data_LGF
# 
_chem_comp.id                                    LGF 
_chem_comp.name                                  1-[(3AR)-5-{[3-(2,4-DIFLUOROPHENYL)-5,6-DIHYDROIMIDAZO[1,5-A]PYRAZIN-7(8H)-YL]CARBONYL}-6-METHOXY-3AH-PYRROLO[2,3-B]PYRIDIN-3-YL]-2-[(3R)-3-HYDROXYPYRROLIDIN-1-YL]-2-OXOETHANONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C27 H24 F2 N6 O5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         3,11-DIFLUORO-6,8,13-TRIMETHYL-8H-QUINO[4,3,2-KL]ACRIDIN-13-IUM 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-06-25 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        550.513 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     LGF 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "Corina V3.40" 
_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                  EBI 
# 
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 
LGF C13  C13  C 0 1 Y N N -5.197 0.811  16.066 8.818   -0.637 -0.395 C13  LGF 1  
LGF C18  C18  C 0 1 N N N -1.139 -1.672 24.854 -0.576  1.434  -0.613 C18  LGF 2  
LGF C16  C16  C 0 1 N N N -1.631 -2.206 23.488 0.395   0.858  -1.566 C16  LGF 3  
LGF C15  C15  C 0 1 Y N N -3.199 1.707  17.191 6.616   0.309  -0.380 C15  LGF 4  
LGF C19  C19  C 0 1 N N N -1.951 -1.819 25.919 -1.729  0.767  -0.344 C19  LGF 5  
LGF C21  C21  C 0 1 N N N 0.186  -0.919 24.969 -0.279  2.719  0.039  C21  LGF 6  
LGF C22  C22  C 0 1 N N N -0.231 -0.632 27.124 -2.422  2.823  0.797  C22  LGF 7  
LGF C23  C23  C 0 1 N N R -1.370 -1.265 27.132 -2.618  1.320  0.722  C23  LGF 8  
LGF C24  C24  C 0 1 N N N -1.924 -1.256 28.506 -4.093  1.177  0.491  C24  LGF 9  
LGF C11  C11  C 0 1 Y N N -5.153 0.871  18.368 7.040   -1.804 0.711  C11  LGF 10 
LGF C12  C12  C 0 1 Y N N -5.863 0.536  17.174 8.367   -1.726 0.333  C12  LGF 11 
LGF C27  C27  C 0 1 N N N -3.187 -1.873 29.011 -4.802  0.025  0.128  C27  LGF 12 
LGF F33  F33  F 0 1 N N N -5.736 0.379  14.951 10.117  -0.565 -0.763 F33  LGF 13 
LGF C14  C14  C 0 1 Y N N -3.900 1.395  16.067 7.943   0.376  -0.752 C14  LGF 14 
LGF F32  F32  F 0 1 N N N -5.791 0.511  19.524 6.600   -2.866 1.420  F32  LGF 15 
LGF C10  C10  C 0 1 Y N N -3.876 1.360  18.425 6.155   -0.781 0.358  C10  LGF 16 
LGF C9   C9   C 0 1 Y N N -3.222 1.584  19.761 4.734   -0.858 0.759  C9   LGF 17 
LGF N8   N8   N 0 1 Y N N -2.701 2.670  20.216 4.287   -1.130 1.968  N8   LGF 18 
LGF N5   N5   N 0 1 Y N N -2.891 0.515  20.616 3.665   -0.654 -0.054 N5   LGF 19 
LGF C6   C6   C 0 1 Y N N -2.200 1.035  21.611 2.540   -0.827 0.715  C6   LGF 20 
LGF C7   C7   C 0 1 Y N N -2.061 2.353  21.457 2.945   -1.116 1.958  C7   LGF 21 
