data_FR4
# 
_chem_comp.id                                    FR4 
_chem_comp.name                                  1-((1R)-1-(HYDROXYMETHYL)-3-{6-[(3-PHENYLPROPANOYL)AMINO]-1H-INDOL-1-YL}PROPYL)-1H-IMIDAZOLE-4-CARBOXAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C25 H27 N5 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "1-((1R)-1-(HYDROXYMETHYL)-3-{6-[(3-PHENYLPROPYL)AMINO]-1H-INDOL-1-YL}-1H-IMIDAZOLE-4-CARBOXAMIDE, FR233624" 
_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                        445.514 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     FR4 
_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        ? 
_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 
FR4 C1   C1   C 0 1 Y N N 51.887 54.593 20.767 0.923  0.483  6.250  C1   FR4 1  
FR4 N2   N2   N 0 1 Y N N 51.845 55.624 21.769 0.831  0.500  4.899  N2   FR4 2  
FR4 C3   C3   C 0 1 Y N N 51.736 54.959 22.916 1.701  -0.423 4.414  C3   FR4 3  
FR4 N4   N4   N 0 1 Y N N 51.729 53.649 22.785 2.316  -0.991 5.411  N4   FR4 4  
FR4 C5   C5   C 0 1 Y N N 51.729 53.416 21.408 1.856  -0.458 6.572  C5   FR4 5  
FR4 C8   C8   C 0 1 N N N 51.620 52.031 20.895 2.290  -0.825 7.931  C8   FR4 6  
FR4 O9   O9   O 0 1 N N N 51.494 51.840 19.720 1.803  -0.267 8.896  O9   FR4 7  
FR4 N10  N10  N 0 1 N N N 51.643 50.999 21.714 3.226  -1.779 8.105  N10  FR4 8  
FR4 C13  C13  C 0 1 N N R 52.001 57.079 21.629 -0.048 1.360  4.104  C13  FR4 9  
FR4 C14  C14  C 0 1 N N N 53.533 57.579 21.521 0.796  2.231  3.172  C14  FR4 10 
FR4 O15  O15  O 0 1 N N N 54.430 57.170 22.650 1.560  1.395  2.300  O15  FR4 11 
FR4 C18  C18  C 0 1 N N N 51.171 57.598 20.477 -0.994 0.491  3.272  C18  FR4 12 
FR4 C19  C19  C 0 1 N N N 49.700 57.288 20.686 -1.912 1.389  2.442  C19  FR4 13 
FR4 N22  N22  N 0 1 Y N N 49.040 57.374 19.380 -2.818 0.557  1.645  N22  FR4 14 
FR4 C27  C27  C 0 1 Y N N 48.547 58.509 18.827 -4.051 0.122  2.054  C27  FR4 15 
FR4 C28  C28  C 0 1 Y N N 48.117 58.310 17.501 -4.619 -0.615 1.088  C28  FR4 16 
FR4 C29  C29  C 0 1 Y N N 48.340 56.908 17.298 -3.674 -0.657 -0.031 C29  FR4 17 
FR4 C30  C30  C 0 1 Y N N 48.968 56.370 18.480 -2.560 0.102  0.372  C30  FR4 18 
FR4 C31  C31  C 0 1 Y N N 48.153 56.142 16.194 -3.693 -1.254 -1.293 C31  FR4 19 
FR4 C32  C32  C 0 1 Y N N 48.511 54.798 16.290 -2.626 -1.104 -2.132 C32  FR4 20 
FR4 C33  C33  C 0 1 Y N N 49.147 54.275 17.444 -1.517 -0.358 -1.739 C33  FR4 21 
FR4 C34  C34  C 0 1 Y N N 49.313 55.048 18.569 -1.480 0.241  -0.492 C34  FR4 22 
FR4 N1   N1   N 0 1 N N N 49.557 53.013 17.550 -0.432 -0.213 -2.611 N1   FR4 23 
FR4 C2   C2   C 0 1 N N N 49.234 51.944 16.771 -0.640 -0.153 -3.941 C2   FR4 24 
FR4 O1   O1   O 0 1 N N N 48.617 52.001 15.721 -1.772 -0.124 -4.377 O1   FR4 25 
FR4 C4   C4   C 0 1 N N N 49.784 50.673 17.323 0.532  -0.122 -4.887 C4   FR4 26 
