data_A2R
# 
_chem_comp.id                                    A2R 
_chem_comp.name                                  "[(2R,3R,4R,5R)-5-(6-AMINO-9H-PURIN-9-YL)-3-HYDROXY-4-(PHOSPHONOOXY)TETRAHYDROFURAN-2-YL]METHYL [(2R,3S,4R,5R)-3,4,5-TRIHYDROXYTETRAHYDROFURAN-2-YL]METHYL DIHYDROGEN DIPHOSPHATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C15 H24 N5 O17 P3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-05-24 
_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                        639.296 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     A2R 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "Corina V3.40" 
_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 
A2R OP3    OP3  O 0 1 N N N 14.631 30.053 24.165 7.316   -0.045 -0.705 OP3    A2R 1  
A2R "P2'"  P2*  P 0 1 N N N 14.962 30.355 22.713 6.771   -1.485 -1.175 "P2'"  A2R 2  
A2R OP1    OP1  O 0 1 N N N 14.065 31.362 22.029 7.422   -1.867 -2.597 OP1    A2R 3  
A2R OP2    OP2  O 0 1 N N N 15.220 29.134 21.844 7.146   -2.506 -0.171 OP2    A2R 4  
A2R "O2'"  O2*  O 0 1 N N N 16.370 31.139 22.863 5.168   -1.433 -1.314 "O2'"  A2R 5  
A2R "C2'"  C2*  C 0 1 N N R 17.615 30.492 23.104 4.297   -1.222 -0.202 "C2'"  A2R 6  
A2R "C1'"  C1*  C 0 1 N N R 18.611 31.086 22.119 3.451   0.053  -0.410 "C1'"  A2R 7  
A2R N9     N9   N 0 1 Y N N 18.482 30.450 20.802 4.042   1.181  0.314  N9     A2R 8  
A2R C4     C4   C 0 1 Y N N 18.333 31.167 19.678 5.042   2.003  -0.139 C4     A2R 9  
A2R N3     N3   N 0 1 Y N N 18.329 32.521 19.443 5.760   2.080  -1.256 N3     A2R 10 
A2R C2     C2   C 0 1 Y N N 18.167 32.977 18.190 6.679   3.011  -1.400 C2     A2R 11 
A2R N1     N1   N 0 1 Y N N 18.020 32.135 17.153 6.935   3.905  -0.462 N1     A2R 12 
A2R C6     C6   C 0 1 Y N N 18.016 30.771 17.353 6.269   3.907  0.688  C6     A2R 13 
A2R N6     N6   N 0 1 N N N 17.856 29.921 16.315 6.544   4.848  1.664  N6     A2R 14 
A2R C5     C5   C 0 1 Y N N 18.177 30.267 18.641 5.277   2.931  0.888  C5     A2R 15 
A2R N7     N7   N 0 1 Y N N 18.213 29.015 19.178 4.424   2.634  1.898  N7     A2R 16 
A2R C8     C8   C 0 1 Y N N 18.420 29.119 20.513 3.694   1.610  1.561  C8     A2R 17 
A2R "O4'"  O4*  O 0 1 N N N 19.857 30.992 22.740 2.154   -0.271 0.135  "O4'"  A2R 18 
A2R "C3'"  C3*  C 0 1 N N R 18.208 30.854 24.450 3.250   -2.356 -0.112 "C3'"  A2R 19 
A2R "O3'"  O3*  O 0 1 N N N 17.561 32.005 25.030 3.444   -3.301 -1.166 "O3'"  A2R 20 
