data_YHK
# 
_chem_comp.id                                    YHK 
_chem_comp.name                                  "5'-O-[(R)-(cyclopropyloxy)(hydroxy)phosphoryl]adenosine" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C13 H18 N5 O7 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2023-02-03 
_chem_comp.pdbx_modified_date                    2023-02-10 
_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                        387.285 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     YHK 
_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        8G0T 
_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 
YHK C1  C1  C 0 1 N N S -15.133 24.564 8.210  -0.268 2.586  0.526  C1  YHK 1  
YHK C10 C2  C 0 1 N N N -13.554 23.808 6.338  1.886  1.275  0.648  C10 YHK 2  
YHK C11 C3  C 0 1 N N N -12.966 22.299 3.413  6.206  -1.552 -0.454 C11 YHK 3  
YHK C12 C4  C 0 1 N N N -14.428 21.971 3.492  7.217  -1.168 -1.536 C12 YHK 4  
YHK C13 C5  C 0 1 N N N -13.521 21.116 2.671  6.685  -2.600 -1.460 C13 YHK 5  
YHK C2  C6  C 0 1 N N R -15.973 25.837 8.303  -1.719 2.086  0.343  C2  YHK 6  
YHK C3  C7  C 0 1 N N R -16.129 26.177 6.824  -1.563 0.748  -0.413 C3  YHK 7  
YHK C4  C8  C 0 1 Y N N -17.019 24.457 5.184  -2.356 -1.171 1.021  C4  YHK 8  
YHK C5  C9  C 0 1 Y N N -19.116 24.782 5.317  -4.404 -1.409 0.348  C5  YHK 9  
YHK C6  C10 C 0 1 Y N N -18.532 25.678 6.193  -3.845 -0.347 -0.381 C6  YHK 10 
YHK C7  C11 C 0 1 Y N N -20.488 26.494 6.793  -5.842 -0.077 -1.485 C7  YHK 11 
YHK C8  C12 C 0 1 Y N N -20.520 24.796 5.220  -5.741 -1.758 0.093  C8  YHK 12 
YHK C9  C13 C 0 1 N N R -14.141 24.965 7.108  0.593  1.490  -0.141 C9  YHK 13 
YHK N1  N1  N 0 1 Y N N -17.179 25.462 6.102  -2.552 -0.223 0.061  N1  YHK 14 
YHK N2  N2  N 0 1 Y N N -18.148 24.015 4.685  -3.444 -1.865 1.189  N2  YHK 15 
YHK N3  N3  N 0 1 Y N N -19.173 26.571 6.965  -4.594 0.285  -1.279 N3  YHK 16 
YHK N4  N4  N 0 1 Y N N -21.190 25.686 5.990  -6.411 -1.069 -0.824 N4  YHK 17 
YHK N5  N5  N 0 1 N N N -21.217 23.991 4.420  -6.346 -2.796 0.780  N5  YHK 18 
YHK O1  O1  O 0 1 N N N -14.414 24.248 9.392  -0.083 3.839  -0.135 O1  YHK 19 
YHK O2  O2  O 0 1 N N N -14.881 25.835 6.221  -0.226 0.301  -0.099 O2  YHK 20 
YHK O3  O3  O 0 1 N N N -15.290 26.867 8.986  -2.474 3.016  -0.436 O3  YHK 21 
YHK O4  O4  O 0 1 N N N -12.477 24.286 5.508  2.719  0.345  -0.047 O4  YHK 22 
YHK O5  O5  O 0 1 N N N -10.570 22.847 6.229  3.981  -0.930 1.875  O5  YHK 23 
YHK O6  O6  O 0 1 N N N -12.202 21.974 4.540  4.870  -1.063 -0.596 O6  YHK 24 
YHK O7  O7  O 0 1 N N N -10.617 23.830 3.904  5.004  1.077  0.736  O7  YHK 25 
YHK P1  P1  P 0 1 N N N -11.360 23.243 5.041  4.162  -0.117 0.497  P1  YHK 26 
YHK H1  H1  H 0 1 N N N -15.755 23.722 7.871  -0.025 2.674  1.585  H1  YHK 27 
YHK H2  H2  H 0 1 N N N -14.332 23.355 5.706  2.410  2.225  0.752  H2  YHK 28 
YHK H3  H3  H 0 1 N N N -13.169 23.055 7.042  1.648  0.882  1.636  H3  YHK 29 
YHK H4  H4  H 0 1 N N N -12.684 23.176 2.811  6.570  -1.632 0.570  H4  YHK 30 
YHK H5  H5  H 0 1 N N N -15.164 22.622 2.999  6.864  -0.543 -2.356 H5  YHK 31 
YHK H6  H6  H 0 1 N N N -14.853 21.580 4.428  8.247  -0.996 -1.224 H6  YHK 32 
YHK H7  H7  H 0 1 N N N -13.589 21.138 1.573  7.365  -3.371 -1.098 H7  YHK 33 
YHK H8  H8  H 0 1 N N N -13.278 20.096 3.003  5.981  -2.918 -2.230 H8  YHK 34 
YHK H9  H9  H 0 1 N N N -16.953 25.619 8.753  -2.193 1.927  1.312  H9  YHK 35 
YHK H10 H10 H 0 1 N N N -16.300 27.260 6.733  -1.669 0.904  -1.486 H10 YHK 36 
YHK H11 H11 H 0 1 N N N -16.054 24.066 4.898  -1.434 -1.325 1.561  H11 YHK 37 
YHK H12 H12 H 0 1 N N N -21.074 27.181 7.385  -6.424 0.458  -2.222 H12 YHK 38 
YHK H13 H13 H 0 1 N N N -13.319 25.530 7.573  0.819  1.761  -1.173 H13 YHK 39 
