data_LFL
# 
_chem_comp.id                                    LFL 
_chem_comp.name                                  "(2S,3R,4R,5S,6R)-2-[4-chloranyl-3-[(4-ethoxyphenyl)methyl]phenyl]-6-methylsulfanyl-oxane-3,4,5-triol" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H25 Cl O5 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         Sotagliflozin 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2022-11-18 
_chem_comp.pdbx_modified_date                    2023-11-10 
_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                        424.938 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     LFL 
_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        8HG7 
_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 
LFL C1  C1  C  0 1 Y N N N N N 67.175 66.795 81.008 5.152  1.070  -0.834 C1  LFL 1  
LFL C2  C2  C  0 1 Y N N N N N 66.779 67.159 79.722 5.212  -0.010 0.034  C2  LFL 2  
LFL C3  C3  C  0 1 Y N N N N N 67.389 66.612 78.621 4.260  -1.009 -0.040 C3  LFL 3  
LFL C4  C4  C  0 1 Y N N N N N 68.406 65.686 78.755 3.248  -0.932 -0.979 C4  LFL 4  
LFL C5  C5  C  0 1 Y N N N N N 68.795 65.326 80.040 3.186  0.144  -1.845 C5  LFL 5  
LFL C6  C6  C  0 1 Y N N N N N 68.193 65.868 81.164 4.135  1.145  -1.775 C6  LFL 6  
LFL C7  C7  C  0 1 N N N N N N 69.065 65.103 77.526 2.211  -2.023 -1.059 C7  LFL 7  
LFL C8  C8  C  0 1 Y N N N N N 69.447 66.210 76.563 1.055  -1.683 -0.154 C8  LFL 8  
LFL C9  C9  C  0 1 Y N N N N N 70.552 67.022 76.779 1.148  -1.919 1.206  C9  LFL 9  
LFL CL1 CL1 CL 0 0 N N N N N N 71.538 66.733 78.173 2.598  -2.605 1.871  CL1 LFL 10 
LFL C10 C10 C  0 1 Y N N N N N 68.659 66.480 75.446 -0.097 -1.132 -0.682 C10 LFL 11 
LFL C11 C11 C  0 1 Y N N N N N 68.955 67.498 74.544 -1.156 -0.815 0.149  C11 LFL 12 
LFL C12 C12 C  0 1 Y N N N N N 70.076 68.280 74.795 -1.063 -1.051 1.508  C12 LFL 13 
LFL C13 C13 C  0 1 Y N N N N N 70.879 68.057 75.913 0.086  -1.608 2.036  C13 LFL 14 
LFL C14 C14 C  0 1 N N S N N N 68.116 67.764 73.318 -2.409 -0.208 -0.427 C14 LFL 15 
LFL C15 C15 C  0 1 N N R N N N 67.249 66.601 72.806 -3.479 -1.293 -0.579 C15 LFL 16 
LFL C16 C16 C  0 1 N N R N N N 66.476 67.054 71.582 -4.768 -0.657 -1.107 C16 LFL 17 
LFL C17 C17 C  0 1 N N S N N N 65.656 68.299 71.912 -5.203 0.459  -0.152 C17 LFL 18 
LFL C18 C18 C  0 1 N N R N N N 66.566 69.372 72.476 -4.067 1.476  -0.016 C18 LFL 19 
LFL O1  O1  O  0 1 N N N N N N 67.261 68.876 73.621 -2.890 0.813  0.450  O1  LFL 20 
LFL O2  O2  O  0 1 N N N N N N 68.046 65.474 72.452 -3.023 -2.287 -1.499 O2  LFL 21 
LFL O3  O3  O  0 1 N N N N N N 65.024 68.795 70.749 -6.365 1.107  -0.673 O3  LFL 22 
LFL S1  S1  S  0 1 N N N N N N 65.562 70.811 72.868 -4.546 2.763  1.169  S1  LFL 23 
LFL O4  O4  O  0 1 N N N N N N 65.622 65.996 71.187 -5.794 -1.648 -1.183 O4  LFL 24 
LFL C19 C19 C  0 1 N N N N N N 66.955 71.953 73.187 -3.242 4.008  0.969  C19 LFL 25 