A2R "C4'"  C4*  C 0 1 N N R 19.664 31.193 24.129 1.896   -1.631 -0.276 "C4'"  A2R 21 
A2R "C5'"  C5*  C 0 1 N N N 20.612 30.269 24.868 0.837   -2.269 0.625  "C5'"  A2R 22 
A2R "O5'"  O5*  O 0 1 N N N 20.388 30.462 26.257 -0.416  -1.612 0.426  "O5'"  A2R 23 
A2R P      P    P 0 1 N N S 20.339 29.224 27.295 -1.758  -2.026 1.213  P      A2R 24 
A2R O1     O1   O 0 1 N N N 19.812 28.006 26.584 -1.507  -1.982 2.671  O1     A2R 25 
A2R O2     O2   O 0 1 N N N 19.594 29.699 28.521 -2.192  -3.517 0.788  O2     A2R 26 
A2R O3     O3   O 0 1 N N N 21.885 28.931 27.567 -2.938  -0.996 0.840  O3     A2R 27 
A2R P1     P1   P 0 1 N N S 22.914 29.737 28.477 -4.332  -0.592 1.538  P1     A2R 28 
A2R O11    O11  O 0 1 N N N 23.122 28.906 29.721 -4.051  0.449  2.733  O11    A2R 29 
A2R O12    O12  O 0 1 N N N 22.582 31.206 28.458 -4.981  -1.805 2.083  O12    A2R 30 
A2R "O15'" O15* O 0 0 N N N 24.261 29.569 27.593 -5.300  0.090  0.448  "O15'" A2R 31 
A2R "C15'" C15* C 0 0 N N N 24.815 30.640 26.810 -6.649  0.465  0.731  "C15'" A2R 32 
A2R "C14'" C14* C 0 0 N N R 26.004 30.114 25.990 -7.280  1.083  -0.518 "C14'" A2R 33 
A2R "C13'" C13* C 0 0 N N S 25.569 29.146 24.893 -8.697  1.610  -0.201 "C13'" A2R 34 
A2R "O13'" O13* O 0 0 N N N 26.503 29.218 23.782 -8.666  3.018  0.037  "O13'" A2R 35 
A2R "C12'" C12* C 0 0 N N R 25.683 27.777 25.572 -9.510  1.294  -1.476 "C12'" A2R 36 
A2R "O12'" O12* O 0 0 N N N 25.806 26.701 24.632 -10.005 2.498  -2.065 "O12'" A2R 37 
A2R "C11'" C11* C 0 0 N N R 26.943 27.986 26.413 -8.488  0.614  -2.414 "C11'" A2R 38 
A2R "O14'" O14* O 0 0 N N N 26.882 29.355 26.848 -7.481  0.073  -1.531 "O14'" A2R 39 
A2R "O11'" O11* O 0 0 N N N 27.011 27.097 27.527 -9.115  -0.435 -3.156 "O11'" A2R 40 
A2R HOP3   HOP3 H 0 0 N N N 15.435 29.990 24.667 7.106   0.674  -1.316 HOP3   A2R 41 
A2R HOP1   HOP1 H 0 0 N N N 13.877 32.076 22.626 8.387   -1.916 -2.587 HOP1   A2R 42 
A2R "H2'"  H2*  H 0 1 N N N 17.443 29.408 23.032 4.869   -1.154 0.723  "H2'"  A2R 43 
A2R "H1'"  H1*  H 0 1 N N N 18.432 32.146 21.886 3.370   0.286  -1.472 "H1'"  A2R 44 
A2R H2     H2   H 0 1 N N N 18.155 34.042 18.012 7.244   3.046  -2.319 H2     A2R 45 
A2R HN61   1HN6 H 0 0 N N N 17.816 30.440 15.461 7.231   5.516  1.514  HN61   A2R 46 
A2R HN62   2HN6 H 0 0 N N N 18.627 29.285 16.283 6.051   4.839  2.500  HN62   A2R 47 
A2R H8     H8   H 0 1 N N N 18.517 28.303 21.214 2.928   1.165  2.178  H8     A2R 48 
A2R "H3'"  H3*  H 0 1 N N N 18.091 30.038 25.178 3.304   -2.849 0.859  "H3'"  A2R 49 
