data_MER
# 
_chem_comp.id                                    MER 
_chem_comp.name                                  "(1R,5S,6S)-2-[(3S,5S)-5-DIMETHYLAMINOCARBONYLPYRROLIDIN-3-YLTHIO]-6-[(R)-1-HYDROXYETHYL]-1-METHYLCARBAPEN-2-EM-3-CARBOXYLIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C17 H27 N3 O6 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "MEROPENEM; MERREM; MERONEM" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-02-17 
_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                        401.478 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     MER 
_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        1H8Y 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
MER C7    C7    C 0 1 N N N 28.706 93.298 53.493 -0.596 0.415  4.988  C7    MER 1  
MER C2    C2    C 0 1 N N R 32.709 91.629 55.300 0.824  -0.641 0.719  C2    MER 2  
MER C6    C6    C 0 1 N N S 29.142 91.907 54.082 -1.230 0.216  3.635  C6    MER 3  
MER C5    C5    C 0 1 N N S 30.448 92.216 54.930 -0.352 -0.710 2.792  C5    MER 4  
MER C3    C3    C 0 1 N N N 32.621 92.751 54.539 1.719  -0.353 1.904  C3    MER 5  
MER O7    O7    O 0 1 N N N 29.187 93.630 52.407 -0.791 -0.388 5.869  O7    MER 6  
MER C61   C61   C 0 1 N N R 27.908 91.625 55.042 -2.615 -0.409 3.807  C61   MER 7  
MER O62   O62   O 0 1 N N N 28.230 90.980 56.184 -3.215 -0.597 2.524  O62   MER 8  
MER C62   C62   C 0 1 N N N 26.650 91.264 54.303 -3.493 0.518  4.650  C62   MER 9  
MER N4    N4    N 0 1 N N N 31.355 93.169 54.452 1.065  -0.395 2.996  N4    MER 10 
MER C31   C31   C 0 1 N N N 33.721 93.446 53.949 3.169  -0.058 1.806  C31   MER 11 
MER O31   O31   O 0 1 N N N 33.755 93.554 52.703 3.705  -0.004 0.718  O31   MER 12 
MER O32   O32   O 0 1 N N N 34.879 93.713 54.653 3.890  0.148  2.924  O32   MER 13 
MER S21   S21   S 0 1 N N N 34.040 90.407 54.936 1.133  0.545  -0.616 S21   MER 14 
MER C1A   C1A   C 0 1 N N S 35.692 91.143 55.240 0.144  -0.204 -1.939 C1A   MER 15 
MER C4A   C4A   C 0 1 N N N 35.744 92.040 56.492 0.269  0.612  -3.246 C4A   MER 16 
MER C5A   C5A   C 0 1 N N R 35.359 91.011 57.626 0.348  -0.441 -4.370 C5A   MER 17 
MER C1    C1    C 0 1 N N R 31.300 91.071 55.421 -0.607 -0.469 1.286  C1    MER 18 
MER N3A   N3A   N 0 1 N N N 35.629 89.721 56.990 0.237  -1.769 -3.729 N3A   MER 19 
MER C11   C11   C 0 1 N N N 31.363 89.930 54.331 -1.134 0.944  1.035  C11   MER 20 
MER C2A   C2A   C 0 1 N N N 36.525 89.929 55.830 0.718  -1.588 -2.335 C2A   MER 21 
MER C6A   C6A   C 0 1 N N N 36.241 91.282 58.905 -0.785 -0.243 -5.342 C6A   MER 22 
MER N7A   N7A   N 0 1 N N N 36.747 92.625 59.149 -0.702 0.711  -6.289 N7A   MER 23 
MER O6A   O6A   O 0 1 N N N 37.077 90.376 59.130 -1.773 -0.943 -5.271 O6A   MER 24 
MER C8A   C8A   C 0 1 N N N 38.068 93.024 58.719 0.529  1.488  -6.440 C8A   MER 25 
MER C9A   C9A   C 0 1 N N N 36.181 93.304 60.279 -1.845 0.971  -7.169 C9A   MER 26 
MER O71   O71   O 0 1 N Y N 28.280 94.460 54.245 0.183  1.483  5.214  O71   MER 27 
