data_FRG # _chem_comp.id FRG _chem_comp.name "2-[3-METHYL-4-(N-METHYL-GUANIDINO)-BUTYRYLAMINO]-3-(4-PHENYLETHYNYL-PHENYL)-PROPIONIC ACID METHYL ESTER" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C26 H30 N4 O3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "(R)-N-[2-[1-(AMINOIMINOMETHYL)-3-PIPERIDINYL]-1-OXOETHYL]-4-(PHENYLETHYNYL)-L-PHENYLALANINE METHYL ESTER" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2002-07-03 _chem_comp.pdbx_modified_date 2021-03-01 _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 446.541 _chem_comp.one_letter_code ? _chem_comp.three_letter_code FRG _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 1M48 _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 FRG N33 N33 N 0 1 N N N 3.080 -17.462 27.275 2.853 -3.063 -2.597 N33 FRG 1 FRG C31 C31 C 0 1 N N N 3.312 -16.734 28.356 3.249 -3.931 -1.709 C31 FRG 2 FRG N32 N32 N 0 1 N N N 4.448 -16.008 28.438 3.895 -5.077 -2.107 N32 FRG 3 FRG N29 N29 N 0 1 N N N 2.320 -16.638 29.382 3.021 -3.699 -0.373 N29 FRG 4 FRG C30 C30 C 0 1 N N N 2.641 -15.638 30.414 2.438 -2.428 0.077 C30 FRG 5 FRG C28 C28 C 0 1 N N N 1.521 -17.836 29.783 3.355 -4.719 0.631 C28 FRG 6 FRG C27 C27 C 0 1 N N N 1.773 -18.336 31.211 4.256 -4.085 1.696 C27 FRG 7 FRG C26 C26 C 0 1 N N N 1.713 -17.187 32.220 3.568 -2.842 2.266 C26 FRG 8 FRG C24 C24 C 0 1 N N R 2.739 -16.095 31.874 3.348 -1.820 1.149 C24 FRG 9 FRG C23 C23 C 0 1 N N N 2.596 -14.873 32.792 2.690 -0.565 1.726 C23 FRG 10 FRG C22 C22 C 0 1 N N N 2.929 -15.210 34.229 2.585 0.486 0.652 C22 FRG 11 FRG O25 O25 O 0 1 N N N 4.056 -15.600 34.510 2.995 0.255 -0.466 O25 FRG 12 FRG N21 N21 N 0 1 N N N 1.914 -15.065 35.097 2.034 1.684 0.933 N21 FRG 13 FRG C16 C16 C 0 1 N N S 2.041 -15.341 36.517 1.931 2.706 -0.111 C16 FRG 14 FRG C17 C17 C 0 1 N N N 1.986 -16.808 36.809 3.222 3.479 -0.186 C17 FRG 15 FRG O19 O19 O 0 1 N N N 1.415 -17.621 36.080 4.135 3.205 0.557 O19 FRG 16 FRG O18 O18 O 0 1 N N N 2.715 -17.266 37.968 3.359 4.473 -1.078 O18 FRG 17 FRG C20 C20 C 0 1 N N N 2.726 -18.645 38.356 4.603 5.218 -1.150 C20 FRG 18 FRG C15 C15 C 0 1 N N N 1.122 -14.475 37.375 0.783 3.661 0.221 C15 FRG 19 FRG C12 C12 C 0 1 Y N N 1.265 -13.011 37.283 -0.523 2.912 0.175 C12 FRG 20 FRG C13 C13 C 0 1 Y N N 0.193 -12.233 36.862 -1.007 2.300 1.318 C13 FRG 21 FRG C14 C14 C 0 1 Y N N 0.324 -10.857 36.782 -2.202 1.612 1.284 C14 FRG 22 FRG C11 C11 C 0 1 Y N N 2.494 -12.417 37.580 -1.236 2.843 -1.009 C11 FRG 23 FRG C10 C10 C 0 1 Y N N 2.645 -11.042 37.491 -2.430 2.154 -1.060 C10 FRG 24 FRG C9 C9 C 0 1 Y N N 1.549 -10.294 37.090 -2.924 1.533 0.091 C9 FRG 25 FRG C8 C8 C 0 1 N N N 1.670 -8.856 36.998 -4.165 0.820 0.047 C8 FRG 26 FRG C7 C7 C 0 1 N N N 1.743 -7.566 36.930 -5.183 0.236 0.011 C7 FRG 27 FRG C4 C4 C 0 1 Y N N 1.788 -6.125 36.877 -6.424 -0.477 -0.033 C4 FRG 28 FRG C5 C5 C 0 1 Y N N 0.834 -5.430 37.598 -7.147 -0.556 -1.227 C5 FRG 29 FRG C6 C6 C 