data_FR5
# 
_chem_comp.id                                    FR5 
_chem_comp.name                                  1-((1R)-1-(HYDROXYMETHYL)-3-(6-((3-(1-METHYL-1H-BENZIMIDAZOL-2-YL)PROPANOYL)AMINO)-1H-INDOL-1-YL)PROPYL)-1H-IMIDAZOLE-4-CARBOXAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C27 H29 N7 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         FR235999 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2002-12-13 
_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                        499.564 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     FR5 
_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        1NDZ 
_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 
FR5 C1   C1   C 0 1 Y N N 51.262 54.394 21.046 2.591  -3.328 0.423  C1   FR5 1  
FR5 N2   N2   N 0 1 Y N N 51.238 55.323 22.073 2.715  -2.449 -0.599 N2   FR5 2  
FR5 C3   C3   C 0 1 Y N N 51.155 54.596 23.229 1.480  -1.953 -0.871 C3   FR5 3  
FR5 N4   N4   N 0 1 Y N N 51.026 53.356 23.016 0.619  -2.489 -0.055 N4   FR5 4  
FR5 C5   C5   C 0 1 Y N N 51.019 53.233 21.600 1.271  -3.348 0.770  C5   FR5 5  
FR5 C8   C8   C 0 1 N N N 50.831 51.983 20.866 0.664  -4.159 1.839  C8   FR5 6  
FR5 O9   O9   O 0 1 N N N 50.577 51.951 19.632 1.360  -4.895 2.514  O9   FR5 7  
FR5 N10  N10  N 0 1 N N N 50.847 50.909 21.641 -0.661 -4.085 2.071  N10  FR5 8  
FR5 C13  C13  C 0 1 N N R 51.141 56.802 21.888 3.957  -2.100 -1.293 C13  FR5 9  
FR5 C14  C14  C 0 1 N N N 52.518 57.604 21.793 3.831  -2.455 -2.776 C14  FR5 10 
FR5 O15  O15  O 0 1 N N N 53.600 57.321 22.690 5.076  -2.211 -3.432 O15  FR5 11 
FR5 C18  C18  C 0 1 N N N 50.371 57.194 20.629 4.219  -0.600 -1.148 C18  FR5 12 
FR5 C19  C19  C 0 1 N N N 48.892 56.616 20.612 4.480  -0.268 0.322  C19  FR5 13 
FR5 N22  N22  N 0 1 Y N N 48.232 56.768 19.201 4.643  1.180  0.474  N22  FR5 14 
FR5 C27  C27  C 0 1 Y N N 47.764 57.934 18.695 5.842  1.841  0.481  C27  FR5 15 
FR5 C28  C28  C 0 1 Y N N 47.213 57.692 17.517 5.638  3.158  0.639  C28  FR5 16 
FR5 C29  C29  C 0 1 Y N N 47.337 56.252 17.328 4.190  3.358  0.742  C29  FR5 17 
FR5 C30  C30  C 0 1 Y N N 48.067 55.738 18.378 3.612  2.080  0.632  C30  FR5 18 
FR5 C31  C31  C 0 1 Y N N 47.121 55.474 16.261 3.377  4.481  0.911  C31  FR5 19 
FR5 C32  C32  C 0 1 Y N N 47.463 54.210 16.308 2.021  4.336  0.971  C32  FR5 20 
FR5 C33  C33  C 0 1 Y N N 48.120 53.712 17.391 1.440  3.073  0.862  C33  FR5 21 
FR5 C34  C34  C 0 1 Y N N 48.374 54.478 18.459 2.230  1.948  0.699  C34  FR5 22 
FR5 N1   N1   N 0 1 N N N 48.440 52.484 17.557 0.048  2.941  0.924  N1   FR5 23 
FR5 C2   C2   C 0 1 N N N 48.295 51.518 16.783 -0.571 1.984  0.205  C2   FR5 24 
FR5 O1   O1   O 0 1 N N N 47.607 51.515 15.784 0.065  1.301  -0.569 O1   FR5 25 
FR5 C4   C4   C 0 1 N N N 49.144 50.282 17.124 -2.053 1.763  0.364  C4   FR5 26 
FR5 C6   C6   C 0 1 N N N 48.586 48.902 16.698 -2.501 0.627  -0.559 C6   FR5 27 
FR5 C9   C9   C 0 1 Y N N 44.601 47.619 21.132 -8.221 -0.754 0.625  C9   FR5 28 
FR5 C15  C15  C 0 1 Y N N 45.828 48.211 20.793 -6.929 -1.017 0.982  C15  FR5 29 
FR5 C10  C10  C 0 1 Y N N 46.266 48.327 19.489 -5.879 -0.364 0.331  C10  FR5 30 
