data_1HL # _chem_comp.id 1HL _chem_comp.name "N-{3-[(4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl]-4-fluorophenyl}-5-cyanopyridine-2-carboxamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C19 H15 F4 N5 O2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2013-02-07 _chem_comp.pdbx_modified_date 2013-04-26 _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 421.348 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 1HL _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details Corina _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 4J1F _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 1HL C1 C1 C 0 1 N N S -15.705 -42.000 -9.499 -3.549 -0.864 0.433 C1 1HL 1 1HL C2 C2 C 0 1 N N N -15.997 -40.626 -10.123 -3.883 0.315 -0.492 C2 1HL 2 1HL O3 O3 O 0 1 N N N -14.833 -41.906 -8.366 -3.354 -2.024 -0.384 O3 1HL 3 1HL C4 C4 C 0 1 N N N -14.805 -40.756 -7.645 -2.587 -1.886 -1.482 C4 1HL 4 1HL N5 N5 N 0 1 N N N -15.548 -39.698 -7.886 -2.269 -0.748 -1.995 N5 1HL 5 1HL C6 C6 C 0 1 N N S -16.443 -39.613 -9.030 -2.696 0.532 -1.436 C6 1HL 6 1HL C7 C7 C 0 1 Y N N -17.909 -39.935 -8.687 -1.554 1.150 -0.671 C7 1HL 7 1HL C8 C8 C 0 1 Y N N -18.189 -40.481 -7.445 -0.343 0.492 -0.587 C8 1HL 8 1HL C9 C9 C 0 1 Y N N -19.511 -40.806 -7.117 0.709 1.062 0.118 C9 1HL 9 1HL C10 C10 C 0 1 Y N N -20.576 -40.631 -8.026 0.540 2.293 0.738 C10 1HL 10 1HL C11 C11 C 0 1 Y N N -20.275 -40.113 -9.289 -0.672 2.948 0.651 C11 1HL 11 1HL C12 C12 C 0 1 Y N N -18.950 -39.750 -9.622 -1.718 2.381 -0.057 C12 1HL 12 1HL F13 F13 F 0 1 N N N -18.697 -39.253 -10.898 -2.904 3.023 -0.140 F13 1HL 13 1HL N14 N14 N 0 1 N N N -13.941 -40.770 -6.552 -2.117 -3.025 -2.089 N14 1HL 14 1HL C15 C15 C 0 1 N N N -16.239 -38.193 -9.585 -3.113 1.469 -2.572 C15 1HL 15 1HL N16 N16 N 0 1 N N N -19.680 -41.385 -5.880 1.937 0.396 0.205 N16 1HL 16 1HL C17 C17 C 0 1 N N N -20.811 -41.962 -5.368 3.086 1.101 0.214 C17 1HL 17 1HL C18 C18 C 0 1 Y N N -20.673 -42.571 -4.042 4.388 0.394 0.202 C18 1HL 18 1HL O19 O19 O 0 1 N N N -21.884 -41.983 -5.940 3.054 2.315 0.232 O19 1HL 19 1HL N20 N20 N 0 1 Y N N -19.562 -42.294 -3.332 4.413 -0.934 0.177 N20 1HL 20 1HL C21 C21 C 0 1 Y N N -19.371 -42.820 -2.123 5.542 -1.605 0.166 C21 1HL 21 1HL C22 C22 C 0 1 Y N N -20.313 -43.721 -1.564 6.770 -0.936 0.180 C22 1HL 22 1HL C23 C23 C 0 1 Y N N -21.490 -44.054 -2.326 6.783 0.463 0.206 C23 1HL 23 1HL C24 C24 C 0 1 Y N N -21.677 -43.464 -3.586 5.571 1.131 0.212 C24 1HL 24 1HL C25 C25 C 0 1 N N N -20.091 -44.293 -0.260 7.998 -1.673 0.168 C25 1HL 25 1HL N26 N26 N 0 1 N N N -19.939 -44.765 0.782 8.972 -2.258 0.158 N26 1HL 26 1HL C27 C27 C 0 1 N N N -14.951 -42.865 -10.518 -4.705 -1.105 1.405 C27 1HL 27 1HL F28 F28 F 0 1 N N N -14.677 -44.101 -9.932 -4.407 -2.201 2.221 F28 1HL 28 1HL F29 F29 F 0 1 N N N -15.851 -43.137 -11.524 -4.890 0.032 2.200 F29 1HL 29 1HL F30 F30 F 0 1 N N N -13.779 -42.213 -11.015 -5.875 -1.365 0.683 F30 1HL 30 1HL H1 H1 H 0 1 N N N -16.652 -42.490 -9.229 -2.637 -0.649 0.990 H1 1HL 31 1HL H2 H2 H 0 1 N N N -15.087 -40.251 -10.614 -4.777 0.086 -1.072 H2 1HL 32 1HL H3 H3 H 0 1 N N N -16.799 -40.730 -10.868 -4.049 1.213 0.103 H3 1HL 33 1HL H4 H4 H 0 1 N N N -17.394 -40.655 -6.735 -0.214 -0.466 -1.069 H4 1HL 34 1HL H5 H5 H 0 1 N N N -21.589 -40.889 -7.755 1.357 2.738 1.287 H5 1HL 35 1HL H6 H6 H 0 1 N N N -21.063 -39.989 -10.018 -0.804 3.906 1.133 H6 1HL 36 1HL H7 H7 H 0 1 N N N -13.401 -41.588 -6.352 -2.339 -3.896 -1.725 H7 1HL 37 1HL H8 H8 H 0 1 N N N -13.860 -39.962 -5.968 -1.562 -2.957 -2.882 H8 1HL 38 1HL H9 H9 H 0 1 N N N -16.548 -37.456 -8.829 -3.427 2.426 -2.156 H9 1HL 39 1HL H10 H10 H 0 1 N N N -15.177 -38.044 -9.830 -2.269 1.623 -3.243 H10 1HL 40 1HL H11 H11 H 0 1 N N N -16.846 -38.064 -10.493 -3.940 1.023 -3.124 H11 1HL 41 1HL H12 H12 H 0 1 N N N -18.879 -41.384 -5.282 1.961 -0.572 0.258 H12 1HL 42 1HL H13 H13 H 0 1 N N N -18.487 -42.557 -1.561 5.521 -2.685 0.145 H13 1HL 43 1HL H14 H14 H 0 1 N N N -22.218 -44.748 -1.933 7.715 1.008 0.218 H14 1HL 44 1HL H15 H15 H 0 1 N N N -22.550 -43.681 -4.184 5.542 2.210 0.228 H15 1HL 45 # 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 1HL F29 C27 SING N N 1 1HL F30 C27 SING N N 2 1HL F13 C12 SING N N 3 1HL C27 F28 SING N N 4 1HL C27 C1 SING N N 5 1HL C2 C1 SING N N 6 1HL C2 C6 SING N N 7 1HL C12 C11 DOUB Y N 8 1HL C12 C7 SING Y N 9 1HL C15 C6 SING N N 10 1HL C1 O3 SING N N 11 1HL C11 C10 SING Y N 12 1HL C6 C7 SING N N 13 1HL C6 N5 SING N N 14 1HL C7 C8 DOUB Y N 15 1HL O3 C4 SING N N 16 1HL C10 C9 DOUB Y N 17 1HL N5 C4 DOUB N N 18 1HL C4 N14 SING N N 19 1HL C8 C9 SING Y N 20 1HL C9 N16 SING N N 21 1HL O19 C17 DOUB N N 22 1HL N16 C17 SING N N 23 1HL C17 C18 SING N N 24 1HL C18 C24 DOUB Y N 25 1HL C18 N20 SING Y N 26 1HL C24 C23 SING Y N 27 1HL N20 C21 DOUB Y N 28 1HL C23 C22 DOUB Y N 29 1HL C21 C22 SING Y N 30 1HL C22 C25 SING N N 31 1HL C25 N26 TRIP N N 32 1HL C1 H1 SING N N 33 1HL C2 H2 SING N N 34 1HL C2 H3 SING N N 35 1HL C8 H4 SING N N 36 1HL C10 H5 SING N N 37 1HL C11 H6 SING N N 38 1HL N14 H7 SING N N 39 1HL N14 H8 SING N N 40 1HL C15 H9 SING N N 41 1HL C15 H10 SING N N 42 1HL C15 H11 SING N N 43 1HL N16 H12 SING N N 44 1HL C21 H13 SING N N 45 1HL C23 H14 SING N N 46 1HL C24 H15 SING N N 47 # 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 1HL SMILES ACDLabs 12.01 "FC(F)(F)C3OC(=NC(c2cc(NC(=O)c1ncc(C#N)cc1)ccc2F)(C)C3)N" 1HL InChI InChI 1.03 "InChI=1S/C19H15F4N5O2/c1-18(7-15(19(21,22)23)30-17(25)28-18)12-6-11(3-4-13(12)20)27-16(29)14-5-2-10(8-24)9-26-14/h2-6,9,15H,7H2,1H3,(H2,25,28)(H,27,29)/t15-,18-/m0/s1" 1HL InChIKey InChI 1.03 MELQHVBGGSKVJQ-YJBOKZPZSA-N 1HL SMILES_CANONICAL CACTVS 3.370 "C[C@]1(C[C@H](OC(=N1)N)C(F)(F)F)c2cc(NC(=O)c3ccc(cn3)C#N)ccc2F" 1HL SMILES CACTVS 3.370 "C[C]1(C[CH](OC(=N1)N)C(F)(F)F)c2cc(NC(=O)c3ccc(cn3)C#N)ccc2F" 1HL SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "C[C@]1(C[C@H](OC(=N1)N)C(F)(F)F)c2cc(ccc2F)NC(=O)c3ccc(cn3)C#N" 1HL SMILES "OpenEye OEToolkits" 1.7.6 "CC1(CC(OC(=N1)N)C(F)(F)F)c2cc(ccc2F)NC(=O)c3ccc(cn3)C#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 1HL "SYSTEMATIC NAME" ACDLabs 12.01 "N-{3-[(4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl]-4-fluorophenyl}-5-cyanopyridine-2-carboxamide" 1HL "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "N-[3-[(4S,6S)-2-azanyl-4-methyl-6-(trifluoromethyl)-5,6-dihydro-1,3-oxazin-4-yl]-4-fluoranyl-phenyl]-5-cyano-pyridine-2-carboxamide" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 1HL "Create component" 2013-02-07 RCSB 1HL "Initial release" 2013-05-01 RCSB #