data_WMI
# 
_chem_comp.id                                    WMI 
_chem_comp.name                                  "(4~{S},9~{S},10~{S})-4-methyl-9,10,16,18-tetrakis(oxidanyl)-3-oxabicyclo[12.4.0]octadeca-1(14),15,17-triene-2,8-dione" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C18 H24 O7" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2023-10-09 
_chem_comp.pdbx_modified_date                    2025-04-11 
_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                        352.379 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     WMI 
_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        8QR7 
_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 
WMI C1  C1  C 0 1 N N N N N N -14.683 11.666 38.444 0.758  -3.446 -1.252 C1  WMI 1  
WMI C2  C2  C 0 1 N N S N N N -14.268 11.344 39.867 0.407  -3.193 0.212  C2  WMI 2  
WMI C3  C3  C 0 1 N N N N N N -12.835 11.765 40.176 1.547  -2.522 0.965  C3  WMI 3  
WMI C4  C4  C 0 1 N N N N N N -12.286 11.432 41.554 2.618  -1.970 0.031  C4  WMI 4  
WMI C6  C5  C 0 1 N N N N N N -10.782 13.518 41.652 3.737  0.236  0.214  C6  WMI 5  
WMI C7  C6  C 0 1 N N S N N N -10.818 14.408 42.891 2.727  1.311  0.526  C7  WMI 6  
WMI C8  C7  C 0 1 N N S N N N -12.203 14.320 43.525 2.395  2.091  -0.745 C8  WMI 7  
WMI C9  C8  C 0 1 N N N N N N -13.271 14.801 42.544 1.178  2.981  -0.510 C9  WMI 8  
WMI C10 C9  C 0 1 N N N N N N -14.633 14.334 42.947 -0.122 2.218  -0.747 C10 WMI 9  
WMI C11 C10 C 0 1 N N N N N N -15.691 14.582 41.944 -0.739 1.816  0.595  C11 WMI 10 
WMI C12 C11 C 0 1 Y N N N N N -16.971 13.845 42.270 -2.026 1.068  0.356  C12 WMI 11 
WMI C13 C12 C 0 1 Y N N N N N -17.889 14.479 43.103 -3.211 1.772  0.345  C13 WMI 12 
WMI C14 C13 C 0 1 Y N N N N N -19.100 13.884 43.439 -4.419 1.115  0.135  C14 WMI 13 
WMI C15 C14 C 0 1 Y N N N N N -19.408 12.632 42.957 -4.440 -0.257 -0.063 C15 WMI 14 
WMI C16 C15 C 0 1 Y N N N N N -18.509 11.982 42.126 -3.257 -0.976 -0.052 C16 WMI 15 
WMI C17 C16 C 0 1 Y N N N N N -17.277 12.556 41.766 -2.034 -0.313 0.150  C17 WMI 16 
WMI C18 C17 C 0 1 N N N N N N -16.399 11.704 40.917 -0.778 -1.085 0.118  C18 WMI 17 
WMI C5  C18 C 0 1 N N N N N N -10.920 12.026 41.820 3.610  -1.126 0.845  C5  WMI 18 
WMI O1  O1  O 0 1 N N N N N N -10.646 14.025 40.556 4.652  0.468  -0.539 O1  WMI 19 
WMI O2  O2  O 0 1 N N N N N N -10.563 15.763 42.589 3.274  2.201  1.503  O2  WMI 20 
WMI O3  O3  O 0 1 N N N N N N -12.268 15.142 44.701 2.158  1.189  -1.824 O3  WMI 21 
WMI O4  O4  O 0 1 N N N N N N -19.976 14.538 44.265 -5.580 1.818  0.124  O4  WMI 22 
WMI O5  O5  O 0 1 N N N N N N -18.884 10.760 41.669 -3.289 -2.319 -0.244 O5  WMI 23 
WMI O6  O6  O 0 1 N N N N N N -16.773 10.651 40.464 0.275  -0.512 -0.057 O6  WMI 24 
WMI O7  O7  O 0 1 N N N N N N -15.129 12.097 40.785 -0.808 -2.414 0.306  O7  WMI 25 
