data_A1AWU
# 
_chem_comp.id                                    A1AWU 
_chem_comp.name                                  "[(2~{R},3~{R},4~{R},5~{S})-5-(6-aminopurin-9-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methyl [(2~{R},3~{R},4~{S},5~{R})-2-(2-azanyl-6-oxidanylidene-1~{H}-purin-9-yl)-5-(hydroxymethyl)-4-oxidanyl-oxolan-3-yl] hydrogen phosphate" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H25 N10 O11 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2024-07-08 
_chem_comp.pdbx_modified_date                    2024-08-30 
_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                        612.447 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     A1AWU 
_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        9CIW 
_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.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 
A1AWU C02  C1  C 0 1 N N N N N N 34.262 18.567 -25.444 -5.762 -3.000 1.441  C02  A1AWU 1  
A1AWU C04  C2  C 0 1 N N N N N N 34.969 19.678 -23.326 -3.408 -3.030 1.490  C04  A1AWU 2  
A1AWU C07  C3  C 0 1 Y N N N N N 33.306 20.854 -24.899 -4.442 -1.002 1.093  C07  A1AWU 3  
A1AWU C08  C4  C 0 1 Y N N N N N 33.372 19.771 -25.771 -5.699 -1.610 1.185  C08  A1AWU 4  
A1AWU C10  C5  C 0 1 Y N N N N N 32.016 21.242 -26.592 -6.031 0.495  0.789  C10  A1AWU 5  
A1AWU C12  C6  C 0 1 N N R N N N 32.054 23.049 -24.896 -3.664 1.363  0.657  C12  A1AWU 6  
A1AWU C14  C7  C 0 1 N N R N N N 31.684 23.687 -23.505 -3.196 1.387  -0.811 C14  A1AWU 7  
A1AWU C18  C8  C 0 1 N N N N N N 29.668 26.819 -25.767 1.231  -1.240 -1.979 C18  A1AWU 8  
A1AWU C19  C9  C 0 1 N N R N N N 28.477 27.389 -26.581 2.687  -0.988 -1.583 C19  A1AWU 9  
A1AWU C20  C10 C 0 1 N N R N N N 28.215 26.649 -27.652 3.603  -2.114 -2.128 C20  A1AWU 10 
A1AWU C22  C11 C 0 1 N N R N N N 29.485 26.949 -28.565 4.802  -2.058 -1.151 C22  A1AWU 11 
A1AWU C24  C12 C 0 1 N N S N N N 29.485 28.283 -28.618 4.241  -1.348 0.096  C24  A1AWU 12 
A1AWU C26  C13 C 0 1 Y N N N N N 27.382 29.673 -28.552 4.567  1.145  -0.109 C26  A1AWU 13 
A1AWU C28  C14 C 0 1 Y N N N N N 27.717 31.015 -30.214 6.441  1.435  0.943  C28  A1AWU 14 
A1AWU C29  C15 C 0 1 Y N N N N N 27.728 31.983 -31.244 7.621  1.879  1.563  C29  A1AWU 15 
A1AWU C32  C16 C 0 1 Y N N N N N 29.795 31.218 -31.928 8.075  -0.298 2.180  C32  A1AWU 16 
A1AWU C34  C17 C 0 1 Y N N N N N 28.806 30.170 -30.104 6.140  0.064  0.994  C34  A1AWU 17 
A1AWU C38  C18 C 0 1 N N S N N N 32.678 24.456 -23.185 -3.510 2.827  -1.286 C38  A1AWU 18 
A1AWU C40  C19 C 0 1 N N R N N N 33.797 24.368 -24.384 -3.601 3.599  0.055  C40  A1AWU 19 
A1AWU C41  C20 C 0 1 N N N N N N 35.214 24.354 -23.759 -4.464 4.852  -0.102 C41  A1AWU 20 
A1AWU N03  N1  N 0 1 N N N N N N 35.038 18.551 -24.235 -4.603 -3.678 1.591  N03  A1AWU 21 
A1AWU N05  N2  N 0 1 N N N N N N 35.757 19.663 -22.092 -2.247 -3.744 1.646  N05  A1AWU 22 
