data_FR9
# 
_chem_comp.id                                    FR9 
_chem_comp.name                                  1-[(1R)-3-(6-{[(BENZYLAMINO)CARBONYL]AMINO}-1H-INDOL-1-YL)-1-(HYDROXYMETHYL)PROPYL]-1H-IMIDAZOLE-4-CARBOXAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C24 H26 N6 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         FR236913 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-10-05 
_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                        446.502 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     FR9 
_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        1O5R 
_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 
FR9 C1   C1   C 0 1 Y N N 51.984 54.514 20.752 1.067  0.392  5.931  C1   FR9 1  
FR9 N2   N2   N 0 1 Y N N 52.053 55.575 21.770 0.845  0.533  4.603  N2   FR9 2  
FR9 C3   C3   C 0 1 Y N N 51.793 54.907 22.885 1.757  -0.233 3.948  C3   FR9 3  
FR9 N4   N4   N 0 1 Y N N 51.638 53.616 22.763 2.519  -0.824 4.822  N4   FR9 4  
FR9 C5   C5   C 0 1 Y N N 51.766 53.308 21.342 2.119  -0.465 6.068  C5   FR9 5  
FR9 C8   C8   C 0 1 N N N 51.738 51.964 20.795 2.715  -0.914 7.338  C8   FR9 6  
FR9 O9   O9   O 0 1 N N N 51.908 51.920 19.697 2.268  -0.514 8.396  O9   FR9 7  
FR9 N10  N10  N 0 1 N N N 51.415 51.014 21.523 3.758  -1.768 7.328  N10  FR9 8  
FR9 C13  C13  C 0 1 N N R 52.085 57.033 21.613 -0.190 1.362  3.982  C13  FR9 9  
FR9 C14  C14  C 0 1 N N N 53.512 57.668 21.627 0.466  2.412  3.084  C14  FR9 10 
FR9 O15  O15  O 0 1 N N N 54.543 57.431 22.698 1.227  1.758  2.065  O15  FR9 11 
FR9 C18  C18  C 0 1 N N N 51.382 57.453 20.335 -1.115 0.479  3.143  C18  FR9 12 
FR9 C19  C19  C 0 1 N N N 49.871 57.546 20.530 -2.197 1.345  2.495  C19  FR9 13 
FR9 N22  N22  N 0 1 Y N N 49.231 57.644 19.236 -3.083 0.500  1.691  N22  FR9 14 
FR9 C27  C27  C 0 1 Y N N 48.735 58.810 18.700 -4.219 -0.111 2.151  C27  FR9 15 
FR9 C28  C28  C 0 1 Y N N 48.268 58.568 17.442 -4.796 -0.809 1.161  C28  FR9 16 
FR9 C29  C29  C 0 1 Y N N 48.475 57.179 17.226 -3.962 -0.632 -0.030 C29  FR9 17 
FR9 C30  C30  C 0 1 Y N N 49.083 56.652 18.389 -2.901 0.205  0.358  C30  FR9 18 
FR9 C31  C31  C 0 1 Y N N 48.154 56.337 16.195 -4.038 -1.100 -1.344 C31  FR9 19 
FR9 C32  C32  C 0 1 Y N N 48.446 54.976 16.297 -3.078 -0.747 -2.248 C32  FR9 20 
FR9 C33  C33  C 0 1 Y N N 49.083 54.502 17.447 -2.020 0.077  -1.869 C33  FR9 21 
FR9 C34  C34  C 0 1 Y N N 49.370 55.357 18.479 -1.928 0.551  -0.572 C34  FR9 22 
FR9 N1   N1   N 0 1 N N N 49.313 53.245 17.721 -1.043 0.429  -2.808 N1   FR9 23 
FR9 C2   C2   C 0 1 N N N 49.256 52.202 16.853 -0.614 -0.477 -3.708 C2   FR9 24 
FR9 O1   O1   O 0 1 N N N 48.746 52.328 15.766 -0.997 -1.629 -3.639 O1   FR9 25 
FR9 N3   N3   N 0 1 N N N 49.519 51.081 17.443 0.239  -0.109 -4.683 N3   FR9 26 
