data_OI6
# 
_chem_comp.id                                    OI6 
_chem_comp.name                                  
;8-bromoadenosine 5'-diphosphoribose
;
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C15 H22 Br N5 O14 P2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "[[(2~{R},3~{S},4~{R},5~{R})-5-(6-azanyl-8-bromanyl-purin-9-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methoxy-oxidanyl-phosphoryl] [(2~{R},3~{S},4~{R},5~{R})-3,4,5-tris(oxidanyl)oxolan-2-yl]methyl hydrogen phosphate; [[(2R,3S,4R,5R)-5-(6-azanyl-8-bromanyl-purin-9-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methoxy-oxidanyl-phosphoryl] [(2R,3S,4R,5R)-3,4,5-tris(oxidanyl)oxolan-2-yl]methyl hydrogen phosphate; 8Br-ADPR" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2022-09-07 
_chem_comp.pdbx_modified_date                    2024-03-15 
_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                        638.212 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     OI6 
_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        8AZM 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBE 
# 
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.pdbx_backbone_atom_flag 
_chem_comp_atom.pdbx_n_terminal_atom_flag 
_chem_comp_atom.pdbx_c_terminal_atom_flag 
_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 
OI6 "C4'"  C1  C  0 1 N N R N N N -20.251 -6.660  8.142  2.276   -1.668 -1.417 "C4'"  OI6 1  
OI6 "C1'"  C2  C  0 1 N N R N N N -21.796 -4.825  8.059  3.872   -0.026 -1.251 "C1'"  OI6 2  
OI6 C2     C3  C  0 1 Y N N N N N -21.095 -0.538  7.930  6.199   3.783  -1.719 C2     OI6 3  
OI6 C3D    C4  C  0 1 N N S N N N -18.676 -10.793 -0.577 -8.029  1.576  0.828  C3D    OI6 4  
OI6 C4D    C5  C  0 1 N N R N N N -19.276 -10.985 0.542  -6.562  1.357  0.407  C4D    OI6 5  
OI6 C5D    C6  C  0 1 N N N N N N -18.402 -10.701 1.768  -6.205  -0.126 0.521  C5D    OI6 6  
OI6 "C5'"  C7  C  0 1 N N N N N N -19.708 -7.384  6.970  1.303   -2.534 -0.614 "C5'"  OI6 7  
OI6 C4     C8  C  0 1 Y N N N N N -22.005 -2.541  7.199  5.263   1.994  -0.623 C4     OI6 8  
OI6 C6     C9  C  0 1 Y N N N N N -22.457 -0.496  6.067  6.532   3.667  0.562  C6     OI6 9  
OI6 C5     C10 C  0 1 Y N N N N N -22.632 -1.879  6.178  5.785   2.477  0.589  C5     OI6 10 
OI6 C8     C11 C  0 1 Y N N N N N -23.127 -3.984  6.053  4.706   0.648  1.034  C8     OI6 11 
OI6 "C2'"  C12 C  0 1 N N R N N N -22.527 -6.292  8.109  4.683   -1.312 -1.523 "C2'"  OI6 12 
OI6 "C3'"  C13 C  0 1 N N S N N N -21.421 -7.202  8.615  3.609   -2.417 -1.634 "C3'"  OI6 13 
OI6 C1D    C14 C  0 1 N N R N N N -20.571 -9.273  -0.497 -7.464  2.780  -1.181 C1D    OI6 14 
OI6 C2D    C15 C  0 1 N N R N N N -19.124 -9.357  -1.049 -8.689  2.214  -0.419 C2D    OI6 15 
OI6 N9     N1  N  0 1 Y N N N N N -22.330 -3.857  7.111  4.588   0.840  -0.311 N9     OI6 16 
OI6 N3     N2  N  0 1 Y N N N N N -21.230 -1.854  8.067  5.493   2.673  -1.742 N3     OI6 17 
OI6 N1     N3  N  0 1 Y N N N N N -21.680 0.128   6.961  6.710   4.277  -0.605 N1     OI6 18 
