data_359 # _chem_comp.id 359 _chem_comp.name "3-[[3-[(2R)-3-[[(2S)-5-amino-1-[(4-carbamimidoylphenyl)methylamino]-1,5-dioxo-pentan-2-yl]amino]-2-(ethylsulfonylamino)-3-oxo-propyl]-1H-indol-5-yl]oxymethyl]benzoic acid" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C34 H39 N7 O8 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2009-02-27 _chem_comp.pdbx_modified_date 2011-06-04 _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 705.781 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 359 _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 2ZZU _chem_comp.pdbx_subcomponent_list ? _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 359 C14 C14 C 0 1 N N N 35.607 6.967 10.274 0.601 -2.724 0.228 C14 359 1 359 O1 O1 O 0 1 N N N 34.673 7.232 11.026 1.343 -3.658 0.447 O1 359 2 359 N5 N5 N 0 1 N N N 35.666 7.377 8.970 1.112 -1.509 -0.053 N5 359 3 359 C15 C15 C 0 1 N N S 34.545 8.163 8.464 2.564 -1.316 -0.092 C15 359 4 359 C18 C18 C 0 1 N N N 34.634 8.500 6.982 3.091 -1.695 -1.478 C18 359 5 359 C19 C19 C 0 1 N N N 35.958 9.263 6.604 2.875 -3.191 -1.713 C19 359 6 359 C20 C20 C 0 1 N N N 33.269 7.427 8.764 2.886 0.129 0.190 C20 359 7 359 O5 O5 O 0 1 N N N 33.188 6.217 8.590 1.992 0.919 0.403 O5 359 8 359 N6 N6 N 0 1 N N N 32.300 8.248 9.237 4.169 0.542 0.205 N6 359 9 359 C21 C21 C 0 1 N N N 31.023 7.664 9.517 4.483 1.947 0.479 C21 359 10 359 C16 C16 C 0 1 Y N N 31.611 6.455 11.661 6.594 2.479 -0.753 C16 359 11 359 C17 C17 C 0 1 Y N N 31.350 6.197 13.011 7.961 2.662 -0.797 C17 359 12 359 C22 C22 C 0 1 Y N N 30.287 6.833 13.685 8.720 2.510 0.363 C22 359 13 359 C23 C23 C 0 1 Y N N 29.451 7.694 12.969 8.091 2.173 1.562 C23 359 14 359 C24 C24 C 0 1 Y N N 29.696 7.947 11.617 6.723 1.992 1.593 C24 359 15 359 C25 C25 C 0 1 Y N N 30.779 7.341 10.960 5.976 2.145 0.438 C25 359 16 359 C26 C26 C 0 1 N N N 30.080 6.626 15.123 10.187 2.705 0.323 C26 359 17 359 N1 N1 N 0 1 N N N 30.735 5.669 15.756 10.772 3.019 -0.797 N1 359 18 359 C2 C2 C 0 1 N N N 35.930 9.720 5.165 3.394 -3.565 -3.078 C2 359 19 359 O2 O2 O 0 1 N N N 35.730 8.930 4.270 3.888 -2.718 -3.792 O2 359 20 359 N3 N3 N 0 1 N N N 36.060 11.033 4.954 3.309 -4.840 -3.505 N3 359 21 359 C1 C1 C 0 1 N N N 37.750 6.951 11.639 -1.421 -3.067 -1.166 C1 359 22 359 N4 N4 N 0 1 N N N 36.324 5.042 11.656 -1.205 -4.137 1.023 N4 359 23 359 C5 C5 C 0 1 N N R 36.804 6.110 10.799 -0.892 -2.924 0.263 C5 359 24 359 S1 S1 S 0 1 N N N 36.208 3.464 11.008 -1.579 -4.031 2.632 S1 359 25 359 O4 O4 O 0 1 N N N 35.729 3.698 9.687 -1.793 -5.378 3.031 O4 359 26 359 O3 O3 O 0 1 N N N 35.422 2.787 11.980 -0.522 -3.262 3.188 O3 359 27 359 C9 C9 C 0 1 N N N 37.836 2.816 10.948 -3.135 -3.100 2.675 C9 359 28 359 C8 C8 C 0 1 N N N 38.257 2.373 12.358 -3.590 -2.934 4.127 C8 359 29 359 N2 N2 N 0 1 N N N 