data_IOO
# 
_chem_comp.id                                    IOO 
_chem_comp.name                                  
; N7-(3,4-difluorobenzyl) guanosine 5'-monophosphate
;
_chem_comp.type                                  "L-RNA linking" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C17 H19 F2 N5 O8 P" 
_chem_comp.mon_nstd_parent_comp_id               G 
_chem_comp.pdbx_synonyms                         "[(2R,3S,4R,5R)-5-[2-azanyl-7-[[3,4-bis(fluoranyl)phenyl]methyl]-6-oxidanylidene-1H-purin-7-ium-9-yl]-3,4-bis(oxidanyl)oxolan-2-yl]methyl dihydrogen phosphate" 
_chem_comp.pdbx_formal_charge                    1 
_chem_comp.pdbx_initial_date                     2022-04-04 
_chem_comp.pdbx_modified_date                    2022-08-22 
_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                        490.332 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     IOO 
_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        7ZEG 
_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.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 
IOO "C2'"  C2    C 0 1 N N N 3.021  -22.020 9.641  3.147  -3.622 -0.758 "C2'"  IOO 1  
IOO C1     C5    C 0 1 Y N N 0.548  -21.627 8.560  2.466  -1.352 0.560  C1     IOO 2  
IOO "C1'"  C4    C 0 1 Y N N 1.632  -21.782 7.795  1.512  -2.122 -0.115 "C1'"  IOO 3  
IOO N1     N2    N 0 1 N N N 4.233  -22.222 10.153 3.487  -4.771 -1.426 N1     IOO 4  
IOO N4     N1    N 0 1 N N N 1.921  -21.879 10.470 4.121  -2.912 -0.123 N4     IOO 5  
IOO C2     "C1'" C 0 1 N N R 2.214  -21.813 5.395  -0.984 -1.918 -0.460 C2     IOO 6  
IOO C3     "C2'" C 0 1 N N R 1.855  -23.080 4.591  -1.660 -2.914 0.516  C3     IOO 7  
IOO "C3'"  "C3'" C 0 1 N N S 2.326  -22.757 3.173  -3.158 -2.747 0.164  "C3'"  IOO 8  
IOO "C4'"  "C4'" C 0 1 N N R 2.695  -21.268 3.276  -3.233 -1.370 -0.525 "C4'"  IOO 9  
IOO "C5'"  "C5'" C 0 1 N N N 2.095  -20.585 2.059  -4.195 -0.458 0.240  "C5'"  IOO 10 
IOO C6     C6    C 0 1 N N N 0.669  -21.685 9.892  3.815  -1.776 0.542  C6     IOO 11 
IOO C8     C8    C 0 1 Y N N -0.045 -21.496 6.490  0.549  -0.376 0.823  C8     IOO 12 
IOO C11    CAY   C 0 1 N N N -1.949 -21.220 8.062  2.439  0.759  1.911  C11    IOO 13 
IOO C12    CAZ   C 0 1 Y N N -2.219 -19.847 8.255  2.983  1.827  0.997  C12    IOO 14 
IOO C13    CBA   C 0 1 Y N N -3.077 -17.737 7.419  4.778  2.713  -0.318 C13    IOO 15 
IOO C14    CBB   C 0 1 Y N N -2.793 -19.091 7.237  4.277  1.735  0.521  C14    IOO 16 
IOO C15    CBC   C 0 1 Y N N -2.787 -17.135 8.641  3.983  3.786  -0.682 C15    IOO 17 
IOO C16    CBD   C 0 1 Y N N -1.942 -19.239 9.476  2.184  2.894  0.631  C16    IOO 18 
IOO C17    CBE   C 0 1 Y N N -2.219 -17.887 9.666  2.683  3.875  -0.208 C17    IOO 19 
IOO F1     FBF   F 0 1 N N N -3.062 -15.790 8.835  4.473  4.745  -1.497 F1     IOO 20 
IOO F2     FBG   F 0 1 N N N -1.927 -17.284 10.893 1.905  4.922  -0.562 F2     IOO 21 
IOO N3     N3    N 0 1 N N N 2.849  -21.954 8.321  1.890  -3.236 -0.753 N3     IOO 22 
IOO N7     N7    N 1 1 Y N N -0.497 -21.454 7.744  1.815  -0.298 1.110  N7     IOO 23 
IOO N9     N9    N 0 1 Y N N 1.274  -21.663 6.529  0.314  -1.484 0.062  N9     IOO 24 
IOO "O2'"  "O2'" O 0 1 N N N 2.511  -24.262 5.107  -1.223 -4.251 0.264  "O2'"  IOO 25 
IOO "O3'"  "O3'" O 0 1 N N N 3.503  -23.509 2.809  -3.583 -3.777 -0.730 "O3'"  IOO 26 
