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 
# 