29.246 7.382 15.828 10.934 2.553 1.471 N2 359 30 359 C13 C13 C 0 1 Y N N 42.742 5.382 10.327 -6.084 -0.363 -1.066 C13 359 31 359 C12 C12 C 0 1 Y N N 42.347 4.962 11.655 -6.255 -1.730 -1.071 C12 359 32 359 C3 C3 C 0 1 Y N N 41.074 5.221 12.174 -5.146 -2.569 -1.096 C3 359 33 359 C4 C4 C 0 1 Y N N 40.114 5.892 11.349 -3.855 -2.012 -1.116 C4 359 34 359 C27 C27 C 0 1 Y N N 40.470 6.284 10.063 -3.694 -0.625 -1.111 C27 359 35 359 C6 C6 C 0 1 Y N N 41.783 6.079 9.519 -4.806 0.191 -1.086 C6 359 36 359 N7 N7 N 0 1 Y N N 40.484 5.115 13.422 -4.997 -3.940 -1.107 N7 359 37 359 C29 C29 C 0 1 Y N N 39.226 5.691 13.400 -3.668 -4.263 -1.133 C29 359 38 359 C28 C28 C 0 1 Y N N 38.954 6.181 12.119 -2.926 -3.144 -1.139 C28 359 39 359 O6 O6 O 0 1 N N N 41.996 6.708 8.281 -4.655 1.543 -1.081 O6 359 40 359 C7 C7 C 0 1 N N N 43.218 7.438 8.082 -5.848 2.329 -1.055 C7 359 41 359 C11 C11 C 0 1 Y N N 44.160 11.098 10.242 -4.819 6.485 -1.069 C11 359 42 359 C10 C10 C 0 1 Y N N 45.012 9.993 10.314 -5.008 5.812 -2.257 C10 359 43 359 C31 C31 C 0 1 Y N N 44.674 8.809 9.635 -5.341 4.469 -2.250 C31 359 44 359 C32 C32 C 0 1 Y N N 43.505 8.707 8.860 -5.485 3.792 -1.053 C32 359 45 359 C30 C30 C 0 1 Y N N 42.679 9.837 8.775 -5.299 4.453 0.144 C30 359 46 359 C33 C33 C 0 1 Y N N 42.987 11.020 9.476 -4.963 5.808 0.144 C33 359 47 359 C34 C34 C 0 1 N N N 42.041 12.124 9.458 -4.761 6.523 1.421 C34 359 48 359 O8 O8 O 0 1 N N N 42.461 13.292 9.601 -4.438 7.830 1.418 O8 359 49 359 O7 O7 O 0 1 N N N 40.830 11.847 9.326 -4.888 5.931 2.475 O7 359 50 359 HN5 HN5 H 0 1 N N N 36.446 7.147 8.387 0.518 -0.762 -0.228 HN5 359 51 359 H15 H15 H 0 1 N N N 34.572 9.135 8.979 3.035 -1.947 0.661 H15 359 52 359 H18 H18 H 0 1 N N N 34.601 7.560 6.411 2.556 -1.127 -2.238 H18 359 53 359 H18A H18A H 0 0 N N N 33.790 9.163 6.742 4.155 -1.468 -1.536 H18A 359 54 359 H19 H19 H 0 1 N N N 36.061 10.143 7.256 3.410 -3.760 -0.953 H19 359 55 359 H19A H19A H 0 0 N N N 36.808 8.577 6.737 1.811 -3.418 -1.655 H19A 359 56 359 HN6 HN6 H 0 1 N N N 32.470 9.222 9.385 4.885 -0.090 0.035 HN6 359 57 359 H21 H21 H 0 1 N N N 30.251 8.380 9.200 4.011 2.578 -0.274 H21 359 58 359 H21A H21A H 0 0 N N N 30.992 6.708 8.974 4.107 2.217 1.466 H21A 359 59 359 H16 H16 H 0 1 N N N 32.443 5.978 11.164 6.005 2.602 -1.650 H16 359 60 359 H17 H17 H 0 1 N N N 31.974 5.498 13.547 8.443 2.923 -1.728 H17 359 61 359 H23 H23 H 0 1 N N N 28.613 8.165 13.462 8.673 2.053 2.464 H23 359 62 359 H24 H24 H 0 1 N N N 29.046 8.615 11.072 6.235 1.731 2.520 H24 359 63 359 HN1 HN1 H 0 1 N N N 30.470 5.676 16.720 11.733 3.146 -0.823 HN1 359 64 359 HN3 HN3 H 0 1 N N N 36.185 11.512 5.823 2.914 -5.518 -2.935 HN3 359 65 359 HN3A HN3A H 0 0 N N N 36.036 11.473 4.057 3.644 -5.081 -4.384 HN3A 359 66 359 H1 H1 H 0 1 N N N 38.101 7.794 11.025 -1.111 -2.205 -1.756 