data_ET9 # _chem_comp.id ET9 _chem_comp.name ;[[(1R,3S,5S)-3-(2-azanyl-6-oxidanylidene-3H-purin-9-yl)-2-methylidene-5-oxidanyl-cyclopentyl]methoxy-oxidanyl-phosphory l] phosphono hydrogen phosphate ; _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C12 H18 N5 O12 P3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "Entecavir 5'-triphosphate" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2017-05-30 _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 517.219 _chem_comp.one_letter_code ? _chem_comp.three_letter_code ET9 _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 5XN1 _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site PDBJ # # 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 ET9 "C1'" C1 C 0 1 N N S 180.350 276.491 -124.153 3.522 -1.409 -1.272 "C1'" ET9 1 ET9 C2 C2 C 0 1 N N N 181.476 272.313 -124.954 6.731 1.804 -1.322 C2 ET9 2 ET9 "C2'" C3 C 0 1 N N N 180.587 276.327 -122.663 3.750 -2.902 -0.927 "C2'" ET9 3 ET9 "C3'" C4 C 0 1 N N S 180.984 277.679 -122.121 2.606 -3.187 0.079 "C3'" ET9 4 ET9 C4 C5 C 0 1 Y N N 181.721 274.617 -124.964 5.069 0.383 -0.407 C4 ET9 5 ET9 "C4'" C6 C 0 1 N N R 180.339 278.706 -123.020 1.422 -2.363 -0.469 "C4'" ET9 6 ET9 C44 C7 C 0 1 N N N 180.034 278.537 -125.446 1.344 -0.339 -1.971 C44 ET9 7 ET9 C5 C8 C 0 1 Y N N 182.998 274.447 -125.610 5.295 0.951 0.841 C5 ET9 8 ET9 "C5'" C9 C 0 1 N N N 181.158 279.958 -123.211 0.621 -1.764 0.689 "C5'" ET9 9 ET9 C6 C10 C 0 1 N N N 183.424 273.069 -125.897 6.319 1.995 0.950 C6 ET9 10 ET9 "C6'" C11 C 0 1 N N N 180.238 277.960 -124.298 2.012 -1.257 -1.318 "C6'" ET9 11 ET9 C8 C12 C 0 1 Y N N 182.586 276.551 -125.290 3.746 -0.540 1.086 C8 ET9 12 ET9 N1 N1 N 0 1 N N N 182.632 272.089 -125.543 6.979 2.365 -0.158 N1 ET9 13 ET9 N2 N2 N 0 1 N N N 180.735 271.262 -124.626 7.440 2.219 -2.418 N2 ET9 14 ET9 N3 N3 N 0 1 N N N 181.019 273.527 -124.662 5.801 0.826 -1.478 N3 ET9 15 ET9 N7 N4 N 0 1 Y N N 183.470 275.676 -125.788 4.458 0.349 1.718 N7 ET9 16 ET9 N9 N5 N 0 1 Y N N 181.534 275.909 -124.806 4.094 -0.550 -0.233 N9 ET9 17 ET9 O1A O1 O 0 1 N N N 183.609 281.635 -122.792 -0.909 0.900 1.837 O1A ET9 18 ET9 O1B O2 O 0 1 N N N 182.635 281.051 -120.478 -4.907 -0.141 1.637 O1B ET9 19 ET9 O1G O3 O 0 1 N N N 186.864 281.282 -119.774 -7.114 0.815 -2.599 O1G ET9 20 ET9 O2A O4 O 0 1 N N N 184.901 279.993 -123.972 -2.108 -1.300 2.141 O2A ET9 21 ET9 O2B O5 O 0 1 N N N 182.706 278.687 -119.722 -4.265 2.220 1.020 O2B ET9 22 ET9 O2G O6 O 0 1 N N N 185.304 281.869 -117.966 -7.507 -0.771 -0.539 O2G ET9 23 ET9 "O3'" O7 O 0 1 N N N 180.551 277.793 -120.782 2.285 -4.579 0.094 "O3'" ET9 24 ET9 O3A O8 O 0 1 N N N 183.966 279.330 -121.768 -2.843 0.160 0.217 O3A ET9 25 ET9 O3B O9 O 0 1 N N N 184.741 280.046 -119.495 -5.249 0.558 -0.764 O3B ET9 26 ET9 O3G O10 O 0 1 N N N 184.781 282.417 -120.278 -7.426 1.737 -0.271 O3G ET9 27 ET9 "O5'" O11 O 0 1 N N N 182.420 279.619 -123.751 -0.537 -1.102 0.175 "O5'" ET9 28 ET9 O6 O12 O 0 1 N N N 184.491 272.804 -126.439 6.556 2.527 2.024 O6 ET9 29 ET9 PA P1 P 0 1 N N N 183.737 280.185 -123.082 -1.610 -0.356 1.115 PA ET9 30 ET9 PB P2 P 0 1 N N N 183.437 279.795 -120.353 -4.329 0.681 0.551 PB ET9 31 ET9 PG P3 P 0 1 N N N 185.453 281.461 -119.372 -6.837 0.610 -1.026 PG ET9 32 ET9 H1 H1 H 0 1 N N N 179.425 275.983 -124.463 3.958 -1.173 -2.243 H1 ET9 33 ET9 H2 H2 H 0 1 N N N 179.666 275.980 -122.171 3.649 -3.525 -1.815 H2 ET9 34 ET9 H3 H3 H 0 1 N N N 181.393 275.599 -122.488 4.723 -3.047 -0.458 H3 ET9 35 ET9 H4 H4 H 0 1 N N N 182.077 277.784 -122.182 2.881 -2.848 1.078 H4 ET9 36 ET9 H5 H5 H 0 1 N N N 179.338 278.962 -122.644 0.778 -2.997 -1.078 H5 ET9 37 ET9 H6 H6 H 0 1 N N N 179.929 279.611 -125.500 1.872 0.405 -2.549 H6 ET9 38 ET9 H7 H7 H 0 1 N N N 179.969 277.942 -126.345 0.265 -0.327 -1.933 H7 ET9 39 ET9 H8 H8 H 0 1 N N N 181.297 280.457 -122.240 0.313 -2.559 1.368 H8 ET9 40 ET9 H9 H9 H 0 1 N N N 180.635 280.637 -123.901 1.241 -1.046 1.226 H9 ET9 41 ET9 H10 H10 H 0 1 N N N 182.713 277.623 -125.284 2.996 -1.172 1.538 H10 ET9 42 ET9 H11 H11 H 0 1 N N N 181.061 270.338 -124.828 7.274 1.816 -3.284 H11 ET9 43 ET9 H12 H12 H 0 1 N N N 179.851 271.394 -124.177 8.108 2.916 -2.327 H12 ET9 44 ET9 H13 H13 H 0 1 N N N 180.133 273.623 -124.208 5.653 0.438 -2.355 H13 ET9 45 ET9 H14 H14 H 0 1 N N N 184.299 282.110 -123.240 -0.559 1.561 1.224 H14 ET9 46 ET9 H15 H15 H 0 1 N N N 187.048 281.821 -120.535 -8.052 0.855 -2.831 H15 ET9 47 ET9 H16 H16 H 0 1 N N N 181.828 278.973 -119.499 -3.895 2.818 0.356 H16 ET9 48 ET9 H17 H17 H 0 1 N N N 184.801 282.673 -117.921 -7.168 -1.554 -0.993 H17 ET9 49 ET9 H18 H18 H 0 1 N N N 180.980 277.131 -120.253 3.016 -5.148 0.369 H18 ET9 50 # # 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 ET9 O6 C6 DOUB N N 1 ET9 C6 C5 SING N N 2 ET9 C6 N1 SING N N 3 ET9 N7 C5 SING Y N 4 ET9 N7 C8 DOUB Y N 5 ET9 C5 C4 DOUB Y N 6 ET9 N1 C2 DOUB N N 7 ET9 C44 "C6'" DOUB N N 8 ET9 C8 N9 SING Y N 9 ET9 C4 N9 SING Y N 10 ET9 C4 N3 SING N N 11 ET9 C2 N3 SING N N 12 ET9 C2 N2 SING N N 13 ET9 N9 "C1'" SING N N 14 