data_1A2
# 
_chem_comp.id                                    1A2 
_chem_comp.name                                  "5-(4'-AMINO-1'-ETHYL-5',8'-DIFLUORO-1'H-SPIRO[PIPERIDINE-4,2'-QUINAZOLINE]-1-YLCARBONYL)PICOLINONITRILE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H22 F2 N6 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-12-06 
_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                        412.436 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     1A2 
_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 
1A2 C8   C8   C 0 1 N N N 129.991 113.969 92.388 -2.073 1.565  1.812  C8   1A2 1  
1A2 C5   C5   C 0 1 N N N 126.931 116.210 94.085 -2.539 -0.316 -1.858 C5   1A2 2  
1A2 N6   N6   N 0 1 N N N 127.459 116.562 92.866 -1.677 0.665  -1.727 N6   1A2 3  
1A2 C2   C2   C 0 1 Y N N 126.806 112.115 94.924 -4.226 -1.758 1.761  C2   1A2 4  
1A2 C4   C4   C 0 1 Y N N 125.942 114.300 95.311 -3.723 -2.104 -0.560 C4   1A2 5  
1A2 C1   C1   C 0 1 Y N N 127.760 112.618 94.070 -3.655 -0.500 1.717  C1   1A2 6  
1A2 C3   C3   C 0 1 Y N N 125.898 112.957 95.530 -4.263 -2.557 0.631  C3   1A2 7  
1A2 C4A  C4A  C 0 1 Y N N 126.913 114.851 94.429 -3.144 -0.840 -0.613 C4A  1A2 8  
1A2 C7   C7   C 0 1 N N N 128.014 115.621 91.849 -1.347 1.162  -0.390 C7   1A2 9  
1A2 N8   N8   N 0 1 N N N 128.624 114.518 92.715 -2.539 1.235  0.458  N8   1A2 10 
1A2 C8A  C8A  C 0 1 Y N N 127.846 113.999 93.755 -3.111 -0.027 0.530  C8A  1A2 11 
1A2 F9   F9   F 0 1 N N N 125.067 115.057 95.917 -3.759 -2.883 -1.663 F9   1A2 12 
1A2 F10  F10  F 0 1 N N N 128.622 111.818 93.532 -3.627 0.269  2.828  F10  1A2 13 
1A2 C11  C11  C 0 1 N N N 126.851 115.022 90.995 -0.731 2.560  -0.516 C11  1A2 14 
1A2 C12  C12  C 0 1 N N N 126.245 116.094 90.094 0.498  2.491  -1.427 C12  1A2 15 
1A2 N13  N13  N 0 1 N N N 127.348 116.583 89.206 1.421  1.476  -0.899 N13  1A2 16 
1A2 C14  C14  C 0 1 N N N 128.160 117.446 90.129 0.911  0.122  -0.645 C14  1A2 17 
1A2 C15  C15  C 0 1 N N N 129.011 116.430 90.933 -0.324 0.220  0.255  C15  1A2 18 
1A2 C16  C16  C 0 1 N N N 126.969 117.088 87.938 2.711  1.782  -0.654 C16  1A2 19 
1A2 O17  O17  O 0 1 N N N 125.742 117.105 87.570 3.097  2.930  -0.773 O17  1A2 20 
1A2 N18  N18  N 0 1 N N N 126.478 117.108 94.937 -2.864 -0.833 -3.094 N18  1A2 21 
1A2 C19  C19  C 0 1 N N N 128.021 117.558 87.050 3.646  0.733  -0.243 C19  1A2 22 
1A2 C20  C20  C 0 1 N N N 127.836 118.663 86.122 4.115  -0.151 -1.151 C20  1A2 23 
1A2 N21  N21  N 0 1 N N N 128.959 119.034 85.299 4.949  -1.137 -0.796 N21  1A2 24 
1A2 C22  C22  C 0 1 N N N 130.208 118.334 85.401 5.107  -1.494 0.446  C22  1A2 25 
1A2 C23  C23  C 0 1 N N N 130.359 117.280 86.298 4.317  -0.836 1.548  C23  1A2 26 
