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 2011-06-04 _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 N N 7 00A CC C1C SING N N 8 00A C6C C1C DOUB Y N 9 00A C1C C2C SING Y 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 N N 16 00A C6C C5C SING Y 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 Y N 43 00A C8 N7 DOUB Y N 44 00A C8 H8 SING N N 45 00A N1 C6 SING Y N 46 00A C6 N6 SING N N 47 00A N6 HN6 SING N N 48 00A N6 HN6A SING N N 49 00A C2 N1 DOUB Y N 50 00A C2 N3 SING Y N 51 00A C2 H2 SING N 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 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" 00A InChI InChI 1.03 "InChI=1S/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" 00A InChIKey InChI 1.03 RVDNKWBGRIIRML-XNIJJKJLSA-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 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" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 00A "Create component" 2008-04-28 RCSB 00A "Modify aromatic_flag" 2011-06-04 RCSB 00A "Modify descriptor" 2011-06-04 RCSB #