data_A22
# 
_chem_comp.id                                    A22 
_chem_comp.name                                  "[(2R,3S,4R,5R)-5-(6-AMINO-9H-PURIN-9-YL)-3,4-DIHYDROXYTETRAHYDROFURAN-2-YL]METHYL [(2R,3R,4R,5R)-5-(6-AMINO-9H-PURIN-9-YL)-3-HYDROXY-4-(PHOSPHONOOXY)TETRAHYDROFURAN-2-YL]METHYL DIHYDROGEN DIPHOSPHATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H27 N10 O16 P3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         
;2'-PHOSPHATE BIS(ADENOSINE)-5'-DIPHOSPHATE
;
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-10-25 
_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                        756.407 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     A22 
_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   N 
_chem_comp.pdbx_model_coordinates_db_code        ? 
_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 
A22 P2D  P2*A P 0 1 N N N 17.279 9.952  17.697 -3.169  -0.690 -4.227 P2D  A22 1  
A22 O11  O1PA O 0 1 N N N 18.069 10.805 18.807 -4.737  -0.340 -4.046 O11  A22 2  
A22 O12  O2PA O 0 1 N N N 17.239 8.411  18.202 -3.184  -1.953 -5.236 O12  A22 3  
A22 O13  O3PA O 0 1 N N N 15.930 10.498 17.465 -2.301  0.456  -4.659 O13  A22 4  
A22 P1A  P1A  P 0 1 N N S 13.980 7.547  13.320 -3.208  3.260  2.461  P1A  A22 5  
A22 O14  O5PA O 0 1 N N N 13.749 7.656  14.785 -3.184  4.596  1.550  O14  A22 6  
A22 O15  O6PA O 0 1 N N N 13.663 6.269  12.632 -2.840  3.469  3.901  O15  A22 7  
A22 O5D  O5*A O 0 1 N N N 15.505 7.935  12.983 -2.282  2.216  1.644  O5D  A22 8  
A22 C5D  C5*A C 0 1 N N N 16.531 6.899  12.992 -2.577  1.974  0.279  C5D  A22 9  
A22 C4D  C4*A C 0 1 N N R 17.851 7.350  13.677 -1.579  0.965  -0.273 C4D  A22 10 
A22 O4D  O4*A O 0 1 N N N 18.380 8.512  12.974 -1.730  -0.273 0.460  O4D  A22 11 
A22 C3D  C3*A C 0 1 N N R 17.659 7.802  15.138 -1.823  0.630  -1.741 C3D  A22 12 
A22 O3D  O3*A O 0 1 N N N 18.707 7.217  15.919 -0.592  0.209  -2.327 O3D  A22 13 
A22 C2D  C2*A C 0 1 N N R 17.800 9.339  15.086 -2.770  -0.551 -1.650 C2D  A22 14 
A22 O2D  O2*A O 0 1 N N N 18.261 9.900  16.361 -2.758  -1.359 -2.809 O2D  A22 15 
A22 C1D  C1*A C 0 1 N N R 18.854 9.440  13.991 -2.219  -1.287 -0.439 C1D  A22 16 
A22 N9A  N9A  N 0 1 Y N N 19.094 10.768 13.319 -3.202  -2.122 0.248  N9A  A22 17 
A22 C8A  C8A  C 0 1 Y N N 18.224 11.703 12.914 -3.417  -3.459 0.034  C8A  A22 18 
A22 N7A  N7A  N 0 1 Y N N 18.896 12.732 12.373 -4.371  -3.939 0.804  N7A  A22 19 
A22 C5A  C5A  C 0 1 Y N N 20.207 12.426 12.404 -4.794  -2.868 1.550  C5A  A22 20 
A22 C6A  C6A  C 0 1 Y N N 21.392 13.047 11.986 -5.769  -2.735 2.533  C6A  A22 21 
A22 N6A  N6A  N 0 1 N N N 21.406 14.247 11.388 -6.542  -3.840 2.931  N6A  A22 22 
A22 N1A  N1A  N 0 1 Y N N 22.554 12.389 12.193 -5.967  -1.524 3.107  N1A  A22 23 
