data_FR8
# 
_chem_comp.id                                    FR8 
_chem_comp.name                                  1-((1R)-1-(HYDROXYMETHYL)-3-{6-[(5-PHENYLPENTANOYL)AMINO]-1H-INDOL-1-YL}PROPYL)-1H-IMIDAZOLE-4-CARBOXAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C27 H31 N5 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         FR235380 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-09-15 
_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                        473.567 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     FR8 
_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        1QXL 
_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 
FR8 C1   C1   C 0 1 Y N N 51.620 54.457 20.861 1.655  0.303  6.582   C1   FR8 1  
FR8 N2   N2   N 0 1 Y N N 51.742 55.429 21.949 1.229  0.515  5.315   N2   FR8 2  
FR8 C3   C3   C 0 1 Y N N 51.753 54.762 23.099 2.102  -0.099 4.476   C3   FR8 3  
FR8 N4   N4   N 0 1 Y N N 51.718 53.441 22.888 3.038  -0.667 5.181   N4   FR8 4  
FR8 C5   C5   C 0 1 Y N N 51.559 53.258 21.438 2.792  -0.444 6.498   C5   FR8 5  
FR8 C8   C8   C 0 1 N N N 51.351 51.956 20.749 3.609  -0.919 7.628   C8   FR8 6  
FR8 O9   O9   O 0 1 N N N 51.117 51.907 19.550 3.285  -0.647 8.769   O9   FR8 7  
FR8 N10  N10  N 0 1 N N N 51.462 50.856 21.452 4.715  -1.654 7.399   N10  FR8 8  
FR8 C13  C13  C 0 1 N N R 51.729 56.874 21.804 0.038  1.272  4.919   C13  FR8 9  
FR8 C14  C14  C 0 1 N N N 53.172 57.471 21.748 0.453  2.448  4.034   C14  FR8 10 
FR8 O15  O15  O 0 1 N N N 54.017 56.809 22.780 1.115  1.956  2.866   O15  FR8 11 
FR8 C18  C18  C 0 1 N N N 50.883 57.258 20.573 -0.911 0.359  4.142   C18  FR8 12 
FR8 C19  C19  C 0 1 N N N 49.353 57.120 20.808 -2.154 1.149  3.729   C19  FR8 13 
FR8 N22  N22  N 0 1 Y N N 48.680 57.387 19.505 -3.064 0.274  2.984   N22  FR8 14 
FR8 C27  C27  C 0 1 Y N N 48.079 58.551 19.100 -4.056 -0.485 3.543   C27  FR8 15 
FR8 C28  C28  C 0 1 Y N N 47.598 58.398 17.800 -4.703 -1.167 2.585   C28  FR8 16 
FR8 C29  C29  C 0 1 Y N N 47.919 57.063 17.384 -4.075 -0.815 1.309   C29  FR8 17 
FR8 C30  C30  C 0 1 Y N N 48.583 56.451 18.491 -3.052 0.099  1.619   C30  FR8 18 
FR8 C31  C31  C 0 1 Y N N 47.707 56.365 16.233 -4.299 -1.191 -0.017  C31  FR8 19 
FR8 C32  C32  C 0 1 Y N N 48.152 55.050 16.129 -3.519 -0.672 -1.011  C32  FR8 20 
FR8 C33  C33  C 0 1 Y N N 48.810 54.438 17.231 -2.501 0.230  -0.712  C33  FR8 21 
FR8 C34  C34  C 0 1 Y N N 49.005 55.164 18.398 -2.264 0.614  0.596   C34  FR8 22 
FR8 N1   N1   N 0 1 N N N 49.328 53.194 17.231 -1.711 0.752  -1.743  N1   FR8 23 
FR8 C2   C2   C 0 1 N N N 49.043 52.248 16.338 -1.335 -0.035 -2.770  C2   FR8 24 
FR8 O1   O1   O 0 1 N N N 48.427 52.384 15.302 -1.596 -1.219 -2.752  O1   FR8 25 
FR8 C4   C4   C 0 1 N N N 49.566 50.908 16.770 -0.592 0.555  -3.940  C4   FR8 26 
FR8 C6   C6   C 0 1 N N N 48.451 49.873 16.875 -0.287 -0.545 -4.958  C6   FR8 27 
FR8 C7   C7   C 0 1 Y N N 46.397 47.167 16.255 2.897  -0.406 -8.322  C7   FR8 28 
FR8 C11  C11  C 0 1 Y N N 46.807 47.460 17.556 1.515  -0.456 -8.335  C11  FR8 29 
