data_I08
# 
_chem_comp.id                                    I08 
_chem_comp.name                                  (3R,4S)-N-(4-{TRANS-2-[4-(2-FLUORO-6-HYDROXY-3-METHOXY-BENZOYL)-PHENYL]-VINYL}-AZEPAN-3-YL)-ISONICOTINAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C28 H28 F N3 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-04-14 
_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                        489.538 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     I08 
_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        1SVH 
_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 
I08 F96  F96  F 0 1 N N N 36.269 16.201 7.814  4.265  -1.175 -1.189 F96  I08 1  
I08 C76  C76  C 0 1 Y N N 35.213 15.386 7.937  4.737  -0.437 -0.161 C76  I08 2  
I08 C75  C75  C 0 1 Y N N 35.384 14.278 8.689  5.434  -1.045 0.869  C75  I08 3  
I08 O95  O95  O 0 1 N N N 36.640 14.042 9.269  5.649  -2.389 0.843  O95  I08 4  
I08 C98  C98  C 0 1 N N N 36.828 12.744 9.858  6.390  -2.712 2.021  C98  I08 5  
I08 C74  C74  C 0 1 Y N N 34.251 13.439 8.851  5.920  -0.288 1.926  C74  I08 6  
I08 C73  C73  C 0 1 Y N N 33.046 13.730 8.261  5.709  1.077  1.964  C73  I08 7  
I08 C72  C72  C 0 1 Y N N 32.859 14.915 7.487  5.009  1.702  0.945  C72  I08 8  
I08 O92  O92  O 0 1 N N N 31.724 15.198 6.916  4.803  3.043  0.983  O92  I08 9  
I08 C71  C71  C 0 1 Y N N 33.991 15.757 7.345  4.513  0.945  -0.128 C71  I08 10 
I08 C61  C61  C 0 1 N N N 33.901 16.949 6.534  3.768  1.601  -1.216 C61  I08 11 
I08 O62  O62  O 0 1 N N N 34.515 16.980 5.477  4.364  2.053  -2.175 O62  I08 12 
I08 C54  C54  C 0 1 Y N N 33.107 18.105 6.867  2.297  1.710  -1.142 C54  I08 13 
I08 C55  C55  C 0 1 Y N N 32.640 18.252 8.205  1.580  2.234  -2.222 C55  I08 14 
I08 C56  C56  C 0 1 Y N N 31.891 19.378 8.577  0.214  2.335  -2.153 C56  I08 15 
I08 C53  C53  C 0 1 Y N N 32.810 19.059 5.880  1.621  1.284  0.005  C53  I08 16 
I08 C52  C52  C 0 1 Y N N 32.051 20.180 6.242  0.257  1.392  0.076  C52  I08 17 
I08 C51  C51  C 0 1 Y N N 31.583 20.350 7.599  -0.460 1.915  -1.003 C51  I08 18 
I08 C42  C42  C 0 1 N N N 30.815 21.528 7.971  -1.931 2.024  -0.930 C42  I08 19 
I08 C41  C41  C 0 1 N N N 30.181 21.634 9.163  -2.572 1.625  0.162  C41  I08 20 
I08 C37  C37  C 0 1 N N S 29.444 22.884 9.533  -4.073 1.736  0.237  C37  I08 21 
I08 C36  C36  C 0 1 N N N 30.522 23.953 9.928  -4.469 2.649  1.434  C36  I08 22 
I08 C35  C35  C 0 1 N N N 31.555 23.473 10.992 -5.880 3.000  1.340  C35  I08 23 
I08 C34  C34  C 0 1 N N N 30.948 23.626 12.388 -6.824 1.794  1.393  C34  I08 24 
I08 N33  N33  N 0 1 N N N 29.777 22.713 12.548 -6.978 1.321  0.038  N33  I08 25 
I08 C32  C32  C 0 1 N N N 28.517 23.213 11.946 -6.064 0.179  -0.172 C32  I08 26 
I08 C31  C31  C 0 1 N N S 28.308 22.665 10.558 -4.670 0.370  0.448  C31  I08 27 
I08 N23  N23  N 0 1 N N N 27.071 23.280 10.071 -3.765 -0.627 -0.130 N23  I08 28 
I08 C21  C21  C 0 1 N N N 25.975 22.511 9.699  -3.701 -1.865 0.399  C21  I08 29 
