data_AP2 # _chem_comp.id AP2 _chem_comp.name "PHOSPHOMETHYLPHOSPHONIC ACID ADENOSYL ESTER" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C11 H17 N5 O9 P2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 1999-07-08 _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 425.228 _chem_comp.one_letter_code ? _chem_comp.three_letter_code AP2 _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details ? _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 1AV5 _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 AP2 PB PB P 0 1 N N N 43.174 31.463 48.444 1.220 -0.230 -5.985 PB AP2 1 AP2 O1B O1B O 0 1 N N N 43.269 30.257 47.550 1.784 1.129 -5.829 O1B AP2 2 AP2 O2B O2B O 0 1 N N N 43.689 32.654 47.774 2.251 -1.145 -6.817 O2B AP2 3 AP2 O3B O3B O 0 1 N N N 43.745 31.352 49.835 -0.179 -0.143 -6.776 O3B AP2 4 AP2 C3A C3A C 0 1 N N N 41.443 31.652 48.624 0.945 -0.966 -4.340 C3A AP2 5 AP2 PA PA P 0 1 N N R 40.545 32.747 49.426 -0.221 0.070 -3.398 PA AP2 6 AP2 O1A O1A O 0 1 N N N 40.998 34.147 49.336 0.342 1.430 -3.242 O1A AP2 7 AP2 O2A O2A O 0 1 N N N 39.133 32.830 48.987 -1.621 0.157 -4.189 O2A AP2 8 AP2 "O5'" O5* O 0 1 N N N 40.596 32.350 50.978 -0.464 -0.579 -1.946 "O5'" AP2 9 AP2 "C5'" C5* C 0 1 N N N 41.919 32.205 51.571 -1.382 0.274 -1.260 "C5'" AP2 10 AP2 "C4'" C4* C 0 1 N N R 41.977 32.450 53.114 -1.658 -0.289 0.135 "C4'" AP2 11 AP2 "O4'" O4* O 0 1 N N N 41.311 31.442 53.940 -0.439 -0.339 0.907 "O4'" AP2 12 AP2 "C3'" C3* C 0 1 N N S 43.473 32.249 53.389 -2.588 0.656 0.926 "C3'" AP2 13 AP2 "O3'" O3* O 0 1 N N N 44.075 33.474 53.814 -3.939 0.197 0.865 "O3'" AP2 14 AP2 "C2'" C2* C 0 1 N N R 43.550 31.113 54.538 -2.054 0.582 2.376 "C2'" AP2 15 AP2 "O2'" O2* O 0 1 N N N 44.559 31.082 55.582 -3.061 0.077 3.255 "O2'" AP2 16 AP2 "C1'" C1* C 0 1 N N R 42.185 31.346 55.140 -0.863 -0.397 2.286 "C1'" AP2 17 AP2 N9 N9 N 0 1 Y N N 41.606 30.300 56.053 0.220 0.034 3.172 N9 AP2 18 AP2 C8 C8 C 0 1 Y N N 41.488 28.948 55.787 1.230 0.892 2.852 C8 AP2 19 AP2 N7 N7 N 0 1 Y N N 41.291 28.175 56.840 2.016 1.054 3.876 N7 AP2 20 AP2 C5 C5 C 0 1 Y N N 41.280 29.113 57.901 1.559 0.317 4.917 C5 AP2 21 AP2 C6 C6 C 0 1 Y N N 41.101 28.955 59.366 1.990 0.096 6.236 C6 AP2 22 AP2 N6 N6 N 0 1 N N N 40.909 27.733 59.917 3.124 0.721 6.724 N6 AP2 23 AP2 N1 N1 N 0 1 Y N N 41.152 30.113 60.073 1.281 -0.723 7.005 N1 AP2 24 AP2 C2 C2 C 0 1 Y N N 41.344 31.339 59.532 0.198 -1.323 6.548 C2 AP2 25 AP2 N3 N3 N 0 1 Y N N 41.514 31.568 58.211 -0.239 -1.151 5.318 N3 AP2 26 AP2 C4 C4 C 0 1 Y N N 41.470 30.404 57.447 0.404 -0.350 4.476 C4 AP2 27 AP2 HOB2 2HOB H 0 0 N N N 43.629 33.415 48.338 2.369 -0.722 -7.678 HOB2 AP2 28 AP2 HOB3 3HOB H 0 0 N N N 43.685 32.113 50.399 -0.511 -1.048 -6.856 HOB3 AP2 29 AP2 H3A1 1H3A H 0 0 N N N 41.057 31.688 47.578 1.892 -1.025 -3.805 H3A1 AP2 30 AP2 H3A2 2H3A H 0 0 N N N 41.095 30.667 49.015 0.530 -1.967 -4.455 H3A2 AP2 31 AP2 HOA2 2HOA H 0 0 N N N 38.608 33.469 49.455 -1.953 -0.747 -4.269 HOA2 AP2 32 AP2 "H5'1" 1H5* H 0 0 N N N 42.346 31.205 51.322 -2.316 0.329 -1.820 "H5'1" AP2 33 AP2 "H5'2" 2H5* H 0 0 N N N 42.650 32.863 51.047 -0.953 1.271 -1.170 "H5'2" AP2 34 AP2 "H4'" H4* H 0 