data_RUP # _chem_comp.id RUP _chem_comp.name "(R)-2-(3-ADAMANTAN-1-YL-UREIDO)-3-(3-CARBAMIMIDOYL-PHENYL)-N-PHENETHYL-PROPIONAMIDE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C29 H37 N5 O2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2002-02-07 _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 487.636 _chem_comp.one_letter_code ? _chem_comp.three_letter_code RUP _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 1KYE _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 RUP C1 C1 C 0 1 N N N 19.256 33.507 16.998 -2.481 0.913 5.583 C1 RUP 1 RUP C6 C6 C 0 1 N N N 19.392 33.020 18.499 -2.207 1.487 4.191 C6 RUP 2 RUP C9 C9 C 0 1 N N N 20.187 31.644 18.559 -1.543 0.419 3.320 C9 RUP 3 RUP N10 N10 N 0 1 N N N 20.294 31.175 19.962 -1.281 0.968 1.988 N10 RUP 4 RUP C12 C12 C 0 1 N N N 20.935 30.016 20.311 -0.696 0.202 1.046 C12 RUP 5 RUP O17 O17 O 0 1 N N N 21.482 29.310 19.467 -0.386 -0.945 1.302 O17 RUP 6 RUP N13 N13 N 0 1 N N N 21.009 29.697 21.641 -0.455 0.707 -0.179 N13 RUP 7 RUP C14 C14 C 0 1 N N R 21.813 28.538 22.124 0.179 -0.125 -1.203 C14 RUP 8 RUP C26 C26 C 0 1 N N N 23.269 28.957 21.803 -0.295 0.305 -2.567 C26 RUP 9 RUP O31 O31 O 0 1 N N N 23.524 30.127 22.076 -1.087 1.217 -2.673 O31 RUP 10 RUP N27 N27 N 0 1 N N N 24.293 28.238 21.265 0.158 -0.324 -3.668 N27 RUP 11 RUP C28 C28 C 0 1 N N N 24.376 26.847 20.835 -0.303 0.094 -4.994 C28 RUP 12 RUP C29 C29 C 0 1 N N N 25.387 25.973 21.641 0.360 -0.776 -6.064 C29 RUP 13 RUP C30 C30 C 0 1 Y N N 25.645 26.460 23.088 -0.115 -0.345 -7.427 C30 RUP 14 RUP C36 C36 C 0 1 Y N N 26.431 27.604 23.443 0.573 0.629 -8.123 C36 RUP 15 RUP C35 C35 C 0 1 Y N N 26.592 27.992 24.805 0.137 1.024 -9.374 C35 RUP 16 RUP C34 C34 C 0 1 Y N N 25.967 27.240 25.836 -0.987 0.443 -9.929 C34 RUP 17 RUP C33 C33 C 0 1 Y N N 25.185 26.102 25.500 -1.675 -0.533 -9.234 C33 RUP 18 RUP C32 C32 C 0 1 Y N N 25.029 25.723 24.138 -1.236 -0.930 -7.985 C32 RUP 19 RUP C15 C15 C 0 1 N N N 21.679 28.386 23.676 1.699 0.033 -1.119 C15 RUP 20 RUP C16 C16 C 0 1 Y N N 20.277 28.000 24.234 2.174 -0.396 0.244 C16 RUP 21 RUP C22 C22 C 0 1 Y N N 19.440 26.976 23.674 2.531 -1.714 0.466 C22 RUP 22 RUP C21 C21 C 0 1 Y N N 18.165 26.696 24.256 2.969 -2.116 1.716 C21 RUP 23 RUP C20 C20 C 0 1 Y N N 17.714 27.426 25.395 3.052 -1.204 2.748 C20 RUP 24 RUP C19 C19 C 