OI6 N6     N4  N  0 1 N N N N N N -23.105 0.222   5.003  7.071   4.191  1.724  N6     OI6 19 
OI6 N7     N5  N  0 1 Y N N N N N -23.308 -2.789  5.478  5.409   1.610  1.560  N7     OI6 20 
OI6 O3D    O1  O  0 1 N N N N N N -19.154 -11.804 -1.552 -8.102  2.465  1.944  O3D    OI6 21 
OI6 O5D    O2  O  0 1 N N N N N N -19.157 -11.060 2.884  -4.814  -0.303 0.242  O5D    OI6 22 
OI6 O1B    O3  O  0 1 N N N N N N -19.505 -11.082 5.530  -4.323  -2.385 1.582  O1B    OI6 23 
OI6 O2B    O4  O  0 1 N N N N N N -17.186 -10.541 4.606  -4.695  -2.669 -0.898 O2B    OI6 24 
OI6 O3A    O5  O  0 1 N N N N N N -19.046 -8.807  4.394  -2.509  -1.550 0.039  O3A    OI6 25 
OI6 O1A    O6  O  0 1 N N N N N N -21.602 -9.068  4.033  -1.514  -3.848 -0.283 O1A    OI6 26 
OI6 O2A    O7  O  0 1 N N N N N N -20.580 -6.815  3.806  -0.891  -2.605 1.823  O2A    OI6 27 
OI6 "O5'"  O8  O  0 1 N N N N N N -20.790 -7.870  6.184  0.039   -1.873 -0.525 "O5'"  OI6 28 
OI6 "O4'"  O9  O  0 1 N N N N N N -20.572 -5.066  7.730  2.634   -0.487 -0.667 "O4'"  OI6 29 
OI6 "O2'"  O10 O  0 1 N N N N N N -23.554 -6.293  8.942  5.411   -1.196 -2.747 "O2'"  OI6 30 
OI6 "O3'"  O11 O  0 1 N N N N N N -21.457 -7.133  10.068 3.641   -3.017 -2.931 "O3'"  OI6 31 
OI6 O4D    O12 O  0 1 N N N N N N -20.575 -9.945  0.605  -6.441  1.786  -0.959 O4D    OI6 32 
OI6 O1D    O13 O  0 1 N N N N N N -20.890 -7.916  -0.205 -7.753  2.902  -2.576 O1D    OI6 33 
OI6 O2D    O14 O  0 1 N N N N N N -19.134 -9.231  -2.372 -9.584  3.263  -0.041 O2D    OI6 34 
OI6 PB     P1  P  0 1 N N N N N N -18.720 -10.400 4.426  -4.090  -1.741 0.270  PB     OI6 35 
OI6 PA     P2  P  0 1 N N N N N N -20.561 -8.135  4.541  -1.225  -2.499 0.252  PA     OI6 36 
OI6 BR28   BR1 BR 0 0 N N N N N N -23.966 -5.552  5.334  3.958   -0.800 1.993  BR28   OI6 37 
OI6 "H'4"  H1  H  0 1 N N N N N N -19.488 -6.635  8.934  1.835   -1.392 -2.375 "H'4"  OI6 38 
OI6 "H'1"  H3  H  0 1 N N N N N N -21.863 -4.404  9.073  3.679   0.505  -2.183 "H'1"  OI6 39 
OI6 H2     H4  H  0 1 N N N N N N -20.484 0.001   8.639  6.372   4.309  -2.647 H2     OI6 40 
OI6 "HR'3" H5  H  0 0 N N N N N N -17.579 -10.822 -0.502 -8.504  0.624  1.066  "HR'3" OI6 41 
OI6 "HR'4" H6  H  0 0 N N N N N N -19.678 -12.005 0.629  -5.903  1.947  1.044  "HR'4" OI6 42 
OI6 H5R1   H8  H  0 0 N N N N N N -17.480 -11.299 1.724  -6.420  -0.476 1.530  H5R1   OI6 43 
OI6 H5R2   H9  H  0 0 N N N N N N -18.144 -9.633  1.811  -6.794  -0.698 -0.196 H5R2   OI6 44 
OI6 "H5'1" H10 H  0 0 N N N N N N -19.092 -6.701  6.367  1.175   -3.495 -1.113 "H5'1" OI6 45 
OI6 "H5'2" H11 H  0 0 N N N N N N -19.092 -8.229  7.311  1.701   -2.695 0.387  "H5'2" OI6 46 
OI6 "H'2"  H12 H  0 1 N N N N N N -22.805 -6.576  7.083  5.359   -1.519 -0.693 "H'2"  OI6 47 
OI6 "H'3"  H13 H  0 1 N N N N N N -21.582 -8.231  8.261  3.754   -3.171 -0.860 "H'3"  OI6 48 
OI6 "HR'2" H14 H  0 0 N N N N N N -18.497 -8.602  -0.552 -9.205  1.461  -1.015 "HR'2" OI6 49 
OI6 H61    H15 H  0 1 N N N N N N -22.874 1.193   5.067  6.934   3.737  2.570  H61    OI6 50 