A22 C2A  C2A  C 0 1 Y N N 22.606 11.219 12.794 -5.191  -0.497 2.682  C2A  A22 24 
A22 N3A  N3A  N 0 1 Y N N 21.516 10.591 13.194 -4.220  -0.501 1.743  N3A  A22 25 
A22 C4A  C4A  C 0 1 Y N N 20.315 11.169 12.998 -4.079  -1.727 1.219  C4A  A22 26 
A22 P1B  P1B  P 0 1 N N R 13.292 10.288 12.736 -6.146  3.289  2.624  P1B  A22 27 
A22 O16  O1PB O 0 1 N N N 14.454 10.563 13.612 -6.240  4.640  1.739  O16  A22 28 
A22 O17  O2PB O 0 1 N N N 11.975 10.893 13.033 -6.338  3.500  4.098  O17  A22 29 
A22 O18  O3PB O 0 1 N N N 13.082 8.685  12.587 -4.700  2.686  2.225  O18  A22 30 
A22 O5E  O5*B O 0 1 N N N 13.680 10.719 11.201 -7.210  2.282  1.938  O5E  A22 31 
A22 C5E  C5*B C 0 1 N N N 13.955 9.745  10.213 -7.130  2.004  0.551  C5E  A22 32 
A22 C4E  C4*B C 0 1 N N R 15.460 9.708  9.925  -8.524  1.708  0.025  C4E  A22 33 
A22 O4E  O4*B O 0 1 N N N 15.997 8.340  9.974  -8.456  1.375  -1.371 O4E  A22 34 
A22 C3E  C3*B C 0 1 N N S 15.525 10.118 8.457  -9.180  0.510  0.689  C3E  A22 35 
A22 O3E  O3*B O 0 1 N N N 15.599 11.564 8.353  -9.747  0.839  1.939  O3E  A22 36 
A22 C2E  C2*B C 0 1 N N R 16.807 9.426  7.972  -10.204 0.087  -0.348 C2E  A22 37 
A22 O2E  O2*B O 0 1 N N N 17.869 10.391 8.059  -11.405 0.846  -0.225 O2E  A22 38 
A22 C1E  C1*B C 0 1 N N R 17.043 8.241  8.949  -9.516  0.441  -1.668 C1E  A22 39 
A22 N9B  N9B  N 0 1 Y N N 16.997 6.838  8.340  -8.963  -0.718 -2.370 N9B  A22 40 
A22 C8B  C8B  C 0 1 Y N N 15.919 6.218  7.837  -7.722  -1.266 -2.174 C8B  A22 41 
A22 N7B  N7B  N 0 1 Y N N 16.261 4.997  7.411  -7.507  -2.303 -2.955 N7B  A22 42 
A22 C5B  C5B  C 0 1 Y N N 17.567 4.827  7.628  -8.657  -2.434 -3.691 C5B  A22 43 
A22 C6B  C6B  C 0 1 Y N N 18.479 3.785  7.389  -9.041  -3.336 -4.679 C6B  A22 44 
A22 N6B  N6B  N 0 1 N N N 18.127 2.621  6.819  -8.172  -4.359 -5.094 N6B  A22 45 
A22 N1B  N1B  N 0 1 Y N N 19.753 3.968  7.756  -10.269 -3.216 -5.238 N1B  A22 46 
A22 C2B  C2B  C 0 1 Y N N 20.147 5.108  8.318  -11.063 -2.211 -4.797 C2B  A22 47 
A22 N3B  N3B  N 0 1 Y N N 19.320 6.098  8.563  -10.804 -1.280 -3.852 N3B  A22 48 
A22 C4B  C4B  C 0 1 Y N N 18.024 5.995  8.228  -9.576  -1.458 -3.343 C4B  A22 49 
A22 H1PA H1PA H 0 0 N N N 18.225 10.263 19.572 -5.200  0.145  -4.761 H1PA A22 50 
A22 H2PA H2PA H 0 0 N N N 17.231 7.831  17.450 -3.318  -1.793 -6.195 H2PA A22 51 
A22 H5PA H5PA H 0 0 N N N 14.584 7.679  15.237 -2.402  5.187  1.592  H5PA A22 52 
A22 HD1  1H*A H 0 1 N N N 16.138 6.030  13.540 -3.597  1.587  0.203  HD1  A22 53 
A22 HD2  2H*A H 0 1 N N N 16.768 6.662  11.944 -2.510  2.919  -0.268 HD2  A22 54 
A22 H4D  H4*A H 0 1 N N N 18.518 6.476  13.650 -0.562  1.330  -0.099 H4D  A22 55 
A22 H3CA H3CA H 0 0 N N N 16.697 7.504  15.581 -2.209  1.461  -2.337 H3CA A22 56 
