data_LIA
# 
_chem_comp.id                                    LIA 
_chem_comp.name                                  (4-AMINO-2-{[1-(METHYLSULFONYL)PIPERIDIN-4-YL]AMINO}PYRIMIDIN-5-YL)(2,3-DIFLUORO-6-METHOXYPHENYL)METHANONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C18 H21 F2 N5 O4 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-02-03 
_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                        441.452 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     LIA 
_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        2FVD 
_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 
LIA N1   N1   N 0 1 N N N 6.006  26.497 6.980  -5.407 0.029  0.563  N1   LIA 1  
LIA C2   C2   C 0 1 N N N 5.228  26.235 5.737  -5.276 1.443  0.189  C2   LIA 2  
LIA C3   C3   C 0 1 N N N 4.425  27.497 5.356  -4.148 1.580  -0.838 C3   LIA 3  
LIA C4   C4   C 0 1 N N N 3.474  27.912 6.508  -2.869 0.959  -0.270 C4   LIA 4  
LIA C5   C5   C 0 1 N N N 4.263  28.022 7.859  -3.100 -0.530 -0.001 C5   LIA 5  
LIA C6   C6   C 0 1 N N N 5.084  26.743 8.129  -4.216 -0.690 1.036  C6   LIA 6  
LIA N7   N7   N 0 1 N N N 2.853  29.193 6.145  -1.780 1.117  -1.237 N7   LIA 7  
LIA C8   C8   C 0 1 Y N N 1.769  29.532 6.900  -0.470 1.126  -0.804 C8   LIA 8  
LIA N9   N9   N 0 1 Y N N 1.069  28.596 7.597  -0.221 0.991  0.494  N9   LIA 9  
LIA C10  C10  C 0 1 Y N N 0.049  28.949 8.317  1.016  0.994  0.955  C10  LIA 10 
LIA C11  C11  C 0 1 Y N N -0.400 30.325 8.422  2.078  1.144  0.054  C11  LIA 11 
LIA C12  C12  C 0 1 Y N N 0.364  31.287 7.659  1.772  1.291  -1.317 C12  LIA 12 
LIA N13  N13  N 0 1 Y N N 1.437  30.856 6.914  0.499  1.271  -1.695 N13  LIA 13 
LIA C14  C14  C 0 1 N N N -1.543 30.655 9.260  3.472  1.153  0.524  C14  LIA 14 
LIA O15  O15  O 0 1 N N N -1.970 31.821 9.319  3.922  2.140  1.076  O15  LIA 15 
LIA C16  C16  C 0 1 Y N N -2.197 29.647 10.064 4.325  -0.033 0.325  C16  LIA 16 
LIA C17  C17  C 0 1 Y N N -3.548 29.259 9.750  3.782  -1.209 -0.206 C17  LIA 17 
LIA C18  C18  C 0 1 Y N N -4.212 28.257 10.524 4.589  -2.317 -0.388 C18  LIA 18 
LIA C19  C19  C 0 1 Y N N -3.548 27.625 11.616 5.933  -2.265 -0.051 C19  LIA 19 
LIA C20  C20  C 0 1 Y N N -2.214 27.992 11.950 6.479  -1.107 0.469  C20  LIA 20 
LIA C21  C21  C 0 1 Y N N -1.510 29.004 11.189 5.686  0.013  0.658  C21  LIA 21 
LIA O22  O22  O 0 1 N N N -0.188 29.401 11.490 6.224  1.150  1.168  O22  LIA 22 
LIA C23  C23  C 0 1 N N N 0.555  28.398 12.227 7.607  0.881  1.406  C23  LIA 23 
LIA F24  F24  F 0 1 N N N -4.202 29.825 8.740  2.473  -1.264 -0.534 F24  LIA 24 
LIA F25  F25  F 0 1 N N N -5.450 27.907 10.229 4.066  -3.455 -0.896 F25  LIA 25 
