data_FRO
# 
_chem_comp.id                                    FRO 
_chem_comp.name                                  (5R,6S)-6-[(1R)-1-HYDROXYETHYL]-7-OXO-3-[(2R)-TETRAHYDROFURAN-2-YL]-4-THIA-1-AZABICYCLO[3.2.0]HEPT-2-ENE-2-CARBOXYLATE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C12 H14 N O5 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         FAROM 
_chem_comp.pdbx_formal_charge                    -1 
_chem_comp.pdbx_initial_date                     2005-11-15 
_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                        284.308 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     FRO 
_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        2EXA 
_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 
FRO C8   C8   C 0  1 N N N 90.950 -2.719 40.927 -3.542 -0.210 -0.975 C8   FRO 1  
FRO C9   C9   C 0  1 N N N 92.466 -2.886 41.176 -4.465 -1.333 -0.443 C9   FRO 2  
FRO C10  C10  C 0  1 N N N 92.576 -3.606 42.540 -4.371 -1.131 1.091  C10  FRO 3  
FRO O11  O11  O 0  1 N N N 91.284 -3.389 43.159 -2.992 -0.750 1.299  O11  FRO 4  
FRO C7   C7   C 0  1 N N R 90.311 -3.544 42.060 -2.636 0.134  0.223  C7   FRO 5  
FRO C5   C5   C 0  1 N N N 88.896 -3.048 42.455 -1.191 -0.070 -0.151 C5   FRO 6  
FRO S6   S6   S 0  1 N N N 88.777 -2.204 43.953 -0.349 -1.606 -0.492 S6   FRO 7  
FRO C4   C4   C 0  1 N N N 87.731 -3.859 42.412 -0.229 0.869  -0.308 C4   FRO 8  
FRO C12  C12  C 0  1 N N N 87.437 -4.872 41.262 -0.563 2.232  -0.148 C12  FRO 9  
FRO O13  O13  O -1 1 N N N 88.082 -5.954 41.225 0.357  3.125  -0.178 O13  FRO 10 
FRO O14  O14  O 0  1 N N N 86.365 -4.691 40.634 -1.785 2.577  0.027  O14  FRO 11 
FRO N3   N3   N 0  1 N N N 86.652 -3.189 42.882 1.096  0.526  -0.635 N3   FRO 12 
FRO C2   C2   C 0  1 N N R 86.965 -2.341 44.036 1.305  -0.923 -0.881 C2   FRO 13 
FRO C1   C1   C 0  1 N N S 86.645 -3.017 45.347 2.262  -0.901 0.315  C1   FRO 14 
FRO C15  C15  C 0  1 N N N 85.180 -3.479 45.335 2.037  0.595  0.356  C15  FRO 15 
FRO O16  O16  O 0  1 N N N 84.838 -4.627 45.594 2.493  1.500  1.023  O16  FRO 16 
FRO C17  C17  C 0  1 N N S 86.910 -1.903 46.404 3.696  -1.299 -0.038 C17  FRO 17 
FRO C18  C18  C 0  1 N N N 88.375 -1.498 46.382 4.547  -1.322 1.234  C18  FRO 18 
FRO O19  O19  O 0  1 N N N 86.550 -2.317 47.694 4.241  -0.350 -0.957 O19  FRO 19 
FRO H81  1H8  H 0  1 N N N 90.629 -1.667 40.931 -4.129 0.659  -1.271 H81  FRO 20 
FRO H82  2H8  H 0  1 N N N 90.659 -3.098 39.936 -2.945 -0.572 -1.813 H82  FRO 21 
FRO H91  1H9  H 0  1 N N N 92.989 -1.918 41.181 -5.488 -1.194 -0.792 H91  FRO 22 
FRO H92  2H9  H 0  1 N N N 92.932 -3.483 40.378 -4.088 -2.315 -0.730 H92  FRO 23 
FRO H101 1H10 H 0  0 N N N 93.405 -3.221 43.152 -5.040 -0.334 1.415  H101 FRO 24 
FRO H102 2H10 H 0  0 N N N 92.782 -4.679 42.410 -4.596 -2.060 1.615  H102 FRO 25 
FRO H7   H7   H 0  1 N N N 90.135 -4.591 41.772 -2.798 1.169  0.525  H7   FRO 26 
FRO H2   H2   H 0  1 N N N 86.399 -1.398 44.001 1.726  -1.220 -1.842 H2   FRO 27 
FRO H1   H1   H 0  1 N N N 87.242 -3.917 45.554 1.879  -1.426 1.191  H1   FRO 28 
