data_4RR
# 
_chem_comp.id                                    4RR 
_chem_comp.name                                  (4R)-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                         (R)-ROLIPRAM 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-11-17 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   OBS 
_chem_comp.pdbx_replaced_by                      ROL 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        275.343 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     4RR 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "OpenEye/OEToolkits V1.4.2" 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1XMY 
_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 
4RR O3   O3   O 0 1 N N N 40.879 6.269  0.900  6.584  -3.773 8.309 O3   4RR 1  
4RR C2   C2   C 0 1 N N N 41.608 5.403  1.367  6.536  -2.737 7.663 C2   4RR 2  
4RR C1   C1   C 0 1 N N N 42.426 4.528  0.482  5.348  -2.259 6.865 C1   4RR 3  
4RR N4   N4   N 0 1 N N N 41.763 5.050  2.654  7.552  -1.810 7.479 N4   4RR 4  
4RR C5   C5   C 0 1 N N N 42.686 3.926  2.808  7.167  -0.735 6.609 C5   4RR 5  
4RR C6   C6   C 0 1 N N R 42.987 3.450  1.429  5.638  -0.760 6.652 C6   4RR 6  
4RR C7   C7   C 0 1 Y N N 42.229 2.087  1.308  4.934  -0.115 5.479 C7   4RR 7  
4RR C8   C8   C 0 1 Y N N 40.836 2.030  1.129  3.689  -0.590 5.065 C8   4RR 8  
4RR C9   C9   C 0 1 Y N N 40.183 0.798  1.028  3.047  0.008  3.986 C9   4RR 9  
4RR C16  C16  C 0 1 Y N N 40.942 -0.375 1.103  3.635  1.076  3.316 C16  4RR 10 
4RR C19  C19  C 0 1 Y N N 42.318 -0.334 1.283  4.880  1.551  3.730 C19  4RR 11 
4RR C20  C20  C 0 1 Y N N 42.931 0.877  1.418  5.529  0.956  4.811 C20  4RR 12 
4RR O17  O17  O 0 1 N N N 40.211 -1.560 1.026  3.011  1.666  2.259 O17  4RR 13 
4RR C18  C18  C 0 1 N N N 40.729 -2.902 1.009  3.687  2.754  1.631 C18  4RR 14 
4RR O10  O10  O 0 1 N N N 38.780 0.661  0.825  1.825  -0.467 3.588 O10  4RR 15 
4RR C11  C11  C 0 1 N N N 38.052 1.878  0.620  1.770  -1.828 3.178 C11  4RR 16 
4RR C12  C12  C 0 1 N N N 36.690 1.116  0.558  1.217  -1.908 1.763 C12  4RR 17 
4RR C13  C13  C 0 1 N N N 36.232 1.257  -0.925 -0.295 -1.772 1.935 C13  4RR 18 
4RR C14  C14  C 0 1 N N N 36.920 2.545  -1.459 -0.601 -2.178 3.377 C14  4RR 19 
4RR C15  C15  C 0 1 N N N 38.314 2.526  -0.754 0.734  -2.586 3.994 C15  4RR 20 
4RR H181 1H18 H 0 0 N N N 40.861 -3.231 -0.032 3.814  3.567  2.350 H181 4RR 21 
4RR H182 2H18 H 0 0 N N N 41.699 -2.927 1.527  3.105  3.099  0.773 H182 4RR 22 
4RR H183 3H18 H 0 0 N N N 40.023 -3.574 1.519  4.668  2.414  1.291 H183 4RR 23 
4RR H19  H19  H 0 1 N N N 42.894 -1.247 1.316  5.349  2.385  3.214 H19  4RR 24 
4RR H20  H20  H 0 1 N N N 43.992 0.906  1.616  6.498  1.332  5.127 H20  4RR 25 
4RR H8   H8   H 0 1 N N N 40.266 2.945  1.069  3.223  -1.424 5.583 H8   4RR 26 
4RR H11  H11  H 0 1 N N N 38.226 2.702  1.328  2.772  -2.257 3.265 H11  4RR 27 
4RR H151 1H15 H 0 0 N N N 38.714 3.545  -0.641 0.767  -2.339 5.060 H151 4RR 28 
4RR H152 2H15 H 0 0 N N N 39.064 1.971  -1.336 0.877  -3.666 3.878 H152 4RR 29 
4RR H141 1H14 H 0 0 N N N 37.020 2.526  -2.554 -1.027 -1.324 3.918 H141 4RR 30 
4RR H142 2H14 H 0 0 N N N 36.345 3.458  -1.245 -1.330 -2.993 3.426 H142 4RR 31 
4RR H131 1H13 H 0 0 N N N 36.539 0.379  -1.512 -0.832 -2.398 1.214 H131 4RR 32 
