data_APW
# 
_chem_comp.id                                    APW 
_chem_comp.name                                  "5'-O-[(S)-{[(S)-amino(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]adenosine" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C10 H16 N6 O9 P2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "MAGNESIUM-5'-ADENYLY-BETA-AMIDO-DIPHOSPHATE" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-02-19 
_chem_comp.pdbx_modified_date                    2026-05-19 
_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                        426.216 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     APW 
_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        ? 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
_chem_comp.pdbx_pcm                              ? 
# 
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.pdbx_n_terminal_atom_flag 
_chem_comp_atom.pdbx_backbone_atom_flag 
_chem_comp_atom.pdbx_c_terminal_atom_flag 
_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 
APW O2A    O2A  O 0 1 N N N N N N 28.749 31.125 19.304 4.485  1.914  0.352  O2A    APW 1  
APW PA     PA   P 0 1 N N N N N N 29.072 31.992 20.626 3.620  0.557  0.369  PA     APW 2  
APW O1A    O1A  O 0 1 N N N N N N 28.872 33.540 20.320 3.563  0.024  1.748  O1A    APW 3  
APW O3A    O3A  O 0 1 N N N N N N 30.541 31.675 21.324 4.308  -0.530 -0.599 O3A    APW 4  
APW PB     PB   P 0 1 N N N N N N 31.542 30.367 21.265 5.552  -1.539 -0.440 PB     APW 5  
APW O1B    O1B  O 0 1 N N N N N N 32.137 30.159 22.606 5.296  -2.467 0.684  O1B    APW 6  
APW O2B    O2B  O 0 1 N N N N N N 30.561 29.366 20.662 5.736  -2.382 -1.800 O2B    APW 7  
APW N3B    N3B  N 0 1 N N N N N N 32.772 30.789 20.108 6.953  -0.659 -0.132 N3B    APW 8  
APW "O5'"  O5*  O 0 1 N N N N N N 27.989 31.483 21.700 2.126  0.866  -0.148 "O5'"  APW 9  
APW "C5'"  C5*  C 0 1 N N N N N N 27.945 32.109 22.975 1.218  1.713  0.559  "C5'"  APW 10 
APW "C4'"  C4*  C 0 1 N N R N N N 26.496 32.415 23.266 -0.106 1.791  -0.205 "C4'"  APW 11 
APW "C3'"  C3*  C 0 1 N N S N N N 26.364 33.211 24.545 -1.060 2.799  0.474  "C3'"  APW 12 
APW "O3'"  O3*  O 0 1 N N N N N N 26.605 34.593 24.300 -1.016 4.060  -0.197 "O3'"  APW 13 
APW "C2'"  C2*  C 0 1 N N R N N N 24.934 32.914 24.931 -2.456 2.154  0.324  "C2'"  APW 14 
APW "O2'"  O2*  O 0 1 N N N N N N 24.034 33.738 24.188 -3.317 2.997  -0.444 "O2'"  APW 15 
APW "C1'"  C1*  C 0 1 N N R N N N 24.772 31.454 24.525 -2.180 0.833  -0.428 "C1'"  APW 16 
APW "O4'"  O4*  O 0 1 N N N N N N 25.717 31.226 23.468 -0.799 0.525  -0.140 "O4'"  APW 17 
APW N9     N9   N 0 1 Y N N N N N 25.131 30.642 25.709 -3.054 -0.231 0.072  N9     APW 18 
APW C4     C4   C 0 1 Y N N N N N 24.567 30.740 26.918 -4.337 -0.489 -0.340 C4     APW 19 
APW C5     C5   C 0 1 Y N N N N N 25.249 29.764 27.776 -4.772 -1.592 0.414  C5     APW 20 
APW N7     N7   N 0 1 Y N N N N N 26.168 29.151 27.009 -3.751 -1.944 1.232  N7     APW 21 
