data_CRJ
# 
_chem_comp.id                                    CRJ 
_chem_comp.name                                  N-(1-CYANOCYCLOPROPYL)-3-({[(2S)-5-OXOPYRROLIDIN-2-YL]METHYL}SULFONYL)-N~2~-[(1S)-2,2,2-TRIFLUORO-1-(4-FLUOROPHENYL)ETHYL]-L-ALANINAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H22 F4 N4 O4 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "N-(1-CYANO-CYCLOPROPYL)-3-(5-OXO-PYRROLIDIN-2-YLMETHANESULFONYL)-2-[2,2,2-TR IFLUORO-1-(4-FLUORO-PHENYL)-ETHYLAMINO]-PROPIONAMIDE" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-01-25 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        490.472 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     CRJ 
_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        2FQ9 
_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 
CRJ C2   C2   C 0 1 Y N N 4.891  16.477 97.615  4.297  -3.558 1.267  C2   CRJ 1  
CRJ C4   C4   C 0 1 Y N N 7.026  17.544 98.100  4.032  -1.716 -0.241 C4   CRJ 2  
CRJ C5   C5   C 0 1 Y N N 6.644  17.724 99.476  2.669  -1.721 -0.008 C5   CRJ 3  
CRJ C6   C6   C 0 1 Y N N 5.352  17.258 99.891  2.120  -2.644 0.863  C6   CRJ 4  
CRJ C1   C1   C 0 1 Y N N 4.477  16.635 98.959  2.931  -3.566 1.496  C1   CRJ 5  
CRJ C3   C3   C 0 1 Y N N 6.151  16.924 97.182  4.846  -2.633 0.396  C3   CRJ 6  
CRJ C8   C8   C 0 1 N N S 7.561  18.398 100.499 1.782  -0.720 -0.702 C8   CRJ 7  
CRJ F7   F7   F 0 1 N N N 4.083  15.898 96.737  5.092  -4.456 1.890  F7   CRJ 8  
CRJ N9   N9   N 0 1 N N N 8.026  19.720 99.989  0.760  -0.238 0.236  N9   CRJ 9  
CRJ C10  C10  C 0 1 N N N 8.783  17.483 100.870 1.102  -1.387 -1.899 C10  CRJ 10 
CRJ C11  C11  C 0 1 N N R 8.036  20.821 100.967 0.348  1.091  -0.236 C11  CRJ 11 
CRJ C12  C12  C 0 1 N N N 6.593  21.323 101.218 1.346  2.121  0.225  C12  CRJ 12 
CRJ C13  C13  C 0 1 N N N 8.934  21.998 100.580 -1.033 1.428  0.332  C13  CRJ 13 
CRJ S14  S14  S 0 1 N N N 10.685 21.730 100.816 -2.266 0.293  -0.362 S14  CRJ 14 
CRJ C15  C15  C 0 1 N N N 11.175 20.784 99.399  -3.771 1.034  0.326  C15  CRJ 15 
CRJ N16  N16  N 0 1 N N N 6.388  21.635 102.568 1.171  3.419  -0.093 N16  CRJ 16 
CRJ O17  O17  O 0 1 N N N 5.762  21.424 100.332 2.307  1.782  0.883  O17  CRJ 17 
CRJ C18  C18  C 0 1 N N S 12.467 20.005 99.601  -4.990 0.230  -0.131 C18  CRJ 18 
CRJ C19  C19  C 0 1 N N N 13.081 19.372 98.356  -6.290 0.901  0.367  C19  CRJ 19 
CRJ C20  C20  C 0 1 N N N 13.802 18.131 98.874  -7.181 -0.326 0.670  C20  CRJ 20 
CRJ C21  C21  C 0 1 N N N 13.070 17.806 100.145 -6.197 -1.444 0.936  C21  CRJ 21 
CRJ N22  N22  N 0 1 N N N 12.338 18.898 100.508 -4.977 -1.104 0.480  N22  CRJ 22 
CRJ O23  O23  O 0 1 N N N 13.121 16.750 100.752 -6.468 -2.494 1.478  O23  CRJ 23 
CRJ C24  C24  C 0 1 N N N 5.196  22.159 103.286 2.142  4.420  0.356  C24  CRJ 24 
CRJ C25  C25  C 0 1 N N N 3.979  21.210 103.116 1.887  5.877  -0.037 C25  CRJ 25 
CRJ C26  C26  C 0 1 N N N 4.486  21.632 104.480 1.680  5.428  1.411  C26  CRJ 26 
CRJ O27  O27  O 0 1 N N N 10.878 20.897 101.991 -2.283 0.437  -1.776 O27  CRJ 27 