A1AWU N06  N3  N 0 1 N N N N N N 34.111 20.834 -23.642 -3.336 -1.740 1.247  N06  A1AWU 23 
A1AWU N09  N4  N 0 1 Y N N N N N 32.561 20.053 -26.799 -6.629 -0.643 0.991  N09  A1AWU 24 
A1AWU N11  N5  N 0 1 Y N N N N N 32.460 21.745 -25.446 -4.678 0.322  0.839  N11  A1AWU 25 
A1AWU N25  N6  N 0 1 Y N N N N N 28.573 29.356 -29.055 4.956  -0.089 0.318  N25  A1AWU 26 
A1AWU N27  N7  N 0 1 Y N N N N N 26.854 30.681 -29.234 5.439  2.039  0.259  N27  A1AWU 27 
A1AWU N30  N8  N 0 1 N N N N N N 26.599 32.906 -31.402 7.967  3.219  1.551  N30  A1AWU 28 
A1AWU N31  N9  N 0 1 Y N N N N N 28.771 32.052 -32.069 8.397  0.982  2.163  N31  A1AWU 29 
A1AWU N33  N10 N 0 1 Y N N N N N 29.826 30.295 -30.973 6.977  -0.758 1.618  N33  A1AWU 30 
A1AWU O01  O1  O 0 1 N N N N N N 34.311 17.648 -26.197 -6.836 -3.571 1.530  O01  A1AWU 31 
A1AWU O13  O2  O 0 1 N N N N N N 33.572 23.251 -25.040 -4.229 2.652  0.949  O13  A1AWU 32 
A1AWU O15  O3  O 0 1 N N N N N N 30.497 24.449 -23.558 -1.794 1.125  -0.894 O15  A1AWU 33 
A1AWU O17  O4  O 0 1 N N N N N N 29.824 25.435 -26.004 0.411  -0.184 -1.475 O17  A1AWU 34 
A1AWU O21  O5  O 0 1 N N N N N N 28.079 25.272 -27.362 2.948  -3.382 -2.060 O21  A1AWU 35 
A1AWU O23  O6  O 0 1 N N N N N N 29.291 26.387 -29.838 5.875  -1.303 -1.718 O23  A1AWU 36 
A1AWU O35  O7  O 0 1 N N N N N N 28.896 28.723 -27.253 2.849  -1.086 -0.152 O35  A1AWU 37 
A1AWU O36  O8  O 0 1 N N N N N N 29.409 22.955 -25.417 -1.798 -1.378 -1.218 O36  A1AWU 38 
A1AWU O37  O9  O 0 1 N N N N N N 28.035 24.676 -24.326 -1.491 0.053  -3.275 O37  A1AWU 39 
A1AWU O39  O10 O 0 1 N N N N N N 33.248 24.046 -21.961 -4.754 2.873  -1.987 O39  A1AWU 40 
A1AWU O42  O11 O 0 1 N N N N N N 35.991 25.339 -24.403 -4.437 5.604  1.112  O42  A1AWU 41 
A1AWU P16  P1  P 0 1 N N N N N N 29.429 24.350 -24.829 -1.181 -0.123 -1.705 P16  A1AWU 42 
A1AWU H101 H1  H 0 0 N N N N N N 31.316 21.729 -27.255 -6.530 1.435  0.607  H101 A1AWU 43 
A1AWU H121 H2  H 0 0 N N N N N N 31.551 23.632 -25.681 -2.815 1.173  1.313  H121 A1AWU 44 
A1AWU H141 H3  H 0 0 N N N N N N 31.563 22.864 -22.785 -3.754 0.661  -1.402 H141 A1AWU 45 
A1AWU H182 H4  H 0 0 N N N N N N 29.483 26.982 -24.695 1.151  -1.276 -3.065 H182 A1AWU 46 
A1AWU H181 H5  H 0 0 N N N N N N 30.590 27.341 -26.063 0.899  -2.189 -1.559 H181 A1AWU 47 
A1AWU H191 H6  H 0 0 N N N N N N 27.608 27.548 -25.926 3.018  -0.014 -1.941 H191 A1AWU 48 
A1AWU H201 H7  H 0 0 N N N N N N 27.324 27.013 -28.185 3.922  -1.896 -3.148 H201 A1AWU 49 
A1AWU H221 H8  H 0 0 N N N N N N 30.382 26.542 -28.075 5.137  -3.064 -0.899 H221 A1AWU 50 
A1AWU H241 H9  H 0 0 N N N N N N 30.516 28.663 -28.669 4.347  -1.993 0.969  H241 A1AWU 51 
A1AWU H261 H10 H 0 0 N N N N N N 26.914 29.182 -27.712 3.670  1.352  -0.673 H261 A1AWU 52 
A1AWU H321 H11 H 0 0 N N N N N N 30.628 31.292 -32.611 8.735  -0.993 2.678  H321 A1AWU 53 
A1AWU H381 H12 H 0 0 N N N N N N 32.368 25.509 -23.115 -2.702 3.217  -1.905 H381 A1AWU 54 