MER HC2   2HC   H 0 1 N N N 32.948 92.004 56.322 0.974  -1.661 0.365  HC2   MER 28 
MER HC6   6HC   H 0 1 N N N 29.291 91.121 53.305 -1.326 1.180  3.134  HC6   MER 29 
MER HC5   5HC   H 0 1 N N N 29.851 92.634 55.774 -0.548 -1.752 3.047  HC5   MER 30 
MER HC16  6HC1  H 0 0 N N N 27.669 92.648 55.416 -2.519 -1.372 4.308  HC16  MER 31 
MER HO26  6HO2  H 0 0 N N N 27.492 90.811 56.758 -3.282 0.276  2.116  HO26  MER 32 
MER H621  1H62  H 0 0 N N N 25.784 91.066 54.977 -4.480 0.072  4.772  H621  MER 33 
MER H622  2H62  H 0 0 N N N 26.826 90.400 53.620 -3.035 0.661  5.628  H622  MER 34 
MER H623  3H62  H 0 0 N N N 26.395 92.046 53.550 -3.589 1.481  4.149  H623  MER 35 
MER HO23  3HO2  H 0 0 N N N 35.610 94.175 54.260 4.836  0.340  2.860  HO23  MER 36 
MER HCA1  1HCA  H 0 0 N N N 36.151 91.606 54.336 -0.899 -0.291 -1.637 HCA1  MER 37 
MER H4A1  1H4A  H 0 0 N N N 35.114 92.959 56.447 -0.605 1.248  -3.385 H4A1  MER 38 
MER H4A2  2H4A  H 0 0 N N N 36.704 92.586 56.649 1.177  1.215  -3.227 H4A2  MER 39 
MER HCA5  5HCA  H 0 0 N N N 34.276 91.099 57.877 1.302  -0.359 -4.891 HCA5  MER 40 
MER HC1   1HC   H 0 1 N N N 31.037 90.712 56.443 -1.285 -1.217 0.875  HC1   MER 41 
MER HNA3  3HNA  H 0 0 N N N 36.000 89.035 57.648 0.903  -2.370 -4.189 HNA3  MER 42 
MER H111  1H11  H 0 0 N N N 30.330 89.521 54.420 -1.268 1.097  -0.035 H111  MER 43 
MER H112  2H11  H 0 0 N N N 32.190 89.191 54.447 -2.090 1.071  1.543  H112  MER 44 
MER H113  3H11  H 0 0 N N N 31.673 90.250 53.309 -0.419 1.671  1.419  H113  MER 45 
MER H2A1  1H2A  H 0 0 N N N 37.611 90.086 56.028 1.807  -1.576 -2.302 H2A1  MER 46 
MER H2A2  2H2A  H 0 0 N N N 36.728 89.059 55.162 0.321  -2.369 -1.686 H2A2  MER 47 
MER H8A1  1H8A  H 0 0 N N N 38.456 94.053 58.906 0.409  2.206  -7.251 H8A1  MER 48 
MER H8A2  2H8A  H 0 0 N N N 38.149 92.820 57.626 0.740  2.019  -5.512 H8A2  MER 49 
MER H8A3  3H8A  H 0 0 N N N 38.801 92.299 59.144 1.357  0.816  -6.669 H8A3  MER 50 
MER H9A1  1H9A  H 0 0 N N N 36.569 94.333 60.466 -2.693 0.364  -6.852 H9A1  MER 51 
MER H9A2  2H9A  H 0 0 N N N 36.297 92.680 61.196 -2.112 2.026  -7.114 H9A2  MER 52 
MER H9A3  3H9A  H 0 0 N N N 35.069 93.325 60.194 -1.579 0.717  -8.195 H9A3  MER 53 
MER "HO'" "HO'" H 0 1 N N N 28.016 95.300 53.889 0.647  1.573  6.057  "HO'" MER 54 
# 
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 
MER C7  C6    SING N N 1  
MER C7  O7    DOUB N N 2  
MER C7  O71   SING N N 3  
MER C2  C3    SING N N 4  
MER C2  S21   SING N N 5  
MER C2  C1    SING N N 6  
MER C2  HC2   SING N N 7  
MER C6  C5    SING N N 8  
MER C6  C61   SING N N 9  
MER C6  HC6   SING N N 10 
MER C5  N4    SING N N 11 
MER C5  C1    SING N N 12 
MER C5  HC5   SING N N 13 
MER C3  N4    DOUB N N 14 
MER C3  C31   SING N N 15 
MER C61 O62   SING N N 16 
MER C61 C62   SING N N 17 
MER C61 HC16  SING N N 18 
MER O62 HO26  SING N N 19 
MER C62 H621  SING N N 20 
MER C62 H622  SING N N 21 
MER C62 H623  SING N N 22 
MER C31 O31   DOUB N N 23 
MER C31 O32   SING N N 24 
MER O32 HO23  SING N N 25 
MER S21 C1A   SING N N 26 
