data_PFI
# 
_chem_comp.id                                    PFI 
_chem_comp.name                                  (6S)-6-CYCLOPENTYL-6-[2-(3-FLUORO-4-ISOPROPOXYPHENYL)ETHYL]-4-HYDROXY-5,6-DIHYDRO-2H-PYRAN-2-ONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H27 F O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-06-14 
_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                        362.435 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     PFI 
_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        2HAI 
_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 
PFI F26  F26  F 0 1 N N N 39.111 11.586 60.642 3.953  -1.207 -2.388 F26  PFI 1  
PFI C23  C23  C 0 1 Y N N 40.265 11.905 60.046 3.369  -0.892 -1.211 C23  PFI 2  
PFI C22  C22  C 0 1 Y N N 41.480 11.384 60.574 4.123  -0.325 -0.191 C22  PFI 3  
PFI O24  O24  O 0 1 N N N 41.439 10.591 61.678 5.447  -0.082 -0.377 O24  PFI 4  
PFI C25  C25  C 0 1 N N N 42.030 11.053 62.899 5.961  0.383  0.873  C25  PFI 5  
PFI C2   C2   C 0 1 N N N 41.262 12.294 63.431 7.471  0.141  0.926  C2   PFI 6  
PFI C1   C1   C 0 1 N N N 42.001 9.916  63.906 5.679  1.880  1.015  C1   PFI 7  
PFI C21  C21  C 0 1 Y N N 42.710 11.724 59.948 3.520  -0.002 1.015  C21  PFI 8  
PFI C20  C20  C 0 1 Y N N 42.774 12.558 58.821 2.173  -0.249 1.202  C20  PFI 9  
PFI C19  C19  C 0 1 Y N N 41.558 13.058 58.296 1.426  -0.819 0.187  C19  PFI 10 
PFI C18  C18  C 0 1 Y N N 40.332 12.724 58.927 2.023  -1.142 -1.017 C18  PFI 11 
PFI C12  C12  C 0 1 N N N 41.592 13.951 57.090 -0.043 -1.087 0.395  C12  PFI 12 
PFI C11  C11  C 0 1 N N N 41.192 13.124 55.809 -0.851 0.136  -0.043 C11  PFI 13 
PFI C5   C5   C 0 1 N N S 40.975 13.963 54.543 -2.342 -0.137 0.168  C5   PFI 14 
PFI C6   C6   C 0 1 N N N 42.177 14.898 54.193 -2.735 -1.424 -0.566 C6   PFI 15 
PFI C17  C17  C 0 1 N N N 39.795 14.954 54.685 -3.158 1.034  -0.383 C17  PFI 16 
PFI C13  C13  C 0 1 N N N 38.435 14.343 55.108 -2.723 2.366  0.278  C13  PFI 17 
PFI C16  C16  C 0 1 N N N 39.414 15.683 53.367 -2.834 1.273  -1.879 C16  PFI 18 
PFI C15  C15  C 0 1 N N N 38.160 16.472 53.818 -3.204 2.753  -2.114 C15  PFI 19 
PFI C14  C14  C 0 1 N N N 37.491 15.488 54.795 -3.133 3.447  -0.743 C14  PFI 20 
PFI O4   O4   O 0 1 N N N 40.656 13.101 53.391 -2.606 -0.287 1.561  O4   PFI 21 
PFI C3   C3   C 0 1 N N N 41.699 12.368 52.882 -3.926 -0.447 1.737  C3   PFI 22 
PFI O10  O10  O 0 1 N N N 41.512 11.279 52.338 -4.451 0.067  2.707  O10  PFI 23 
PFI C8   C8   C 0 1 N N N 43.078 12.927 53.008 -4.730 -1.187 0.845  C8   PFI 24 
PFI C7   C7   C 0 1 N N N 43.337 14.093 53.709 -4.199 -1.689 -0.289 C7   PFI 25 
PFI O9   O9   O 0 1 N N N 44.615 14.500 53.975 -4.949 -2.406 -1.149 O9   PFI 26 