LFL O5  O5  O  0 1 N N N N N N 66.626 67.284 82.158 6.084  2.056  -0.759 O5  LFL 26 
LFL C20 C20 C  0 1 N N N N N N 65.861 68.497 82.150 7.102  1.913  0.234  C20 LFL 27 
LFL C21 C21 C  0 1 N N N N N N 65.003 68.485 83.346 8.052  3.110  0.167  C21 LFL 28 
LFL H1  H1  H  0 1 N N N N N N 65.984 67.879 79.591 6.003  -0.071 0.768  H1  LFL 29 
LFL H2  H2  H  0 1 N N N N N N 67.069 66.910 77.634 4.306  -1.850 0.636  H2  LFL 30 
LFL H3  H3  H  0 1 N N N N N N 69.588 64.604 80.166 2.395  0.202  -2.578 H3  LFL 31 
LFL H4  H4  H  0 1 N N N N N N 68.514 65.571 82.152 4.084  1.987  -2.449 H4  LFL 32 
LFL H5  H5  H  0 1 N N N N N N 68.365 64.415 77.030 1.855  -2.111 -2.085 H5  LFL 33 
LFL H6  H6  H  0 1 N N N N N N 69.970 64.553 77.825 2.654  -2.968 -0.744 H6  LFL 34 
LFL H7  H7  H  0 1 N N N N N N 67.782 65.874 75.273 -0.170 -0.947 -1.743 H7  LFL 35 
LFL H8  H8  H  0 1 N N N N N N 70.330 69.076 74.111 -1.891 -0.803 2.156  H8  LFL 36 
LFL H9  H9  H  0 1 N N N N N N 71.741 68.679 76.102 0.159  -1.791 3.098  H9  LFL 37 
LFL H10 H10 H  0 1 N N N N N N 68.795 68.053 72.502 -2.189 0.225  -1.402 H10 LFL 38 
LFL H11 H11 H  0 1 N N N N N N 66.534 66.325 73.595 -3.671 -1.754 0.390  H11 LFL 39 
LFL H12 H12 H  0 1 N N N N N N 67.186 67.297 70.778 -4.589 -0.239 -2.098 H12 LFL 40 
LFL H13 H13 H  0 1 N N N N N N 64.905 68.035 72.671 -5.430 0.033  0.826  H13 LFL 41 
LFL H14 H14 H  0 1 N N N N N N 67.276 69.694 71.700 -3.869 1.931  -0.986 H14 LFL 42 
LFL H15 H15 H  0 1 N N N N N N 68.536 65.181 73.211 -3.653 -3.006 -1.644 H15 LFL 43 
LFL H16 H16 H  0 1 N N N N N N 64.518 69.568 70.968 -6.697 1.826  -0.117 H16 LFL 44 
LFL H17 H17 H  0 1 N N N N N N 66.142 65.227 70.984 -6.642 -1.313 -1.505 H17 LFL 45 
LFL H18 H18 H  0 1 N N N N N N 66.563 72.944 73.458 -2.275 3.562  1.202  H18 LFL 46 
LFL H19 H19 H  0 1 N N N N N N 67.567 71.563 74.013 -3.237 4.367  -0.061 H19 LFL 47 
LFL H20 H20 H  0 1 N N N N N N 67.573 72.039 72.281 -3.430 4.843  1.643  H20 LFL 48 
LFL H21 H21 H  0 1 N N N N N N 66.534 69.366 82.179 6.642  1.868  1.222  H21 LFL 49 
LFL H22 H22 H  0 1 N N N N N N 65.241 68.544 81.243 7.661  0.994  0.052  H22 LFL 50 
LFL H23 H23 H  0 1 N N N N N N 64.399 69.404 83.374 8.512  3.154  -0.820 H23 LFL 51 
LFL H24 H24 H  0 1 N N N N N N 64.338 67.610 83.311 7.494  4.028  0.349  H24 LFL 52 
LFL H25 H25 H  0 1 N N N N N N 65.631 68.432 84.247 8.828  3.000  0.924  H25 LFL 53 
# 
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 
LFL O3  C17 SING N N 1  
LFL O4  C16 SING N N 2  
LFL C16 C17 SING N N 3  
LFL C16 C15 SING N N 4  
LFL C17 C18 SING N N 5  
LFL O2  C15 SING N N 6  
LFL C18 S1  SING N N 7  
LFL C18 O1  SING N N 8  
LFL C15 C14 SING N N 9  
LFL S1  C19 SING N N 10 
LFL C14 O1  SING N N 11 
LFL C14 C11 SING N N 12 
LFL C11 C12 DOUB Y N 13 
LFL C11 C10 SING Y N 14 
LFL C12 C13 SING Y N 15 
LFL C10 C8  DOUB Y N 16 
LFL C13 C9  DOUB Y N 17 
LFL C8  C9  SING Y N 18 
LFL C8  C7  SING N N 19 
