data_3QN # _chem_comp.id 3QN _chem_comp.name "(E)-N~6~-{2-hydroxy-3-methyl-6-[(phosphonooxy)methyl]benzylidene}-L-lysine" _chem_comp.type "L-PEPTIDE LINKING" _chem_comp.pdbx_type ATOMP _chem_comp.formula "C15 H23 N2 O7 P" _chem_comp.mon_nstd_parent_comp_id LYS _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2011-02-09 _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 374.326 _chem_comp.one_letter_code K _chem_comp.three_letter_code 3QN _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 3QN6 _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.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 3QN C C1 C 0 1 N N N Y N Y -37.497 14.869 -4.501 -7.489 -1.208 0.784 C1 3QN 1 3QN N N1 N 0 1 N N N Y Y N -37.652 16.618 -6.221 -7.023 -0.453 -1.478 N1 3QN 2 3QN O O1 O 0 1 N N N Y N Y -36.927 13.793 -4.358 -8.455 -0.482 0.758 O1 3QN 3 3QN P1 P1 P 0 1 N N N N N N -37.733 22.350 -10.060 4.794 -2.536 0.064 P1 3QN 4 3QN C2 C2 C 0 1 Y N N N N N -36.800 26.348 -5.374 3.730 2.968 0.748 C2 3QN 5 3QN C3 C3 C 0 1 Y N N N N N -35.773 25.743 -4.674 2.526 3.599 0.499 C3 3QN 6 3QN C4 C4 C 0 1 Y N N N N N -35.349 24.474 -5.008 1.442 2.869 0.038 C4 3QN 7 3QN O2 O2 O 0 1 N N N N N N -34.317 23.850 -4.338 0.259 3.488 -0.207 O2 3QN 8 3QN C5 C5 C 0 1 Y N N N N N -35.976 23.828 -6.109 1.572 1.490 -0.175 C5 3QN 9 3QN C6 C6 C 0 1 Y N N N N N -37.024 24.445 -6.795 2.795 0.865 0.081 C6 3QN 10 3QN C7 C7 C 0 1 Y N N N N N -37.433 25.718 -6.435 3.865 1.607 0.534 C7 3QN 11 3QN CA C8 C 0 1 N N S Y N N -36.790 15.988 -5.251 -6.446 -1.112 -0.299 C8 3QN 12 3QN C9 C9 C 0 1 N N N N N N -36.317 17.068 -4.257 -5.256 -0.296 0.209 C9 3QN 13 3QN C10 C10 C 0 1 N N N N N N -35.804 19.351 -5.158 -2.955 0.513 -0.334 C10 3QN 14 3QN C11 C11 C 0 1 N N N N N N -34.709 20.231 -5.857 -1.845 0.505 -1.387 C11 3QN 15 3QN C12 C12 C 0 1 N N N N N N -35.296 17.958 -4.848 -4.145 -0.303 -0.843 C12 3QN 16 3QN N2 N2 N 0 1 N N N N N N -34.759 21.678 -5.547 -0.705 1.287 -0.900 N2 3QN 17 3QN O3 O3 O 0 1 N N N N N N -39.018 21.795 -9.609 4.779 -2.986 -1.482 O3 3QN 18 3QN C13 C13 C 0 1 N N N N N N -35.128 26.490 -3.480 2.392 5.082 0.730 C13 3QN 19 3QN O4 O4 O 0 1 N N N N N N -38.027 23.456 -11.064 3.904 -3.424 0.844 O4 3QN 20 3QN O5 O5 O 0 1 N N N N N N -36.787 21.300 -10.530 6.294 -2.641 0.638 O5 3QN 21 3QN C14 C14 C 0 1 N N N N N N -35.582 22.394 -6.503 0.426 0.704 -0.665 C14 3QN 22 3QN O6 O6 O 0 1 N N N N N N -37.020 22.917 -8.827 4.278 -1.016 0.185 O6 3QN 23 3QN C15 C15 C 0 1 N N N N N N -37.724 23.746 -7.944 2.946 -0.618 -0.145 C15 3QN 24 3QN OXT OXT O 0 1 N Y N Y N Y -38.846 15.076 -3.955 -7.343 -2.095 1.781 OXT 3QN 25 3QN H H1 H 0 1 N N N Y Y N -37.151 17.345 -6.690 -7.342 0.477 -1.253 H1 3QN 26 3QN H2 H2 H 0 1 N Y N Y Y N -37.955 15.938 -6.889 -6.364 -0.434 -2.241 H2 3QN 27 3QN H3 H3 H 0 1 N N N N N N -37.118 27.339 -5.087 4.572 3.541 1.107 H3 3QN 28 3QN H4 H4 H 0 1 N N N N N N -38.230 26.211 -6.971 4.810 1.123 0.731 H4 3QN 29 3QN HA H5 H 0 1 N N N Y N N -35.937 15.534 -5.776 -6.111 -2.113 -0.570 H5 3QN 30 3QN H6 H6 H 0 1 N N N N N N -37.184 17.677 -3.961 -5.573 0.730 0.396 H6 3QN 31 3QN H7 H7 H 0 1 N N N N N N -35.882 16.570 -3.378 -4.883 -0.735 1.135 H7 3QN 32 3QN H8 H8 H 0 1 N N N N N N -36.671 19.268 -5.830 -2.582 0.073 0.591 H8 3QN 33 3QN H9 H9 H 0 1 N N N N N N -33.727 19.857 -5.532 -1.528 -0.521 -1.574 H9 3QN 34 3QN H10 H10 H 0 1 N N N N N N -34.840 20.121 -6.944 -2.218 0.945 -2.312 H10 3QN 35 3QN H11 H11 H 0 1 N