data_IRN
# 
_chem_comp.id                                    IRN 
_chem_comp.name                                  "1-(5-O-phosphono-beta-D-ribofuranosyl)-1H-imidazole" 
_chem_comp.type                                  "RNA linking" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C8 H13 N2 O7 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-10-03 
_chem_comp.pdbx_modified_date                    2009-01-07 
_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                        280.172 
_chem_comp.one_letter_code                       N 
_chem_comp.three_letter_code                     IRN 
_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        3EPN 
_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 
IRN C5     C5     C 0 1 Y N N 64.245 40.209 32.941 4.147  -1.082 0.699  C5     IRN 1  
IRN C4     C4     C 0 1 Y N N 63.319 39.341 33.348 4.548  -2.247 0.156  C4     IRN 2  
IRN N3     N3     N 0 1 Y N N 63.909 38.157 33.496 3.554  -2.706 -0.619 N3     IRN 3  
IRN C2     C2     C 0 1 Y N N 65.197 38.291 33.175 2.554  -1.870 -0.578 C2     IRN 4  
IRN N1     N1     N 0 1 Y N N 65.399 39.561 32.825 2.881  -0.844 0.238  N1     IRN 5  
IRN "C1'"  "C1'"  C 0 1 N N R 66.688 40.161 32.408 2.039  0.311  0.563  "C1'"  IRN 6  
IRN "O4'"  "O4'"  O 0 1 N N N 67.621 39.124 31.987 0.649  -0.073 0.616  "O4'"  IRN 7  
IRN "C2'"  "C2'"  C 0 1 N N R 67.403 40.879 33.553 2.083  1.356  -0.581 "C2'"  IRN 8  
IRN "O2'"  "O2'"  O 0 1 N N N 66.910 42.215 33.690 3.191  2.243  -0.419 "O2'"  IRN 9  
IRN "C3'"  "C3'"  C 0 1 N N S 68.796 40.941 32.973 0.743  2.106  -0.386 "C3'"  IRN 10 
IRN "O3'"  "O3'"  O 0 1 N N N 68.771 41.869 31.885 0.949  3.317  0.343  "O3'"  IRN 11 
IRN "C4'"  "C4'"  C 0 1 N N R 68.958 39.533 32.411 -0.124 1.125  0.428  "C4'"  IRN 12 
IRN "C5'"  "C5'"  C 0 1 N N N 69.501 38.564 33.465 -1.406 0.801  -0.343 "C5'"  IRN 13 
IRN "O5'"  "O5'"  O 0 1 N N N 69.479 37.250 32.936 -2.247 -0.029 0.460  "O5'"  IRN 14 
IRN P      P      P 0 1 N N N 69.653 35.930 33.846 -3.682 -0.564 -0.037 P      IRN 15 
IRN O6     O6     O 0 1 N N N 71.046 36.047 34.645 -4.682 0.683  -0.234 O6     IRN 16 
IRN O7     O7     O 0 1 N N N 69.795 34.807 32.703 -3.524 -1.277 -1.324 O7     IRN 17 
IRN O8     O8     O 0 1 N N N 68.500 35.674 34.752 -4.290 -1.571 1.063  O8     IRN 18 
IRN H5     H5     H 0 1 N N N 64.085 41.258 32.740 4.715  -0.457 1.373  H5     IRN 19 
IRN H4     H4     H 0 1 N N N 62.276 39.559 33.526 5.501  -2.728 0.317  H4     IRN 20 
IRN H2     H2     H 0 1 N N N 65.943 37.510 33.195 1.618  -1.980 -1.105 H2     IRN 21 
IRN "H1'"  "H1'"  H 0 1 N N N 66.429 40.864 31.602 2.353  0.759  1.505  "H1'"  IRN 22 
IRN "H2'"  "H2'"  H 0 1 N N N 67.298 40.399 34.537 2.117  0.867  -1.554 "H2'"  IRN 23 
IRN "HO2'" "HO2'" H 0 0 N N N 66.801 42.420 34.611 3.261  2.915  -1.110 "HO2'" IRN 24 
IRN "H3'"  "H3'"  H 0 1 N N N 69.585 41.240 33.679 0.279  2.316  -1.350 "H3'"  IRN 25 
IRN "HO3'" "HO3'" H 0 0 N N N 68.765 42.756 32.225 1.535  3.947  -0.099 "HO3'" IRN 26 
IRN "H4'"  "H4'"  H 0 1 N N N 69.680 39.521 31.581 -0.371 1.562  1.395  "H4'"  IRN 27 
