data_BUP # _chem_comp.id BUP _chem_comp.name ;5-bromouridine 5'-(tetrahydrogen triphosphate) ; _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C9 H14 Br N2 O15 P3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2010-06-08 _chem_comp.pdbx_modified_date 2011-06-10 _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 563.037 _chem_comp.one_letter_code ? _chem_comp.three_letter_code BUP _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 3N6N _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site PDBJ # 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 BUP BR BR BR 0 0 N N N 0.564 -48.304 7.117 -6.736 -2.422 -0.709 BR BUP 1 BUP C1 C1 C 0 1 N N N 1.740 -47.259 7.126 -5.478 -1.266 0.099 C1 BUP 2 BUP N1 N1 N 0 1 N N N 4.247 -46.722 7.467 -4.453 -0.376 2.063 N1 BUP 3 BUP O1 O1 O 0 1 N N N 3.408 -49.043 7.759 -6.072 -1.898 2.216 O1 BUP 4 BUP P1 P1 P 0 1 N N N -1.360 -41.503 10.096 2.653 1.418 0.807 P1 BUP 5 BUP C2 C2 C 0 1 N N N 1.466 -45.815 6.804 -4.681 -0.483 -0.660 C2 BUP 6 BUP N2 N2 N 0 1 N N N 2.563 -44.835 6.806 -3.776 0.349 -0.058 N2 BUP 7 BUP O2 O2 O 0 1 N N N 5.031 -44.363 7.157 -2.858 1.136 1.797 O2 BUP 8 BUP P2 P2 P 0 1 N N N -1.230 -38.691 9.314 5.111 -0.229 0.632 P2 BUP 9 BUP C3 C3 C 0 1 N N N 3.976 -45.286 7.146 -3.672 0.394 1.283 C3 BUP 10 BUP O3 O3 O 0 1 N N N 1.431 -42.839 7.511 -1.524 1.000 -0.534 O3 BUP 11 BUP P3 P3 P 0 1 N N N -3.043 -37.579 11.286 7.003 -1.872 -0.951 P3 BUP 12 BUP C4 C4 C 0 1 N N N 3.147 -47.701 7.459 -5.361 -1.205 1.510 C4 BUP 13 BUP O4 O4 O 0 1 N N N 2.476 -42.384 4.326 -4.235 3.215 -1.337 O4 BUP 14 BUP C5 C5 C 0 1 N N S 0.318 -42.582 5.395 -1.811 3.339 -0.986 C5 BUP 15 BUP O5 O5 O 0 1 N N N 0.034 -41.531 4.498 -1.915 3.894 -2.299 O5 BUP 16 BUP C6 C6 C 0 1 N N R 1.663 -43.212 5.125 -3.153 2.696 -0.561 C6 BUP 17 BUP O6 O6 O 0 1 N N N -0.753 -42.497 8.914 1.309 1.426 -0.078 O6 BUP 18 BUP C7 C7 C 0 1 N N R 2.311 -43.422 6.500 -2.911 1.198 -0.881 C7 BUP 19 BUP O7 O7 O 0 1 N N N -0.588 -40.032 10.051 3.571 0.167 0.378 O7 BUP 20 BUP C8 C8 C 0 1 N N R 0.399 -42.055 6.831 -0.810 2.167 -0.975 C8 BUP 21 BUP O8 O8 O 0 1 N N N -1.097 -42.196 11.575 2.269 1.293 2.365 O8 BUP 22 BUP C9 C9 C 0 1 N N N -0.955 -42.222 7.545 0.336 2.471 -0.008 C9 BUP 23 BUP O9 O9 O 0 1 N N N -2.800 -41.335 9.901 3.399 2.677 0.583 O9 BUP 24 BUP O10 O10 O 0 1 N N N -2.765 -38.396 9.868 5.573 -1.314 -0.464 O10 BUP 25 BUP O11 O11 O 0 1 N N N -1.263 -38.909 7.673 5.267 -0.857 2.107 O11 BUP 26 BUP O12 O12 O 0 1 N N N -0.375 -37.539 9.610 5.957 0.979 0.518 O12 BUP 27 BUP O13 O13 O 0 1 N N N -3.732 -36.117 10.940 7.533 -2.975 0.095 O13 BUP 28 BUP O14 O14 O 0 1 N N N -1.625 -37.342 12.102 6.849 -2.543 -2.407 O14 BUP 29 BUP O15 O15 O 0 1 N N N -3.958 -38.354 12.126 7.970 -0.755 -1.023 O15 BUP 30 BUP HN1 HN1 H 0 1 N N N 5.177 -47.017 7.687 -4.365 -0.331 3.028 HN1 BUP 31 BUP H2 H2 H 0 1 N N N 0.461 -45.497 6.571 -4.758 -0.513 -1.737 H2 BUP 32 BUP HO4 HO4 H 0 1 N N N 3.312 -42.810 4.176 -4.368 4.167 -1.240 HO4 BUP 33 BUP H5 H5 H 0 1 N N N -0.492 -43.314 5.261 -1.512 4.105 -0.271 H5 BUP 34 BUP HO5 HO5 H 0 1 N N N -0.818 -41.163 4.701 -2.574 4.598 -2.377 