A1AWU H401 H13 H 0 0 N N N N N N 33.690 25.262 -25.016 -2.606 3.862  0.415  H401 A1AWU 55 
A1AWU H412 H14 H 0 0 N N N N N N 35.149 24.576 -22.684 -4.074 5.462  -0.916 H412 A1AWU 56 
A1AWU H411 H15 H 0 0 N N N N N N 35.674 23.365 -23.902 -5.490 4.561  -0.326 H411 A1AWU 57 
A1AWU H031 H16 H 0 0 N N N N N N 35.622 17.768 -24.022 -4.621 -4.631 1.771  H031 A1AWU 58 
A1AWU H052 H17 H 0 0 N N N N N N 35.714 20.438 -21.462 -2.284 -4.696 1.825  H052 A1AWU 59 
A1AWU H051 H18 H 0 0 N N N N N N 36.338 18.878 -21.880 -1.389 -3.296 1.577  H051 A1AWU 60 
A1AWU H301 H19 H 0 0 N N N N N N 26.774 33.518 -32.173 7.392  3.864  1.110  H301 A1AWU 61 
A1AWU H302 H20 H 0 0 N N N N N N 25.763 32.384 -31.574 8.784  3.513  1.983  H302 A1AWU 62 
A1AWU H211 H21 H 0 0 N N N N N N 27.893 24.796 -28.163 3.481  -4.118 -2.391 H211 A1AWU 63 
A1AWU H231 H22 H 0 0 N N N N N N 30.049 26.566 -30.382 6.228  -1.676 -2.538 H231 A1AWU 64 
A1AWU H1   H23 H 0 1 N N N N N N 27.459 23.939 -24.489 -1.116 0.856  -3.662 H1   A1AWU 65 
A1AWU H391 H24 H 0 0 N N N N N N 33.973 24.619 -21.741 -4.995 3.754  -2.305 H391 A1AWU 66 
A1AWU H421 H25 H 0 0 N N N N N N 36.866 25.345 -24.032 -4.964 6.415  1.085  H421 A1AWU 67 
# 
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 
A1AWU C02 O01  DOUB N N 1  
A1AWU N03 C02  SING N N 2  
A1AWU C04 N03  SING N N 3  
A1AWU N05 C04  SING N N 4  
A1AWU N06 C04  DOUB N N 5  
A1AWU C07 N06  SING N N 6  
A1AWU C08 C07  DOUB Y N 7  
A1AWU N09 C08  SING Y N 8  
A1AWU C10 N09  DOUB Y N 9  
A1AWU N11 C10  SING Y N 10 
A1AWU C12 N11  SING N N 11 
A1AWU O13 C12  SING N N 12 
A1AWU C14 C12  SING N N 13 
A1AWU P16 O15  SING N N 14 
A1AWU C18 O17  SING N N 15 
A1AWU C19 C18  SING N N 16 
A1AWU C20 C19  SING N N 17 
A1AWU O21 C20  SING N N 18 
A1AWU C22 C20  SING N N 19 
A1AWU O23 C22  SING N N 20 
A1AWU C24 C22  SING N N 21 
A1AWU C26 N25  SING Y N 22 
A1AWU N27 C26  DOUB Y N 23 
A1AWU C28 N27  SING Y N 24 
A1AWU C29 C28  DOUB Y N 25 
A1AWU N30 C29  SING N N 26 
A1AWU N31 C29  SING Y N 27 
A1AWU C32 N31  DOUB Y N 28 
A1AWU N33 C32  SING Y N 29 
A1AWU C34 N33  DOUB Y N 30 
A1AWU N25 C24  SING N N 31 
A1AWU O35 C24  SING N N 32 
A1AWU O17 P16  SING N N 33 
A1AWU O36 P16  DOUB N N 34 
A1AWU O37 P16  SING N N 35 
A1AWU O15 C14  SING N N 36 
A1AWU C38 C14  SING N N 37 
A1AWU O39 C38  SING N N 38 
A1AWU C40 C38  SING N N 39 
A1AWU C41 C40  SING N N 40 
A1AWU O42 C41  SING N N 41 
A1AWU C02 C08  SING N N 42 
A1AWU C07 N11  SING Y N 43 
A1AWU O13 C40  SING N N 44 
A1AWU C19 O35  SING N N 45 
A1AWU N25 C34  SING Y N 46 
A1AWU C28 C34  SING Y N 47 
A1AWU C10 H101 SING N N 48 
A1AWU C12 H121 SING N N 49 
A1AWU C14 H141 SING N N 50 
A1AWU C18 H182 SING N N 51 
A1AWU C18 H181 SING N N 52 
A1AWU C19 H191 SING N N 53 
A1AWU C20 H201 SING N N 54 
A1AWU C22 H221 SING N N 55 
A1AWU C24 H241 SING N N 56 
A1AWU C26 H261 SING N N 57 
A1AWU C32 H321 SING N N 58 
A1AWU C38 H381 SING N N 59 
A1AWU C40 H401 SING N N 60 
A1AWU C41 H412 SING N N 61 