CRJ O28  O28  O 0 1 N N N 11.349 23.010 100.697 -2.082 -0.995 0.209  O28  CRJ 28 
CRJ F29  F29  F 0 1 N N N 9.613  17.259 99.822  0.329  -2.465 -1.456 F29  CRJ 29 
CRJ F30  F30  F 0 1 N N N 8.369  16.275 101.324 0.278  -0.458 -2.544 F30  CRJ 30 
CRJ F31  F31  F 0 1 N N N 9.535  18.033 101.860 2.075  -1.847 -2.793 F31  CRJ 31 
CRJ N33  N33  N 0 1 N N N 3.898  24.277 103.517 4.621  3.616  0.460  N33  CRJ 32 
CRJ C32  C32  C 0 1 N N N 4.854  23.607 102.986 3.541  3.966  0.415  C32  CRJ 33 
CRJ H4   H4   H 0 1 N N N 7.994  17.887 97.766  4.460  -0.994 -0.920 H4   CRJ 34 
CRJ H6   H6   H 0 1 N N N 5.042  17.381 100.918 1.055  -2.647 1.045  H6   CRJ 35 
CRJ H1   H1   H 0 1 N N N 3.505  16.285 99.274  2.502  -4.287 2.176  H1   CRJ 36 
CRJ H3   H3   H 0 1 N N N 6.448  16.794 96.152  5.911  -2.628 0.213  H3   CRJ 37 
CRJ H8   H8   H 0 1 N N N 6.979  18.560 101.418 2.384  0.120  -1.048 H8   CRJ 38 
CRJ HN9  HN9  H 0 1 N N N 8.964  19.601 99.664  -0.039 -0.844 0.131  HN9  CRJ 39 
CRJ H11  H11  H 0 1 N N N 8.465  20.399 101.888 0.302  1.091  -1.325 H11  CRJ 40 
CRJ H131 1H13 H 0 0 N N N 8.657  22.829 101.245 -1.014 1.325  1.417  H131 CRJ 41 
CRJ H132 2H13 H 0 0 N N N 8.770  22.204 99.512  -1.293 2.453  0.068  H132 CRJ 42 
CRJ H151 1H15 H 0 0 N N N 11.351 21.496 98.579  -3.717 1.024  1.414  H151 CRJ 43 
CRJ H152 2H15 H 0 0 N N N 10.374 20.064 99.175  -3.863 2.063  -0.024 H152 CRJ 44 
CRJ HN16 HN16 H 0 0 N N N 7.184  21.477 103.152 0.403  3.690  -0.619 HN16 CRJ 45 
CRJ H18  H18  H 0 1 N N N 13.110 20.812 99.982  -5.001 0.147  -1.218 H18  CRJ 46 
CRJ H191 1H19 H 0 0 N N N 13.761 20.060 97.832  -6.107 1.483  1.270  H191 CRJ 47 
CRJ H192 2H19 H 0 0 N N N 12.306 19.104 97.623  -6.732 1.521  -0.413 H192 CRJ 48 
CRJ H201 1H20 H 0 0 N N N 14.878 18.298 99.032  -7.796 -0.142 1.551  H201 CRJ 49 
CRJ H202 2H20 H 0 0 N N N 13.747 17.302 98.153  -7.807 -0.565 -0.190 H202 CRJ 50 
CRJ HN22 HN22 H 0 0 N N N 11.766 18.926 101.328 -4.190 -1.668 0.549  HN22 CRJ 51 
CRJ H251 1H25 H 0 0 N N N 3.759  20.267 102.594 2.756  6.499  -0.252 H251 CRJ 52 
CRJ H252 2H25 H 0 0 N N N 3.007  21.340 102.618 0.998  6.090  -0.630 H252 CRJ 53 
CRJ H261 1H26 H 0 0 N N N 4.027  22.085 105.371 0.655  5.346  1.771  H261 CRJ 54 
CRJ H262 2H26 H 0 0 N N N 4.868  21.016 105.308 2.413  5.755  2.148  H262 CRJ 55 
# 
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 
CRJ C2  C1   SING Y N 1  
CRJ C2  C3   DOUB Y N 2  
CRJ C2  F7   SING N N 3  
CRJ C4  C5   DOUB Y N 4  
CRJ C4  C3   SING Y N 5  
CRJ C4  H4   SING N N 6  
CRJ C5  C6   SING Y N 7  
CRJ C5  C8   SING N N 8  
CRJ C6  C1   DOUB Y N 9  
CRJ C6  H6   SING N N 10 
CRJ C1  H1   SING N N 11 
CRJ C3  H3   SING N N 12 
CRJ C8  N9   SING N N 13 
CRJ C8  C10  SING N N 14 
CRJ C8  H8   SING N N 15 
CRJ N9  C11  SING N N 16 
CRJ N9  HN9  SING N N 17 
CRJ C10 F29  SING N N 18 
CRJ C10 F30  SING N N 19 
CRJ C10 F31  SING N N 20 
CRJ C11 C12  SING N N 21 
CRJ C11 C13  SING N N 22 
CRJ C11 H11  SING N N 23 
CRJ C12 N16  SING N N 24 
CRJ C12 O17  DOUB N N 25 
CRJ C13 S14  SING N N 26 