WMI H1  H1  H 0 1 N N N N N N -15.721 11.341 38.282 1.632  -4.095 -1.308 H1  WMI 26 
WMI H2  H2  H 0 1 N N N N N N -14.609 12.751 38.277 -0.084 -3.926 -1.750 H2  WMI 27 
WMI H3  H3  H 0 1 N N N N N N -14.020 11.140 37.741 0.978  -2.498 -1.742 H3  WMI 28 
WMI H4  H4  H 0 1 N N N N N N -14.377 10.264 40.045 0.217  -4.172 0.686  H4  WMI 29 
WMI H6  H5  H 0 1 N N N N N N -12.182 11.280 39.435 1.153  -1.710 1.583  H6  WMI 30 
WMI H5  H6  H 0 1 N N N N N N -12.779 12.857 40.054 2.010  -3.254 1.640  H5  WMI 31 
WMI H7  H7  H 0 1 N N N N N N -12.986 11.817 42.310 3.172  -2.788 -0.434 H7  WMI 32 
WMI H41 H8  H 0 1 N N N N N N -12.214 10.338 41.645 2.177  -1.333 -0.733 H41 WMI 33 
WMI H9  H9  H 0 1 N N N N N N -10.077 14.034 43.613 1.823  0.852  0.924  H9  WMI 34 
WMI H11 H10 H 0 1 N N N N N N -12.408 13.271 43.786 3.253  2.725  -1.001 H11 WMI 35 
WMI H13 H11 H 0 1 N N N N N N -13.263 15.901 42.517 1.196  3.359  0.514  H13 WMI 36 
WMI H14 H12 H 0 1 N N N N N N -13.040 14.408 41.543 1.222  3.836  -1.194 H14 WMI 37 
WMI H16 H13 H 0 1 N N N N N N -14.583 13.251 43.133 -0.826 2.872  -1.274 H16 WMI 38 
WMI H15 H14 H 0 1 N N N N N N -14.913 14.853 43.876 0.048  1.334  -1.351 H15 WMI 39 
WMI H17 H15 H 0 1 N N N N N N -15.902 15.661 41.911 -0.047 1.197  1.157  H17 WMI 40 
WMI H18 H16 H 0 1 N N N N N N -15.331 14.249 40.959 -0.957 2.720  1.171  H18 WMI 41 
WMI H19 H17 H 0 1 N N N N N N -17.655 15.457 43.498 -3.199 2.840  0.502  H19 WMI 42 
WMI H21 H18 H 0 1 N N N N N N -20.342 12.160 43.224 -5.379 -0.766 -0.227 H21 WMI 43 
WMI H8  H19 H 0 1 N N N N N N -10.647 11.781 42.857 3.243  -1.025 1.865  H8  WMI 44 
WMI H51 H20 H 0 1 N N N N N N -10.209 11.547 41.131 4.580  -1.619 0.850  H51 WMI 45 
WMI H10 H21 H 0 1 N N N N N N -10.452 15.863 41.651 3.507  1.774  2.338  H10 WMI 46 
WMI H12 H22 H 0 1 N N N N N N -13.134 15.078 45.085 2.911  0.619  -2.033 H12 WMI 47 
WMI H20 H23 H 0 1 N N N N N N -20.749 14.002 44.396 -5.833 2.146  -0.750 H20 WMI 48 
WMI H22 H24 H 0 1 N N N N N N -18.202 10.408 41.109 -3.215 -2.585 -1.171 H22 WMI 49 
# 
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 
WMI C1  C2  SING N N 1  
WMI C2  C3  SING N N 2  
WMI C2  O7  SING N N 3  
WMI C3  C4  SING N N 4  
WMI C4  C5  SING N N 5  
WMI C5  C6  SING N N 6  
WMI C6  O1  DOUB N N 7  
WMI C6  C7  SING N N 8  
WMI C7  O2  SING N N 9  
WMI C7  C8  SING N N 10 
WMI C8  O3  SING N N 11 
WMI C8  C9  SING N N 12 
WMI C9  C10 SING N N 13 
WMI C10 C11 SING N N 14 
WMI C11 C12 SING N N 15 
WMI C12 C13 SING Y N 16 
WMI C12 C17 DOUB Y N 17 
WMI C13 C14 DOUB Y N 18 
WMI C14 O4  SING N N 19 
WMI C14 C15 SING Y N 20 
WMI C15 C16 DOUB Y N 21 
WMI C16 O5  SING N N 22 
WMI C16 C17 SING Y N 23 
WMI C17 C18 SING N N 24 
WMI C18 O6  DOUB N N 25 
WMI C18 O7  SING N N 26 
WMI C1  H1  SING N N 27 
