data_BTD
# 
_chem_comp.id                                    BTD 
_chem_comp.name                                  5-BROMOTHIENYLDEOXYURIDINE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C13 H13 Br N2 O5 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_chem_comp.pdbx_modified_date                    2008-10-14 
_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                        389.222 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     BTD 
_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        1KI4 
_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 
BTD "O5'"  O5*  O  0 1 N N N 17.544 93.923 44.130 0.705  -2.572 6.324  "O5'"  BTD 1  
BTD "C5'"  C5*  C  0 1 N N N 16.949 94.605 45.235 0.456  -1.166 6.374  "C5'"  BTD 2  
BTD "C4'"  C4*  C  0 1 N N R 17.641 95.850 45.389 1.158  -0.481 5.200  "C4'"  BTD 3  
BTD "O4'"  O4*  O  0 1 N N N 19.002 95.472 45.705 0.611  -0.938 3.944  "O4'"  BTD 4  
BTD "C1'"  C1*  C  0 1 N N R 19.871 95.986 44.741 0.923  0.063  2.961  "C1'"  BTD 5  
BTD N1     N1   N  0 1 N N N 20.795 94.802 44.536 -0.158 0.149  1.977  N1     BTD 6  
BTD C6     C6   C  0 1 N N N 20.374 93.475 44.392 0.120  -0.066 0.656  C6     BTD 7  
BTD C2     C2   C  0 1 N N N 22.129 95.150 44.555 -1.403 0.433  2.391  C2     BTD 8  
BTD O2     O2   O  0 1 N N N 22.519 96.311 44.679 -1.604 0.618  3.576  O2     BTD 9  
BTD N3     N3   N  0 1 N N N 23.006 94.158 44.428 -2.433 0.529  1.532  N3     BTD 10 
BTD C4     C4   C  0 1 N N N 22.674 92.849 44.243 -2.239 0.329  0.211  C4     BTD 11 
BTD O4     O4   O  0 1 N N N 23.645 92.135 44.106 -3.168 0.410  -0.571 O4     BTD 12 
BTD C5     C5   C  0 1 N N N 21.249 92.461 44.222 -0.885 0.012  -0.263 C5     BTD 13 
BTD C55    C55  C  0 1 Y N N 20.853 91.109 44.069 -0.618 -0.215 -1.699 C55    BTD 14 
BTD C44    C44  C  0 1 Y N N 19.678 90.551 44.436 -1.144 -1.164 -2.534 C44    BTD 15 
BTD C33    C33  C  0 1 Y N N 19.592 89.215 44.134 -0.744 -1.180 -3.854 C33    BTD 16 
BTD C22    C22  C  0 1 Y N N 20.686 88.658 43.486 0.162  -0.264 -4.281 C22    BTD 17 
BTD S11    S11  S  0 1 Y N N 21.891 89.826 43.226 0.477  0.671  -2.794 S11    BTD 18 
BTD BR     BR   BR 0 0 N N N 21.308 87.024 42.795 0.902  -0.039 -6.006 BR     BTD 19 
BTD "C2'"  C2*  C  0 1 N N N 18.956 96.320 43.660 1.066  1.405  3.705  "C2'"  BTD 20 
BTD "C3'"  C3*  C  0 1 N N S 17.678 96.760 44.274 0.860  1.039  5.197  "C3'"  BTD 21 
BTD "O3'"  O3*  O  0 1 N N N 17.862 97.933 44.922 1.781  1.747  6.028  "O3'"  BTD 22 
BTD "HO5'" *HO5 H  0 0 N N N 17.085 93.097 44.027 0.246  -2.964 7.079  "HO5'" BTD 23 
BTD "H5'1" 1H5* H  0 0 N N N 15.846 94.729 45.128 -0.616 -0.985 6.311  "H5'1" BTD 24 
BTD "H5'2" 2H5* H  0 0 N N N 16.935 93.995 46.168 0.838  -0.762 7.311  "H5'2" BTD 25 
BTD "H4'"  H4*  H  0 1 N N N 17.080 96.428 46.159 2.232  -0.661 5.238  "H4'"  BTD 26 
BTD "H1'"  H1*  H  0 1 N N N 20.500 96.887 44.924 1.859  -0.185 2.462  "H1'"  BTD 27 
BTD H6     H6   H  0 1 N N N 19.302 93.216 44.413 1.127  -0.297 0.342  H6     BTD 28 
BTD HN3    HN3  H  0 1 N N N 23.991 94.416 44.475 -3.320 0.740  1.863  HN3    BTD 29 
BTD H44    H44  H  0 1 N N N 18.875 91.124 44.929 -1.864 -1.881 -2.168 H44    BTD 30 
BTD H33    H33  H  0 1 N N N 18.697 88.624 44.396 -1.144 -1.914 -4.538 H33    BTD 31 