4RR H132 2H13 H 0 0 N N N 35.137 1.322  -1.005 -0.610 -0.736 1.765 H132 4RR 33 
4RR H121 1H12 H 0 0 N N N 36.813 0.059  0.837  1.447  -2.886 1.325 H121 4RR 34 
4RR H122 2H12 H 0 0 N N N 35.951 1.526  1.263  1.612  -1.128 1.105 H122 4RR 35 
4RR H6   H6   H 0 1 N N N 44.051 3.300  1.192  5.308  -0.221 7.550 H6   4RR 36 
4RR H51  1H5  H 0 1 N N N 43.607 4.247  3.317  7.564  -0.942 5.610 H51  4RR 37 
4RR H52  2H5  H 0 1 N N N 42.246 3.126  3.421  7.583  0.208  6.976 H52  4RR 38 
4RR HN4  HN4  H 0 1 N N N 41.301 5.503  3.417  8.481  -1.912 7.875 HN4  4RR 39 
4RR H11A 1H1  H 0 0 N N N 41.812 4.080  -0.313 5.310  -2.810 5.919 H11A 4RR 40 
4RR H12  2H1  H 0 1 N N N 43.221 5.084  -0.038 4.419  -2.413 7.420 H12  4RR 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 
4RR O3  C2   DOUB N N 1  
4RR C2  N4   SING N N 2  
4RR C2  C1   SING N N 3  
4RR C1  C6   SING N N 4  
4RR C1  H11A SING N N 5  
4RR C1  H12  SING N N 6  
4RR N4  C5   SING N N 7  
4RR N4  HN4  SING N N 8  
4RR C5  C6   SING N N 9  
4RR C5  H51  SING N N 10 
4RR C5  H52  SING N N 11 
4RR C6  C7   SING N N 12 
4RR C6  H6   SING N N 13 
4RR C7  C20  SING Y N 14 
4RR C7  C8   DOUB Y N 15 
4RR C8  C9   SING Y N 16 
4RR C8  H8   SING N N 17 
4RR C9  C16  DOUB Y N 18 
4RR C9  O10  SING N N 19 
4RR C16 O17  SING N N 20 
4RR C16 C19  SING Y N 21 
4RR C19 C20  DOUB Y N 22 
4RR C19 H19  SING N N 23 
4RR C20 H20  SING N N 24 
4RR O17 C18  SING N N 25 
4RR C18 H181 SING N N 26 
4RR C18 H182 SING N N 27 
4RR C18 H183 SING N N 28 
4RR O10 C11  SING N N 29 
4RR C11 C15  SING N N 30 
4RR C11 C12  SING N N 31 
4RR C11 H11  SING N N 32 
4RR C12 C13  SING N N 33 
4RR C12 H121 SING N N 34 
4RR C12 H122 SING N N 35 
4RR C13 C14  SING N N 36 
4RR C13 H131 SING N N 37 
4RR C13 H132 SING N N 38 
4RR C14 C15  SING N N 39 
4RR C14 H141 SING N N 40 
4RR C14 H142 SING N N 41 
4RR C15 H151 SING N N 42 
4RR C15 H152 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 
4RR SMILES           ACDLabs              10.04 O=C3NCC(c2cc(OC1CCCC1)c(OC)cc2)C3                                                                                                     
4RR 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 
4RR InChIKey         InChI                1.02b HJORMJIFDVBMOB-ZIMDTWQLDD                                                                                                             
4RR SMILES_CANONICAL CACTVS               3.341 COc1ccc(cc1OC2CCCC2)[C@@H]3CNC(=O)C3                                                                                                  
4RR SMILES           CACTVS               3.341 COc1ccc(cc1OC2CCCC2)[CH]3CNC(=O)C3                                                                                                    
4RR SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 COc1ccc(cc1OC2CCCC2)[C@H]3CC(=O)NC3                                                                                                   
4RR 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 
4RR "SYSTEMATIC NAME" ACDLabs              10.04 (4R)-4-[3-(cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one 
4RR "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (4R)-4-(3-cyclopentyloxy-4-methoxy-phenyl)pyrrolidin-2-one  
# 