IOO "O4'"  "O4'" O 0 1 N N N 1.993  -20.824 4.414  -1.908 -0.809 -0.510 "O4'"  IOO 27 
IOO "O5'"  "O5'" O 0 1 N N N 2.357  -19.151 2.053  -4.347 0.774  -0.469 "O5'"  IOO 28 
IOO OP1    O6    O 0 1 N N N -0.299 -21.559 10.638 4.680  -1.134 1.113  OP1    IOO 29 
IOO O1     OAT   O 0 1 N N N 3.694  -18.717 0.083  -4.901 2.346  1.426  O1     IOO 30 
IOO OP3    OAU   O 0 1 N Y N 3.604  -17.018 1.758  -5.121 3.245  -0.923 OP3    IOO 31 
IOO OP2    OAV   O 0 1 N N N 5.022  -19.012 2.212  -6.826 1.489  0.036  OP2    IOO 32 
IOO P      PAS   P 0 1 N N N 3.750  -18.523 1.576  -5.290 1.972  0.048  P      IOO 33 
IOO H21    H1    H 0 1 N N N 5.021  -22.325 9.546  4.411  -5.068 -1.442 H21    IOO 34 
IOO H22    H2    H 0 1 N N N 4.355  -22.271 11.144 2.805  -5.288 -1.883 H22    IOO 35 
IOO H1     H3    H 0 1 N N N 2.024  -21.916 11.464 5.040  -3.223 -0.149 H1     IOO 36 
IOO "H1'"  H4    H 0 1 N N N 3.259  -21.850 5.736  -0.869 -2.366 -1.447 "H1'"  IOO 37 
IOO "H2'"  H5    H 0 1 N N N 0.763  -23.213 4.592  -1.469 -2.633 1.552  "H2'"  IOO 38 
IOO "H3'"  H6    H 0 1 N N N 1.508  -22.901 2.452  -3.764 -2.753 1.071  "H3'"  IOO 39 
IOO "H4'"  H7    H 0 1 N N N 3.783  -21.120 3.338  -3.571 -1.489 -1.554 "H4'"  IOO 40 
IOO "H5'"  H8    H 0 1 N N N 1.007  -20.747 2.061  -5.164 -0.947 0.331  "H5'"  IOO 41 
IOO "H5''" H9    H 0 0 N N N 2.530  -21.029 1.152  -3.793 -0.258 1.233  "H5''" IOO 42 
IOO H8     H10   H 0 1 N N N -0.646 -21.409 5.597  -0.205 0.330  1.140  H8     IOO 43 
IOO H11    H11   H 0 1 N N N -2.563 -21.592 7.228  3.253  0.336  2.500  H11    IOO 44 
IOO H12    H12   H 0 1 N N N -2.207 -21.768 8.980  1.696  1.196  2.578  H12    IOO 45 
IOO H13    H13   H 0 1 N N N -3.518 -17.161 6.619  5.791  2.642  -0.686 H13    IOO 46 
IOO H14    H14   H 0 1 N N N -3.022 -19.560 6.291  4.898  0.898  0.804  H14    IOO 47 
IOO H15    H15   H 0 1 N N N -1.511 -19.818 10.279 1.172  2.963  1.000  H15    IOO 48 
IOO "HO2'" H16   H 0 0 N N N 2.200  -24.439 5.987  -1.618 -4.911 0.850  "HO2'" IOO 49 
IOO "HO3'" H17   H 0 0 N Y N 3.283  -24.431 2.743  -3.556 -4.665 -0.348 "HO3'" IOO 50 
IOO HOP3   H18   H 0 0 N Y N 3.518  -16.603 0.908  -5.661 4.007  -0.671 HOP3   IOO 51 
IOO HOP2   H19   H 0 0 N N N 5.593  -19.372 1.543  -7.150 1.228  -0.837 HOP2   IOO 52 
# 
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 
IOO O1    P      DOUB N N 1  
IOO P     OP3    SING N N 2  
IOO P     "O5'"  SING N N 3  
IOO P     OP2    SING N N 4  
IOO "O5'" "C5'"  SING N N 5  
IOO "C5'" "C4'"  SING N N 6  
IOO "O3'" "C3'"  SING N N 7  
IOO "C3'" "C4'"  SING N N 8  
IOO "C3'" C3     SING N N 9  
IOO "C4'" "O4'"  SING N N 10 
IOO "O4'" C2     SING N N 11 
IOO C3    "O2'"  SING N N 12 
IOO C3    C2     SING N N 13 
IOO C2    N9     SING N N 14 
IOO C8    N9     SING Y N 15 
IOO C8    N7     DOUB Y N 16 
IOO N9    "C1'"  SING Y N 17 
IOO C14   C13    DOUB Y N 18 
IOO C14   C12    SING Y N 19 
IOO C13   C15    SING Y N 20 
IOO N7    C11    SING N N 21 
IOO N7    C1     SING Y N 22 
IOO "C1'" N3     SING N N 23 
IOO "C1'" C1     DOUB Y N 24 
IOO C11   C12    SING N N 25 
IOO C12   C16    DOUB Y N 26 
IOO N3    "C2'"  DOUB N N 27 
IOO C1    C6     SING N N 28 
IOO C15   F1     SING N N 29 
IOO C15   C17    DOUB Y N 30 
IOO C16   C17    SING Y N 31 
IOO "C2'" N1     SING N N 32 
IOO "C2'" N4     SING N N 33 
IOO C17   F2     SING N N 34 
