data_GBM
#

_chem_comp.id                                   GBM
_chem_comp.name                                 "5-chloro-N-(2-{4-[(cyclohexylcarbamoyl)sulfamoyl]phenyl}ethyl)-2-methoxybenzamide"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C23 H28 Cl N3 O5 S"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        "Glibenclamide; Glyburide"
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2015-04-03
_chem_comp.pdbx_modified_date                   2021-03-13
_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                       494.004
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    GBM
_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       4YVP
_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
GBM  O3   O1   O   0  1  N  N  N  -52.101  -6.447  42.294   4.821   0.201  -0.816  O3   GBM   1  
GBM  O4   O2   O   0  1  N  N  N  -49.747  -4.996  45.457   3.931   3.694   1.270  O4   GBM   2  
GBM  O5   O3   O   0  1  N  N  N  -48.017  -4.488  43.763   4.281   2.836  -1.051  O5   GBM   3  
GBM  O6   O4   O   0  1  N  N  N  -52.991   1.840  40.420  -4.766   1.761  -0.668  O6   GBM   4  
GBM  CL1  CL1  CL  0  0  N  N  N  -54.301   5.888  37.473  -7.474  -3.681   0.918  CL1  GBM   5  
GBM  S2   S1   S   0  1  N  N  N  -49.395  -4.554  44.143   4.002   2.633   0.327  S2   GBM   6  
GBM  O7   O5   O   0  1  N  N  N  -56.204   3.422  42.430  -7.236   1.838  -1.067  O7   GBM   7  
GBM  N8   N1   N   0  1  N  N  N  -52.096  -5.259  44.267   6.363  -0.400   0.666  N8   GBM   8  
GBM  N9   N2   N   0  1  N  N  N  -50.147  -5.538  43.065   5.155   1.585   0.889  N9   GBM   9  
GBM  N10  N3   N   0  1  N  N  N  -54.220   1.769  42.296  -3.694  -0.006   0.145  N10  GBM  10  
GBM  C11  C1   C   0  1  N  N  N  -53.508  -5.354  44.646   6.656  -1.630  -0.073  C11  GBM  11  
GBM  C12  C2   C   0  1  N  N  N  -54.138  -6.676  44.236   7.233  -2.675   0.885  C12  GBM  12  
GBM  C13  C3   C   0  1  N  N  N  -54.295  -4.183  44.092   7.674  -1.333  -1.176  C13  GBM  13  
GBM  C14  C4   C   0  1  N  N  N  -55.616  -6.502  43.892   7.539  -3.960   0.113  C14  GBM  14  
GBM  C15  C5   C   0  1  N  N  N  -55.698  -4.133  44.686   7.980  -2.618  -1.947  C15  GBM  15  
GBM  C16  C6   C   0  1  N  N  N  -56.287  -5.525  44.837   8.556  -3.663  -0.990  C16  GBM  16  
GBM  C17  C7   C   0  1  N  N  N  -51.507  -5.813  43.162   5.424   0.453   0.209  C17  GBM  17  
GBM  C18  C8   C   0  1  Y  N  N  -50.121  -2.971  43.884   2.454   1.796   0.404  C18  GBM  18  
GBM  C19  C9   C   0  1  Y  N  N  -51.460  -0.566  43.498   0.024   0.481   0.524  C19  GBM  19  
GBM  C20  C10  C   0  1  N  N  N  -52.200   0.736  43.286  -1.300  -0.235   0.589  C20  GBM  20  
GBM  C21  C11  C   0  1  Y  N  N  -50.510  -2.597  42.610   2.016   1.051  -0.676  C21  GBM  21  
GBM  C22  C12  C   0  1  Y  N  N  -50.377  -2.146  44.966   1.679   1.878   1.546  C22  GBM  22  
GBM  C23  C13  C   0  1  Y  N  N  -51.181  -1.401  42.429   0.802   0.394  -0.616  C23  GBM  23  
GBM  C24  C14  C   0  1  Y  N  N  -51.048  -0.952  44.764   0.464   1.221   1.606  C24  GBM  24  
GBM  C25  C15  C   0  1  N  N  N  -53.617   0.534  42.781  -2.407   0.691   0.081  C25  GBM  25  
GBM  C26  C16  C   0  1  N  N  N  -53.896   2.298  41.113  -4.819   0.619  -0.255  C26  GBM  26  