LGF C4   C4   C 0 1 N N N -1.644 0.226  22.697 1.133   -0.699 0.185  C4   LGF 22 
LGF N3   N3   N 0 1 N N N -1.908 -1.175 22.459 1.236   -0.116 -1.167 N3   LGF 23 
LGF C2   C2   C 0 1 N N N -2.092 -1.736 21.089 2.280   -0.629 -2.066 C2   LGF 24 
LGF C1   C1   C 0 1 N N N -3.227 -0.914 20.433 3.659   -0.311 -1.477 C1   LGF 25 
LGF O17  O17  O 0 1 N N N -1.752 -3.357 23.167 0.435   1.264  -2.712 O17  LGF 26 
LGF N26  N26  N 0 1 N N N 0.015  -0.209 28.388 -3.624  3.329  0.939  N26  LGF 27 
LGF C25  C25  C 0 1 N N N -1.025 -0.580 29.242 -4.593  2.452  0.720  C25  LGF 28 
LGF N20  N20  N 0 1 N N N 0.578  -0.466 26.062 -1.241  3.405  0.645  N20  LGF 29 
LGF O34  O34  O 0 1 N N N 0.907  -0.775 23.833 0.978   3.204  0.021  O34  LGF 30 
LGF C35  C35  C 0 1 N N N 2.180  -0.050 23.914 1.227   4.418  0.777  C35  LGF 31 
LGF O28  O28  O 0 1 N N N -3.858 -2.641 28.301 -4.202  -1.005 -0.126 O28  LGF 32 
LGF C29  C29  C 0 1 N N N -3.634 -1.602 30.445 -6.289  0.058  0.053  C29  LGF 33 
LGF O31  O31  O 0 1 N N N -3.446 -0.491 30.957 -6.881  1.108  0.198  O31  LGF 34 
LGF N30  N30  N 0 1 N N N -4.214 -2.575 31.258 -6.978  -1.078 -0.175 N30  LGF 35 
LGF C36  C36  C 0 1 N N N -3.684 -3.892 31.486 -8.440  -1.188 -0.273 C36  LGF 36 
LGF C37  C37  C 0 1 N N R -5.040 -4.598 31.463 -8.773  -2.676 -0.514 C37  LGF 37 
LGF O40  O40  O 0 1 N N N -5.564 -4.696 30.140 -9.934  -3.060 0.224  O40  LGF 38 
LGF C38  C38  C 0 1 N N N -5.897 -3.763 32.401 -7.514  -3.405 0.025  C38  LGF 39 
LGF C39  C39  C 0 1 N N N -5.465 -2.335 31.984 -6.389  -2.415 -0.374 C39  LGF 40 
LGF H15  H15  H 0 1 N N N -2.225 2.172  17.166 5.936   1.100  -0.660 H15  LGF 41 
LGF H19  H19  H 0 1 N N N -2.921 -2.293 25.877 -1.994  -0.132 -0.882 H19  LGF 42 
LGF H23  H23  H 0 1 N N N -2.009 -1.969 26.578 -2.362  0.870  1.681  H23  LGF 43 
LGF H12  H12  H 0 1 N N N -6.851 0.099  17.177 9.052   -2.515 0.604  H12  LGF 44 
LGF H14  H14  H 0 1 N N N -3.441 1.605  15.112 8.300   1.221  -1.323 H14  LGF 45 
LGF H7   H7   H 0 1 N N N -1.568 3.039  22.130 2.303   -1.303 2.806  H7   LGF 46 
LGF H41  1H4  H 0 1 N N N -0.557 0.387  22.749 0.664   -1.682 0.132  H41  LGF 47 
LGF H42  2H4  H 0 1 N N N -2.114 0.525  23.646 0.550   -0.042 0.830  H42  LGF 48 
LGF H21  1H2  H 0 1 N N N -1.163 -1.645 20.507 2.171   -1.708 -2.172 H21  LGF 49 
LGF H22  2H2  H 0 1 N N N -2.345 -2.806 21.127 2.184   -0.155 -3.043 H22  LGF 50 
LGF H11  1H1  H 0 1 N N N -4.190 -1.143 20.913 3.870   0.752  -1.596 H11  LGF 51 
LGF H12A 2H1  H 0 0 N N N -3.320 -1.160 19.365 4.420   -0.894 -1.995 H12A LGF 52 