IRN "H5'"  "H5'"  H 0 1 N N N 70.533 38.841 33.725 -1.929 1.726  -0.582 "H5'"  IRN 28 
IRN "H5'A" "H5'A" H 0 0 N N N 68.878 38.611 34.370 -1.153 0.278  -1.265 "H5'A" IRN 29 
IRN HO6    HO6    H 0 1 N N N 71.766 36.070 34.026 -4.832 1.197  0.572  HO6    IRN 30 
IRN HO8    HO8    H 0 1 N N N 68.808 35.619 35.649 -5.155 -1.933 0.829  HO8    IRN 31 
# 
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 
IRN N1    C5     SING Y N 1  
IRN C5    C4     DOUB N N 2  
IRN C5    H5     SING Y N 3  
IRN C4    N3     SING N N 4  
IRN C4    H4     SING Y N 5  
IRN C2    N3     DOUB N N 6  
IRN N1    C2     SING Y N 7  
IRN C2    H2     SING Y N 8  
IRN "C1'" N1     SING N N 9  
IRN "O4'" "C1'"  SING N N 10 
IRN "C1'" "C2'"  SING N N 11 
IRN "C1'" "H1'"  SING N N 12 
IRN "O4'" "C4'"  SING N N 13 
IRN "C3'" "C2'"  SING N N 14 
IRN "C2'" "O2'"  SING N N 15 
IRN "C2'" "H2'"  SING N N 16 
IRN "O2'" "HO2'" SING N N 17 
IRN "O3'" "C3'"  SING N N 18 
IRN "C4'" "C3'"  SING N N 19 
IRN "C3'" "H3'"  SING N N 20 
IRN "O3'" "HO3'" SING N N 21 
IRN "C4'" "C5'"  SING N N 22 
IRN "C4'" "H4'"  SING N N 23 
IRN "O5'" "C5'"  SING N N 24 
IRN "C5'" "H5'"  SING N N 25 
IRN "C5'" "H5'A" SING N N 26 
IRN "O5'" P      SING N N 27 
IRN O7    P      DOUB N N 28 
IRN P     O6     SING N N 29 
IRN P     O8     SING N N 30 
IRN O6    HO6    SING N N 31 
IRN O8    HO8    SING N N 32 
# 
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 
IRN SMILES           ACDLabs              10.04 "O=P(O)(O)OCC2OC(n1cncc1)C(O)C2O"                                                                                                      
IRN InChI            InChI                1.02b "InChI=1/C8H13N2O7P/c11-6-5(3-16-18(13,14)15)17-8(7(6)12)10-2-1-9-4-10/h1-2,4-8,11-12H,3H2,(H2,13,14,15)/t5-,6-,7-,8-/m1/s1/f/h13-14H" 
IRN InChIKey         InChI                1.02b YEBULYOZZUNFGU-UHWNFFEYDC                                                                                                              
IRN SMILES_CANONICAL CACTVS               3.341 "O[C@H]1[C@@H](O)[C@@H](O[C@@H]1CO[P](O)(O)=O)n2ccnc2"                                                                                 
IRN SMILES           CACTVS               3.341 "O[CH]1[CH](O)[CH](O[CH]1CO[P](O)(O)=O)n2ccnc2"                                                                                        
IRN SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1cn(cn1)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O"                                                                                
IRN SMILES           "OpenEye OEToolkits" 1.5.0 "c1cn(cn1)C2C(C(C(O2)COP(=O)(O)O)O)O"                                                                                                  
# 
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 
IRN "SYSTEMATIC NAME" ACDLabs              10.04 "1-(5-O-phosphono-beta-D-ribofuranosyl)-1H-imidazole"                                  
IRN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-3,4-dihydroxy-5-imidazol-1-yl-oxolan-2-yl]methyl dihydrogen phosphate" 
# 
