING N N 34 # # 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 GPQ SMILES ACDLabs 12.01 "ClC1=CN(C(=O)NC1=O)C2OC(C(O)C(O)C2O)CO" GPQ InChI InChI 1.03 "InChI=1S/C10H13ClN2O7/c11-3-1-13(10(19)12-8(3)18)9-7(17)6(16)5(15)4(2-14)20-9/h1,4-7,9,14-17H,2H2,(H,12,18,19)/t4-,5-,6+,7-,9-/m1/s1" GPQ InChIKey InChI 1.03 NONSBAHWXCNSII-XSEHCYKFSA-N GPQ SMILES_CANONICAL CACTVS 3.370 "OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)N2C=C(Cl)C(=O)NC2=O" GPQ SMILES CACTVS 3.370 "OC[CH]1O[CH]([CH](O)[CH](O)[CH]1O)N2C=C(Cl)C(=O)NC2=O" GPQ SMILES_CANONICAL "OpenEye OEToolkits" 1.7.2 "C1=C(C(=O)NC(=O)N1[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)Cl" GPQ SMILES "OpenEye OEToolkits" 1.7.2 "C1=C(C(=O)NC(=O)N1C2C(C(C(C(O2)CO)O)O)O)Cl" # # 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 GPQ "SYSTEMATIC NAME" ACDLabs 12.01 "5-chloro-1-(beta-D-glucopyranosyl)pyrimidine-2,4(1H,3H)-dione" GPQ "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.2 "5-chloranyl-1-[(2R,3R,4S,5S,6R)-6-(hydroxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]pyrimidine-2,4-dione" # # 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 GPQ "CARBOHYDRATE ISOMER" D PDB ? GPQ "CARBOHYDRATE RING" pyranose PDB ? GPQ "CARBOHYDRATE ANOMER" beta PDB ? GPQ "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 GPQ "Create component" 2011-08-10 RCSB GPQ "Other modification" 2020-07-03 RCSB GPQ "Modify synonyms" 2020-07-17 RCSB GPQ "Modify internal type" 2020-07-17 RCSB GPQ "Modify linking type" 2020-07-17 RCSB GPQ "Modify atom id" 2020-07-17 RCSB GPQ "Modify component atom id" 2020-07-17 RCSB GPQ "Modify leaving atom flag" 2020-07-17 RCSB ##