H1 359 67 359 H1A H1A H 0 1 N N N 37.195 7.285 12.528 -1.018 -3.976 -1.613 H1A 359 68 359 HN4 HN4 H 0 1 N N N 36.959 4.988 12.426 -1.193 -5.002 0.583 HN4 359 69 359 H5 H5 H 0 1 N N N 37.323 5.710 9.915 -1.363 -2.065 0.740 H5 359 70 359 H9 H9 H 0 1 N N N 37.864 1.952 10.267 -2.983 -2.118 2.228 H9 359 71 359 H9A H9A H 0 1 N N N 38.528 3.589 10.582 -3.898 -3.640 2.115 H9A 359 72 359 H8 H8 H 0 1 N N N 38.358 1.278 12.384 -4.525 -2.374 4.153 H8 359 73 359 H8A H8A H 0 1 N N N 39.221 2.836 12.615 -3.742 -3.916 4.574 H8A 359 74 359 H8B H8B H 0 1 N N N 37.493 2.688 13.084 -2.827 -2.394 4.687 H8B 359 75 359 HN2 HN2 H 0 1 N N N 28.828 8.058 15.221 10.498 2.319 2.306 HN2 359 76 359 HN2A HN2A H 0 0 N N N 29.066 7.290 16.807 11.895 2.681 1.445 HN2A 359 77 359 H13 H13 H 0 1 N N N 43.734 5.176 9.954 -6.948 0.284 -1.051 H13 359 78 359 H12 H12 H 0 1 N N N 43.060 4.430 12.267 -7.250 -2.149 -1.055 H12 359 79 359 H27 H27 H 0 1 N N N 39.725 6.764 9.446 -2.704 -0.193 -1.126 H27 359 80 359 HN7 HN7 H 0 1 N N N 40.905 4.686 14.221 -5.726 -4.580 -1.097 HN7 359 81 359 H29 H29 H 0 1 N N N 38.556 5.753 14.245 -3.274 -5.268 -1.146 H29 359 82 359 H7 H7 H 0 1 N N N 44.029 6.740 8.338 -6.450 2.105 -1.935 H7 359 83 359 H7A H7A H 0 1 N N N 43.129 7.796 7.046 -6.418 2.095 -0.156 H7A 359 84 359 H11 H11 H 0 1 N N N 44.403 12.007 10.773 -4.556 7.533 -1.076 H11 359 85 359 H10 H10 H 0 1 N N N 45.925 10.048 10.888 -4.897 6.335 -3.196 H10 359 86 359 H31 H31 H 0 1 N N N 45.330 7.955 9.711 -5.489 3.947 -3.184 H31 359 87 359 H30 H30 H 0 1 N N N 41.791 9.800 8.161 -5.412 3.924 1.078 H30 359 88 359 HO8 HO8 H 0 1 N N N 41.728 13.896 9.591 -4.316 8.255 2.278 HO8 359 89 # 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 359 C14 O1 DOUB N N 1 359 C14 N5 SING N N 2 359 C14 C5 SING N N 3 359 N5 C15 SING N N 4 359 C15 C18 SING N N 5 359 C15 C20 SING N N 6 359 C18 C19 SING N N 7 359 C19 C2 SING N N 8 359 C20 O5 DOUB N N 9 359 C20 N6 SING N N 10 359 N6 C21 SING N N 11 359 C21 C25 SING N N 12 359 C16 C17 DOUB Y N 13 359 C16 C25 SING Y N 14 359 C17 C22 SING Y N 15 359 C22 C23 DOUB Y N 16 359 C22 C26 SING N N 17 359 C23 C24 SING Y N 18 359 C24 C25 DOUB Y N 19 359 C26 N1 DOUB N N 20 359 C26 N2 SING N N 21 359 C2 O2 DOUB N N 22 359 C2 N3 SING N N 23 359 C1 C5 SING N N 24 359 C1 C28 SING N N 25 359 N4 C5 SING N N 26 359 N4 S1 SING N N 27 359 S1 O4 DOUB N N 28 359 S1 O3 DOUB N N 29 359 S1 C9 SING N N 30 359 C9 C8 SING N N 31 359 C13 C12 DOUB Y N 32 359 C13 C6 SING Y N 33 359 C12 C3 SING Y N 34 359 C3 C4 DOUB Y N 35 359 C3 N7 SING Y N 36 359 C4 C27 SING Y N 37 359 C4 C28 SING Y N 38 359 C27 C6 DOUB Y N 39 359 C6 O6 SING N N 40 359 N7 C29 SING Y N 41 359 C29 C28 DOUB Y N 42 359 O6 C7 SING N N 43 359 C7 C32 SING N N 44 359 C11 C10 DOUB Y N 45 359 C11 C33 SING Y N 46 359 C10 C31 SING