data_F3A # _chem_comp.id F3A _chem_comp.name "2'-deoxy-5'-O-[(S)-{difluoro[(S)-hydroxy(phosphonooxy)phosphoryl]methyl}(hydroxy)phosphoryl]adenosine" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C11 H16 F2 N5 O11 P3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2011-09-07 _chem_comp.pdbx_modified_date 2012-03-16 _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 525.190 _chem_comp.one_letter_code ? _chem_comp.three_letter_code F3A _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 3TFR _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 F3A N1 N1 N 0 1 Y N N 9.637 8.393 8.177 -8.419 -1.965 -0.848 N1 F3A 1 F3A C2 C2 C 0 1 Y N N 8.382 8.489 7.585 -7.986 -1.027 -1.671 C2 F3A 2 F3A N3 N3 N 0 1 Y N N 7.223 8.180 8.314 -6.854 -0.384 -1.477 N3 F3A 3 F3A C4 C4 C 0 1 Y N N 7.357 7.792 9.607 -6.089 -0.660 -0.426 C4 F3A 4 F3A C5 C5 C 0 1 Y N N 8.623 7.693 10.208 -6.506 -1.650 0.480 C5 F3A 5 F3A C6 C6 C 0 1 Y N N 9.762 8.005 9.478 -7.722 -2.309 0.230 C6 F3A 6 F3A N6 N6 N 0 1 N N N 11.054 7.850 10.088 -8.183 -3.293 1.087 N6 F3A 7 F3A N7 N7 N 0 1 Y N N 8.458 7.262 11.535 -5.558 -1.732 1.445 N7 F3A 8 F3A C8 C8 C 0 1 Y N N 7.119 7.092 11.760 -4.610 -0.877 1.195 C8 F3A 9 F3A N9 N9 N 0 1 Y N N 6.437 7.457 10.559 -4.892 -0.191 0.051 N9 F3A 10 F3A PA PA P 0 1 N N N 4.985 5.345 15.032 1.664 1.205 0.619 PA F3A 11 F3A PB PB P 0 1 N N N 3.842 2.568 14.107 4.372 0.002 0.333 PB F3A 12 F3A PG PG P 0 1 N N N 3.679 1.201 16.481 6.820 -1.463 -0.469 PG F3A 13 F3A "C1'" "C1'" C 0 1 N N R 5.034 7.252 10.340 -4.066 0.855 -0.558 "C1'" F3A 14 F3A F1A F1A F 0 1 N N N 6.108 3.729 13.403 2.135 -1.164 -0.451 F1A F3A 15 F3A O1A O1A O 0 1 N N N 3.845 5.453 16.069 1.555 0.606 2.110 O1A F3A 16 F3A O1B O1B O 0 1 N N N 3.904 2.209 12.614 4.272 -0.549 1.704 O1B F3A 17 F3A O1G O1G O 0 1 N N N 4.850 0.490 17.218 7.308 -1.984 -1.913 O1G F3A 18 F3A "C2'" "C2'" C 0 1 N N N 4.412 5.990 9.763 -4.495 2.247 -0.043 "C2'" F3A 19 F3A F2A F2A F 0 1 N N N 5.974 2.965 15.451 2.802 0.632 -1.696 F2A F3A 20 F3A O2A O2A O 0 1 N N N 6.228 5.928 15.612 2.270 2.555 0.673 O2A F3A 21 F3A O2B O2B O 0 1 N N N 2.532 3.215 14.389 5.030 1.470 0.392 O2B F3A 22 F3A O2G O2G O 0 1 N N N 2.361 0.420 16.777 7.680 -0.340 -0.034 O2G F3A 23 F3A "C3'" "C3'" C 0 1 N N S 3.933 5.332 10.985 -3.167 