LGF H25  H25  H 0 1 N N N -1.094 -0.364 30.298 -5.645  2.700  0.720  H25  LGF 53 
LGF H351 1H35 H 0 0 N N N 2.564  0.131  22.899 2.276   4.699  0.678  H351 LGF 54 
LGF H352 2H35 H 0 0 N N N 2.022  0.912  24.424 0.598   5.221  0.393  H352 LGF 55 
LGF H353 3H35 H 0 0 N N N 2.908  -0.650 24.480 0.995   4.246  1.828  H353 LGF 56 
LGF H361 1H36 H 0 0 N N N -2.977 -4.238 30.718 -8.900  -0.852 0.657  H361 LGF 57 
LGF H362 2H36 H 0 0 N N N -3.057 -4.035 32.378 -8.803  -0.587 -1.107 H362 LGF 58 
LGF H37  H37  H 0 1 N N N -4.991 -5.647 31.792 -8.910  -2.873 -1.577 H37  LGF 59 
LGF HO40 HO40 H 0 0 N N N -6.513 -4.718 30.176 -10.735 -2.577 -0.022 HO40 LGF 60 
LGF H381 1H38 H 0 0 N N N -6.973 -3.937 32.257 -7.566  -3.527 1.107  H381 LGF 61 
LGF H382 2H38 H 0 0 N N N -5.754 -3.988 33.468 -7.378  -4.367 -0.468 H382 LGF 62 
LGF H391 1H39 H 0 0 N N N -5.312 -1.684 32.857 -6.110  -2.555 -1.419 H391 LGF 63 
LGF H392 2H39 H 0 0 N N N -6.222 -1.812 31.382 -5.521  -2.547 0.272  H392 LGF 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 
LGF C13 F33  SING N N 1  
LGF C13 C14  DOUB Y N 2  
LGF C13 C12  SING Y N 3  
LGF C18 C16  SING N N 4  
LGF C18 C21  SING N N 5  
LGF C18 C19  DOUB N N 6  
LGF C16 N3   SING N N 7  
LGF C16 O17  DOUB N N 8  
LGF C15 C14  SING Y N 9  
LGF C15 C10  DOUB Y N 10 
LGF C15 H15  SING N N 11 
LGF C19 C23  SING N N 12 
LGF C19 H19  SING N N 13 
LGF C21 O34  SING N N 14 
LGF C21 N20  DOUB N N 15 
LGF C22 N20  SING N N 16 
LGF C22 C23  SING N N 17 
LGF C22 N26  DOUB N N 18 
LGF C23 C24  SING N N 19 
LGF C23 H23  SING N N 20 
LGF C24 C27  SING N N 21 
LGF C24 C25  DOUB N N 22 
LGF C11 C12  DOUB Y N 23 
LGF C11 C10  SING Y N 24 
LGF C11 F32  SING N N 25 
LGF C12 H12  SING N N 26 
LGF C27 O28  DOUB N N 27 
LGF C27 C29  SING N N 28 
LGF C14 H14  SING N N 29 
LGF C10 C9   SING N N 30 
LGF C9  N8   DOUB Y N 31 
LGF C9  N5   SING Y N 32 
LGF N8  C7   SING Y N 33 
LGF N5  C1   SING N N 34 
LGF N5  C6   SING Y N 35 
LGF C6  C7   DOUB Y N 36 
LGF C6  C4   SING N N 37 
LGF C7  H7   SING N N 38 
LGF C4  N3   SING N N 39 
LGF C4  H41  SING N N 40 
LGF C4  H42  SING N N 41 
LGF N3  C2   SING N N 42 
LGF C2  C1   SING N N 43 
LGF C2  H21  SING N N 44 
LGF C2  H22  SING N N 45 
LGF C1  H11  SING N N 46 
LGF C1  H12A SING N N 47 
LGF N26 C25  SING N N 48 
LGF C25 H25  SING N N 49 
LGF O34 C35  SING N N 50 
LGF C35 H351 SING N N 51 
LGF C35 H352 SING N N 52 
LGF C35 H353 SING N N 53 
LGF C29 O31  DOUB N N 54 
LGF C29 N30  SING N N 55 
LGF N30 C36  SING N N 56 
LGF N30 C39  SING N N 57 
LGF C36 C37  SING N N 58 
LGF C36 H361 SING N N 59 
LGF C36 H362 SING N N 60 
