data_QOH
# 
_chem_comp.id                                    QOH 
_chem_comp.name                                  "11-methyl-~{N}-[(2~{S},3~{R})-1-[[(5~{S},8~{S},10~{S})-5-methyl-10-oxidanyl-2,7-bis(oxidanylidene)-1,6-diazacyclododec-8-yl]amino]-3-oxidanyl-1-oxidanylidene-butan-2-yl]dodecanamide" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C28 H52 N4 O6" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "Syrbactin inhibitor; HB333" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2020-07-09 
_chem_comp.pdbx_modified_date                    2024-09-27 
_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                        540.736 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     QOH 
_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        6ZOU 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBE 
_chem_comp.pdbx_pcm                              Y 
# 
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 
QOH C4  C1  C 0 1 N N N N N N 55.583 -133.057 35.317 -6.519  -0.359 -0.117 C4  QOH 1  
QOH C5  C2  C 0 1 N N N N N N 54.203 -133.290 34.762 -7.685  0.328  0.596  C5  QOH 2  
QOH C6  C3  C 0 1 N N N N N N 53.927 -132.324 33.646 -9.001  -0.323 0.167  C6  QOH 3  
QOH C7  C4  C 0 1 N N N N N N 52.658 -131.603 33.957 -10.167 0.364  0.881  C7  QOH 4  
QOH C8  C5  C 0 1 N N N N N N 51.601 -132.050 32.987 -11.483 -0.287 0.451  C8  QOH 5  
QOH C10 C6  C 0 1 N N N N N N 49.148 -131.788 32.641 -13.965 -0.251 0.735  C10 QOH 6  
QOH C15 C7  C 0 1 N N N N N N 61.358 -134.372 37.266 2.065   -0.501 -0.319 C15 QOH 7  
QOH C17 C8  C 0 1 N N S N N N 61.262 -135.625 39.311 4.448   -0.864 0.037  C17 QOH 8  
QOH C21 C9  C 0 1 N N N N N N 59.125 -138.361 40.511 7.859   -2.277 0.189  C21 QOH 9  
QOH C22 C10 C 0 1 N N N N N N 59.500 -138.588 41.900 8.919   -1.665 1.107  C22 QOH 10 
QOH C24 C11 C 0 1 N N N N N N 61.461 -137.915 43.136 8.107   0.590  0.892  C24 QOH 11 
QOH C26 C12 C 0 1 N N N N N N 62.793 -137.716 43.131 8.262   2.034  0.490  C26 QOH 12 
QOH C28 C13 C 0 1 N N S N N N 63.396 -135.496 42.321 5.854   2.657  0.252  C28 QOH 13 
QOH C27 C14 C 0 1 N N N N N N 63.182 -136.345 43.537 7.119   2.856  1.089  C27 QOH 14 
QOH C29 C15 C 0 1 N N N N N N 63.727 -134.108 42.772 4.906   3.840  0.459  C29 QOH 15 
QOH N30 N1  N 0 1 N N N N N N 62.217 -135.491 41.473 5.194   1.400  0.698  N30 QOH 16 
QOH C31 C16 C 0 1 N N N N N N 62.343 -135.605 40.116 5.090   0.458  -0.298 C31 QOH 17 
QOH O32 O1  O 0 1 N N N N N N 63.443 -135.687 39.630 5.504   0.684  -1.415 O32 QOH 18 
QOH O25 O2  O 0 1 N N N N N N 60.785 -137.743 44.124 7.073   0.193  1.385  O25 QOH 19 
QOH N23 N2  N 0 1 N N N N N N 60.909 -138.365 41.986 9.155   -0.264 0.688  N23 QOH 20 
QOH C19 C17 C 0 1 N N S N N N 59.442 -136.998 40.141 6.475   -2.098 0.818  C19 QOH 21 
QOH O20 O3  O 0 1 N N N N N N 58.412 -136.563 39.336 6.184   -3.219 1.655  O20 QOH 22 
