data_WRP # _chem_comp.id WRP _chem_comp.name "(betaR)-beta-hydroxy-1-[(3R)-3-hydroxy-2-methylbutan-2-yl]-L-tryptophan" _chem_comp.type "L-PEPTIDE LINKING" _chem_comp.pdbx_type ATOMP _chem_comp.formula "C16 H22 N2 O4" _chem_comp.mon_nstd_parent_comp_id TRP _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2013-06-20 _chem_comp.pdbx_modified_date 2023-11-03 _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 306.357 _chem_comp.one_letter_code W _chem_comp.three_letter_code WRP _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 3WDC _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.pdbx_backbone_atom_flag _chem_comp_atom.pdbx_n_terminal_atom_flag _chem_comp_atom.pdbx_c_terminal_atom_flag _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 WRP O O O 0 1 N N N Y N Y -27.230 12.376 -5.476 -4.592 -1.737 0.365 O WRP 1 WRP C C C 0 1 N N N Y N Y -26.109 12.242 -5.982 -4.266 -0.577 0.272 C WRP 2 WRP CA CA C 0 1 N N S Y N N -25.102 11.376 -5.249 -2.841 -0.170 0.549 CA WRP 3 WRP CB CB C 0 1 N N R N N N -25.709 9.961 -5.086 -2.094 0.005 -0.774 CB WRP 4 WRP CG CG C 0 1 Y N N N N N -25.839 9.272 -6.418 -0.641 0.291 -0.496 CG WRP 5 WRP CD1 CD1 C 0 1 Y N N N N N -26.945 9.206 -7.210 0.358 -0.606 -0.461 CD1 WRP 6 WRP NE1 NE1 N 0 1 Y N N N N N -26.664 8.459 -8.320 1.540 0.023 -0.179 NE1 WRP 7 WRP C1 C1 C 0 1 N N N N N N -27.660 8.132 -9.382 2.839 -0.643 -0.058 C1 WRP 8 WRP C3 C3 C 0 1 N N N N N N -28.953 8.903 -9.130 3.400 -0.415 1.347 C3 WRP 9 WRP C4 C4 C 0 1 N N R N N N -27.932 6.620 -9.343 2.668 -2.144 -0.301 C4 WRP 10 WRP C5 C5 C 0 1 N N N N N N -28.627 6.150 -8.065 4.025 -2.839 -0.175 C5 WRP 11 WRP O6 O6 O 0 1 N N N N N N -28.778 6.246 -10.421 1.764 -2.683 0.666 O6 WRP 12 WRP C2 C2 C 0 1 N N N N N N -27.152 8.547 -10.748 3.807 -0.066 -1.093 C2 WRP 13 WRP CE2 CE2 C 0 1 Y N N N N N -25.363 8.019 -8.282 1.326 1.374 -0.022 CE2 WRP 14 WRP CZ2 CZ2 C 0 1 Y N N N N N -24.605 7.227 -9.139 2.161 2.449 0.267 CZ2 WRP 15 WRP CH2 CH2 C 0 1 Y N N N N N -23.276 6.936 -8.789 1.634 3.718 0.361 CH2 WRP 16 WRP CZ3 CZ3 C 0 1 Y N N N N N -22.725 7.395 -7.601 0.276 3.937 0.172 CZ3 WRP 17 WRP CE3 CE3 C 0 1 Y N N N N N -23.445 8.213 -6.723 -0.562 2.896 -0.112 CE3 WRP 18 WRP CD2 CD2 C 0 1 Y N N N N N -24.782 8.514 -7.044 -0.048 1.602 -0.219 CD2 WRP 19 WRP OB OB O 0 1 N N N N N N -24.921 9.195 -4.196 -2.204 -1.193 -1.545 OB WRP 20 WRP N N N 0 1 N N N Y Y N -24.838 11.955 -3.947 -2.182 -1.210 1.350 N WRP 21 WRP OXT OXT O 0 1 N Y N Y N Y -25.855 12.864 -7.169 -5.170 0.348 -0.085 OXT WRP 22 WRP HA H2 H 0 1 N N N Y N N -24.175 11.307 -5.838 -2.833 0.771 1.098 H2 WRP 23 WRP H3 H3 H 0 1 N N N N N N -26.718 10.081 -4.665 -2.528 0.836 -1.330 H3 WRP 24 WRP H4 H4 H 0 1 N N N N N N -27.896 9.671 -6.995 0.244 -1.666 -0.630 H4 WRP 25 WRP H5 H5 H 0 1 N N N N N N -29.357 8.630 -8.144 4.367 -0.910 1.437 H5 WRP 26 WRP H6 H6 H 0 1 N N N N N N -28.747 9.983 -9.155 3.522 0.654 1.520 H6 WRP 27 WRP H7 H7 H 0 1 N N N N N N -29.687 8.652 -9.909 2.711 -0.826 2.085 H7 WRP 28 WRP H8 H8 H 0 1 N N N N N N -26.969 6.095 -9.426 2.268 -2.306 -1.302 H8 WRP 29 WRP H9 H9 H 0 1 N N N N N N -28.011 6.416 -7.193 4.424 -2.677 0.826 H9 WRP 30 WRP H10 H10 H 0 1 N N N N N N -29.610 6.637 -7.982 3.902 -3.908 -0.348 H10 WRP 31 WRP H11 H11 H 0 1 N N N N N N -28.761 5.059 -8.101 