data_B14
# 
_chem_comp.id                                    B14 
_chem_comp.name                                  "1-(6-CYANO-3-PYRIDYLCARBONYL)-5',8'-DIFLUOROSPIRO[PIPERIDINE-4,2'(1'H)-QUINAZOLINE]-4'-AMINE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H16 F2 N6 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         AR-C102222 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-10-03 
_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                        382.367 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     B14 
_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        ? 
_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 
B14 C1   C1   C 0 1 Y N N 128.118 112.722 93.958 -4.285 -1.821 0.413  C1   B14 1  
B14 C2   C2   C 0 1 Y N N 127.276 112.145 94.893 -5.515 -1.537 -0.152 C2   B14 2  
B14 C3   C3   C 0 1 Y N N 126.300 112.907 95.541 -5.860 -0.237 -0.478 C3   B14 3  
B14 C4   C4   C 0 1 Y N N 126.166 114.266 95.280 -4.973 0.799  -0.245 C4   B14 4  
B14 C4A  C4A  C 0 1 Y N N 127.057 114.889 94.348 -3.732 0.523  0.327  C4A  B14 5  
B14 C5   C5   C 0 1 N N N 127.035 116.274 93.990 -2.743 1.594  0.582  C5   B14 6  
B14 N6   N6   N 0 1 N N N 127.547 116.641 92.795 -1.493 1.221  0.719  N6   B14 7  
B14 C7   C7   C 0 1 N N N 128.141 115.705 91.798 -1.144 -0.195 0.586  C7   B14 8  
B14 N8   N8   N 0 1 N N N 128.756 114.678 92.687 -2.144 -1.050 1.230  N8   B14 9  
B14 C8A  C8A  C 0 1 Y N N 128.018 114.102 93.644 -3.382 -0.793 0.657  C8A  B14 10 
B14 F9   F9   F 0 1 N N N 125.244 114.934 95.887 -5.309 2.068  -0.564 F9   B14 11 
B14 F10  F10  F 0 1 N N N 129.015 112.019 93.350 -3.962 -3.094 0.726  F10  B14 12 
B14 C11  C11  C 0 1 N N N 127.032 115.051 90.908 -1.059 -0.551 -0.903 C11  B14 13 
B14 C12  C12  C 0 1 N N N 126.440 116.105 89.980 -0.035 0.362  -1.582 C12  B14 14 
B14 N13  N13  N 0 1 N N N 127.553 116.601 89.120 1.244  0.254  -0.867 N13  B14 15 
B14 C14  C14  C 0 1 N N N 128.332 117.467 90.061 1.262  0.478  0.585  C14  B14 16 
B14 C15  C15  C 0 1 N N N 129.159 116.499 90.929 0.222  -0.437 1.238  C15  B14 17 
B14 C16  C16  C 0 1 N N N 127.199 117.101 87.865 2.379  -0.045 -1.530 C16  B14 18 
B14 O17  O17  O 0 1 N N N 126.013 117.119 87.486 2.335  -0.342 -2.708 O17  B14 19 
B14 N18  N18  N 0 1 N N N 126.568 117.196 94.777 -3.118 2.917  0.677  N18  B14 20 
B14 C19  C19  C 0 1 Y N N 128.225 117.581 86.977 3.678  -0.012 -0.824 C19  B14 21 
B14 C20  C20  C 0 1 Y N N 128.002 118.718 86.125 4.639  -0.998 -1.063 C20  B14 22 
B14 N21  N21  N 0 1 Y N N 129.074 119.163 85.317 5.798  -0.970 -0.443 N21  B14 23 
B14 C22  C22  C 0 1 Y N N 130.311 118.524 85.339 6.098  -0.021 0.436  C22  B14 24 
B14 C23  C23  C 0 1 Y N N 130.522 117.424 86.156 5.188  0.994  0.731  C23  B14 25 
B14 C24  C24  C 0 1 Y N N 129.486 116.950 86.971 3.960  1.005  0.096  C24  B14 26 
B14 C25  C25  C 0 1 N N N 131.321 118.979 84.552 7.373  -0.040 1.089  C25  B14 27 
B14 N26  N26  N 0 1 N N N 132.327 119.410 83.795 8.384  -0.055 1.607  N26  B14 28 
B14 H2   H2   H 0 1 N N N 127.374 111.095 95.124 -6.214 -2.339 -0.340 H2   B14 29 
B14 H3   H3   H 0 1 N N N 125.641 112.434 96.254 -6.826 -0.030 -0.916 H3   B14 30 
B14 HN8  HN8  H 0 1 N N N 129.063 113.938 92.088 -1.907 -2.002 0.993  HN8  B14 31 
B14 H111 1H11 H 0 0 N N N 126.239 114.641 91.551 -0.749 -1.590 -1.011 H111 B14 32 
B14 H112 2H11 H 0 0 N N N 127.473 114.241 90.309 -2.036 -0.411 -1.367 H112 B14 33 
B14 H121 1H12 H 0 0 N N N 125.993 116.928 90.556 0.099  0.053  -2.619 H121 B14 34 
B14 H122 2H12 H 0 0 N N N 125.645 115.665 89.360 -0.385 1.394  -1.549 H122 B14 35 
B14 H141 1H14 H 0 0 N N N 127.670 118.096 90.674 2.252  0.245  0.978  H141 B14 36 
