data_JAN
# 
_chem_comp.id                                    JAN 
_chem_comp.name                                  6-[(S)-AMINO(4-CHLOROPHENYL)(1-METHYL-1H-IMIDAZOL-5-YL)METHYL]-4-(3-CHLOROPHENYL)-1-METHYLQUINOLIN-2(1H)-ONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C27 H22 Cl2 N4 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "R115777; TIPIFARNIB" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-02-18 
_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                        489.396 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     JAN 
_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        1SA4 
_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 
JAN C1   C1   C  0 1 N N N 21.297 132.372 0.705  2.844  -3.043 0.785  C1   JAN 1  
JAN N1   N1   N  0 1 Y N N 20.244 132.726 1.692  2.761  -2.353 2.074  N1   JAN 2  
JAN C2   C2   C  0 1 Y N N 20.019 132.084 2.837  3.620  -2.481 3.109  C2   JAN 3  
JAN N2   N2   N  0 1 Y N N 18.969 132.698 3.444  3.219  -1.711 4.083  N2   JAN 4  
JAN C3   C3   C  0 1 Y N N 18.549 133.720 2.669  2.101  -1.071 3.710  C3   JAN 5  
JAN C4   C4   C  0 1 Y N N 19.355 133.698 1.615  1.801  -1.454 2.454  C4   JAN 6  
JAN C5   C5   C  0 1 N N R 19.210 134.577 0.472  0.629  -0.989 1.628  C5   JAN 7  
JAN C6   C6   C  0 1 Y N N 18.920 133.862 -0.735 -0.252 -0.098 2.465  C6   JAN 8  
JAN C7   C7   C  0 1 Y N N 17.922 132.855 -0.740 -1.284 -0.644 3.204  C7   JAN 9  
JAN C8   C8   C  0 1 Y N N 17.586 132.186 -1.925 -2.093 0.172  3.971  C8   JAN 10 
JAN C9   C9   C  0 1 Y N N 18.236 132.507 -3.124 -1.869 1.537  4.000  C9   JAN 11 
JAN CL1  CL1  CL 0 0 N N N 17.761 131.677 -4.625 -2.884 2.563  4.964  CL1  JAN 12 
JAN C10  C10  C  0 1 Y N N 19.236 133.502 -3.142 -0.835 2.083  3.261  C10  JAN 13 
JAN C11  C11  C  0 1 Y N N 19.579 134.179 -1.950 -0.023 1.264  2.498  C11  JAN 14 
JAN N3   N3   N  0 1 N N N 20.548 135.175 0.286  -0.142 -2.154 1.174  N3   JAN 15 
JAN C12  C12  C  0 1 Y N N 18.357 135.721 0.698  1.130  -0.221 0.433  C12  JAN 16 
JAN C13  C13  C  0 1 Y N N 17.179 135.935 -0.075 0.456  -0.299 -0.753 C13  JAN 17 
JAN C14  C14  C  0 1 Y N N 16.235 136.936 0.285  0.916  0.416  -1.860 C14  JAN 18 
JAN C15  C15  C  0 1 Y N N 18.591 136.556 1.820  2.274  0.555  0.543  C15  JAN 19 
JAN C16  C16  C  0 1 Y N N 17.664 137.545 2.184  2.749  1.266  -0.537 C16  JAN 20 
JAN C17  C17  C  0 1 Y N N 16.482 137.736 1.436  2.075  1.204  -1.753 C17  JAN 21 
JAN N4   N4   N  0 1 Y N N 15.500 138.687 1.862  2.528  1.906  -2.851 N4   JAN 22 
JAN C18  C18  C  0 1 N N N 15.736 139.547 3.058  3.737  2.725  -2.732 C18  JAN 23 
JAN C19  C19  C  0 1 Y N N 14.291 138.827 1.145  1.882  1.852  -4.027 C19  JAN 24 
JAN O1   O1   O  0 1 N N N 13.425 139.609 1.538  2.316  2.487  -4.973 O1   JAN 25 
JAN C20  C20  C  0 1 Y N N 14.060 138.051 0.005  0.717  1.081  -4.199 C20  JAN 26 
JAN C21  C21  C  0 1 Y N N 15.015 137.114 -0.447 0.211  0.359  -3.151 C21  JAN 27 
