data_9KU # _chem_comp.id 9KU _chem_comp.name "5-hydroxy-2-[(2S)-1-{[(naphthalen-1-yl)oxy]acetyl}pyrrolidin-2-yl]-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C21 H19 N3 O6" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms SRI-29789 _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2017-07-11 _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 409.392 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 9KU _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 5WCS _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 9KU C1 C1 C 0 1 N N N 65.065 80.498 3.064 -5.015 0.708 -0.535 C1 9KU 1 9KU C10 C2 C 0 1 Y N N 71.838 81.471 6.759 3.725 -1.507 1.071 C10 9KU 2 9KU C11 C3 C 0 1 Y N N 72.634 81.995 7.790 5.014 -1.558 1.594 C11 9KU 3 9KU C12 C4 C 0 1 Y N N 72.914 81.266 8.903 5.975 -0.686 1.181 C12 9KU 4 9KU C13 C5 C 0 1 Y N N 72.409 79.953 9.056 5.666 0.284 0.211 C13 9KU 5 9KU C14 C6 C 0 1 Y N N 71.601 79.410 8.023 4.355 0.339 -0.325 C14 9KU 6 9KU C15 C7 C 0 1 Y N N 71.090 78.098 8.164 4.046 1.307 -1.293 C15 9KU 7 9KU C16 C8 C 0 1 Y N N 71.374 77.365 9.283 5.008 2.179 -1.704 C16 9KU 8 9KU C17 C9 C 0 1 Y N N 72.173 77.902 10.304 6.297 2.125 -1.179 C17 9KU 9 9KU C18 C10 C 0 1 Y N N 72.677 79.159 10.196 6.632 1.200 -0.239 C18 9KU 10 9KU C19 C11 C 0 1 N N N 69.542 82.373 2.779 -1.137 -3.215 0.772 C19 9KU 11 9KU C2 C12 C 0 1 N N N 64.029 80.876 3.913 -4.201 1.735 0.129 C2 9KU 12 9KU C20 C13 C 0 1 N N N 68.551 83.151 1.946 -2.279 -4.170 0.344 C20 9KU 13 9KU C21 C14 C 0 1 N N N 67.902 84.044 2.992 -3.362 -3.167 -0.134 C21 9KU 14 9KU C3 C15 C 0 1 N N N 64.205 81.915 4.777 -2.888 1.416 0.438 C3 9KU 15 9KU C4 C16 C 0 1 N N N 63.093 82.345 5.713 -2.018 2.408 1.107 C4 9KU 16 9KU C5 C17 C 0 1 N N N 66.360 82.264 4.039 -3.143 -0.702 -0.465 C5 9KU 17 9KU C6 C18 C 0 1 N N S 67.640 83.063 4.148 -2.528 -2.041 -0.781 C6 9KU 18 9KU C7 C19 C 0 1 N N N 69.140 81.327 5.027 -0.141 -1.316 -0.534 C7 9KU 19 9KU C8 C20 C 0 1 N N N 70.227 80.318 4.762 1.197 -1.508 0.132 C8 9KU 20 9KU C9 C21 C 0 1 Y N N 71.327 80.205 6.872 3.386 -0.580 0.127 C9 9KU 21 9KU N1 N1 N 0 1 N N N 65.352 82.605 4.843 -2.411 0.198 0.123 N1 9KU 22 9KU N2 N2 N 0 1 N N N 68.818 82.183 4.044 -1.175 -2.117 -0.211 N2 9KU 23 9KU N3 N3 N 0 1 N N N 66.232 81.224 3.156 -4.436 -0.482 -0.805 N3 9KU 24 9KU O1 O1 O 0 1 N N N 64.983 79.564 2.252 -6.179 0.922 -0.829 O1 9KU 25 9KU O2 O2 O 0 1 N N N 62.895 80.167 3.820 -4.717 2.953 0.430 O2 9KU 26 9KU O3 O3 O 0 1 N N N 63.338 83.280 6.496 -0.742 2.092 1.404 O3 9KU 27 9KU O4 O4 O 0 1 N N N 62.013 81.734 5.631 -2.453 3.506 1.389 O4 9KU 28 9KU O5 O5 O 0 1 N N N 70.550 79.589 5.939 2.124 -0.544 -0.374 O5 9KU 29 9KU O6 O6 O 0 1 N N N 68.568 81.380 6.112 -0.287 -0.441 -1.361 O6 9KU 30 9KU H1 H1 H 0 1 N N N 71.629 82.064 5.880 2.984 -2.214 1.414 H1 9KU 31 9KU H2 H2 H 0 1 N N N 73.031 82.995 7.697 5.257 -2.300 2.340 H2 9KU 32 9KU H3 H3 H 0 1 N N N 73.530 81.694 9.680 6.970 -0.738 1.597 H3 9KU 33 9KU H4 H4 H 0 1 N N N 70.474 77.674 7.385 3.051 1.360 -1.709 H4 9KU 34 9KU H5 H5 H 0 1 N N N 70.980 76.364 9.382 4.768 2.924 -2.449 H5 9KU 35 9KU H6 H6 H 0 1 N N N 72.389 77.312 11.182 7.042 2.828 -1.523 H6 9KU 36 9KU H7 H7 H 0 1 N N N 73.290 79.557 10.991 7.635 1.170 0.160 H7 9KU 37 9KU H8 H8 H 0 1 N N N 69.783 81.407 2.310 -1.320 -2.831 1.776 H8 9KU 38 9KU H9 H9 H 0 1 N N N 70.468 82.947 2.934 -0.176 -3.728 0.731 H9 9KU 39 9KU H10 H10 H 0 1 N N N 