data_8BU # _chem_comp.id 8BU _chem_comp.name "[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methoxy-[(S)-fluoranyl-[oxidanyl(phosphonooxy)phosphoryl]methyl]phosphinic acid" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C11 H17 F N5 O12 P3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2017-06-06 _chem_comp.pdbx_modified_date 2018-02-02 _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 523.199 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 8BU _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 5XP5 _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 8BU PG P1 P 0 1 N N N 14.010 -5.054 11.356 -7.129 -1.308 0.646 PG 8BU 1 8BU O1G O1 O 0 1 N N N 13.408 -6.019 10.362 -7.960 -0.176 0.180 O1G 8BU 2 8BU O2G O2 O 0 1 N N N 14.119 -3.638 10.844 -7.615 -1.763 2.112 O2G 8BU 3 8BU O3G O3 O 0 1 N N N 13.392 -5.149 12.732 -7.280 -2.542 -0.377 O3G 8BU 4 8BU PB P2 P 0 1 N N N 16.513 -4.831 12.614 -4.649 0.057 -0.234 PB 8BU 5 8BU O1B O4 O 0 1 N N N 15.698 -3.988 13.569 -5.216 1.421 -0.330 O1B 8BU 6 8BU O2B O5 O 0 1 N N N 17.598 -4.117 11.841 -4.574 -0.597 -1.704 O2B 8BU 7 8BU O3B O6 O 0 1 N N N 15.523 -5.550 11.578 -5.586 -0.850 0.710 O3B 8BU 8 8BU PA P3 P 0 1 N N N 18.724 -5.945 13.822 -1.911 1.171 -0.591 PA 8BU 9 8BU O1A O7 O 0 1 N N N 18.930 -6.828 15.036 -2.478 2.534 -0.687 O1A 8BU 10 8BU O2A O8 O 0 1 N N N 19.012 -4.463 13.941 -1.837 0.516 -2.061 O2A 8BU 11 8BU N9 N1 N 0 1 Y N N 23.063 -3.450 11.829 4.608 -0.394 -0.043 N9 8BU 12 8BU C8 C1 C 0 1 Y N N 21.944 -2.871 11.370 4.265 -1.150 -1.125 C8 8BU 13 8BU N7 N2 N 0 1 Y N N 22.238 -1.699 10.769 5.198 -2.024 -1.369 N7 8BU 14 8BU C5 C2 C 0 1 Y N N 23.551 -1.474 10.814 6.196 -1.885 -0.464 C5 8BU 15 8BU C6 C3 C 0 1 Y N N 24.438 -0.390 10.337 7.423 -2.531 -0.238 C6 8BU 16 8BU N6 N3 N 0 1 N N N 23.953 0.679 9.692 7.837 -3.569 -1.054 N6 8BU 17 8BU N1 N4 N 0 1 Y N N 25.733 -0.551 10.591 8.177 -2.121 0.777 N1 8BU 18 8BU C2 C4 C 0 1 Y N N 26.166 -1.637 11.239 7.790 -1.131 1.560 C2 8BU 19 8BU N3 N5 N 0 1 Y N N 25.430 -2.654 11.699 6.649 -0.497 1.387 N3 8BU 20 8BU C4 C5 C 0 1 Y N N 24.104 -2.650 11.527 5.829 -0.837 0.398 C4 8BU 21 8BU C01 C6 C 0 1 N N S 17.166 -6.060 13.438 -2.973 0.144 0.477 C01 8BU 22 8BU "O5'" O9 O 0 1 N N N 19.542 -6.530 12.562 -0.431 1.248 0.037 "O5'" 8BU 23 8BU "C5'" C7 C 0 1 N N N 20.625 -7.427 12.871 0.606 2.063 -0.512 "C5'" 8BU 24 8BU "C4'" C8 C 0 1 N N R 21.935 -6.671 13.090 1.878 1.902 0.324 "C4'" 8BU 25 8BU "C3'" C9 C 0 1 N N S 21.932 -5.819 14.399 2.975 2.867 -0.176 "C3'" 8BU 26 8BU "O3'" O10 O 0 1 N N N 22.583 -6.505 15.480 3.021 4.039 0.641 "O3'" 8BU 27 8BU "C2'" C10 C 0 1 N N R 22.684 -4.533 14.019 4.283 2.056 -0.032 "C2'" 8BU 28 8BU "O2'" O11 O 0 1 N N N 23.789 -4.261 14.884 5.175 2.702 0.878 "O2'" 8BU 29 8BU "C1'" C11 C 0 1 N N R 23.163 -4.754 12.553 3.820 0.696 0.537 "C1'" 8BU 30 8BU "O4'" O12 O 0 1 N N N 22.361 -5.802 11.965 2.436 0.582 0.141 O4* 8BU 31 8BU F01 F1 F 0 1 N N N 17.048 -6.876 12.905 -2.437 -1.145 0.567 F01 8BU 32 8BU H1 H1 H 0 1 N N N 13.780 -3.594 9.958 -8.536 -2.052 2.148 H1 8BU 33 8BU H2 H2 H 0 1 N N N 12.716 -5.816 12.731 -6.761 -3.320 -0.133 H2 8BU 34 8BU H4 H4 H 0 1 N N N 17.607 -3.198 12.082 -4.212 -1.493 -1.717 H4 8BU 35 8BU H6 H6 H 0 1 N N N 19.305 -4.267 14.823 -1.474 -0.380 -2.074 H6 8BU 36 8BU H7 H7 H 0 1 N N N 20.951 -3.283 11.467 3.354 -1.040 -1.694 H7 8BU 37 8BU H8 H8 H 0 1 N N N 24.704 1.294 