FRO H17  H17  H 0  1 N N N 86.285 -1.037 46.139 3.697  -2.289 -0.494 H17  FRO 29 
FRO H181 1H18 H 0  0 N N N 88.975 -2.266 46.891 4.545  -0.333 1.690  H181 FRO 30 
FRO H182 2H18 H 0  0 N N N 88.497 -0.535 46.899 4.131  -2.046 1.935  H182 FRO 31 
FRO H183 3H18 H 0  0 N N N 88.713 -1.400 45.340 5.569  -1.605 0.983  H183 FRO 32 
FRO H19  H19  H 0  1 N N N 86.469 -3.263 47.712 4.222  0.510  -0.515 H19  FRO 33 
# 
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 
FRO C8  C9   SING N N 1  
FRO C8  C7   SING N N 2  
FRO C8  H81  SING N N 3  
FRO C8  H82  SING N N 4  
FRO C9  C10  SING N N 5  
FRO C9  H91  SING N N 6  
FRO C9  H92  SING N N 7  
FRO C10 O11  SING N N 8  
FRO C10 H101 SING N N 9  
FRO C10 H102 SING N N 10 
FRO O11 C7   SING N N 11 
FRO C7  C5   SING N N 12 
FRO C7  H7   SING N N 13 
FRO C5  S6   SING N N 14 
FRO C5  C4   DOUB N N 15 
FRO S6  C2   SING N N 16 
FRO C4  C12  SING N N 17 
FRO C4  N3   SING N N 18 
FRO C12 O13  SING N N 19 
FRO C12 O14  DOUB N N 20 
FRO N3  C2   SING N N 21 
FRO N3  C15  SING N N 22 
FRO C2  C1   SING N N 23 
FRO C2  H2   SING N N 24 
FRO C1  C15  SING N N 25 
FRO C1  C17  SING N N 26 
FRO C1  H1   SING N N 27 
FRO C15 O16  DOUB N N 28 
FRO C17 C18  SING N N 29 
FRO C17 O19  SING N N 30 
FRO C17 H17  SING N N 31 
FRO C18 H181 SING N N 32 
FRO C18 H182 SING N N 33 
FRO C18 H183 SING N N 34 
FRO O19 H19  SING N N 35 
# 
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 
FRO SMILES           ACDLabs              10.04 O=C2N1C(=C(SC1C2C(O)C)C3OCCC3)C([O-])=O                                                                                                            
FRO InChI            InChI                1.02b InChI=1/C12H15NO5S/c1-5(14)7-10(15)13-8(12(16)17)9(19-11(7)13)6-3-2-4-18-6/h5-7,11,14H,2-4H2,1H3,(H,16,17)/p-1/t5-,6+,7-,11+/m0/s1/fC12H14NO5S/q-1 
FRO InChIKey         InChI                1.02b HGGAKXAHAYOLDJ-UHQKRICFDP                                                                                                                          
FRO SMILES_CANONICAL CACTVS               3.341 C[C@H](O)[C@@H]1[C@H]2SC(=C(N2C1=O)C([O-])=O)[C@H]3CCCO3                                                                                           
FRO SMILES           CACTVS               3.341 C[CH](O)[CH]1[CH]2SC(=C(N2C1=O)C([O-])=O)[CH]3CCCO3                                                                                                
FRO SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@@H]([C@@H]1[C@@H]2N(C1=O)C(=C(S2)[C@H]3CCCO3)C(=O)[O-])O                                                                                       
FRO SMILES           "OpenEye OEToolkits" 1.5.0 CC(C1C2N(C1=O)C(=C(S2)C3CCCO3)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 
FRO "SYSTEMATIC NAME" ACDLabs              10.04 (5R,6S)-6-[(1S)-1-hydroxyethyl]-7-oxo-3-[(2R)-tetrahydrofuran-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 
FRO "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (5R,6S)-6-(1-hydroxyethyl)-7-oxo-3-[(2R)-oxolan-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate               
# 