LIA N26  N26  N 0 1 N N N 0.083  32.603 7.639  2.778  1.442  -2.248 N26  LIA 26 
LIA S27  S27  S 0 1 N N N 7.063  25.211 7.310  -6.869 -0.741 0.454  S27  LIA 27 
LIA C28  C28  C 0 1 N N N 6.179  23.662 7.710  -6.861 -1.406 -1.234 C28  LIA 28 
LIA O29  O29  O 0 1 N N N 7.871  25.586 8.449  -6.755 -1.773 1.424  O29  LIA 29 
LIA O30  O30  O 0 1 N N N 7.911  25.002 6.168  -7.798 0.326  0.592  O30  LIA 30 
LIA H21  1H2  H 0 1 N N N 4.535  25.398 5.908  -5.039 2.035  1.074  H21  LIA 31 
LIA H22  2H2  H 0 1 N N N 5.918  25.979 4.920  -6.212 1.794  -0.247 H22  LIA 32 
LIA H31  1H3  H 0 1 N N N 3.823  27.276 4.462  -3.976 2.635  -1.051 H31  LIA 33 
LIA H32  2H3  H 0 1 N N N 5.125  28.321 5.154  -4.427 1.063  -1.756 H32  LIA 34 
LIA H4   H4   H 0 1 N N N 2.692  27.152 6.653  -2.605 1.460  0.661  H4   LIA 35 
LIA H51  1H5  H 0 1 N N N 3.540  28.153 8.677  -3.389 -1.027 -0.927 H51  LIA 36 
LIA H52  2H5  H 0 1 N N N 4.948  28.881 7.803  -2.182 -0.977 0.381  H52  LIA 37 
LIA H61  1H6  H 0 1 N N N 5.670  26.869 9.051  -3.892 -0.273 1.989  H61  LIA 38 
LIA H62  2H6  H 0 1 N N N 4.403  25.887 8.244  -4.452 -1.747 1.158  H62  LIA 39 
LIA HN7  HN7  H 0 1 N N N 3.197  29.770 5.404  -1.979 1.215  -2.181 HN7  LIA 40 
LIA H10  H10  H 0 1 N N N -0.489 28.187 8.861  1.207  0.883  2.012  H10  LIA 41 
LIA H19  H19  H 0 1 N N N -4.058 26.866 12.191 6.556  -3.135 -0.196 H19  LIA 42 
LIA H20  H20  H 0 1 N N N -1.720 27.510 12.781 7.527  -1.076 0.728  H20  LIA 43 
LIA H231 1H23 H 0 0 N N N -0.029 28.080 13.104 7.701  0.057  2.114  H231 LIA 44 
LIA H232 2H23 H 0 0 N N N 1.514  28.822 12.559 8.092  0.611  0.468  H232 LIA 45 
LIA H233 3H23 H 0 0 N N N 0.743  27.530 11.578 8.084  1.770  1.819  H233 LIA 46 
LIA H261 1H26 H 0 0 N N N 0.585  33.301 7.128  2.557  1.606  -3.178 H261 LIA 47 
LIA H262 2H26 H 0 0 N N N -0.713 32.765 8.222  3.706  1.383  -1.973 H262 LIA 48 
LIA H281 1H28 H 0 0 N N N 5.216  23.902 8.183  -6.020 -2.089 -1.351 H281 LIA 49 
LIA H282 2H28 H 0 0 N N N 6.788  23.060 8.401  -7.793 -1.942 -1.418 H282 LIA 50 
LIA H283 3H28 H 0 0 N N N 6.001  23.092 6.786  -6.766 -0.587 -1.947 H283 LIA 51 
# 
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 
LIA N1  C2   SING N N 1  
LIA N1  C6   SING N N 2  
LIA N1  S27  SING N N 3  
LIA C2  C3   SING N N 4  
LIA C2  H21  SING N N 5  
LIA C2  H22  SING N N 6  
LIA C3  C4   SING N N 7  
LIA C3  H31  SING N N 8  
LIA C3  H32  SING N N 9  
LIA C4  C5   SING N N 10 
LIA C4  N7   SING N N 11 
LIA C4  H4   SING N N 12 
LIA C5  C6   SING N N 13 
LIA C5  H51  SING N N 14 
LIA C5  H52  SING N N 15 
LIA C6  H61  SING N N 16 
LIA C6  H62  SING N N 17 
LIA N7  C8   SING N N 18 
LIA N7  HN7  SING N N 19 
LIA C8  N9   DOUB Y N 20 
LIA C8  N13  SING Y N 21 
