data_1HQ
# 
_chem_comp.id                                    1HQ 
_chem_comp.name                                  "N-{3-[(4S)-2-amino-4-(difluoromethyl)-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                               "C18 H14 F3 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                        389.331 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     1HQ 
_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        4J17 
_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 
1HQ C2  C2  C 0 1 Y N N -22.218 -43.459 -2.289  6.337  0.382  0.684  C2  1HQ 1  
1HQ C3  C3  C 0 1 Y N N -22.372 -42.798 -3.500  5.096  0.986  0.789  C3  1HQ 2  
1HQ C4  C4  C 0 1 Y N N -21.426 -41.880 -3.941  4.006  0.418  0.132  C4  1HQ 3  
1HQ N5  N5  N 0 1 Y N N -20.370 -41.591 -3.230  4.145  -0.689 -0.588 N5  1HQ 4  
1HQ C6  C6  C 0 1 Y N N -20.115 -42.178 -2.072  5.305  -1.293 -0.712 C6  1HQ 5  
1HQ N9  N9  N 0 1 N N N -20.429 -40.584 -5.719  1.613  0.516  -0.392 N9  1HQ 6  
1HQ C15 C15 C 0 1 Y N N -19.644 -38.951 -9.461  -2.184 2.147  0.139  C15 1HQ 7  
1HQ C1  C1  C 0 1 Y N N -21.022 -43.136 -1.588  6.446  -0.784 -0.083 C1  1HQ 8  
1HQ C7  C7  C 0 1 N N N -21.545 -41.199 -5.235  2.674  1.058  0.239  C7  1HQ 9  
1HQ O8  O8  O 0 1 N N N -22.591 -41.251 -5.873  2.538  2.071  0.896  O8  1HQ 10 
1HQ C10 C10 C 0 1 N N N -20.776 -43.758 -0.325  7.709  -1.443 -0.227 C10 1HQ 11 
1HQ N11 N11 N 0 1 N N N -20.599 -44.247 0.663   8.712  -1.965 -0.341 N11 1HQ 12 
1HQ C12 C12 C 0 1 Y N N -20.257 -39.962 -6.951  0.338  1.064  -0.214 C12 1HQ 13 
1HQ C13 C13 C 0 1 Y N N -21.333 -39.708 -7.865  0.186  2.435  -0.058 C13 1HQ 14 
1HQ C14 C14 C 0 1 Y N N -20.992 -39.225 -9.150  -1.074 2.974  0.118  C14 1HQ 15 
1HQ C16 C16 C 0 1 Y N N -18.576 -39.217 -8.526  -2.035 0.779  -0.016 C16 1HQ 16 
1HQ C17 C17 C 0 1 Y N N -18.904 -39.755 -7.299  -0.777 0.236  -0.192 C17 1HQ 17 
1HQ F18 F18 F 0 1 N N N -19.252 -38.444 -10.701 -3.415 2.675  0.316  F18 1HQ 18 
1HQ C19 C19 C 0 1 N N S -17.089 -39.005 -8.911  -3.245 -0.118 0.008  C19 1HQ 19 
1HQ C20 C20 C 0 1 N N N -16.565 -40.053 -9.944  -3.965 0.033  1.352  C20 1HQ 20 
1HQ C21 C21 C 0 1 N N N -16.466 -41.436 -9.312  -4.982 -1.111 1.480  C21 1HQ 21 
1HQ O22 O22 O 0 1 N N N -15.544 -41.229 -8.174  -4.262 -2.348 1.446  O22 1HQ 22 
1HQ C23 C23 C 0 1 N N N -15.514 -40.125 -7.439  -3.318 -2.489 0.498  C23 1HQ 23 
1HQ N24 N24 N 0 1 N N N -16.199 -39.065 -7.708  -2.825 -1.506 -0.174 N24 1HQ 24 
1HQ C25 C25 C 0 1 N N N -16.858 -37.631 -9.480  -4.195 0.278  -1.124 C25 1HQ 25 
1HQ F26 F26 F 0 1 N N N -17.255 -36.646 -8.587  -3.538 0.144  -2.352 F26 1HQ 26 
1HQ F27 F27 F 0 1 N N N -15.522 -37.461 -9.716  -5.319 -0.554 -1.103 F27 1HQ 27 
1HQ N28 N28 N 0 1 N N N -14.709 -40.178 -6.276  -2.852 -3.753 0.232  N28 1HQ 28 
1HQ H1  H1  H 0 1 N N N -22.946 -44.161 -1.910  7.200  0.802  1.178  H1  1HQ 29 
1HQ H2  H2  H 0 1 N N N -23.241 -43.000 -4.109  4.974  1.886  1.372  H2  1HQ 30 
1HQ H3  H3  H 0 1 N N N -19.228 -41.926 -1.510  5.378  -2.192 -1.306 H3  1HQ 31 
1HQ H4  H4  H 0 1 N N N -19.634 -40.579 -5.112  1.734  -0.253 -0.970 H4  1HQ 32 
1HQ H5  H5  H 0 1 N N N -22.362 -39.879 -7.583  1.052  3.080  -0.075 H5  1HQ 33 
1HQ H6  H6  H 0 1 N N N -21.762 -39.067 -9.891  -1.193 4.040  0.238  H6  1HQ 34 
1HQ H7  H7  H 0 1 N N N -18.123 -40.019 -6.601  -0.661 -0.831 -0.312 H7  1HQ 35 
1HQ H8  H8  H 0 1 N N N -15.569 -39.745 -10.296 -3.242 -0.025 2.165  H8  1HQ 36 
1HQ H9  H9  H 0 1 N N N -17.258 -40.096 -10.797 -4.483 0.991  1.387  H9  1HQ 37 
