data_LI9
# 
_chem_comp.id                                    LI9 
_chem_comp.name                                  4-(4-FLUOROPHENYL)-1-METHYL-5-(2-{[(1S)-1-PHENYLETHYL]AMINO}PYRIMIDIN-4-YL)-2-PIPERIDIN-4-YL-1,2-DIHYDRO-3H-PYRAZOL-3-ONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C27 H29 F N6 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-03-21 
_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                        472.557 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     LI9 
_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        1YWR 
_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 
LI9 C1   C1   C 0 1 Y N N 5.449  -0.508 18.624 3.244  -3.072 -0.544 C1   LI9 1  
LI9 C2   C2   C 0 1 Y N N 4.565  -0.810 16.006 1.603  -4.249 1.361  C2   LI9 2  
LI9 C3   C3   C 0 1 Y N N 4.182  -1.073 18.382 2.412  -2.280 0.248  C3   LI9 3  
LI9 C4   C4   C 0 1 Y N N 6.285  -0.091 17.586 3.250  -4.442 -0.379 C4   LI9 4  
LI9 C5   C5   C 0 1 Y N N 5.810  -0.257 16.289 2.431  -5.031 0.571  C5   LI9 5  
LI9 C6   C6   C 0 1 Y N N 3.737  -1.224 17.060 1.594  -2.878 1.207  C6   LI9 6  
LI9 C7   C7   C 0 1 Y N N 3.381  -1.479 19.543 2.402  -0.810 0.075  C7   LI9 7  
LI9 F9   F9   F 0 1 N N N 6.599  0.137  15.295 2.440  -6.373 0.729  F9   LI9 8  
LI9 N10  N10  N 0 1 Y N N 2.175  -2.989 20.849 3.075  1.354  0.061  N10  LI9 9  
LI9 C11  C11  C 0 1 N N N 1.480  -4.159 21.375 3.857  2.586  0.190  C11  LI9 10 
LI9 C12  C12  C 0 1 N N N 1.576  -1.634 22.778 0.931  2.409  -0.813 C12  LI9 11 
LI9 C13  C13  C 0 1 Y N N 2.908  -0.868 20.651 1.348  -0.040 -0.379 C13  LI9 12 
LI9 C14  C14  C 0 1 Y N N 3.075  0.531  21.058 0.018  -0.541 -0.784 C14  LI9 13 
LI9 O15  O15  O 0 1 N N N 3.097  -3.803 18.877 4.614  -0.187 0.771  O15  LI9 14 
LI9 C16  C16  C 0 1 Y N N 2.895  -2.902 19.667 3.510  0.113  0.354  C16  LI9 15 
LI9 N17  N17  N 0 1 Y N N 2.178  -1.731 21.466 1.755  1.272  -0.394 N17  LI9 16 
LI9 C18  C18  C 0 1 N N N -0.590 -5.572 21.213 3.990  4.807  1.320  C18  LI9 17 
LI9 C19  C19  C 0 1 N N N 1.536  -6.678 21.496 4.571  4.679  -0.967 C19  LI9 18 
LI9 C20  C20  C 0 1 N N N 2.315  -5.420 21.132 3.849  3.342  -1.142 C20  LI9 19 
LI9 C21  C21  C 0 1 N N N 0.081  -4.277 20.760 3.236  3.477  1.271  C21  LI9 20 
LI9 N22  N22  N 0 1 N N N 0.242  -6.707 20.816 3.869  5.495  0.030  N22  LI9 21 
LI9 N23  N23  N 0 1 Y N N 3.228  0.820  22.359 -1.084 -0.106 -0.174 N23  LI9 22 
LI9 C24  C24  C 0 1 Y N N 3.229  2.809  20.514 -1.372 -1.915 -2.162 C24  LI9 23 
LI9 N25  N25  N 0 1 N N N 3.537  2.465  23.989 -3.399 -0.090 0.126  N25  LI9 24 
LI9 C26  C26  C 0 1 Y N N 3.069  1.514  20.085 -0.104 -1.475 -1.818 C26  LI9 25 
LI9 C27  C27  C 0 1 Y N N 3.378  2.105  22.689 -2.275 -0.558 -0.532 C27  LI9 26 
LI9 N28  N28  N 0 1 Y N N 3.384  3.114  21.813 -2.420 -1.443 -1.508 N28  LI9 27 
LI9 C29  C29  C 0 1 N N S 3.445  1.565  25.099 -4.727 -0.573 -0.258 C29  LI9 28 
LI9 C30  C30  C 0 1 Y N N 2.105  0.886  25.292 -5.763 0.457  0.114  C30  LI9 29 
LI9 C31  C31  C 0 1 N N N 3.796  2.306  26.405 -5.025 -1.883 0.473  C31  LI9 30 
LI9 C32  C32  C 0 1 Y N N -0.327 -0.429 25.695 -7.664 2.345  0.797  C32  LI9 31 
LI9 C33  C33  C 0 1 Y N N 2.063  -0.309 26.029 -6.817 0.717  -0.742 C33  LI9 32 