A22 H3OA H3OA H 0 0 N N N 19.474 7.087  15.374 -0.823  -0.417 -3.030 H3OA A22 57 
A22 H2D  H2*A H 0 1 N N N 16.869 9.895  14.899 -3.794  -0.204 -1.468 H2D  A22 58 
A22 H1D  H1*A H 0 1 N N N 19.823 9.240  14.471 -1.395  -1.962 -0.695 H1D  A22 59 
A22 H8A  H8A  H 0 1 N N N 17.150 11.639 13.008 -2.849  -4.026 -0.692 H8A  A22 60 
A22 H6A1 1H6A H 0 0 N N N 21.409 14.966 12.083 -6.351  -4.285 3.808  H6A1 A22 61 
A22 H6A2 2H6A H 0 0 N N N 22.226 14.327 10.821 -7.211  -4.228 2.293  H6A2 A22 62 
A22 H2A  H2A  H 0 1 N N N 23.568 10.760 12.965 -5.377  0.458  3.162  H2A  A22 63 
A22 H1PB H1PB H 0 0 N N N 15.242 10.622 13.085 -6.977  5.266  1.906  H1PB A22 64 
A22 HE1  1H*B H 0 1 N N N 13.413 9.999  9.290  -6.704  2.873  0.041  HE1  A22 65 
A22 HE2  2H*B H 0 1 N N N 13.630 8.758  10.575 -6.473  1.143  0.402  HE2  A22 66 
A22 H4E  H4*B H 0 1 N N N 16.017 10.327 10.644 -9.139  2.609  0.134  H4E  A22 67 
A22 H3CB H3CB H 0 0 N N N 14.648 9.830  7.859  -8.447  -0.294 0.830  H3CB A22 68 
A22 H3OB H3OB H 0 0 N N N 15.615 11.944 9.223  -9.060  1.308  2.436  H3OB A22 69 
A22 H2CB H2CB H 0 0 N N N 16.750 9.056  6.938  -10.482 -0.967 -0.259 H2CB A22 70 
A22 H2OB H2OB H 0 0 N N N 18.176 10.604 7.186  -11.802 0.622  0.635  H2OB A22 71 
A22 H1E  H1*B H 0 1 N N N 18.071 8.341  9.327  -10.198 0.912  -2.383 H1E  A22 72 
A22 H8B  H8B  H 0 1 N N N 14.926 6.640  7.784  -7.024  -0.866 -1.450 H8B  A22 73 
A22 H6B1 1H6B H 0 0 N N N 18.040 2.746  5.831  -8.540  -5.147 -5.592 H6B1 A22 74 
A22 H6B2 2H6B H 0 0 N N N 18.828 1.933  7.007  -7.211  -4.336 -4.807 H6B2 A22 75 
A22 H2B  H2B  H 0 1 N N N 21.188 5.223  8.583  -12.038 -2.144 -5.267 H2B  A22 76 
# 
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 
A22 P2D O2D  SING N N 1  
A22 P2D O13  DOUB N N 2  
A22 P2D O12  SING N N 3  
A22 P2D O11  SING N N 4  
A22 O11 H1PA SING N N 5  
A22 O12 H2PA SING N N 6  
A22 P1A O18  SING N N 7  
A22 P1A O15  DOUB N N 8  
A22 P1A O5D  SING N N 9  
A22 P1A O14  SING N N 10 
A22 O14 H5PA SING N N 11 
A22 O5D C5D  SING N N 12 
A22 C5D C4D  SING N N 13 
A22 C5D HD1  SING N N 14 
A22 C5D HD2  SING N N 15 
A22 C4D O4D  SING N N 16 
A22 C4D C3D  SING N N 17 
A22 C4D H4D  SING N N 18 
A22 O4D C1D  SING N N 19 
A22 C3D C2D  SING N N 20 
A22 C3D O3D  SING N N 21 
A22 C3D H3CA SING N N 22 
A22 O3D H3OA SING N N 23 
A22 C2D C1D  SING N N 24 
A22 C2D O2D  SING N N 25 
A22 C2D H2D  SING N N 26 
A22 C1D N9A  SING N N 27 
A22 C1D H1D  SING N N 28 
A22 N9A C8A  SING Y N 29 
A22 N9A C4A  SING Y N 30 
A22 C8A N7A  DOUB Y N 31 
A22 C8A H8A  SING N N 32 
A22 N7A C5A  SING Y N 33 
A22 C5A C6A  SING Y N 34 
A22 C5A C4A  DOUB Y N 35 
A22 C6A N6A  SING N N 36 
A22 C6A N1A  DOUB Y N 37 
A22 N6A H6A1 SING N N 38 
A22 N6A H6A2 SING N N 39 
A22 N1A C2A  SING Y N 40 
A22 C2A N3A  DOUB Y N 41 
A22 C2A H2A  SING N N 42 
