data_GIL
# 
_chem_comp.id                                    GIL 
_chem_comp.name                                  "2-{[6-{3-[AMINO(IMINO)METHYL]PHENOXY}-4-(DIISOPROPYLAMINO)-3,5-DIFLUOROPYRIDIN-2-YL]OXY}-5-[(ISOBUTYLAMINO)CARBONYL]BENZOIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C30 H35 F2 N5 O5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         PD0297121 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-10-18 
_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                        583.626 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GIL 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "OpenEye/OEToolkits V1.4.2" 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        2C4F 
_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 
GIL C1   C1   C 0 1 Y N N 29.612 7.376  13.890 8.090  0.390  -4.516 C1   GIL 1  
GIL C2   C2   C 0 1 Y N N 28.886 8.486  13.366 7.059  1.318  -4.667 C2   GIL 2  
GIL C3   C3   C 0 1 Y N N 28.889 8.763  11.982 7.273  2.657  -4.342 C3   GIL 3  
GIL C4   C4   C 0 1 Y N N 29.621 7.939  11.104 8.517  3.069  -3.865 C4   GIL 4  
GIL C5   C5   C 0 1 Y N N 30.354 6.833  11.606 9.531  2.136  -3.720 C5   GIL 5  
GIL C6   C6   C 0 1 Y N N 30.345 6.554  12.992 9.335  0.803  -4.039 C6   GIL 6  
GIL C7   C7   C 0 1 N N N 29.602 7.089  15.336 7.868  -1.006 -4.854 C7   GIL 7  
GIL N1   N1   N 0 1 N N N 30.289 6.019  15.810 6.668  -1.517 -5.336 N1   GIL 8  
GIL N2   N2   N 0 1 N N N 28.927 7.863  16.192 8.869  -1.847 -4.695 N2   GIL 9  
GIL C11  C11  C 0 1 Y N N 31.854 6.529  9.751  10.958 2.511  -1.891 C11  GIL 10 
GIL C12  C12  C 0 1 Y N N 33.029 7.320  9.975  12.181 2.912  -1.378 C12  GIL 11 
GIL N3   N3   N 0 1 Y N N 31.386 6.272  8.504  9.924  2.080  -1.134 N3   GIL 12 
GIL C13  C13  C 0 1 Y N N 33.754 7.866  8.861  12.354 2.867  0.001  C13  GIL 13 
GIL O1   O1   O 0 1 N N N 31.111 5.969  10.800 10.762 2.545  -3.247 O1   GIL 14 
GIL C14  C14  C 0 1 Y N N 33.221 7.560  7.573  11.314 2.429  0.813  C14  GIL 15 
GIL C15  C15  C 0 1 Y N N 32.064 6.782  7.435  10.140 2.054  0.194  C15  GIL 16 
GIL N4   N4   N 0 1 N N N 34.915 8.659  8.993  13.580 3.264  0.573  N4   GIL 17 
GIL O2   O2   O 0 1 N N N 31.658 6.587  6.118  9.089  1.613  0.979  O2   GIL 18 
GIL F1   F1   F 0 1 N N N 33.443 7.547  11.243 13.164 3.328  -2.187 F1   GIL 19 
GIL F2   F2   F 0 1 N N N 33.799 8.012  6.446  11.450 2.374  2.144  F2   GIL 20 
GIL C21  C21  C 0 1 Y N N 30.504 5.868  5.812  7.939  1.247  0.348  C21  GIL 21 
GIL C22  C22  C 0 1 Y N N 29.164 6.346  6.066  7.739  -0.068 -0.071 C22  GIL 22 
GIL C23  C23  C 0 1 Y N N 28.069 5.524  5.693  6.553  -0.422 -0.716 C23  GIL 23 
