data_4SR
# 
_chem_comp.id                                    4SR 
_chem_comp.name                                  (4S)-4-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]PYRROLIDIN-2-ONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C16 H21 N O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         (S)-ROLIPRAM 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-11-18 
_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                        275.343 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     4SR 
_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        1XN0 
_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 
4SR O15  O15  O 0 1 N N N 5.901  1.566  -9.889  -5.463 -1.273 0.956  O15  4SR 1  
4SR C14  C14  C 0 1 N N N 5.101  2.030  -9.090  -4.469 -0.976 0.328  C14  4SR 2  
4SR C16  C16  C 0 1 N N N 4.298  1.177  -8.165  -3.110 -0.701 0.935  C16  4SR 3  
4SR C11  C11  C 0 1 N N R 3.142  2.097  -7.742  -2.135 -0.792 -0.262 C11  4SR 4  
4SR C12  C12  C 0 1 N N N 3.725  3.514  -7.939  -3.066 -0.470 -1.452 C12  4SR 5  
4SR N13  N13  N 0 1 N N N 4.684  3.303  -9.009  -4.413 -0.845 -1.008 N13  4SR 6  
4SR C10  C10  C 0 1 Y N N 1.839  1.868  -8.535  -1.037 0.233  -0.142 C10  4SR 7  
4SR C17  C17  C 0 1 Y N N 0.640  1.741  -7.829  -1.355 1.571  -0.003 C17  4SR 8  
4SR C18  C18  C 0 1 Y N N -0.571 1.543  -8.491  -0.351 2.515  0.107  C18  4SR 9  
4SR C1   C1   C 0 1 Y N N -0.602 1.456  -9.886  0.977  2.121  0.079  C1   4SR 10 
4SR O19  O19  O 0 1 N N N -1.808 1.249  -10.546 1.965  3.048  0.188  O19  4SR 11 
4SR C20  C20  C 0 1 N N N -3.091 1.601  -9.988  1.326  4.320  0.316  C20  4SR 12 
4SR C2   C2   C 0 1 Y N N 0.595  1.574  -10.622 1.297  0.775  -0.067 C2   4SR 13 
4SR C9   C9   C 0 1 Y N N 1.814  1.778  -9.930  0.286  -0.167 -0.171 C9   4SR 14 
4SR O3   O3   O 0 1 N N N 0.556  1.478  -12.020 2.599  0.383  -0.095 O3   4SR 15 
4SR C4   C4   C 0 1 N N N 1.861  1.243  -12.640 2.603  -1.014 -0.395 C4   4SR 16 
4SR C5   C5   C 0 1 N N N 2.152  -0.241 -12.903 3.969  -1.425 -0.973 C5   4SR 17 
4SR C6   C6   C 0 1 N N N 1.473  -0.494 -14.273 4.556  -2.479 -0.011 C6   4SR 18 
4SR C7   C7   C 0 1 N N N 1.547  0.874  -14.983 3.316  -3.072 0.704  C7   4SR 19 
4SR C8   C8   C 0 1 N N N 1.465  1.867  -13.818 2.408  -1.833 0.898  C8   4SR 20 
4SR H161 1H16 H 0 0 N N N 4.877  0.743  -7.317  -2.867 -1.455 1.684  H161 4SR 21 
4SR H162 2H16 H 0 0 N N N 3.977  0.201  -8.598  -3.083 0.296  1.374  H162 4SR 22 
4SR H11  H11  H 0 1 N N N 2.816  1.903  -6.693  -1.721 -1.797 -0.352 H11  4SR 23 
4SR H121 1H12 H 0 0 N N N 4.142  3.984  -7.018  -3.027 0.595  -1.683 H121 4SR 24 
4SR H122 2H12 H 0 0 N N N 2.970  4.312  -8.133  -2.779 -1.056 -2.325 H122 4SR 25 
4SR H13  H13  H 0 1 N N N 5.041  4.002  -9.660  -5.167 -0.981 -1.603 H13  4SR 26 
4SR H17  H17  H 0 1 N N N 0.650  1.798  -6.727  -2.390 1.879  0.019  H17  4SR 27 
4SR H18  H18  H 0 1 N N N -1.505 1.455  -7.911  -0.602 3.560  0.216  H18  4SR 28 
4SR H201 1H20 H 0 0 N N N -3.046 2.680  -9.712  0.713  4.509  -0.565 H201 4SR 29 
4SR H202 2H20 H 0 0 N N N -4.058 1.435  -10.517 0.695  4.321  1.205  H202 4SR 30 
4SR H203 3H20 H 0 0 N N N -3.168 1.101  -8.994  2.083  5.099  0.407  H203 4SR 31 
4SR H9   H9   H 0 1 N N N 2.761  1.868  -10.488 0.531  -1.213 -0.280 H9   4SR 32 
4SR H4   H4   H 0 1 N N N 2.773  1.574  -12.090 1.811  -1.246 -1.107 H4   4SR 33 
4SR H51  1H5  H 0 1 N N N 1.827  -0.930 -12.089 3.840  -1.857 -1.966 H51  4SR 34 