HO5 BUP 35 BUP H6 H6 H 0 1 N N N 1.545 -44.156 4.573 -3.335 2.842 0.503 H6 BUP 36 BUP H7 H7 H 0 1 N N N 3.294 -42.929 6.495 -3.075 0.998 -1.940 H7 BUP 37 BUP H8 H8 H 0 1 N N N 0.645 -40.983 6.841 -0.418 2.004 -1.979 H8 BUP 38 BUP HO8 HO8 H 0 1 N N N -1.930 -42.349 12.006 1.778 0.489 2.586 HO8 BUP 39 BUP H9 H9 H 0 1 N N N -1.507 -43.055 7.086 -0.053 2.537 1.008 H9 BUP 40 BUP H9A H9A H 0 1 N N N -1.535 -41.293 7.444 0.801 3.418 -0.282 H9A BUP 41 BUP HO11 HO11 H 0 0 N N N -0.724 -38.248 7.254 4.739 -1.653 2.253 HO11 BUP 42 BUP HO13 HO13 H 0 0 N N N -4.586 -36.063 11.352 6.947 -3.738 0.193 HO13 BUP 43 BUP HO14 HO14 H 0 0 N N N -1.678 -37.754 12.956 7.673 -2.902 -2.763 HO14 BUP 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 BUP BR C1 SING N N 1 BUP C1 C2 DOUB N N 2 BUP C1 C4 SING N N 3 BUP N1 C3 SING N N 4 BUP N1 C4 SING N N 5 BUP O1 C4 DOUB N N 6 BUP P1 O6 SING N N 7 BUP P1 O7 SING N N 8 BUP P1 O8 SING N N 9 BUP P1 O9 DOUB N N 10 BUP C2 N2 SING N N 11 BUP N2 C3 SING N N 12 BUP N2 C7 SING N N 13 BUP O2 C3 DOUB N N 14 BUP P2 O7 SING N N 15 BUP P2 O10 SING N N 16 BUP P2 O11 SING N N 17 BUP P2 O12 DOUB N N 18 BUP O3 C7 SING N N 19 BUP O3 C8 SING N N 20 BUP P3 O10 SING N N 21 BUP P3 O13 SING N N 22 BUP P3 O14 SING N N 23 BUP P3 O15 DOUB N N 24 BUP O4 C6 SING N N 25 BUP C5 O5 SING N N 26 BUP C5 C6 SING N N 27 BUP C5 C8 SING N N 28 BUP C6 C7 SING N N 29 BUP O6 C9 SING N N 30 BUP C8 C9 SING N N 31 BUP N1 HN1 SING N N 32 BUP C2 H2 SING N N 33 BUP O4 HO4 SING N N 34 BUP C5 H5 SING N N 35 BUP O5 HO5 SING N N 36 BUP C6 H6 SING N N 37 BUP C7 H7 SING N N 38 BUP C8 H8 SING N N 39 BUP O8 HO8 SING N N 40 BUP C9 H9 SING N N 41 BUP C9 H9A SING N N 42 BUP O11 HO11 SING N N 43 BUP O13 HO13 SING N N 44 BUP O14 HO14 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 BUP SMILES ACDLabs 12.01 "O=P(O)(O)OP(=O)(O)OP(=O)(O)OCC2OC(N1C(=O)NC(=O)C(Br)=C1)C(O)C2O" BUP SMILES_CANONICAL CACTVS 3.370 "O[C@H]1[C@@H](O)[C@@H](O[C@@H]1CO[P](O)(=O)O[P](O)(=O)O[P](O)(O)=O)N2C=C(Br)C(=O)NC2=O" BUP SMILES CACTVS 3.370 "O[CH]1[CH](O)[CH](O[CH]1CO[P](O)(=O)O[P](O)(=O)O[P](O)(O)=O)N2C=C(Br)C(=O)NC2=O" BUP SMILES_CANONICAL "OpenEye OEToolkits" 1.7.0 "C1=C(C(=O)NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO[P@@](=O)(O)O[P@@](=O)(O)OP(=O)(O)O)O)O)Br" BUP SMILES "OpenEye OEToolkits" 1.7.0 "C1=C(C(=O)NC(=O)N1C2C(C(C(O2)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O)O)Br" BUP InChI InChI 1.03 "InChI=1S/C9H14BrN2O15P3/c10-3-1-12(9(16)11-7(3)15)8-6(14)5(13)4(25-8)2-24-29(20,21)27-30(22,23)26-28(17,18)19/h1,4-6,8,13-14H,2H2,(H,20,21)(H,22,23)(H,11,15,16)(H2,17,18,19)/t4-,5-,6-,8-/m1/s1" BUP InChIKey InChI 1.03 IWFHOSULCAJGRM-UAKXSSHOSA-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 BUP "SYSTEMATIC NAME" ACDLabs 12.01 ;5-bromouridine 5'-(tetrahydrogen triphosphate) ; BUP "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.0 "[[(2R,3S,4R,5R)-5-(5-bromo-2,4-dioxo-pyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl] phosphono hydrogen phosphate" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site BUP "Create component" 2010-06-08 PDBJ BUP "Modify descriptor" 2011-06-04 RCSB #