data_A1R
# 
_chem_comp.id                                    A1R 
_chem_comp.name                                  "5'-O-[(S)-{[(S)-{[(2R,3R,4S)-3,4-DIHYDROXYPYRROLIDIN-2-YL]METHOXY}(HYDROXY)PHOSPHORYL]OXY}(HYDROXY)PHOSPHORYL]ADENOSINE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C15 H24 N6 O12 P2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-01-09 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        542.332 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     A1R 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "OpenEye/OEToolkits V1.4.2" 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        ? 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
A1R N1     N1   N 0 1 Y N N 39.986 59.435 23.849 7.220  2.227 2.485  N1     A1R 1  
A1R C2     C2   C 0 1 Y N N 41.075 60.308 24.105 6.460  1.535 3.369  C2     A1R 2  
A1R N3     N3   N 0 1 Y N N 41.421 60.754 25.452 5.120  1.367 3.384  N3     A1R 3  
A1R C4     C4   C 0 1 Y N N 40.559 60.227 26.486 4.555  2.007 2.350  C4     A1R 4  
A1R C5     C5   C 0 1 Y N N 39.456 59.361 26.349 5.197  2.750 1.372  C5     A1R 5  
A1R C6     C6   C 0 1 Y N N 39.160 58.948 24.940 6.582  2.849 1.465  C6     A1R 6  
A1R N6     N6   N 0 1 N N N 38.092 58.078 24.601 7.315  3.582 0.515  N6     A1R 7  
A1R N7     N7   N 0 1 Y N N 38.893 59.088 27.584 4.292  3.258 0.474  N7     A1R 8  
A1R C8     C8   C 0 1 Y N N 39.633 59.765 28.469 3.121  2.831 0.899  C8     A1R 9  
A1R N9     N9   N 0 1 Y N N 40.662 60.475 27.845 3.227  2.069 2.033  N9     A1R 10 
A1R "C1'"  C1*  C 0 1 N N R 41.730 61.340 28.367 2.122  1.444 2.758  "C1'"  A1R 11 
A1R "C2'"  C2*  C 0 1 N N R 41.489 62.285 29.469 1.457  2.354 3.779  "C2'"  A1R 12 
A1R "O2'"  O2*  O 0 1 N N N 41.264 63.633 28.973 2.147  2.354 5.013  "O2'"  A1R 13 
A1R "C3'"  C3*  C 0 1 N N S 42.681 62.187 30.352 0.074  1.742 3.873  "C3'"  A1R 14 
A1R "O3'"  O3*  O 0 1 N N N 43.648 63.258 30.222 0.127  0.567 4.682  "O3'"  A1R 15 
A1R "O4'"  O4*  O 0 1 N N N 42.710 60.432 28.790 1.089  1.060 1.831  "O4'"  A1R 16 
A1R "C4'"  C4*  C 0 1 N N R 43.344 60.862 30.015 -0.199 1.333 2.429  "C4'"  A1R 17 
A1R "C5'"  C5*  C 0 1 N N N 43.174 59.708 31.057 -0.881 2.428 1.621  "C5'"  A1R 18 
A1R "O5'"  O5*  O 0 1 N N N 43.773 60.105 32.332 -2.127 2.738 2.221  "O5'"  A1R 19 
A1R PA     PA   P 0 1 N N S 43.794 59.187 33.573 -3.048 3.881 1.542  PA     A1R 20 
A1R O1A    O1A  O 0 1 N N N 42.450 58.701 33.941 -4.356 4.166 2.221  O1A    A1R 21 
A1R O2A    O2A  O 0 1 N N N 44.453 59.921 34.664 -3.167 3.431 -0.007 O2A    A1R 22 
A1R O3A    O3A  O 0 1 N N N 44.752 58.010 33.379 -2.017 5.125 1.494  O3A    A1R 23 
A1R PB     PB   P 0 1 N N S 46.166 57.737 32.996 -2.158 6.595 0.835  PB     A1R 24 
A1R O1B    O1B  O 0 1 N N N 46.859 58.991 32.691 -3.349 7.273 1.695  O1B    A1R 25 
A1R O2B    O2B  O 0 1 N N N 46.471 56.956 31.873 -2.392 6.585 -0.648 O2B    A1R 26 
A1R O5N    O5N  O 0 1 N N N 46.577 57.356 34.413 -0.823 7.380 1.306  O5N    A1R 27 
A1R C5N    C5N  C 0 1 N N N 46.305 56.333 35.251 -0.495 7.458 2.682  C5N    A1R 28 
