data_BGM
# 
_chem_comp.id                                    BGM 
_chem_comp.name                                  "8-BROMO-2'-DEOXYGUANOSINE-5'-MONOPHOSPHATE" 
_chem_comp.type                                  "DNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C10 H13 Br N5 O7 P" 
_chem_comp.mon_nstd_parent_comp_id               DG 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2002-11-21 
_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                         ? 
_chem_comp.formula_weight                        426.117 
_chem_comp.one_letter_code                       G 
_chem_comp.three_letter_code                     BGM 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   Y 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1N7A 
_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 
BGM P      P    P  0 1 N N N 11.870 17.189 57.614 1.884  -1.918 -4.898 P      BGM 1  
BGM OP1    O1P  O  0 1 N N N 12.970 18.062 58.071 2.848  -1.580 -5.997 OP1    BGM 2  
BGM OP2    O2P  O  0 1 N N N 10.861 17.778 56.725 0.345  -1.506 -5.177 OP2    BGM 3  
BGM "O5'"  O5*  O  0 1 N N N 12.533 15.896 56.982 2.211  -1.232 -3.468 "O5'"  BGM 4  
BGM "C5'"  C5*  C  0 1 N N N 11.692 14.763 56.713 1.348  -1.500 -2.377 "C5'"  BGM 5  
BGM "C4'"  C4*  C  0 1 N N R 12.607 13.719 56.107 2.156  -1.432 -1.088 "C4'"  BGM 6  
BGM "O4'"  O4*  O  0 1 N N N 11.998 12.424 56.238 2.678  -0.093 -0.958 "O4'"  BGM 7  
BGM "C1'"  C1*  C  0 1 N N R 11.998 11.748 54.968 2.101  0.516  0.211  "C1'"  BGM 8  
BGM N9     N9   N  0 1 Y N N 10.821 10.901 54.966 1.818  1.923  -0.049 N9     BGM 9  
BGM C8     C8   C  0 1 Y N N 9.480  11.209 55.074 1.884  2.962  0.852  C8     BGM 10 
BGM N7     N7   N  0 1 Y N N 8.682  10.178 55.088 1.567  4.121  0.309  N7     BGM 11 
BGM C5     C5   C  0 1 Y N N 9.561  9.109  54.981 1.288  3.811  -0.989 C5     BGM 12 
BGM C4     C4   C  0 1 Y N N 10.863 9.534  54.910 1.433  2.468  -1.242 C4     BGM 13 
BGM N3     N3   N  0 1 N N N 11.976 8.784  54.817 1.247  1.795  -2.398 N3     BGM 14 
BGM C2     C2   C  0 1 N N N 11.714 7.492  54.786 0.875  2.572  -3.392 C2     BGM 15 
BGM N2     N2   N  0 1 N N N 12.732 6.642  54.717 0.635  2.081  -4.649 N2     BGM 16 
BGM N1     N1   N  0 1 N N N 10.453 6.956  54.851 0.695  3.968  -3.243 N1     BGM 17 
BGM C6     C6   C  0 1 N N N 9.304  7.724  54.955 0.883  4.686  -2.054 C6     BGM 18 
BGM O6     O6   O  0 1 N N N 8.187  7.153  55.010 0.727  5.893  -1.922 O6     BGM 19 
BGM "C2'"  C2*  C  0 1 N N N 12.016 12.862 53.945 0.878  -0.312 0.578  "C2'"  BGM 20 
BGM "C3'"  C3*  C  0 1 N N S 12.962 13.861 54.630 1.309  -1.697 0.152  "C3'"  BGM 21 
BGM "O3'"  O3*  O  0 1 N N N 14.348 13.554 54.447 2.127  -2.250 1.180  "O3'"  BGM 22 
BGM OP3    O3P  O  0 1 N Y N ?      ?      ?      1.788  -3.490 -4.532 OP3    BGM 23 
BGM BR     BR   BR 0 0 N N N ?      ?      ?      2.374  2.788  2.685  BR     BGM 24 
BGM HOP2   2HOP H  0 0 N N N 10.153 17.216 56.431 -0.064 -1.754 -6.033 HOP2   BGM 25 
BGM "H5'"  1H5* H  0 1 N N N 11.126 14.402 57.603 0.551  -0.756 -2.359 "H5'"  BGM 26 
BGM "H5''" 2H5* H  0 0 N N N 10.804 15.002 56.082 0.917  -2.495 -2.497 "H5''" BGM 27 
BGM "H4'"  H4*  H  0 1 N N N 13.555 13.860 56.675 3.008  -2.117 -1.157 "H4'"  BGM 28 
BGM "H1'"  H1*  H  0 1 N N N 12.860 11.076 54.746 2.853  0.503  1.007  "H1'"  BGM 29 
BGM H21    1H2  H  0 1 N N N 12.529 5.642  54.693 0.993  2.585  -5.428 H21    BGM 30 
BGM H22    2H2  H  0 1 N N N 13.375 6.831  55.485 0.113  1.240  -4.735 H22    BGM 31 