IOO C6    N4     SING N N 35 
IOO C6    OP1    DOUB N N 36 
IOO N1    H21    SING N N 37 
IOO N1    H22    SING N N 38 
IOO N4    H1     SING N N 39 
IOO C2    "H1'"  SING N N 40 
IOO C3    "H2'"  SING N N 41 
IOO "C3'" "H3'"  SING N N 42 
IOO "C4'" "H4'"  SING N N 43 
IOO "C5'" "H5'"  SING N N 44 
IOO "C5'" "H5''" SING N N 45 
IOO C8    H8     SING N N 46 
IOO C11   H11    SING N N 47 
IOO C11   H12    SING N N 48 
IOO C13   H13    SING N N 49 
IOO C14   H14    SING N N 50 
IOO C16   H15    SING N N 51 
IOO "O2'" "HO2'" SING N N 52 
IOO "O3'" "HO3'" SING N N 53 
IOO OP3   HOP3   SING N N 54 
IOO OP2   HOP2   SING N N 55 
# 
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 
IOO InChI            InChI                1.06  "InChI=1S/C17H18F2N5O8P/c18-8-2-1-7(3-9(8)19)4-23-6-24(14-11(23)15(27)22-17(20)21-14)16-13(26)12(25)10(32-16)5-31-33(28,29)30/h1-3,6,10,12-13,16,25-26H,4-5H2,(H4-,20,21,22,27,28,29,30)/p+1/t10-,12-,13-,16-/m1/s1" 
IOO InChIKey         InChI                1.06  BIHPVAUGYOUOAQ-XNIJJKJLSA-O                                                                                                                                                                                          
IOO SMILES_CANONICAL CACTVS               3.385 "NC1=Nc2n(c[n+](Cc3ccc(F)c(F)c3)c2C(=O)N1)[C@@H]4O[C@H](CO[P](O)(O)=O)[C@@H](O)[C@H]4O"                                                                                                                              
IOO SMILES           CACTVS               3.385 "NC1=Nc2n(c[n+](Cc3ccc(F)c(F)c3)c2C(=O)N1)[CH]4O[CH](CO[P](O)(O)=O)[CH](O)[CH]4O"                                                                                                                                    
IOO SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "c1cc(c(cc1C[n+]2cn(c3c2C(=O)NC(=N3)N)[C@H]4[C@@H]([C@@H]([C@H](O4)COP(=O)(O)O)O)O)F)F"                                                                                                                              
IOO SMILES           "OpenEye OEToolkits" 2.0.7 "c1cc(c(cc1C[n+]2cn(c3c2C(=O)NC(=N3)N)C4C(C(C(O4)COP(=O)(O)O)O)O)F)F"                                                                                                                                                
# 
_pdbx_chem_comp_identifier.comp_id           IOO 
_pdbx_chem_comp_identifier.type              "SYSTEMATIC NAME" 
_pdbx_chem_comp_identifier.program           "OpenEye OEToolkits" 
_pdbx_chem_comp_identifier.program_version   2.0.7 
_pdbx_chem_comp_identifier.identifier        "[(2~{R},3~{S},4~{R},5~{R})-5-[2-azanyl-7-[[3,4-bis(fluoranyl)phenyl]methyl]-6-oxidanylidene-1~{H}-purin-7-ium-9-yl]-3,4-bis(oxidanyl)oxolan-2-yl]methyl dihydrogen phosphate" 
# 
_pdbx_chem_comp_synonyms.ordinal      1 
_pdbx_chem_comp_synonyms.comp_id      IOO 
_pdbx_chem_comp_synonyms.name         "[(2R,3S,4R,5R)-5-[2-azanyl-7-[[3,4-bis(fluoranyl)phenyl]methyl]-6-oxidanylidene-1H-purin-7-ium-9-yl]-3,4-bis(oxidanyl)oxolan-2-yl]methyl dihydrogen phosphate" 
_pdbx_chem_comp_synonyms.provenance   ? 
_pdbx_chem_comp_synonyms.type         ? 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
IOO "Create component"    2022-04-04 PDBE 
IOO "Modify linking type" 2022-04-05 PDBE 
IOO "Initial release"     2022-04-13 RCSB 
IOO "Modify descriptor"   2022-08-22 RCSB 
# 
