data_EFG # _chem_comp.id EFG _chem_comp.name "1-(2-deoxy-2-fluoro-5-O-phosphono-beta-D-arabinofuranosyl)-1H-imidazo[2,1-b]purin-4(5H)-one" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C12 H13 F N5 O7 P" _chem_comp.mon_nstd_parent_comp_id DG _chem_comp.pdbx_synonyms "2'-F-N2,3-etheno-2'-deoxyarabinoguanosine" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2012-01-04 _chem_comp.pdbx_modified_date 2020-06-17 _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 389.233 _chem_comp.one_letter_code ? _chem_comp.three_letter_code EFG _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag Y _chem_comp.pdbx_ideal_coordinates_details Corina _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 3V6H _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 EFG O6 O6 O 0 1 N N N 7.755 9.881 45.807 -5.076 -2.915 0.579 O6 EFG 1 EFG C6 C6 C 0 1 N N N 7.183 9.797 46.897 -4.581 -1.868 0.201 C6 EFG 2 EFG N1 N1 N 0 1 N N N 6.992 10.965 47.618 -5.345 -0.918 -0.376 N1 EFG 3 EFG C2 C2 C 0 1 Y N N 6.348 10.882 48.838 -4.788 0.272 -0.807 C2 EFG 4 EFG N2 N2 N 0 1 Y N N 6.018 11.796 49.741 -5.335 1.319 -1.387 N2 EFG 5 EFG C10 C10 C 0 1 Y N N 5.412 11.183 50.745 -4.391 2.243 -1.622 C10 EFG 6 EFG C9 C9 C 0 1 Y N N 5.363 9.876 50.447 -3.213 1.769 -1.179 C9 EFG 7 EFG N3 N3 N 0 1 Y N N 5.936 9.694 49.260 -3.455 0.518 -0.660 N3 EFG 8 EFG C4 C4 C 0 1 Y N N 6.112 8.559 48.578 -2.623 -0.416 -0.077 C4 EFG 9 EFG C5 C5 C 0 1 Y N N 6.739 8.620 47.392 -3.148 -1.618 0.372 C5 EFG 10 EFG N7 N7 N 0 1 Y N N 6.802 7.384 46.913 -2.126 -2.335 0.901 N7 EFG 11 EFG C8 C8 C 0 1 Y N N 6.229 6.573 47.796 -1.027 -1.644 0.804 C8 EFG 12 EFG N9 N9 N 0 1 Y N N 5.785 7.292 48.823 -1.290 -0.452 0.197 N9 EFG 13 EFG "C1'" "C1'" C 0 1 N N R 5.126 6.756 50.057 -0.318 0.605 -0.093 "C1'" EFG 14 EFG "O4'" "O4'" O 0 1 N N N 6.154 5.912 50.674 1.013 0.051 -0.188 "O4'" EFG 15 EFG "C2'" "C2'" C 0 1 N N S 3.870 5.910 49.882 -0.246 1.607 1.080 "C2'" EFG 16 EFG F F F 0 1 N N N 3.564 5.580 48.563 -0.662 0.999 2.270 F EFG 17 EFG "C3'" "C3'" C 0 1 N N R 4.167 4.565 50.496 1.250 1.985 1.160 "C3'" EFG 18 EFG "O3'" "O3'" O 0 1 N N N 3.575 4.510 51.766 1.425 3.385 0.933 "O3'" EFG 19 EFG "C4'" "C4'" C 0 1 N N R 5.698 4.518 50.700 1.905 1.167 0.024 "C4'" EFG 20 EFG "C5'" "C5'" C 0 1 N N N 6.357 3.621 49.635 3.286 0.670 0.455 "C5'" EFG 21 EFG "O5'" "O5'" O 0 1 N N N 5.529 3.562 48.463 3.891 -0.047 -0.623 "O5'" EFG 22 EFG P P P 0 1 N N N 5.872 2.560 47.282 5.354 -0.713 -0.521 P EFG 23 EFG OP1 OP1 O 0 1 N N N 5.873 1.192 47.858 6.338 0.317 -0.119 OP1 EFG 24 EFG OP2 OP2 O 0 1 N N N 5.070 2.836 46.077 5.332 -1.891 0.576 OP2 EFG 25 EFG H1 H1 H 0 1 N N N 7.312 11.844 47.265 -6.296 -1.071 -0.491 H1 EFG 26 EFG H9 H9 H 0 1 N N N 5.027 11.649 51.640 -4.551 3.205 -2.088 H9 EFG 27 EFG H10 H10 H 0 1 N N N 4.932 9.103 51.065 -2.260 2.274 -1.223 H10 EFG 28 EFG H8 H8 H 0 1 N N N 6.138 5.501 47.696 -0.055 -1.969 1.145 H8 EFG 29 EFG "H1'" "H1'" H 0 1 N N N 4.892 7.595 50.729 -0.582 1.118 -1.018 "H1'" EFG 30 EFG "H2'" "H2'" H 0 1 N N N 3.021 6.385 50.396 -0.852 2.487 0.868 "H2'" EFG 31 EFG "H3'" "H3'" H 0 1 N N N 3.839 3.747 49.837 1.666 1.699 2.126 "H3'" EFG 32 EFG "HO3'" "HO3'" H 0 0 N N N 3.755 3.666 52.164 0.982 3.947 1.583 "HO3'" EFG 33 EFG "H4'" "H4'" H 0 1 N N N 5.902 4.087 51.691 1.982 1.769 -0.881 "H4'" EFG 34 EFG "H5'" "H5'" H 0 1 N N N 6.486 2.607 50.042 3.912 1.521 0.722 "H5'" EFG 35 EFG "H5''" "H5''" H 0 0 N N N 7.340 4.036 49.366 3.183 0.011 1.317 "H5''" EFG 36 EFG OP3 OP3 O 0 1 N Y N ? ? ? 