data_BRU
# 
_chem_comp.id                                    BRU 
_chem_comp.name                                  "5-BROMO-2'-DEOXYURIDINE-5'-MONOPHOSPHATE" 
_chem_comp.type                                  "DNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C9 H12 Br N2 O8 P" 
_chem_comp.mon_nstd_parent_comp_id               DU 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_chem_comp.pdbx_modified_date                    2009-01-07 
_chem_comp.pdbx_ambiguous_flag                   N 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         UBR
_chem_comp.formula_weight                        387.078 
_chem_comp.one_letter_code                       U 
_chem_comp.three_letter_code                     BRU 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1A35 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
BRU N1     N1   N  0 1 N N N 24.773 -2.005 -6.345 0.527  -0.166 1.257  N1     BRU 1  
BRU C2     C2   C  0 1 N N N 24.466 -0.683 -6.589 -0.000 -1.399 1.160  C2     BRU 2  
BRU N3     N3   N  0 1 N N N 25.536 0.169  -6.539 -0.650 -1.958 2.198  N3     BRU 3  
BRU C4     C4   C  0 1 N N N 26.848 -0.153 -6.277 -0.792 -1.280 3.355  C4     BRU 4  
BRU C5     C5   C  0 1 N N N 27.111 -1.570 -6.058 -0.245 0.021  3.470  C5     BRU 5  
BRU C6     C6   C  0 1 N N N 26.071 -2.414 -6.112 0.405  0.555  2.414  C6     BRU 6  
BRU O2     O2   O  0 1 N N N 23.328 -0.293 -6.840 0.119  -2.023 0.123  O2     BRU 7  
BRU O4     O4   O  0 1 N N N 27.691 0.737  -6.216 -1.384 -1.783 4.293  O4     BRU 8  
BRU BR     BR   BR 0 0 N N N 29.072 -2.194 -5.660 -0.427 0.998  5.078  BR     BRU 9  
BRU "C1'"  C1*  C  0 1 N N R 23.655 -2.960 -6.316 1.234  0.413  0.112  "C1'"  BRU 10 
BRU "C2'"  C2*  C  0 1 N N N 23.863 -4.254 -7.080 2.445  -0.464 -0.271 "C2'"  BRU 11 
BRU "C3'"  C3*  C  0 1 N N S 22.871 -5.167 -6.379 2.484  -0.397 -1.815 "C3'"  BRU 12 
BRU "C4'"  C4*  C  0 1 N N R 22.914 -4.690 -4.930 1.290  0.512  -2.183 "C4'"  BRU 13 
BRU "O3'"  O3*  O  0 1 N N N 21.561 -4.951 -6.869 3.711  0.183  -2.260 "O3'"  BRU 14 
BRU "O4'"  O4*  O  0 1 N N N 23.450 -3.347 -4.966 0.388  0.407  -1.058 "O4'"  BRU 15 
BRU "C5'"  C5*  C  0 1 N N N 23.764 -5.574 -4.060 0.609  0.016  -3.460 "C5'"  BRU 16 
BRU "O5'"  O5*  O  0 1 N N N 24.924 -5.989 -4.791 -0.532 0.830  -3.737 "O5'"  BRU 17 
BRU P      P    P  0 1 N N N 25.889 -7.090 -4.180 -1.197 0.256  -5.086 P      BRU 18 
BRU OP1    O1P  O  0 1 N N N 25.074 -8.325 -3.956 -1.595 -1.154 -4.878 OP1    BRU 19 
BRU OP2    O2P  O  0 1 N N N 27.148 -7.154 -4.999 -2.496 1.131  -5.459 OP2    BRU 20 
BRU OP3    O3P  O  0 1 N Y N 26.206 -6.481 -2.735 -0.129 0.340  -6.289 OP3    BRU 21 
BRU HN3    HN3  H  0 1 N N N 25.333 1.152  -6.716 -1.021 -2.850 2.112  HN3    BRU 22 
BRU H6     H6   H  0 1 N N N 26.291 -3.483 -5.959 0.829  1.546  2.483  H6     BRU 23 
BRU "H1'"  H1*  H  0 1 N N N 22.805 -2.422 -6.798 1.558  1.428  0.341  "H1'"  BRU 24 
BRU "H2'"  1H2* H  0 1 N N N 23.747 -4.181 -8.186 2.294  -1.491 0.061  "H2'"  BRU 25 
BRU "H2''" 2H2* H  0 0 N N N 24.913 -4.625 -7.116 3.363  -0.056 0.151  "H2''" BRU 26 
BRU "H3'"  H3*  H  0 1 N N N 23.118 -6.244 -6.522 2.354  -1.390 -2.244 "H3'"  BRU 27 