1HQ H10 H10 H 0 1 N N N -17.451 -41.780 -8.963  -5.519 -1.022 2.424  H10 1HQ 38 
1HQ H11 H11 H 0 1 N N N -16.054 -42.166 -10.025 -5.687 -1.072 0.649  H11 1HQ 39 
1HQ H12 H12 H 0 1 N N N -17.427 -37.542 -10.417 -4.507 1.314  -0.990 H12 1HQ 40 
1HQ H13 H13 H 0 1 N N N -14.207 -41.014 -6.053  -3.204 -4.512 0.722  H13 1HQ 41 
1HQ H14 H14 H 0 1 N N N -14.642 -39.380 -5.677  -2.171 -3.886 -0.446 H14 1HQ 42 
# 
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 
1HQ F18 C15 SING N N 1  
1HQ C20 C21 SING N N 2  
1HQ C20 C19 SING N N 3  
1HQ F27 C25 SING N N 4  
1HQ C25 C19 SING N N 5  
1HQ C25 F26 SING N N 6  
1HQ C15 C14 DOUB Y N 7  
1HQ C15 C16 SING Y N 8  
1HQ C21 O22 SING N N 9  
1HQ C14 C13 SING Y N 10 
1HQ C19 C16 SING N N 11 
1HQ C19 N24 SING N N 12 
1HQ C16 C17 DOUB Y N 13 
1HQ O22 C23 SING N N 14 
1HQ C13 C12 DOUB Y N 15 
1HQ N24 C23 DOUB N N 16 
1HQ C23 N28 SING N N 17 
1HQ C17 C12 SING Y N 18 
1HQ C12 N9  SING N N 19 
1HQ O8  C7  DOUB N N 20 
1HQ N9  C7  SING N N 21 
1HQ C7  C4  SING N N 22 
1HQ C4  C3  DOUB Y N 23 
1HQ C4  N5  SING Y N 24 
1HQ C3  C2  SING Y N 25 
1HQ N5  C6  DOUB Y N 26 
1HQ C2  C1  DOUB Y N 27 
1HQ C6  C1  SING Y N 28 
1HQ C1  C10 SING N N 29 
1HQ C10 N11 TRIP N N 30 
1HQ C2  H1  SING N N 31 
1HQ C3  H2  SING N N 32 
1HQ C6  H3  SING N N 33 
1HQ N9  H4  SING N N 34 
1HQ C13 H5  SING N N 35 
1HQ C14 H6  SING N N 36 
1HQ C17 H7  SING N N 37 
1HQ C20 H8  SING N N 38 
1HQ C20 H9  SING N N 39 
1HQ C21 H10 SING N N 40 
1HQ C21 H11 SING N N 41 
1HQ C25 H12 SING N N 42 
1HQ N28 H13 SING N N 43 
1HQ N28 H14 SING N N 44 
# 
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 
1HQ SMILES           ACDLabs              12.01 "FC(F)C1(N=C(OCC1)N)c3cc(NC(=O)c2ncc(C#N)cc2)ccc3F"                                                                                                            
1HQ InChI            InChI                1.03  "InChI=1S/C18H14F3N5O2/c19-13-3-2-11(25-15(27)14-4-1-10(8-22)9-24-14)7-12(13)18(16(20)21)5-6-28-17(23)26-18/h1-4,7,9,16H,5-6H2,(H2,23,26)(H,25,27)/t18-/m0/s1" 
1HQ InChIKey         InChI                1.03  ZQBDXEARYNLKKR-SFHVURJKSA-N                                                                                                                                    
1HQ SMILES_CANONICAL CACTVS               3.370 "NC1=N[C@](CCO1)(C(F)F)c2cc(NC(=O)c3ccc(cn3)C#N)ccc2F"                                                                                                         
1HQ SMILES           CACTVS               3.370 "NC1=N[C](CCO1)(C(F)F)c2cc(NC(=O)c3ccc(cn3)C#N)ccc2F"                                                                                                          
1HQ SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "c1cc(c(cc1NC(=O)c2ccc(cn2)C#N)[C@@]3(CCOC(=N3)N)C(F)F)F"                                                                                                      
1HQ SMILES           "OpenEye OEToolkits" 1.7.6 "c1cc(c(cc1NC(=O)c2ccc(cn2)C#N)C3(CCOC(=N3)N)C(F)F)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 
1HQ "SYSTEMATIC NAME" ACDLabs              12.01 "N-{3-[(4S)-2-amino-4-(difluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl]-4-fluorophenyl}-5-cyanopyridine-2-carboxamide"          
1HQ "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "N-[3-[(4S)-2-azanyl-4-[bis(fluoranyl)methyl]-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 
1HQ "Create component" 2013-02-07 RCSB 
1HQ "Initial release"  2013-05-01 RCSB 
# 