JAN C22  C22  C  0 1 Y N N 14.764 136.452 -1.677 -1.011 -0.456 -3.312 C22  JAN 28 
JAN C23  C23  C  0 1 Y N N 14.685 135.042 -1.755 -2.134 -0.199 -2.525 C23  JAN 29 
JAN C24  C24  C  0 1 Y N N 14.378 134.423 -2.987 -3.275 -0.961 -2.685 C24  JAN 30 
JAN CL2  CL2  CL 0 0 N N N 14.252 132.661 -3.090 -4.676 -0.638 -1.712 CL2  JAN 31 
JAN C25  C25  C  0 1 Y N N 14.152 135.198 -4.140 -3.301 -1.986 -3.615 C25  JAN 32 
JAN C26  C26  C  0 1 Y N N 14.230 136.597 -4.068 -2.188 -2.249 -4.394 C26  JAN 33 
JAN C27  C27  C  0 1 Y N N 14.534 137.221 -2.845 -1.045 -1.491 -4.249 C27  JAN 34 
JAN H11A 1H1  H  0 0 N N N 21.144 131.299 0.445  2.326  -4.000 0.850  H11A JAN 35 
JAN H12  2H1  H  0 1 N N N 21.485 132.910 -0.254 2.379  -2.429 0.014  H12  JAN 36 
JAN H13A 3H1  H  0 0 N N N 22.264 132.359 1.260  3.891  -3.213 0.531  H13A JAN 37 
JAN H2   H2   H  0 1 N N N 20.589 131.216 3.209  4.493  -3.116 3.127  H2   JAN 38 
JAN H3   H3   H  0 1 N N N 17.722 134.425 2.857  1.542  -0.367 4.309  H3   JAN 39 
JAN H7   H7   H  0 1 N N N 17.398 132.588 0.193  -1.459 -1.710 3.181  H7   JAN 40 
JAN H8   H8   H  0 1 N N N 16.808 131.405 -1.914 -2.900 -0.254 4.548  H8   JAN 41 
JAN H10  H10  H  0 1 N N N 19.749 133.750 -4.086 -0.659 3.148  3.283  H10  JAN 42 
JAN H11  H11  H  0 1 N N N 20.362 134.956 -1.968 0.783  1.691  1.921  H11  JAN 43 
JAN HN31 1HN3 H  0 0 N N N 21.299 134.491 0.191  -0.971 -1.795 0.726  HN31 JAN 44 
JAN HN32 2HN3 H  0 0 N N N 20.446 135.794 -0.518 0.405  -2.602 0.455  HN32 JAN 45 
JAN H13  H13  H  0 1 N N N 16.995 135.315 -0.968 -0.431 -0.909 -0.833 H13  JAN 46 
JAN H15  H15  H  0 1 N N N 19.509 136.434 2.419  2.798  0.603  1.487  H15  JAN 47 
JAN H16  H16  H  0 1 N N N 17.866 138.177 3.065  3.640  1.868  -0.441 H16  JAN 48 
JAN H181 1H18 H  0 0 N N N 16.701 140.086 2.913  3.946  3.205  -3.688 H181 JAN 49 
JAN H182 2H18 H  0 0 N N N 14.971 140.288 3.390  3.585  3.489  -1.968 H182 JAN 50 
JAN H183 3H18 H  0 0 N N N 15.974 138.883 3.922  4.578  2.093  -2.450 H183 JAN 51 
JAN H20  H20  H  0 1 N N N 13.112 138.180 -0.545 0.221  1.060  -5.158 H20  JAN 52 
JAN H23  H23  H  0 1 N N N 14.862 134.427 -0.857 -2.114 0.599  -1.799 H23  JAN 53 
JAN H25  H25  H  0 1 N N N 13.914 134.709 -5.100 -4.193 -2.582 -3.734 H25  JAN 54 
JAN H26  H26  H  0 1 N N N 14.053 137.205 -4.971 -2.215 -3.049 -5.119 H26  JAN 55 
JAN H27  H27  H  0 1 N N N 14.593 138.322 -2.801 -0.177 -1.697 -4.858 H27  JAN 56 
# 
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 
JAN C1  N1   SING N N 1  
JAN C1  H11A SING N N 2  
JAN C1  H12  SING N N 3  
JAN C1  H13A SING N N 4  
JAN N1  C2   SING Y N 5  
JAN N1  C4   SING Y N 6  
JAN C2  N2   DOUB Y N 7  
JAN C2  H2   SING N N 8  
JAN N2  C3   SING Y N 9  
JAN C3  C4   DOUB Y N 10 
JAN C3  H3   SING N N 11 
JAN C4  C5   SING N N 12 
JAN C5  C6   SING N N 13 
JAN C5  N3   SING N N 14 
JAN C5  C12  SING N N 15 
JAN C6  C7   DOUB Y N 16 
JAN C6  C11  SING Y N 17 