FR9 C6   C6   C 0 1 N N N 49.296 49.822 16.782 0.705  -1.095 -5.660 C6   FR9 27 
FR9 C7   C7   C 0 1 Y N N 47.726 49.349 18.700 2.999  -0.394 -6.373 C7   FR9 28 
FR9 C11  C11  C 0 1 Y N N 48.032 49.219 17.355 1.643  -0.432 -6.636 C11  FR9 29 
FR9 C9   C9   C 0 1 Y N N 47.168 48.514 16.536 1.148  0.132  -7.796 C9   FR9 30 
FR9 C12  C12  C 0 1 Y N N 45.994 47.986 17.060 2.007  0.744  -8.688 C12  FR9 31 
FR9 C10  C10  C 0 1 Y N N 45.659 48.138 18.415 3.364  0.783  -8.425 C10  FR9 32 
FR9 C15  C15  C 0 1 Y N N 46.570 48.772 19.201 3.860  0.214  -7.267 C15  FR9 33 
FR9 H1   H1   H 0 1 N N N 52.085 54.613 19.658 0.515  0.867  6.729  H1   FR9 34 
FR9 H3   H3   H 0 1 N N N 51.710 55.402 23.867 1.838  -0.332 2.876  H3   FR9 35 
FR9 H101 1H10 H 0 0 N N N 51.395 50.069 21.139 4.151  -2.064 8.164  H101 FR9 36 
FR9 H102 2H10 H 0 0 N N N 51.259 51.054 22.530 4.112  -2.091 6.484  H102 FR9 37 
FR9 H13  H13  H 0 1 N N N 51.553 57.419 22.514 -0.770 1.860  4.759  H13  FR9 38 
FR9 H141 1H14 H 0 0 N N N 53.376 58.772 21.548 -0.304 3.029  2.622  H141 FR9 39 
FR9 H142 2H14 H 0 0 N N N 53.991 57.409 20.654 1.126  3.041  3.682  H142 FR9 40 
FR9 H15  H15  H 0 1 N N N 55.411 57.817 22.707 1.623  2.454  1.523  H15  FR9 41 
FR9 H181 1H18 H 0 0 N N N 51.643 56.779 19.486 -1.583 -0.268 3.783  H181 FR9 42 
FR9 H182 2H18 H 0 0 N N N 51.800 58.406 19.934 -0.535 -0.019 2.366  H182 FR9 43 
FR9 H191 1H19 H 0 0 N N N 49.582 58.381 21.210 -1.729 2.093  1.855  H191 FR9 44 
FR9 H192 2H19 H 0 0 N N N 49.470 56.702 21.138 -2.777 1.843  3.272  H192 FR9 45 
FR9 H27  H27  H 0 1 N N N 48.715 59.791 19.203 -4.595 -0.040 3.161  H27  FR9 46 
FR9 H28  H28  H 0 1 N N N 47.828 59.317 16.762 -5.703 -1.392 1.230  H28  FR9 47 
FR9 H31  H31  H 0 1 N N N 47.667 56.749 15.295 -4.855 -1.739 -1.644 H31  FR9 48 
FR9 H32  H32  H 0 1 N N N 48.177 54.285 15.481 -3.138 -1.109 -3.263 H32  FR9 49 
FR9 H34  H34  H 0 1 N N N 49.844 54.993 19.406 -1.106 1.190  -0.285 H34  FR9 50 
FR9 HN1  HN1  H 0 1 N N N 48.693 53.005 18.495 -0.675 1.327  -2.812 HN1  FR9 51 
FR9 HN3  HN3  H 0 1 N N N 49.886 51.185 18.389 0.545  0.809  -4.738 HN3  FR9 52 
FR9 H61  1H6  H 0 1 N N N 50.173 49.136 16.849 -0.149 -1.505 -6.199 H61  FR9 53 
FR9 H62  2H6  H 0 1 N N N 49.267 49.915 15.671 1.228  -1.900 -5.143 H62  FR9 54 
FR9 H7   H7   H 0 1 N N N 48.400 49.910 19.369 3.387  -0.839 -5.468 H7   FR9 55 
FR9 H9   H9   H 0 1 N N N 47.414 48.374 15.470 0.088  0.102  -8.002 H9   FR9 56 
FR9 H12  H12  H 0 1 N N N 45.315 47.436 16.387 1.620  1.190  -9.593 H12  FR9 57 
FR9 H10  H10  H 0 1 N N N 44.713 47.772 18.847 4.036  1.259  -9.124 H10  FR9 58 
FR9 H2   H2   H 0 1 N N N 46.364 48.820 20.284 4.920  0.244  -7.062 H2   FR9 59 
# 
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 
FR9 C1  N2   SING Y N 1  
FR9 C1  C5   DOUB Y N 2  
FR9 C1  H1   SING N N 3  
FR9 N2  C3   SING Y N 4  