GIL C24  C24  C 0 1 Y N N 28.282 4.247  5.077  5.594  0.547  -0.926 C24  GIL 24 
GIL C25  C25  C 0 1 Y N N 29.611 3.801  4.845  5.767  1.854  -0.521 C25  GIL 25 
GIL C26  C26  C 0 1 Y N N 30.712 4.612  5.211  6.953  2.208  0.123  C26  GIL 26 
GIL C29  C29  C 0 1 N N N 28.898 7.671  6.699  8.754  -1.087 0.156  C29  GIL 27 
GIL O3   O3   O 0 1 N N N 27.776 7.772  7.454  8.739  -2.056 -0.799 O3   GIL 28 
GIL O4   O4   O 0 1 N N N 29.642 8.596  6.584  9.552  -1.103 1.097  O4   GIL 29 
GIL C8   C8   C 0 1 N N N 27.161 3.360  4.660  4.331  0.170  -1.612 C8   GIL 30 
GIL C10  C10  C 0 1 N N N 34.864 10.063 8.377  14.809 2.580  0.224  C10  GIL 31 
GIL C16  C16  C 0 1 N N N 36.081 8.002  9.704  13.630 4.370  1.509  C16  GIL 32 
GIL C17  C17  C 0 1 N N N 36.183 10.633 7.818  15.450 3.284  -0.964 C17  GIL 33 
GIL C18  C18  C 0 1 N N N 34.183 11.054 9.334  14.492 1.125  -0.088 C18  GIL 34 
GIL C19  C19  C 0 1 N N N 37.065 7.411  8.686  12.770 4.037  2.720  C19  GIL 35 
GIL C20  C20  C 0 1 N N N 36.789 8.914  10.742 13.149 5.632  0.807  C20  GIL 36 
GIL O5   O5   O 0 1 N N N 27.330 2.265  4.132  3.723  1.020  -2.258 O5   GIL 37 
GIL N5   N5   N 0 1 N N N 25.928 3.840  4.899  3.973  -1.141 -1.466 N5   GIL 38 
GIL C9   C9   C 0 1 N N N 25.132 4.343  3.777  2.753  -1.678 -2.110 C9   GIL 39 
GIL C27  C27  C 0 1 N N N 23.633 4.520  4.101  3.044  -2.221 -3.515 C27  GIL 40 
GIL C28  C28  C 0 1 N N N 23.227 4.135  5.531  4.088  -3.339 -3.501 C28  GIL 41 
GIL C30  C30  C 0 1 N N N 22.814 3.723  3.082  1.771  -2.682 -4.226 C30  GIL 42 
GIL H2   H2   H 0 1 N N N 28.327 9.122  14.036 6.086  1.007  -5.038 H2   GIL 43 
GIL H3   H3   H 0 1 N N N 28.332 9.604  11.597 6.470  3.379  -4.460 H3   GIL 44 
GIL H4   H4   H 0 1 N N N 29.624 8.150  10.045 8.677  4.114  -3.613 H4   GIL 45 
GIL H6   H6   H 0 1 N N N 30.900 5.709  13.372 10.141 0.083  -3.919 H6   GIL 46 
GIL H1N1 1H1N H 0 0 N N N 30.824 5.377  15.261 6.562  -2.501 -5.562 H1N1 GIL 47 
GIL H1N2 2H1N H 0 0 N N N 30.169 5.982  16.802 5.849  -0.936 -5.470 H1N2 GIL 48 
GIL H23  H23  H 0 1 N N N 27.061 5.865  5.876  6.396  -1.448 -1.043 H23  GIL 49 
GIL H25  H25  H 0 1 N N N 29.782 2.838  4.387  5.006  2.611  -0.691 H25  GIL 50 
GIL H26  H26  H 0 1 N N N 31.718 4.265  5.028  7.102  3.234  0.448  H26  GIL 51 
GIL HA   HA   H 0 1 N N N 27.722 8.644  7.827  9.419  -2.748 -0.655 HA   GIL 52 
GIL H10  H10  H 0 1 N N N 34.254 9.927  7.472  15.482 2.630  1.087  H10  GIL 53 
GIL H16  H16  H 0 1 N N N 35.658 7.182  10.303 14.671 4.501  1.823  H16  GIL 54 
GIL H171 1H17 H 0 0 N N N 37.005 9.934  8.033  16.392 2.800  -1.242 H171 GIL 55 
GIL H172 2H17 H 0 0 N N N 36.393 11.603 8.292  14.790 3.275  -1.838 H172 GIL 56 