PFI H25  H25  H 0 1 N N N 43.072 11.359 62.726 5.478  -0.156 1.688  H25  PFI 27 
PFI H21A 1H2  H 0 0 N N N 40.300 12.383 62.905 7.863  0.496  1.879  H21A PFI 28 
PFI H22  2H2  H 0 1 N N N 41.862 13.199 63.255 7.672  -0.925 0.825  H22  PFI 29 
PFI H23  3H2  H 0 1 N N N 41.080 12.179 64.510 7.954  0.681  0.111  H23  PFI 30 
PFI H11  1H1  H 0 1 N N N 41.096 9.998  64.526 4.604  2.052  0.978  H11  PFI 31 
PFI H12  2H1  H 0 1 N N N 42.892 9.973  64.549 6.071  2.235  1.968  H12  PFI 32 
PFI H13  3H1  H 0 1 N N N 41.994 8.954  63.373 6.162  2.420  0.200  H13  PFI 33 
PFI H21  H21  H 0 1 N N N 43.628 11.326 60.354 4.102  0.442  1.809  H21  PFI 34 
PFI H20  H20  H 0 1 N N N 43.721 12.811 58.368 1.704  0.003  2.141  H20  PFI 35 
PFI H18  H18  H 0 1 N N N 39.414 13.123 58.521 1.437  -1.587 -1.808 H18  PFI 36 
PFI H121 1H12 H 0 0 N N N 42.607 14.355 56.962 -0.341 -1.951 -0.198 H121 PFI 37 
PFI H122 2H12 H 0 0 N N N 40.881 14.779 57.228 -0.230 -1.288 1.450  H122 PFI 38 
PFI H111 1H11 H 0 0 N N N 40.228 12.644 56.035 -0.553 1.000  0.550  H111 PFI 39 
PFI H112 2H11 H 0 0 N N N 42.004 12.411 55.603 -0.664 0.337  -1.098 H112 PFI 40 
PFI H61  1H6  H 0 1 N N N 42.476 15.449 55.097 -2.580 -1.300 -1.638 H61  PFI 41 
PFI H62  2H6  H 0 1 N N N 41.870 15.601 53.404 -2.134 -2.256 -0.199 H62  PFI 42 
PFI H17  H17  H 0 1 N N N 40.214 15.612 55.461 -4.225 0.862  -0.239 H17  PFI 43 
PFI H131 1H13 H 0 0 N N N 38.400 14.005 56.154 -3.248 2.513  1.221  H131 PFI 44 
PFI H132 2H13 H 0 0 N N N 38.191 13.432 54.541 -1.644 2.379  0.435  H132 PFI 45 
PFI H161 1H16 H 0 0 N N N 39.240 15.010 52.514 -1.773 1.110  -2.070 H161 PFI 46 
PFI H162 2H16 H 0 0 N N N 40.217 16.343 53.006 -3.441 0.623  -2.509 H162 PFI 47 
PFI H151 1H15 H 0 0 N N N 37.509 16.774 52.985 -4.214 2.825  -2.518 H151 PFI 48 
PFI H152 2H15 H 0 0 N N N 38.425 17.421 54.307 -2.493 3.210  -2.802 H152 PFI 49 
PFI H141 1H14 H 0 0 N N N 37.244 16.017 55.727 -4.109 3.857  -0.481 H141 PFI 50 
PFI H142 2H14 H 0 0 N N N 36.574 15.088 54.337 -2.388 4.242  -0.765 H142 PFI 51 
PFI H8   H8   H 0 1 N N N 43.899 12.406 52.538 -5.773 -1.352 1.070  H8   PFI 52 
PFI HO9  HO9  H 0 1 N N N 45.094 14.594 53.160 -5.883 -2.567 -0.958 HO9  PFI 53 
# 
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 
PFI F26 C23  SING N N 1  
PFI C23 C22  SING Y N 2  
PFI C23 C18  DOUB Y N 3  
PFI C22 O24  SING N N 4  
PFI C22 C21  DOUB Y N 5  
PFI O24 C25  SING N N 6  
PFI C25 C2   SING N N 7  
PFI C25 C1   SING N N 8  
PFI C25 H25  SING N N 9  
PFI C2  H21A SING N N 10 
PFI C2  H22  SING N N 11 
PFI C2  H23  SING N N 12 
PFI C1  H11  SING N N 13 
PFI C1  H12  SING N N 14 
PFI C1  H13  SING N N 15 
PFI C21 C20  SING Y N 16 
PFI C21 H21  SING N N 17 
PFI C20 C19  DOUB Y N 18 
PFI C20 H20  SING N N 19 
PFI C19 C18  SING Y N 20 