9.453 7.278 -3.859 -1.792 H8 8BU 38 8BU H9 H9 H 0 1 N N N 23.487 0.382 8.858 8.686 -4.007 -0.888 H9 8BU 39 8BU H10 H10 H 0 1 N N N 27.230 -1.700 11.410 8.433 -0.831 2.374 H10 8BU 40 8BU H11 H11 H 0 1 N N N 16.638 -6.061 14.403 -3.023 0.587 1.472 H11 8BU 41 8BU H12 H12 H 0 1 N N N 20.377 -7.984 13.786 0.805 1.755 -1.539 H12 8BU 42 8BU H13 H13 H 0 1 N N N 20.754 -8.132 12.036 0.293 3.107 -0.500 H13 8BU 43 8BU H14 H14 H 0 1 N N N 22.717 -7.433 13.223 1.664 2.082 1.377 H14 8BU 44 8BU H15 H15 H 0 1 N N N 20.894 -5.570 14.663 2.803 3.136 -1.218 H15 8BU 45 8BU H16 H16 H 0 1 N N N 22.564 -5.961 16.258 3.693 4.680 0.372 H16 8BU 46 8BU H17 H17 H 0 1 N N N 21.975 -3.692 14.031 4.759 1.924 -1.004 H17 8BU 47 8BU H18 H18 H 0 1 N N N 24.218 -3.460 14.608 5.450 3.586 0.598 H18 8BU 48 8BU H19 H19 H 0 1 N N N 24.217 -5.067 12.581 3.907 0.690 1.623 H19 8BU 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 8BU PG O1G DOUB N N 1 8BU PG O2G SING N N 2 8BU PG O3G SING N N 3 8BU PG O3B SING N N 4 8BU PB O1B DOUB N N 5 8BU PB O2B SING N N 6 8BU PB O3B SING N N 7 8BU PB C01 SING N N 8 8BU PA O1A DOUB N N 9 8BU PA O2A SING N N 10 8BU PA C01 SING N N 11 8BU PA "O5'" SING N N 12 8BU N9 C8 SING Y N 13 8BU N9 C4 SING Y N 14 8BU N9 "C1'" SING N N 15 8BU C8 N7 DOUB Y N 16 8BU N7 C5 SING Y N 17 8BU C5 C6 DOUB Y N 18 8BU C5 C4 SING Y N 19 8BU C6 N6 SING N N 20 8BU C6 N1 SING Y N 21 8BU N1 C2 DOUB Y N 22 8BU C2 N3 SING Y N 23 8BU N3 C4 DOUB Y N 24 8BU C01 F01 SING N N 25 8BU "O5'" "C5'" SING N N 26 8BU "C5'" "C4'" SING N N 27 8BU "C4'" "C3'" SING N N 28 8BU "C4'" "O4'" SING N N 29 8BU "C3'" "O3'" SING N N 30 8BU "C3'" "C2'" SING N N 31 8BU "C2'" "O2'" SING N N 32 8BU "C2'" "C1'" SING N N 33 8BU "C1'" "O4'" SING N N 34 8BU O2G H1 SING N N 35 8BU O3G H2 SING N N 36 8BU O2B H4 SING N N 37 8BU O2A H6 SING N N 38 8BU C8 H7 SING N N 39 8BU N6 H8 SING N N 40 8BU N6 H9 SING N N 41 8BU C2 H10 SING N N 42 8BU C01 H11 SING N N 43 8BU "C5'" H12 SING N N 44 8BU "C5'" H13 SING N N 45 8BU "C4'" H14 SING N N 46 8BU "C3'" H15 SING N N 47 8BU "O3'" H16 SING N N 48 8BU "C2'" H17 SING N N 49 8BU "O2'" H18 SING N N 50 8BU "C1'" H19 SING N N 51 # 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 8BU InChI InChI 1.03 "InChI=1S/C11H17FN5O12P3/c12-11(31(22,23)29-32(24,25)26)30(20,21)27-1-4-6(18)7(19)10(28-4)17-3-16-5-8(13)14-2-15-9(5)17/h2-4,6-7,10-11,18-19H,1H2,(H,20,21)(H,22,23)(H2,13,14,15)(H2,24,25,26)/t4-,6-,7-,10-,11+/m1/s1" 8BU InChIKey InChI 1.03 XKSDFFGXFUDVBD-MYGYUQIRSA-N 8BU SMILES_CANONICAL CACTVS 3.385 "Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P](O)(=O)[C@H](F)[P](O)(=O)O[P](O)(O)=O)[C@@H](O)[C@H]3O" 8BU SMILES CACTVS 3.385 "Nc1ncnc2n(cnc12)[CH]3O[CH](CO[P](O)(=O)[CH](F)[P](O)(=O)O[P](O)(O)=O)[CH](O)[CH]3O" 8BU SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)([C@H](F)P(=O)(O)OP(=O)(O)O)O)O)O)N" 8BU SMILES "OpenEye OEToolkits" 2.0.6 "c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COP(=O)(C(F)P(=O)(O)OP(=O)(O)O)O)O)O)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 8BU "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.6 "[(2~{R},3~{S},4~{R},5~{R})-5-(6-aminopurin-9-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methoxy-[(~{S})-fluoranyl-[oxidanyl(phosphonooxy)phosphoryl]methyl]phosphinic 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 8BU "Create component" 2017-06-07 PDBJ 8BU "Initial release" 2018-02-07 RCSB #