YHK H14 H14 H 0 1 N N N -22.193 24.184 4.521  -5.846 -3.293 1.447  H14 YHK 40 
YHK H15 H15 H 0 1 N N N -20.943 24.146 3.471  -7.269 -3.027 0.595  H15 YHK 41 
YHK H16 H16 H 0 1 N N N -15.023 23.999 10.077 -0.645 4.549  0.205  H16 YHK 42 
YHK H17 H17 H 0 1 N N N -15.204 26.636 9.903  -2.552 3.893  -0.035 H17 YHK 43 
YHK H18 H18 H 0 1 N N N -9.652  23.039 6.078  3.439  -1.727 1.793  H18 YHK 44 
# 
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 
YHK C13 C11 SING N N 1  
YHK C13 C12 SING N N 2  
YHK C11 C12 SING N N 3  
YHK C11 O6  SING N N 4  
YHK O7  P1  DOUB N N 5  
YHK N5  C8  SING N N 6  
YHK O6  P1  SING N N 7  
YHK N2  C4  DOUB Y N 8  
YHK N2  C5  SING Y N 9  
YHK P1  O4  SING N N 10 
YHK P1  O5  SING N N 11 
YHK C4  N1  SING Y N 12 
YHK C8  C5  SING Y N 13 
YHK C8  N4  DOUB Y N 14 
YHK C5  C6  DOUB Y N 15 
YHK O4  C10 SING N N 16 
YHK N4  C7  SING Y N 17 
YHK N1  C6  SING Y N 18 
YHK N1  C3  SING N N 19 
YHK C6  N3  SING Y N 20 
YHK O2  C3  SING N N 21 
YHK O2  C9  SING N N 22 
YHK C10 C9  SING N N 23 
YHK C7  N3  DOUB Y N 24 
YHK C3  C2  SING N N 25 
YHK C9  C1  SING N N 26 
YHK C1  C2  SING N N 27 
YHK C1  O1  SING N N 28 
YHK C2  O3  SING N N 29 
YHK C1  H1  SING N N 30 
YHK C10 H2  SING N N 31 
YHK C10 H3  SING N N 32 
YHK C11 H4  SING N N 33 
YHK C12 H5  SING N N 34 
YHK C12 H6  SING N N 35 
YHK C13 H7  SING N N 36 
YHK C13 H8  SING N N 37 
YHK C2  H9  SING N N 38 
YHK C3  H10 SING N N 39 
YHK C4  H11 SING N N 40 
YHK C7  H12 SING N N 41 
YHK C9  H13 SING N N 42 
YHK N5  H14 SING N N 43 
YHK N5  H15 SING N N 44 
YHK O1  H16 SING N N 45 
YHK O3  H17 SING N N 46 
YHK O5  H18 SING N N 47 
# 
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 
YHK SMILES           ACDLabs              12.01 "O=P(O)(OC1CC1)OCC1OC(n2cnc3c(N)ncnc32)C(O)C1O"                                                                                                                              
YHK InChI            InChI                1.06  "InChI=1S/C13H18N5O7P/c14-11-8-12(16-4-15-11)18(5-17-8)13-10(20)9(19)7(24-13)3-23-26(21,22)25-6-1-2-6/h4-7,9-10,13,19-20H,1-3H2,(H,21,22)(H2,14,15,16)/t7-,9-,10-,13-/m1/s1" 
YHK InChIKey         InChI                1.06  FJCZQSQASCNEEZ-QYVSTXNMSA-N                                                                                                                                                  
YHK SMILES_CANONICAL CACTVS               3.385 "Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P](O)(=O)OC4CC4)[C@@H](O)[C@H]3O"                                                                                                          
YHK SMILES           CACTVS               3.385 "Nc1ncnc2n(cnc12)[CH]3O[CH](CO[P](O)(=O)OC4CC4)[CH](O)[CH]3O"                                                                                                                
YHK 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)OC4CC4)O)O)N"                                                                                                      
YHK SMILES           "OpenEye OEToolkits" 2.0.7 "c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COP(=O)(O)OC4CC4)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 
YHK "SYSTEMATIC NAME" ACDLabs              12.01 "5'-O-[(R)-(cyclopropyloxy)(hydroxy)phosphoryl]adenosine"                                                             
YHK "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.7 "[(2~{R},3~{S},4~{R},5~{R})-5-(6-aminopurin-9-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methyl cyclopropyl 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 
YHK "Create component" 2023-02-03 RCSB 
YHK "Initial release"  2023-02-15 RCSB 
# 
