data_23G
# 
_chem_comp.id                                    23G 
_chem_comp.name                                  
;GUANOSINE-5'-PHOSPHATE-2',3'-CYCLIC PHOSPHATE
;
_chem_comp.type                                  "RNA OH 3 prime terminus" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C10 H13 N5 O10 P2" 
_chem_comp.mon_nstd_parent_comp_id               G 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2009-09-09 
_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                        425.185 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     23G 
_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        3IVN 
_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 
23G P      P      P 0 1 N N N -30.447 24.891 45.405 5.083  -1.611 -0.274 P      23G 1  
23G N1     N1     N 0 1 N N N -27.546 18.981 45.180 -5.599 -1.367 -0.338 N1     23G 2  
23G C2     C2     C 0 1 N N N -27.210 20.255 45.543 -4.996 -0.361 -1.032 C2     23G 3  
23G N2     N2     N 0 1 N N N -26.442 20.910 44.768 -5.762 0.449  -1.831 N2     23G 4  
23G N3     N3     N 0 1 N N N -27.654 20.851 46.642 -3.702 -0.145 -0.958 N3     23G 5  
23G C4     C4     C 0 1 Y N N -28.470 20.230 47.493 -2.915 -0.910 -0.192 C4     23G 6  
23G C5     C5     C 0 1 Y N N -28.861 18.946 47.189 -3.475 -1.959 0.546  C5     23G 7  
23G C6     C6     C 0 1 N N N -28.400 18.318 46.039 -4.869 -2.181 0.457  C6     23G 8  
23G O6     O6     O 0 1 N N N -28.742 17.177 45.780 -5.399 -3.083 1.082  O6     23G 9  
23G N7     N7     N 0 1 Y N N -29.632 18.563 48.159 -2.465 -2.559 1.222  N7     23G 10 
23G C8     C8     C 0 1 Y N N -29.740 19.546 49.017 -1.346 -1.955 0.949  C8     23G 11 
23G N9     N9     N 0 1 Y N N -29.029 20.576 48.638 -1.574 -0.928 0.079  N9     23G 12 
23G PC     PC     P 0 1 N N N -27.220 23.710 51.483 0.215  3.545  0.201  PC     23G 13 
23G "C1'"  "C1'"  C 0 1 N N R -28.957 21.873 49.379 -0.567 -0.013 -0.465 "C1'"  23G 14 
23G "C2'"  "C2'"  C 0 1 N N R -27.716 22.800 49.305 -0.510 1.271  0.389  "C2'"  23G 15 
23G "O2'"  "O2'"  O 0 1 N N N -26.809 22.681 50.406 -0.716 2.399  -0.496 "O2'"  23G 16 
23G "C3'"  "C3'"  C 0 1 N N R -28.324 24.187 49.509 0.959  1.330  0.875  "C3'"  23G 17 
23G "O3'"  "O3'"  O 0 1 N N N -28.430 24.445 50.950 1.458  2.669  0.784  "O3'"  23G 18 
23G "C4'"  "C4'"  C 0 1 N N R -29.667 24.015 48.746 1.684  0.429  -0.151 "C4'"  23G 19 
23G "O4'"  "O4'"  O 0 1 N N N -30.054 22.663 48.826 0.732  -0.626 -0.406 "O4'"  23G 20 
23G "C5'"  "C5'"  C 0 1 N N N -29.272 24.170 47.326 2.972  -0.141 0.448  "C5'"  23G 21 
23G "O5'"  "O5'"  O 0 1 N N N -30.012 25.126 46.723 3.680  -0.873 -0.554 "O5'"  23G 22 
23G OC1    OC1    O 0 1 N N N -26.194 24.796 51.715 -0.577 4.282  1.394  OC1    23G 23 
23G OC2    OC2    O 0 1 N N N -27.362 23.029 52.804 0.685  4.525  -0.803 OC2    23G 24 
23G OP1    OP1    O 0 1 N N N -30.125 26.036 44.664 6.053  -0.636 0.273  OP1    23G 25 
23G OP2    OP2    O 0 1 N N N -31.884 24.769 45.380 4.861  -2.801 0.788  OP2    23G 26 
23G HN1    HN1    H 0 1 N N N -27.196 18.556 44.345 -6.558 -1.497 -0.412 HN1    23G 27 
23G HN2    HN2    H 0 1 N N N -26.187 21.850 44.994 -6.719 0.303  -1.896 HN2    23G 28 
23G HN2A   HN2A   H 0 0 N N N -26.093 20.484 43.933 -5.348 1.170  -2.332 HN2A   23G 29 
23G H8     H8     H 0 1 N N N -30.336 19.511 49.917 -0.380 -2.225 1.351  H8     23G 30 
23G "H1'"  "H1'"  H 0 1 N N N -28.958 21.562 50.434 -0.814 0.238  -1.496 "H1'"  23G 31 
23G "H2'"  "H2'"  H 0 1 N N N -27.166 22.579 48.379 -1.226 1.254  1.210  "H2'"  23G 32 
23G "H3'"  "H3'"  H 0 1 N N N -27.766 25.060 49.139 1.055  0.943  1.890  "H3'"  23G 33 
23G "H4'"  "H4'"  H 0 1 N N N -30.447 24.694 49.120 1.898  0.983  -1.065 "H4'"  23G 34 
23G "H5'"  "H5'"  H 0 1 N N N -28.211 24.455 47.278 3.596  0.675  0.811  "H5'"  23G 35 
23G "H5'A" "H5'A" H 0 0 N N N -29.427 23.214 46.804 2.724  -0.805 1.276  "H5'A" 23G 36 
