data_00A
# 
_chem_comp.id                                    00A 
_chem_comp.name                                  "5'-O-[(S)-{[(4-chlorophenyl)carbonyl]oxy}(hydroxy)phosphoryl]adenosine" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C17 H17 Cl N5 O8 P" 
_chem_comp.mon_nstd_parent_comp_id               A 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-04-28 
_chem_comp.pdbx_modified_date                    2008-10-14 
_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                        485.772 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     00A 
_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        3CW8 
_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 
00A O2P    O2P    O  0 1 N N N 3.620  49.698 -10.040 -2.658 -3.412 0.132  O2P    00A 1  
00A P      P      P  0 1 N N S 4.490  48.479 -10.369 -2.103 -1.962 0.559  P      00A 2  
00A O1P    O1P    O  0 1 N N N 3.724  47.150 -10.289 -1.970 -1.899 2.032  O1P    00A 3  
00A O3P    O3P    O  0 1 N N N 5.925  48.487 -9.488  -3.132 -0.827 0.064  O3P    00A 4  
00A CC     CC     C  0 1 N N N 7.270  49.153 -9.678  -4.358 -0.827 0.622  CC     00A 5  
00A C1C    C1C    C  0 1 Y N N 8.546  48.530 -9.143  -5.354 0.185  0.217  C1C    00A 6  
00A C2C    C2C    C  0 1 Y N N 8.536  47.303 -8.447  -6.626 0.188  0.794  C2C    00A 7  
00A C3C    C3C    C  0 1 Y N N 9.727  46.714 -7.946  -7.551 1.136  0.412  C3C    00A 8  
00A C4C    C4C    C  0 1 Y N N 10.960 47.357 -8.140  -7.222 2.084  -0.543 C4C    00A 9  
00A CL4A   CL4A   CL 0 0 N N N 12.530 46.624 -7.506  -8.392 3.274  -1.020 CL4A   00A 10 
00A C5C    C5C    C  0 1 Y N N 10.954 48.605 -8.833  -5.962 2.086  -1.119 C5C    00A 11 
00A C6C    C6C    C  0 1 Y N N 9.774  49.196 -9.336  -5.026 1.148  -0.740 C6C    00A 12 
00A O2     O2     O  0 1 N N N 7.425  50.244 -10.263 -4.644 -1.660 1.459  O2     00A 13 
00A "O5'"  "O5'"  O  0 1 N N N 5.095  48.606 -11.873 -0.665 -1.716 -0.121 "O5'"  00A 14 
00A "C5'"  "C5'"  C  0 1 N N N 5.594  49.848 -12.361 0.490  -2.495 0.199  "C5'"  00A 15 
00A "C4'"  "C4'"  C  0 1 N N R 6.274  49.542 -13.680 1.682  -2.000 -0.623 "C4'"  00A 16 
00A "C3'"  "C3'"  C  0 1 N N S 7.041  48.236 -13.774 2.922  -2.882 -0.358 "C3'"  00A 17 
00A "O3'"  "O3'"  O  0 1 N N N 6.233  47.080 -14.064 3.073  -3.857 -1.393 "O3'"  00A 18 
00A "C2'"  "C2'"  C  0 1 N N R 8.052  48.505 -14.859 4.102  -1.886 -0.373 "C2'"  00A 19 
00A "O2'"  "O2'"  O  0 1 N N N 7.500  47.954 -16.059 5.022  -2.214 -1.416 "O2'"  00A 20 
00A "C1'"  "C1'"  C  0 1 N N R 8.230  50.031 -14.883 3.436  -0.519 -0.645 "C1'"  00A 21 
00A "O4'"  "O4'"  O  0 1 N N N 7.190  50.560 -14.081 2.071  -0.676 -0.197 "O4'"  00A 22 