A1AWU C41 H411 SING N N 62 
A1AWU N03 H031 SING N N 63 
A1AWU N05 H052 SING N N 64 
A1AWU N05 H051 SING N N 65 
A1AWU N30 H301 SING N N 66 
A1AWU N30 H302 SING N N 67 
A1AWU O21 H211 SING N N 68 
A1AWU O23 H231 SING N N 69 
A1AWU O37 H1   SING N N 70 
A1AWU O39 H391 SING N N 71 
A1AWU O42 H421 SING N N 72 
# 
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 
A1AWU SMILES           ACDLabs              12.01 "NC1=Nc2c(ncn2C2OC(CO)C(O)C2OP(=O)(O)OCC2OC(n3cnc4c(N)ncnc43)C(O)C2O)C(=O)N1"                                                                                                                                                       
A1AWU InChI            InChI                1.06  "InChI=1S/C20H25N10O11P/c21-14-8-15(24-3-23-14)29(4-25-8)18-12(34)10(32)7(40-18)2-38-42(36,37)41-13-11(33)6(1-31)39-19(13)30-5-26-9-16(30)27-20(22)28-17(9)35/h3-7,10-13,18-19,31-34H,1-2H2,(H,36,37)(H2,21,23,24)(H3,22,27,28,35)" 
A1AWU InChIKey         InChI                1.06  ZLNKIMYMVZHDPX-UHFFFAOYSA-N                                                                                                                                                                                                         
A1AWU SMILES_CANONICAL CACTVS               3.385 "NC1=Nc2n(cnc2C(=O)N1)[C@@H]3O[C@H](CO)[C@H](O)[C@H]3O[P](O)(=O)OC[C@H]4O[C@@H]([C@H](O)[C@H]4O)n5cnc6c(N)ncnc56"                                                                                                                   
A1AWU SMILES           CACTVS               3.385 "NC1=Nc2n(cnc2C(=O)N1)[CH]3O[CH](CO)[CH](O)[CH]3O[P](O)(=O)OC[CH]4O[CH]([CH](O)[CH]4O)n5cnc6c(N)ncnc56"                                                                                                                             
A1AWU SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "c1nc(c2c(n1)n(cn2)[C@@H]3[C@@H]([C@H]([C@H](O3)COP(=O)(O)O[C@@H]4[C@H]([C@H](O[C@H]4n5cnc6c5N=C(NC6=O)N)CO)O)O)O)N"                                                                                                                
A1AWU SMILES           "OpenEye OEToolkits" 2.0.7 "c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COP(=O)(O)OC4C(C(OC4n5cnc6c5N=C(NC6=O)N)CO)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 
A1AWU "SYSTEMATIC NAME" ACDLabs              12.01 "(2S,3R,4R,5S)-2-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl [(2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen (S)-phosphate (non-preferred name)"      
A1AWU "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.7 "[(2~{R},3~{R},4~{R},5~{S})-5-(6-aminopurin-9-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methyl [(2~{R},3~{R},4~{S},5~{R})-2-(2-azanyl-6-oxidanylidene-1~{H}-purin-9-yl)-5-(hydroxymethyl)-4-oxidanyl-oxolan-3-yl] hydrogen phosphate" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
A1AWU "Create component" 2024-07-08 RCSB 
A1AWU "Initial release"  2024-09-04 RCSB 
# 