LI9 C34  C34  C 0 1 Y N N 0.918  1.403  24.767 -5.662 1.137  1.313  C34  LI9 33 
LI9 C35  C35  C 0 1 Y N N -0.299 0.750  24.965 -6.610 2.084  1.653  C35  LI9 34 
LI9 C36  C36  C 0 1 Y N N 0.846  -0.952 26.222 -7.768 1.661  -0.400 C36  LI9 35 
LI9 H1   H1   H 0 1 N N N 5.798  -0.387 19.663 3.882  -2.614 -1.285 H1   LI9 36 
LI9 H2   H2   H 0 1 N N N 4.238  -0.918 14.958 0.967  -4.713 2.100  H2   LI9 37 
LI9 H4   H4   H 0 1 N N N 7.276  0.350  17.781 3.893  -5.056 -0.992 H4   LI9 38 
LI9 H6   H6   H 0 1 N N N 2.747  -1.663 16.851 0.949  -2.269 1.823  H6   LI9 39 
LI9 H11  H11  H 0 1 N N N 1.349  -4.041 22.476 4.883  2.340  0.464  H11  LI9 40 
LI9 H121 1H12 H 0 0 N N N 1.578  -0.632 23.269 1.117  2.623  -1.865 H121 LI9 41 
LI9 H122 2H12 H 0 0 N N N 0.531  -2.022 22.735 -0.122 2.167  -0.671 H122 LI9 42 
LI9 H123 3H12 H 0 0 N N N 2.048  -2.380 23.458 1.187  3.283  -0.214 H123 LI9 43 
LI9 H181 1H18 H 0 0 N N N -0.815 -5.573 22.305 5.043  4.620  1.534  H181 LI9 44 
LI9 H182 2H18 H 0 0 N N N -1.635 -5.661 20.837 3.568  5.434  2.106  H182 LI9 45 
LI9 H191 1H19 H 0 0 N N N 2.127  -7.601 21.294 5.593  4.499  -0.633 H191 LI9 46 
LI9 H192 2H19 H 0 0 N N N 1.423  -6.787 22.599 4.590  5.209  -1.919 H192 LI9 47 
LI9 H201 1H20 H 0 0 N N N 2.696  -5.463 20.085 4.361  2.749  -1.900 H201 LI9 48 
LI9 H202 2H20 H 0 0 N N N 3.291  -5.373 21.668 2.820  3.522  -1.452 H202 LI9 49 
LI9 H211 1H21 H 0 0 N N N -0.547 -3.383 20.982 2.189  3.661  1.033  H211 LI9 50 
LI9 H212 2H21 H 0 0 N N N 0.106  -4.188 19.648 3.310  2.981  2.238  H212 LI9 51 
LI9 H22  H22  H 0 1 N N N 0.351  -6.755 19.803 4.384  6.359  0.113  H22  LI9 52 
LI9 H24  H24  H 0 1 N N N 3.233  3.637  19.785 -1.503 -2.637 -2.955 H24  LI9 53 
LI9 H25  H25  H 0 1 N N N 2.879  3.224  24.168 -3.307 0.558  0.842  H25  LI9 54 
LI9 H26  H26  H 0 1 N N N 2.942  1.276  19.015 0.769  -1.845 -2.336 H26  LI9 55 
LI9 H29  H29  H 0 1 N N N 4.171  0.755  24.854 -4.754 -0.743 -1.335 H29  LI9 56 
LI9 H311 1H31 H 0 0 N N N 3.724  1.605  27.269 -4.998 -1.713 1.549  H311 LI9 57 
LI9 H312 2H31 H 0 0 N N N 4.792  2.802  26.349 -6.013 -2.243 0.186  H312 LI9 58 
LI9 H313 3H31 H 0 0 N N N 3.169  3.216  26.551 -4.276 -2.628 0.203  H313 LI9 59 
LI9 H32  H32  H 0 1 N N N -1.284 -0.952 25.856 -8.406 3.083  1.063  H32  LI9 60 
LI9 H33  H33  H 0 1 N N N 2.983  -0.741 26.455 -6.899 0.183  -1.677 H33  LI9 61 
LI9 H34  H34  H 0 1 N N N 0.942  2.341  24.187 -4.839 0.933  1.982  H34  LI9 62 
LI9 H35  H35  H 0 1 N N N -1.232 1.163  24.547 -6.529 2.618  2.588  H35  LI9 63 
LI9 H36  H36  H 0 1 N N N 0.810  -1.890 26.801 -8.591 1.865  -1.069 H36  LI9 64 
# 
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 
LI9 C1  C3   DOUB Y N 1  
LI9 C1  C4   SING Y N 2  
LI9 C1  H1   SING N N 3  
LI9 C2  C5   SING Y N 4  
LI9 C2  C6   DOUB Y N 5  
LI9 C2  H2   SING N N 6  
LI9 C3  C6   SING Y N 7  
LI9 C3  C7   SING N N 8  
LI9 C4  C5   DOUB Y N 9  
LI9 C4  H4   SING N N 10 
LI9 C5  F9   SING N N 11 
LI9 C6  H6   SING N N 12 
LI9 C7  C13  DOUB Y N 13 
LI9 C7  C16  SING Y N 14 
LI9 N10 C11  SING N N 15 
LI9 N10 C16  SING Y N 16 
LI9 N10 N17  SING Y N 17 
LI9 C11 C20  SING N N 18 
LI9 C11 C21  SING N N 19 
LI9 C11 H11  SING N N 20 
LI9 C12 N17  SING N N 21 
LI9 C12 H121 SING N N 22 
LI9 C12 H122 SING N N 23 
LI9 C12 H123 SING N N 24 
