data_S14
# 
_chem_comp.id                                    S14 
_chem_comp.name                                  6-(4-{(1S,2S)-2-AMINO-1-[(DIMETHYLAMINO)CARBONYL]-3-[(3S)-3-FLUOROPYRROLIDIN-1-YL]-3-OXOPROPYL}PHENYL)-1H-[1,2,4]TRIAZOLO[1,5-A]PYRIDIN-4-IUM 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H25 F N6 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-01-26 
_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                        424.471 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     S14 
_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        2FJP 
_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 
S14 C1   C1   C 0 1 Y N N 47.575 52.153 33.822 6.777  -0.459 0.561  C1   S14 1  
S14 C2   C2   C 0 1 Y N N 46.492 52.656 32.959 6.117  -1.673 0.288  C2   S14 2  
S14 C3   C3   C 0 1 Y N N 45.199 52.472 33.370 4.783  -1.664 0.030  C3   S14 3  
S14 C4   C4   C 0 1 Y N N 44.874 51.804 34.672 4.080  -0.439 0.040  C4   S14 4  
S14 C5   C5   C 0 1 Y N N 45.894 51.348 35.453 4.742  0.723  0.301  C5   S14 5  
S14 N6   N6   N 0 1 Y N N 47.284 51.554 35.012 6.074  0.712  0.564  N6   S14 6  
S14 N7   N7   N 0 1 Y N N 48.329 51.205 35.590 6.999  1.722  0.864  N7   S14 7  
S14 C8   C8   C 0 1 Y N N 49.329 51.606 34.791 8.166  1.142  1.021  C8   S14 8  
S14 N9   N9   N 0 1 Y N N 48.902 52.215 33.667 8.041  -0.165 0.841  N9   S14 9  
S14 C14  C14  C 0 1 Y N N 43.482 51.633 35.137 2.622  -0.417 -0.241 C14  S14 10 
S14 C15  C15  C 0 1 Y N N 42.598 52.738 35.028 2.146  -0.786 -1.497 C15  S14 11 
S14 C16  C16  C 0 1 Y N N 41.282 52.658 35.482 0.790  -0.764 -1.752 C16  S14 12 
S14 C17  C17  C 0 1 Y N N 40.778 51.471 36.063 -0.096 -0.377 -0.763 C17  S14 13 
S14 C18  C18  C 0 1 Y N N 41.662 50.336 36.166 0.371  -0.005 0.485  C18  S14 14 
S14 C19  C19  C 0 1 Y N N 43.004 50.411 35.708 1.725  -0.028 0.752  C19  S14 15 
S14 C24  C24  C 0 1 N N S 39.318 51.486 36.572 -1.576 -0.355 -1.047 C24  S14 16 
S14 C25  C25  C 0 1 N N S 38.346 50.990 35.442 -2.294 -1.307 -0.089 C25  S14 17 
S14 C26  C26  C 0 1 N N N 36.897 51.030 36.024 -3.754 -1.381 -0.453 C26  S14 18 
S14 N27  N27  N 0 1 N N N 36.122 49.968 35.796 -4.683 -0.870 0.379  N27  S14 19 
S14 C28  C28  C 0 1 N N N 39.294 50.453 37.798 -2.104 1.043  -0.855 C28  S14 20 
S14 N30  N30  N 0 1 N N N 38.422 51.823 34.248 -1.696 -2.646 -0.189 N30  S14 21 
S14 O32  O32  O 0 1 N N N 36.510 51.996 36.663 -4.093 -1.900 -1.496 O32  S14 22 
S14 O33  O33  O 0 1 N N N 38.665 49.386 37.800 -2.611 1.360  0.200  O33  S14 23 
S14 N34  N34  N 0 1 N N N 39.903 50.955 38.983 -2.012 1.941  -1.856 N34  S14 24 
S14 C35  C35  C 0 1 N N N 39.898 50.039 40.150 -2.525 3.301  -1.669 C35  S14 25 
S14 C39  C39  C 0 1 N N N 40.509 52.283 39.186 -1.399 1.558  -3.130 C39  S14 26 
S14 C43  C43  C 0 1 N N N 36.569 48.548 35.469 -4.426 -0.331 1.722  C43  S14 27 
S14 C44  C44  C 0 1 N N S 35.362 47.686 35.516 -5.776 0.164  2.283  C44  S14 28 
