data_FPM
# 
_chem_comp.id                                    FPM 
_chem_comp.name                                  "(5R,6S)-6-(1-hydroxyethyl)-7-oxo-3-[(2R)-oxolan-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C12 H15 N O5 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         Faropenem 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-11-27 
_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                        285.316 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     FPM 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        3BFF 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBJ 
# 
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 
FPM C2   C2   C 0 1 N N N 27.352 20.857 19.622 -1.130 0.083  0.154  C2   FPM 1  
FPM C6   C6   C 0 1 N N S 28.155 19.177 22.733 2.335  0.545  -0.295 C6   FPM 2  
FPM C5   C5   C 0 1 N N R 27.368 20.484 22.298 1.343  0.705  0.864  C5   FPM 3  
FPM C7   C7   C 0 1 N N N 27.280 18.465 21.814 1.970  -0.925 -0.279 C7   FPM 4  
FPM N4   N4   N 0 1 N N N 26.540 19.583 21.469 1.023  -0.724 0.683  N4   FPM 5  
FPM C3   C3   C 0 1 N N N 26.553 19.845 20.013 -0.309 -0.957 0.362  C3   FPM 6  
FPM S1   S1   S 0 1 N N N 28.107 21.579 21.053 -0.197 1.564  0.418  S1   FPM 7  
FPM C31  C31  C 0 1 N N N 25.663 19.006 19.068 -0.795 -2.282 0.255  C31  FPM 8  
FPM O7   O7   O 0 1 N N N 27.260 17.266 21.529 2.364  -1.899 -0.885 O7   FPM 9  
FPM C61  C61  C 0 1 N N R 27.921 18.520 24.173 3.788  0.823  0.096  C61  FPM 10 
FPM O62  O62  O 0 1 N N N 28.524 17.220 24.480 3.913  2.178  0.532  O62  FPM 11 
FPM C62  C62  C 0 1 N N N 26.468 18.614 24.541 4.694  0.591  -1.115 C62  FPM 12 
FPM C14  C14  C 0 1 N N R 27.722 21.475 18.246 -2.583 0.004  -0.238 C14  FPM 13 
FPM C15  C15  C 0 1 N N N 27.096 22.834 18.012 -3.468 0.482  0.929  C15  FPM 14 
FPM C16  C16  C 0 1 N N N 28.048 23.528 17.026 -4.269 1.667  0.338  C16  FPM 15 
FPM C17  C17  C 0 1 N N N 29.410 22.907 17.346 -4.173 1.396  -1.185 C17  FPM 16 
FPM O18  O18  O 0 1 N N N 29.176 21.674 18.071 -2.835 0.876  -1.354 O18  FPM 17 
FPM O32  O32  O 0 1 N N N 24.957 18.144 19.592 0.059  -3.324 0.343  O32  FPM 18 
FPM O31  O31  O 0 1 N N N 25.565 19.287 17.836 -1.984 -2.482 0.083  O31  FPM 19 
FPM H6   H6   H 0 1 N N N 29.253 19.244 22.738 2.033  1.064  -1.205 H6   FPM 20 
FPM H5   H5   H 0 1 N N N 27.083 21.174 23.106 1.776  0.988  1.823  H5   FPM 21 
FPM H61  H61  H 0 1 N N N 28.536 19.141 24.841 4.081  0.152  0.903  H61  FPM 22 
FPM HO62 HO62 H 0 0 N N N 28.654 16.733 23.675 4.810  2.424  0.796  HO62 FPM 23 
FPM H162 H162 H 0 0 N N N 26.367 18.637 25.636 5.729  0.789  -0.836 H162 FPM 24 
FPM H262 H262 H 0 0 N N N 26.041 19.533 24.114 4.599  -0.443 -1.448 H262 FPM 25 
FPM H362 H362 H 0 0 N N N 25.932 17.740 24.142 4.401  1.261  -1.922 H362 FPM 26 
FPM H14  H14  H 0 1 N N N 27.334 20.735 17.531 -2.840 -1.021 -0.504 H14  FPM 27 
FPM H115 H115 H 0 0 N N N 27.013 23.401 18.951 -4.141 -0.314 1.247  H115 FPM 28 
FPM H215 H215 H 0 0 N N N 26.071 22.759 17.620 -2.851 0.814  1.764  H215 FPM 29 
FPM H116 H116 H 0 0 N N N 28.057 24.618 17.174 -5.306 1.642  0.673  H116 FPM 30 
FPM H216 H216 H 0 0 N N N 27.751 23.386 15.976 -3.802 2.618  0.595  H216 FPM 31 
FPM H117 H117 H 0 0 N N N 29.957 22.698 16.415 -4.912 0.656  -1.491 H117 FPM 32 
FPM H217 H217 H 0 0 N N N 30.014 23.599 17.952 -4.300 2.321  -1.748 H217 FPM 33 
FPM HO32 HO32 H 0 0 N N N 24.377 17.769 18.939 -0.365 -4.188 0.258  HO32 FPM 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 
FPM C16 C17  SING N N 1  
FPM C16 C15  SING N N 2  
FPM C17 O18  SING N N 3  
FPM O31 C31  DOUB N N 4  
FPM C15 C14  SING N N 5  
FPM O18 C14  SING N N 6  
FPM C14 C2   SING N N 7  
FPM C31 O32  SING N N 8  
FPM C31 C3   SING N N 9  
FPM C2  C3   DOUB N N 10 
FPM C2  S1   SING N N 11 
FPM C3  N4   SING N N 12 
FPM S1  C5   SING N N 13 
FPM N4  C7   SING N N 14 
FPM N4  C5   SING N N 15 
FPM O7  C7   DOUB N N 16 
FPM C7  C6   SING N N 17 
FPM C5  C6   SING N N 18 
FPM C6  C61  SING N N 19 
FPM C61 O62  SING N N 20 
FPM C61 C62  SING N N 21 
FPM C6  H6   SING N N 22 
FPM C5  H5   SING N N 23 
FPM C61 H61  SING N N 24 
FPM O62 HO62 SING N N 25 
FPM C62 H162 SING N N 26 
FPM C62 H262 SING N N 27 
FPM C62 H362 SING N N 28 
FPM C14 H14  SING N N 29 
FPM C15 H115 SING N N 30 
FPM C15 H215 SING N N 31 
FPM C16 H116 SING N N 32 
FPM C16 H216 SING N N 33 
FPM C17 H117 SING N N 34 
FPM C17 H217 SING N N 35 
FPM O32 HO32 SING N N 36 
# 
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 
FPM SMILES           ACDLabs              10.04 O=C2N1C(=C(SC1C2C(O)C)C3OCCC3)C(=O)O                                                                                                  
FPM 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)/t5-,6-,7+,11-/m1/s1/f/h16H 
FPM InChIKey         InChI                1.02b HGGAKXAHAYOLDJ-YWAGGUJQDR                                                                                                             
FPM SMILES_CANONICAL CACTVS               3.341 C[C@@H](O)[C@@H]1[C@H]2SC(=C(N2C1=O)C(O)=O)[C@H]3CCCO3                                                                                
FPM SMILES           CACTVS               3.341 C[CH](O)[CH]1[CH]2SC(=C(N2C1=O)C(O)=O)[CH]3CCCO3                                                                                      
FPM 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                                                                              
FPM 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 
FPM "SYSTEMATIC NAME" ACDLabs              10.04 "(5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)-tetrahydrofuran-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid" 
FPM "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-carboxylic acid"               
# 