LGF C37 O40  SING N N 61 
LGF C37 C38  SING N N 62 
LGF C37 H37  SING N N 63 
LGF O40 HO40 SING N N 64 
LGF C38 C39  SING N N 65 
LGF C38 H381 SING N N 66 
LGF C38 H382 SING N N 67 
LGF C39 H391 SING N N 68 
LGF C39 H392 SING N N 69 
# 
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 
LGF SMILES           ACDLabs              10.04 O=C(N1CCC(O)C1)C(=O)C2=CN=C3N=C(OC)C(=CC23)C(=O)N5Cc4cnc(n4CC5)c6ccc(F)cc6F                                                                                                                               
LGF InChI            InChI                1.02b InChI=1/C27H24F2N6O5/c1-40-25-19(9-18-20(11-30-23(18)32-25)22(37)27(39)33-5-4-16(36)13-33)26(38)34-6-7-35-15(12-34)10-31-24(35)17-3-2-14(28)8-21(17)29/h2-3,8-11,16,18,36H,4-7,12-13H2,1H3/t16-,18-/m1/s1 
LGF InChIKey         InChI                1.02b LXYRGMYSFZBUSV-SJLPKXTDBR                                                                                                                                                                                 
LGF SMILES_CANONICAL CACTVS               3.341 COC1=NC2=NC=C([C@H]2C=C1C(=O)N3CCn4c(C3)cnc4c5ccc(F)cc5F)C(=O)C(=O)N6CC[C@@H](O)C6                                                                                                                        
LGF SMILES           CACTVS               3.341 COC1=NC2=NC=C([CH]2C=C1C(=O)N3CCn4c(C3)cnc4c5ccc(F)cc5F)C(=O)C(=O)N6CC[CH](O)C6                                                                                                                           
LGF SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 COC1=NC2=NC=C(C2C=C1C(=O)N3CCn4c(cnc4c5ccc(cc5F)F)C3)C(=O)C(=O)N6CC[C@H](C6)O                                                                                                                             
LGF SMILES           "OpenEye OEToolkits" 1.5.0 COC1=NC2=NC=C(C2C=C1C(=O)N3CCn4c(cnc4c5ccc(cc5F)F)C3)C(=O)C(=O)N6CCC(C6)O                                                                                                                                 
# 
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 
LGF "SYSTEMATIC NAME" ACDLabs              10.04 1-[(3aR)-5-{[3-(2,4-difluorophenyl)-5,6-dihydroimidazo[1,5-a]pyrazin-7(8H)-yl]carbonyl}-6-methoxy-3aH-pyrrolo[2,3-b]pyridin-3-yl]-2-[(3R)-3-hydroxypyrrolidin-1-yl]-2-oxoethanone 
LGF "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 1-[5-[[3-(2,4-difluorophenyl)-6,8-dihydro-5H-imidazo[5,1-c]pyrazin-7-yl]carbonyl]-6-methoxy-3aH-pyrrolo[5,4-b]pyridin-3-yl]-2-[(3R)-3-hydroxypyrrolidin-1-yl]ethane-1,2-dione     
# 