N N N N N -34.951 17.504 -5.789 -3.829 -1.329 -1.030 H11 3QN 36 3QN H12 H12 H 0 1 N N N N N N -34.467 18.049 -4.131 -4.519 0.136 -1.768 H12 3QN 37 3QN H13 H13 H 0 1 N N N N N N -39.730 22.250 -10.044 5.342 -2.447 -2.054 H13 3QN 38 3QN H14 H14 H 0 1 N N N N N N -35.676 26.249 -2.557 2.653 5.617 -0.183 H14 3QN 39 3QN H15 H15 H 0 1 N N N N N N -34.079 26.177 -3.376 1.364 5.315 1.007 H15 3QN 40 3QN H16 H16 H 0 1 N N N N N N -35.171 27.574 -3.660 3.062 5.387 1.534 H16 3QN 41 3QN H17 H17 H 0 1 N N N N N N -36.508 21.498 -11.416 6.670 -3.531 0.596 H17 3QN 42 3QN H18 H18 H 0 1 N N N N N N -35.899 21.948 -7.434 0.530 -0.359 -0.827 H18 3QN 43 3QN H19 H19 H 0 1 N N N N N N -38.152 24.547 -8.564 2.239 -1.155 0.487 H19 3QN 44 3QN H20 H20 H 0 1 N N N N N N -38.490 23.106 -7.482 2.747 -0.848 -1.191 H20 3QN 45 3QN HXT HXT H 0 1 N Y N Y N Y -39.137 14.283 -3.520 -8.036 -2.117 2.454 HXT 3QN 46 3QN H22 H22 H 0 1 N N N N N N -36.097 19.837 -4.216 -3.272 1.539 -0.147 H22 3QN 47 3QN H23 H23 H 0 1 N N N N N N -34.173 22.988 -4.710 0.168 3.819 -1.111 H23 3QN 48 # 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 3QN C O DOUB N N 1 3QN C OXT SING N N 2 3QN N CA SING N N 3 3QN N H SING N N 4 3QN N H2 SING N N 5 3QN P1 O3 SING N N 6 3QN P1 O6 SING N N 7 3QN C2 C3 SING Y N 8 3QN C2 H3 SING N N 9 3QN C3 C13 SING N N 10 3QN C4 C3 DOUB Y N 11 3QN C4 O2 SING N N 12 3QN C5 C4 SING Y N 13 3QN C6 C5 DOUB Y N 14 3QN C6 C7 SING Y N 15 3QN C7 C2 DOUB Y N 16 3QN C7 H4 SING N N 17 3QN CA C SING N N 18 3QN CA C9 SING N N 19 3QN CA HA SING N N 20 3QN C9 H6 SING N N 21 3QN C9 H7 SING N N 22 3QN C10 C12 SING N N 23 3QN C10 H8 SING N N 24 3QN C10 H22 SING N N 25 3QN C11 C10 SING N N 26 3QN C11 N2 SING N N 27 3QN C11 H9 SING N N 28 3QN C11 H10 SING N N 29 3QN C12 C9 SING N N 30 3QN C12 H11 SING N N 31 3QN C12 H12 SING N N 32 3QN O3 H13 SING N N 33 3QN C13 H14 SING N N 34 3QN C13 H15 SING N N 35 3QN C13 H16 SING N N 36 3QN O4 P1 DOUB N N 37 3QN O5 P1 SING N N 38 3QN O5 H17 SING N N 39 3QN C14 C5 SING N N 40 3QN C14 N2 DOUB N N 41 3QN C14 H18 SING N N 42 3QN O6 C15 SING N N 43 3QN C15 C6 SING N N 44 3QN C15 H19 SING N N 45 3QN C15 H20 SING N N 46 3QN OXT HXT SING N N 47 3QN O2 H23 SING N N 48 # 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 3QN SMILES ACDLabs 12.01 "O=C(O)C(N)CCCC/N=C/c1c(ccc(c1O)C)COP(=O)(O)O" 3QN SMILES_CANONICAL CACTVS 3.370 "Cc1ccc(CO[P](O)(O)=O)c(C=NCCCC[C@H](N)C(O)=O)c1O" 3QN SMILES CACTVS 3.370 "Cc1ccc(CO[P](O)(O)=O)c(C=NCCCC[CH](N)C(O)=O)c1O" 3QN SMILES_CANONICAL "OpenEye OEToolkits" 1.7.0 "Cc1ccc(c(c1O)/C=N/CCCC[C@@H](C(=O)O)N)COP(=O)(O)O" 3QN SMILES "OpenEye OEToolkits" 1.7.0 "Cc1ccc(c(c1O)C=NCCCCC(C(=O)O)N)COP(=O)(O)O" 3QN InChI InChI 1.03 "InChI=1S/C15H23N2O7P/c1-10-5-6-11(9-24-25(21,22)23)12(14(10)18)8-17-7-3-2-4-13(16)15(19)20/h5-6,8,13,18H,2-4,7,9,16H2,1H3,(H,19,20)(H2,21,22,23)/b17-8+/t13-/m0/s1" 3QN InChIKey InChI 1.03 PWEHKEQDPFXDSM-TVYFDWKESA-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 3QN "SYSTEMATIC NAME" ACDLabs 12.01 "(E)-N~6~-{2-hydroxy-3-methyl-6-[(phosphonooxy)methyl]benzylidene}-L-lysine" 3QN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.0 "(2S)-2-azanyl-6-[(E)-[2-hydroxy-3-methyl-6-(phosphonooxymethyl)phenyl]methylideneamino]hexanoic 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 3QN "Other modification" 2011-02-09 RCSB 3QN "Modify aromatic_flag" 2011-06-04 RCSB 3QN "Modify descriptor" 2011-06-04 RCSB 3QN "Modify backbone" 2023-11-03 PDBE #