A2R "HO3'" HO3* H 0 0 N N N 17.419 31.855 25.957 2.814   -4.034 -1.157 "HO3'" A2R 50 
A2R "H4'"  H4*  H 0 1 N N N 19.867 32.231 24.431 1.576   -1.658 -1.318 "H4'"  A2R 51 
A2R "H5'1" 1H5* H 0 0 N N N 20.415 29.222 24.593 0.737   -3.325 0.376  "H5'1" A2R 52 
A2R "H5'2" 2H5* H 0 0 N N N 21.657 30.493 24.607 1.139   -2.168 1.667  "H5'2" A2R 53 
A2R HO2    HO2  H 0 1 N N N 20.203 29.799 29.243 -2.372  -3.620 -0.156 HO2    A2R 54 
A2R HO11   HO11 H 0 0 N N N 23.166 27.987 29.485 -3.626  1.270  2.448  HO11   A2R 55 
A2R "H5'3" 3H5* H 0 0 N N N 24.045 31.032 26.129 -7.217  -0.417 1.027  "H5'3" A2R 56 
A2R "H5'4" 4H5* H 0 0 N N N 25.158 31.443 27.479 -6.661  1.194  1.542  "H5'4" A2R 57 
A2R "H14'" H14* H 0 0 N N N 26.490 30.997 25.548 -6.653  1.888  -0.901 "H14'" A2R 58 
A2R "H13'" H13* H 0 0 N N N 24.565 29.356 24.495 -9.115  1.087  0.660  "H13'" A2R 59 
A2R "H16'" H16* H 0 0 N N N 26.021 29.234 22.963 -9.530  3.402  0.242  "H16'" A2R 60 
A2R "H12'" H12* H 0 0 N N N 24.798 27.481 26.154 -10.332 0.616  -1.248 "H12'" A2R 61 
A2R "H15'" H15* H 0 0 N N N 25.833 27.052 23.750 -10.523 2.359  -2.870 "H15'" A2R 62 
A2R "H11'" H11* H 0 0 N N N 27.847 27.773 25.824 -8.047  1.346  -3.089 "H11'" A2R 63 
A2R "H17'" H17* H 0 0 N N N 27.026 26.199 27.216 -8.520  -0.898 -3.761 "H17'" A2R 64 
# 
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 
A2R OP3    "P2'"  SING N N 1  
A2R OP3    HOP3   SING N N 2  
A2R "P2'"  OP2    DOUB N N 3  
A2R "P2'"  OP1    SING N N 4  
A2R "P2'"  "O2'"  SING N N 5  
A2R OP1    HOP1   SING N N 6  
A2R "O2'"  "C2'"  SING N N 7  
A2R "C2'"  "C1'"  SING N N 8  
A2R "C2'"  "C3'"  SING N N 9  
A2R "C2'"  "H2'"  SING N N 10 
A2R "C1'"  N9     SING N N 11 
A2R "C1'"  "O4'"  SING N N 12 
A2R "C1'"  "H1'"  SING N N 13 
A2R N9     C4     SING Y N 14 
A2R N9     C8     SING Y N 15 
A2R C4     C5     DOUB Y N 16 
A2R C4     N3     SING Y N 17 
A2R N3     C2     DOUB Y N 18 
A2R C2     N1     SING Y N 19 
A2R C2     H2     SING N N 20 
A2R N1     C6     DOUB Y N 21 
A2R C6     N6     SING N N 22 
A2R C6     C5     SING Y N 23 
A2R N6     HN61   SING N N 24 
A2R N6     HN62   SING N N 25 
A2R C5     N7     SING Y N 26 
A2R N7     C8     DOUB Y N 27 
A2R C8     H8     SING N N 28 
A2R "O4'"  "C4'"  SING N N 29 
A2R "C3'"  "C4'"  SING N N 30 
A2R "C3'"  "O3'"  SING N N 31 
A2R "C3'"  "H3'"  SING N N 32 
A2R "O3'"  "HO3'" SING N N 33 
A2R "C4'"  "C5'"  SING N N 34 
A2R "C4'"  "H4'"  SING N N 35 
A2R "C5'"  "O5'"  SING N N 36 
