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                    2008-10-14 
_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 InChI            InChI                1.02b InChI=1/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/f/h12,14,16-17H 
EPS InChIKey         InChI                1.02b QUTYKIXIUDQOLK-HDIBZSGADS                                                                                                                                    
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                                                                                                                   
# 
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" 
# 