A1R N4N    N4N  N 0 1 N N N 45.254 55.296 36.790 1.451  7.598 4.225  N4N    A1R 29 
A1R C1N    C1N  C 0 1 N N N 45.826 54.816 38.076 2.584  6.673 4.407  C1N    A1R 30 
A1R O2N    O2N  O 0 1 N N N 45.655 56.299 39.430 3.942  7.281 2.533  O2N    A1R 31 
A1R C2N    C2N  C 0 1 N N S 46.699 55.757 38.571 3.036  6.292 3.009  C2N    A1R 32 
A1R O3N    O3N  O 0 1 N N N 46.716 58.282 38.148 1.955  6.427 0.846  O3N    A1R 33 
A1R C3N    C3N  C 0 1 N N R 46.824 56.923 37.729 1.729  6.314 2.237  C3N    A1R 34 
A1R C4N    C4N  C 0 1 N N R 45.891 56.638 36.568 1.021  7.534 2.818  C4N    A1R 35 
A1R H2     H2   H 0 1 N N N 41.670 60.655 23.273 7.003  1.049 4.172  H2     A1R 36 
A1R HN61   1HN6 H 0 0 N N N 37.556 57.873 25.420 6.827  4.088 -0.199 HN61   A1R 37 
A1R HN62   2HN6 H 0 0 N N N 37.506 58.519 23.921 8.315  3.515 0.506  HN62   A1R 38 
A1R H8     H8   H 0 1 N N N 39.457 59.763 29.535 2.168  3.039 0.431  H8     A1R 39 
A1R "H1'"  H1*  H 0 1 N N N 41.955 62.039 27.548 2.547  0.542 3.211  "H1'"  A1R 40 
A1R "H2'"  H2*  H 0 1 N N N 40.575 62.038 30.028 1.394  3.384 3.408  "H2'"  A1R 41 
A1R "HO2'" HO2* H 0 0 N N N 41.215 64.236 29.705 2.020  1.477 5.414  "HO2'" A1R 42 
A1R "H3'"  H3*  H 0 1 N N N 42.334 62.264 31.393 -0.677 2.410 4.304  "H3'"  A1R 43 
A1R "HO3'" HO3* H 0 0 N N N 43.860 63.600 31.083 0.225  0.870 5.597  "HO3'" A1R 44 
A1R "H4'"  H4*  H 0 1 N N N 44.428 61.042 29.971 -0.793 0.416 2.368  "H4'"  A1R 45 
A1R "H5'1" 1H5* H 0 0 N N N 42.103 59.503 31.204 -1.058 2.094 0.594  "H5'1" A1R 46 
A1R "H5'2" 2H5* H 0 0 N N N 43.675 58.803 30.684 -0.265 3.332 1.602  "H5'2" A1R 47 
A1R HO2A   HO2A H 0 0 N N N 44.595 59.336 35.399 -3.727 3.960 -0.614 HO2A   A1R 48 
A1R HO1B   HO1B H 0 0 N N N 47.009 59.474 33.495 -3.718 8.132 1.397  HO1B   A1R 49 
A1R H5N1   1H5N H 0 0 N N N 45.489 55.757 34.790 -0.954 8.349 3.111  H5N1   A1R 50 
A1R H5N2   2H5N H 0 0 N N N 47.267 55.814 35.376 -0.872 6.570 3.192  H5N2   A1R 51 
A1R HN4N   HN4N H 0 0 N N N 44.259 55.375 36.846 0.692  7.332 4.851  HN4N   A1R 52 
A1R H1N1   1H1N H 0 0 N N N 45.014 54.653 38.800 2.231  5.784 4.943  H1N1   A1R 53 
A1R H1N2   2H1N H 0 0 N N N 46.363 53.871 37.908 3.372  7.152 4.994  H1N2   A1R 54 
A1R HO2N   HO2N H 0 0 N N N 45.997 56.417 40.309 3.594  8.139 2.822  HO2N   A1R 55 
A1R H2N    H2N  H 0 1 N N N 47.690 55.368 38.848 3.537  5.321 2.965  H2N    A1R 56 
A1R HO3N   HO3N H 0 0 N N N 46.692 58.320 39.097 2.184  7.355 0.665  HO3N   A1R 57 
A1R H3N    H3N  H 0 1 N N N 47.911 56.983 37.573 1.158  5.398 2.431  H3N    A1R 58 
A1R H4N    H4N  H 0 1 N N N 45.379 57.612 36.587 1.355  8.445 2.307  H4N    A1R 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 
A1R N1    C2     DOUB Y N 1  
A1R N1    C6     SING Y N 2  
A1R C2    N3     SING Y N 3  
A1R C2    H2     SING N N 4  
A1R N3    C4     DOUB Y N 5  
A1R C4    C5     SING Y N 6  
A1R C4    N9     SING Y N 7  
A1R C5    C6     DOUB Y N 8  
A1R C5    N7     SING Y N 9  
A1R C6    N6     SING N N 10 
A1R N6    HN61   SING N N 11 