0 1 Y N N 18.542 28.444 25.960 2.693 0.125 2.529 C19 RUP 25 RUP C23 C23 C 0 1 N N N 18.103 29.243 27.177 2.780 1.109 3.633 C23 RUP 26 RUP N25 N25 N 0 1 N N N 18.983 30.000 27.782 3.216 0.711 4.878 N25 RUP 27 RUP N24 N24 N 0 1 N N N 16.873 29.162 27.616 2.444 2.350 3.426 N24 RUP 28 RUP C18 C18 C 0 1 Y N N 19.808 28.714 25.370 2.247 0.523 1.270 C18 RUP 29 RUP C8 C8 C 0 1 N N N 21.629 31.886 17.907 -2.472 -0.790 3.200 C8 RUP 30 RUP C11 C11 C 0 1 N N N 22.405 32.979 18.739 -0.223 -0.013 3.962 C11 RUP 31 RUP C4 C4 C 0 1 N N N 21.604 34.341 18.696 -0.497 -0.587 5.354 C4 RUP 32 RUP C5 C5 C 0 1 N N N 20.164 34.138 19.316 -1.161 0.481 6.225 C5 RUP 33 RUP C3 C3 C 0 1 N N N 21.463 34.818 17.201 -1.426 -1.797 5.233 C3 RUP 34 RUP C2 C2 C 0 1 N N N 20.683 33.726 16.374 -3.410 -0.296 5.462 C2 RUP 35 RUP C7 C7 C 0 1 N N N 21.485 32.375 16.409 -2.745 -1.364 4.591 C7 RUP 36 RUP H1 H1 H 0 1 N N N 18.499 33.463 16.181 -2.955 1.674 6.203 H1 RUP 37 RUP H61 1H6 H 0 1 N N N 18.402 32.952 19.006 -1.546 2.349 4.277 H61 RUP 38 RUP H62 2H6 H 0 1 N N N 19.856 33.798 19.149 -3.148 1.795 3.734 H62 RUP 39 RUP H10 H10 H 0 1 N N N 19.349 31.128 20.342 -1.528 1.884 1.784 H10 RUP 40 RUP H13 H13 H 0 1 N N N 20.477 30.310 22.259 -0.702 1.623 -0.383 H13 RUP 41 RUP H14 H14 H 0 1 N N N 21.494 27.576 21.658 -0.086 -1.169 -1.038 H14 RUP 42 RUP H27 H27 H 0 1 N N N 25.120 28.828 21.170 0.792 -1.054 -3.584 H27 RUP 43 RUP H281 1H28 H 0 0 N N N 24.602 26.792 19.744 -1.385 -0.019 -5.054 H281 RUP 44 RUP H282 2H28 H 0 0 N N N 23.365 26.378 20.847 -0.037 1.138 -5.159 H282 RUP 45 RUP H291 1H29 H 0 0 N N N 26.349 25.880 21.085 1.442 -0.662 -6.004 H291 RUP 46 RUP H292 2H29 H 0 0 N N N 25.063 24.906 21.642 0.094 -1.820 -5.899 H292 RUP 47 RUP H36 H36 H 0 1 N N N 26.921 28.197 22.653 1.452 1.084 -7.690 H36 RUP 48 RUP H35 H35 H 0 1 N N N 27.201 28.875 25.061 0.675 1.787 -9.918 H35 RUP 49 RUP H34 H34 H 0 1 N N N 26.088 27.538 26.891 -1.328 0.752 -10.906 H34 RUP 50 RUP H33 H33 H 0 1 N N N 24.699 25.513 26.296 -2.554 -0.986 -9.667 H33 RUP 51 RUP H32 H32 H 0 1 N N N 24.418 24.839 23.891 -1.774 -1.693 -7.441 H32 RUP 52 RUP H151 1H15 H 0 0 N N N 22.031 29.320 24.172 1.965 1.077 -1.284 H151 RUP 53 RUP H152 2H15 H 0 0 N N N 22.438 27.657 24.044 2.172 -0.586 -1.881 H152 RUP 54 RUP H22 H22 H 0 1 N N N 19.778 26.403 22.794 2.468 -2.431 -0.338 H22 RUP 55 RUP H21 H21 H 0 1 N N N 17.524 25.910 23.823 3.247 -3.147 1.883 H21 RUP 56 RUP H20 H20 H 0 1 N N N 16.728 27.204 25.837 3.395 -1.520 3.722 H20 RUP 57 RUP H251 1H25 H 0 0 N N N 19.396 30.637 27.100 3.273 1.355 5.601 H251 RUP 58 RUP H252 2H25 H 0 0 N N N 18.689 30.536 28.598 3.462 -0.214 5.033 H252 RUP 59 RUP H24 H24 H 0 1 N N N 16.339 29.961 27.274 2.137 2.630 2.550 H24 RUP 60 RUP H18 H18 H 0 1 N N N 20.446 29.501 25.807 1.968 1.552 1.095 H18 RUP 61 RUP H81 1H8 H 0 1 N N N 22.277 30.982 17.988 -3.412 -0.482 2.742 H81 RUP 62 RUP H82 2H8 H 0 1 N N N 22.246 32.588 18.515 -1.998 -1.551 2.579 H82 RUP 63 RUP H111 1H11 H 0 0 N N N 23.224 32.794 18.005 0.250 -0.774 3.342 H111 RUP 64 RUP H112 2H11 H 0 0 N N N 23.107 32.776 19.581 0.438 0.848 4.049 H112 RUP 65 RUP H4 H4 H 0 1 N N N 22.155 35.109 19.287 0.443 -0.895 5.811 H4 RUP 66 RUP H51 1H5 H 0 1 N N N 20.021 33.446 20.178 -0.500 1.343 6.311 H51 RUP 67 RUP H52 2H5 H 0 1 N N N 19.686 34.961 19.897 -1.356 0.072 7.216 H52 RUP 68 RUP H31 1H3 H 0 1 N N N 22.194 35.546 16.779 -0.952 -2.558 4.613 H31 RUP 69 RUP H32A 2H3 H 0 0 N N N 20.622 35.490 16.909 -1.621 -2.205 6.225 H32A RUP 70 RUP H21A 1H2 H 0 0 N N N 21.236 34.557 16.870 -3.605 -0.705 6.453 H21A RUP 71 RUP H22A 2H2 H 0 0 N N N 20.632 34.159 15.348 -4.350 0.011 5.004 H22A RUP 72 RUP H7 H7 H 0 1 N N N 21.725 31.533 15.718 -3.407 -2.226 4.505 H7 RUP 73 # 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 RUP C1 C6 SING N N 1 RUP C1 C5 SING N N 2 RUP C1 C2 SING N N 3 RUP C1 H1 SING N N 4 RUP C6 C9 SING N N 5 RUP C6 H61 SING N N 6 RUP C6 H62 SING N N 7 RUP C9 N10 SING N N 8 RUP C9 C8 SING N N 9 RUP C9 C11 SING N N 10 RUP N10 C12 SING N N 11 RUP N10 H10 SING N N 12 RUP C12 O17 DOUB N N 13 RUP C12 N13 SING N N 14 RUP N13 C14 SING N N 15 RUP N13 H13 SING N N 16 RUP C14 C26 SING N N 17 RUP C14 C15 SING N N 18 RUP C14 H14 SING N N 19 RUP C26 O31 DOUB N N 20 RUP C26 N27 SING N N 21 RUP N27 C28 SING N N 22 RUP N27 H27 SING N N 23 RUP C28 C29 SING N N 24 RUP C28 H281 SING N N 25 RUP C28 H282 SING N N 26 RUP C29 C30 SING N N 27 RUP C29 H291 SING N N 28 RUP C29 H292 SING N N 29 RUP C30 C36 DOUB Y N 30 RUP C30 C32 SING Y N 31 RUP C36 C35 SING Y N 32 RUP C36 H36 SING N N 33 RUP C35 C34 DOUB Y N 34 RUP C35 H35 SING N N 35 RUP C34 C33 SING Y N 36 RUP C34 H34 SING N N 37 RUP