APW C8     C8   C 0 1 Y N N N N N 26.088 29.696 25.766 -2.740 -1.150 1.029  C8     APW 22 
APW N3     N3   N 0 1 Y N N N N N 23.579 31.490 27.452 -5.164 0.053  -1.228 N3     APW 23 
APW C2     C2   C 0 1 Y N N N N N 23.229 31.339 28.745 -6.374 -0.434 -1.403 C2     APW 24 
APW N1     N1   N 0 1 Y N N N N N 23.806 30.467 29.590 -6.827 -1.469 -0.718 N1     APW 25 
APW C6     C6   C 0 1 Y N N N N N 24.805 29.654 29.182 -6.073 -2.076 0.191  C6     APW 26 
APW N6     N6   N 0 1 N N N N N N 25.400 28.773 30.025 -6.556 -3.160 0.903  N6     APW 27 
APW H3B1   1H3B H 0 0 N N N N N N 33.421 30.033 20.020 7.150  -0.018 -0.886 H3B1   APW 28 
APW H3B2   2H3B H 0 0 N N N N N N 32.347 30.968 19.221 6.887  -0.171 0.749  H3B2   APW 29 
APW "H5'1" 1H5* H 0 0 N N N N N N 28.350 31.433 23.742 1.040  1.305  1.554  "H5'1" APW 30 
APW "H5'2" 2H5* H 0 0 N N N N N N 28.532 33.039 22.960 1.646  2.712  0.647  "H5'2" APW 31 
APW "H4'"  H4*  H 0 1 N N N N N N 26.079 33.002 22.434 0.071  2.075  -1.242 "H4'"  APW 32 
APW "H3'"  H3*  H 0 1 N N N N N N 27.050 32.815 25.308 -0.803 2.918  1.527  "H3'"  APW 33 
APW H2     H2   H 0 1 N N N N N N 26.518 35.079 25.112 -1.596 4.730  0.188  H2     APW 34 
APW H1     H1   H 0 1 N N N N N N 24.794 33.029 26.016 -2.892 1.955  1.303  H1     APW 35 
APW "H2'"  H2*  H 0 1 N N N N N N 23.140 33.540 24.441 -3.475 3.864  -0.047 "H2'"  APW 36 
APW "H1'"  H1*  H 0 1 N N N N N N 23.739 31.254 24.203 -2.323 0.969  -1.500 "H1'"  APW 37 
APW H8     H8   H 0 1 N N N N N N 26.711 29.408 24.932 -1.793 -1.209 1.545  H8     APW 38 
APW H3     H3   H 0 1 N N N N N N 22.432 31.960 29.127 -7.021 0.029  -2.133 H3     APW 39 
APW HN61   1HN6 H 0 0 N N N N N N 24.983 28.844 30.931 -5.995 -3.595 1.565  HN61   APW 40 
APW HN62   2HN6 H 0 0 N N N N N N 25.280 27.844 29.675 -7.455 -3.485 0.741  HN62   APW 41 
APW H4     H4   H 0 1 N N N N N N 28.501 31.707 18.596 4.564  2.320  -0.522 H4     APW 42 
APW H5     H5   H 0 1 N N N N N N 30.425 28.649 21.270 6.470  -3.012 -1.776 H5     APW 43 
# 
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 
APW O2A   PA     SING N N 1  
APW PA    O1A    DOUB N N 2  
APW PA    O3A    SING N N 3  
APW PA    "O5'"  SING N N 4  
APW O3A   PB     SING N N 5  
APW PB    O1B    DOUB N N 6  
APW PB    O2B    SING N N 7  
APW PB    N3B    SING N N 8  
APW N3B   H3B1   SING N N 9  
APW N3B   H3B2   SING N N 10 
APW "O5'" "C5'"  SING N N 11 
APW "C5'" "C4'"  SING N N 12 
APW "C5'" "H5'1" SING N N 13 
APW "C5'" "H5'2" SING N N 14 
APW "C4'" "C3'"  SING N N 15 
APW "C4'" "O4'"  SING N N 16 
APW "C4'" "H4'"  SING N N 17 
APW "C3'" "O3'"  SING N N 18 
APW "C3'" "C2'"  SING N N 19 
APW "C3'" "H3'"  SING N N 20 
APW "O3'" H2     SING N N 21 
APW "C2'" "O2'"  SING N N 22 
APW "C2'" "C1'"  SING N N 23 
APW "C2'" H1     SING N N 24 
APW "O2'" "H2'"  SING N N 25 
APW "C1'" "O4'"  SING N N 26 
APW "C1'" N9     SING N N 27 
APW "C1'" "H1'"  SING N N 28 
APW N9    C4     SING Y N 29 
APW N9    C8     SING Y N 30 
APW C4    C5     SING Y N 31 
