data_DOI
# 
_chem_comp.id                                    DOI 
_chem_comp.name                                  9-(2-DEOXY-5-O-PHOSPHONO-BETA-D-ERYTHRO-PENTOFURANOSYL)-6-(PHOSPHONOOXY)-9H-PURINE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C10 H14 N4 O10 P2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "2'-DEOXY-IMP" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-03-16 
_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                        412.186 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     DOI 
_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   Y 
_chem_comp.pdbx_model_coordinates_db_code        2DGN 
_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 
DOI PA     PA   P 0 1 N N N 60.758 66.545 39.999 -5.895 -1.207 0.171  PA     DOI 1  
DOI O1A    O1A  O 0 1 N N N 59.347 65.979 40.069 -5.376 -2.172 -0.824 O1A    DOI 2  
DOI O2A    O2A  O 0 1 N N N 60.891 67.868 40.733 -6.505 -2.008 1.428  O2A    DOI 3  
DOI O3A    O3A  O 0 1 N N N 61.789 65.519 40.432 -7.048 -0.309 -0.503 O3A    DOI 4  
DOI "O5'"  O5*  O 0 1 N N N 61.029 66.863 38.419 -4.697 -0.256 0.672  "O5'"  DOI 5  
DOI P6     P6   P 0 1 N N N 63.328 57.471 38.197 5.396  -1.081 -0.574 P6     DOI 6  
DOI O16    O16  O 0 1 N N N 61.956 56.968 37.744 6.528  -2.222 -0.665 O16    DOI 7  
DOI O26    O26  O 0 1 N N N 63.668 57.007 39.610 4.195  -1.435 -1.585 O26    DOI 8  
DOI O36    O36  O 0 1 N N N 64.439 57.180 37.188 5.983  0.227  -0.944 O36    DOI 9  
DOI "C5'"  C5*  C 0 1 N N N 62.258 67.473 37.965 -4.122 0.334  -0.496 "C5'"  DOI 10 
DOI "C4'"  C4*  C 0 1 N N R 62.809 66.716 36.776 -2.971 1.256  -0.088 "C4'"  DOI 11 
DOI "O4'"  O4*  O 0 1 N N N 63.191 65.386 37.186 -1.885 0.485  0.476  "O4'"  DOI 12 
DOI "C1'"  C1*  C 0 1 N N R 62.755 64.450 36.230 -0.718 1.328  0.362  "C1'"  DOI 13 
DOI N9     N9   N 0 1 Y N N 62.379 63.238 36.950 0.504  0.523  0.432  N9     DOI 14 
DOI C4     C4   C 0 1 Y N N 62.552 61.964 36.469 1.760  0.979  0.744  C4     DOI 15 
DOI N3     N3   N 0 1 Y N N 62.656 61.585 35.183 2.276  2.159  1.070  N3     DOI 16 
DOI C2     C2   C 0 1 Y N N 62.834 60.266 35.096 3.561  2.280  1.328  C2     DOI 17 
DOI N1     N1   N 0 1 Y N N 62.917 59.358 36.074 4.392  1.255  1.284  N1     DOI 18 
DOI C6     C6   C 0 1 Y N N 62.816 59.773 37.357 3.967  0.037  0.973  C6     DOI 19 
DOI O6     O6   O 0 1 N N N 63.218 59.084 38.294 4.828  -1.008 0.930  O6     DOI 20 
DOI C5     C5   C 0 1 Y N N 62.609 61.144 37.584 2.605  -0.144 0.689  C5     DOI 21 
DOI N7     N7   N 0 1 Y N N 62.454 61.885 38.747 1.836  -1.205 0.345  N7     DOI 22 
DOI C8     C8   C 0 1 Y N N 62.320 63.115 38.319 0.603  -0.816 0.194  C8     DOI 23 
DOI "C2'"  C2*  C 0 1 N N N 61.561 65.074 35.513 -0.845 1.993  -1.026 "C2'"  DOI 24 
DOI "C3'"  C3*  C 0 1 N N S 61.874 66.565 35.577 -2.360 1.945  -1.328 "C3'"  DOI 25 
DOI "O3'"  O3*  O 0 1 N N N 62.482 67.033 34.378 -2.883 3.267  -1.475 "O3'"  DOI 26 
DOI H2A    H2A  H 0 1 N N N 60.919 67.710 41.669 -7.218 -2.565 1.085  H2A    DOI 27 
DOI H3A    H3A  H 0 1 N N N 62.351 65.305 39.697 -7.358 0.305  0.177  H3A    DOI 28 
DOI H26    H26  H 0 1 N N N 63.739 56.060 39.624 3.841  -2.292 -1.310 H26    DOI 29 
DOI H36    H36  H 0 1 N N N 64.067 57.120 36.316 ?      ?      ?      H36    DOI 30 
DOI "H5'1" 1H5* H 0 0 N N N 62.995 67.446 38.781 -4.882 0.913  -1.022 "H5'1" DOI 31 
DOI "H5'2" 2H5* H 0 0 N N N 62.059 68.514 37.671 -3.745 -0.451 -1.151 "H5'2" DOI 32 
DOI "H4'"  H4*  H 0 1 N N N 63.654 67.334 36.437 -3.318 2.002  0.626  "H4'"  DOI 33 
DOI "H1'"  H1*  H 0 1 N N N 63.526 64.193 35.488 -0.718 2.084  1.147  "H1'"  DOI 34 