GIL H173 3H17 H 0 0 N N N 36.093 10.769 6.730  15.665 4.331  -0.725 H173 GIL 57 
GIL H181 1H18 H 0 0 N N N 33.215 11.364 8.913  14.024 0.636  0.773  H181 GIL 58 
GIL H182 2H18 H 0 0 N N N 34.826 11.937 9.466  15.404 0.572  -0.338 H182 GIL 59 
GIL H183 3H18 H 0 0 N N N 34.020 10.570 10.309 13.799 1.038  -0.933 H183 GIL 60 
GIL H191 1H19 H 0 0 N N N 37.432 6.441  9.052  12.800 4.848  3.455  H191 GIL 61 
GIL H192 2H19 H 0 0 N N N 37.913 8.099  8.554  11.724 3.873  2.435  H192 GIL 62 
GIL H193 3H19 H 0 0 N N N 36.555 7.270  7.722  13.124 3.123  3.209  H193 GIL 63 
GIL H201 1H20 H 0 0 N N N 36.157 9.789  10.953 13.774 5.851  -0.066 H201 GIL 64 
GIL H202 2H20 H 0 0 N N N 37.756 9.249  10.337 13.193 6.494  1.481  H202 GIL 65 
GIL H203 3H20 H 0 0 N N N 36.956 8.351  11.672 12.117 5.526  0.455  H203 GIL 66 
GIL H5   H5   H 0 1 N N N 25.560 3.853  5.829  4.532  -1.814 -0.982 H5   GIL 67 
GIL H9C1 1H9C H 0 0 N N N 25.201 3.595  2.974  2.004  -0.881 -2.152 H9C1 GIL 68 
GIL H9C2 2H9C H 0 0 N N N 25.535 5.325  3.487  2.354  -2.476 -1.474 H9C2 GIL 69 
GIL H27  H27  H 0 1 N N N 23.424 5.598  4.033  3.464  -1.391 -4.098 H27  GIL 70 
GIL H281 1H28 H 0 0 N N N 22.693 3.173  5.514  3.717  -4.237 -2.997 H281 GIL 71 
GIL H282 2H28 H 0 0 N N N 22.570 4.913  5.947  4.361  -3.621 -4.523 H282 GIL 72 
GIL H283 3H28 H 0 0 N N N 24.127 4.043  6.156  5.001  -3.013 -2.991 H283 GIL 73 
GIL H301 1H30 H 0 0 N N N 23.315 2.765  2.878  1.319  -3.547 -3.730 H301 GIL 74 
GIL H302 2H30 H 0 0 N N N 22.729 4.299  2.149  1.991  -2.969 -5.260 H302 GIL 75 
GIL H303 3H30 H 0 0 N N N 21.809 3.532  3.487  1.029  -1.878 -4.255 H303 GIL 76 
GIL HN1  HN1  H 0 1 N N N 28.485 8.595  15.673 9.687  -1.343 -4.337 HN1  GIL 77 
# 
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 
GIL C1  C2   SING Y N 1  
GIL C1  C6   DOUB Y N 2  
GIL C1  C7   SING N N 3  
GIL C2  C3   DOUB Y N 4  
GIL C2  H2   SING N N 5  
GIL C3  C4   SING Y N 6  
GIL C3  H3   SING N N 7  
GIL C4  C5   DOUB Y N 8  
GIL C4  H4   SING N N 9  
GIL C5  C6   SING Y N 10 
GIL C5  O1   SING N N 11 
GIL C6  H6   SING N N 12 
GIL C7  N1   SING N N 13 
GIL C7  N2   DOUB N N 14 
GIL N1  H1N1 SING N N 15 
GIL N1  H1N2 SING N N 16 
GIL C11 C12  DOUB Y N 17 
GIL C11 N3   SING Y N 18 
GIL C11 O1   SING N N 19 
GIL C12 C13  SING Y N 20 
GIL C12 F1   SING N N 21 
GIL N3  C15  DOUB Y N 22 
GIL C13 C14  DOUB Y N 23 
GIL C13 N4   SING N N 24 
GIL C14 C15  SING Y N 25 
GIL C14 F2   SING N N 26 
GIL C15 O2   SING N N 27 
GIL N4  C10  SING N N 28 
GIL N4  C16  SING N N 29 
GIL O2  C21  SING N N 30 
GIL C21 C22  DOUB Y N 31 
GIL C21 C26  SING Y N 32 
GIL C22 C23  SING Y N 33 
GIL C22 C29  SING N N 34 