FR5 C16  C16  C 0 1 Y N N 45.627 47.631 18.438 -6.167 0.564  -0.685 C16  FR5 31 
FR5 C11  C11  C 0 1 Y N N 44.409 47.058 18.717 -7.485 0.814  -1.039 C11  FR5 32 
FR5 C17  C17  C 0 1 Y N N 43.935 46.996 20.078 -8.505 0.158  -0.382 C17  FR5 33 
FR5 N11  N11  N 0 1 Y N N 47.405 48.885 18.948 -4.528 -0.409 0.455  N11  FR5 34 
FR5 C12  C12  C 0 1 Y N N 47.417 48.580 17.642 -3.983 0.406  -0.401 C12  FR5 35 
FR5 N13  N13  N 0 1 Y N N 46.346 47.893 17.260 -4.946 1.030  -1.132 N13  FR5 36 
FR5 C7   C7   C 0 1 N N N 46.004 47.439 15.925 -4.729 2.017  -2.192 C7   FR5 37 
FR5 H1   H1   H 0 1 N N N 51.444 54.552 19.970 3.385  -3.898 0.882  H1   FR5 38 
FR5 H3   H3   H 0 1 N N N 51.190 54.983 24.261 1.249  -1.230 -1.640 H3   FR5 39 
FR5 H101 1H10 H 0 0 N N N 50.716 50.037 21.129 -1.216 -3.498 1.533  H101 FR5 40 
FR5 H102 2H10 H 0 0 N N N 51.053 50.935 22.640 -1.061 -4.619 2.776  H102 FR5 41 
FR5 H13  H13  H 0 1 N N N 50.617 57.088 22.830 4.786  -2.657 -0.856 H13  FR5 42 
FR5 H141 1H14 H 0 0 N N N 52.290 58.693 21.859 3.567  -3.508 -2.876 H141 FR5 43 
FR5 H142 2H14 H 0 0 N N N 52.900 57.513 20.750 3.053  -1.841 -3.231 H142 FR5 44 
FR5 H15O OH15 H 0 0 N N N 54.420 57.798 22.634 4.953  -2.446 -4.362 H15O FR5 45 
FR5 H181 1H18 H 0 0 N N N 50.928 56.896 19.710 3.348  -0.044 -1.497 H181 FR5 46 
FR5 H182 2H18 H 0 0 N N N 50.370 58.300 20.488 5.089  -0.323 -1.743 H182 FR5 47 
FR5 H191 1H19 H 0 0 N N N 48.264 57.080 21.408 5.388  -0.772 0.653  H191 FR5 48 
FR5 H192 2H19 H 0 0 N N N 48.864 55.558 20.964 3.637  -0.604 0.926  H192 FR5 49 
FR5 H27  H27  H 0 1 N N N 47.823 58.928 19.169 6.809  1.372  0.374  H27  FR5 50 
FR5 H28  H28  H 0 1 N N N 46.773 58.472 16.873 6.397  3.925  0.681  H28  FR5 51 
FR5 H31  H31  H 0 1 N N N 46.661 55.875 15.342 3.821  5.462  0.995  H31  FR5 52 
FR5 H32  H32  H 0 1 N N N 47.201 53.573 15.447 1.394  5.205  1.102  H32  FR5 53 
FR5 H34  H34  H 0 1 N N N 48.825 54.081 19.384 1.774  0.972  0.622  H34  FR5 54 
FR5 HN1  HN1  H 0 1 N N N 48.879 52.237 18.444 -0.471 3.539  1.485  HN1  FR5 55 
FR5 H41  1H4  H 0 1 N N N 49.363 50.272 18.217 -2.587 2.676  0.101  H41  FR5 56 
FR5 H42  2H4  H 0 1 N N N 50.171 50.411 16.709 -2.273 1.499  1.398  H42  FR5 57 
FR5 H61  1H6  H 0 1 N N N 49.364 48.103 16.675 -1.967 -0.286 -0.296 H61  FR5 58 
FR5 H62  2H6  H 0 1 N N N 48.304 48.857 15.620 -2.281 0.892  -1.593 H62  FR5 59 
FR5 H9   H9   H 0 1 N N N 44.189 47.642 22.155 -9.029 -1.261 1.130  H9   FR5 60 
FR5 H15  H15  H 0 1 N N N 46.480 48.605 21.591 -6.719 -1.729 1.767  H15  FR5 61 
FR5 H11  H11  H 0 1 N N N 43.827 46.658 17.870 -7.712 1.523  -1.822 H11  FR5 62 
FR5 H17  H17  H 0 1 N N N 43.014 46.443 20.326 -9.532 0.355  -0.653 H17  FR5 63 
FR5 H71  1H7  H 0 1 N N N 44.960 47.781 15.736 -4.637 1.506  -3.151 H71  FR5 64 
FR5 H72  2H7  H 0 1 N N N 46.575 47.647 14.990 -5.574 2.704  -2.227 H72  FR5 65 
FR5 H73  3H7  H 0 1 N N N 45.901 46.331 15.989 -3.815 2.574  -1.988 H73  FR5 66 
# 
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 
FR5 C1  N2   SING Y N 1  
FR5 C1  C5   DOUB Y N 2  
FR5 C1  H1   SING N N 3  
FR5 N2  C3   SING Y N 4  
