data_13U # _chem_comp.id 13U _chem_comp.name "N-cyclooctylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C23 H35 N5 O2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "(2S)-N-[(4-carbamimidoylphenyl)methyl]-1-[2-(cyclooctylamino)ethanoyl]pyrrolidine-2-carboxamide" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2008-02-06 _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 413.556 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 13U _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details Corina _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 2ZHE _chem_comp.pdbx_subcomponent_list "CNG PRO 00S" _chem_comp.pdbx_processing_site PDBJ # # 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 13U C14 C14 C 0 1 N N N 18.243 -13.928 22.166 -1.667 0.699 -0.185 C14 CNG 1 13U O32 O32 O 0 1 N N N 17.188 -13.420 22.538 -1.004 -0.287 0.057 O32 CNG 2 13U C5 C5 C 0 1 N N N 18.954 -15.244 22.511 -3.169 0.599 -0.255 C5 CNG 3 13U N21 N21 N 0 1 N N N 18.694 -15.931 23.746 -3.580 -0.787 0.004 N21 CNG 4 13U C49 C49 C 0 1 N N N 19.328 -15.780 25.040 -5.041 -0.923 -0.057 C49 CNG 5 13U C48 C48 C 0 1 N N N 18.965 -14.465 25.718 -5.477 -2.123 0.786 C48 CNG 6 13U C47 C47 C 0 1 N N N 19.990 -13.666 26.518 -6.554 -1.684 1.780 C47 CNG 7 13U C46 C46 C 0 1 N N N 21.085 -12.678 26.131 -7.885 -1.512 1.046 C46 CNG 8 13U C45 C45 C 0 1 N N N 22.025 -13.028 24.981 -7.862 -0.207 0.248 C45 CNG 9 13U C44 C44 C 0 1 N N N 22.646 -14.413 25.084 -7.882 -0.523 -1.249 C44 CNG 10 13U C43 C43 C 0 1 N N N 22.010 -15.644 24.454 -6.908 -1.666 -1.541 C43 CNG 11 13U C42 C42 C 0 1 N N N 20.744 -16.325 24.945 -5.474 -1.135 -1.509 C42 CNG 12 13U N1 N1 N 0 1 N N N 18.888 -13.128 21.294 -1.060 1.885 -0.391 N PRO 13 13U C1 C1 C 0 1 N N S 18.395 -11.869 20.860 0.397 2.107 -0.445 CA PRO 14 13U C7 C7 C 0 1 N N N 17.016 -11.788 20.278 1.099 1.228 0.557 C PRO 15 13U O22 O22 O 0 1 N N N 16.540 -12.774 19.728 0.530 0.896 1.576 O PRO 16 13U C2 C2 C 0 1 N N N 19.396 -11.421 19.814 0.584 3.600 -0.078 CB PRO 17 13U C3 C3 C 0 1 N N N 20.542 -12.396 19.701 -0.647 4.247 -0.766 CG PRO 18 13U C4 C4 C 0 1 N N N 20.108 -13.572 20.546 -1.741 3.171 -0.600 CD PRO 19 13U N23 N23 N 0 1 N N N 16.246 -10.742 20.324 2.357 0.807 0.320 N23 00S 20 13U C24 C24 C 0 1 N N N 14.912 -10.695 19.867 3.037 -0.052 1.292 C16 00S 21 13U C25 C25 C 0 1 Y N N 13.891 -10.637 20.943 4.421 -0.379 0.792 C17 00S 22 13U C30 C30 C 0 1 Y N N 13.290 -9.427 21.270 4.624 -1.503 0.011 C22 00S 23 13U C29 C29 C 0 1 Y N N 12.342 -9.373 22.271 5.888 -1.803 -0.455 C21 00S 24 13U C28 C28 C 0 1 Y N N 11.955 -10.499 22.978 6.963 -0.978 -0.127 C24 00S 25 13U C21 C21 C 0 1 N N N 10.916 -10.403 24.065 8.323 -1.299 -0.619 C27 00S 26 13U N46 N46 N 0 1 N N N 10.143 -11.442 24.330 9.325 -0.527 -0.311 N35 00S 27 13U N47 N47 N 0 1 N N N 10.771 -9.280 24.759 8.527 -2.414 -1.401 N34 00S 28 13U C27 C27 C 0 1 Y N N 12.557 -11.700 22.646 6.753 0.150 0.665 C19 00S 29 13U C26 C26 C 0 1 Y N N 13.506 -11.763 21.647 5.484 