00A N9     N9     N  0 1 Y N N 9.469  50.473 -14.172 4.106  0.536  0.120  N9     00A 23 
00A C4     C4     C  0 1 Y N N 10.344 51.349 -14.682 5.227  1.229  -0.263 C4     00A 24 
00A C5     C5     C  0 1 Y N N 11.400 51.512 -13.641 5.500  2.131  0.780  C5     00A 25 
00A N7     N7     N  0 1 Y N N 11.062 50.733 -12.574 4.549  1.944  1.727  N7     00A 26 
00A C8     C8     C  0 1 Y N N 9.915  50.131 -12.912 3.727  1.013  1.339  C8     00A 27 
00A C6     C6     C  0 1 Y N N 12.483 52.431 -14.013 6.612  2.979  0.650  C6     00A 28 
00A N6     N6     N  0 1 N N N 13.502 52.690 -13.200 6.931  3.887  1.644  N6     00A 29 
00A N1     N1     N  0 1 Y N N 12.441 53.039 -15.219 7.352  2.889  -0.451 N1     00A 30 
00A C2     C2     C  0 1 Y N N 11.439 52.838 -16.126 7.055  2.026  -1.405 C2     00A 31 
00A N3     N3     N  0 1 Y N N 10.415 52.020 -15.872 6.024  1.211  -1.326 N3     00A 32 
00A HO2P   HO2P   H  0 0 N N N 3.440  49.717 -9.107  -2.770 -3.525 -0.822 HO2P   00A 33 
00A H2C    H2C    H  0 1 N N N 7.595  46.797 -8.291  -6.884 -0.551 1.538  H2C    00A 34 
00A H3C    H3C    H  0 1 N N N 9.684  45.773 -7.417  -8.535 1.139  0.857  H3C    00A 35 
00A H5C    H5C    H  0 1 N N N 11.892 49.119 -8.979  -5.711 2.828  -1.863 H5C    00A 36 
00A H6C    H6C    H  0 1 N N N 9.811  50.140 -9.859  -4.042 1.154  -1.187 H6C    00A 37 
00A "H5'"  "H5'"  H  0 1 N N N 4.772  50.564 -12.507 0.714  -2.394 1.260  "H5'"  00A 38 
00A "H5'A" "H5'A" H  0 0 N N N 6.295  50.305 -11.647 0.298  -3.542 -0.034 "H5'A" 00A 39 
00A "H4'"  "H4'"  H  0 1 N N N 5.398  49.473 -14.342 1.436  -2.000 -1.685 "H4'"  00A 40 
00A "H3'"  "H3'"  H  0 1 N N N 7.487  47.969 -12.805 2.844  -3.368 0.614  "H3'"  00A 41 
00A "HO3'" "HO3'" H  0 0 N N N 6.055  47.043 -14.996 3.836  -4.439 -1.276 "HO3'" 00A 42 
00A "H2'"  "H2'"  H  0 1 N N N 9.044  48.052 -14.717 4.608  -1.879 0.593  "H2'"  00A 43 
00A "HO2'" "HO2'" H  0 0 N N N 6.564  47.832 -15.951 5.424  -3.089 -1.325 "HO2'" 00A 44 
00A "H1'"  "H1'"  H  0 1 N N N 8.252  50.353 -15.935 3.463  -0.289 -1.710 "H1'"  00A 45 
00A H8     H8     H  0 1 N N N 9.391  49.446 -12.263 2.873  0.667  1.902  H8     00A 46 
00A HN6    HN6    H  0 1 N N N 14.346 52.755 -13.733 6.384  3.943  2.443  HN6    00A 47 
00A HN6A   HN6A   H  0 0 N N N 13.339 53.556 -12.727 7.701  4.467  1.543  HN6A   00A 48 
00A H2     H2     H  0 1 N N N 11.476 53.355 -17.074 7.683  1.985  -2.283 H2     00A 49 
# 
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 
00A P     O2P    SING N N 1  
00A O2P   HO2P   SING N N 2  
00A "O5'" P      SING N N 3  
00A P     O1P    DOUB N N 4  
00A P     O3P    SING N N 5  
00A CC    O3P    SING N N 6  
00A O2    CC     DOUB Y N 7  
00A CC    C1C    SING Y N 8  