FR8 C9   C9   C 0 1 Y N N 45.877 47.577 18.571 0.816  0.030  -9.424  C9   FR8 30 
FR8 C12  C12  C 0 1 Y N N 44.555 47.289 18.295 1.498  0.575  -10.496 C12  FR8 31 
FR8 C10  C10  C 0 1 Y N N 44.159 46.937 17.008 2.880  0.626  -10.482 C10  FR8 32 
FR8 C15  C15  C 0 1 Y N N 45.068 46.899 15.967 3.579  0.135  -9.395  C15  FR8 33 
FR8 C16  C16  C 0 1 N N N 48.629 49.029 18.125 0.467  0.053  -6.146  C16  FR8 34 
FR8 C17  C17  C 0 1 N N N 48.244 47.590 17.867 0.772  -1.046 -7.165  C17  FR8 35 
FR8 H1   H1   H 0 1 N N N 51.580 54.606 19.769 1.184  0.657  7.487   H1   FR8 36 
FR8 H3   H3   H 0 1 N N N 51.787 55.240 24.093 2.035  -0.111 3.399   H3   FR8 37 
FR8 H101 1H10 H 0 0 N N N 51.319 49.963 20.980 5.253  -1.966 8.143   H101 FR8 38 
FR8 H102 2H10 H 0 0 N N N 51.657 50.897 22.452 4.971  -1.874 6.490   H102 FR8 39 
FR8 H13  H13  H 0 1 N N N 51.256 57.322 22.709 -0.465 1.648  5.810   H13  FR8 40 
FR8 H141 1H14 H 0 0 N N N 53.175 58.582 21.848 -0.431 3.012  3.739   H141 FR8 41 
FR8 H142 2H14 H 0 0 N N N 53.619 57.403 20.729 1.130  3.099  4.587   H142 FR8 42 
FR8 H15  H15  H 0 1 N N N 54.894 57.172 22.746 1.359  2.727  2.337   H15  FR8 43 
FR8 H181 1H18 H 0 0 N N N 51.200 56.674 19.678 -1.206 -0.479 4.773   H181 FR8 44 
FR8 H182 2H18 H 0 0 N N N 51.138 58.285 20.223 -0.406 -0.016 3.252   H182 FR8 45 
FR8 H191 1H19 H 0 0 N N N 48.978 57.769 21.634 -1.858 1.987  3.098   H191 FR8 46 
FR8 H192 2H19 H 0 0 N N N 49.067 56.139 21.254 -2.658 1.525  4.619   H192 FR8 47 
FR8 H27  H27  H 0 1 N N N 47.996 59.461 19.718 -4.284 -0.530 4.597   H27  FR8 48 
FR8 H28  H28  H 0 1 N N N 47.071 59.174 17.220 -5.531 -1.847 2.728   H28  FR8 49 
FR8 H31  H31  H 0 1 N N N 47.182 56.858 15.397 -5.086 -1.890 -0.255  H31  FR8 50 
FR8 H32  H32  H 0 1 N N N 47.986 54.501 15.187 -3.694 -0.964 -2.036  H32  FR8 51 
FR8 H34  H34  H 0 1 N N N 49.506 54.709 19.269 -1.473 1.314  0.820   H34  FR8 52 
FR8 HN1  HN1  H 0 1 N N N 49.990 52.948 17.967 -1.434 1.682  -1.718  HN1  FR8 53 
FR8 H41  1H4  H 0 1 N N N 50.141 50.984 17.723 0.341  0.996  -3.592  H41  FR8 54 
FR8 H42  2H4  H 0 1 N N N 50.385 50.556 16.100 -1.205 1.324  -4.409  H42  FR8 55 
FR8 H61  1H6  H 0 1 N N N 48.379 49.245 15.957 -1.221 -0.986 -5.307  H61  FR8 56 
FR8 H62  2H6  H 0 1 N N N 47.441 50.344 16.832 0.325  -1.315 -4.489  H62  FR8 57 
FR8 H7   H7   H 0 1 N N N 47.138 47.147 15.438 3.443  -0.789 -7.473  H7   FR8 58 
FR8 H9   H9   H 0 1 N N N 46.184 47.894 19.582 -0.262 -0.009 -9.434  H9   FR8 59 
FR8 H12  H12  H 0 1 N N N 43.811 47.340 19.108 0.952  0.959  -11.344 H12  FR8 60 
FR8 H10  H10  H 0 1 N N N 43.104 46.683 16.809 3.413  1.050  -11.320 H10  FR8 61 
FR8 H2   H2   H 0 1 N N N 44.743 46.663 14.940 4.658  0.175  -9.385  H2   FR8 62 
FR8 H161 1H16 H 0 0 N N N 48.071 49.455 18.992 1.401  0.495  -5.798  H161 FR8 63 
FR8 H162 2H16 H 0 0 N N N 49.664 49.111 18.533 -0.145 0.823  -6.616  H162 FR8 64 
FR8 H171 1H17 H 0 0 N N N 48.876 47.136 17.069 1.385  -1.816 -6.696  H171 FR8 65 
FR8 H172 2H17 H 0 0 N N N 48.538 46.931 18.717 -0.161 -1.488 -7.513  H172 FR8 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 