23G OP3    OP3    O 0 1 N Y N -29.684 23.479 44.786 5.654  -2.220 -1.651 OP3    23G 37 
23G H11    H11    H 0 1 N N N -25.906 24.772 52.620 -1.388 4.725  1.112  H11    23G 38 
23G HOP2   HOP2   H 0 0 N N N -32.254 25.484 44.875 4.236  -3.478 0.494  HOP2   23G 39 
23G HOP3   HOP3   H 0 0 N Y N -29.159 23.709 44.029 6.499  -2.680 -1.557 HOP3   23G 40 
# 
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 
23G P     "O5'"  SING N N 1  
23G P     OP1    DOUB N N 2  
23G P     OP2    SING N N 3  
23G N1    C2     SING N N 4  
23G N1    C6     SING N N 5  
23G N1    HN1    SING N N 6  
23G C2    N2     SING N N 7  
23G C2    N3     DOUB N N 8  
23G N2    HN2    SING N N 9  
23G N2    HN2A   SING N N 10 
23G N3    C4     SING N N 11 
23G C4    C5     DOUB Y N 12 
23G C4    N9     SING Y N 13 
23G C5    C6     SING N N 14 
23G C5    N7     SING Y N 15 
23G C6    O6     DOUB N N 16 
23G N7    C8     DOUB Y N 17 
23G C8    N9     SING Y N 18 
23G C8    H8     SING N N 19 
23G N9    "C1'"  SING N N 20 
23G PC    "O2'"  SING N N 21 
23G PC    "O3'"  SING N N 22 
23G PC    OC1    SING N N 23 
23G PC    OC2    DOUB N N 24 
23G "C1'" "C2'"  SING N N 25 
23G "C1'" "O4'"  SING N N 26 
23G "C1'" "H1'"  SING N N 27 
23G "C2'" "O2'"  SING N N 28 
23G "C2'" "C3'"  SING N N 29 
23G "C2'" "H2'"  SING N N 30 
23G "C3'" "O3'"  SING N N 31 
23G "C3'" "C4'"  SING N N 32 
23G "C3'" "H3'"  SING N N 33 
23G "C4'" "O4'"  SING N N 34 
23G "C4'" "C5'"  SING N N 35 
23G "C4'" "H4'"  SING N N 36 
23G "C5'" "O5'"  SING N N 37 
23G "C5'" "H5'"  SING N N 38 
23G "C5'" "H5'A" SING N N 39 
23G P     OP3    SING N N 40 
23G OC1   H11    SING N N 41 
23G OP2   HOP2   SING N N 42 
23G OP3   HOP3   SING N N 43 
# 
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 
23G SMILES           ACDLabs              11.02 "O=C4NC(=Nc1c4ncn1C2OC(C3OP(=O)(O)OC23)COP(=O)(O)O)N"                                                                                                                                
23G SMILES_CANONICAL CACTVS               3.352 "NC1=Nc2n(cnc2C(=O)N1)[C@@H]3O[C@H](CO[P](O)(O)=O)[C@H]4O[P](O)(=O)O[C@@H]34"                                                                                                        
23G SMILES           CACTVS               3.352 "NC1=Nc2n(cnc2C(=O)N1)[CH]3O[CH](CO[P](O)(O)=O)[CH]4O[P](O)(=O)O[CH]34"                                                                                                              
23G SMILES_CANONICAL "OpenEye OEToolkits" 1.7.0 "c1nc2c(n1[C@H]3[C@H]4[C@@H]([C@H](O3)COP(=O)(O)O)O[P@@](=O)(O4)O)N=C(NC2=O)N"                                                                                                       
23G SMILES           "OpenEye OEToolkits" 1.7.0 "c1nc2c(n1C3C4C(C(O3)COP(=O)(O)O)OP(=O)(O4)O)N=C(NC2=O)N"                                                                                                                            
23G InChI            InChI                1.03  "InChI=1S/C10H13N5O10P2/c11-10-13-7-4(8(16)14-10)12-2-15(7)9-6-5(24-27(20,21)25-6)3(23-9)1-22-26(17,18)19/h2-3,5-6,9H,1H2,(H,20,21)(H2,17,18,19)(H3,11,13,14,16)/t3-,5-,6-,9-/m1/s1" 
23G InChIKey         InChI                1.03  ZBMMALUAVDLKSL-UUOKFMHZSA-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 
23G "SYSTEMATIC NAME" ACDLabs              11.02 "[(2S,3aR,4R,6R,6aR)-6-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-2-hydroxy-2-oxidotetrahydrofuro[3,4-d][1,3,2]dioxaphosphol-4-yl]methyl dihydrogen phosphate" 
23G "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.6.1 "[(1R,3S,5R,6R,8R)-8-(2-azanyl-6-oxo-1H-purin-9-yl)-3-hydroxy-3-oxo-2,4,7-trioxa-3$l^{5}-phosphabicyclo[3.3.0]octan-6-yl]methyl dihydrogen phosphate"         
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
23G "Create component"     2009-09-09 RCSB 
23G "Modify aromatic_flag" 2011-06-04 RCSB 
23G "Modify descriptor"    2011-06-04 RCSB 
# 
