data_A1AQN
# 
_chem_comp.id                                    A1AQN 
_chem_comp.name                                  "9-{3-O-[(S)-thiophosphono]-alpha-L-lyxofuranosyl}-9H-purin-6-amine" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C10 H14 N5 O6 P S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2024-04-30 
_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                        363.287 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     A1AQN 
_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        9BKQ 
_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 
A1AQN C02  C1  C 0 1 N N N N N N -11.381 14.166 22.674 2.123  -2.105 -0.726 C02  A1AQN 1  
A1AQN C03  C2  C 0 1 N N S N N N -11.391 13.002 21.767 0.853  -1.304 -0.431 C03  A1AQN 2  
A1AQN C04  C3  C 0 1 N N S N N N -10.356 12.187 21.688 1.213  0.135  -0.000 C04  A1AQN 3  
A1AQN C10  C4  C 0 1 N N R N N N -11.085 11.450 20.641 0.107  1.005  -0.638 C10  A1AQN 4  
A1AQN C12  C5  C 0 1 N N R N N N -12.512 11.167 21.248 -0.790 -0.011 -1.379 C12  A1AQN 5  
A1AQN C14  C6  C 0 1 Y N N N N N -14.176 9.951  19.964 -2.020 -1.548 0.199  C14  A1AQN 6  
A1AQN C16  C7  C 0 1 Y N N N N N -14.969 11.421 18.755 -3.863 -0.455 0.536  C16  A1AQN 7  
A1AQN C17  C8  C 0 1 Y N N N N N -15.611 12.252 17.857 -5.120 0.048  0.910  C17  A1AQN 8  
A1AQN C20  C9  C 0 1 Y N N N N N -14.411 13.992 18.613 -4.730 1.905  -0.404 C20  A1AQN 9  
A1AQN C22  C10 C 0 1 Y N N N N N -14.048 11.993 19.565 -3.074 0.313  -0.337 C22  A1AQN 10 
A1AQN N13  N1  N 0 1 Y N N N N N -13.600 11.051 20.330 -1.921 -0.404 -0.535 N13  A1AQN 11 
A1AQN N15  N2  N 0 1 Y N N N N N -15.033 10.152 19.035 -3.160 -1.577 0.826  N15  A1AQN 12 
A1AQN N18  N3  N 0 1 N N N N N N -16.580 11.707 16.974 -5.939 -0.662 1.771  N18  A1AQN 13 
A1AQN N19  N4  N 0 1 Y N N N N N -15.316 13.514 17.819 -5.505 1.221  0.418  N19  A1AQN 14 
A1AQN N21  N5  N 0 1 Y N N N N N -13.775 13.253 19.467 -3.542 1.477  -0.776 N21  A1AQN 15 
A1AQN O01  O1  O 0 1 N N N N N N -11.846 15.095 21.758 1.770  -3.444 -1.081 O01  A1AQN 16 
A1AQN O05  O2  O 0 1 N N N N N N -10.026 11.320 22.678 2.497  0.502  -0.506 O05  A1AQN 17 
A1AQN O07  O3  O 0 1 N N N N N N -7.715  10.458 21.972 3.286  2.076  1.303  O07  A1AQN 18 
A1AQN O09  O4  O 0 1 N N N N N N -8.536  9.854  23.994 4.962  1.417  -0.466 O09  A1AQN 19 
A1AQN O11  O5  O 0 1 N N N N N N -10.407 10.347 20.259 0.674  1.940  -1.558 O11  A1AQN 20 
A1AQN O23  O6  O 0 1 N N N N N N -12.774 12.237 21.863 0.068  -1.145 -1.633 O23  A1AQN 21 
A1AQN P06  P1  P 0 1 N N N N N N -8.494  10.946 23.057 3.718  0.951  0.443  P06  A1AQN 22 
A1AQN S08  S1  S 0 1 N N N N N N -7.596  12.508 24.164 4.305  -0.683 1.660  S08  A1AQN 23 
A1AQN H022 H1  H 0 0 N N N N N N -10.372 14.405 23.041 2.662  -1.640 -1.552 H022 A1AQN 24 
A1AQN H021 H2  H 0 0 N N N N N N -12.062 14.040 23.529 2.757  -2.119 0.160  H021 A1AQN 25 
A1AQN H031 H3  H 0 0 N N N N N N -11.453 13.466 20.771 0.265  -1.798 0.343  H031 A1AQN 26 
A1AQN H041 H4  H 0 0 N N N N N N -9.469  12.674 21.258 1.191  0.225  1.086  H041 A1AQN 27 
A1AQN H101 H5  H 0 0 N N N N N N -11.227 12.122 19.781 -0.462 1.526  0.132  H101 A1AQN 28 
A1AQN H121 H6  H 0 0 N N N N N N -12.452 10.283 21.900 -1.147 0.412  -2.318 H121 A1AQN 29 
A1AQN H141 H7  H 0 0 N N N N N N -13.960 8.983  20.390 -1.266 -2.320 0.249  H141 A1AQN 30 
A1AQN H201 H8  H 0 0 N N N N N N -14.178 15.045 18.561 -5.082 2.854  -0.780 H201 A1AQN 31 
A1AQN H181 H9  H 0 0 N N N N N N -16.941 12.431 16.386 -5.647 -1.517 2.124  H181 A1AQN 32 