QOH C18 C18 C 0 1 N N N N N N 60.679 -136.991 39.340 5.422   -2.000 -0.287 C18 QOH 23 
QOH N16 N3  N 0 1 N N N N N N 61.756 -135.401 37.979 3.226   -1.028 -0.755 N16 QOH 24 
QOH O33 O4  O 0 1 N N N N N N 60.566 -133.554 37.663 2.032   0.108  0.729  O33 QOH 25 
QOH C14 C19 C 0 1 N N S N N N 61.937 -134.254 35.897 0.808   -0.669 -1.133 C14 QOH 26 
QOH C34 C20 C 0 1 N N R N N N 62.873 -133.111 35.850 1.005   -0.038 -2.512 C34 QOH 27 
QOH C36 C21 C 0 1 N N N N N N 64.138 -133.444 36.563 -0.309  -0.097 -3.293 C36 QOH 28 
QOH O35 O5  O 0 1 N N N N N N 63.195 -132.966 34.513 1.407   1.325  -2.359 O35 QOH 29 
QOH N13 N4  N 0 1 N N N N N N 60.876 -133.855 35.013 -0.308  -0.011 -0.449 N13 QOH 30 
QOH C12 C22 C 0 1 N N N N N N 59.865 -134.631 34.705 -1.572  -0.421 -0.675 C12 QOH 31 
QOH O37 O6  O 0 1 N N N N N N 59.713 -135.749 35.132 -1.786  -1.334 -1.444 O37 QOH 32 
QOH C1  C23 C 0 1 N N N N N N 58.842 -134.041 33.799 -2.721  0.256  0.028  C1  QOH 33 
QOH C2  C24 C 0 1 N N N N N N 57.558 -134.227 34.550 -4.037  -0.395 -0.401 C2  QOH 34 
QOH C3  C25 C 0 1 N N N N N N 56.601 -133.136 34.209 -5.203  0.292  0.312  C3  QOH 35 
QOH C9  C26 C 0 1 N N N N N N 50.377 -131.210 33.268 -12.649 0.400  1.165  C9  QOH 36 
QOH C11 C27 C 0 1 N N N N N N 49.403 -132.072 31.173 -15.118 0.350  1.541  C11 QOH 37 
QOH C40 C28 C 0 1 N N N N N N 48.057 -130.751 32.767 -14.197 0.002  -0.756 C40 QOH 38 
QOH H1  H1  H 0 1 N N N N N N 55.806 -133.824 36.073 -6.504  -1.417 0.147  H1  QOH 39 
QOH H2  H2  H 0 1 N N N N N N 55.626 -132.061 35.782 -6.641  -0.255 -1.195 H2  QOH 40 
QOH H3  H3  H 0 1 N N N N N N 53.460 -133.146 35.560 -7.563  0.224  1.675  H3  QOH 41 
QOH H4  H4  H 0 1 N N N N N N 54.134 -134.319 34.379 -7.699  1.385  0.333  H4  QOH 42 
QOH H5  H5  H 0 1 N N N N N N 53.822 -132.871 32.697 -9.123  -0.219 -0.911 H5  QOH 43 
QOH H6  H6  H 0 1 N N N N N N 54.754 -131.604 33.564 -8.986  -1.381 0.431  H6  QOH 44 
QOH H7  H7  H 0 1 N N N N N N 52.815 -130.519 33.860 -10.045 0.260  1.959  H7  QOH 45 
QOH H8  H8  H 0 1 N N N N N N 52.341 -131.837 34.984 -10.181 1.421  0.617  H8  QOH 46 
QOH H9  H9  H 0 1 N N N N N N 51.373 -133.116 33.138 -11.605 -0.183 -0.627 H9  QOH 47 
QOH H10 H10 H 0 1 N N N N N N 51.942 -131.891 31.953 -11.468 -1.345 0.715  H10 QOH 48 
QOH H11 H11 H 0 1 N N N N N N 48.853 -132.713 33.159 -13.915 -1.325 0.918  H11 QOH 49 
QOH H12 H12 H 0 1 N N N N N N 60.507 -134.875 39.590 4.200   -0.890 1.098  H12 QOH 50 
QOH H13 H13 H 0 1 N N N N N N 58.045 -138.532 40.390 7.885   -1.778 -0.780 H13 QOH 51 
QOH H14 H14 H 0 1 N N N N N N 59.681 -139.055 39.863 8.063   -3.339 0.056  H14 QOH 52 
QOH H15 H15 H 0 1 N N N N N N 58.964 -137.887 42.557 8.565   -1.684 2.138  H15 QOH 53 
QOH H16 H16 H 0 1 N N N N N N 59.261 -139.621 42.193 9.846   -2.232 1.025  H16 QOH 54 
QOH H17 H17 H 0 1 N N N N N N 63.255 -138.431 43.827 9.214   2.414  0.860  H17 QOH 55 