MER C1A C4A   SING N N 27 
MER C1A C2A   SING N N 28 
MER C1A HCA1  SING N N 29 
MER C4A C5A   SING N N 30 
MER C4A H4A1  SING N N 31 
MER C4A H4A2  SING N N 32 
MER C5A N3A   SING N N 33 
MER C5A C6A   SING N N 34 
MER C5A HCA5  SING N N 35 
MER C1  C11   SING N N 36 
MER C1  HC1   SING N N 37 
MER N3A C2A   SING N N 38 
MER N3A HNA3  SING N N 39 
MER C11 H111  SING N N 40 
MER C11 H112  SING N N 41 
MER C11 H113  SING N N 42 
MER C2A H2A1  SING N N 43 
MER C2A H2A2  SING N N 44 
MER C6A N7A   SING N N 45 
MER C6A O6A   DOUB N N 46 
MER N7A C8A   SING N N 47 
MER N7A C9A   SING N N 48 
MER C8A H8A1  SING N N 49 
MER C8A H8A2  SING N N 50 
MER C8A H8A3  SING N N 51 
MER C9A H9A1  SING N N 52 
MER C9A H9A2  SING N N 53 
MER C9A H9A3  SING N N 54 
MER O71 "HO'" SING N N 55 
# 
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 
MER SMILES           ACDLabs              10.04 O=C(O)C(C2N=C(C(=O)O)C(SC1CC(C(=O)N(C)C)NC1)C2C)C(O)C                                                                                                                                     
MER InChI            InChI                1.02b InChI=1/C17H27N3O6S/c1-7-12(11(8(2)21)16(23)24)19-13(17(25)26)14(7)27-9-5-10(18-6-9)15(22)20(3)4/h7-12,14,18,21H,5-6H2,1-4H3,(H,23,24)(H,25,26)/t7-,8-,9+,10-,11-,12-,14-/m1/s1/f/h23,25H 
MER InChIKey         InChI                1.02b CDYPSIIDXKMBLV-KEBREYARDA                                                                                                                                                                 
MER SMILES_CANONICAL CACTVS               3.341 C[C@@H](O)[C@H]([C@@H]1N=C([C@H](S[C@@H]2CN[C@H](C2)C(=O)N(C)C)[C@@H]1C)C(O)=O)C(O)=O                                                                                                     
MER SMILES           CACTVS               3.341 C[CH](O)[CH]([CH]1N=C([CH](S[CH]2CN[CH](C2)C(=O)N(C)C)[CH]1C)C(O)=O)C(O)=O                                                                                                                
MER SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@H]1[C@H](C(=N[C@H]1[C@@H]([C@@H](C)O)C(=O)O)C(=O)O)S[C@H]2C[C@@H](NC2)C(=O)N(C)C                                                                                                      
MER SMILES           "OpenEye OEToolkits" 1.5.0 CC1C(C(=NC1C(C(C)O)C(=O)O)C(=O)O)SC2CC(NC2)C(=O)N(C)C                                                                                                                                     
# 
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 
MER "SYSTEMATIC NAME" ACDLabs              10.04 "(2S,3R,4R)-2-[(1S,2R)-1-carboxy-2-hydroxypropyl]-4-{[(3S,5R)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl}-3-methyl-3,4-dihydro-2H-pyrrole-5-carboxylic acid"    
MER "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(3R,4R,5S)-5-[(2S,3R)-1,3-dihydroxy-1-oxo-butan-2-yl]-3-[(3S,5R)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-4-methyl-4,5-dihydro-3H-pyrrole-2-carboxylic acid" 
# 
