data_8BR
# 
_chem_comp.id                                    8BR 
_chem_comp.name                                  "8-BROMO-ADENOSINE-5'-MONOPHOSPHATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C10 H13 Br N5 O7 P" 
_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                        426.117 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     8BR 
_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        5RHN 
_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 
8BR P      P    P  0 1 N N N 11.602 6.898  60.933 0.463  -0.519 -5.012 P      8BR 1  
8BR O1P    O1P  O  0 1 N N N 10.589 5.781  60.815 1.539  0.480  -4.828 O1P    8BR 2  
8BR O2P    O2P  O  0 1 N N N 12.817 6.817  60.042 1.082  -1.864 -5.644 O2P    8BR 3  
8BR O3P    O3P  O  0 1 N N N 11.861 7.412  62.316 -0.656 0.074  -6.006 O3P    8BR 4  
8BR "O5'"  O5*  O  0 1 N N N 10.784 8.131  60.288 -0.206 -0.854 -3.588 "O5'"  8BR 5  
8BR "C5'"  C5*  C  0 1 N N N 10.437 8.096  58.866 -0.735 0.372  -3.080 "C5'"  8BR 6  
8BR "C4'"  C4*  C  0 1 N N R 9.253  9.005  58.668 -1.390 0.121  -1.720 "C4'"  8BR 7  
8BR "O4'"  O4*  O  0 1 N N N 9.363  9.746  57.411 -0.413 -0.363 -0.774 "O4'"  8BR 8  
8BR "C3'"  C3*  C  0 1 N N S 7.874  8.278  58.593 -1.901 1.447  -1.115 "C3'"  8BR 9  
8BR "O3'"  O3*  O  0 1 N N N 6.968  8.815  59.617 -3.301 1.602  -1.358 "O3'"  8BR 10 
8BR "C2'"  C2*  C  0 1 N N R 7.324  8.607  57.190 -1.627 1.300  0.399  "C2'"  8BR 11 
8BR "O2'"  O2*  O  0 1 N N N 5.936  8.709  57.084 -2.849 1.361  1.138  "O2'"  8BR 12 
8BR "C1'"  C1*  C  0 1 N N R 8.087  9.902  56.897 -0.979 -0.096 0.527  "C1'"  8BR 13 
8BR N9     N9   N  0 1 Y N N 8.200  10.237 55.451 0.072  -0.079 1.547  N9     8BR 14 
8BR C8     C8   C  0 1 Y N N 8.916  9.524  54.463 -0.081 -0.372 2.870  C8     8BR 15 
8BR BR8    BR8  BR 0 0 N N N 9.734  7.866  54.699 -1.711 -0.871 3.688  BR8    8BR 16 
8BR N7     N7   N  0 1 Y N N 8.971  10.184 53.300 1.060  -0.257 3.486  N7     8BR 17 
8BR C5     C5   C  0 1 Y N N 8.351  11.352 53.568 2.016  0.108  2.599  C5     8BR 18 
8BR C6     C6   C  0 1 Y N N 8.043  12.424 52.751 3.391  0.382  2.686  C6     8BR 19 
8BR N6     N6   N  0 1 N N N 8.358  12.441 51.438 4.058  0.282  3.895  N6     8BR 20 
8BR N1     N1   N  0 1 Y N N 7.384  13.469 53.285 4.039  0.733  1.579  N1     8BR 21 
8BR C2     C2   C  0 1 Y N N 6.947  13.444 54.600 3.411  0.831  0.422  C2     8BR 22 
8BR N3     N3   N  0 1 Y N N 7.377  12.578 55.464 2.123  0.590  0.294  N3     8BR 23 
8BR C4     C4   C  0 1 Y N N 7.922  11.455 54.940 1.393  0.233  1.345  C4     8BR 24 
8BR HOP2   2HOP H  0 0 N N N 13.453 7.518  60.116 1.473  -1.619 -6.495 HOP2   8BR 25 
8BR HOP3   3HOP H  0 0 N N N 12.497 8.113  62.390 -1.336 -0.606 -6.098 HOP3   8BR 26 
8BR "H5'1" 1H5* H  0 0 N N N 11.296 8.349  58.202 -1.479 0.761  -3.775 "H5'1" 8BR 27 
8BR "H5'2" 2H5* H  0 0 N N N 10.260 7.062  58.486 0.071  1.096  -2.968 "H5'2" 8BR 28 
8BR "H4'"  H4*  H  0 1 N N N 9.278  9.659  59.570 -2.209 -0.590 -1.820 "H4'"  8BR 29 
8BR "H3'"  H3*  H  0 1 N N N 7.968  7.180  58.765 -1.348 2.293  -1.524 "H3'"  8BR 30 
8BR "HO3'" *HO3 H  0 0 N N N 6.128  8.372  59.571 -3.563 2.443  -0.959 "HO3'" 8BR 31 
8BR "H2'"  H2*  H  0 1 N N N 7.485  7.791  56.447 -0.937 2.072  0.739  "H2'"  8BR 32 
8BR "HO2'" *HO2 H  0 0 N N N 5.597  8.911  56.219 -3.233 2.232  0.969  "HO2'" 8BR 33 
8BR "H1'"  H1*  H  0 1 N N N 7.517  10.739 57.363 -1.733 -0.843 0.773  "H1'"  8BR 34 