GBM  C27  C17  C   0  1  Y  N  N  -54.691   3.475  40.637  -6.115  -0.083  -0.190  C27  GBM  27  
GBM  C28  C18  C   0  1  Y  N  N  -55.814   4.025  41.266  -7.288   0.563  -0.605  C28  GBM  28  
GBM  C29  C19  C   0  1  Y  N  N  -54.245   4.056  39.449  -6.180  -1.397   0.279  C29  GBM  29  
GBM  C30  C20  C   0  1  Y  N  N  -56.469   5.118  40.721  -8.501  -0.106  -0.541  C30  GBM  30  
GBM  C31  C21  C   0  1  Y  N  N  -54.904   5.150  38.930  -7.394  -2.048   0.336  C31  GBM  31  
GBM  C32  C22  C   0  1  Y  N  N  -56.011   5.685  39.546  -8.552  -1.403  -0.071  C32  GBM  32  
GBM  C33  C23  C   0  1  N  N  N  -57.339   3.966  43.101  -8.471   2.432  -1.472  C33  GBM  33  
GBM  H1   H1   H   0  1  N  N  N  -51.502  -4.736  44.878   6.844  -0.199   1.484  H1   GBM  34  
GBM  H2   H2   H   0  1  N  N  N  -49.616  -5.948  42.323   5.636   1.786   1.707  H2   GBM  35  
GBM  H3   H3   H   0  1  N  N  N  -54.897   2.235  42.866  -3.736  -0.917   0.475  H3   GBM  36  
GBM  H4   H4   H   0  1  N  N  N  -53.566  -5.294  45.743   5.738  -2.014  -0.519  H4   GBM  37  
GBM  H5   H5   H   0  1  N  N  N  -54.045  -7.391  45.067   8.150  -2.292   1.331  H5   GBM  38  
GBM  H6   H6   H   0  1  N  N  N  -53.608  -7.068  43.355   6.507  -2.887   1.671  H6   GBM  39  
GBM  H7   H7   H   0  1  N  N  N  -53.768  -3.249  44.336   7.263  -0.589  -1.858  H7   GBM  40  
GBM  H8   H8   H   0  1  N  N  N  -54.371  -4.286  43.000   8.591  -0.949  -0.730  H8   GBM  41  
GBM  H9   H9   H   0  1  N  N  N  -55.703  -6.123  42.863   7.950  -4.704   0.796  H9   GBM  42  
GBM  H10  H10  H   0  1  N  N  N  -56.119  -7.477  43.967   6.621  -4.344  -0.333  H10  GBM  43  
GBM  H11  H11  H   0  1  N  N  N  -55.651  -3.655  45.676   7.062  -3.001  -2.393  H11  GBM  44  
GBM  H12  H12  H   0  1  N  N  N  -56.346  -3.540  44.024   8.705  -2.406  -2.733  H12  GBM  45  
GBM  H13  H13  H   0  1  N  N  N  -57.363  -5.487  44.611   9.474  -3.279  -0.544  H13  GBM  46  
GBM  H14  H14  H   0  1  N  N  N  -56.141  -5.867  45.872   8.775  -4.578  -1.539  H14  GBM  47  
GBM  H15  H15  H   0  1  N  N  N  -51.647   1.338  42.550  -1.260  -1.130  -0.033  H15  GBM  48  
GBM  H16  H16  H   0  1  N  N  N  -52.242   1.276  44.244  -1.508  -0.519   1.621  H16  GBM  49  
GBM  H17  H17  H   0  1  N  N  N  -50.292  -3.233  41.765   2.624   0.983  -1.566  H17  GBM  50  
GBM  H18  H18  H   0  1  N  N  N  -50.057  -2.431  45.957   2.022   2.456   2.391  H18  GBM  51  
GBM  H19  H19  H   0  1  N  N  N  -51.493  -1.113  41.436   0.460  -0.187  -1.459  H19  GBM  52  
GBM  H20  H20  H   0  1  N  N  N  -51.254  -0.310  45.608  -0.143   1.289   2.496  H20  GBM  53  
GBM  H21  H21  H   0  1  N  N  N  -54.232   0.141  43.604  -2.198   0.975  -0.950  H21  GBM  54  
GBM  H22  H22  H   0  1  N  N  N  -53.597  -0.195  41.958  -2.447   1.585   0.703  H22  GBM  55  
GBM  H23  H23  H   0  1  N  N  N  -53.385   3.649  38.937  -5.280  -1.903   0.596  H23  GBM  56  
GBM  H24  H24  H   0  1  N  N  N  -57.338   5.527  41.215  -9.407   0.389  -0.859  H24  GBM  57  
GBM  H25  H25  H   0  1  N  N  N  -56.516   6.538  39.117  -9.500  -1.919  -0.023  H25  GBM  58  
GBM  H26  H26  H   0  1  N  N  N  -57.538   3.387  44.015  -8.909   1.845  -2.279  H26  GBM  59  