3.025 0.087 "C3'" F3A 24 F3A "O3'" "O3'" O 0 1 N N N 3.207 4.161 10.885 -3.170 4.168 -0.771 "O3'" F3A 25 F3A C3A C3A C 0 1 N N N 5.317 3.612 14.485 2.707 0.112 -0.400 C3A F3A 26 F3A O3B O3B O 0 1 N N N 3.945 1.238 14.937 5.293 -0.964 -0.567 O3B F3A 27 F3A O3G O3G O 0 1 N N N 3.631 2.607 16.992 6.925 -2.664 0.598 O3G F3A 28 F3A "C4'" "C4'" C 0 1 N N R 3.360 6.480 11.802 -2.092 2.011 -0.365 "C4'" F3A 29 F3A "O4'" "O4'" O 0 1 N N N 3.983 7.728 11.279 -2.690 0.716 -0.142 "O4'" F3A 30 F3A "C5'" "C5'" C 0 1 N N N 3.330 6.307 13.283 -0.826 2.165 0.479 "C5'" F3A 31 F3A "O5'" "O5'" O 0 1 N N N 4.629 6.242 13.787 0.193 1.302 -0.029 "O5'" F3A 32 F3A H2 H2 H 0 1 N N N 8.299 8.804 6.555 -8.584 -0.779 -2.535 H2 F3A 33 F3A HN6 HN6 H 0 1 N N N 11.766 8.066 9.420 -9.024 -3.740 0.904 HN6 F3A 34 F3A HN6A HN6A H 0 0 N N N 11.130 8.470 10.869 -7.665 -3.535 1.871 HN6A F3A 35 F3A H8 H8 H 0 1 N N N 6.663 6.746 12.676 -3.730 -0.731 1.804 H8 F3A 36 F3A "H1'" "H1'" H 0 1 N N N 5.303 7.969 9.550 -4.141 0.812 -1.645 "H1'" F3A 37 F3A HO1A HO1A H 0 0 N N N 4.173 5.867 16.859 1.166 -0.278 2.151 HO1A F3A 38 F3A HO1G HO1G H 0 0 N N N 4.517 -0.264 17.689 8.222 -2.301 -1.928 HO1G F3A 39 F3A "H2'" "H2'" H 0 1 N N N 3.597 6.209 9.057 -5.154 2.734 -0.762 "H2'" F3A 40 F3A "H2'A" "H2'A" H 0 0 N N N 5.141 5.376 9.214 -4.984 2.161 0.928 "H2'A" F3A 41 F3A HO2B HO2B H 0 0 N N N 2.024 3.264 13.588 5.127 1.892 -0.472 HO2B F3A 42 F3A "H3'" "H3'" H 0 1 N N N 4.756 4.825 11.510 -2.999 3.323 1.122 "H3'" F3A 43 F3A "HO3'" "HO3'" H 0 0 N N N 3.521 3.537 11.529 -3.865 4.809 -0.569 "HO3'" F3A 44 F3A HO3G HO3G H 0 0 N N N 2.792 2.764 17.409 6.386 -3.436 0.376 HO3G F3A 45 F3A "H4'" "H4'" H 0 1 N N N 2.271 6.526 11.655 -1.862 2.148 -1.422 "H4'" F3A 46 F3A "H5'" "H5'" H 0 1 N N N 2.808 7.162 13.737 -0.482 3.199 0.434 "H5'" F3A 47 F3A "H5'A" "H5'A" H 0 0 N N N 2.799 5.375 13.528 -1.044 1.900 1.514 "H5'A" F3A 48 # 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 F3A C2 N1 DOUB Y N 1 F3A N1 C6 SING Y N 2 F3A C2 N3 SING Y N 3 F3A C2 H2 SING N N 4 F3A N3 C4 DOUB Y N 5 F3A C4 C5 SING Y N 6 F3A C4 N9 SING Y N 7 F3A C6 C5 DOUB Y N 8 F3A C5 N7 SING Y N 9 F3A C6 N6 SING N N 10 F3A N6 HN6 SING N N 11 F3A N6 HN6A SING N N 12 F3A N7 C8 DOUB Y N 13 F3A N9 C8 SING Y N 14 F3A C8 H8 SING N N 15 