A22 N3A C4A  SING Y N 43 
A22 P1B O5E  SING N N 44 
A22 P1B O18  SING N N 45 
A22 P1B O17  DOUB N N 46 
A22 P1B O16  SING N N 47 
A22 O16 H1PB SING N N 48 
A22 O5E C5E  SING N N 49 
A22 C5E C4E  SING N N 50 
A22 C5E HE1  SING N N 51 
A22 C5E HE2  SING N N 52 
A22 C4E C3E  SING N N 53 
A22 C4E O4E  SING N N 54 
A22 C4E H4E  SING N N 55 
A22 O4E C1E  SING N N 56 
A22 C3E C2E  SING N N 57 
A22 C3E O3E  SING N N 58 
A22 C3E H3CB SING N N 59 
A22 O3E H3OB SING N N 60 
A22 C2E O2E  SING N N 61 
A22 C2E C1E  SING N N 62 
A22 C2E H2CB SING N N 63 
A22 O2E H2OB SING N N 64 
A22 C1E N9B  SING N N 65 
A22 C1E H1E  SING N N 66 
A22 N9B C8B  SING Y N 67 
A22 N9B C4B  SING Y N 68 
A22 C8B N7B  DOUB Y N 69 
A22 C8B H8B  SING N N 70 
A22 N7B C5B  SING Y N 71 
A22 C5B C6B  DOUB Y N 72 
A22 C5B C4B  SING Y N 73 
A22 C6B N6B  SING N N 74 
A22 C6B N1B  SING Y N 75 
A22 N6B H6B1 SING N N 76 
A22 N6B H6B2 SING N N 77 
A22 N1B C2B  DOUB Y N 78 
A22 C2B N3B  SING Y N 79 
A22 C2B H2B  SING N N 80 
A22 N3B C4B  DOUB Y N 81 
# 
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 
A22 SMILES           ACDLabs              10.04 O=P(O)(OCC3OC(n1c2ncnc(N)c2nc1)C(O)C3O)OP(=O)(O)OCC6OC(n5cnc4c(ncnc45)N)C(OP(=O)(O)O)C6O 
A22 InChI            InChI                1.02b 
;InChI=1/C20H27N10O16P3/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(43-19)1-41-48(37,38)46-49(39,40)42-2-8-12(32)14(45-47(34,35)36)20(44-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-33H,1-2H2,(H,37,38)(H,39,40)(H2,21,23,25)(H2,22,24,26)(H2,34,35,36)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1/f/h34-35,37,39H,21-22H2
;
A22 InChIKey         InChI                1.02b JRSFRHPGKHPNEL-SLAMVQDSDR 
A22 SMILES_CANONICAL CACTVS               3.341 Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P@@](O)(=O)O[P@@](O)(=O)OC[C@H]4O[C@H]([C@H](O[P](O)(O)=O)[C@@H]4O)n5cnc6c(N)ncnc56)[C@@H](O)[C@H]3O 
A22 SMILES           CACTVS               3.341 Nc1ncnc2n(cnc12)[CH]3O[CH](CO[P](O)(=O)O[P](O)(=O)OC[CH]4O[CH]([CH](O[P](O)(O)=O)[CH]4O)n5cnc6c(N)ncnc56)[CH](O)[CH]3O 
A22 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]([C@@H](O4)n5cnc6c5ncnc6N)OP(=O)(O)O)O)O)O)N 
A22 SMILES           "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COP(=O)(O)OP(=O)(O)OCC4C(C(C(O4)n5cnc6c5ncnc6N)OP(=O)(O)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 
A22 "SYSTEMATIC NAME" ACDLabs              10.04 
"[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl [(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)tetrahydrofuran-2-yl]methyl dihydrogen diphosphate (non-preferred name)" 
A22 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl] [(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxy-oxolan-2-yl]methyl hydrogen phosphate" 
# 