A1R N6    HN62   SING N N 12 
A1R N7    C8     DOUB Y N 13 
A1R C8    N9     SING Y N 14 
A1R C8    H8     SING N N 15 
A1R N9    "C1'"  SING N N 16 
A1R "C1'" "O4'"  SING N N 17 
A1R "C1'" "C2'"  SING N N 18 
A1R "C1'" "H1'"  SING N N 19 
A1R "C2'" "O2'"  SING N N 20 
A1R "C2'" "C3'"  SING N N 21 
A1R "C2'" "H2'"  SING N N 22 
A1R "O2'" "HO2'" SING N N 23 
A1R "C3'" "C4'"  SING N N 24 
A1R "C3'" "O3'"  SING N N 25 
A1R "C3'" "H3'"  SING N N 26 
A1R "O3'" "HO3'" SING N N 27 
A1R "O4'" "C4'"  SING N N 28 
A1R "C4'" "C5'"  SING N N 29 
A1R "C4'" "H4'"  SING N N 30 
A1R "C5'" "O5'"  SING N N 31 
A1R "C5'" "H5'1" SING N N 32 
A1R "C5'" "H5'2" SING N N 33 
A1R "O5'" PA     SING N N 34 
A1R PA    O3A    SING N N 35 
A1R PA    O1A    DOUB N N 36 
A1R PA    O2A    SING N N 37 
A1R O2A   HO2A   SING N N 38 
A1R O3A   PB     SING N N 39 
A1R PB    O2B    DOUB N N 40 
A1R PB    O1B    SING N N 41 
A1R PB    O5N    SING N N 42 
A1R O1B   HO1B   SING N N 43 
A1R O5N   C5N    SING N N 44 
A1R C5N   C4N    SING N N 45 
A1R C5N   H5N1   SING N N 46 
A1R C5N   H5N2   SING N N 47 
A1R N4N   C4N    SING N N 48 
A1R N4N   C1N    SING N N 49 
A1R N4N   HN4N   SING N N 50 
A1R C1N   C2N    SING N N 51 
A1R C1N   H1N1   SING N N 52 
A1R C1N   H1N2   SING N N 53 
A1R O2N   C2N    SING N N 54 
A1R O2N   HO2N   SING N N 55 
A1R C2N   C3N    SING N N 56 
A1R C2N   H2N    SING N N 57 
A1R O3N   C3N    SING N N 58 
A1R O3N   HO3N   SING N N 59 
A1R C3N   C4N    SING N N 60 
A1R C3N   H3N    SING N N 61 
A1R C4N   H4N    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 
A1R SMILES           ACDLabs              10.04 O=P(O)(OCC1NCC(O)C1O)OP(=O)(O)OCC4OC(n3cnc2c(ncnc23)N)C(O)C4O 
A1R InChI            InChI                1.02b 
InChI=1/C15H24N6O12P2/c16-13-9-14(19-4-18-13)21(5-20-9)15-12(25)11(24)8(32-15)3-31-35(28,29)33-34(26,27)30-2-6-10(23)7(22)1-17-6/h4-8,10-12,15,17,22-25H,1-3H2,(H,26,27)(H,28,29)(H2,16,18,19)/t6-,7+,8-,10-,11-,12-,15-/m1/s1/f/h26,28H,16H2 
A1R InChIKey         InChI                1.02b NDQDTBCXPOIQGT-SRXLMFHVDE 
A1R SMILES_CANONICAL CACTVS               3.341 Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P@@](O)(=O)O[P@](O)(=O)OC[C@H]4NC[C@H](O)[C@@H]4O)[C@@H](O)[C@H]3O 
A1R SMILES           CACTVS               3.341 Nc1ncnc2n(cnc12)[CH]3O[CH](CO[P](O)(=O)O[P](O)(=O)OC[CH]4NC[CH](O)[CH]4O)[CH](O)[CH]3O 
A1R SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO[P@](=O)(O)O[P@@](=O)(O)OC[C@@H]4[C@H]([C@H](CN4)O)O)O)O)N 
A1R SMILES           "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COP(=O)(O)OP(=O)(O)OCC4C(C(CN4)O)O)O)O)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 
A1R "SYSTEMATIC NAME" ACDLabs              10.04 "5'-O-[(S)-{[(S)-{[(2R,3R,4S)-3,4-dihydroxypyrrolidin-2-yl]methoxy}(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]adenosine"                                        
A1R "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methyl [[(2R,3R,4S)-3,4-dihydroxypyrrolidin-2-yl]methoxy-hydroxy-phosphoryl] hydrogen phosphate" 
# 