GIL C23 C24  DOUB Y N 35 
GIL C23 H23  SING N N 36 
GIL C24 C25  SING Y N 37 
GIL C24 C8   SING N N 38 
GIL C25 C26  DOUB Y N 39 
GIL C25 H25  SING N N 40 
GIL C26 H26  SING N N 41 
GIL C29 O3   SING N N 42 
GIL C29 O4   DOUB N N 43 
GIL O3  HA   SING N N 44 
GIL C8  O5   DOUB N N 45 
GIL C8  N5   SING N N 46 
GIL C10 C17  SING N N 47 
GIL C10 C18  SING N N 48 
GIL C10 H10  SING N N 49 
GIL C16 C19  SING N N 50 
GIL C16 C20  SING N N 51 
GIL C16 H16  SING N N 52 
GIL C17 H171 SING N N 53 
GIL C17 H172 SING N N 54 
GIL C17 H173 SING N N 55 
GIL C18 H181 SING N N 56 
GIL C18 H182 SING N N 57 
GIL C18 H183 SING N N 58 
GIL C19 H191 SING N N 59 
GIL C19 H192 SING N N 60 
GIL C19 H193 SING N N 61 
GIL C20 H201 SING N N 62 
GIL C20 H202 SING N N 63 
GIL C20 H203 SING N N 64 
GIL N5  C9   SING N N 65 
GIL N5  H5   SING N N 66 
GIL C9  C27  SING N N 67 
GIL C9  H9C1 SING N N 68 
GIL C9  H9C2 SING N N 69 
GIL C27 C28  SING N N 70 
GIL C27 C30  SING N N 71 
GIL C27 H27  SING N N 72 
GIL C28 H281 SING N N 73 
GIL C28 H282 SING N N 74 
GIL C28 H283 SING N N 75 
GIL C30 H301 SING N N 76 
GIL C30 H302 SING N N 77 
GIL C30 H303 SING N N 78 
GIL HN1 N2   SING N N 79 
# 
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 
GIL SMILES           ACDLabs              10.04 O=C(NCC(C)C)c3ccc(Oc2nc(Oc1cc(C(=[N@H])N)ccc1)c(F)c(c2F)N(C(C)C)C(C)C)c(C(=O)O)c3 
GIL InChI            InChI                1.02b 
InChI=1/C30H35F2N5O5/c1-15(2)14-35-27(38)19-10-11-22(21(13-19)30(39)40)42-29-24(32)25(37(16(3)4)17(5)6)23(31)28(36-29)41-20-9-7-8-18(12-20)26(33)34/h7-13,15-17H,14H2,1-6H3,(H3,33,34)(H,35,38)(H,39,40)/f/h33,35,39H,34H2/b33-26+ 
GIL InChIKey         InChI                1.02b JLWMMYZWEHHTFF-KWWNWVPYDX 
GIL SMILES_CANONICAL CACTVS               3.341 CC(C)CNC(=O)c1ccc(Oc2nc(Oc3cccc(c3)C(N)=N)c(F)c(N(C(C)C)C(C)C)c2F)c(c1)C(O)=O 
GIL SMILES           CACTVS               3.341 CC(C)CNC(=O)c1ccc(Oc2nc(Oc3cccc(c3)C(N)=N)c(F)c(N(C(C)C)C(C)C)c2F)c(c1)C(O)=O 
GIL SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 [H]/N=C(\c1cccc(c1)Oc2c(c(c(c(n2)Oc3ccc(cc3C(=O)O)C(=O)NCC(C)C)F)N(C(C)C)C(C)C)F)/N 
GIL SMILES           "OpenEye OEToolkits" 1.5.0 [H]N=C(c1cccc(c1)Oc2c(c(c(c(n2)Oc3ccc(cc3C(=O)O)C(=O)NCC(C)C)F)N(C(C)C)C(C)C)F)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 
GIL "SYSTEMATIC NAME" ACDLabs              10.04 "2-({4-[bis(1-methylethyl)amino]-6-(3-carbamimidoylphenoxy)-3,5-difluoropyridin-2-yl}oxy)-5-[(2-methylpropyl)carbamoyl]benzoic acid" 
GIL "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[6-(3-carbamimidoylphenoxy)-4-(di(propan-2-yl)amino)-3,5-difluoro-pyridin-2-yl]oxy-5-(2-methylpropylcarbamoyl)benzoic acid"       
# 