0 1 Y N N 0.859 -4.055 37.558 -8.341 -1.244 -1.261 C6 FRG 30 FRG C3 C3 C 0 1 Y N N 2.746 -5.510 36.107 -6.915 -1.103 1.116 C3 FRG 31 FRG C2 C2 C 0 1 Y N N 2.777 -4.129 36.078 -8.114 -1.783 1.067 C2 FRG 32 FRG C1 C1 C 0 1 Y N N 1.833 -3.412 36.802 -8.824 -1.857 -0.118 C1 FRG 33 FRG H33 H33 H 0 1 N N N 2.505 -17.588 28.108 3.014 -3.227 -3.540 H33 FRG 34 FRG H321 1H32 H 0 0 N N N 4.507 -15.403 27.619 4.119 -5.759 -1.455 H321 FRG 35 FRG H322 2H32 H 0 0 N N N 4.627 -15.447 29.271 4.127 -5.203 -3.041 H322 FRG 36 FRG H301 1H30 H 0 0 N N N 1.908 -14.800 30.346 1.449 -2.608 0.499 H301 FRG 37 FRG H302 2H30 H 0 0 N N N 3.588 -15.120 30.133 2.358 -1.743 -0.767 H302 FRG 38 FRG H281 1H28 H 0 0 N N N 1.676 -18.664 29.053 3.881 -5.544 0.152 H281 FRG 39 FRG H282 2H28 H 0 0 N N N 0.434 -17.642 29.630 2.441 -5.086 1.097 H282 FRG 40 FRG H271 1H27 H 0 0 N N N 2.734 -18.896 31.285 5.207 -3.799 1.245 H271 FRG 41 FRG H272 2H27 H 0 0 N N N 1.073 -19.159 31.486 4.433 -4.802 2.497 H272 FRG 42 FRG H261 1H26 H 0 0 N N N 1.838 -17.552 33.266 4.196 -2.403 3.042 H261 FRG 43 FRG H262 2H26 H 0 0 N N N 0.683 -16.770 32.307 2.606 -3.124 2.695 H262 FRG 44 FRG H24 H24 H 0 1 N N N 3.740 -16.561 32.031 4.308 -1.556 0.704 H24 FRG 45 FRG H231 1H23 H 0 0 N N N 1.582 -14.416 32.706 3.295 -0.184 2.549 H231 FRG 46 FRG H232 2H23 H 0 0 N N N 3.205 -14.015 32.424 1.694 -0.813 2.091 H232 FRG 47 FRG H21 H21 H 0 1 N N N 1.042 -14.744 34.676 1.706 1.869 1.827 H21 FRG 48 FRG H16 H16 H 0 1 N N N 3.065 -15.027 36.828 1.739 2.227 -1.071 H16 FRG 49 FRG H201 1H20 H 0 0 N N N 3.068 -19.243 37.480 4.796 5.698 -0.190 H201 FRG 50 FRG H202 2H20 H 0 0 N N N 3.289 -18.999 39.251 5.421 4.538 -1.387 H202 FRG 51 FRG H203 3H20 H 0 0 N N N 1.667 -18.977 38.466 4.527 5.979 -1.927 H203 FRG 52 FRG H151 1H15 H 0 0 N N N 1.219 -14.785 38.442 0.931 4.073 1.219 H151 FRG 53 FRG H152 2H15 H 0 0 N N N 0.062 -14.752 37.169 0.763 4.472 -0.507 H152 FRG 54 FRG H13 H13 H 0 1 N N N -0.764 -12.709 36.591 -0.447 2.362 2.240 H13 FRG 55 FRG H14 H14 H 0 1 N N N -0.527 -10.224 36.480 -2.577 1.135 2.177 H14 FRG 56 FRG H11 H11 H 0 1 N N N 3.352 -13.038 37.887 -0.853 3.323 -1.897 H11 FRG 57 FRG H10 H10 H 0 1 N N N 3.607 -10.558 37.732 -2.983 2.097 -1.986 H10 FRG 58 FRG H5 H5 H 0 1 N N N 0.070 -5.960 38.192 -6.771 -0.078 -2.119 H5 FRG 59 FRG H6 H6 H 0 1 N N N 0.109 -3.477 38.124 -8.901 -1.305 -2.183 H6 FRG 60 FRG H3 H3 H 0 1 N N N 3.470 -6.108 35.528 -6.362 -1.046 2.041 H3 FRG 61 FRG H2 H2 H 0 1 N N N 3.545 -3.606 35.485 -8.498 -2.263 1.956 H2 FRG 62 FRG H1 H1 H 0 1 N N N 1.857 -2.310 36.776 -9.760 -2.394 -0.151 H1 FRG 63 # # 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 FRG N33 C31 DOUB N N 1 FRG N33 H33 SING N N 2 FRG C31 N32 SING N N 3 FRG C31 N29 SING N N 4 FRG N32 H321 SING N N 5 FRG N32 H322 SING N N 6 FRG N29 C30 SING N N 7 FRG N29 C28 SING N N 8 FRG C30 C24 SING N N 9 FRG C30 H301 SING N N 10 FRG C30 H302 SING N