4SR H52  2H5  H 0 1 N N N 3.231  -0.518 -12.861 4.628  -0.559 -1.025 H52  4SR 35 
4SR H61  1H6  H 0 1 N N N 0.445  -0.920 -14.204 5.081  -3.254 -0.569 H61  4SR 36 
4SR H62  2H6  H 0 1 N N N 1.913  -1.337 -14.855 5.223  -2.007 0.710  H62  4SR 37 
4SR H71  1H7  H 0 1 N N N 0.784  1.027  -15.781 2.827  -3.816 0.075  H71  4SR 38 
4SR H72  2H7  H 0 1 N N N 2.432  1.007  -15.648 3.595  -3.502 1.667  H72  4SR 39 
4SR H81  1H8  H 0 1 N N N 2.048  2.796  -14.017 2.728  -1.257 1.766  H81  4SR 40 
4SR H82  2H8  H 0 1 N N N 0.453  2.327  -13.729 1.366  -2.136 1.004  H82  4SR 41 
# 
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 
4SR O15 C14  DOUB N N 1  
4SR C14 C16  SING N N 2  
4SR C14 N13  SING N N 3  
4SR C16 C11  SING N N 4  
4SR C16 H161 SING N N 5  
4SR C16 H162 SING N N 6  
4SR C11 C12  SING N N 7  
4SR C11 C10  SING N N 8  
4SR C11 H11  SING N N 9  
4SR C12 N13  SING N N 10 
4SR C12 H121 SING N N 11 
4SR C12 H122 SING N N 12 
4SR N13 H13  SING N N 13 
4SR C10 C17  DOUB Y N 14 
4SR C10 C9   SING Y N 15 
4SR C17 C18  SING Y N 16 
4SR C17 H17  SING N N 17 
4SR C18 C1   DOUB Y N 18 
4SR C18 H18  SING N N 19 
4SR C1  O19  SING N N 20 
4SR C1  C2   SING Y N 21 
4SR O19 C20  SING N N 22 
4SR C20 H201 SING N N 23 
4SR C20 H202 SING N N 24 
4SR C20 H203 SING N N 25 
4SR C2  C9   DOUB Y N 26 
4SR C2  O3   SING N N 27 
4SR C9  H9   SING N N 28 
4SR O3  C4   SING N N 29 
4SR C4  C5   SING N N 30 
4SR C4  C8   SING N N 31 
4SR C4  H4   SING N N 32 
4SR C5  C6   SING N N 33 
4SR C5  H51  SING N N 34 
4SR C5  H52  SING N N 35 
4SR C6  C7   SING N N 36 
4SR C6  H61  SING N N 37 
4SR C6  H62  SING N N 38 
4SR C7  C8   SING N N 39 
4SR C7  H71  SING N N 40 
4SR C7  H72  SING N N 41 
4SR C8  H81  SING N N 42 
4SR C8  H82  SING N N 43 
# 
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 
4SR SMILES           ACDLabs              10.04 O=C3NCC(c2cc(OC1CCCC1)c(OC)cc2)C3                                                                                                     
4SR InChI            InChI                1.02b InChI=1/C16H21NO3/c1-19-14-7-6-11(12-9-16(18)17-10-12)8-15(14)20-13-4-2-3-5-13/h6-8,12-13H,2-5,9-10H2,1H3,(H,17,18)/t12-/m0/s1/f/h17H 
4SR InChIKey         InChI                1.02b HJORMJIFDVBMOB-ZIMDTWQLDD                                                                                                             
4SR SMILES_CANONICAL CACTVS               3.341 COc1ccc(cc1OC2CCCC2)[C@@H]3CNC(=O)C3                                                                                                  
4SR SMILES           CACTVS               3.341 COc1ccc(cc1OC2CCCC2)[CH]3CNC(=O)C3                                                                                                    
4SR SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 COc1ccc(cc1OC2CCCC2)[C@H]3CC(=O)NC3                                                                                                   
4SR SMILES           "OpenEye OEToolkits" 1.5.0 COc1ccc(cc1OC2CCCC2)C3CC(=O)NC3                                                                                                       
# 
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 
4SR "SYSTEMATIC NAME" ACDLabs              10.04 (4R)-4-[3-(cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one 
4SR "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (4R)-4-(3-cyclopentyloxy-4-methoxy-phenyl)pyrrolidin-2-one  
# 
