data_ETV # _chem_comp.id ETV _chem_comp.name "4-AMINO-5-FLUORO-1-[(2R,5S)-2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL]PYRIMIDIN-2(1H)-ONE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C8 H10 F N3 O3 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "5-FLUORO-(-)-L-2',3'-DIDEOXY-3'-THIACYTIDINE; (-)-BETA-2',3'-DIDEOXY-5-FLUORO-3'-THIACYTIDINE; EMTRICITABINE; EMTRIVA" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2006-10-26 _chem_comp.pdbx_modified_date 2020-06-17 _chem_comp.pdbx_ambiguous_flag ? _chem_comp.pdbx_release_status REL _chem_comp.pdbx_replaced_by ? _chem_comp.pdbx_replaces ? _chem_comp.formula_weight 247.247 _chem_comp.one_letter_code ? _chem_comp.three_letter_code ETV _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 ? _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 ETV O4 O4 O 0 1 N N N 38.912 93.856 92.191 3.369 -1.716 -1.491 O4 ETV 1 ETV C9 C9 C 0 1 Y N N 37.714 93.540 92.192 3.430 -1.087 -0.433 C9 ETV 2 ETV N5 N5 N 0 1 Y N N 37.246 92.268 91.918 4.569 -0.361 -0.120 N5 ETV 3 ETV C10 C10 C 0 1 Y N N 35.955 91.999 91.930 4.655 0.314 0.998 C10 ETV 4 ETV N6 N6 N 0 1 N N N 35.549 90.772 91.663 5.790 1.030 1.295 N6 ETV 5 ETV C11 C11 C 0 1 Y N N 35.012 93.046 92.216 3.533 0.320 1.961 C11 ETV 6 ETV F2 F2 F 0 1 N N N 33.681 92.735 92.214 3.676 1.031 3.093 F2 ETV 7 ETV C12 C12 C 0 1 Y N N 35.435 94.294 92.500 2.443 -0.376 1.663 C12 ETV 8 ETV N4 N4 N 0 1 Y N N 36.799 94.538 92.491 2.360 -1.084 0.485 N4 ETV 9 ETV C13 C13 C 0 1 N N S 37.352 95.899 92.765 1.169 -1.828 0.188 C13 ETV 10 ETV O5 O5 O 0 1 N N N 36.232 96.752 92.873 0.604 -2.304 1.415 O5 ETV 11 ETV C15 C15 C 0 1 N N R 36.091 97.401 94.136 -0.707 -2.810 1.130 C15 ETV 12 ETV C16 C16 C 0 1 N N N 34.623 97.566 94.509 -1.578 -2.629 2.360 C16 ETV 13 ETV O6 O6 O 0 1 N N N 34.079 98.491 93.602 -1.637 -1.249 2.681 O6 ETV 14 ETV S2 S2 S 0 1 N N N 36.962 96.322 95.283 -1.385 -1.918 -0.295 S2 ETV 15 ETV C14 C14 C 0 1 N N N 38.205 95.968 94.030 0.127 -0.964 -0.505 C14 ETV 16 ETV HN61 1HN6 H 0 0 N N N 36.327 90.173 91.475 6.134 1.665 0.614 HN61 ETV 17 ETV HN62 2HN6 H 0 0 N N N 34.592 90.481 91.650 6.218 0.882 2.178 HN62 ETV 18 ETV H12 H12 H 0 1 N N N 34.731 95.081 92.728 1.587 -0.413 2.327 H12 ETV 19 ETV H13 H13 H 0 1 N N N 38.033 96.193 91.953 1.468 -2.686 -0.427 H13 ETV 20 ETV H15 H15 H 0 1 N N N 36.502 98.421 94.139 -0.623 -3.873 0.885 H15 ETV 21 ETV H161 1H16 H 0 0 N N N 34.528 97.938 95.540 -1.156 -3.173 3.208 H161 ETV 22 ETV H162 2H16 H 0 0 N N N 34.092 96.604 94.458 -2.591 -2.992 2.165 H162 ETV 23 ETV HO6 HO6 H 0 1 N N N 33.956 99.327 94.037 -2.560 -0.969 2.561 HO6 ETV 24 ETV H141 1H14 H 0 0 N N N 38.736 95.025 94.226 0.000 0.000 -0.000 H141 ETV 25 ETV H142 2H14 H 0 0 N N N 39.013 96.713 93.982 0.363 -0.783 -1.557 H142 ETV 26 # # 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 ETV O4 C9 DOUB N N 1 ETV C9 N5 SING Y N 2 ETV C9 N4 SING Y N 3 ETV N5 C10 DOUB Y N 4 ETV C10 N6 SING N N 5 ETV C10 C11 SING Y N 6 ETV N6 HN61 SING N N 7 ETV N6 HN62 SING N N 8 ETV C11 F2 SING N N 9 ETV C11 C12 DOUB Y N 10 ETV C12 N4 SING Y N 11 ETV C12 H12 SING N N 12 ETV N4 C13 SING N N 13 ETV C13 O5 SING N N 14 ETV C13 C14 SING N N 15 ETV C13 H13 SING N N 16 ETV O5 C15 SING N N 17 ETV C15 C16 SING N N 18 ETV C15 S2 SING N N 19 ETV C15 H15 SING N N 20 ETV C16 O6 SING N N 21 ETV C16 H161 SING N N 22 ETV C16 H162 SING N N 23 ETV O6 HO6 SING N N 24 ETV S2 C14 SING N N 25 ETV C14 H141 SING N N 26 ETV C14 H142 SING N N 27 # # 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 ETV SMILES ACDLabs 10.04 "FC=1C(=NC(=O)N(C=1)C2OC(SC2)CO)N" ETV SMILES_CANONICAL CACTVS 3.341 "NC1=NC(=O)N(C=C1F)[C@@H]2CS[C@H](CO)O2" ETV SMILES CACTVS 3.341 "NC1=NC(=O)N(C=C1F)[CH]2CS[CH](CO)O2" ETV SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C1[C@H](O[C@H](S1)CO)N2C=C(C(=NC2=O)N)F" ETV SMILES "OpenEye OEToolkits" 1.5.0 "C1C(OC(S1)CO)N2C=C(C(=NC2=O)N)F" ETV InChI InChI 1.03 "InChI=1S/C8H10FN3O3S/c9-4-1-12(8(14)11-7(4)10)5-3-16-6(2-13)15-5/h1,5-6,13H,2-3H2,(H2,10,11,14)/t5-,6+/m0/s1" ETV InChIKey InChI 1.03 XQSPYNMVSIKCOC-NTSWFWBYSA-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 ETV "SYSTEMATIC NAME" ACDLabs 10.04 "4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2(1H)-one" ETV "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site ETV "Create component" 2006-10-26 RCSB ETV "Modify descriptor" 2011-06-04 RCSB ETV "Modify synonyms" 2020-06-05 PDBE # # loop_ _pdbx_chem_comp_synonyms.ordinal _pdbx_chem_comp_synonyms.comp_id _pdbx_chem_comp_synonyms.name _pdbx_chem_comp_synonyms.provenance _pdbx_chem_comp_synonyms.type 1 ETV "5-FLUORO-(-)-L-2',3'-DIDEOXY-3'-THIACYTIDINE" ? ? 2 ETV "(-)-BETA-2',3'-DIDEOXY-5-FLUORO-3'-THIACYTIDINE" ? ? 3 ETV EMTRICITABINE ? ? 4 ETV EMTRIVA ? ? ##