data_MC5
#

_chem_comp.id                                   MC5
_chem_comp.name                                 "(5S)-5-({6-[(2-fluorobenzyl)oxy]naphthalen-2-yl}methyl)-1,3-thiazolidine-2,4-dione"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C21 H16 F N O3 S"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        Netoglitazone
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2011-06-22
_chem_comp.pdbx_modified_date                   2021-03-01
_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                       381.420
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    MC5
_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       3B0Q
_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.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
MC5  F     F     F  0  1  N  N  N  -19.323  18.064   -8.649   6.358   2.397   0.668  F     MC5   1  
MC5  N     N     N  0  1  N  N  N  -19.863  19.354  -20.512  -6.888   0.805  -0.198  N     MC5   2  
MC5  S     S     S  0  1  N  N  N  -20.244  19.593  -18.056  -4.437   1.174  -0.664  S     MC5   3  
MC5  C1    C1    C  0  1  Y  N  N  -16.849  17.246  -14.878  -0.567  -0.264   0.647  C1    MC5   4  
MC5  O1    O1    O  0  1  N  N  N  -15.922  17.120  -10.829   3.487  -0.602  -0.093  O1    MC5   5  
MC5  C2    C2    C  0  1  Y  N  N  -17.879  17.117  -13.950  -0.043  -1.459   0.094  C2    MC5   6  
MC5  O2    O2    O  0  1  N  N  N  -17.753  18.533  -20.642  -7.141  -1.387   0.120  O2    MC5   7  
MC5  C3    C3    C  0  1  Y  N  N  -15.531  17.320  -14.455   0.302   0.802   0.939  C3    MC5   8  
MC5  O3    O3    O  0  1  N  N  N  -21.855  20.224  -19.901  -6.395   2.996  -0.558  O3    MC5   9  
MC5  C4    C4    C  0  1  Y  N  N  -17.146  17.287  -16.231  -1.947  -0.168   0.897  C4    MC5  10  
MC5  C5    C5    C  0  1  Y  N  N  -18.468  17.202  -16.651  -2.759  -1.220   0.606  C5    MC5  11  
MC5  C6    C6    C  0  1  Y  N  N  -17.589  17.075  -12.595   1.336  -1.559  -0.151  C6    MC5  12  
MC5  C7    C7    C  0  1  Y  N  N  -16.263  17.154  -12.160   2.152  -0.504   0.145  C7    MC5  13  
MC5  C8    C8    C  0  1  Y  N  N  -19.204  17.037  -14.375  -0.914  -2.523  -0.197  C8    MC5  14  
MC5  C9    C9    C  0  1  Y  N  N  -15.235  17.275  -13.095   1.633   0.674   0.690  C9    MC5  15  
MC5  C10   C10   C  0  1  Y  N  N  -16.888  21.116   -9.971   7.405  -1.246  -0.936  C10   MC5  16  
MC5  C11   C11   C  0  1  Y  N  N  -19.502  17.086  -15.729  -2.244  -2.396   0.063  C11   MC5  17  
MC5  C12   C12   C  0  1  N  N  N  -18.785  17.276  -18.112  -4.238  -1.113   0.876  C12   MC5  18  
MC5  C13   C13   C  0  1  N  N  S  -18.762  18.750  -18.507  -4.943  -0.552  -0.361  C13   MC5  19  
MC5  C14   C14   C  0  1  N  N  N  -18.734  18.856  -20.001  -6.432  -0.434  -0.120  C14   MC5  20  
MC5  C15   C15   C  0  1  Y  N  N  -18.124  21.403   -9.402   8.376  -0.290  -0.701  C15   MC5  21  
MC5  C16   C16   C  0  1  N  N  N  -20.760  19.777  -19.622  -6.073   1.828  -0.466  C16   MC5  22  
MC5  C17   C17   C  0  1  Y  N  N  -18.945  20.371   -8.961   8.025   0.933  -0.163  C17   MC5  23  
MC5  C18   C18   C  0  1  N  N  N  -16.857  17.327   -9.769   4.289   0.533   0.237  C18   MC5  24  
MC5  C19   C19   C  0  1  Y  N  N  -17.297  18.766   -9.659   5.731   0.243  -0.094  C19   MC5  25  
MC5  C20   C20   C  0  1  Y  N  N  -18.526  19.054   -9.086   6.702   1.202   0.142  C20   MC5  26  
MC5  C21   C21   C  0  1  Y  N  N  -16.475  19.803  -10.099   6.083  -0.980  -0.632  C21   MC5  27  
MC5  HN    HN    H  0  1  N  N  N  -20.025  19.406  -21.497  -7.833   0.973  -0.061  HN    MC5  28  
MC5  H3    H3    H  0  1  N  N  N  -14.735  17.412  -15.179  -0.085   1.718   1.360  H3    MC5  29  
MC5  H4    H4    H  0  1  N  N  N  -16.352  17.385  -16.957  -2.360   0.737   1.318  H4    MC5  30  
MC5  H6    H6    H  0  1  N  N  N  -18.388  16.981  -11.875   1.749  -2.464  -0.572  H6    MC5  31  
MC5  H8    H8    H  0  1  N  N  N  -19.999  16.937  -13.650  -0.529  -3.440  -0.619  H8    MC5  32  
MC5  H9    H9    H  0  1  N  N  N  -14.209  17.334  -12.764   2.298   1.494   0.916  H9    MC5  33  