OI6 H62    H16 H  0 1 N N N N N N -22.796 -0.137  4.122  7.585   5.013  1.692  H62    OI6 51 
OI6 HOR3   H17 H  0 0 N N N N N N -18.717 -11.672 -2.385 -9.003  2.639  2.250  HOR3   OI6 52 
OI6 HOB2   H18 H  0 0 N N N N N N -17.004 -11.041 5.393  -4.578  -2.308 -1.787 HOB2   OI6 53 
OI6 HOA2   H19 H  0 0 N N N N N N -21.264 -6.829  3.147  -0.691  -1.756 2.241  HOA2   OI6 54 
OI6 "HO'2" H21 H  0 0 N N N N N N -23.956 -7.154  8.949  5.939   -1.976 -2.966 "HO'2" OI6 55 
OI6 "HO'3" H22 H  0 0 N N N N N N -22.270 -7.510  10.383 4.456   -3.501 -3.120 "HO'3" OI6 56 
OI6 HOR1   H24 H  0 0 N N N N N N -21.776 -7.864  0.133  -7.019  3.252  -3.100 HOR1   OI6 57 
OI6 HOR2   H25 H  0 0 N N N N N N -19.409 -8.352  -2.605 -10.022 3.693  -0.787 HOR2   OI6 58 
OI6 "HR'1" H2  H  0 0 N N N N N N -21.263 -9.681  -1.249 -7.163  3.741  -0.765 "HR'1" OI6 59 
# 
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 
OI6 "C4'" "C5'"  SING N N 1  
OI6 "C4'" "C3'"  SING N N 2  
OI6 "C1'" "C2'"  SING N N 3  
OI6 "C1'" N9     SING N N 4  
OI6 "C1'" "O4'"  SING N N 5  
OI6 C2    N3     DOUB Y N 6  
OI6 C2    N1     SING Y N 7  
OI6 C3D   C4D    SING N N 8  
OI6 C3D   C2D    SING N N 9  
OI6 C3D   O3D    SING N N 10 
OI6 C4D   C5D    SING N N 11 
OI6 C5D   O5D    SING N N 12 
OI6 "C5'" "O5'"  SING N N 13 
OI6 C4    C5     DOUB Y N 14 
OI6 C4    N9     SING Y N 15 
OI6 C4    N3     SING Y N 16 
OI6 C6    C5     SING Y N 17 
OI6 C6    N1     DOUB Y N 18 
OI6 C6    N6     SING N N 19 
OI6 C5    N7     SING Y N 20 
OI6 C8    N9     SING Y N 21 
OI6 C8    N7     DOUB Y N 22 
OI6 C8    BR28   SING N N 23 
OI6 "C2'" "C3'"  SING N N 24 
OI6 "C2'" "O2'"  SING N N 25 
OI6 "C3'" "O3'"  SING N N 26 
OI6 C1D   C2D    SING N N 27 
OI6 C1D   O4D    SING N N 28 
OI6 C1D   O1D    SING N N 29 
OI6 C2D   O2D    SING N N 30 
OI6 O5D   PB     SING N N 31 
OI6 O1B   PB     DOUB N N 32 
OI6 O2B   PB     SING N N 33 
OI6 O3A   PB     SING N N 34 
OI6 O3A   PA     SING N N 35 
OI6 O1A   PA     DOUB N N 36 
OI6 O2A   PA     SING N N 37 
OI6 "O5'" PA     SING N N 38 
OI6 "C4'" "H'4"  SING N N 39 
OI6 "C1'" "H'1"  SING N N 40 
OI6 C2    H2     SING N N 41 
OI6 C3D   "HR'3" SING N N 42 
OI6 C4D   "HR'4" SING N N 43 
OI6 C5D   H5R1   SING N N 44 
OI6 C5D   H5R2   SING N N 45 
OI6 "C5'" "H5'1" SING N N 46 
OI6 "C5'" "H5'2" SING N N 47 
OI6 "C2'" "H'2"  SING N N 48 
OI6 "C3'" "H'3"  SING N N 49 
OI6 C2D   "HR'2" SING N N 50 
OI6 N6    H61    SING N N 51 
OI6 N6    H62    SING N N 52 
OI6 O3D   HOR3   SING N N 53 
OI6 O2B   HOB2   SING N N 54 
OI6 O2A   HOA2   SING N N 55 
OI6 "O2'" "HO'2" SING N N 56 
OI6 "O3'" "HO'3" SING N N 57 
OI6 O1D   HOR1   SING N N 58 
OI6 O2D   HOR2   SING N N 59 
OI6 "C4'" "O4'"  SING N N 60 
OI6 C4D   O4D    SING N N 61 
OI6 C1D   "HR'1" SING N N 62 
# 
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 
OI6 InChI            InChI                1.06    "InChI=1S/C15H22BrN5O14P2/c16-15-20-6-11(17)18-3-19-12(6)21(15)13-9(24)7(22)4(33-13)1-31-36(27,28)35-37(29,30)32-2-5-8(23)10(25)14(26)34-5/h3-5,7-10,13-14,22-26H,1-2H2,(H,27,28)(H,29,30)(H2,17,18,19)/t4-,5-,7-,8-,9-,10-,13-,14-/m1/s1" 