QOH H18 H18 H 0 1 N N N N N N 63.170 -137.899 42.114 8.236   2.114  -0.596 H18 QOH 56 
QOH H19 H19 H 0 1 N N N N N N 64.250 -135.897 41.756 6.119   2.579  -0.803 H19 QOH 57 
QOH H20 H20 H 0 1 N N N N N N 64.113 -136.388 44.121 6.932   2.528  2.112  H20 QOH 58 
QOH H21 H21 H 0 1 N N N N N N 62.383 -135.906 44.153 7.391   3.911  1.090  H21 QOH 59 
QOH H22 H22 H 0 1 N N N N N N 64.621 -134.133 43.412 5.401   4.761  0.152  H22 QOH 60 
QOH H23 H23 H 0 1 N N N N N N 63.922 -133.474 41.894 4.006   3.694  -0.140 H23 QOH 61 
QOH H24 H24 H 0 1 N N N N N N 62.881 -133.696 43.341 4.634   3.907  1.512  H24 QOH 62 
QOH H25 H25 H 0 1 N N N N N N 61.309 -135.404 41.883 4.869   1.260  1.601  H25 QOH 63 
QOH H26 H26 H 0 1 N N N N N N 61.490 -138.543 41.192 9.993   0.027  0.298  H26 QOH 64 
QOH H27 H27 H 0 1 N N N N N N 59.559 -136.367 41.035 6.462   -1.186 1.414  H27 QOH 65 
QOH H28 H28 H 0 1 N N N N N N 57.602 -136.559 39.832 6.813   -3.343 2.379  H28 QOH 66 
QOH H29 H29 H 0 1 N N N N N N 60.449 -137.310 38.313 4.874   -2.940 -0.352 H29 QOH 67 
QOH H30 H30 H 0 1 N N N N N N 61.405 -137.687 39.786 5.911   -1.798 -1.240 H30 QOH 68 
QOH H31 H31 H 0 1 N N N N N N 62.416 -136.042 37.587 3.253   -1.516 -1.593 H31 QOH 69 
QOH H32 H32 H 0 1 N N N N N N 62.419 -135.190 35.579 0.589   -1.731 -1.247 H32 QOH 70 
QOH H33 H33 H 0 1 N N N N N N 62.412 -132.206 36.273 1.776   -0.584 -3.055 H33 QOH 71 
QOH H34 H34 H 0 1 N N N N N N 63.932 -133.570 37.636 -1.080  0.449  -2.750 H34 QOH 72 
QOH H35 H35 H 0 1 N N N N N N 64.552 -134.379 36.157 -0.168  0.353  -4.276 H35 QOH 73 
QOH H36 H36 H 0 1 N N N N N N 64.864 -132.629 36.422 -0.615  -1.137 -3.410 H36 QOH 74 
QOH H37 H37 H 0 1 N N N N N N 63.800 -132.241 34.409 0.767   1.873  -1.883 H37 QOH 75 
QOH H38 H38 H 0 1 N N N N N N 60.911 -132.939 34.613 -0.138  0.719  0.166  H38 QOH 76 
QOH H39 H39 H 0 1 N N N N N N 58.815 -134.574 32.837 -2.599  0.152  1.106  H39 QOH 77 
QOH H40 H40 H 0 1 N N N N N N 59.043 -132.974 33.622 -2.735  1.313  -0.235 H40 QOH 78 
QOH H41 H41 H 0 1 N N N N N N 57.115 -135.197 34.279 -4.159  -0.291 -1.480 H41 QOH 79 
QOH H42 H42 H 0 1 N N N N N N 57.763 -134.207 35.631 -4.022  -1.453 -0.138 H42 QOH 80 
QOH H43 H43 H 0 1 N N N N N N 57.138 -132.180 34.124 -5.217  1.349  0.049  H43 QOH 81 
QOH H44 H44 H 0 1 N N N N N N 56.100 -133.361 33.256 -5.081  0.188  1.390  H44 QOH 82 
QOH H45 H45 H 0 1 N N N N N N 50.540 -130.199 32.866 -12.527 0.296  2.243  H45 QOH 83 
QOH H46 H46 H 0 1 N N N N N N 50.227 -131.152 34.356 -12.663 1.457  0.901  H46 QOH 84 
QOH H47 H47 H 0 1 N N N N N N 50.197 -132.827 31.078 -16.056 -0.113 1.235  H47 QOH 85 
QOH H48 H48 H 0 1 N N N N N N 48.481 -132.449 30.707 -14.953 0.170  2.603  H48 QOH 86 
QOH H49 H49 H 0 1 N N N N N N 49.716 -131.145 30.669 -15.167 1.424  1.358  H49 QOH 87 
QOH H50 H50 H 0 1 N N N N N N 47.870 -130.543 33.831 -14.246 1.076  -0.938 H50 QOH 88 
