data_EPS # _chem_comp.id EPS _chem_comp.name "5-[(1-CARBOXYVINYL)OXY]-4-HYDROXY-3-(PHOSPHONOOXY)CYCLOHEX-1-ENE-1-CARBOXYLIC ACID" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C10 H13 O10 P" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms 5-ENOLPYRUVYLSHIKIMATE-3-PHOSPHATE _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2003-09-15 _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 324.178 _chem_comp.one_letter_code ? _chem_comp.three_letter_code EPS _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 1QXO _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 EPS C1 C1 C 0 1 N N N -17.877 9.543 16.790 -2.235 0.111 -0.559 C1 EPS 1 EPS C2 C2 C 0 1 N N N -19.046 9.777 17.578 -1.884 0.160 0.708 C2 EPS 2 EPS C3 C3 C 0 1 N N R -19.900 8.766 18.070 -0.547 0.648 1.188 C3 EPS 3 EPS C4 C4 C 0 1 N N S -19.142 7.558 17.943 0.149 1.443 0.082 C4 EPS 4 EPS C5 C5 C 0 1 N N R -18.773 7.334 16.577 0.106 0.623 -1.212 C5 EPS 5 EPS C6 C6 C 0 1 N N N -17.693 8.214 16.271 -1.345 0.541 -1.688 C6 EPS 6 EPS O3 O3 O 0 1 N N N -20.867 8.683 17.234 0.266 -0.471 1.540 O3 EPS 7 EPS P P P 0 1 N N N -22.082 9.147 18.169 0.637 -0.306 3.098 P EPS 8 EPS O1P O1P O 0 1 N N N -21.756 10.407 19.009 -0.605 -0.287 3.901 O1P EPS 9 EPS O2P O2P O 0 1 N N N -23.461 8.869 17.414 1.559 -1.541 3.564 O2P EPS 10 EPS O3P O3P O 0 1 N N N -22.176 7.887 19.262 1.438 1.073 3.316 O3P EPS 11 EPS O4 O4 O 0 1 N N N -19.855 6.649 18.537 1.508 1.688 0.451 O4 EPS 12 EPS O5 O5 O 0 1 N N N -18.363 6.025 16.421 0.907 1.260 -2.210 O5 EPS 13 EPS C7 C7 C 0 1 N N N -19.088 5.112 15.710 1.373 0.277 -3.027 C7 EPS 14 EPS C8 C8 C 0 1 N N N -20.502 5.299 15.493 0.952 0.205 -4.290 C8 EPS 15 EPS C9 C9 C 0 1 N N N -18.569 3.955 15.147 2.342 -0.707 -2.515 C9 EPS 16 EPS O91 O91 O 0 1 N N N -17.330 3.652 15.305 2.803 -1.681 -3.325 O91 EPS 17 EPS O92 O92 O 0 1 N N N -19.261 3.135 14.393 2.726 -0.641 -1.364 O92 EPS 18 EPS C10 C10 C 0 1 N N N -16.938 10.423 16.211 -3.575 -0.393 -0.887 C10 EPS 19 EPS O11 O11 O 0 1 N N N -15.855 10.093 15.518 -4.324 -0.750 0.000 O11 EPS 20 EPS O12 O12 O 0 1 N N N -16.888 11.733 16.196 -3.974 -0.459 -2.173 O12 EPS 21 EPS H2 H2 H 0 1 N N N -19.309 10.819 17.825 -2.601 -0.165 1.448 H2 EPS 22 EPS H3 H3 H 0 1 N N N -20.261 8.949 19.108 -0.687 1.282 2.064 H3 EPS 23 EPS H4 H4 H 0 1 N N N -18.143 7.573 18.438 -0.366 2.392 -0.067 H4 EPS 24 EPS H5 H5 H 0 1 N N N -19.636 7.523 15.898 0.487 -0.380 -1.023 H5 EPS 25 EPS H61 1H6 H 0 1 N N N -17.503 8.240 15.172 -1.663 1.520 -2.046 H61 EPS 26 EPS H62 2H6 H 0 1 N N N -16.723 7.785 16.615 -1.418 -0.180 -2.501 H62 EPS 27 EPS H2P H2P H 0 1 N N N -24.181 9.144 17.968 1.758 -1.404 4.501 H2P EPS 28 EPS