BRU "H4'"  H4*  H  0 1 N N N 21.892 -4.721 -4.484 1.624  1.542  -2.307 "H4'"  BRU 28 
BRU "HO3'" *HO3 H  0 0 N Y N 20.940 -5.521 -6.430 4.420  -0.410 -1.977 "HO3'" BRU 29 
BRU "H5'"  1H5* H  0 1 N N N 24.027 -5.085 -3.092 1.309  0.077  -4.293 "H5'"  BRU 30 
BRU "H5''" 2H5* H  0 0 N N N 23.191 -6.439 -3.651 0.293  -1.017 -3.326 "H5''" BRU 31 
BRU HOP2   2HOP H  0 0 N N N 27.725 -7.813 -4.633 -2.862 0.754  -6.271 HOP2   BRU 32 
BRU HOP3   3HOP H  0 0 N N N 26.783 -7.140 -2.369 0.102  1.273  -6.391 HOP3   BRU 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 
BRU N1    C2     SING N N 1  
BRU N1    C6     SING N N 2  
BRU N1    "C1'"  SING N N 3  
BRU C2    N3     SING N N 4  
BRU C2    O2     DOUB N N 5  
BRU N3    C4     SING N N 6  
BRU N3    HN3    SING N N 7  
BRU C4    C5     SING N N 8  
BRU C4    O4     DOUB N N 9  
BRU C5    C6     DOUB N N 10 
BRU C5    BR     SING N N 11 
BRU C6    H6     SING N N 12 
BRU "C1'" "C2'"  SING N N 13 
BRU "C1'" "O4'"  SING N N 14 
BRU "C1'" "H1'"  SING N N 15 
BRU "C2'" "C3'"  SING N N 16 
BRU "C2'" "H2'"  SING N N 17 
BRU "C2'" "H2''" SING N N 18 
BRU "C3'" "C4'"  SING N N 19 
BRU "C3'" "O3'"  SING N N 20 
BRU "C3'" "H3'"  SING N N 21 
BRU "C4'" "O4'"  SING N N 22 
BRU "C4'" "C5'"  SING N N 23 
BRU "C4'" "H4'"  SING N N 24 
BRU "O3'" "HO3'" SING N N 25 
BRU "C5'" "O5'"  SING N N 26 
BRU "C5'" "H5'"  SING N N 27 
BRU "C5'" "H5''" SING N N 28 
BRU "O5'" P      SING N N 29 
BRU P     OP1    DOUB N N 30 
BRU P     OP2    SING N N 31 
BRU P     OP3    SING N N 32 
BRU OP2   HOP2   SING N N 33 
BRU OP3   HOP3   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 
BRU SMILES           ACDLabs              10.04 "BrC=1C(=O)NC(=O)N(C=1)C2OC(C(O)C2)COP(=O)(O)O"                                                                                                           
BRU InChI            InChI                1.02b "InChI=1/C9H12BrN2O8P/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18)/t5-,6+,7+/m0/s1/f/h11,16-17H" 
BRU InChIKey         InChI                1.02b LHLHVDBXXZVYJT-DUSMYMCLDB                                                                                                                                 
BRU SMILES_CANONICAL CACTVS               3.341 "O[C@H]1C[C@@H](O[C@@H]1CO[P](O)(O)=O)N2C=C(Br)C(=O)NC2=O"                                                                                                
BRU SMILES           CACTVS               3.341 "O[CH]1C[CH](O[CH]1CO[P](O)(O)=O)N2C=C(Br)C(=O)NC2=O"                                                                                                     
BRU SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)Br)COP(=O)(O)O)O"                                                                                                 
BRU SMILES           "OpenEye OEToolkits" 1.5.0 "C1C(C(OC1N2C=C(C(=O)NC2=O)Br)COP(=O)(O)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 
BRU "SYSTEMATIC NAME" ACDLabs              10.04 
;5-bromo-2'-deoxyuridine 5'-(dihydrogen phosphate)
;
BRU "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,5R)-5-(5-bromo-2,4-dioxo-pyrimidin-1-yl)-3-hydroxy-oxolan-2-yl]methyl dihydrogen phosphate" 
# 