FR4 C6   C6   C 0 1 N N N 49.340 49.460 16.563 0.023  -0.055 -6.329 C6   FR4 27 
FR4 C7   C7   C 0 1 Y N N 47.671 49.050 18.501 1.723  -1.206 -7.760 C7   FR4 28 
FR4 C11  C11  C 0 1 Y N N 47.991 48.978 17.102 1.196  -0.024 -7.274 C11  FR4 29 
FR4 C9   C9   C 0 1 Y N N 47.064 48.408 16.236 1.741  1.185  -7.660 C9   FR4 30 
FR4 C12  C12  C 0 1 Y N N 45.875 47.889 16.768 2.819  1.214  -8.525 C12  FR4 31 
FR4 C10  C10  C 0 1 Y N N 45.581 47.962 18.166 3.347  0.032  -9.010 C10  FR4 32 
FR4 C15  C15  C 0 1 Y N N 46.473 48.564 19.018 2.799  -1.177 -8.628 C15  FR4 33 
FR4 H1   H1   H 0 1 N N N 52.020 54.690 19.676 0.365  1.098  6.941  H1   FR4 34 
FR4 H3   H3   H 0 1 N N N 51.658 55.455 23.898 1.860  -0.647 3.370  H3   FR4 35 
FR4 H101 1H10 H 0 0 N N N 51.568 50.045 21.361 3.512  -2.021 9.000  H101 FR4 36 
FR4 H102 2H10 H 0 0 N N N 51.750 51.162 22.715 3.611  -2.227 7.335  H102 FR4 37 
FR4 H13  H13  H 0 1 N N N 51.620 57.516 22.581 -0.630 1.998  4.769  H13  FR4 38 
FR4 H141 1H14 H 0 0 N N N 53.564 58.686 21.392 0.141  2.871  2.580  H141 FR4 39 
FR4 H142 2H14 H 0 0 N N N 53.972 57.254 20.549 1.470  2.850  3.764  H142 FR4 40 
FR4 H15  H15  H 0 1 N N N 55.331 57.464 22.587 2.076  1.982  1.731  H15  FR4 41 
FR4 H181 1H18 H 0 0 N N N 51.538 57.211 19.498 -1.595 -0.128 3.936  H181 FR4 42 
FR4 H182 2H18 H 0 0 N N N 51.342 58.686 20.304 -0.411 -0.146 2.608  H182 FR4 43 
FR4 H191 1H19 H 0 0 N N N 49.224 57.939 21.457 -1.311 2.010  1.777  H191 FR4 44 
FR4 H192 2H19 H 0 0 N N N 49.530 56.311 21.195 -2.495 2.027  3.106  H192 FR4 45 
FR4 H27  H27  H 0 1 N N N 48.502 59.463 19.380 -4.499 0.340  3.012  H27  FR4 46 
FR4 H28  H28  H 0 1 N N N 47.710 59.059 16.801 -5.588 -1.090 1.128  H28  FR4 47 
FR4 H31  H31  H 0 1 N N N 47.735 56.585 15.274 -4.549 -1.835 -1.604 H31  FR4 48 
FR4 H32  H32  H 0 1 N N N 48.287 54.136 15.437 -2.642 -1.567 -3.108 H32  FR4 49 
FR4 H34  H34  H 0 1 N N N 49.708 54.624 19.507 -0.617 0.818  -0.193 H34  FR4 50 
FR4 HN1  HN1  H 0 1 N N N 50.199 52.844 18.325 0.469  -0.156 -2.259 HN1  FR4 51 
FR4 H41  1H4  H 0 1 N N N 49.542 50.573 18.407 1.129  -1.024 -4.755 H41  FR4 52 
FR4 H42  2H4  H 0 1 N N N 50.896 50.716 17.387 1.145  0.753  -4.677 H42  FR4 53 
FR4 H61  1H6  H 0 1 N N N 50.109 48.653 16.574 -0.574 0.846  -6.461 H61  FR4 54 
FR4 H62  2H6  H 0 1 N N N 49.312 49.641 15.463 -0.589 -0.931 -6.539 H62  FR4 55 
FR4 H7   H7   H 0 1 N N N 48.381 49.501 19.214 1.295  -2.151 -7.462 H7   FR4 56 
FR4 H9   H9   H 0 1 N N N 47.267 48.369 15.153 1.328  2.109  -7.281 H9   FR4 57 
FR4 H12  H12  H 0 1 N N N 45.159 47.416 16.075 3.248  2.159  -8.823 H12  FR4 58 
FR4 H10  H10  H 0 1 N N N 44.652 47.548 18.594 4.188  0.054  -9.687 H10  FR4 59 
FR4 H2   H2   H 0 1 N N N 46.233 48.655 20.091 3.212  -2.101 -9.007 H2   FR4 60 
# 
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 
FR4 C1  N2   SING Y N 1  
FR4 C1  C5   DOUB Y N 2  