FR9 N2  C13  SING N N 5  
FR9 C3  N4   DOUB Y N 6  
FR9 C3  H3   SING N N 7  
FR9 N4  C5   SING Y N 8  
FR9 C5  C8   SING N N 9  
FR9 C8  O9   DOUB N N 10 
FR9 C8  N10  SING N N 11 
FR9 N10 H101 SING N N 12 
FR9 N10 H102 SING N N 13 
FR9 C13 C14  SING N N 14 
FR9 C13 C18  SING N N 15 
FR9 C13 H13  SING N N 16 
FR9 C14 O15  SING N N 17 
FR9 C14 H141 SING N N 18 
FR9 C14 H142 SING N N 19 
FR9 O15 H15  SING N N 20 
FR9 C18 C19  SING N N 21 
FR9 C18 H181 SING N N 22 
FR9 C18 H182 SING N N 23 
FR9 C19 N22  SING N N 24 
FR9 C19 H191 SING N N 25 
FR9 C19 H192 SING N N 26 
FR9 N22 C27  SING Y N 27 
FR9 N22 C30  SING Y N 28 
FR9 C27 C28  DOUB Y N 29 
FR9 C27 H27  SING N N 30 
FR9 C28 C29  SING Y N 31 
FR9 C28 H28  SING N N 32 
FR9 C29 C30  DOUB Y N 33 
FR9 C29 C31  SING Y N 34 
FR9 C30 C34  SING Y N 35 
FR9 C31 C32  DOUB Y N 36 
FR9 C31 H31  SING N N 37 
FR9 C32 C33  SING Y N 38 
FR9 C32 H32  SING N N 39 
FR9 C33 C34  DOUB Y N 40 
FR9 C33 N1   SING N N 41 
FR9 C34 H34  SING N N 42 
FR9 N1  C2   SING N N 43 
FR9 N1  HN1  SING N N 44 
FR9 C2  O1   DOUB N N 45 
FR9 C2  N3   SING N N 46 
FR9 N3  C6   SING N N 47 
FR9 N3  HN3  SING N N 48 
FR9 C6  C11  SING N N 49 
FR9 C6  H61  SING N N 50 
FR9 C6  H62  SING N N 51 
FR9 C7  C11  DOUB Y N 52 
FR9 C7  C15  SING Y N 53 
FR9 C7  H7   SING N N 54 
FR9 C11 C9   SING Y N 55 
FR9 C9  C12  DOUB Y N 56 
FR9 C9  H9   SING N N 57 
FR9 C12 C10  SING Y N 58 
FR9 C12 H12  SING N N 59 
FR9 C10 C15  DOUB Y N 60 
FR9 C10 H10  SING N N 61 
FR9 C15 H2   SING N N 62 
# 
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 
FR9 SMILES           ACDLabs              10.04 O=C(N)c1ncn(c1)C(CO)CCn3c2cc(ccc2cc3)NC(=O)NCc4ccccc4 
FR9 InChI            InChI                1.02b 
InChI=1/C24H26N6O3/c25-23(32)21-14-30(16-27-21)20(15-31)9-11-29-10-8-18-6-7-19(12-22(18)29)28-24(33)26-13-17-4-2-1-3-5-17/h1-8,10,12,14,16,20,31H,9,11,13,15H2,(H2,25,32)(H2,26,28,33)/t20-/m1/s1/f/h26,28H,25H2 
FR9 InChIKey         InChI                1.02b KCCUBLLGAMGDJL-PCANAJCTDY 
FR9 SMILES_CANONICAL CACTVS               3.341 NC(=O)c1cn(cn1)[C@@H](CO)CCn2ccc3ccc(NC(=O)NCc4ccccc4)cc23 
FR9 SMILES           CACTVS               3.341 NC(=O)c1cn(cn1)[CH](CO)CCn2ccc3ccc(NC(=O)NCc4ccccc4)cc23 
FR9 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)CNC(=O)Nc2ccc3ccn(c3c2)CC[C@H](CO)n4cc(nc4)C(=O)N 
FR9 SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)CNC(=O)Nc2ccc3ccn(c3c2)CCC(CO)n4cc(nc4)C(=O)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 
FR9 "SYSTEMATIC NAME" ACDLabs              10.04 1-[(1R)-3-{6-[(benzylcarbamoyl)amino]-1H-indol-1-yl}-1-(hydroxymethyl)propyl]-1H-imidazole-4-carboxamide 
FR9 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 1-[(2R)-1-hydroxy-4-[6-(phenylmethylcarbamoylamino)indol-1-yl]butan-2-yl]imidazole-4-carboxamide         
# 
