data_GBR
# 
_chem_comp.id                                    GBR 
_chem_comp.name                                  "5'-O-[(R)-{[(S)-[(R)-bromo(phosphono)methyl](hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]-2'-deoxyguanosine" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C11 H17 Br N5 O12 P3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2009-09-14 
_chem_comp.pdbx_modified_date                    2011-06-04 
_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                        584.104 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GBR 
_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        3JPQ 
_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 
GBR N1     N1     N  0 1 N N N 9.736  8.849  8.120  -8.419 2.101  0.154  N1     GBR 1  
GBR C2     C2     C  0 1 N N N 8.476  9.010  7.571  -7.913 1.551  1.294  C2     GBR 2  
GBR N2     N2     N  0 1 N N N 8.418  9.545  6.339  -8.590 1.727  2.475  N2     GBR 3  
GBR N3     N3     N  0 1 N N N 7.352  8.669  8.198  -6.797 0.858  1.295  N3     GBR 4  
GBR C4     C4     C  0 1 Y N N 7.586  8.158  9.434  -6.104 0.661  0.167  C4     GBR 5  
GBR C5     C5     C  0 1 Y N N 8.796  7.964  10.075 -6.571 1.200  -1.036 C5     GBR 6  
GBR C6     C6     C  0 1 N N N 10.000 8.317  9.387  -7.774 1.945  -1.023 C6     GBR 7  
GBR O6     O6     O  0 1 N N N 11.172 8.193  9.773  -8.218 2.432  -2.048 O6     GBR 8  
GBR N7     N7     N  0 1 Y N N 8.604  7.420  11.336 -5.688 0.852  -2.003 N7     GBR 9  
GBR C8     C8     C  0 1 Y N N 7.309  7.284  11.433 -4.729 0.148  -1.477 C8     GBR 10 
GBR N9     N9     N  0 1 Y N N 6.636  7.689  10.302 -4.943 0.003  -0.137 N9     GBR 11 
GBR PA     PA     P  0 1 N N N 4.994  5.159  14.675 1.471  -1.851 -0.730 PA     GBR 12 
GBR PB     PB     P  0 1 N N N 3.969  2.770  13.812 4.157  -0.707 -0.214 PB     GBR 13 
GBR BRB    BRB    BR 0 0 N N N 5.007  -0.200 14.131 3.889  2.364  0.060  BRB    GBR 14 
GBR PG     PG     P  0 1 N N N 3.996  1.366  16.601 6.532  0.865  0.650  PG     GBR 15 
GBR "C1'"  "C1'"  C  0 1 N N R 5.204  7.592  10.034 -4.087 -0.723 0.804  "C1'"  GBR 16 
GBR O1A    O1A    O  0 1 N N N 3.726  5.169  15.837 1.258  -1.529 -2.293 O1A    GBR 17 
GBR O1B    O1B    O  0 1 N N N 4.011  2.149  12.209 4.585  -0.507 -1.753 O1B    GBR 18 
GBR O1G    O1G    O  0 1 N N N 3.269  2.856  17.058 6.960  1.065  -0.889 O1G    GBR 19 
GBR "C2'"  "C2'"  C  0 1 N N N 4.807  6.174  9.625  -4.609 -2.162 0.985  "C2'"  GBR 20 
GBR O2A    O2A    O  0 1 N N N 6.403  5.181  15.140 1.957  -3.240 -0.573 O2A    GBR 21 
GBR O2B    O2B    O  0 1 N N N 2.655  3.182  14.368 4.781  -1.941 0.315  O2B    GBR 22 
GBR O2G    O2G    O  0 1 N N N 5.092  0.621  17.697 7.028  2.130  1.514  O2G    GBR 23 