BGM H1     H1   H  0 1 N N N 10.365 5.940  54.820 0.406  4.493  -4.064 H1     BGM 32 
BGM "H2'"  1H2* H  0 1 N N N 12.300 12.560 52.909 0.008  0.008  -0.009 "H2'"  BGM 33 
BGM "H2''" 2H2* H  0 0 N N N 11.017 13.265 53.654 0.635  -0.225 1.641  "H2''" BGM 34 
BGM "H3'"  H3*  H  0 1 N N N 12.833 14.885 54.208 0.475  -2.383 -0.018 "H3'"  BGM 35 
BGM "HO3'" H3T  H  0 0 N Y N 14.569 13.642 53.527 2.928  -1.706 1.218  "HO3'" BGM 36 
BGM HOP3   3HOP H  0 0 N N N -0.707 -0.561 -0.294 1.686  -4.141 -5.258 HOP3   BGM 37 
# 
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 
BGM P     OP1    DOUB N N 1  
BGM P     OP2    SING N N 2  
BGM P     "O5'"  SING N N 3  
BGM P     OP3    SING N N 4  
BGM OP2   HOP2   SING N N 5  
BGM "O5'" "C5'"  SING N N 6  
BGM "C5'" "C4'"  SING N N 7  
BGM "C5'" "H5'"  SING N N 8  
BGM "C5'" "H5''" SING N N 9  
BGM "C4'" "O4'"  SING N N 10 
BGM "C4'" "C3'"  SING N N 11 
BGM "C4'" "H4'"  SING N N 12 
BGM "O4'" "C1'"  SING N N 13 
BGM "C1'" N9     SING N N 14 
BGM "C1'" "C2'"  SING N N 15 
BGM "C1'" "H1'"  SING N N 16 
BGM N9    C8     SING Y N 17 
BGM N9    C4     SING Y N 18 
BGM C8    N7     DOUB Y N 19 
BGM C8    BR     SING N N 20 
BGM N7    C5     SING Y N 21 
BGM C5    C4     DOUB Y N 22 
BGM C5    C6     SING N N 23 
BGM C4    N3     SING N N 24 
BGM N3    C2     DOUB N N 25 
BGM C2    N2     SING N N 26 
BGM C2    N1     SING N N 27 
BGM N2    H21    SING N N 28 
BGM N2    H22    SING N N 29 
BGM N1    C6     SING N N 30 
BGM N1    H1     SING N N 31 
BGM C6    O6     DOUB N N 32 
BGM "C2'" "C3'"  SING N N 33 
BGM "C2'" "H2'"  SING N N 34 
BGM "C2'" "H2''" SING N N 35 
BGM "C3'" "O3'"  SING N N 36 
BGM "C3'" "H3'"  SING N N 37 
BGM "O3'" "HO3'" SING N N 38 
BGM OP3   HOP3   SING N N 39 
# 
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 
BGM SMILES           ACDLabs              10.04 "O=C1c2nc(Br)n(c2N=C(N)N1)C3OC(C(O)C3)COP(=O)(O)O"                                                                                                                           
BGM InChI            InChI                1.02b "InChI=1/C10H13BrN5O7P/c11-9-13-6-7(14-10(12)15-8(6)18)16(9)5-1-3(17)4(23-5)2-22-24(19,20)21/h3-5,17H,1-2H2,(H2,19,20,21)(H3,12,14,15,18)/t3-,4+,5+/m0/s1/f/h15,19-20H,12H2" 
BGM InChIKey         InChI                1.02b KUFMHNJQBUZBPA-RCBPBRIGDB                                                                                                                                                    
BGM SMILES_CANONICAL CACTVS               3.341 "NC1=Nc2n([C@H]3C[C@H](O)[C@@H](CO[P](O)(O)=O)O3)c(Br)nc2C(=O)N1"                                                                                                            
BGM SMILES           CACTVS               3.341 "NC1=Nc2n([CH]3C[CH](O)[CH](CO[P](O)(O)=O)O3)c(Br)nc2C(=O)N1"                                                                                                                
BGM SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C1[C@@H]([C@H](O[C@H]1n2c3c(nc2Br)C(=O)NC(=N3)N)COP(=O)(O)O)O"                                                                                                              
BGM SMILES           "OpenEye OEToolkits" 1.5.0 "C1C(C(OC1n2c3c(nc2Br)C(=O)NC(=N3)N)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 
BGM "SYSTEMATIC NAME" ACDLabs              10.04 
;8-bromo-2'-deoxyguanosine 5'-(dihydrogen phosphate)
;
BGM "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,5R)-5-(2-amino-8-bromo-6-oxo-1H-purin-9-yl)-3-hydroxy-oxolan-2-yl]methyl dihydrogen phosphate" 
# 