PFI C19 C12  SING N N 21 
PFI C18 H18  SING N N 22 
PFI C12 C11  SING N N 23 
PFI C12 H121 SING N N 24 
PFI C12 H122 SING N N 25 
PFI C11 C5   SING N N 26 
PFI C11 H111 SING N N 27 
PFI C11 H112 SING N N 28 
PFI C5  C6   SING N N 29 
PFI C5  C17  SING N N 30 
PFI C5  O4   SING N N 31 
PFI C6  C7   SING N N 32 
PFI C6  H61  SING N N 33 
PFI C6  H62  SING N N 34 
PFI C17 C13  SING N N 35 
PFI C17 C16  SING N N 36 
PFI C17 H17  SING N N 37 
PFI C13 C14  SING N N 38 
PFI C13 H131 SING N N 39 
PFI C13 H132 SING N N 40 
PFI C16 C15  SING N N 41 
PFI C16 H161 SING N N 42 
PFI C16 H162 SING N N 43 
PFI C15 C14  SING N N 44 
PFI C15 H151 SING N N 45 
PFI C15 H152 SING N N 46 
PFI C14 H141 SING N N 47 
PFI C14 H142 SING N N 48 
PFI O4  C3   SING N N 49 
PFI C3  O10  DOUB N N 50 
PFI C3  C8   SING N N 51 
PFI C8  C7   DOUB N N 52 
PFI C8  H8   SING N N 53 
PFI C7  O9   SING N N 54 
PFI O9  HO9  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 
PFI SMILES           ACDLabs              10.04 Fc1c(OC(C)C)ccc(c1)CCC2(OC(=O)C=C(O)C2)C3CCCC3                                                                                                       
PFI InChI            InChI                1.02b InChI=1/C21H27FO4/c1-14(2)25-19-8-7-15(11-18(19)22)9-10-21(16-5-3-4-6-16)13-17(23)12-20(24)26-21/h7-8,11-12,14,16,23H,3-6,9-10,13H2,1-2H3/t21-/m0/s1 
PFI InChIKey         InChI                1.02b AKNIHFDXRAOPAI-NRFANRHFBG                                                                                                                            
PFI SMILES_CANONICAL CACTVS               3.341 CC(C)Oc1ccc(CC[C@]2(CC(=CC(=O)O2)O)C3CCCC3)cc1F                                                                                                      
PFI SMILES           CACTVS               3.341 CC(C)Oc1ccc(CC[C]2(CC(=CC(=O)O2)O)C3CCCC3)cc1F                                                                                                       
PFI SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(C)Oc1ccc(cc1F)CC[C@]2(CC(=CC(=O)O2)O)C3CCCC3                                                                                                      
PFI SMILES           "OpenEye OEToolkits" 1.5.0 CC(C)Oc1ccc(cc1F)CCC2(CC(=CC(=O)O2)O)C3CCCC3                                                                                                         
# 
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 
PFI "SYSTEMATIC NAME" ACDLabs              10.04 (6S)-6-cyclopentyl-6-{2-[3-fluoro-4-(1-methylethoxy)phenyl]ethyl}-4-hydroxy-5,6-dihydro-2H-pyran-2-one 
PFI "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (6S)-6-cyclopentyl-6-[2-(3-fluoro-4-propan-2-yloxy-phenyl)ethyl]-4-hydroxy-5H-pyran-2-one              
# 