LFL C9  CL1 SING N N 20 
LFL C7  C4  SING N N 21 
LFL C3  C4  DOUB Y N 22 
LFL C3  C2  SING Y N 23 
LFL C4  C5  SING Y N 24 
LFL C2  C1  DOUB Y N 25 
LFL C5  C6  DOUB Y N 26 
LFL C1  C6  SING Y N 27 
LFL C1  O5  SING N N 28 
LFL C20 O5  SING N N 29 
LFL C20 C21 SING N N 30 
LFL C2  H1  SING N N 31 
LFL C3  H2  SING N N 32 
LFL C5  H3  SING N N 33 
LFL C6  H4  SING N N 34 
LFL C7  H5  SING N N 35 
LFL C7  H6  SING N N 36 
LFL C10 H7  SING N N 37 
LFL C12 H8  SING N N 38 
LFL C13 H9  SING N N 39 
LFL C14 H10 SING N N 40 
LFL C15 H11 SING N N 41 
LFL C16 H12 SING N N 42 
LFL C17 H13 SING N N 43 
LFL C18 H14 SING N N 44 
LFL O2  H15 SING N N 45 
LFL O3  H16 SING N N 46 
LFL O4  H17 SING N N 47 
LFL C19 H18 SING N N 48 
LFL C19 H19 SING N N 49 
LFL C19 H20 SING N N 50 
LFL C20 H21 SING N N 51 
LFL C20 H22 SING N N 52 
LFL C21 H23 SING N N 53 
LFL C21 H24 SING N N 54 
LFL C21 H25 SING N N 55 
# 
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 
LFL InChI            InChI                1.06  "InChI=1S/C21H25ClO5S/c1-3-26-15-7-4-12(5-8-15)10-14-11-13(6-9-16(14)22)20-18(24)17(23)19(25)21(27-20)28-2/h4-9,11,17-21,23-25H,3,10H2,1-2H3/t17-,18-,19+,20+,21-/m1/s1" 
LFL InChIKey         InChI                1.06  QKDRXGFQVGOQKS-CRSSMBPESA-N                                                                                                                                              
LFL SMILES_CANONICAL CACTVS               3.385 "CCOc1ccc(Cc2cc(ccc2Cl)[C@@H]3O[C@H](SC)[C@@H](O)[C@H](O)[C@H]3O)cc1"                                                                                                    
LFL SMILES           CACTVS               3.385 "CCOc1ccc(Cc2cc(ccc2Cl)[CH]3O[CH](SC)[CH](O)[CH](O)[CH]3O)cc1"                                                                                                           
LFL SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "CCOc1ccc(cc1)Cc2cc(ccc2Cl)[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)SC)O)O)O"                                                                                                  
LFL SMILES           "OpenEye OEToolkits" 2.0.7 "CCOc1ccc(cc1)Cc2cc(ccc2Cl)C3C(C(C(C(O3)SC)O)O)O"                                                                                                                        
# 
_pdbx_chem_comp_identifier.comp_id           LFL 
_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        "(2~{S},3~{R},4~{R},5~{S},6~{R})-2-[4-chloranyl-3-[(4-ethoxyphenyl)methyl]phenyl]-6-methylsulfanyl-oxane-3,4,5-triol" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
LFL "Create component" 2022-11-18 PDBJ 
LFL "Initial release"  2023-11-15 RCSB 
# 
_pdbx_chem_comp_synonyms.ordinal      1 
_pdbx_chem_comp_synonyms.comp_id      LFL 
_pdbx_chem_comp_synonyms.name         Sotagliflozin 
_pdbx_chem_comp_synonyms.provenance   AUTHOR 
_pdbx_chem_comp_synonyms.type         ? 
# 