CRJ C13 H131 SING N N 27 
CRJ C13 H132 SING N N 28 
CRJ S14 C15  SING N N 29 
CRJ S14 O27  DOUB N N 30 
CRJ S14 O28  DOUB N N 31 
CRJ C15 C18  SING N N 32 
CRJ C15 H151 SING N N 33 
CRJ C15 H152 SING N N 34 
CRJ N16 C24  SING N N 35 
CRJ N16 HN16 SING N N 36 
CRJ C18 C19  SING N N 37 
CRJ C18 N22  SING N N 38 
CRJ C18 H18  SING N N 39 
CRJ C19 C20  SING N N 40 
CRJ C19 H191 SING N N 41 
CRJ C19 H192 SING N N 42 
CRJ C20 C21  SING N N 43 
CRJ C20 H201 SING N N 44 
CRJ C20 H202 SING N N 45 
CRJ C21 N22  SING N N 46 
CRJ C21 O23  DOUB N N 47 
CRJ N22 HN22 SING N N 48 
CRJ C24 C25  SING N N 49 
CRJ C24 C26  SING N N 50 
CRJ C24 C32  SING N N 51 
CRJ C25 C26  SING N N 52 
CRJ C25 H251 SING N N 53 
CRJ C25 H252 SING N N 54 
CRJ C26 H261 SING N N 55 
CRJ C26 H262 SING N N 56 
CRJ N33 C32  TRIP N N 57 
# 
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 
CRJ SMILES           ACDLabs              10.04 O=C3NC(CS(=O)(=O)CC(C(=O)NC1(C#N)CC1)NC(c2ccc(F)cc2)C(F)(F)F)CC3                                                                                                                                   
CRJ InChI            InChI                1.02b InChI=1/C20H22F4N4O4S/c21-13-3-1-12(2-4-13)17(20(22,23)24)27-15(18(30)28-19(11-25)7-8-19)10-33(31,32)9-14-5-6-16(29)26-14/h1-4,14-15,17,27H,5-10H2,(H,26,29)(H,28,30)/t14-,15-,17-/m0/s1/f/h26,28H 
CRJ InChIKey         InChI                1.02b JLPXDVXMMYRTKN-YHXJJEENDT                                                                                                                                                                          
CRJ SMILES_CANONICAL CACTVS               3.341 Fc1ccc(cc1)[C@H](N[C@@H](C[S](=O)(=O)C[C@@H]2CCC(=O)N2)C(=O)NC3(CC3)C#N)C(F)(F)F                                                                                                                   
CRJ SMILES           CACTVS               3.341 Fc1ccc(cc1)[CH](N[CH](C[S](=O)(=O)C[CH]2CCC(=O)N2)C(=O)NC3(CC3)C#N)C(F)(F)F                                                                                                                        
CRJ SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(ccc1[C@@H](C(F)(F)F)N[C@@H](CS(=O)(=O)C[C@@H]2CCC(=O)N2)C(=O)NC3(CC3)C#N)F                                                                                                                    
CRJ SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(ccc1C(C(F)(F)F)NC(CS(=O)(=O)CC2CCC(=O)N2)C(=O)NC3(CC3)C#N)F                                                                                                                                   
# 
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 
CRJ "SYSTEMATIC NAME" ACDLabs              10.04 N-(1-cyanocyclopropyl)-3-({[(2S)-5-oxopyrrolidin-2-yl]methyl}sulfonyl)-N~2~-[(1S)-2,2,2-trifluoro-1-(4-fluorophenyl)ethyl]-L-alaninamide     
CRJ "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2R)-N-(1-cyanocyclopropyl)-3-[[(2S)-5-oxopyrrolidin-2-yl]methylsulfonyl]-2-[[(1S)-2,2,2-trifluoro-1-(4-fluorophenyl)ethyl]amino]propanamide 
# 