QOH H51 H51 H 0 1 N N N N N N 48.371 -129.826 32.262 -13.375 -0.426 -1.329 H51 QOH 89 
QOH H52 H52 H 0 1 N N N N N N 47.136 -131.129 32.300 -15.134 -0.461 -1.061 H52 QOH 90 
# 
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 
QOH C11 C10 SING N N 1  
QOH C10 C40 SING N N 2  
QOH C10 C9  SING N N 3  
QOH C8  C9  SING N N 4  
QOH C8  C7  SING N N 5  
QOH C6  C7  SING N N 6  
QOH C6  C5  SING N N 7  
QOH C1  C2  SING N N 8  
QOH C1  C12 SING N N 9  
QOH C3  C2  SING N N 10 
QOH C3  C4  SING N N 11 
QOH O35 C34 SING N N 12 
QOH C12 N13 SING N N 13 
QOH C12 O37 DOUB N N 14 
QOH C5  C4  SING N N 15 
QOH N13 C14 SING N N 16 
QOH C34 C14 SING N N 17 
QOH C34 C36 SING N N 18 
QOH C14 C15 SING N N 19 
QOH C15 O33 DOUB N N 20 
QOH C15 N16 SING N N 21 
QOH N16 C17 SING N N 22 
QOH C17 C18 SING N N 23 
QOH C17 C31 SING N N 24 
QOH O20 C19 SING N N 25 
QOH C18 C19 SING N N 26 
QOH O32 C31 DOUB N N 27 
QOH C31 N30 SING N N 28 
QOH C19 C21 SING N N 29 
QOH C21 C22 SING N N 30 
QOH N30 C28 SING N N 31 
QOH C22 N23 SING N N 32 
QOH N23 C24 SING N N 33 
QOH C28 C29 SING N N 34 
QOH C28 C27 SING N N 35 
QOH C26 C24 SING N N 36 
QOH C26 C27 SING N N 37 
QOH C24 O25 DOUB N N 38 
QOH C4  H1  SING N N 39 
QOH C4  H2  SING N N 40 
QOH C5  H3  SING N N 41 
QOH C5  H4  SING N N 42 
QOH C6  H5  SING N N 43 
QOH C6  H6  SING N N 44 
QOH C7  H7  SING N N 45 
QOH C7  H8  SING N N 46 
QOH C8  H9  SING N N 47 
QOH C8  H10 SING N N 48 
QOH C10 H11 SING N N 49 
QOH C17 H12 SING N N 50 
QOH C21 H13 SING N N 51 
QOH C21 H14 SING N N 52 
QOH C22 H15 SING N N 53 
QOH C22 H16 SING N N 54 
QOH C26 H17 SING N N 55 
QOH C26 H18 SING N N 56 
QOH C28 H19 SING N N 57 
QOH C27 H20 SING N N 58 
QOH C27 H21 SING N N 59 
QOH C29 H22 SING N N 60 
QOH C29 H23 SING N N 61 
QOH C29 H24 SING N N 62 
QOH N30 H25 SING N N 63 
QOH N23 H26 SING N N 64 
QOH C19 H27 SING N N 65 
QOH O20 H28 SING N N 66 
QOH C18 H29 SING N N 67 
QOH C18 H30 SING N N 68 
QOH N16 H31 SING N N 69 
QOH C14 H32 SING N N 70 
QOH C34 H33 SING N N 71 
QOH C36 H34 SING N N 72 
QOH C36 H35 SING N N 73 
QOH C36 H36 SING N N 74 
QOH O35 H37 SING N N 75 
QOH N13 H38 SING N N 76 
QOH C1  H39 SING N N 77 
QOH C1  H40 SING N N 78 
QOH C2  H41 SING N N 79 
QOH C2  H42 SING N N 80 
QOH C3  H43 SING N N 81 
QOH C3  H44 SING N N 82 
QOH C9  H45 SING N N 83 
QOH C9  H46 SING N N 84 
QOH C11 H47 SING N N 85 
QOH C11 H48 SING N N 86 
QOH C11 H49 SING N N 87 
QOH C40 H50 SING N N 88 
QOH C40 H51 SING N N 89 
QOH C40 H52 SING N N 90 
# 
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 
QOH InChI            InChI                1.03  "InChI=1S/C28H52N4O6/c1-19(2)12-10-8-6-5-7-9-11-13-25(36)32-26(21(4)33)28(38)31-23-18-22(34)16-17-29-24(35)15-14-20(3)30-27(23)37/h19-23,26,33-34H,5-18H2,1-4H3,(H,29,35)(H,30,37)(H,31,38)(H,32,36)/t20-,21+,22-,23-,26-/m0/s1" 