F3A "C1'" N9 SING N N 16 F3A "O5'" PA SING N N 17 F3A C3A PA SING N N 18 F3A PA O2A DOUB N N 19 F3A PA O1A SING N N 20 F3A O1B PB DOUB N N 21 F3A PB O2B SING N N 22 F3A PB C3A SING N N 23 F3A PB O3B SING N N 24 F3A O3B PG SING N N 25 F3A PG O2G DOUB N N 26 F3A PG O3G SING N N 27 F3A PG O1G SING N N 28 F3A "C2'" "C1'" SING N N 29 F3A "C1'" "O4'" SING N N 30 F3A "C1'" "H1'" SING N N 31 F3A F1A C3A SING N N 32 F3A O1A HO1A SING N N 33 F3A O1G HO1G SING N N 34 F3A "C2'" "C3'" SING N N 35 F3A "C2'" "H2'" SING N N 36 F3A "C2'" "H2'A" SING N N 37 F3A C3A F2A SING N N 38 F3A O2B HO2B SING N N 39 F3A "O3'" "C3'" SING N N 40 F3A "C3'" "C4'" SING N N 41 F3A "C3'" "H3'" SING N N 42 F3A "O3'" "HO3'" SING N N 43 F3A O3G HO3G SING N N 44 F3A "O4'" "C4'" SING N N 45 F3A "C4'" "C5'" SING N N 46 F3A "C4'" "H4'" SING N N 47 F3A "C5'" "O5'" SING N N 48 F3A "C5'" "H5'" SING N N 49 F3A "C5'" "H5'A" SING N N 50 # 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 F3A SMILES ACDLabs 12.01 "O=P(O)(O)OP(=O)(O)C(F)(F)P(=O)(O)OCC3OC(n2cnc1c(ncnc12)N)CC3O" F3A InChI InChI 1.03 "InChI=1S/C11H16F2N5O11P3/c12-11(13,31(22,23)29-32(24,25)26)30(20,21)27-2-6-5(19)1-7(28-6)18-4-17-8-9(14)15-3-16-10(8)18/h3-7,19H,1-2H2,(H,20,21)(H,22,23)(H2,14,15,16)(H2,24,25,26)/t5-,6+,7+/m0/s1" F3A InChIKey InChI 1.03 SRDWTQAPDNVDMA-RRKCRQDMSA-N F3A SMILES_CANONICAL CACTVS 3.370 "Nc1ncnc2n(cnc12)[C@H]3C[C@H](O)[C@@H](CO[P](O)(=O)C(F)(F)[P](O)(=O)O[P](O)(O)=O)O3" F3A SMILES CACTVS 3.370 "Nc1ncnc2n(cnc12)[CH]3C[CH](O)[CH](CO[P](O)(=O)C(F)(F)[P](O)(=O)O[P](O)(O)=O)O3" F3A SMILES_CANONICAL "OpenEye OEToolkits" 1.7.2 "c1nc(c2c(n1)n(cn2)[C@H]3C[C@@H]([C@H](O3)CO[P@](=O)(C(F)(F)[P@](=O)(O)OP(=O)(O)O)O)O)N" F3A SMILES "OpenEye OEToolkits" 1.7.2 "c1nc(c2c(n1)n(cn2)C3CC(C(O3)COP(=O)(C(F)(F)P(=O)(O)OP(=O)(O)O)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 F3A "SYSTEMATIC NAME" ACDLabs 12.01 "2'-deoxy-5'-O-[(S)-{difluoro[(S)-hydroxy(phosphonooxy)phosphoryl]methyl}(hydroxy)phosphoryl]adenosine" F3A "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.2 "[(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-oxidanyl-oxolan-2-yl]methoxy-[bis(fluoranyl)-[oxidanyl(phosphonooxy)phosphoryl]methyl]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 F3A "Create component" 2011-09-07 RCSB #