FR8 C1  N2   SING Y N 1  
FR8 C1  C5   DOUB Y N 2  
FR8 C1  H1   SING N N 3  
FR8 N2  C3   SING Y N 4  
FR8 N2  C13  SING N N 5  
FR8 C3  N4   DOUB Y N 6  
FR8 C3  H3   SING N N 7  
FR8 N4  C5   SING Y N 8  
FR8 C5  C8   SING N N 9  
FR8 C8  O9   DOUB N N 10 
FR8 C8  N10  SING N N 11 
FR8 N10 H101 SING N N 12 
FR8 N10 H102 SING N N 13 
FR8 C13 C14  SING N N 14 
FR8 C13 C18  SING N N 15 
FR8 C13 H13  SING N N 16 
FR8 C14 O15  SING N N 17 
FR8 C14 H141 SING N N 18 
FR8 C14 H142 SING N N 19 
FR8 O15 H15  SING N N 20 
FR8 C18 C19  SING N N 21 
FR8 C18 H181 SING N N 22 
FR8 C18 H182 SING N N 23 
FR8 C19 N22  SING N N 24 
FR8 C19 H191 SING N N 25 
FR8 C19 H192 SING N N 26 
FR8 N22 C27  SING Y N 27 
FR8 N22 C30  SING Y N 28 
FR8 C27 C28  DOUB Y N 29 
FR8 C27 H27  SING N N 30 
FR8 C28 C29  SING Y N 31 
FR8 C28 H28  SING N N 32 
FR8 C29 C30  DOUB Y N 33 
FR8 C29 C31  SING Y N 34 
FR8 C30 C34  SING Y N 35 
FR8 C31 C32  DOUB Y N 36 
FR8 C31 H31  SING N N 37 
FR8 C32 C33  SING Y N 38 
FR8 C32 H32  SING N N 39 
FR8 C33 C34  DOUB Y N 40 
FR8 C33 N1   SING N N 41 
FR8 C34 H34  SING N N 42 
FR8 N1  C2   SING N N 43 
FR8 N1  HN1  SING N N 44 
FR8 C2  O1   DOUB N N 45 
FR8 C2  C4   SING N N 46 
FR8 C4  C6   SING N N 47 
FR8 C4  H41  SING N N 48 
FR8 C4  H42  SING N N 49 
FR8 C6  C16  SING N N 50 
FR8 C6  H61  SING N N 51 
FR8 C6  H62  SING N N 52 
FR8 C7  C11  DOUB Y N 53 
FR8 C7  C15  SING Y N 54 
FR8 C7  H7   SING N N 55 
FR8 C11 C9   SING Y N 56 
FR8 C11 C17  SING N N 57 
FR8 C9  C12  DOUB Y N 58 
FR8 C9  H9   SING N N 59 
FR8 C12 C10  SING Y N 60 
FR8 C12 H12  SING N N 61 
FR8 C10 C15  DOUB Y N 62 
FR8 C10 H10  SING N N 63 
FR8 C15 H2   SING N N 64 
FR8 C16 C17  SING N N 65 
FR8 C16 H161 SING N N 66 
FR8 C16 H162 SING N N 67 
FR8 C17 H171 SING N N 68 
FR8 C17 H172 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 
FR8 SMILES           ACDLabs              10.04 O=C(N)c1ncn(c1)C(CO)CCn3c2cc(ccc2cc3)NC(=O)CCCCc4ccccc4 
FR8 InChI            InChI                1.02b 
InChI=1/C27H31N5O3/c28-27(35)24-17-32(19-29-24)23(18-33)13-15-31-14-12-21-10-11-22(16-25(21)31)30-26(34)9-5-4-8-20-6-2-1-3-7-20/h1-3,6-7,10-12,14,16-17,19,23,33H,4-5,8-9,13,15,18H2,(H2,28,35)(H,30,34)/t23-/m1/s1/f/h30H,28H2 
FR8 InChIKey         InChI                1.02b SLLHIZOLSGWMLR-GPYZWRGKDM 
FR8 SMILES_CANONICAL CACTVS               3.341 NC(=O)c1cn(cn1)[C@@H](CO)CCn2ccc3ccc(NC(=O)CCCCc4ccccc4)cc23 
FR8 SMILES           CACTVS               3.341 NC(=O)c1cn(cn1)[CH](CO)CCn2ccc3ccc(NC(=O)CCCCc4ccccc4)cc23 
FR8 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)CCCCC(=O)Nc2ccc3ccn(c3c2)CC[C@H](CO)n4cc(nc4)C(=O)N 
FR8 SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)CCCCC(=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 
FR8 "SYSTEMATIC NAME" ACDLabs              10.04 1-[(1R)-1-(hydroxymethyl)-3-{6-[(5-phenylpentanoyl)amino]-1H-indol-1-yl}propyl]-1H-imidazole-4-carboxamide 
FR8 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 1-[(2R)-1-hydroxy-4-[6-(5-phenylpentanoylamino)indol-1-yl]butan-2-yl]imidazole-4-carboxamide               
# 
