data_8BA
# 
_chem_comp.id                                    8BA 
_chem_comp.name                                  "8-bromo-deoxyadenosine-5'-monophosphate" 
_chem_comp.type                                  "DNA linking" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C10 H12 Br N5 O6 P" 
_chem_comp.mon_nstd_parent_comp_id               DA 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2013-07-16 
_chem_comp.pdbx_modified_date                    2018-09-25 
_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                        409.110 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     8BA 
_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        4I29 
_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 
8BA P     P1  P  0 1 N N N 12.303 -20.530 -25.421 -4.701 -0.638 0.952  P     8BA 1  
8BA "O5'" O1  O  0 1 N N N 11.552 -19.191 -25.624 -3.380 0.281  0.903  "O5'" 8BA 2  
8BA "C5'" C1  C  0 1 N N N 11.392 -18.738 -26.954 -2.790 0.730  -0.319 "C5'" 8BA 3  
8BA "C4'" C2  C  0 1 N N R 10.433 -17.591 -27.122 -1.555 1.577  -0.007 "C4'" 8BA 4  
8BA "O4'" O2  O  0 1 N N N 9.101  -18.022 -27.011 -0.520 0.767  0.592  "O4'" 8BA 5  
8BA "C3'" C3  C  0 1 N N S 10.577 -16.485 -26.122 -0.900 2.090  -1.315 "C3'" 8BA 6  
8BA "O3'" O3  O  0 1 N N N 11.516 -15.522 -26.537 -1.507 3.310  -1.745 "O3'" 8BA 7  
8BA "C2'" C4  C  0 1 N N N 9.219  -15.874 -26.094 0.565  2.327  -0.874 "C2'" 8BA 8  
8BA "C1'" C5  C  0 1 N N R 8.302  -16.922 -26.685 0.724  1.458  0.388  "C1'" 8BA 9  
8BA N9    N1  N  0 1 Y N N 7.287  -17.302 -25.709 1.805  0.489  0.193  N9    8BA 10 
8BA C8    C6  C  0 1 Y N N 6.038  -17.582 -25.936 1.755  -0.630 -0.585 C8    8BA 11 
8BA N7    N2  N  0 1 Y N N 5.279  -17.887 -24.932 2.893  -1.262 -0.529 N7    8BA 12 
8BA C5    C7  C  0 1 Y N N 6.103  -17.815 -23.935 3.742  -0.590 0.286  C5    8BA 13 
8BA C6    C8  C  0 1 Y N N 5.943  -18.039 -22.522 5.065  -0.789 0.714  C6    8BA 14 
8BA N1    N3  N  0 1 Y N N 6.997  -17.900 -21.763 5.603  0.100  1.542  N1    8BA 15 
8BA C2    C9  C  0 1 Y N N 8.179  -17.556 -22.272 4.917  1.149  1.960  C2    8BA 16 
8BA N3    N4  N  0 1 Y N N 8.403  -17.321 -23.558 3.676  1.375  1.586  N3    8BA 17 
8BA C4    C10 C  0 1 Y N N 7.411  -17.433 -24.420 3.057  0.544  0.754  C4    8BA 18 
8BA OP1   O4  O  0 1 N N N 12.595 -20.683 -24.043 -5.889 0.189  0.643  OP1   8BA 19 
8BA OP2   O5  O  0 1 N N N 13.331 -20.512 -26.423 -4.583 -1.726 -0.045 OP2   8BA 20 
8BA N6    N5  N  0 1 N N N 4.845  -18.359 -22.099 5.792  -1.885 0.282  N6    8BA 21 
8BA BR    BR1 BR 0 0 N N N 5.235  -17.514 -27.726 0.255  -1.183 -1.596 BR    8BA 22 
8BA O1    O6  O  0 1 N Y N 11.259 -21.603 -25.844 -4.858 -1.273 2.423  O1    8BA 23 
8BA H1    H1  H  0 1 N N N 11.027 -19.580 -27.560 -2.497 -0.131 -0.919 H1    8BA 24 
8BA H2    H2  H  0 1 N N N 12.376 -18.418 -27.327 -3.512 1.330  -0.872 H2    8BA 25 
8BA H3    H3  H  0 1 N N N 10.591 -17.164 -28.123 -1.816 2.410  0.646  H3    8BA 26 
8BA H4    H4  H  0 1 N N N 10.831 -16.897 -25.134 -0.953 1.334  -2.099 H4    8BA 27 
8BA H5    H5  H  0 1 N N N 11.581 -14.838 -25.880 -1.132 3.671  -2.559 H5    8BA 28 
8BA H6    H6  H  0 1 N N N 9.196  -14.956 -26.699 1.255  2.000  -1.652 H6    8BA 29 