APW C4    N3     DOUB Y N 32 
APW C5    N7     SING Y N 33 
APW C5    C6     DOUB Y N 34 
APW N7    C8     DOUB Y N 35 
APW C8    H8     SING N N 36 
APW N3    C2     SING Y N 37 
APW C2    N1     DOUB Y N 38 
APW C2    H3     SING N N 39 
APW N1    C6     SING Y N 40 
APW C6    N6     SING N N 41 
APW N6    HN61   SING N N 42 
APW N6    HN62   SING N N 43 
APW O2A   H4     SING N N 44 
APW O2B   H5     SING N N 45 
# 
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 
APW SMILES           ACDLabs              14.52   "NP(=O)(O)OP(=O)(O)OCC1OC(n2cnc3c(N)ncnc32)C(O)C1O"                                                                                                                                    
APW InChI            InChI                1.06    "InChI=1S/C10H16N6O9P2/c11-8-5-9(14-2-13-8)16(3-15-5)10-7(18)6(17)4(24-10)1-23-27(21,22)25-26(12,19)20/h2-4,6-7,10,17-18H,1H2,(H,21,22)(H2,11,13,14)(H3,12,19,20)/t4-,6-,7-,10-/m1/s1" 
APW InChIKey         InChI                1.06    FQMDCEJHLOLKLI-KQYNXXCUSA-N                                                                                                                                                            
APW SMILES_CANONICAL CACTVS               3.385   "Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P](O)(=O)O[P](N)(O)=O)[C@@H](O)[C@H]3O"                                                                                                              
APW SMILES           CACTVS               3.385   "Nc1ncnc2n(cnc12)[CH]3O[CH](CO[P](O)(=O)O[P](N)(O)=O)[CH](O)[CH]3O"                                                                                                                    
APW SMILES_CANONICAL "OpenEye OEToolkits" 3.1.0.0 "c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO[P@](=O)(O)O[P@](=O)(N)O)O)O)N"                                                                                                      
APW SMILES           "OpenEye OEToolkits" 3.1.0.0 "c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COP(=O)(O)OP(=O)(N)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 
APW "SYSTEMATIC NAME" ACDLabs              14.52   "5'-O-[(S)-{[(S)-amino(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]adenosine"                                                        
APW "SYSTEMATIC NAME" "OpenEye OEToolkits" 3.1.0.0 "[[(2~{R},3~{S},4~{R},5~{R})-5-(6-aminopurin-9-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methoxy-oxidanyl-phosphoryl]oxyphosphonamidic acid" 
# 
_pdbx_chem_comp_synonyms.ordinal      1 
_pdbx_chem_comp_synonyms.comp_id      APW 
_pdbx_chem_comp_synonyms.name         "MAGNESIUM-5'-ADENYLY-BETA-AMIDO-DIPHOSPHATE" 
_pdbx_chem_comp_synonyms.provenance   ? 
_pdbx_chem_comp_synonyms.type         ? 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
APW "Create component"   2006-02-19 RCSB 
APW "Modify descriptor"  2011-06-04 RCSB 
APW "Modify synonyms"    2020-06-05 PDBE 
APW "Other modification" 2026-05-19 RCSB 
# 