C33 C32 DOUB Y N 38 RUP C33 H33 SING N N 39 RUP C32 H32 SING N N 40 RUP C15 C16 SING N N 41 RUP C15 H151 SING N N 42 RUP C15 H152 SING N N 43 RUP C16 C22 DOUB Y N 44 RUP C16 C18 SING Y N 45 RUP C22 C21 SING Y N 46 RUP C22 H22 SING N N 47 RUP C21 C20 DOUB Y N 48 RUP C21 H21 SING N N 49 RUP C20 C19 SING Y N 50 RUP C20 H20 SING N N 51 RUP C19 C23 SING N N 52 RUP C19 C18 DOUB Y N 53 RUP C23 N25 SING N N 54 RUP C23 N24 DOUB N N 55 RUP N25 H251 SING N N 56 RUP N25 H252 SING N N 57 RUP N24 H24 SING N N 58 RUP C18 H18 SING N N 59 RUP C8 C7 SING N N 60 RUP C8 H81 SING N N 61 RUP C8 H82 SING N N 62 RUP C11 C4 SING N N 63 RUP C11 H111 SING N N 64 RUP C11 H112 SING N N 65 RUP C4 C5 SING N N 66 RUP C4 C3 SING N N 67 RUP C4 H4 SING N N 68 RUP C5 H51 SING N N 69 RUP C5 H52 SING N N 70 RUP C3 C7 SING N N 71 RUP C3 H31 SING N N 72 RUP C3 H32A SING N N 73 RUP C2 C7 SING N N 74 RUP C2 H21A SING N N 75 RUP C2 H22A SING N N 76 RUP C7 H7 SING N N 77 # 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 RUP SMILES ACDLabs 10.04 "O=C(NCCc1ccccc1)C(NC(=O)NC23CC4CC(C2)CC(C3)C4)Cc5cc(C(=[N@H])N)ccc5" RUP SMILES_CANONICAL CACTVS 3.341 "NC(=N)c1cccc(C[C@@H](NC(=O)NC23CC4CC(CC(C4)C2)C3)C(=O)NCCc5ccccc5)c1" RUP SMILES CACTVS 3.341 "NC(=N)c1cccc(C[CH](NC(=O)NC23CC4CC(CC(C4)C2)C3)C(=O)NCCc5ccccc5)c1" RUP SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1ccc(cc1)CCNC(=O)[C@@H](Cc2cccc(c2)C(=N)N)NC(=O)NC34CC5CC(C3)CC(C5)C4" RUP SMILES "OpenEye OEToolkits" 1.5.0 "c1ccc(cc1)CCNC(=O)C(Cc2cccc(c2)C(=N)N)NC(=O)NC34CC5CC(C3)CC(C5)C4" RUP InChI InChI 1.03 "InChI=1S/C29H37N5O2/c30-26(31)24-8-4-7-20(14-24)15-25(27(35)32-10-9-19-5-2-1-3-6-19)33-28(36)34-29-16-21-11-22(17-29)13-23(12-21)18-29/h1-8,14,21-23,25H,9-13,15-18H2,(H3,30,31)(H,32,35)(H2,33,34,36)/t21-,22+,23-,25-,29-/m1/s1" RUP InChIKey InChI 1.03 QYKLXCYULDLMPX-ZEFMGYOLSA-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 RUP "SYSTEMATIC NAME" ACDLabs 10.04 "3-carbamimidoyl-N-(2-phenylethyl)-Nalpha-[(3S,5S,7S)-tricyclo[3.3.1.1~3,7~]dec-1-ylcarbamoyl]-D-phenylalaninamide" RUP "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2R)-2-(1-adamantylcarbamoylamino)-3-(3-carbamimidoylphenyl)-N-phenethyl-propanamide" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site RUP "Create component" 2002-02-07 RCSB RUP "Modify descriptor" 2011-06-04 RCSB #