Y N 47 359 C31 C32 DOUB Y N 48 359 C32 C30 SING Y N 49 359 C30 C33 DOUB Y N 50 359 C33 C34 SING N N 51 359 C34 O8 SING N N 52 359 C34 O7 DOUB N N 53 359 N5 HN5 SING N N 54 359 C15 H15 SING N N 55 359 C18 H18 SING N N 56 359 C18 H18A SING N N 57 359 C19 H19 SING N N 58 359 C19 H19A SING N N 59 359 N6 HN6 SING N N 60 359 C21 H21 SING N N 61 359 C21 H21A SING N N 62 359 C16 H16 SING N N 63 359 C17 H17 SING N N 64 359 C23 H23 SING N N 65 359 C24 H24 SING N N 66 359 N1 HN1 SING N N 67 359 N3 HN3 SING N N 68 359 N3 HN3A SING N N 69 359 C1 H1 SING N N 70 359 C1 H1A SING N N 71 359 N4 HN4 SING N N 72 359 C5 H5 SING N N 73 359 C9 H9 SING N N 74 359 C9 H9A SING N N 75 359 C8 H8 SING N N 76 359 C8 H8A SING N N 77 359 C8 H8B SING N N 78 359 N2 HN2 SING N N 79 359 N2 HN2A SING N N 80 359 C13 H13 SING N N 81 359 C12 H12 SING N N 82 359 C27 H27 SING N N 83 359 N7 HN7 SING N N 84 359 C29 H29 SING N N 85 359 C7 H7 SING N N 86 359 C7 H7A SING N N 87 359 C11 H11 SING N N 88 359 C10 H10 SING N N 89 359 C31 H31 SING N N 90 359 C30 H30 SING N N 91 359 O8 HO8 SING N N 92 # 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 359 SMILES ACDLabs 10.04 "O=C(NCc1ccc(C(=[N@H])N)cc1)C(NC(=O)C(NS(=O)(=O)CC)Cc4c3cc(OCc2cc(C(=O)O)ccc2)ccc3nc4)CCC(=O)N" 359 SMILES_CANONICAL CACTVS 3.341 "CC[S](=O)(=O)N[C@H](Cc1c[nH]c2ccc(OCc3cccc(c3)C(O)=O)cc12)C(=O)N[C@@H](CCC(N)=O)C(=O)NCc4ccc(cc4)C(N)=N" 359 SMILES CACTVS 3.341 "CC[S](=O)(=O)N[CH](Cc1c[nH]c2ccc(OCc3cccc(c3)C(O)=O)cc12)C(=O)N[CH](CCC(N)=O)C(=O)NCc4ccc(cc4)C(N)=N" 359 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "[H]/N=C(/c1ccc(cc1)CNC(=O)[C@H](CCC(=O)N)NC(=O)[C@@H](Cc2c[nH]c3c2cc(cc3)OCc4cccc(c4)C(=O)O)NS(=O)(=O)CC)\N" 359 SMILES "OpenEye OEToolkits" 1.5.0 "[H]N=C(c1ccc(cc1)CNC(=O)C(CCC(=O)N)NC(=O)C(Cc2c[nH]c3c2cc(cc3)OCc4cccc(c4)C(=O)O)NS(=O)(=O)CC)N" 359 InChI InChI 1.03 ;InChI=1S/C34H39N7O8S/c1-2-50(47,48)41-29(33(44)40-28(12-13-30(35)42)32(43)39-17-20-6-8-22(9-7-20)31(36)37)15-24-18-38-27-11-10-25(16-26(24)27)49-19-21-4-3-5-23(14-21)34(45)46/h3-11,14,16,18,28-29,38,41H,2,12-13,15,17,19H2,1H3,(H2,35,42)(H3,36,37)(H,39,43)(H,40,44)(H,45,46)/t28-,29+/m0/s1 ; 359 InChIKey InChI 1.03 UDNWHSWDIIAZDA-URLMMPGGSA-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 359 "SYSTEMATIC NAME" ACDLabs 10.04 "5-[(3-carboxybenzyl)oxy]-N-(ethylsulfonyl)-D-tryptophyl-N~1~-(4-carbamimidoylbenzyl)-L-glutamamide" 359 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "3-[[3-[(2R)-3-[[(2S)-5-amino-1-[(4-carbamimidoylphenyl)methylamino]-1,5-dioxo-pentan-2-yl]amino]-2-(ethylsulfonylamino)-3-oxo-propyl]-1H-indol-5-yl]oxymethyl]benzoic acid" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 359 "Create component" 2009-02-27 PDBJ 359 "Modify aromatic_flag" 2011-06-04 RCSB 359 "Modify descriptor" 2011-06-04 RCSB #