LIA N9  C10  SING Y N 22 
LIA C10 C11  DOUB Y N 23 
LIA C10 H10  SING N N 24 
LIA C11 C12  SING Y N 25 
LIA C11 C14  SING N N 26 
LIA C12 N13  DOUB Y N 27 
LIA C12 N26  SING N N 28 
LIA C14 O15  DOUB N N 29 
LIA C14 C16  SING N N 30 
LIA C16 C17  SING Y N 31 
LIA C16 C21  DOUB Y N 32 
LIA C17 C18  DOUB Y N 33 
LIA C17 F24  SING N N 34 
LIA C18 C19  SING Y N 35 
LIA C18 F25  SING N N 36 
LIA C19 C20  DOUB Y N 37 
LIA C19 H19  SING N N 38 
LIA C20 C21  SING Y N 39 
LIA C20 H20  SING N N 40 
LIA C21 O22  SING N N 41 
LIA O22 C23  SING N N 42 
LIA C23 H231 SING N N 43 
LIA C23 H232 SING N N 44 
LIA C23 H233 SING N N 45 
LIA N26 H261 SING N N 46 
LIA N26 H262 SING N N 47 
LIA S27 C28  SING N N 48 
LIA S27 O29  DOUB N N 49 
LIA S27 O30  DOUB N N 50 
LIA C28 H281 SING N N 51 
LIA C28 H282 SING N N 52 
LIA C28 H283 SING N N 53 
# 
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 
LIA SMILES           ACDLabs              10.04 O=S(=O)(N3CCC(Nc2nc(N)c(C(=O)c1c(F)c(F)ccc1OC)cn2)CC3)C                                                                                                              
LIA InChI            InChI                1.02b InChI=1/C18H21F2N5O4S/c1-29-13-4-3-12(19)15(20)14(13)16(26)11-9-22-18(24-17(11)21)23-10-5-7-25(8-6-10)30(2,27)28/h3-4,9-10H,5-8H2,1-2H3,(H3,21,22,23,24)/f/h23H,21H2 
LIA InChIKey         InChI                1.02b JRNJNYBQQYBCLE-VDDAFCAXCQ                                                                                                                                            
LIA SMILES_CANONICAL CACTVS               3.341 COc1ccc(F)c(F)c1C(=O)c2cnc(NC3CCN(CC3)[S](C)(=O)=O)nc2N                                                                                                              
LIA SMILES           CACTVS               3.341 COc1ccc(F)c(F)c1C(=O)c2cnc(NC3CCN(CC3)[S](C)(=O)=O)nc2N                                                                                                              
LIA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 COc1ccc(c(c1C(=O)c2cnc(nc2N)NC3CCN(CC3)S(=O)(=O)C)F)F                                                                                                                
LIA SMILES           "OpenEye OEToolkits" 1.5.0 COc1ccc(c(c1C(=O)c2cnc(nc2N)NC3CCN(CC3)S(=O)(=O)C)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 
LIA "SYSTEMATIC NAME" ACDLabs              10.04 (4-amino-2-{[1-(methylsulfonyl)piperidin-4-yl]amino}pyrimidin-5-yl)(2,3-difluoro-6-methoxyphenyl)methanone 
LIA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 [4-amino-2-[(1-methylsulfonylpiperidin-4-yl)amino]pyrimidin-5-yl]-(2,3-difluoro-6-methoxy-phenyl)methanone 
# 