MC5  H10   H10   H  0  1  N  N  N  -16.251  21.918  -10.313   7.680  -2.201  -1.360  H10   MC5  34  
MC5  H11   H11   H  0  1  N  N  N  -20.528  17.035  -16.064  -2.910  -3.216  -0.158  H11   MC5  35  
MC5  H12   H12   H  0  1  N  N  N  -18.037  16.716  -18.692  -4.638  -2.101   1.106  H12   MC5  36  
MC5  H12A  H12A  H  0  0  N  N  N  -19.778  16.846  -18.308  -4.405  -0.447   1.723  H12A  MC5  37  
MC5  H13   H13   H  0  1  N  N  N  -17.887  19.186  -18.002  -4.739  -1.173  -1.234  H13   MC5  38  
MC5  H15   H15   H  0  1  N  N  N  -18.447  22.429   -9.302   9.408  -0.500  -0.939  H15   MC5  39  
MC5  H17   H17   H  0  1  N  N  N  -19.906  20.594   -8.522   8.784   1.680   0.021  H17   MC5  40  
MC5  H18   H18   H  0  1  N  N  N  -17.744  16.705   -9.960   3.952   1.396  -0.337  H18   MC5  41  
MC5  H18A  H18A  H  0  0  N  N  N  -16.380  17.035   -8.822   4.196   0.746   1.302  H18A  MC5  42  
MC5  H21   H21   H  0  1  N  N  N  -15.515  19.580  -10.540   5.326  -1.727  -0.816  H21   MC5  43  
#   #
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
MC5  F    C20   SING  N  N   1  
MC5  N    C14   SING  N  N   2  
MC5  N    C16   SING  N  N   3  
MC5  S    C13   SING  N  N   4  
MC5  S    C16   SING  N  N   5  
MC5  C1   C2    DOUB  Y  N   6  
MC5  C1   C3    SING  Y  N   7  
MC5  C1   C4    SING  Y  N   8  
MC5  O1   C7    SING  N  N   9  
MC5  O1   C18   SING  N  N  10  
MC5  C2   C6    SING  Y  N  11  
MC5  C2   C8    SING  Y  N  12  
MC5  O2   C14   DOUB  N  N  13  
MC5  C3   C9    DOUB  Y  N  14  
MC5  O3   C16   DOUB  N  N  15  
MC5  C4   C5    DOUB  Y  N  16  
MC5  C5   C11   SING  Y  N  17  
MC5  C5   C12   SING  N  N  18  
MC5  C6   C7    DOUB  Y  N  19  
MC5  C7   C9    SING  Y  N  20  
MC5  C8   C11   DOUB  Y  N  21  
MC5  C10  C15   DOUB  Y  N  22  
MC5  C10  C21   SING  Y  N  23  
MC5  C12  C13   SING  N  N  24  
MC5  C13  C14   SING  N  N  25  
MC5  C15  C17   SING  Y  N  26  
MC5  C17  C20   DOUB  Y  N  27  
MC5  C18  C19   SING  N  N  28  
MC5  C19  C20   SING  Y  N  29  
MC5  C19  C21   DOUB  Y  N  30  
MC5  N    HN    SING  N  N  31  
MC5  C3   H3    SING  N  N  32  
MC5  C4   H4    SING  N  N  33  
MC5  C6   H6    SING  N  N  34  
MC5  C8   H8    SING  N  N  35  
MC5  C9   H9    SING  N  N  36  
MC5  C10  H10   SING  N  N  37  
MC5  C11  H11   SING  N  N  38  
MC5  C12  H12   SING  N  N  39  
MC5  C12  H12A  SING  N  N  40  
MC5  C13  H13   SING  N  N  41  
MC5  C15  H15   SING  N  N  42  
MC5  C17  H17   SING  N  N  43  
MC5  C18  H18   SING  N  N  44  
MC5  C18  H18A  SING  N  N  45  
MC5  C21  H21   SING  N  N  46  
#   #
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
MC5  SMILES            ACDLabs               12.01  "Fc1ccccc1COc3ccc2cc(ccc2c3)CC4SC(=O)NC4=O"  
MC5  InChI             InChI                 1.03   "InChI=1S/C21H16FNO3S/c22-18-4-2-1-3-16(18)12-26-17-8-7-14-9-13(5-6-15(14)11-17)10-19-20(24)23-21(25)27-19/h1-9,11,19H,10,12H2,(H,23,24,25)/t19-/m0/s1"  
MC5  InChIKey          InChI                 1.03   PKWDZWYVIHVNKS-IBGZPJMESA-N  
MC5  SMILES_CANONICAL  CACTVS                3.370  "Fc1ccccc1COc2ccc3cc(C[C@@H]4SC(=O)NC4=O)ccc3c2"  
MC5  SMILES            CACTVS                3.370  "Fc1ccccc1COc2ccc3cc(C[CH]4SC(=O)NC4=O)ccc3c2"  
MC5  SMILES_CANONICAL  "OpenEye OEToolkits"  1.7.2  "c1ccc(c(c1)COc2ccc3cc(ccc3c2)C[C@H]4C(=O)NC(=O)S4)F"  
MC5  SMILES            "OpenEye OEToolkits"  1.7.2  "c1ccc(c(c1)COc2ccc3cc(ccc3c2)CC4C(=O)NC(=O)S4)F"  
#   #
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
MC5  "SYSTEMATIC NAME"  ACDLabs               12.01  "(5S)-5-({6-[(2-fluorobenzyl)oxy]naphthalen-2-yl}methyl)-1,3-thiazolidine-2,4-dione"  
MC5  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.7.2  "(5S)-5-[[6-[(2-fluorophenyl)methoxy]naphthalen-2-yl]methyl]-1,3-thiazolidine-2,4-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
MC5  "Create component"  2011-06-22  PDBJ  
MC5  "Modify synonyms"   2021-03-01  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     MC5
_pdbx_chem_comp_synonyms.name        Netoglitazone
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