1A2 C24  C24  C 0 1 N N N 129.281 116.895 87.111 4.094  0.641  1.195  C24  1A2 27 
1A2 C25  C25  C 0 1 N N N 131.283 118.662 84.629 6.045  -2.527 0.770  C25  1A2 28 
1A2 N26  N26  N 0 1 N N N 132.374 118.939 83.898 6.789  -3.346 1.026  N26  1A2 29 
1A2 C13  C13  C 0 1 N N N 129.992 113.109 91.068 -1.607 3.022  1.850  C13  1A2 30 
1A2 H81  1H8  H 0 1 N N N 130.669 114.822 92.236 -1.244 0.911  2.081  H81  1A2 31 
1A2 H82  2H8  H 0 1 N N N 130.319 113.330 93.221 -2.890 1.426  2.521  H82  1A2 32 
1A2 H2   H2   H 0 1 N N N 126.768 111.054 95.121 -4.648 -2.122 2.686  H2   1A2 33 
1A2 H3   H3   H 0 1 N N N 125.144 112.547 96.185 -4.714 -3.537 0.679  H3   1A2 34 
1A2 H111 1H11 H 0 0 N N N 126.071 114.641 91.671 -1.464 3.244  -0.945 H111 1A2 35 
1A2 H112 2H11 H 0 0 N N N 127.245 114.206 90.371 -0.434 2.917  0.470  H112 1A2 36 
1A2 H121 1H12 H 0 0 N N N 125.823 116.917 90.689 0.190  2.215  -2.435 H121 1A2 37 
1A2 H122 2H12 H 0 0 N N N 125.427 115.672 89.492 0.994  3.461  -1.446 H122 1A2 38 
1A2 H141 1H14 H 0 0 N N N 127.534 118.079 90.776 0.638  -0.348 -1.590 H141 1A2 39 
1A2 H142 2H14 H 0 0 N N N 128.796 118.147 89.568 1.679  -0.470 -0.149 H142 1A2 40 
1A2 H151 1H15 H 0 0 N N N 129.559 115.756 90.258 -0.033 0.612  1.230  H151 1A2 41 
1A2 H152 2H15 H 0 0 N N N 129.755 116.957 91.549 -0.766 -0.769 0.376  H152 1A2 42 
1A2 H181 1H18 H 0 0 N N N 126.107 116.905 95.843 -3.504 -1.558 -3.163 H181 1A2 43 
1A2 H182 2H18 H 0 0 N N N 126.561 118.023 94.541 -2.453 -0.471 -3.894 H182 1A2 44 
1A2 H20  H20  H 0 1 N N N 126.893 119.185 86.053 3.811  -0.060 -2.184 H20  1A2 45 
1A2 H231 1H23 H 0 0 N N N 131.107 117.651 87.014 3.355  -1.338 1.655  H231 1A2 46 
1A2 H232 2H23 H 0 0 N N N 130.617 116.398 85.693 4.871  -0.906 2.484  H232 1A2 47 
1A2 H241 1H24 H 0 0 N N N 129.043 115.889 86.736 5.024  1.193  1.331  H241 1A2 48 
1A2 H242 2H24 H 0 0 N N N 129.632 117.022 88.146 3.322  1.058  1.842  H242 1A2 49 
1A2 H131 1H13 H 0 0 N N N 129.094 112.474 91.044 -1.833 3.450  2.827  H131 1A2 50 
1A2 H132 2H13 H 0 0 N N N 130.890 112.475 91.044 -0.533 3.064  1.674  H132 1A2 51 
1A2 H133 3H13 H 0 0 N N N 129.992 113.777 90.194 -2.125 3.589  1.077  H133 1A2 52 
# 
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 
1A2 C8  N8   SING N N 1  
1A2 C8  C13  SING N N 2  
1A2 C8  H81  SING N N 3  
1A2 C8  H82  SING N N 4  
1A2 C5  N6   DOUB N N 5  
1A2 C5  C4A  SING N N 6  
1A2 C5  N18  SING N N 7  
1A2 N6  C7   SING N N 8  
1A2 C2  C1   SING Y N 9  
1A2 C2  C3   DOUB Y N 10 
1A2 C2  H2   SING N N 11 
1A2 C4  C3   SING Y N 12 
1A2 C4  C4A  DOUB Y N 13 
1A2 C4  F9   SING N N 14 
1A2 C1  C8A  DOUB Y N 15 
1A2 C1  F10  SING N N 16 
1A2 C3  H3   SING N N 17 
1A2 C4A C8A  SING Y N 18 
1A2 C7  N8   SING N N 19 
1A2 C7  C11  SING N N 20 