FR5 N2  C13  SING N N 5  
FR5 C3  N4   DOUB Y N 6  
FR5 C3  H3   SING N N 7  
FR5 N4  C5   SING Y N 8  
FR5 C5  C8   SING N N 9  
FR5 C8  O9   DOUB N N 10 
FR5 C8  N10  SING N N 11 
FR5 N10 H101 SING N N 12 
FR5 N10 H102 SING N N 13 
FR5 C13 C14  SING N N 14 
FR5 C13 C18  SING N N 15 
FR5 C13 H13  SING N N 16 
FR5 C14 O15  SING N N 17 
FR5 C14 H141 SING N N 18 
FR5 C14 H142 SING N N 19 
FR5 O15 H15O SING N N 20 
FR5 C18 C19  SING N N 21 
FR5 C18 H181 SING N N 22 
FR5 C18 H182 SING N N 23 
FR5 C19 N22  SING N N 24 
FR5 C19 H191 SING N N 25 
FR5 C19 H192 SING N N 26 
FR5 N22 C27  SING Y N 27 
FR5 N22 C30  SING Y N 28 
FR5 C27 C28  DOUB Y N 29 
FR5 C27 H27  SING N N 30 
FR5 C28 C29  SING Y N 31 
FR5 C28 H28  SING N N 32 
FR5 C29 C30  DOUB Y N 33 
FR5 C29 C31  SING Y N 34 
FR5 C30 C34  SING Y N 35 
FR5 C31 C32  DOUB Y N 36 
FR5 C31 H31  SING N N 37 
FR5 C32 C33  SING Y N 38 
FR5 C32 H32  SING N N 39 
FR5 C33 C34  DOUB Y N 40 
FR5 C33 N1   SING N N 41 
FR5 C34 H34  SING N N 42 
FR5 N1  C2   SING N N 43 
FR5 N1  HN1  SING N N 44 
FR5 C2  O1   DOUB N N 45 
FR5 C2  C4   SING N N 46 
FR5 C4  C6   SING N N 47 
FR5 C4  H41  SING N N 48 
FR5 C4  H42  SING N N 49 
FR5 C6  C12  SING N N 50 
FR5 C6  H61  SING N N 51 
FR5 C6  H62  SING N N 52 
FR5 C9  C15  DOUB Y N 53 
FR5 C9  C17  SING Y N 54 
FR5 C9  H9   SING N N 55 
FR5 C15 C10  SING Y N 56 
FR5 C15 H15  SING N N 57 
FR5 C10 C16  DOUB Y N 58 
FR5 C10 N11  SING Y N 59 
FR5 C16 C11  SING Y N 60 
FR5 C16 N13  SING Y N 61 
FR5 C11 C17  DOUB Y N 62 
FR5 C11 H11  SING N N 63 
FR5 C17 H17  SING N N 64 
FR5 N11 C12  DOUB Y N 65 
FR5 C12 N13  SING Y N 66 
FR5 N13 C7   SING N N 67 
FR5 C7  H71  SING N N 68 
FR5 C7  H72  SING N N 69 
FR5 C7  H73  SING N N 70 
# 
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 
FR5 SMILES           ACDLabs              10.04 O=C(N)c1ncn(c1)C(CO)CCn3c2cc(ccc2cc3)NC(=O)CCc4nc5ccccc5n4C 
FR5 InChI            InChI                1.02b 
InChI=1/C27H29N7O3/c1-32-23-5-3-2-4-21(23)31-25(32)8-9-26(36)30-19-7-6-18-10-12-33(24(18)14-19)13-11-20(16-35)34-15-22(27(28)37)29-17-34/h2-7,10,12,14-15,17,20,35H,8-9,11,13,16H2,1H3,(H2,28,37)(H,30,36)/t20-/m1/s1/f/h30H,28H2 
FR5 InChIKey         InChI                1.02b MBHAURHGCAJBCN-DDKAGDHGDJ 
FR5 SMILES_CANONICAL CACTVS               3.341 Cn1c(CCC(=O)Nc2ccc3ccn(CC[C@H](CO)n4cnc(c4)C(N)=O)c3c2)nc5ccccc15 
FR5 SMILES           CACTVS               3.341 Cn1c(CCC(=O)Nc2ccc3ccn(CC[CH](CO)n4cnc(c4)C(N)=O)c3c2)nc5ccccc15 
FR5 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cn1c2ccccc2nc1CCC(=O)Nc3ccc4ccn(c4c3)CC[C@H](CO)n5cc(nc5)C(=O)N 
FR5 SMILES           "OpenEye OEToolkits" 1.5.0 Cn1c2ccccc2nc1CCC(=O)Nc3ccc4ccn(c4c3)CCC(CO)n5cc(nc5)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 
FR5 "SYSTEMATIC NAME" ACDLabs              10.04 1-[(1R)-1-(hydroxymethyl)-3-(6-{[3-(1-methyl-1H-benzimidazol-2-yl)propanoyl]amino}-1H-indol-1-yl)propyl]-1H-imidazole-4-carboxamide 
FR5 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 1-[(2R)-1-hydroxy-4-[6-[3-(1-methylbenzimidazol-2-yl)propanoylamino]indol-1-yl]butan-2-yl]imidazole-4-carboxamide                   
# 