JAN C7  C8   SING Y N 18 
JAN C7  H7   SING N N 19 
JAN C8  C9   DOUB Y N 20 
JAN C8  H8   SING N N 21 
JAN C9  CL1  SING N N 22 
JAN C9  C10  SING Y N 23 
JAN C10 C11  DOUB Y N 24 
JAN C10 H10  SING N N 25 
JAN C11 H11  SING N N 26 
JAN N3  HN31 SING N N 27 
JAN N3  HN32 SING N N 28 
JAN C12 C13  DOUB Y N 29 
JAN C12 C15  SING Y N 30 
JAN C13 C14  SING Y N 31 
JAN C13 H13  SING N N 32 
JAN C14 C17  DOUB Y N 33 
JAN C14 C21  SING Y N 34 
JAN C15 C16  DOUB Y N 35 
JAN C15 H15  SING N N 36 
JAN C16 C17  SING Y N 37 
JAN C16 H16  SING N N 38 
JAN C17 N4   SING Y N 39 
JAN N4  C18  SING N N 40 
JAN N4  C19  SING Y N 41 
JAN C18 H181 SING N N 42 
JAN C18 H182 SING N N 43 
JAN C18 H183 SING N N 44 
JAN C19 O1   DOUB N N 45 
JAN C19 C20  SING Y N 46 
JAN C20 C21  DOUB Y N 47 
JAN C20 H20  SING N N 48 
JAN C21 C22  SING N N 49 
JAN C22 C23  DOUB Y N 50 
JAN C22 C27  SING Y N 51 
JAN C23 C24  SING Y N 52 
JAN C23 H23  SING N N 53 
JAN C24 CL2  SING N N 54 
JAN C24 C25  DOUB Y N 55 
JAN C25 C26  SING Y N 56 
JAN C25 H25  SING N N 57 
JAN C26 C27  DOUB Y N 58 
JAN C26 H26  SING N N 59 
JAN C27 H27  SING N N 60 
# 
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 
JAN SMILES           ACDLabs              10.04 Clc1cccc(c1)C=3c2cc(ccc2N(C(=O)C=3)C)C(N)(c4cncn4C)c5ccc(Cl)cc5                                                                                                
JAN InChI            InChI                1.02b InChI=1/C27H22Cl2N4O/c1-32-16-31-15-25(32)27(30,18-6-9-20(28)10-7-18)19-8-11-24-23(13-19)22(14-26(34)33(24)2)17-4-3-5-21(29)12-17/h3-16H,30H2,1-2H3/t27-/m1/s1 
JAN InChIKey         InChI                1.02b PLHJCIYEEKOWNM-HHHXNRCGBH                                                                                                                                      
JAN SMILES_CANONICAL CACTVS               3.341 Cn1cncc1[C@@](N)(c2ccc(Cl)cc2)c3ccc4N(C)C(=O)C=C(c5cccc(Cl)c5)c4c3                                                                                             
JAN SMILES           CACTVS               3.341 Cn1cncc1[C](N)(c2ccc(Cl)cc2)c3ccc4N(C)C(=O)C=C(c5cccc(Cl)c5)c4c3                                                                                               
JAN SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cn1cncc1[C@@](c2ccc(cc2)Cl)(c3ccc4c(c3)C(=CC(=O)N4C)c5cccc(c5)Cl)N                                                                                             
JAN SMILES           "OpenEye OEToolkits" 1.5.0 Cn1cncc1C(c2ccc(cc2)Cl)(c3ccc4c(c3)C(=CC(=O)N4C)c5cccc(c5)Cl)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 
JAN "SYSTEMATIC NAME" ACDLabs              10.04 6-[(R)-amino(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl]-4-(3-chlorophenyl)-1-methylquinolin-2(1H)-one 
JAN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 6-[(R)-amino-(4-chlorophenyl)-(3-methylimidazol-4-yl)methyl]-4-(3-chlorophenyl)-1-methyl-quinolin-2-one      
# 