GBR "C3'"  "C3'"  C  0 1 N N S 4.435  5.565  10.961 -3.418 -3.054 0.559  "C3'"  GBR 24 
GBR "O3'"  "O3'"  O  0 1 N N N 3.563  4.445  10.779 -3.282 -4.175 1.435  "O3'"  GBR 25 
GBR O3A    O3A    O  0 1 N N N 4.808  4.014  13.708 2.555  -0.831 -0.115 O3A    GBR 26 
GBR C3B    C3B    C  0 1 N N R 4.793  1.574  14.963 4.718  0.725  0.763  C3B    GBR 27 
GBR O3G    O3G    O  0 1 N N N 2.862  0.419  16.494 7.156  -0.368 1.180  O3G    GBR 28 
GBR "C4'"  "C4'"  C  0 1 N N R 3.708  6.734  11.613 -2.217 -2.086 0.710  "C4'"  GBR 29 
GBR "O4'"  "O4'"  O  0 1 N N N 4.496  7.886  11.239 -2.752 -0.816 0.279  "O4'"  GBR 30 
GBR "C5'"  "C5'"  C  0 1 N N N 3.526  6.677  13.113 -1.060 -2.518 -0.194 "C5'"  GBR 31 
GBR "O5'"  "O5'"  O  0 1 N N N 4.776  6.454  13.769 0.072  -1.681 0.049  "O5'"  GBR 32 
GBR HN1    HN1    H  0 1 N N N 10.519 9.135  7.568  -9.247 2.605  0.188  HN1    GBR 33 
GBR HN2    HN2    H  0 1 N N N 7.532  9.686  5.896  -9.415 2.236  2.491  HN2    GBR 34 
GBR HN2A   HN2A   H  0 0 N N N 9.260  9.802  5.865  -8.242 1.341  3.295  HN2A   GBR 35 
GBR H8     H8     H  0 1 N N N 6.816  6.894  12.311 -3.889 -0.261 -2.019 H8     GBR 36 
GBR "H1'"  "H1'"  H  0 1 N N N 4.963  8.293  9.221  -4.074 -0.210 1.766  "H1'"  GBR 37 
GBR "H2'"  "H2'"  H  0 1 N N N 3.966  6.166  8.916  -4.870 -2.345 2.027  "H2'"  GBR 38 
GBR "H2'A" "H2'A" H  0 0 N N N 5.633  5.635  9.138  -5.469 -2.339 0.339  "H2'A" GBR 39 
GBR "H3'"  "H3'"  H  0 1 N N N 5.281  5.176  11.546 -3.527 -3.382 -0.474 "H3'"  GBR 40 
GBR "HO3'" "HO3'" H  0 0 N N N 3.340  4.076  11.625 -4.050 -4.763 1.444  "HO3'" GBR 41 
GBR H3B    H3B    H  0 1 N N N 5.771  2.041  15.153 4.428  0.590  1.805  H3B    GBR 42 
GBR "H4'"  "H4'"  H  0 1 N N N 2.666  6.743  11.261 -1.894 -2.034 1.750  "H4'"  GBR 43 
GBR "H5'"  "H5'"  H  0 1 N N N 3.105  7.632  13.459 -0.799 -3.554 0.021  "H5'"  GBR 44 
GBR "H5'A" "H5'A" H  0 0 N N N 2.840  5.853  13.360 -1.362 -2.428 -1.238 "H5'A" GBR 45 
GBR H14    H14    H  0 1 N N N 3.082  4.508  15.610 0.940  -0.633 -2.470 H14    GBR 46 
GBR H15    H15    H  0 1 N N N 3.132  2.143  11.848 4.212  0.283  -2.166 H15    GBR 47 
GBR H16    H16    H  0 1 N N N 2.329  2.739  17.137 6.587  1.856  -1.301 H16    GBR 48 
GBR H17    H17    H  0 1 N N N 4.736  -0.212 17.984 7.985  2.266  1.499  H17    GBR 49 
# 
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 
GBR N1    C2     SING N N 1  
GBR N1    C6     SING N N 2  
GBR N1    HN1    SING N N 3  
GBR C2    N2     SING N N 4  
GBR C2    N3     DOUB N N 5  
GBR N2    HN2    SING N N 6  
GBR N2    HN2A   SING N N 7  
GBR N3    C4     SING N N 8  
GBR C4    C5     DOUB Y N 9  
GBR C4    N9     SING Y N 10 
GBR C5    C6     SING N N 11 
GBR C5    N7     SING Y N 12 
GBR C6    O6     DOUB N N 13 
GBR N7    C8     DOUB Y N 14 
GBR C8    N9     SING Y N 15 