5.767 -1.322 -1.953 OP3 EFG 37 EFG HOP3 HOP3 H 0 0 N Y N ? ? ? 6.639 -1.740 -1.966 HOP3 EFG 38 EFG HOP2 HOP2 H 0 0 N N N 4.624 2.043 45.804 4.708 -2.603 0.377 HOP2 EFG 39 # # 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 EFG O6 C6 DOUB N N 1 EFG OP2 P SING N N 2 EFG C6 C5 SING N N 3 EFG C6 N1 SING N N 4 EFG N7 C5 SING Y N 5 EFG N7 C8 DOUB Y N 6 EFG P OP1 DOUB N N 7 EFG P "O5'" SING N N 8 EFG C5 C4 DOUB Y N 9 EFG N1 C2 SING N N 10 EFG C8 N9 SING Y N 11 EFG "O5'" "C5'" SING N N 12 EFG F "C2'" SING N N 13 EFG C4 N9 SING Y N 14 EFG C4 N3 SING N N 15 EFG N9 "C1'" SING N N 16 EFG C2 N3 SING Y N 17 EFG C2 N2 DOUB Y N 18 EFG N3 C9 SING Y N 19 EFG "C5'" "C4'" SING N N 20 EFG N2 C10 SING Y N 21 EFG "C2'" "C1'" SING N N 22 EFG "C2'" "C3'" SING N N 23 EFG "C1'" "O4'" SING N N 24 EFG C9 C10 DOUB Y N 25 EFG "C3'" "C4'" SING N N 26 EFG "C3'" "O3'" SING N N 27 EFG "O4'" "C4'" SING N N 28 EFG N1 H1 SING N N 29 EFG C10 H9 SING N N 30 EFG C9 H10 SING N N 31 EFG C8 H8 SING N N 32 EFG "C1'" "H1'" SING N N 33 EFG "C2'" "H2'" SING N N 34 EFG "C3'" "H3'" SING N N 35 EFG "O3'" "HO3'" SING N N 36 EFG "C4'" "H4'" SING N N 37 EFG "C5'" "H5'" SING N N 38 EFG "C5'" "H5''" SING N N 39 EFG P OP3 SING N N 40 EFG OP3 HOP3 SING N N 41 EFG OP2 HOP2 SING N N 42 # # 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 EFG SMILES ACDLabs 12.01 "O=P(O)(O)OCC4OC(n1cnc3c1n2ccnc2NC3=O)C(F)C4O" EFG InChI InChI 1.03 "InChI=1S/C12H13FN5O7P/c13-6-8(19)5(3-24-26(21,22)23)25-11(6)18-4-15-7-9(20)16-12-14-1-2-17(12)10(7)18/h1-2,4-6,8,11,19H,3H2,(H,14,16,20)(H2,21,22,23)/t5-,6+,8-,11-/m1/s1" EFG InChIKey InChI 1.03 CNUAFEDIAQGGKR-WCGPTHBMSA-N EFG SMILES_CANONICAL CACTVS 3.370 "O[C@H]1[C@H](F)[C@@H](O[C@@H]1CO[P](O)(O)=O)n2cnc3C(=O)Nc4nccn4c23" EFG SMILES CACTVS 3.370 "O[CH]1[CH](F)[CH](O[CH]1CO[P](O)(O)=O)n2cnc3C(=O)Nc4nccn4c23" EFG SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "c1cn-2c(n1)NC(=O)c3c2n(cn3)[C@H]4[C@H]([C@@H]([C@H](O4)COP(=O)(O)O)O)F" EFG SMILES "OpenEye OEToolkits" 1.7.6 "c1cn-2c(n1)NC(=O)c3c2n(cn3)C4C(C(C(O4)COP(=O)(O)O)O)F" # # 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 EFG "SYSTEMATIC NAME" ACDLabs 12.01 "1-(2-deoxy-2-fluoro-5-O-phosphono-beta-D-arabinofuranosyl)-1H-imidazo[2,1-b]purin-4(5H)-one" EFG "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "[(2R,3R,4S,5R)-4-fluoranyl-3-oxidanyl-5-(4-oxidanylidene-5H-imidazo[2,1-b]purin-1-yl)oxolan-2-yl]methyl dihydrogen 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 EFG "Create component" 2012-01-04 RCSB EFG "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id EFG _pdbx_chem_comp_synonyms.name "2'-F-N2,3-etheno-2'-deoxyarabinoguanosine" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##