69.058 83.745 1.171 -1.961 -4.819 -0.472 H10 9KU 40 9KU H11 H11 H 0 1 N N N 67.814 82.485 1.474 -2.636 -4.756 1.191 H11 9KU 41 9KU H12 H12 H 0 1 N N N 68.581 84.852 3.302 -4.020 -3.631 -0.869 H12 9KU 42 9KU H13 H13 H 0 1 N N N 66.963 84.478 2.618 -3.934 -2.786 0.712 H13 9KU 43 9KU H14 H14 H 0 1 N N N 67.656 83.610 5.102 -2.487 -2.184 -1.861 H14 9KU 44 9KU H15 H15 H 0 1 N N N 69.884 79.616 3.988 1.089 -1.377 1.209 H15 9KU 45 9KU H16 H16 H 0 1 N N N 71.126 80.844 4.408 1.567 -2.511 -0.077 H16 9KU 46 9KU H17 H17 H 0 1 N N N 67.003 80.987 2.565 -4.947 -1.181 -1.243 H17 9KU 47 9KU H18 H18 H 0 1 N N N 62.254 80.512 4.431 -5.641 3.064 0.169 H18 9KU 48 9KU H19 H19 H 0 1 N N N 62.570 83.459 7.026 -0.212 2.772 1.842 H19 9KU 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 9KU C20 C19 SING N N 1 9KU C20 C21 SING N N 2 9KU O1 C1 DOUB N N 3 9KU C19 N2 SING N N 4 9KU C21 C6 SING N N 5 9KU C1 N3 SING N N 6 9KU C1 C2 SING N N 7 9KU N3 C5 SING N N 8 9KU O2 C2 SING N N 9 9KU C2 C3 DOUB N N 10 9KU C5 C6 SING N N 11 9KU C5 N1 DOUB N N 12 9KU N2 C6 SING N N 13 9KU N2 C7 SING N N 14 9KU C8 C7 SING N N 15 9KU C8 O5 SING N N 16 9KU C3 N1 SING N N 17 9KU C3 C4 SING N N 18 9KU C7 O6 DOUB N N 19 9KU O4 C4 DOUB N N 20 9KU C4 O3 SING N N 21 9KU O5 C9 SING N N 22 9KU C10 C9 DOUB Y N 23 9KU C10 C11 SING Y N 24 9KU C9 C14 SING Y N 25 9KU C11 C12 DOUB Y N 26 9KU C14 C15 DOUB Y N 27 9KU C14 C13 SING Y N 28 9KU C15 C16 SING Y N 29 9KU C12 C13 SING Y N 30 9KU C13 C18 DOUB Y N 31 9KU C16 C17 DOUB Y N 32 9KU C18 C17 SING Y N 33 9KU C10 H1 SING N N 34 9KU C11 H2 SING N N 35 9KU C12 H3 SING N N 36 9KU C15 H4 SING N N 37 9KU C16 H5 SING N N 38 9KU C17 H6 SING N N 39 9KU C18 H7 SING N N 40 9KU C19 H8 SING N N 41 9KU C19 H9 SING N N 42 9KU C20 H10 SING N N 43 9KU C20 H11 SING N N 44 9KU C21 H12 SING N N 45 9KU C21 H13 SING N N 46 9KU C6 H14 SING N N 47 9KU C8 H15 SING N N 48 9KU C8 H16 SING N N 49 9KU N3 H17 SING N N 50 9KU O2 H18 SING N N 51 9KU O3 H19 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 9KU SMILES ACDLabs 12.01 "C4(NC(C1CCCN1C(=O)COc3cccc2ccccc23)=NC(=C4O)C(O)=O)=O" 9KU InChI InChI 1.03 "InChI=1S/C21H19N3O6/c25-16(11-30-15-9-3-6-12-5-1-2-7-13(12)15)24-10-4-8-14(24)19-22-17(21(28)29)18(26)20(27)23-19/h1-3,5-7,9,14,26H,4,8,10-11H2,(H,28,29)(H,22,23,27)/t14-/m0/s1" 9KU InChIKey InChI 1.03 SALSCRPWDRUSQC-AWEZNQCLSA-N 9KU SMILES_CANONICAL CACTVS 3.385 "OC(=O)C1=C(O)C(=O)NC(=N1)[C@@H]2CCCN2C(=O)COc3cccc4ccccc34" 9KU SMILES CACTVS 3.385 "OC(=O)C1=C(O)C(=O)NC(=N1)[CH]2CCCN2C(=O)COc3cccc4ccccc34" 9KU SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "c1ccc2c(c1)cccc2OCC(=O)N3CCC[C@H]3C4=NC(=C(C(=O)N4)O)C(=O)O" 9KU SMILES "OpenEye OEToolkits" 2.0.6 "c1ccc2c(c1)cccc2OCC(=O)N3CCCC3C4=NC(=C(C(=O)N4)O)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 9KU "SYSTEMATIC NAME" ACDLabs 12.01 "5-hydroxy-2-[(2S)-1-{[(naphthalen-1-yl)oxy]acetyl}pyrrolidin-2-yl]-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid" 9KU "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.6 "2-[(2~{S})-1-(2-naphthalen-1-yloxyethanoyl)pyrrolidin-2-yl]-5-oxidanyl-6-oxidanylidene-1~{H}-pyrimidine-4-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 9KU "Create component" 2017-07-11 RCSB 9KU "Initial release" 2018-01-03 RCSB 9KU "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 9KU _pdbx_chem_comp_synonyms.name SRI-29789 _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##