1A2 C7  C15  SING N N 21 
1A2 N8  C8A  SING N N 22 
1A2 C11 C12  SING N N 23 
1A2 C11 H111 SING N N 24 
1A2 C11 H112 SING N N 25 
1A2 C12 N13  SING N N 26 
1A2 C12 H121 SING N N 27 
1A2 C12 H122 SING N N 28 
1A2 N13 C14  SING N N 29 
1A2 N13 C16  SING N N 30 
1A2 C14 C15  SING N N 31 
1A2 C14 H141 SING N N 32 
1A2 C14 H142 SING N N 33 
1A2 C15 H151 SING N N 34 
1A2 C15 H152 SING N N 35 
1A2 C16 O17  DOUB N N 36 
1A2 C16 C19  SING N N 37 
1A2 N18 H181 SING N N 38 
1A2 N18 H182 SING N N 39 
1A2 C19 C20  DOUB N N 40 
1A2 C19 C24  SING N N 41 
1A2 C20 N21  SING N N 42 
1A2 C20 H20  SING N N 43 
1A2 N21 C22  DOUB N N 44 
1A2 C22 C23  SING N N 45 
1A2 C22 C25  SING N N 46 
1A2 C23 C24  SING N N 47 
1A2 C23 H231 SING N N 48 
1A2 C23 H232 SING N N 49 
1A2 C24 H241 SING N N 50 
1A2 C24 H242 SING N N 51 
1A2 C25 N26  TRIP N N 52 
1A2 C13 H131 SING N N 53 
1A2 C13 H132 SING N N 54 
1A2 C13 H133 SING N N 55 
# 
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 
1A2 SMILES           ACDLabs              10.04 N#CC4=NC=C(C(=O)N3CCC2(N=C(c1c(c(F)ccc1F)N2CC)N)CC3)CC4                                                                                                      
1A2 InChI            InChI                1.02b InChI=1/C21H22F2N6O/c1-2-29-18-16(23)6-5-15(22)17(18)19(25)27-21(29)7-9-28(10-8-21)20(30)13-3-4-14(11-24)26-12-13/h5-6,12H,2-4,7-10H2,1H3,(H2,25,27)/f/h25H2 
1A2 InChIKey         InChI                1.02b QCFIRACCCDFXIP-ZFJUVRDGCB                                                                                                                                    
1A2 SMILES_CANONICAL CACTVS               3.341 CCN1c2c(F)ccc(F)c2C(=NC13CCN(CC3)C(=O)C4=CN=C(CC4)C#N)N                                                                                                      
1A2 SMILES           CACTVS               3.341 CCN1c2c(F)ccc(F)c2C(=NC13CCN(CC3)C(=O)C4=CN=C(CC4)C#N)N                                                                                                      
1A2 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCN1c2c(ccc(c2C(=NC13CCN(CC3)C(=O)C4=CN=C(CC4)C#N)N)F)F                                                                                                      
1A2 SMILES           "OpenEye OEToolkits" 1.5.0 CCN1c2c(ccc(c2C(=NC13CCN(CC3)C(=O)C4=CN=C(CC4)C#N)N)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 
1A2 "SYSTEMATIC NAME" ACDLabs              10.04 "5-[(4'-amino-1'-ethyl-5',8'-difluoro-1H,1'H-spiro[piperidine-4,2'-quinazolin]-1-yl)carbonyl]-3,4-dihydropyridine-2-carbonitrile" 
1A2 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "5-(4'-amino-1'-ethyl-5',8'-difluoro-spiro[piperidine-4,2'-quinazoline]-1-yl)carbonyl-3,4-dihydropyridine-2-carbonitrile"         
# 