BTD "H2'1" 1H2* H  0 0 N N N 19.377 97.069 42.950 2.062  1.822  3.552  "H2'1" BTD 32 
BTD "H2'2" 2H2* H  0 0 N N N 18.823 95.487 42.930 0.302  2.109  3.374  "H2'2" BTD 33 
BTD "H3'"  H3*  H  0 1 N N N 16.835 96.813 43.545 -0.167 1.232  5.506  "H3'"  BTD 34 
BTD "HO3'" *HO3 H  0 0 N N N 17.886 98.533 44.186 1.599  2.689  5.909  "HO3'" BTD 35 
# 
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 
BTD "O5'" "C5'"  SING N N 1  
BTD "O5'" "HO5'" SING N N 2  
BTD "C5'" "C4'"  SING N N 3  
BTD "C5'" "H5'1" SING N N 4  
BTD "C5'" "H5'2" SING N N 5  
BTD "C4'" "O4'"  SING N N 6  
BTD "C4'" "C3'"  SING N N 7  
BTD "C4'" "H4'"  SING N N 8  
BTD "O4'" "C1'"  SING N N 9  
BTD "C1'" N1     SING N N 10 
BTD "C1'" "C2'"  SING N N 11 
BTD "C1'" "H1'"  SING N N 12 
BTD N1    C6     SING N N 13 
BTD N1    C2     SING N N 14 
BTD C6    C5     DOUB N N 15 
BTD C6    H6     SING N N 16 
BTD C2    O2     DOUB N N 17 
BTD C2    N3     SING N N 18 
BTD N3    C4     SING N N 19 
BTD N3    HN3    SING N N 20 
BTD C4    O4     DOUB N N 21 
BTD C4    C5     SING N N 22 
BTD C5    C55    SING N N 23 
BTD C55   C44    DOUB Y N 24 
BTD C55   S11    SING Y N 25 
BTD C44   C33    SING Y N 26 
BTD C44   H44    SING N N 27 
BTD C33   C22    DOUB Y N 28 
BTD C33   H33    SING N N 29 
BTD C22   S11    SING Y N 30 
BTD C22   BR     SING N N 31 
BTD "C2'" "C3'"  SING N N 32 
BTD "C2'" "H2'1" SING N N 33 
BTD "C2'" "H2'2" SING N N 34 
BTD "C3'" "O3'"  SING N N 35 
BTD "C3'" "H3'"  SING N N 36 
BTD "O3'" "HO3'" SING N N 37 
# 
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 
BTD SMILES           ACDLabs              10.04 Brc3sc(C=1C(=O)NC(=O)N(C=1)C2OC(CO)C(O)C2)cc3                                                                                                           
BTD InChI            InChI                1.02b InChI=1/C13H13BrN2O5S/c14-10-2-1-9(22-10)6-4-16(13(20)15-12(6)19)11-3-7(18)8(5-17)21-11/h1-2,4,7-8,11,17-18H,3,5H2,(H,15,19,20)/t7-,8+,11+/m0/s1/f/h15H 
BTD InChIKey         InChI                1.02b IGUZFFOBAZCVRK-RHPRRFKKDH                                                                                                                               
BTD SMILES_CANONICAL CACTVS               3.341 OC[C@H]1O[C@H](C[C@@H]1O)N2C=C(C(=O)NC2=O)c3sc(Br)cc3                                                                                                   
BTD SMILES           CACTVS               3.341 OC[CH]1O[CH](C[CH]1O)N2C=C(C(=O)NC2=O)c3sc(Br)cc3                                                                                                       
BTD SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(sc1C2=CN(C(=O)NC2=O)[C@H]3C[C@@H]([C@H](O3)CO)O)Br                                                                                                 
BTD SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(sc1C2=CN(C(=O)NC2=O)C3CC(C(O3)CO)O)Br                                                                                                              
# 
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 
BTD "SYSTEMATIC NAME" ACDLabs              10.04 "5-(5-bromothiophen-2-yl)-2'-deoxyuridine"                                                         
BTD "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 5-(5-bromothiophen-2-yl)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione 
# 