B14 H142 2H14 H 0 0 N N N 128.990 118.152 89.506 1.018  1.519  0.797  H142 B14 37 
B14 H151 1H15 H 0 0 N N N 129.760 115.822 90.305 0.161  -0.215 2.304  H151 B14 38 
B14 H152 2H15 H 0 0 N N N 129.858 117.057 91.569 0.513  -1.478 1.098  H152 B14 39 
B14 H181 1H18 H 0 0 N N N 126.542 118.175 94.575 -2.451 3.599  0.849  H181 B14 40 
B14 H182 2H18 H 0 0 N N N 126.239 116.766 95.618 -4.049 3.166  0.568  H182 B14 41 
B14 H20  H20  H 0 1 N N N 127.044 119.217 86.103 4.431  -1.786 -1.771 H20  B14 42 
B14 H23  H23  H 0 1 N N N 131.484 116.933 86.164 5.440  1.763  1.446  H23  B14 43 
B14 H24  H24  H 0 1 N N N 129.655 116.090 87.603 3.236  1.779  0.304  H24  B14 44 
# 
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 
B14 C1  C2   SING Y N 1  
B14 C1  C8A  DOUB Y N 2  
B14 C1  F10  SING N N 3  
B14 C2  C3   DOUB Y N 4  
B14 C2  H2   SING N N 5  
B14 C3  C4   SING Y N 6  
B14 C3  H3   SING N N 7  
B14 C4  C4A  DOUB Y N 8  
B14 C4  F9   SING N N 9  
B14 C4A C5   SING N N 10 
B14 C4A C8A  SING Y N 11 
B14 C5  N6   DOUB N N 12 
B14 C5  N18  SING N N 13 
B14 N6  C7   SING N N 14 
B14 C7  N8   SING N N 15 
B14 C7  C11  SING N N 16 
B14 C7  C15  SING N N 17 
B14 N8  C8A  SING N N 18 
B14 N8  HN8  SING N N 19 
B14 C11 C12  SING N N 20 
B14 C11 H111 SING N N 21 
B14 C11 H112 SING N N 22 
B14 C12 N13  SING N N 23 
B14 C12 H121 SING N N 24 
B14 C12 H122 SING N N 25 
B14 N13 C14  SING N N 26 
B14 N13 C16  SING N N 27 
B14 C14 C15  SING N N 28 
B14 C14 H141 SING N N 29 
B14 C14 H142 SING N N 30 
B14 C15 H151 SING N N 31 
B14 C15 H152 SING N N 32 
B14 C16 O17  DOUB N N 33 
B14 C16 C19  SING N N 34 
B14 N18 H181 SING N N 35 
B14 N18 H182 SING N N 36 
B14 C19 C20  SING Y N 37 
B14 C19 C24  DOUB Y N 38 
B14 C20 N21  DOUB Y N 39 
B14 C20 H20  SING N N 40 
B14 N21 C22  SING Y N 41 
B14 C22 C23  DOUB Y N 42 
B14 C22 C25  SING N N 43 
B14 C23 C24  SING Y N 44 
B14 C23 H23  SING N N 45 
B14 C24 H24  SING N N 46 
B14 C25 N26  TRIP 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 
B14 SMILES           ACDLabs              10.04 N#Cc1ncc(cc1)C(=O)N4CCC3(N=C(c2c(c(F)ccc2F)N3)N)CC4                                                                                              
B14 InChI            InChI                1.02b InChI=1/C19H16F2N6O/c20-13-3-4-14(21)16-15(13)17(23)26-19(25-16)5-7-27(8-6-19)18(28)11-1-2-12(9-22)24-10-11/h1-4,10,25H,5-8H2,(H2,23,26)/f/h23H2 
B14 InChIKey         InChI                1.02b GIZYIOOBBUHOBS-TWSYTRIPCU                                                                                                                        
B14 SMILES_CANONICAL CACTVS               3.341 NC1=NC2(CCN(CC2)C(=O)c3ccc(nc3)C#N)Nc4c(F)ccc(F)c14                                                                                              
B14 SMILES           CACTVS               3.341 NC1=NC2(CCN(CC2)C(=O)c3ccc(nc3)C#N)Nc4c(F)ccc(F)c14                                                                                              
B14 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(ncc1C(=O)N2CCC3(CC2)Nc4c(ccc(c4C(=N3)N)F)F)C#N                                                                                              
B14 SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(ncc1C(=O)N2CCC3(CC2)Nc4c(ccc(c4C(=N3)N)F)F)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 
B14 "SYSTEMATIC NAME" ACDLabs              10.04 "5-[(4'-amino-5',8'-difluoro-1H,1'H-spiro[piperidine-4,2'-quinazolin]-1-yl)carbonyl]pyridine-2-carbonitrile" 
B14 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "5-(4-amino-5,8-difluoro-spiro[1H-quinazoline-2,4'-piperidine]-1'-yl)carbonylpyridine-2-carbonitrile"        
# 