S14 C45  C45  C 0 1 N N N 34.187 48.637 35.525 -6.626 0.385  1.004  C45  S14 29 
S14 C46  C46  C 0 1 N N N 34.686 50.013 35.968 -6.126 -0.765 0.095  C46  S14 30 
S14 F53  F53  F 0 1 N N N 35.367 47.021 36.724 -5.618 1.363  2.986  F53  S14 31 
S14 H2   H2   H 0 1 N N N 46.712 53.156 32.027 6.667  -2.603 0.285  H2   S14 32 
S14 H3   H3   H 0 1 N N N 44.393 52.817 32.740 4.263  -2.588 -0.180 H3   S14 33 
S14 H5   H5   H 0 1 N N N 45.685 50.842 36.384 4.202  1.659  0.301  H5   S14 34 
S14 H8   H8   H 0 1 N N N 50.373 51.456 35.025 9.087  1.653  1.261  H8   S14 35 
S14 H15  H15  H 0 1 N N N 42.951 53.658 34.585 2.837  -1.089 -2.270 H15  S14 36 
S14 H16  H16  H 0 1 N N N 40.636 53.518 35.388 0.420  -1.050 -2.726 H16  S14 37 
S14 H18  H18  H 0 1 N N N 41.298 49.415 36.598 -0.325 0.296  1.253  H18  S14 38 
S14 H19  H19  H 0 1 N N N 43.657 49.555 35.790 2.089  0.258  1.728  H19  S14 39 
S14 H24  H24  H 0 1 N N N 38.995 52.495 36.867 -1.753 -0.673 -2.075 H24  S14 40 
S14 H25  H25  H 0 1 N N N 38.632 49.972 35.138 -2.192 -0.940 0.932  H25  S14 41 
S14 H301 1H30 H 0 0 N N N 38.439 52.787 34.514 -2.262 -3.259 0.378  H301 S14 42 
S14 H302 2H30 H 0 0 N N N 39.255 51.602 33.740 -1.812 -2.944 -1.145 H302 S14 43 
S14 H351 1H35 H 0 0 N N N 39.897 48.997 39.799 -2.364 3.878  -2.580 H351 S14 44 
S14 H352 2H35 H 0 0 N N N 40.795 50.219 40.761 -3.592 3.259  -1.449 H352 S14 45 
S14 H353 3H35 H 0 0 N N N 38.998 50.222 40.756 -2.001 3.776  -0.840 H353 S14 46 
S14 H391 1H39 H 0 0 N N N 40.660 52.457 40.262 -1.080 0.517  -3.082 H391 S14 47 
S14 H392 2H39 H 0 0 N N N 41.478 52.327 38.668 -2.127 1.678  -3.934 H392 S14 48 
S14 H393 3H39 H 0 0 N N N 39.841 53.057 38.780 -0.536 2.194  -3.324 H393 S14 49 
S14 H431 1H43 H 0 0 N N N 37.311 48.204 36.204 -4.019 -1.109 2.368  H431 S14 50 
S14 H432 2H43 H 0 0 N N N 37.038 48.507 34.475 -3.725 0.502  1.654  H432 S14 51 
S14 H44  H44  H 0 1 N N N 35.323 46.971 34.681 -6.228 -0.597 2.919  H44  S14 52 
S14 H451 1H45 H 0 0 N N N 33.753 48.704 34.517 -6.414 1.357  0.557  H451 S14 53 
S14 H452 2H45 H 0 0 N N N 33.412 48.275 36.217 -7.689 0.280  1.218  H452 S14 54 
S14 H461 1H46 H 0 0 N N N 34.241 50.809 35.353 -6.289 -0.518 -0.954 H461 S14 55 
S14 H462 2H46 H 0 0 N N N 34.405 50.236 37.008 -6.631 -1.697 0.350  H462 S14 56 
# 
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 
S14 C1  C2   SING Y N 1  
S14 C1  N6   SING Y N 2  
S14 C1  N9   DOUB Y N 3  
S14 C2  C3   DOUB Y N 4  
S14 C2  H2   SING N N 5  
S14 C3  C4   SING Y N 6  
S14 C3  H3   SING N N 7  
S14 C4  C5   DOUB Y N 8  
S14 C4  C14  SING N N 9  
S14 C5  N6   SING Y N 10 
S14 C5  H5   SING N N 11 
S14 N6  N7   SING Y N 12 
S14 N7  C8   DOUB Y N 13 
S14 C8  N9   SING Y N 14 
S14 C8  H8   SING N N 15 
S14 C14 C15  DOUB Y N 16 
S14 C14 C19  SING Y N 17 
S14 C15 C16  SING Y N 18 
S14 C15 H15  SING N N 19 
S14 C16 C17  DOUB Y N 20 
S14 C16 H16  SING N N 21 
S14 C17 C18  SING Y N 22 
S14 C17 C24  SING N N 23 
S14 C18 C19  DOUB Y N 24 
S14 C18 H18  SING N N 25 