8BR HN61   1HN6 H  0 0 N N N 8.130  13.231 50.835 5.009  0.469  3.941  HN61   8BR 35 
8BR HN62   2HN6 H  0 0 N N N 7.960  11.603 51.013 3.574  0.028  4.696  HN62   8BR 36 
8BR H2     H2   H  0 1 N N N 6.205  14.163 54.985 3.975  1.120  -0.452 H2     8BR 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 
8BR P     O1P    DOUB N N 1  
8BR P     O2P    SING N N 2  
8BR P     O3P    SING N N 3  
8BR P     "O5'"  SING N N 4  
8BR O2P   HOP2   SING N N 5  
8BR O3P   HOP3   SING N N 6  
8BR "O5'" "C5'"  SING N N 7  
8BR "C5'" "C4'"  SING N N 8  
8BR "C5'" "H5'1" SING N N 9  
8BR "C5'" "H5'2" SING N N 10 
8BR "C4'" "O4'"  SING N N 11 
8BR "C4'" "C3'"  SING N N 12 
8BR "C4'" "H4'"  SING N N 13 
8BR "O4'" "C1'"  SING N N 14 
8BR "C3'" "O3'"  SING N N 15 
8BR "C3'" "C2'"  SING N N 16 
8BR "C3'" "H3'"  SING N N 17 
8BR "O3'" "HO3'" SING N N 18 
8BR "C2'" "O2'"  SING N N 19 
8BR "C2'" "C1'"  SING N N 20 
8BR "C2'" "H2'"  SING N N 21 
8BR "O2'" "HO2'" SING N N 22 
8BR "C1'" N9     SING N N 23 
8BR "C1'" "H1'"  SING N N 24 
8BR N9    C8     SING Y N 25 
8BR N9    C4     SING Y N 26 
8BR C8    BR8    SING N N 27 
8BR C8    N7     DOUB Y N 28 
8BR N7    C5     SING Y N 29 
8BR C5    C6     SING Y N 30 
8BR C5    C4     DOUB Y N 31 
8BR C6    N6     SING N N 32 
8BR C6    N1     DOUB Y N 33 
8BR N6    HN61   SING N N 34 
8BR N6    HN62   SING N N 35 
8BR N1    C2     SING Y N 36 
8BR C2    N3     DOUB Y N 37 
8BR C2    H2     SING N N 38 
8BR N3    C4     SING Y 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 
8BR SMILES           ACDLabs              10.04 Brc2nc1c(ncnc1n2C3OC(C(O)C3O)COP(=O)(O)O)N                                                                                                                                      
8BR InChI            InChI                1.02b InChI=1/C10H13BrN5O7P/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-6(18)5(17)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,17-18H,1H2,(H2,12,13,14)(H2,19,20,21)/t3-,5-,6-,9-/m1/s1/f/h19-20H,12H2 
8BR InChIKey         InChI                1.02b DNPIJKNXFSPNNY-XCXSYHRODQ                                                                                                                                                       
8BR SMILES_CANONICAL CACTVS               3.341 Nc1ncnc2n([C@@H]3O[C@H](CO[P](O)(O)=O)[C@@H](O)[C@H]3O)c(Br)nc12                                                                                                                
8BR SMILES           CACTVS               3.341 Nc1ncnc2n([CH]3O[CH](CO[P](O)(O)=O)[CH](O)[CH]3O)c(Br)nc12                                                                                                                      
8BR SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(c(n2)Br)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)N                                                                                                            
8BR SMILES           "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(c(n2)Br)C3C(C(C(O3)COP(=O)(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 
8BR "SYSTEMATIC NAME" ACDLabs              10.04 
;8-bromoadenosine 5'-(dihydrogen phosphate)
;
8BR "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-5-(6-amino-8-bromo-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methyl dihydrogen phosphate" 
# 