QOH InChIKey         InChI                1.03  UIOLVRCVADVWOP-CTVYPFPQSA-N                                                                                                                                                                                                      
QOH SMILES_CANONICAL CACTVS               3.385 "CC(C)CCCCCCCCCC(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@H]1C[C@@H](O)CCNC(=O)CC[C@H](C)NC1=O"                                                                                                                                            
QOH SMILES           CACTVS               3.385 "CC(C)CCCCCCCCCC(=O)N[CH]([CH](C)O)C(=O)N[CH]1C[CH](O)CCNC(=O)CC[CH](C)NC1=O"                                                                                                                                                    
QOH SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "C[C@H]1CCC(=O)NCC[C@@H](C[C@@H](C(=O)N1)NC(=O)[C@H]([C@@H](C)O)NC(=O)CCCCCCCCCC(C)C)O"                                                                                                                                          
QOH SMILES           "OpenEye OEToolkits" 2.0.7 "CC1CCC(=O)NCCC(CC(C(=O)N1)NC(=O)C(C(C)O)NC(=O)CCCCCCCCCC(C)C)O"                                                                                                                                                                 
# 
_pdbx_chem_comp_identifier.comp_id           QOH 
_pdbx_chem_comp_identifier.type              "SYSTEMATIC NAME" 
_pdbx_chem_comp_identifier.program           "OpenEye OEToolkits" 
_pdbx_chem_comp_identifier.program_version   2.0.7 
_pdbx_chem_comp_identifier.identifier        "11-methyl-~{N}-[(2~{S},3~{R})-1-[[(5~{S},8~{S},10~{S})-5-methyl-10-oxidanyl-2,7-bis(oxidanylidene)-1,6-diazacyclododec-8-yl]amino]-3-oxidanyl-1-oxidanylidene-butan-2-yl]dodecanamide" 
# 
loop_
_pdbx_chem_comp_synonyms.ordinal 
_pdbx_chem_comp_synonyms.comp_id 
_pdbx_chem_comp_synonyms.name 
_pdbx_chem_comp_synonyms.provenance 
_pdbx_chem_comp_synonyms.type 
1 QOH "Syrbactin inhibitor" ? ? 
2 QOH HB333                 ? ? 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
QOH "Create component" 2020-07-09 PDBE 
QOH "Initial release"  2021-05-19 RCSB 
QOH "Modify PCM"       2024-09-27 PDBE 
# 
_pdbx_chem_comp_pcm.pcm_id                             1 
_pdbx_chem_comp_pcm.comp_id                            QOH 
_pdbx_chem_comp_pcm.modified_residue_id                THR 
_pdbx_chem_comp_pcm.type                               None 
_pdbx_chem_comp_pcm.category                           Lipid/lipid-like 
_pdbx_chem_comp_pcm.position                           "Amino-acid side chain" 
_pdbx_chem_comp_pcm.polypeptide_position               "Any position" 
_pdbx_chem_comp_pcm.comp_id_linking_atom               C27 
_pdbx_chem_comp_pcm.modified_residue_id_linking_atom   OG1 
_pdbx_chem_comp_pcm.uniprot_specific_ptm_accession     ? 
_pdbx_chem_comp_pcm.uniprot_generic_ptm_accession      ? 
# 