4.714 -2.428 -0.912 H11 WRP 32 WRP H12 H12 H 0 1 N N N N N N -28.940 5.310 -10.387 2.056 -2.574 1.581 H12 WRP 33 WRP H13 H13 H 0 1 N N N N N N -26.963 9.631 -10.756 3.407 -0.228 -2.094 H13 WRP 34 WRP H14 H14 H 0 1 N N N N N N -26.218 8.011 -10.970 3.929 1.003 -0.920 H14 WRP 35 WRP H15 H15 H 0 1 N N N N N N -27.906 8.301 -11.510 4.773 -0.561 -1.003 H15 WRP 36 WRP H16 H16 H 0 1 N N N N N N -25.030 6.844 -10.055 3.218 2.289 0.416 H16 WRP 37 WRP H17 H17 H 0 1 N N N N N N -22.671 6.343 -9.458 2.284 4.551 0.585 H17 WRP 38 WRP H18 H18 H 0 1 N N N N N N -21.714 7.113 -7.347 -0.121 4.938 0.250 H18 WRP 39 WRP H19 H19 H 0 1 N N N N N N -22.988 8.602 -5.825 -1.617 3.074 -0.257 H19 WRP 40 WRP H20 H20 H 0 1 N N N N N N -24.852 9.648 -3.364 -1.837 -1.975 -1.111 H20 WRP 41 WRP H H21 H 0 1 N N N Y Y N -24.174 11.389 -3.458 -2.177 -2.093 0.863 H21 WRP 42 WRP H2 H22 H 0 1 N Y N Y Y N -24.469 12.877 -4.061 -1.246 -0.932 1.605 H22 WRP 43 WRP HXT H1 H 0 1 N Y N Y N Y -26.628 13.339 -7.450 -6.070 0.039 -0.257 H1 WRP 44 # 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 WRP C2 C1 SING N N 1 WRP O6 C4 SING N N 2 WRP C1 C4 SING N N 3 WRP C1 C3 SING N N 4 WRP C1 NE1 SING N N 5 WRP C4 C5 SING N N 6 WRP CZ2 CH2 DOUB Y N 7 WRP CZ2 CE2 SING Y N 8 WRP CH2 CZ3 SING Y N 9 WRP NE1 CE2 SING Y N 10 WRP NE1 CD1 SING Y N 11 WRP CE2 CD2 DOUB Y N 12 WRP CZ3 CE3 DOUB Y N 13 WRP CD1 CG DOUB Y N 14 WRP OXT C SING N N 15 WRP CD2 CE3 SING Y N 16 WRP CD2 CG SING Y N 17 WRP CG CB SING N N 18 WRP C O DOUB N N 19 WRP C CA SING N N 20 WRP CA CB SING N N 21 WRP CA N SING N N 22 WRP CB OB SING N N 23 WRP CA HA SING N N 24 WRP CB H3 SING N N 25 WRP CD1 H4 SING N N 26 WRP C3 H5 SING N N 27 WRP C3 H6 SING N N 28 WRP C3 H7 SING N N 29 WRP C4 H8 SING N N 30 WRP C5 H9 SING N N 31 WRP C5 H10 SING N N 32 WRP C5 H11 SING N N 33 WRP O6 H12 SING N N 34 WRP C2 H13 SING N N 35 WRP C2 H14 SING N N 36 WRP C2 H15 SING N N 37 WRP CZ2 H16 SING N N 38 WRP CH2 H17 SING N N 39 WRP CZ3 H18 SING N N 40 WRP CE3 H19 SING N N 41 WRP OB H20 SING N N 42 WRP N H SING N N 43 WRP N H2 SING N N 44 WRP OXT HXT SING N N 45 # 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 WRP SMILES ACDLabs 12.01 "O=C(O)C(N)C(O)c2c1ccccc1n(c2)C(C)(C)C(O)C" WRP InChI InChI 1.03 "InChI=1S/C16H22N2O4/c1-9(19)16(2,3)18-8-11(14(20)13(17)15(21)22)10-6-4-5-7-12(10)18/h4-9,13-14,19-20H,17H2,1-3H3,(H,21,22)/t9-,13+,14-/m1/s1" WRP InChIKey InChI 1.03 KBGRLEDLMUJSBM-BIGNPOOSSA-N WRP SMILES_CANONICAL CACTVS 3.385 "C[C@@H](O)C(C)(C)n1cc([C@@H](O)[C@H](N)C(O)=O)c2ccccc12" WRP SMILES CACTVS 3.385 "C[CH](O)C(C)(C)n1cc([CH](O)[CH](N)C(O)=O)c2ccccc12" WRP SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "C[C@H](C(C)(C)n1cc(c2c1cccc2)[C@H]([C@@H](C(=O)O)N)O)O" WRP SMILES "OpenEye OEToolkits" 1.7.6 "CC(C(C)(C)n1cc(c2c1cccc2)C(C(C(=O)O)N)O)O" # 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 WRP "SYSTEMATIC NAME" ACDLabs 12.01 "(betaR)-beta-hydroxy-1-[(3R)-3-hydroxy-2-methylbutan-2-yl]-L-tryptophan" WRP "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "(2S,3R)-2-azanyl-3-[1-[(3R)-2-methyl-3-oxidanyl-butan-2-yl]indol-3-yl]-3-oxidanyl-propanoic 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 WRP "Create component" 2013-06-20 PDBJ WRP "Initial release" 2013-09-18 RCSB WRP "Modify backbone" 2023-11-03 PDBE #