GBR C8    H8     SING N N 16 
GBR N9    "C1'"  SING N N 17 
GBR PA    O1A    SING N N 18 
GBR PA    O2A    DOUB N N 19 
GBR PA    O3A    SING N N 20 
GBR PA    "O5'"  SING N N 21 
GBR PB    O1B    SING N N 22 
GBR PB    O2B    DOUB N N 23 
GBR PB    O3A    SING N N 24 
GBR PB    C3B    SING N N 25 
GBR BRB   C3B    SING N N 26 
GBR PG    O1G    SING N N 27 
GBR PG    O2G    SING N N 28 
GBR PG    C3B    SING N N 29 
GBR PG    O3G    DOUB N N 30 
GBR "C1'" "C2'"  SING N N 31 
GBR "C1'" "O4'"  SING N N 32 
GBR "C1'" "H1'"  SING N N 33 
GBR "C2'" "C3'"  SING N N 34 
GBR "C2'" "H2'"  SING N N 35 
GBR "C2'" "H2'A" SING N N 36 
GBR "C3'" "O3'"  SING N N 37 
GBR "C3'" "C4'"  SING N N 38 
GBR "C3'" "H3'"  SING N N 39 
GBR "O3'" "HO3'" SING N N 40 
GBR C3B   H3B    SING N N 41 
GBR "C4'" "O4'"  SING N N 42 
GBR "C4'" "C5'"  SING N N 43 
GBR "C4'" "H4'"  SING N N 44 
GBR "C5'" "O5'"  SING N N 45 
GBR "C5'" "H5'"  SING N N 46 
GBR "C5'" "H5'A" SING N N 47 
GBR O1A   H14    SING N N 48 
GBR O1B   H15    SING N N 49 
GBR O1G   H16    SING N N 50 
GBR O2G   H17    SING N N 51 
# 
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 
GBR SMILES           ACDLabs              11.02 "O=P(O)(O)C(Br)P(=O)(O)OP(=O)(O)OCC3OC(n2cnc1c2N=C(N)NC1=O)CC3O" 
GBR SMILES_CANONICAL CACTVS               3.352 "NC1=Nc2n(cnc2C(=O)N1)[C@H]3C[C@H](O)[C@@H](CO[P](O)(=O)O[P](O)(=O)[C@H](Br)[P](O)(O)=O)O3" 
GBR SMILES           CACTVS               3.352 "NC1=Nc2n(cnc2C(=O)N1)[CH]3C[CH](O)[CH](CO[P](O)(=O)O[P](O)(=O)[CH](Br)[P](O)(O)=O)O3" 
GBR SMILES_CANONICAL "OpenEye OEToolkits" 1.7.0 "c1nc2c(n1[C@H]3C[C@@H]([C@H](O3)CO[P@@](=O)(O)O[P@](=O)([C@@H](P(=O)(O)O)Br)O)O)N=C(NC2=O)N" 
GBR SMILES           "OpenEye OEToolkits" 1.7.0 "c1nc2c(n1C3CC(C(O3)COP(=O)(O)OP(=O)(C(P(=O)(O)O)Br)O)O)N=C(NC2=O)N" 
GBR InChI            InChI                1.03  
"InChI=1S/C11H17BrN5O12P3/c12-10(30(20,21)22)31(23,24)29-32(25,26)27-2-5-4(18)1-6(28-5)17-3-14-7-8(17)15-11(13)16-9(7)19/h3-6,10,18H,1-2H2,(H,23,24)(H,25,26)(H2,20,21,22)(H3,13,15,16,19)/t4-,5+,6+,10+/m0/s1" 
GBR InChIKey         InChI                1.03  NBJGMAKPACFZHS-AVAJSQPUSA-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 
GBR "SYSTEMATIC NAME" ACDLabs              11.02 "5'-O-[(R)-{[(S)-[(R)-bromo(phosphono)methyl](hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]-2'-deoxyguanosine"                                                
GBR "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.6.1 "[(R)-[[[(2R,3S,5R)-5-(2-azanyl-6-oxo-1H-purin-9-yl)-3-hydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]-bromo-methyl]phosphonic acid" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
GBR "Create component"  2009-09-14 RCSB 
GBR "Modify descriptor" 2011-06-04 RCSB 
# 
