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 2020-05-27 _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 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" FR4 InChI InChI 1.03 "InChI=1S/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" FR4 InChIKey InChI 1.03 GUYYFMCFEPDDFL-OAQYLSRUSA-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" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site FR4 "Create component" 2003-10-05 RCSB FR4 "Modify descriptor" 2011-06-04 RCSB FR4 "Modify synonyms" 2020-05-27 PDBE # loop_ _pdbx_chem_comp_synonyms.ordinal _pdbx_chem_comp_synonyms.comp_id _pdbx_chem_comp_synonyms.name _pdbx_chem_comp_synonyms.provenance _pdbx_chem_comp_synonyms.type 1 FR4 "1-((1R)-1-(HYDROXYMETHYL)-3-{6-[(3-PHENYLPROPYL)AMINO]-1H-INDOL-1-YL}-1H-IMIDAZOLE-4-CARBOXAMIDE" ? ? 2 FR4 FR233624 ? ? #