S14 C19 H19  SING N N 26 
S14 C24 C25  SING N N 27 
S14 C24 C28  SING N N 28 
S14 C24 H24  SING N N 29 
S14 C25 C26  SING N N 30 
S14 C25 N30  SING N N 31 
S14 C25 H25  SING N N 32 
S14 C26 N27  SING N N 33 
S14 C26 O32  DOUB N N 34 
S14 N27 C43  SING N N 35 
S14 N27 C46  SING N N 36 
S14 C28 O33  DOUB N N 37 
S14 C28 N34  SING N N 38 
S14 N30 H301 SING N N 39 
S14 N30 H302 SING N N 40 
S14 N34 C35  SING N N 41 
S14 N34 C39  SING N N 42 
S14 C35 H351 SING N N 43 
S14 C35 H352 SING N N 44 
S14 C35 H353 SING N N 45 
S14 C39 H391 SING N N 46 
S14 C39 H392 SING N N 47 
S14 C39 H393 SING N N 48 
S14 C43 C44  SING N N 49 
S14 C43 H431 SING N N 50 
S14 C43 H432 SING N N 51 
S14 C44 C45  SING N N 52 
S14 C44 F53  SING N N 53 
S14 C44 H44  SING N N 54 
S14 C45 C46  SING N N 55 
S14 C45 H451 SING N N 56 
S14 C45 H452 SING N N 57 
S14 C46 H461 SING N N 58 
S14 C46 H462 SING N N 59 
# 
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 
S14 SMILES           ACDLabs              10.04 FC4CCN(C(=O)C(N)C(C(=O)N(C)C)c3ccc(c1ccc2ncnn2c1)cc3)C4                                                                                                                         
S14 InChI            InChI                1.02b InChI=1/C22H25FN6O2/c1-27(2)21(30)19(20(24)22(31)28-10-9-17(23)12-28)15-5-3-14(4-6-15)16-7-8-18-25-13-26-29(18)11-16/h3-8,11,13,17,19-20H,9-10,12,24H2,1-2H3/t17-,19-,20-/m0/s1 
S14 InChIKey         InChI                1.02b ZNHVIJAGMFQGMS-IHPCNDPIBZ                                                                                                                                                       
S14 SMILES_CANONICAL CACTVS               3.341 CN(C)C(=O)[C@H]([C@H](N)C(=O)N1CC[C@H](F)C1)c2ccc(cc2)c3ccc4ncnn4c3                                                                                                             
S14 SMILES           CACTVS               3.341 CN(C)C(=O)[CH]([CH](N)C(=O)N1CC[CH](F)C1)c2ccc(cc2)c3ccc4ncnn4c3                                                                                                                
S14 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CN(C)C(=O)[C@@H](c1ccc(cc1)c2ccc3ncnn3c2)[C@@H](C(=O)N4CC[C@@H](C4)F)N                                                                                                          
S14 SMILES           "OpenEye OEToolkits" 1.5.0 CN(C)C(=O)C(c1ccc(cc1)c2ccc3ncnn3c2)C(C(=O)N4CCC(C4)F)N                                                                                                                         
# 
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 
S14 "SYSTEMATIC NAME" ACDLabs              10.04 (2S,3S)-3-amino-4-[(3S)-3-fluoropyrrolidin-1-yl]-N,N-dimethyl-4-oxo-2-(4-[1,2,4]triazolo[1,5-a]pyridin-6-ylphenyl)butanamide   
S14 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2S,3S)-3-amino-4-[(3S)-3-fluoropyrrolidin-1-yl]-N,N-dimethyl-4-oxo-2-[4-([1,2,4]triazolo[5,1-f]pyridin-6-yl)phenyl]butanamide 
# 
