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 2011-06-04 _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 Y 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 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" S14 InChI InChI 1.03 "InChI=1S/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 1.03 ZNHVIJAGMFQGMS-IHPCNDPISA-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" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site S14 "Create component" 2006-01-26 RCSB S14 "Modify aromatic_flag" 2011-06-04 RCSB S14 "Modify descriptor" 2011-06-04 RCSB #