I08 O22  O22  O 0 1 N N N 26.149 21.300 9.608  -4.394 -2.155 1.354  O22  I08 30 
I08 C14  C14  C 0 1 Y N N 24.655 23.080 9.493  -2.786 -2.873 -0.185 C14  I08 31 
I08 C13  C13  C 0 1 Y N N 23.584 22.176 9.371  -2.704 -4.163 0.347  C13  I08 32 
I08 C12  C12  C 0 1 Y N N 22.297 22.625 9.218  -1.837 -5.071 -0.228 C12  I08 33 
I08 N11  N11  N 0 1 Y N N 22.046 23.991 9.127  -1.094 -4.735 -1.264 N11  I08 34 
I08 C16  C16  C 0 1 Y N N 23.079 24.914 9.222  -1.140 -3.531 -1.797 C16  I08 35 
I08 C15  C15  C 0 1 Y N N 24.386 24.469 9.411  -1.984 -2.562 -1.288 C15  I08 36 
I08 H981 1H98 H 0 0 N N N 36.603 11.951 9.107  7.335  -2.169 2.015  H981 I08 37 
I08 H982 2H98 H 0 0 N N N 37.826 12.557 10.319 5.814  -2.430 2.902  H982 I08 38 
I08 H983 3H98 H 0 0 N N N 36.023 12.547 10.604 6.587  -3.784 2.043  H983 I08 39 
I08 H74  H74  H 0 1 N N N 34.309 12.522 9.461  6.467  -0.768 2.724  H74  I08 40 
I08 H73  H73  H 0 1 N N N 32.225 13.009 8.409  6.090  1.658  2.790  H73  I08 41 
I08 H92  H92  H 0 1 N N N 31.600 15.987 6.401  5.588  3.458  0.601  H92  I08 42 
I08 H55  H55  H 0 1 N N N 32.862 17.483 8.964  2.101  2.559  -3.110 H55  I08 43 
I08 H56  H56  H 0 1 N N N 31.551 19.497 9.619  -0.340 2.739  -2.987 H56  I08 44 
I08 H53  H53  H 0 1 N N N 33.165 18.931 4.844  2.175  0.880  0.839  H53  I08 45 
I08 H52  H52  H 0 1 N N N 31.823 20.926 5.462  -0.265 1.067  0.964  H52  I08 46 
I08 H42  H42  H 0 1 N N N 30.706 22.400 7.304  -2.485 2.428  -1.764 H42  I08 47 
I08 H41  H41  H 0 1 N N N 30.261 20.741 9.805  -2.018 1.221  0.996  H41  I08 48 
I08 H37  H37  H 0 1 N N N 28.864 23.269 8.662  -4.455 2.163  -0.690 H37  I08 49 
I08 H361 1H36 H 0 0 N N N 30.028 24.894 10.265 -4.288 2.119  2.369  H361 I08 50 
I08 H362 2H36 H 0 0 N N N 31.048 24.326 9.019  -3.867 3.558  1.411  H362 I08 51 
I08 H351 1H35 H 0 0 N N N 32.535 23.997 10.897 -6.126 3.671  2.163  H351 I08 52 
I08 H352 2H35 H 0 0 N N N 31.912 22.435 10.797 -6.045 3.530  0.402  H352 I08 53 
I08 H341 1H34 H 0 0 N N N 30.683 24.686 12.612 -6.391 1.009  2.014  H341 I08 54 
I08 H342 2H34 H 0 0 N N N 31.707 23.473 13.190 -7.792 2.096  1.794  H342 I08 55 
I08 H33  H33  H 0 1 N N N 29.635 22.489 13.533 -7.917 0.958  -0.038 H33  I08 56 
I08 H321 1H32 H 0 0 N N N 28.476 24.327 11.954 -6.518 -0.713 0.260  H321 I08 57 
I08 H322 2H32 H 0 0 N N N 27.641 23.003 12.603 -5.947 0.021  -1.244 H322 I08 58 
I08 H31  H31  H 0 1 N N N 28.273 21.554 10.647 -4.741 0.190  1.521  H31  I08 59 
I08 H23  H23  H 0 1 N N N 26.968 24.291 9.987  -3.212 -0.395 -0.892 H23  I08 60 
I08 H13  H13  H 0 1 N N N 23.758 21.087 9.396  -3.309 -4.445 1.196  H13  I08 61 
I08 H12  H12  H 0 1 N N N 21.472 21.895 9.169  -1.766 -6.070 0.176  H12  I08 62 
I08 H16  H16  H 0 1 N N N 22.863 25.993 9.148  -0.514 -3.299 -2.646 H16  I08 63 
I08 H15  H15  H 0 1 N N N 25.200 25.209 9.495  -2.017 -1.577 -1.729 H15  I08 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 
I08 F96 C76  SING N N 1  
I08 C76 C75  DOUB Y N 2  
I08 C76 C71  SING Y N 3  
I08 C75 O95  SING N N 4  
I08 C75 C74  SING Y N 5  