0.443 1.120 C18 00S 30 13U H5 H5 H 0 1 N N N 18.678 -15.950 21.714 -3.612 1.256 0.493 H5 CNG 31 13U H5A H5A H 0 1 N N N 20.005 -14.936 22.617 -3.507 0.899 -1.247 H5A CNG 32 13U HN21 HN21 H 0 0 N N N 17.737 -15.710 23.933 -3.130 -1.423 -0.638 HN21 CNG 33 13U H49 H49 H 0 1 N N N 18.925 -16.412 25.845 -5.506 -0.018 0.332 H49 CNG 34 13U H48 H48 H 0 1 N N N 18.635 -13.797 24.909 -5.879 -2.898 0.134 H48 CNG 35 13U H48A H48A H 0 0 N N N 18.247 -14.780 26.490 -4.618 -2.516 1.330 H48A CNG 36 13U H47 H47 H 0 1 N N N 19.349 -13.056 27.171 -6.662 -2.441 2.556 H47 CNG 37 13U H47A H47A H 0 0 N N N 20.657 -14.510 26.747 -6.264 -0.737 2.235 H47A CNG 38 13U H46 H46 H 0 1 N N N 20.576 -11.747 25.843 -8.036 -2.351 0.366 H46 CNG 39 13U H46A H46A H 0 0 N N N 21.740 -12.643 27.014 -8.698 -1.480 1.771 H46A CNG 40 13U H45 H45 H 0 1 N N N 21.447 -12.984 24.046 -8.736 0.391 0.504 H45 CNG 41 13U H45A H45A H 0 0 N N N 22.852 -12.304 25.013 -6.957 0.351 0.489 H45A CNG 42 13U H44 H44 H 0 1 N N N 23.636 -14.324 24.613 -8.889 -0.819 -1.544 H44 CNG 43 13U H44A H44A H 0 0 N N N 22.559 -14.629 26.159 -7.584 0.362 -1.811 H44A CNG 44 13U H43 H43 H 0 1 N N N 21.776 -15.337 23.424 -7.024 -2.444 -0.787 H43 CNG 45 13U H43A H43A H 0 0 N N N 22.762 -16.410 24.693 -7.120 -2.081 -2.527 H43A CNG 46 13U H42 H42 H 0 1 N N N 20.985 -16.585 25.986 -5.425 -0.186 -2.044 H42 CNG 47 13U H42A H42A H 0 0 N N N 20.596 -17.022 24.107 -4.808 -1.855 -1.985 H42A CNG 48 13U H1 H1 H 0 1 N N N 18.293 -11.244 21.759 0.774 1.913 -1.449 HA PRO 49 13U H2 H2 H 0 1 N N N 18.888 -11.354 18.841 0.549 3.744 1.002 HB2 PRO 50 13U H2A H2A H 0 1 N N N 19.799 -10.442 20.113 1.513 3.991 -0.493 HB3 PRO 51 13U H3 H3 H 0 1 N N N 20.711 -12.695 18.656 -0.932 5.169 -0.259 HG2 PRO 52 13U H3A H3A H 0 1 N N N 21.496 -11.965 20.039 -0.446 4.433 -1.821 HG3 PRO 53 13U H4 H4 H 0 1 N N N 19.876 -14.439 19.910 -2.363 3.406 0.264 HD2 PRO 54 13U H4A H4A H 0 1 N N N 20.907 -13.882 21.236 -2.354 3.124 -1.499 HD3 PRO 55 13U HN23 HN23 H 0 0 N N N 16.629 -9.905 20.714 2.812 1.072 -0.495 HN23 00S 56 13U H24 H24 H 0 1 N N N 14.800 -9.792 19.249 3.109 0.466 2.248 H16 00S 57 13U H24A H24A H 0 0 N N N 14.735 -11.631 19.316 2.471 -0.975 1.421 H16A 00S 58 13U H30 H30 H 0 1 N N N 13.566 -8.528 20.740 3.791 -2.143 -0.239 H22 00S 59 13U H29 H29 H 0 1 N N N 11.888 -8.423 22.511 6.044 -2.678 -1.069 H21 00S 60 13U HN46 HN46 H 0 0 N N N 9.522 -11.194 25.073 10.216 -0.737 -0.633 HN35 00S 61 13U HN47 HN47 H 0 0 N N N 11.434 -8.611 24.422 7.780 -2.989 -1.631 HN34 00S 62 13U HN4A HN4A H 0 0 N N N 10.110 -9.129 25.494 9.418 -2.624 -1.723 HN3A 00S 63 13U H27 H27 H 0 1 N N N 12.280 -12.599 23.176 7.582 0.793 0.922 H19 00S 64 13U H26 H26 H 0 1 N N N 13.959 -12.714 21.409 5.320 1.316 1.734 H18 00S 65 # # 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 13U O22 C7 DOUB N N 1 13U C7 N23 SING N N 2 13U C7 C1 SING N N 3 13U N23 C24 SING N N 4 13U C24 C25 SING N N 5 13U C25 C26 DOUB Y N 6 13U C25 C30 SING Y N 7 13U C26 C27 SING Y N 8 13U C27 