A2R "C5'"  "H5'1" SING N N 37 
A2R "C5'"  "H5'2" SING N N 38 
A2R "O5'"  P      SING N N 39 
A2R P      O1     DOUB N N 40 
A2R P      O3     SING N N 41 
A2R P      O2     SING N N 42 
A2R O2     HO2    SING N N 43 
A2R O3     P1     SING N N 44 
A2R P1     "O15'" SING N N 45 
A2R P1     O12    DOUB N N 46 
A2R P1     O11    SING N N 47 
A2R O11    HO11   SING N N 48 
A2R "O15'" "C15'" SING N N 49 
A2R "C15'" "C14'" SING N N 50 
A2R "C15'" "H5'3" SING N N 51 
A2R "C15'" "H5'4" SING N N 52 
A2R "C14'" "C13'" SING N N 53 
A2R "C14'" "O14'" SING N N 54 
A2R "C14'" "H14'" SING N N 55 
A2R "C13'" "O13'" SING N N 56 
A2R "C13'" "C12'" SING N N 57 
A2R "C13'" "H13'" SING N N 58 
A2R "O13'" "H16'" SING N N 59 
A2R "C12'" "O12'" SING N N 60 
A2R "C12'" "C11'" SING N N 61 
A2R "C12'" "H12'" SING N N 62 
A2R "O12'" "H15'" SING N N 63 
A2R "C11'" "O14'" SING N N 64 
A2R "C11'" "O11'" SING N N 65 
A2R "C11'" "H11'" SING N N 66 
A2R "O11'" "H17'" SING N N 67 
# 
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 
A2R SMILES           ACDLabs              10.04 O=P(O)(O)OC3C(O)C(OC3n1c2ncnc(N)c2nc1)COP(=O)(O)OP(=O)(O)OCC4OC(O)C(O)C4O 
A2R InChI            InChI                1.02b 
;InChI=1/C15H24N5O17P3/c16-12-7-13(18-3-17-12)20(4-19-7)14-11(36-38(25,26)27)9(22)6(34-14)2-33-40(30,31)37-39(28,29)32-1-5-8(21)10(23)15(24)35-5/h3-6,8-11,14-15,21-24H,1-2H2,(H,28,29)(H,30,31)(H2,16,17,18)(H2,25,26,27)/t5-,6-,8-,9-,10-,11-,14-,15-/m1/s1/f/h25-26,28,30H,16H2
;
A2R InChIKey         InChI                1.02b ICNHOLCERMYLRZ-MFRATEIODC 
A2R 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](O)[C@H](O)[C@@H]4O)[C@@H](O)[C@H]3O[P](O)(O)=O 
A2R SMILES           CACTVS               3.341 Nc1ncnc2n(cnc12)[CH]3O[CH](CO[P](O)(=O)O[P](O)(=O)OC[CH]4O[CH](O)[CH](O)[CH]4O)[CH](O)[CH]3O[P](O)(O)=O 
A2R 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)O)O)O)O)OP(=O)(O)O)N 
A2R 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)O)O)O)O)OP(=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 
A2R "SYSTEMATIC NAME" ACDLabs              10.04 "[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)tetrahydrofuran-2-yl]methyl [(2R,3S,4R,5R)-3,4,5-trihydroxytetrahydrofuran-2-yl]methyl dihydrogen diphosphate (non-preferred name)" 
A2R "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxy-oxolan-2-yl]methyl [hydroxy-[[(2R,3S,4R,5R)-3,4,5-trihydroxyoxolan-2-yl]methoxy]phosphoryl] hydrogen phosphate"                          
# 