I08 O95 C98  SING N N 6  
I08 C98 H981 SING N N 7  
I08 C98 H982 SING N N 8  
I08 C98 H983 SING N N 9  
I08 C74 C73  DOUB Y N 10 
I08 C74 H74  SING N N 11 
I08 C73 C72  SING Y N 12 
I08 C73 H73  SING N N 13 
I08 C72 O92  SING N N 14 
I08 C72 C71  DOUB Y N 15 
I08 O92 H92  SING N N 16 
I08 C71 C61  SING N N 17 
I08 C61 O62  DOUB N N 18 
I08 C61 C54  SING N N 19 
I08 C54 C55  SING Y N 20 
I08 C54 C53  DOUB Y N 21 
I08 C55 C56  DOUB Y N 22 
I08 C55 H55  SING N N 23 
I08 C56 C51  SING Y N 24 
I08 C56 H56  SING N N 25 
I08 C53 C52  SING Y N 26 
I08 C53 H53  SING N N 27 
I08 C52 C51  DOUB Y N 28 
I08 C52 H52  SING N N 29 
I08 C51 C42  SING N N 30 
I08 C42 C41  DOUB N E 31 
I08 C42 H42  SING N N 32 
I08 C41 C37  SING N N 33 
I08 C41 H41  SING N N 34 
I08 C37 C36  SING N N 35 
I08 C37 C31  SING N N 36 
I08 C37 H37  SING N N 37 
I08 C36 C35  SING N N 38 
I08 C36 H361 SING N N 39 
I08 C36 H362 SING N N 40 
I08 C35 C34  SING N N 41 
I08 C35 H351 SING N N 42 
I08 C35 H352 SING N N 43 
I08 C34 N33  SING N N 44 
I08 C34 H341 SING N N 45 
I08 C34 H342 SING N N 46 
I08 N33 C32  SING N N 47 
I08 N33 H33  SING N N 48 
I08 C32 C31  SING N N 49 
I08 C32 H321 SING N N 50 
I08 C32 H322 SING N N 51 
I08 C31 N23  SING N N 52 
I08 C31 H31  SING N N 53 
I08 N23 C21  SING N N 54 
I08 N23 H23  SING N N 55 
I08 C21 O22  DOUB N N 56 
I08 C21 C14  SING N N 57 
I08 C14 C13  SING Y N 58 
I08 C14 C15  DOUB Y N 59 
I08 C13 C12  DOUB Y N 60 
I08 C13 H13  SING N N 61 
I08 C12 N11  SING Y N 62 
I08 C12 H12  SING N N 63 
I08 N11 C16  DOUB Y N 64 
I08 C16 C15  SING Y N 65 
I08 C16 H16  SING N N 66 
I08 C15 H15  SING N N 67 
# 
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 
I08 SMILES           ACDLabs              10.04 Fc1c(OC)ccc(O)c1C(=O)c2ccc(cc2)\C=C\C4CCCNCC4NC(=O)c3ccncc3 
I08 InChI            InChI                1.02b 
InChI=1/C28H28FN3O4/c1-36-24-11-10-23(33)25(26(24)29)27(34)20-8-5-18(6-9-20)4-7-19-3-2-14-31-17-22(19)32-28(35)21-12-15-30-16-13-21/h4-13,15-16,19,22,31,33H,2-3,14,17H2,1H3,(H,32,35)/b7-4+/t19-,22+/m0/s1/f/h32H 
I08 InChIKey         InChI                1.02b QXALMENQPNPILV-VOFXENKQDU 
I08 SMILES_CANONICAL CACTVS               3.341 COc1ccc(O)c(c1F)C(=O)c2ccc(\C=C\[C@@H]3CCCNC[C@H]3NC(=O)c4ccncc4)cc2 
I08 SMILES           CACTVS               3.341 COc1ccc(O)c(c1F)C(=O)c2ccc(C=C[CH]3CCCNC[CH]3NC(=O)c4ccncc4)cc2 
I08 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 COc1ccc(c(c1F)C(=O)c2ccc(cc2)\C=C\[C@@H]3CCCNC[C@H]3NC(=O)c4ccncc4)O 
I08 SMILES           "OpenEye OEToolkits" 1.5.0 COc1ccc(c(c1F)C(=O)c2ccc(cc2)C=CC3CCCNCC3NC(=O)c4ccncc4)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 
I08 "SYSTEMATIC NAME" ACDLabs              10.04 N-{(3S,4S)-4-[(E)-2-{4-[(2-fluoro-6-hydroxy-3-methoxyphenyl)carbonyl]phenyl}ethenyl]azepan-3-yl}pyridine-4-carboxamide 
I08 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 N-[(3S,4S)-4-[(E)-2-[4-(2-fluoro-6-hydroxy-3-methoxy-phenyl)carbonylphenyl]ethenyl]azepan-3-yl]pyridine-4-carboxamide  
# 