ET9 "C6'" "C1'" SING N N 15 ET9 "C6'" "C4'" SING N N 16 ET9 "C1'" "C2'" SING N N 17 ET9 O2A PA DOUB N N 18 ET9 "O5'" "C5'" SING N N 19 ET9 "O5'" PA SING N N 20 ET9 "C5'" "C4'" SING N N 21 ET9 PA O1A SING N N 22 ET9 PA O3A SING N N 23 ET9 "C4'" "C3'" SING N N 24 ET9 "C2'" "C3'" SING N N 25 ET9 "C3'" "O3'" SING N N 26 ET9 O3A PB SING N N 27 ET9 O1B PB DOUB N N 28 ET9 PB O2B SING N N 29 ET9 PB O3B SING N N 30 ET9 O3G PG DOUB N N 31 ET9 O1G PG SING N N 32 ET9 O3B PG SING N N 33 ET9 PG O2G SING N N 34 ET9 "C1'" H1 SING N N 35 ET9 "C2'" H2 SING N N 36 ET9 "C2'" H3 SING N N 37 ET9 "C3'" H4 SING N N 38 ET9 "C4'" H5 SING N N 39 ET9 C44 H6 SING N N 40 ET9 C44 H7 SING N N 41 ET9 "C5'" H8 SING N N 42 ET9 "C5'" H9 SING N N 43 ET9 C8 H10 SING N N 44 ET9 N2 H11 SING N N 45 ET9 N2 H12 SING N N 46 ET9 N3 H13 SING N N 47 ET9 O1A H14 SING N N 48 ET9 O1G H15 SING N N 49 ET9 O2B H16 SING N N 50 ET9 O2G H17 SING N N 51 ET9 "O3'" H18 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 ET9 InChI InChI 1.03 "InChI=1S/C12H18N5O12P3/c1-5-6(3-27-31(23,24)29-32(25,26)28-30(20,21)22)8(18)2-7(5)17-4-14-9-10(17)15-12(13)16-11(9)19/h4,6-8,18H,1-3H2,(H,23,24)(H,25,26)(H2,20,21,22)(H3,13,15,16,19)/t6-,7-,8-/m0/s1" ET9 InChIKey InChI 1.03 YMBBDUCQYPKKJK-FXQIFTODSA-N ET9 SMILES_CANONICAL CACTVS 3.385 "NC1=NC(=O)c2ncn([C@H]3C[C@H](O)[C@@H](CO[P](O)(=O)O[P](O)(=O)O[P](O)(O)=O)C3=C)c2N1" ET9 SMILES CACTVS 3.385 "NC1=NC(=O)c2ncn([CH]3C[CH](O)[CH](CO[P](O)(=O)O[P](O)(=O)O[P](O)(O)=O)C3=C)c2N1" ET9 SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "C=C1[C@H](C[C@@H]([C@H]1COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O)n2cnc3c2NC(=NC3=O)N" ET9 SMILES "OpenEye OEToolkits" 2.0.6 "C=C1C(CC(C1COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O)n2cnc3c2NC(=NC3=O)N" # _pdbx_chem_comp_identifier.comp_id ET9 _pdbx_chem_comp_identifier.type "SYSTEMATIC NAME" _pdbx_chem_comp_identifier.program "OpenEye OEToolkits" _pdbx_chem_comp_identifier.program_version 2.0.6 _pdbx_chem_comp_identifier.identifier "[[(1~{R},3~{S},5~{S})-3-(2-azanyl-6-oxidanylidene-3~{H}-purin-9-yl)-2-methylidene-5-oxidanyl-cyclopentyl]methoxy-oxidanyl-phosphoryl] phosphono hydrogen 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 ET9 "Create component" 2017-05-30 PDBJ ET9 "Modify synonyms" 2017-06-19 PDBJ ET9 "Initial release" 2018-02-07 RCSB ET9 "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id ET9 _pdbx_chem_comp_synonyms.name "Entecavir 5'-triphosphate" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##