LI9 C13 C14  SING N N 25 
LI9 C13 N17  SING Y N 26 
LI9 C14 N23  DOUB Y N 27 
LI9 C14 C26  SING Y N 28 
LI9 O15 C16  DOUB N N 29 
LI9 C18 C21  SING N N 30 
LI9 C18 N22  SING N N 31 
LI9 C18 H181 SING N N 32 
LI9 C18 H182 SING N N 33 
LI9 C19 C20  SING N N 34 
LI9 C19 N22  SING N N 35 
LI9 C19 H191 SING N N 36 
LI9 C19 H192 SING N N 37 
LI9 C20 H201 SING N N 38 
LI9 C20 H202 SING N N 39 
LI9 C21 H211 SING N N 40 
LI9 C21 H212 SING N N 41 
LI9 N22 H22  SING N N 42 
LI9 N23 C27  SING Y N 43 
LI9 C24 C26  DOUB Y N 44 
LI9 C24 N28  SING Y N 45 
LI9 C24 H24  SING N N 46 
LI9 N25 C27  SING N N 47 
LI9 N25 C29  SING N N 48 
LI9 N25 H25  SING N N 49 
LI9 C26 H26  SING N N 50 
LI9 C27 N28  DOUB Y N 51 
LI9 C29 C30  SING N N 52 
LI9 C29 C31  SING N N 53 
LI9 C29 H29  SING N N 54 
LI9 C30 C33  DOUB Y N 55 
LI9 C30 C34  SING Y N 56 
LI9 C31 H311 SING N N 57 
LI9 C31 H312 SING N N 58 
LI9 C31 H313 SING N N 59 
LI9 C32 C35  SING Y N 60 
LI9 C32 C36  DOUB Y N 61 
LI9 C32 H32  SING N N 62 
LI9 C33 C36  SING Y N 63 
LI9 C33 H33  SING N N 64 
LI9 C34 C35  DOUB Y N 65 
LI9 C34 H34  SING N N 66 
LI9 C35 H35  SING N N 67 
LI9 C36 H36  SING N N 68 
# 
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 
LI9 SMILES           ACDLabs              10.04 Fc1ccc(cc1)C2=C(N(N(C2=O)C3CCNCC3)C)c4nc(ncc4)NC(c5ccccc5)C                                                                                                                                                 
LI9 InChI            InChI                1.02b InChI=1/C27H29FN6O/c1-18(19-6-4-3-5-7-19)31-27-30-17-14-23(32-27)25-24(20-8-10-21(28)11-9-20)26(35)34(33(25)2)22-12-15-29-16-13-22/h3-11,14,17-18,22,29H,12-13,15-16H2,1-2H3,(H,30,31,32)/t18-/m0/s1/f/h31H 
LI9 InChIKey         InChI                1.02b OYTOWRNFVUUVHK-BEBFFCOCDB                                                                                                                                                                                   
LI9 SMILES_CANONICAL CACTVS               3.341 C[C@H](Nc1nccc(n1)C2=C(C(=O)N(C3CCNCC3)N2C)c4ccc(F)cc4)c5ccccc5                                                                                                                                             
LI9 SMILES           CACTVS               3.341 C[CH](Nc1nccc(n1)C2=C(C(=O)N(C3CCNCC3)N2C)c4ccc(F)cc4)c5ccccc5                                                                                                                                              
LI9 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@@H](c1ccccc1)Nc2nccc(n2)C3=C(C(=O)N(N3C)C4CCNCC4)c5ccc(cc5)F                                                                                                                                            
LI9 SMILES           "OpenEye OEToolkits" 1.5.0 CC(c1ccccc1)Nc2nccc(n2)C3=C(C(=O)N(N3C)C4CCNCC4)c5ccc(cc5)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 
LI9 "SYSTEMATIC NAME" ACDLabs              10.04 4-(4-fluorophenyl)-1-methyl-5-(2-{[(1S)-1-phenylethyl]amino}pyrimidin-4-yl)-2-piperidin-4-yl-1,2-dihydro-3H-pyrazol-3-one 
LI9 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 4-(4-fluorophenyl)-1-methyl-5-[2-[[(1S)-1-phenylethyl]amino]pyrimidin-4-yl]-2-piperidin-4-yl-pyrazol-3-one                
# 