WMI C1  H2  SING N N 28 
WMI C1  H3  SING N N 29 
WMI C2  H4  SING N N 30 
WMI C3  H6  SING N N 31 
WMI C3  H5  SING N N 32 
WMI C4  H7  SING N N 33 
WMI C4  H41 SING N N 34 
WMI C7  H9  SING N N 35 
WMI C8  H11 SING N N 36 
WMI C9  H13 SING N N 37 
WMI C9  H14 SING N N 38 
WMI C10 H16 SING N N 39 
WMI C10 H15 SING N N 40 
WMI C11 H17 SING N N 41 
WMI C11 H18 SING N N 42 
WMI C13 H19 SING N N 43 
WMI C15 H21 SING N N 44 
WMI C5  H8  SING N N 45 
WMI C5  H51 SING N N 46 
WMI O2  H10 SING N N 47 
WMI O3  H12 SING N N 48 
WMI O4  H20 SING N N 49 
WMI O5  H22 SING N N 50 
# 
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 
WMI InChI            InChI                1.06  "InChI=1S/C18H24O7/c1-10-4-2-6-13(20)17(23)14(21)7-3-5-11-8-12(19)9-15(22)16(11)18(24)25-10/h8-10,14,17,19,21-23H,2-7H2,1H3/t10-,14-,17?/m0/s1" 
WMI InChIKey         InChI                1.06  HLPZXKVMGLUVBS-GNAKQSIWSA-N                                                                                                                     
WMI SMILES_CANONICAL CACTVS               3.385 "C[C@H]1CCCC(=O)[C@@H](O)[C@@H](O)CCCc2cc(O)cc(O)c2C(=O)O1"                                                                                     
WMI SMILES           CACTVS               3.385 "C[CH]1CCCC(=O)[CH](O)[CH](O)CCCc2cc(O)cc(O)c2C(=O)O1"                                                                                          
WMI SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "C[C@H]1CCCC(=O)[C@H]([C@H](CCCc2cc(cc(c2C(=O)O1)O)O)O)O"                                                                                       
WMI SMILES           "OpenEye OEToolkits" 2.0.7 "CC1CCCC(=O)C(C(CCCc2cc(cc(c2C(=O)O1)O)O)O)O"                                                                                                   
# 
_pdbx_chem_comp_identifier.comp_id           WMI 
_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        "(4~{S},9~{S},10~{S})-4-methyl-9,10,16,18-tetrakis(oxidanyl)-3-oxabicyclo[12.4.0]octadeca-1(14),15,17-triene-2,8-dione" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
WMI "Create component" 2023-10-09 PDBE 
WMI "Modify PCM"       2024-09-27 PDBE 
WMI "Initial release"  2025-04-16 RCSB 
# 
_pdbx_chem_comp_pcm.pcm_id                             1 
_pdbx_chem_comp_pcm.comp_id                            WMI 
_pdbx_chem_comp_pcm.modified_residue_id                CYS 
_pdbx_chem_comp_pcm.type                               None 
_pdbx_chem_comp_pcm.category                           "Covalent chemical modification" 
_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               C4 
_pdbx_chem_comp_pcm.modified_residue_id_linking_atom   SG 
_pdbx_chem_comp_pcm.uniprot_specific_ptm_accession     ? 
_pdbx_chem_comp_pcm.uniprot_generic_ptm_accession      ? 
# 