DOI H2     H2   H 0 1 N N N 62.924 59.876 34.093 3.949  3.254  1.586  H2     DOI 35 
DOI H8     H8   H 0 1 N N N 62.176 63.957 38.980 -0.221 -1.459 -0.079 H8     DOI 36 
DOI "H2'1" 1H2* H 0 0 N N N 60.595 64.813 35.971 -0.289 1.426  -1.773 "H2'1" DOI 37 
DOI "H2'2" 2H2* H 0 0 N N N 61.476 64.719 34.475 -0.495 3.024  -0.989 "H2'2" DOI 38 
DOI "H3'"  H3*  H 0 1 N N N 60.960 67.168 35.686 -2.552 1.357  -2.226 "H3'"  DOI 39 
DOI "HO3'" *HO3 H 0 0 N N N 61.819 67.137 33.706 -2.444 3.657  -2.244 "HO3'" DOI 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 
DOI PA    O1A    DOUB N N 1  
DOI PA    O2A    SING N N 2  
DOI PA    O3A    SING N N 3  
DOI PA    "O5'"  SING N N 4  
DOI O2A   H2A    SING N N 5  
DOI O3A   H3A    SING N N 6  
DOI "O5'" "C5'"  SING N N 7  
DOI P6    O16    DOUB N N 8  
DOI P6    O26    SING N N 9  
DOI P6    O36    SING N N 10 
DOI P6    O6     SING N N 11 
DOI O26   H26    SING N N 12 
DOI O36   H36    SING N N 13 
DOI "C5'" "C4'"  SING N N 14 
DOI "C5'" "H5'1" SING N N 15 
DOI "C5'" "H5'2" SING N N 16 
DOI "C4'" "O4'"  SING N N 17 
DOI "C4'" "C3'"  SING N N 18 
DOI "C4'" "H4'"  SING N N 19 
DOI "O4'" "C1'"  SING N N 20 
DOI "C1'" N9     SING N N 21 
DOI "C1'" "C2'"  SING N N 22 
DOI "C1'" "H1'"  SING N N 23 
DOI N9    C4     SING Y N 24 
DOI N9    C8     SING Y N 25 
DOI C4    N3     DOUB Y N 26 
DOI C4    C5     SING Y N 27 
DOI N3    C2     SING Y N 28 
DOI C2    N1     DOUB Y N 29 
DOI C2    H2     SING N N 30 
DOI N1    C6     SING Y N 31 
DOI C6    O6     SING N N 32 
DOI C6    C5     DOUB Y N 33 
DOI C5    N7     SING Y N 34 
DOI N7    C8     DOUB Y N 35 
DOI C8    H8     SING N N 36 
DOI "C2'" "C3'"  SING N N 37 
DOI "C2'" "H2'1" SING N N 38 
DOI "C2'" "H2'2" SING N N 39 
DOI "C3'" "O3'"  SING N N 40 
DOI "C3'" "H3'"  SING N N 41 
DOI "O3'" "HO3'" SING N N 42 
# 
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 
DOI SMILES           ACDLabs              10.04 O=P(O)(O)Oc3ncnc1c3ncn1C2OC(C(O)C2)COP(=O)(O)O                                                                                                                               
DOI InChI            InChI                1.02b InChI=1/C10H14N4O10P2/c15-5-1-7(23-6(5)2-22-25(16,17)18)14-4-13-8-9(14)11-3-12-10(8)24-26(19,20)21/h3-7,15H,1-2H2,(H2,16,17,18)(H2,19,20,21)/t5-,6+,7+/m0/s1/f/h16-17,19-20H 
DOI InChIKey         InChI                1.02b GEECATYOCBMMIR-OSRYPQQUDL                                                                                                                                                    
DOI SMILES_CANONICAL CACTVS               3.341 O[C@H]1C[C@@H](O[C@@H]1CO[P](O)(O)=O)n2cnc3c(O[P](O)(O)=O)ncnc23                                                                                                             
DOI SMILES           CACTVS               3.341 O[CH]1C[CH](O[CH]1CO[P](O)(O)=O)n2cnc3c(O[P](O)(O)=O)ncnc23                                                                                                                  
DOI SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1nc2c(c(n1)OP(=O)(O)O)ncn2[C@H]3C[C@@H]([C@H](O3)COP(=O)(O)O)O                                                                                                              
DOI SMILES           "OpenEye OEToolkits" 1.5.0 c1nc2c(c(n1)OP(=O)(O)O)ncn2C3CC(C(O3)COP(=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 
DOI "SYSTEMATIC NAME" ACDLabs              10.04 9-(2-deoxy-5-O-phosphono-beta-D-erythro-pentofuranosyl)-6-(phosphonooxy)-9H-purine          
DOI "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,5R)-3-hydroxy-5-(6-phosphonooxypurin-9-yl)oxolan-2-yl]methyl dihydrogen phosphate" 
# 