OI6 InChIKey         InChI                1.06    DPZGAPGUTMHLAW-AIKIOGRUSA-N                                                                                                                                                                                                                
OI6 SMILES_CANONICAL CACTVS               3.385   "Nc1ncnc2n([C@@H]3O[C@H](CO[P](O)(=O)O[P](O)(=O)OC[C@H]4O[C@@H](O)[C@H](O)[C@@H]4O)[C@@H](O)[C@H]3O)c(Br)nc12"                                                                                                                             
OI6 SMILES           CACTVS               3.385   "Nc1ncnc2n([CH]3O[CH](CO[P](O)(=O)O[P](O)(=O)OC[CH]4O[CH](O)[CH](O)[CH]4O)[CH](O)[CH]3O)c(Br)nc12"                                                                                                                                         
OI6 SMILES_CANONICAL "OpenEye OEToolkits" 3.1.0.0 "c1nc(c2c(n1)n(c(n2)Br)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)OP(=O)(O)OC[C@@H]4[C@H]([C@H]([C@@H](O4)O)O)O)O)O)N"                                                                                                                         
OI6 SMILES           "OpenEye OEToolkits" 3.1.0.0 "c1nc(c2c(n1)n(c(n2)Br)C3C(C(C(O3)COP(=O)(O)OP(=O)(O)OCC4C(C(C(O4)O)O)O)O)O)N"                                                                                                                                                             
# 
_pdbx_chem_comp_identifier.comp_id           OI6 
_pdbx_chem_comp_identifier.type              "SYSTEMATIC NAME" 
_pdbx_chem_comp_identifier.program           "OpenEye OEToolkits" 
_pdbx_chem_comp_identifier.program_version   3.1.0.0 
_pdbx_chem_comp_identifier.identifier        "[[(2~{R},3~{S},4~{R},5~{R})-5-(6-azanyl-8-bromanyl-purin-9-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methoxy-oxidanyl-phosphoryl] [(2~{R},3~{S},4~{R},5~{R})-3,4,5-tris(oxidanyl)oxolan-2-yl]methyl hydrogen phosphate" 
# 
loop_
_pdbx_chem_comp_synonyms.ordinal 
_pdbx_chem_comp_synonyms.comp_id 
_pdbx_chem_comp_synonyms.name 
_pdbx_chem_comp_synonyms.provenance 
_pdbx_chem_comp_synonyms.type 
1 OI6 "[[(2~{R},3~{S},4~{R},5~{R})-5-(6-azanyl-8-bromanyl-purin-9-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methoxy-oxidanyl-phosphoryl] [(2~{R},3~{S},4~{R},5~{R})-3,4,5-tris(oxidanyl)oxolan-2-yl]methyl hydrogen phosphate" PDB    ? 
2 OI6 "[[(2R,3S,4R,5R)-5-(6-azanyl-8-bromanyl-purin-9-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methoxy-oxidanyl-phosphoryl] [(2R,3S,4R,5R)-3,4,5-tris(oxidanyl)oxolan-2-yl]methyl hydrogen phosphate"                         PDB    ? 
3 OI6 8Br-ADPR                                                                                                                                                                                                        AUTHOR ? 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
OI6 "Create component" 2022-09-08 PDBE 
OI6 "Initial release"  2024-03-20 RCSB 
# 
