data_BAR
# 
_chem_comp.id                                    BAR 
_chem_comp.name                                  "8-HYDROXY-2-OXA-BICYCLO[3.3.1]NON-6-ENE-3,5-DICARBOXYLIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C10 H12 O6" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   N 
_chem_comp.pdbx_release_status                   OBS 
_chem_comp.pdbx_replaced_by                      TSA 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        228.199 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     BAR 
_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        4CSM 
_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 
BAR "C'" "C'" C 0 1 N N N 39.605 24.971 -10.489 0.058  -1.311 0.882  "C'" BAR 1  
BAR C1   C1   C 0 1 N N N 38.350 25.032 -9.974  -0.327 -1.087 -0.332 C1   BAR 2  
BAR C2   C2   C 0 1 N N S 37.596 23.801 -9.513  0.083  0.140  -1.107 C2   BAR 3  
BAR C3   C3   C 0 1 N N N 38.586 22.683 -9.170  1.421  0.645  -0.541 C3   BAR 4  
BAR C4   C4   C 0 1 N N R 40.315 23.678 -10.848 0.973  -0.423 1.669  C4   BAR 5  
BAR C5   C5   C 0 1 N N R 39.427 22.487 -10.452 1.228  0.894  0.952  C5   BAR 6  
BAR C6   C6   C 0 1 N N N 36.690 23.372 -10.654 -0.966 1.230  -0.808 C6   BAR 7  
BAR C7   C7   C 0 1 N N S 37.461 22.901 -11.893 -1.036 1.359  0.718  C7   BAR 8  
BAR C8   C8   C 0 1 N N N 36.775 24.174 -8.278  0.189  -0.153 -2.581 C8   BAR 9  
BAR C9   C9   C 0 1 N N N 37.863 23.981 -12.908 -1.339 0.027  1.355  C9   BAR 10 
BAR O1   O1   O 0 1 N N N 41.574 23.725 -10.222 2.218  -1.094 1.867  O1   BAR 11 
BAR O2   O2   O 0 1 N N N 38.968 23.941 -13.452 -0.975 -0.198 2.484  O2   BAR 12 
BAR O3   O3   O 0 1 N N N 37.069 24.873 -13.159 -2.015 -0.906 0.667  O3   BAR 13 
BAR O4   O4   O 0 1 N N N 36.299 25.323 -8.287  1.242  0.001  -3.153 O4   BAR 14 
BAR O5   O5   O 0 1 N N N 36.614 23.353 -7.342  -0.885 -0.588 -3.258 O5   BAR 15 
BAR "O'" "O'" O 0 1 N N N 38.597 22.134 -11.542 0.210  1.841  1.203  "O'" BAR 16 
BAR "H'" "H'" H 0 1 N N N 40.048 25.973 -10.615 -0.305 -2.206 1.364  "H'" BAR 17 
BAR H1   H1   H 0 1 N N N 37.951 26.059 -9.931  -0.971 -1.810 -0.811 H1   BAR 18 
BAR H31  1H3  H 0 1 N N N 39.194 22.882 -8.256  2.194  -0.107 -0.693 H31  BAR 19 
BAR H32  2H3  H 0 1 N N N 38.102 21.749 -8.799  1.706  1.573  -1.037 H32  BAR 20 
BAR H4   H4   H 0 1 N N N 40.490 23.549 -11.941 0.521  -0.218 2.639  H4   BAR 21 
BAR H5   H5   H 0 1 N N N 40.129 21.658 -10.199 2.161  1.302  1.340  H5   BAR 22 
BAR H61  1H6  H 0 1 N N N 35.968 22.592 -10.315 -0.691 2.189  -1.248 H61  BAR 23 
BAR H62  2H6  H 0 1 N N N 35.972 24.183 -10.917 -1.931 0.905  -1.197 H62  BAR 24 
BAR H7   H7   H 0 1 N N N 36.707 22.272 -12.422 -1.823 2.069  0.972  H7   BAR 25 
BAR HO1  HO1  H 0 1 N N N 42.018 22.915 -10.446 2.021  -1.916 2.338  HO1  BAR 26 
BAR HO3  HO3  H 0 1 N N N 37.317 25.541 -13.786 -2.209 -1.761 1.076  HO3  BAR 27 
BAR HO5  HO5  H 0 1 N N N 36.104 23.584 -6.574  -0.816 -0.777 -4.204 HO5  BAR 28 
# 
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 
BAR "C'" C1   DOUB N N 1  
BAR "C'" C4   SING N N 2  
BAR "C'" "H'" SING N N 3  
BAR C1   C2   SING N N 4  
BAR C1   H1   SING N N 5  
BAR C2   C3   SING N N 6  
BAR C2   C6   SING N N 7  
BAR C2   C8   SING N N 8  
BAR C3   C5   SING N N 9  
BAR C3   H31  SING N N 10 
BAR C3   H32  SING N N 11 
BAR C4   C5   SING N N 12 
BAR C4   O1   SING N N 13 
BAR C4   H4   SING N N 14 
BAR C5   "O'" SING N N 15 
BAR C5   H5   SING N N 16 
BAR C6   C7   SING N N 17 
BAR C6   H61  SING N N 18 
BAR C6   H62  SING N N 19 
BAR C7   C9   SING N N 20 
BAR C7   "O'" SING N N 21 
BAR C7   H7   SING N N 22 
BAR C8   O4   DOUB N N 23 
BAR C8   O5   SING N N 24 
BAR C9   O2   DOUB N N 25 
BAR C9   O3   SING N N 26 
BAR O1   HO1  SING N N 27 
BAR O3   HO3  SING N N 28 
BAR O5   HO5  SING N N 29 
# 
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 
BAR SMILES           ACDLabs              10.04 O=C(O)C1OC2C(O)C=CC(C(=O)O)(C1)C2                                                                                                 
BAR InChI            InChI                1.02b InChI=1/C10H12O6/c11-5-1-2-10(9(14)15)3-6(5)16-7(4-10)8(12)13/h1-2,5-7,11H,3-4H2,(H,12,13)(H,14,15)/t5-,6-,7+,10+/m1/s1/f/h12,14H 
BAR InChIKey         InChI                1.02b KRZHNRULRHECRF-PUPABIEADP                                                                                                         
BAR SMILES_CANONICAL CACTVS               3.341 O[C@@H]1C=C[C@@]2(C[C@H]1O[C@@H](C2)C(O)=O)C(O)=O                                                                                 
BAR SMILES           CACTVS               3.341 O[CH]1C=C[C]2(C[CH]1O[CH](C2)C(O)=O)C(O)=O                                                                                        
BAR SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C1[C@@H]2[C@@H](C=C[C@]1(C[C@H](O2)C(=O)O)C(=O)O)O                                                                                
BAR SMILES           "OpenEye OEToolkits" 1.5.0 C1C2C(C=CC1(CC(O2)C(=O)O)C(=O)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 
BAR "SYSTEMATIC NAME" ACDLabs              10.04 "(1R,3S,5S,8R)-8-hydroxy-2-oxabicyclo[3.3.1]non-6-ene-3,5-dicarboxylic acid" 
BAR "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(1S,3S,5R,6R)-6-hydroxy-4-oxabicyclo[3.3.1]non-7-ene-1,3-dicarboxylic acid" 
# 