FR4 C1  H1   SING N N 3  
FR4 N2  C3   SING Y N 4  
FR4 N2  C13  SING N N 5  
FR4 C3  N4   DOUB Y N 6  
FR4 C3  H3   SING N N 7  
FR4 N4  C5   SING Y N 8  
FR4 C5  C8   SING N N 9  
FR4 C8  O9   DOUB N N 10 
FR4 C8  N10  SING N N 11 
FR4 N10 H101 SING N N 12 
FR4 N10 H102 SING N N 13 
FR4 C13 C14  SING N N 14 
FR4 C13 C18  SING N N 15 
FR4 C13 H13  SING N N 16 
FR4 C14 O15  SING N N 17 
FR4 C14 H141 SING N N 18 
FR4 C14 H142 SING N N 19 
FR4 O15 H15  SING N N 20 
FR4 C18 C19  SING N N 21 
FR4 C18 H181 SING N N 22 
FR4 C18 H182 SING N N 23 
FR4 C19 N22  SING N N 24 
FR4 C19 H191 SING N N 25 
FR4 C19 H192 SING N N 26 
FR4 N22 C27  SING Y N 27 
FR4 N22 C30  SING Y N 28 
FR4 C27 C28  DOUB Y N 29 
FR4 C27 H27  SING N N 30 
FR4 C28 C29  SING Y N 31 
FR4 C28 H28  SING N N 32 
FR4 C29 C30  DOUB Y N 33 
FR4 C29 C31  SING Y N 34 
FR4 C30 C34  SING Y N 35 
FR4 C31 C32  DOUB Y N 36 
FR4 C31 H31  SING N N 37 
FR4 C32 C33  SING Y N 38 
FR4 C32 H32  SING N N 39 
FR4 C33 C34  DOUB Y N 40 
FR4 C33 N1   SING N N 41 
FR4 C34 H34  SING N N 42 
FR4 N1  C2   SING N N 43 
FR4 N1  HN1  SING N N 44 
FR4 C2  O1   DOUB N N 45 
FR4 C2  C4   SING N N 46 
FR4 C4  C6   SING N N 47 
FR4 C4  H41  SING N N 48 
FR4 C4  H42  SING N N 49 
FR4 C6  C11  SING N N 50 
FR4 C6  H61  SING N N 51 
FR4 C6  H62  SING N N 52 
FR4 C7  C11  DOUB Y N 53 
FR4 C7  C15  SING Y N 54 
FR4 C7  H7   SING N N 55 
FR4 C11 C9   SING Y N 56 
FR4 C9  C12  DOUB Y N 57 
FR4 C9  H9   SING N N 58 
FR4 C12 C10  SING Y N 59 
FR4 C12 H12  SING N N 60 
FR4 C10 C15  DOUB Y N 61 
FR4 C10 H10  SING N N 62 
FR4 C15 H2   SING N N 63 
# 
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 
FR4 SMILES           ACDLabs              10.04 O=C(N)c1ncn(c1)C(CO)CCn3c2cc(ccc2cc3)NC(=O)CCc4ccccc4 
FR4 InChI            InChI                1.02b 
InChI=1/C25H27N5O3/c26-25(33)22-15-30(17-27-22)21(16-31)11-13-29-12-10-19-7-8-20(14-23(19)29)28-24(32)9-6-18-4-2-1-3-5-18/h1-5,7-8,10,12,14-15,17,21,31H,6,9,11,13,16H2,(H2,26,33)(H,28,32)/t21-/m1/s1/f/h28H,26H2 
FR4 InChIKey         InChI                1.02b GUYYFMCFEPDDFL-UFEXPBHCDK 
FR4 SMILES_CANONICAL CACTVS               3.341 NC(=O)c1cn(cn1)[C@@H](CO)CCn2ccc3ccc(NC(=O)CCc4ccccc4)cc23 
FR4 SMILES           CACTVS               3.341 NC(=O)c1cn(cn1)[CH](CO)CCn2ccc3ccc(NC(=O)CCc4ccccc4)cc23 
FR4 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)CCC(=O)Nc2ccc3ccn(c3c2)CC[C@H](CO)n4cc(nc4)C(=O)N 
FR4 SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)CCC(=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 
FR4 "SYSTEMATIC NAME" ACDLabs              10.04 1-[(1R)-1-(hydroxymethyl)-3-{6-[(3-phenylpropanoyl)amino]-1H-indol-1-yl}propyl]-1H-imidazole-4-carboxamide 
FR4 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 1-[(2R)-1-hydroxy-4-[6-(3-phenylpropanoylamino)indol-1-yl]butan-2-yl]imidazole-4-carboxamide               
# 