A1AQN H182 H10 H 0 0 N N N N N N -16.155 10.999 16.409 -6.805 -0.304 2.022  H182 A1AQN 33 
A1AQN H011 H11 H 0 0 N N N N N N -11.910 15.946 22.174 2.528  -4.010 -1.282 H011 A1AQN 34 
A1AQN H1   H12 H 0 1 N N N N N N -8.045  9.119  23.646 5.298  0.728  -1.056 H1   A1AQN 35 
A1AQN H111 H13 H 0 0 N N N N N N -10.897 9.891  19.585 0.024  2.513  -1.988 H111 A1AQN 36 
A1AQN H2   H14 H 0 1 N N N N N N -6.401  12.040 24.372 5.314  -0.171 2.388  H2   A1AQN 37 
# 
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 
A1AQN C02 O01  SING N N 1  
A1AQN C03 C02  SING N N 2  
A1AQN C04 C03  SING N N 3  
A1AQN P06 O05  SING N N 4  
A1AQN O07 P06  DOUB N N 5  
A1AQN S08 P06  SING N N 6  
A1AQN O09 P06  SING N N 7  
A1AQN O05 C04  SING N N 8  
A1AQN C10 C04  SING N N 9  
A1AQN O11 C10  SING N N 10 
A1AQN C12 C10  SING N N 11 
A1AQN C14 N13  SING Y N 12 
A1AQN N15 C14  DOUB Y N 13 
A1AQN C16 N15  SING Y N 14 
A1AQN C17 C16  DOUB Y N 15 
A1AQN N18 C17  SING N N 16 
A1AQN N19 C17  SING Y N 17 
A1AQN C20 N19  DOUB Y N 18 
A1AQN N21 C20  SING Y N 19 
A1AQN C22 N21  DOUB Y N 20 
A1AQN N13 C12  SING N N 21 
A1AQN O23 C12  SING N N 22 
A1AQN C03 O23  SING N N 23 
A1AQN N13 C22  SING Y N 24 
A1AQN C16 C22  SING Y N 25 
A1AQN C02 H022 SING N N 26 
A1AQN C02 H021 SING N N 27 
A1AQN C03 H031 SING N N 28 
A1AQN C04 H041 SING N N 29 
A1AQN C10 H101 SING N N 30 
A1AQN C12 H121 SING N N 31 
A1AQN C14 H141 SING N N 32 
A1AQN C20 H201 SING N N 33 
A1AQN N18 H181 SING N N 34 
A1AQN N18 H182 SING N N 35 
A1AQN O01 H011 SING N N 36 
A1AQN O09 H1   SING N N 37 
A1AQN O11 H111 SING N N 38 
A1AQN S08 H2   SING N N 39 
# 
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 
A1AQN SMILES           ACDLabs              12.01 "O=P(O)(S)OC1C(CO)OC(n2cnc3c(N)ncnc32)C1O"                                                                                                                        
A1AQN InChI            InChI                1.06  "InChI=1S/C10H14N5O6PS/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(17)7(4(1-16)20-10)21-22(18,19)23/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,23)/t4-,6+,7+,10+/m0/s1" 
A1AQN InChIKey         InChI                1.06  GJFFFGIFPPIFQW-HGOUYRHRSA-N                                                                                                                                       
A1AQN SMILES_CANONICAL CACTVS               3.385 "Nc1ncnc2n(cnc12)[C@@H]3O[C@@H](CO)[C@@H](O[P](O)(S)=O)[C@H]3O"                                                                                                   
A1AQN SMILES           CACTVS               3.385 "Nc1ncnc2n(cnc12)[CH]3O[CH](CO)[CH](O[P](O)(S)=O)[CH]3O"                                                                                                          
A1AQN SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@@H](O3)CO)OP(=O)(O)S)O)N"                                                                                               
A1AQN SMILES           "OpenEye OEToolkits" 2.0.7 "c1nc(c2c(n1)n(cn2)C3C(C(C(O3)CO)OP(=O)(O)S)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 
A1AQN "SYSTEMATIC NAME" ACDLabs              12.01 "9-{3-O-[(S)-thiophosphono]-alpha-L-lyxofuranosyl}-9H-purin-6-amine"                                                     
A1AQN "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.7 "[(2~{S},3~{S},4~{R},5~{R})-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-oxidanyl-oxolan-3-yl]oxy-sulfanyl-phosphinic acid" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
A1AQN "Create component" 2024-04-30 RCSB 
A1AQN "Initial release"  2024-09-04 RCSB 
# 