N 11 FRG C28 C27 SING N N 12 FRG C28 H281 SING N N 13 FRG C28 H282 SING N N 14 FRG C27 C26 SING N N 15 FRG C27 H271 SING N N 16 FRG C27 H272 SING N N 17 FRG C26 C24 SING N N 18 FRG C26 H261 SING N N 19 FRG C26 H262 SING N N 20 FRG C24 C23 SING N N 21 FRG C24 H24 SING N N 22 FRG C23 C22 SING N N 23 FRG C23 H231 SING N N 24 FRG C23 H232 SING N N 25 FRG C22 O25 DOUB N N 26 FRG C22 N21 SING N N 27 FRG N21 C16 SING N N 28 FRG N21 H21 SING N N 29 FRG C16 C17 SING N N 30 FRG C16 C15 SING N N 31 FRG C16 H16 SING N N 32 FRG C17 O19 DOUB N N 33 FRG C17 O18 SING N N 34 FRG O18 C20 SING N N 35 FRG C20 H201 SING N N 36 FRG C20 H202 SING N N 37 FRG C20 H203 SING N N 38 FRG C15 C12 SING N N 39 FRG C15 H151 SING N N 40 FRG C15 H152 SING N N 41 FRG C12 C13 DOUB Y N 42 FRG C12 C11 SING Y N 43 FRG C13 C14 SING Y N 44 FRG C13 H13 SING N N 45 FRG C14 C9 DOUB Y N 46 FRG C14 H14 SING N N 47 FRG C11 C10 DOUB Y N 48 FRG C11 H11 SING N N 49 FRG C10 C9 SING Y N 50 FRG C10 H10 SING N N 51 FRG C9 C8 SING N N 52 FRG C8 C7 TRIP N N 53 FRG C7 C4 SING N N 54 FRG C4 C5 DOUB Y N 55 FRG C4 C3 SING Y N 56 FRG C5 C6 SING Y N 57 FRG C5 H5 SING N N 58 FRG C6 C1 DOUB Y N 59 FRG C6 H6 SING N N 60 FRG C3 C2 DOUB Y N 61 FRG C3 H3 SING N N 62 FRG C2 C1 SING Y N 63 FRG C2 H2 SING N N 64 FRG C1 H1 SING N N 65 # # 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 FRG SMILES ACDLabs 10.04 "O=C(OC)C(NC(=O)CC1CCCN(C(=[N@H])N)C1)Cc3ccc(C#Cc2ccccc2)cc3" FRG SMILES_CANONICAL CACTVS 3.341 "COC(=O)[C@H](Cc1ccc(cc1)C#Cc2ccccc2)NC(=O)C[C@H]3CCCN(C3)C(N)=N" FRG SMILES CACTVS 3.341 "COC(=O)[CH](Cc1ccc(cc1)C#Cc2ccccc2)NC(=O)C[CH]3CCCN(C3)C(N)=N" FRG SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "[H]/N=C(/N)\N1CCC[C@@H](C1)CC(=O)N[C@@H](Cc2ccc(cc2)C#Cc3ccccc3)C(=O)OC" FRG SMILES "OpenEye OEToolkits" 1.5.0 "[H]N=C(N)N1CCCC(C1)CC(=O)NC(Cc2ccc(cc2)C#Cc3ccccc3)C(=O)OC" FRG InChI InChI 1.03 "InChI=1S/C26H30N4O3/c1-33-25(32)23(29-24(31)17-22-8-5-15-30(18-22)26(27)28)16-21-13-11-20(12-14-21)10-9-19-6-3-2-4-7-19/h2-4,6-7,11-14,22-23H,5,8,15-18H2,1H3,(H3,27,28)(H,29,31)/t22-,23+/m1/s1" FRG InChIKey InChI 1.03 MRNGXYMKYHNMLV-PKTZIBPZSA-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 FRG "SYSTEMATIC NAME" ACDLabs 10.04 "methyl N-{[(3R)-1-carbamimidoylpiperidin-3-yl]acetyl}-4-(phenylethynyl)-L-phenylalaninate" FRG "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "methyl (2S)-2-[2-[(3R)-1-carbamimidoylpiperidin-3-yl]ethanoylamino]-3-[4-(2-phenylethynyl)phenyl]propanoate" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site FRG "Create component" 2002-07-03 RCSB FRG "Modify descriptor" 2011-06-04 RCSB FRG "Modify synonyms" 2021-03-01 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id FRG _pdbx_chem_comp_synonyms.name "(R)-N-[2-[1-(AMINOIMINOMETHYL)-3-PIPERIDINYL]-1-OXOETHYL]-4-(PHENYLETHYNYL)-L-PHENYLALANINE METHYL ESTER" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##