C28 DOUB Y N 9 13U C28 C21 SING N N 10 13U C28 C29 SING Y N 11 13U C21 N46 DOUB N N 12 13U C21 N47 SING N N 13 13U C29 C30 DOUB Y N 14 13U C1 C2 SING N N 15 13U C1 N1 SING N N 16 13U C2 C3 SING N N 17 13U C3 C4 SING N N 18 13U C4 N1 SING N N 19 13U N1 C14 SING N N 20 13U C14 O32 DOUB N N 21 13U C14 C5 SING N N 22 13U C5 N21 SING N N 23 13U N21 C49 SING N N 24 13U C49 C48 SING N N 25 13U C49 C42 SING N N 26 13U C48 C47 SING N N 27 13U C47 C46 SING N N 28 13U C46 C45 SING N N 29 13U C45 C44 SING N N 30 13U C44 C43 SING N N 31 13U C43 C42 SING N N 32 13U N23 HN23 SING N N 33 13U C24 H24 SING N N 34 13U C24 H24A SING N N 35 13U C26 H26 SING N N 36 13U C27 H27 SING N N 37 13U N46 HN46 SING N N 38 13U N47 HN47 SING N N 39 13U N47 HN4A SING N N 40 13U C29 H29 SING N N 41 13U C30 H30 SING N N 42 13U C1 H1 SING N N 43 13U C2 H2 SING N N 44 13U C2 H2A SING N N 45 13U C3 H3 SING N N 46 13U C3 H3A SING N N 47 13U C4 H4 SING N N 48 13U C4 H4A SING N N 49 13U C5 H5 SING N N 50 13U C5 H5A SING N N 51 13U N21 HN21 SING N N 52 13U C49 H49 SING N N 53 13U C48 H48 SING N N 54 13U C48 H48A SING N N 55 13U C47 H47 SING N N 56 13U C47 H47A SING N N 57 13U C46 H46 SING N N 58 13U C46 H46A SING N N 59 13U C45 H45 SING N N 60 13U C45 H45A SING N N 61 13U C44 H44 SING N N 62 13U C44 H44A SING N N 63 13U C43 H43 SING N N 64 13U C43 H43A SING N N 65 13U C42 H42 SING N N 66 13U C42 H42A SING N N 67 # # 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 13U SMILES ACDLabs 10.04 "O=C(NCc1ccc(C(=[N@H])N)cc1)C3N(C(=O)CNC2CCCCCCC2)CCC3" 13U InChI InChI 1.03 "InChI=1S/C23H35N5O2/c24-22(25)18-12-10-17(11-13-18)15-27-23(30)20-9-6-14-28(20)21(29)16-26-19-7-4-2-1-3-5-8-19/h10-13,19-20,26H,1-9,14-16H2,(H3,24,25)(H,27,30)/t20-/m0/s1" 13U InChIKey InChI 1.03 MMLOIDMSBRJZAE-FQEVSTJZSA-N 13U SMILES_CANONICAL CACTVS 3.385 "NC(=N)c1ccc(CNC(=O)[C@@H]2CCCN2C(=O)CNC3CCCCCCC3)cc1" 13U SMILES CACTVS 3.385 "NC(=N)c1ccc(CNC(=O)[CH]2CCCN2C(=O)CNC3CCCCCCC3)cc1" 13U SMILES_CANONICAL "OpenEye OEToolkits" 1.7.5 "[H]/N=C(/c1ccc(cc1)CNC(=O)[C@@H]2CCCN2C(=O)CNC3CCCCCCC3)\N" 13U SMILES "OpenEye OEToolkits" 1.7.5 "c1cc(ccc1CNC(=O)C2CCCN2C(=O)CNC3CCCCCCC3)C(=N)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 13U "SYSTEMATIC NAME" ACDLabs 10.04 "N-cyclooctylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide" 13U "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-N-[(4-carbamimidoylphenyl)methyl]-1-[2-(cyclooctylamino)ethanoyl]pyrrolidine-2-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 13U "Create component" 2008-02-06 PDBJ 13U "Modify subcomponent list" 2010-11-15 RCSB 13U "Modify aromatic_flag" 2011-06-04 RCSB 13U "Modify descriptor" 2011-06-04 RCSB 13U "Modify descriptor" 2012-01-05 RCSB 13U "Modify synonyms" 2021-03-01 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 13U _pdbx_chem_comp_synonyms.name "(2S)-N-[(4-carbamimidoylphenyl)methyl]-1-[2-(cyclooctylamino)ethanoyl]pyrrolidine-2-carboxamide" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##