00A C6C   C1C    DOUB N N 9  
00A C1C   C2C    SING N N 10 
00A C2C   C3C    DOUB Y N 11 
00A C2C   H2C    SING N N 12 
00A C4C   C3C    SING Y N 13 
00A C3C   H3C    SING N N 14 
00A C5C   C4C    DOUB Y N 15 
00A C4C   CL4A   SING Y N 16 
00A C6C   C5C    SING N N 17 
00A C5C   H5C    SING N N 18 
00A C6C   H6C    SING N N 19 
00A "C5'" "O5'"  SING N N 20 
00A "C4'" "C5'"  SING N N 21 
00A "C5'" "H5'"  SING N N 22 
00A "C5'" "H5'A" SING N N 23 
00A "O4'" "C4'"  SING N N 24 
00A "C3'" "C4'"  SING N N 25 
00A "C4'" "H4'"  SING N N 26 
00A "C2'" "C3'"  SING N N 27 
00A "O3'" "C3'"  SING N N 28 
00A "C3'" "H3'"  SING N N 29 
00A "O3'" "HO3'" SING N N 30 
00A "O2'" "C2'"  SING N N 31 
00A "C1'" "C2'"  SING N N 32 
00A "C2'" "H2'"  SING N N 33 
00A "O2'" "HO2'" SING N N 34 
00A "C1'" N9     SING N N 35 
00A "C1'" "O4'"  SING N N 36 
00A "C1'" "H1'"  SING N N 37 
00A C4    N9     SING Y N 38 
00A N9    C8     SING Y N 39 
00A N3    C4     DOUB Y N 40 
00A C4    C5     SING Y N 41 
00A C6    C5     DOUB Y N 42 
00A C5    N7     SING N N 43 
00A C8    N7     DOUB Y N 44 
00A C8    H8     SING N N 45 
00A N1    C6     SING N N 46 
00A C6    N6     SING N N 47 
00A N6    HN6    SING Y N 48 
00A N6    HN6A   SING Y N 49 
00A C2    N1     DOUB Y N 50 
00A C2    N3     SING N N 51 
00A C2    H2     SING Y N 52 
# 
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 
00A SMILES           ACDLabs              10.04 Clc1ccc(cc1)C(=O)OP(=O)(O)OCC4OC(n3cnc2c(ncnc23)N)C(O)C4O 
00A InChI            InChI                1.02b 
InChI=1/C17H17ClN5O8P/c18-9-3-1-8(2-4-9)17(26)31-32(27,28)29-5-10-12(24)13(25)16(30-10)23-7-22-11-14(19)20-6-21-15(11)23/h1-4,6-7,10,12-13,16,24-25H,5H2,(H,27,28)(H2,19,20,21)/t10-,12-,13-,16-/m1/s1/f/h27H,19H2 
00A InChIKey         InChI                1.02b RVDNKWBGRIIRML-LOPYZYCXDA 
00A SMILES_CANONICAL CACTVS               3.341 Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P@@](O)(=O)OC(=O)c4ccc(Cl)cc4)[C@@H](O)[C@H]3O 
00A SMILES           CACTVS               3.341 Nc1ncnc2n(cnc12)[CH]3O[CH](CO[P](O)(=O)OC(=O)c4ccc(Cl)cc4)[CH](O)[CH]3O 
00A SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(ccc1C(=O)O[P@@](=O)(O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)n3cnc4c3ncnc4N)O)O)Cl 
00A SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(ccc1C(=O)OP(=O)(O)OCC2C(C(C(O2)n3cnc4c3ncnc4N)O)O)Cl 
# 
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 
00A "SYSTEMATIC NAME" ACDLabs              10.04 "5'-O-[(S)-{[(4-chlorophenyl)carbonyl]oxy}(hydroxy)phosphoryl]adenosine"                                       
00A "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl] 4-chlorobenzoate" 
# 