8BA H7    H7  H  0 1 N N N 8.922  -15.640 -25.061 0.727  3.379  -0.638 H7    8BA 30 
8BA H8    H8  H  0 1 N N N 7.819  -16.512 -27.584 0.942  2.090  1.249  H8    8BA 31 
8BA H9    H9  H  0 1 N N N 9.012  -17.462 -21.591 5.393  1.847  2.633  H9    8BA 32 
8BA H11   H11 H  0 1 N N N 4.894  -18.490 -21.109 5.388  -2.527 -0.323 H11   8BA 33 
8BA H12   H12 H  0 1 N N N 4.185  -17.638 -22.307 6.705  -2.011 0.584  H12   8BA 34 
8BA H13   H13 H  0 1 N N N 11.530 -22.004 -26.662 -5.635 -1.840 2.526  H13   8BA 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 
8BA BR    C8    SING N N 1  
8BA "C4'" "O4'" SING N N 2  
8BA "C4'" "C5'" SING N N 3  
8BA "C4'" "C3'" SING N N 4  
8BA "O4'" "C1'" SING N N 5  
8BA "C5'" "O5'" SING N N 6  
8BA "C1'" "C2'" SING N N 7  
8BA "C1'" N9    SING N N 8  
8BA "O3'" "C3'" SING N N 9  
8BA OP2   P     DOUB N N 10 
8BA "C3'" "C2'" SING N N 11 
8BA C8    N9    SING Y N 12 
8BA C8    N7    DOUB Y N 13 
8BA N9    C4    SING Y N 14 
8BA "O5'" P     SING N N 15 
8BA P     OP1   DOUB N N 16 
8BA N7    C5    SING Y N 17 
8BA C4    C5    DOUB Y N 18 
8BA C4    N3    SING Y N 19 
8BA C5    C6    SING Y N 20 
8BA N3    C2    DOUB Y N 21 
8BA C6    N6    SING N N 22 
8BA C6    N1    DOUB Y N 23 
8BA C2    N1    SING Y N 24 
8BA P     O1    SING N N 25 
8BA "C5'" H1    SING N N 26 
8BA "C5'" H2    SING N N 27 
8BA "C4'" H3    SING N N 28 
8BA "C3'" H4    SING N N 29 
8BA "O3'" H5    SING N N 30 
8BA "C2'" H6    SING N N 31 
8BA "C2'" H7    SING N N 32 
8BA "C1'" H8    SING N N 33 
8BA C2    H9    SING N N 34 
8BA N6    H11   SING N N 35 
8BA N6    H12   SING N N 36 
8BA O1    H13   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 
8BA InChI            InChI                1.03  "InChI=1S/C10H12BrN5O6P/c11-10-15-7-8(12)13-3-14-9(7)16(10)6-1-4(17)5(22-6)2-21-23(18,19)20/h3-6,17H,1-2H2,(H2,12,13,14)(H,18,19,20)/t4-,5+,6+/m0/s1" 
8BA InChIKey         InChI                1.03  MQSWICGOHWVNLL-KVQBGUIXSA-N                                                                                                                           
8BA SMILES_CANONICAL CACTVS               3.385 "Nc1ncnc2n([C@H]3C[C@H](O)[C@@H](CO[P](O)(=O)=O)O3)c(Br)nc12"                                                                                         
8BA SMILES           CACTVS               3.385 "Nc1ncnc2n([CH]3C[CH](O)[CH](CO[P](O)(=O)=O)O3)c(Br)nc12"                                                                                             
8BA SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "c1nc(c2c(n1)n(c(n2)Br)[C@H]3C[C@@H]([C@H](O3)COP(=O)(=O)O)O)N"                                                                                       
8BA SMILES           "OpenEye OEToolkits" 2.0.6 "c1nc(c2c(n1)n(c(n2)Br)C3CC(C(O3)COP(=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 
8BA "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.6 "(2~{R},3~{S},5~{R})-5-(6-azanyl-8-bromanyl-purin-9-yl)-2-[[oxidanyl-bis(oxidanylidene)-$l^{6}-phosphanyl]oxymethyl]oxolan-3-ol" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
8BA "Create component"   2013-07-16 RCSB 
8BA "Initial release"    2013-07-24 RCSB 
8BA "Other modification" 2018-09-25 RCSB 
# 