H3P H3P H 0 1 N N N -22.896 8.162 19.816 2.239 1.019 2.776 H3P EPS 29 EPS HO4 HO4 H 0 1 N N N -19.352 5.847 18.452 1.487 2.200 1.271 HO4 EPS 30 EPS H81 1H8 H 0 1 N N N -20.914 6.218 15.940 1.254 -0.623 -4.914 H81 EPS 31 EPS H82 2H8 H 0 1 N N N -21.087 4.561 14.918 0.308 0.974 -4.690 H82 EPS 32 EPS H91 H91 H 0 1 N N N -16.974 2.859 14.919 3.439 -2.328 -2.989 H91 EPS 33 EPS H12 H12 H 0 1 N N N -16.255 12.325 15.806 -4.856 -0.792 -2.389 H12 EPS 34 # # 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 EPS C1 C2 DOUB N N 1 EPS C1 C6 SING N N 2 EPS C1 C10 SING N N 3 EPS C2 C3 SING N N 4 EPS C2 H2 SING N N 5 EPS C3 C4 SING N N 6 EPS C3 O3 SING N N 7 EPS C3 H3 SING N N 8 EPS C4 C5 SING N N 9 EPS C4 O4 SING N N 10 EPS C4 H4 SING N N 11 EPS C5 C6 SING N N 12 EPS C5 O5 SING N N 13 EPS C5 H5 SING N N 14 EPS C6 H61 SING N N 15 EPS C6 H62 SING N N 16 EPS O3 P SING N N 17 EPS P O1P DOUB N N 18 EPS P O2P SING N N 19 EPS P O3P SING N N 20 EPS O2P H2P SING N N 21 EPS O3P H3P SING N N 22 EPS O4 HO4 SING N N 23 EPS O5 C7 SING N N 24 EPS C7 C8 DOUB N N 25 EPS C7 C9 SING N N 26 EPS C8 H81 SING N N 27 EPS C8 H82 SING N N 28 EPS C9 O91 SING N N 29 EPS C9 O92 DOUB N N 30 EPS O91 H91 SING N N 31 EPS C10 O11 DOUB N N 32 EPS C10 O12 SING N N 33 EPS O12 H12 SING N N 34 # # 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 EPS SMILES ACDLabs 10.04 "O=C(O)C1=CC(OP(=O)(O)O)C(O)C(O/C(C(=O)O)=C)C1" EPS SMILES_CANONICAL CACTVS 3.341 "O[C@H]1[C@@H](CC(=C[C@H]1O[P](O)(O)=O)C(O)=O)OC(=C)C(O)=O" EPS SMILES CACTVS 3.341 "O[CH]1[CH](CC(=C[CH]1O[P](O)(O)=O)C(O)=O)OC(=C)C(O)=O" EPS SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C=C(C(=O)O)O[C@@H]1CC(=C[C@H]([C@H]1O)OP(=O)(O)O)C(=O)O" EPS SMILES "OpenEye OEToolkits" 1.5.0 "C=C(C(=O)O)OC1CC(=CC(C1O)OP(=O)(O)O)C(=O)O" EPS InChI InChI 1.03 "InChI=1S/C10H13O10P/c1-4(9(12)13)19-6-2-5(10(14)15)3-7(8(6)11)20-21(16,17)18/h3,6-8,11H,1-2H2,(H,12,13)(H,14,15)(H2,16,17,18)/t6-,7-,8+/m1/s1" EPS InChIKey InChI 1.03 QUTYKIXIUDQOLK-PRJMDXOYSA-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 EPS "SYSTEMATIC NAME" ACDLabs 10.04 "(3R,4S,5R)-5-[(1-carboxyethenyl)oxy]-4-hydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid" EPS "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(3R,4S,5R)-4-hydroxy-5-(3-hydroxy-3-oxo-prop-1-en-2-yl)oxy-3-phosphonooxy-cyclohexene-1-carboxylic 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 EPS "Create component" 2003-09-15 RCSB EPS "Modify descriptor" 2011-06-04 RCSB EPS "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id EPS _pdbx_chem_comp_synonyms.name 5-ENOLPYRUVYLSHIKIMATE-3-PHOSPHATE _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##