1 N N N 41.494 33.425 53.357 -2.101 -1.282 0.061 "H4'" AP2 35 AP2 "H3'" H3* H 0 1 N N N 44.030 31.934 52.476 -2.514 1.674 0.542 "H3'" AP2 36 AP2 "HO3'" *HO3 H 0 0 N N N 45.001 33.349 53.984 -4.471 0.824 1.374 "HO3'" AP2 37 AP2 "H2'" H2* H 0 1 N N N 43.847 30.147 54.067 -1.715 1.564 2.709 "H2'" AP2 38 AP2 "HO2'" *HO2 H 0 0 N N N 44.604 30.414 56.256 -3.800 0.701 3.221 "HO2'" AP2 39 AP2 "H1'" H1* H 0 1 N N N 42.262 32.230 55.814 -1.183 -1.407 2.543 "H1'" AP2 40 AP2 H8 H8 H 0 1 N N N 41.548 28.505 54.778 1.358 1.367 1.891 H8 AP2 41 AP2 HN61 1HN6 H 0 0 N N N 40.786 27.624 60.923 3.409 0.563 7.638 HN61 AP2 42 AP2 HN62 2HN6 H 0 0 N N N 41.677 27.129 59.624 3.636 1.314 6.152 HN62 AP2 43 AP2 H2 H2 H 0 1 N N N 41.363 32.207 60.211 -0.349 -1.981 7.207 H2 AP2 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 AP2 PB O1B DOUB N N 1 AP2 PB O2B SING N N 2 AP2 PB O3B SING N N 3 AP2 PB C3A SING N N 4 AP2 O2B HOB2 SING N N 5 AP2 O3B HOB3 SING N N 6 AP2 C3A PA SING N N 7 AP2 C3A H3A1 SING N N 8 AP2 C3A H3A2 SING N N 9 AP2 PA O1A DOUB N N 10 AP2 PA O2A SING N N 11 AP2 PA "O5'" SING N N 12 AP2 O2A HOA2 SING N N 13 AP2 "O5'" "C5'" SING N N 14 AP2 "C5'" "C4'" SING N N 15 AP2 "C5'" "H5'1" SING N N 16 AP2 "C5'" "H5'2" SING N N 17 AP2 "C4'" "O4'" SING N N 18 AP2 "C4'" "C3'" SING N N 19 AP2 "C4'" "H4'" SING N N 20 AP2 "O4'" "C1'" SING N N 21 AP2 "C3'" "O3'" SING N N 22 AP2 "C3'" "C2'" SING N N 23 AP2 "C3'" "H3'" SING N N 24 AP2 "O3'" "HO3'" SING N N 25 AP2 "C2'" "O2'" SING N N 26 AP2 "C2'" "C1'" SING N N 27 AP2 "C2'" "H2'" SING N N 28 AP2 "O2'" "HO2'" SING N N 29 AP2 "C1'" N9 SING N N 30 AP2 "C1'" "H1'" SING N N 31 AP2 N9 C8 SING Y N 32 AP2 N9 C4 SING Y N 33 AP2 C8 N7 DOUB Y N 34 AP2 C8 H8 SING N N 35 AP2 N7 C5 SING Y N 36 AP2 C5 C6 SING Y N 37 AP2 C5 C4 DOUB Y N 38 AP2 C6 N6 SING N N 39 AP2 C6 N1 DOUB Y N 40 AP2 N6 HN61 SING N N 41 AP2 N6 HN62 SING N N 42 AP2 N1 C2 SING Y N 43 AP2 C2 N3 DOUB Y N 44 AP2 C2 H2 SING N N 45 AP2 N3 C4 SING Y N 46 # 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 AP2 SMILES ACDLabs 10.04 "O=P(O)(O)CP(=O)(O)OCC3OC(n2cnc1c(ncnc12)N)C(O)C3O" AP2 SMILES_CANONICAL CACTVS 3.341 "Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P@@](O)(=O)C[P](O)(O)=O)[C@@H](O)[C@H]3O" AP2 SMILES CACTVS 3.341 "Nc1ncnc2n(cnc12)[CH]3O[CH](CO[P](O)(=O)C[P](O)(O)=O)[CH](O)[CH]3O" AP2 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO[P@@](=O)(CP(=O)(O)O)O)O)O)N" AP2 SMILES "OpenEye OEToolkits" 1.5.0 "c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COP(=O)(CP(=O)(O)O)O)O)O)N" AP2 InChI InChI 1.03 "InChI=1S/C11H17N5O9P2/c12-9-6-10(14-2-13-9)16(3-15-6)11-8(18)7(17)5(25-11)1-24-27(22,23)4-26(19,20)21/h2-3,5,7-8,11,17-18H,1,4H2,(H,22,23)(H2,12,13,14)(H2,19,20,21)/t5-,7-,8-,11-/m1/s1" AP2 InChIKey InChI 1.03 OLCWZBFDIYXLAA-IOSLPCCCSA-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 AP2 "SYSTEMATIC NAME" ACDLabs 10.04 "5'-O-[(R)-hydroxy(phosphonomethyl)phosphoryl]adenosine" AP2 "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]methylphosphonic 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 AP2 "Create component" 1999-07-08 RCSB AP2 "Modify descriptor" 2011-06-04 RCSB #