GBM  H27  H27  H   0  1  N  N  N  -57.140   5.014  43.367  -9.158   2.454  -0.625  H27  GBM  60  
GBM  H28  H28  H   0  1  N  N  N  -58.215   3.916  42.438  -8.289   3.449  -1.819  H28  GBM  61  
#   #
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
GBM  CL1  C31  SING  N  N   1  
GBM  C31  C29  DOUB  Y  N   2  
GBM  C31  C32  SING  Y  N   3  
GBM  C29  C27  SING  Y  N   4  
GBM  C32  C30  DOUB  Y  N   5  
GBM  O6   C26  DOUB  N  N   6  
GBM  C27  C26  SING  N  N   7  
GBM  C27  C28  DOUB  Y  N   8  
GBM  C30  C28  SING  Y  N   9  
GBM  C26  N10  SING  N  N  10  
GBM  C28  O7   SING  N  N  11  
GBM  O3   C17  DOUB  N  N  12  
GBM  N10  C25  SING  N  N  13  
GBM  C23  C21  DOUB  Y  N  14  
GBM  C23  C19  SING  Y  N  15  
GBM  O7   C33  SING  N  N  16  
GBM  C21  C18  SING  Y  N  17  
GBM  C25  C20  SING  N  N  18  
GBM  N9   C17  SING  N  N  19  
GBM  N9   S2   SING  N  N  20  
GBM  C17  N8   SING  N  N  21  
GBM  C20  C19  SING  N  N  22  
GBM  C19  C24  DOUB  Y  N  23  
GBM  O5   S2   DOUB  N  N  24  
GBM  C18  S2   SING  N  N  25  
GBM  C18  C22  DOUB  Y  N  26  
GBM  C14  C12  SING  N  N  27  
GBM  C14  C16  SING  N  N  28  
GBM  C13  C11  SING  N  N  29  
GBM  C13  C15  SING  N  N  30  
GBM  S2   O4   DOUB  N  N  31  
GBM  C12  C11  SING  N  N  32  
GBM  N8   C11  SING  N  N  33  
GBM  C15  C16  SING  N  N  34  
GBM  C24  C22  SING  Y  N  35  
GBM  N8   H1   SING  N  N  36  
GBM  N9   H2   SING  N  N  37  
GBM  N10  H3   SING  N  N  38  
GBM  C11  H4   SING  N  N  39  
GBM  C12  H5   SING  N  N  40  
GBM  C12  H6   SING  N  N  41  
GBM  C13  H7   SING  N  N  42  
GBM  C13  H8   SING  N  N  43  
GBM  C14  H9   SING  N  N  44  
GBM  C14  H10  SING  N  N  45  
GBM  C15  H11  SING  N  N  46  
GBM  C15  H12  SING  N  N  47  
GBM  C16  H13  SING  N  N  48  
GBM  C16  H14  SING  N  N  49  
GBM  C20  H15  SING  N  N  50  
GBM  C20  H16  SING  N  N  51  
GBM  C21  H17  SING  N  N  52  
GBM  C22  H18  SING  N  N  53  
GBM  C23  H19  SING  N  N  54  
GBM  C24  H20  SING  N  N  55  
GBM  C25  H21  SING  N  N  56  
GBM  C25  H22  SING  N  N  57  
GBM  C29  H23  SING  N  N  58  
GBM  C30  H24  SING  N  N  59  
GBM  C32  H25  SING  N  N  60  
GBM  C33  H26  SING  N  N  61  
GBM  C33  H27  SING  N  N  62  
GBM  C33  H28  SING  N  N  63  
#   #
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
GBM  SMILES            ACDLabs               12.01  "O=C(NC1CCCCC1)NS(=O)(=O)c3ccc(CCNC(=O)c2c(OC)ccc(Cl)c2)cc3"  
GBM  InChI             InChI                 1.03   "InChI=1S/C23H28ClN3O5S/c1-32-21-12-9-17(24)15-20(21)22(28)25-14-13-16-7-10-19(11-8-16)33(30,31)27-23(29)26-18-5-3-2-4-6-18/h7-12,15,18H,2-6,13-14H2,1H3,(H,25,28)(H2,26,27,29)"  
GBM  InChIKey          InChI                 1.03   ZNNLBTZKUZBEKO-UHFFFAOYSA-N  
GBM  SMILES_CANONICAL  CACTVS                3.385  "COc1ccc(Cl)cc1C(=O)NCCc2ccc(cc2)[S](=O)(=O)NC(=O)NC3CCCCC3"  
GBM  SMILES            CACTVS                3.385  "COc1ccc(Cl)cc1C(=O)NCCc2ccc(cc2)[S](=O)(=O)NC(=O)NC3CCCCC3"  
GBM  SMILES_CANONICAL  "OpenEye OEToolkits"  1.9.2  "COc1ccc(cc1C(=O)NCCc2ccc(cc2)S(=O)(=O)NC(=O)NC3CCCCC3)Cl"  
GBM  SMILES            "OpenEye OEToolkits"  1.9.2  "COc1ccc(cc1C(=O)NCCc2ccc(cc2)S(=O)(=O)NC(=O)NC3CCCCC3)Cl"  
#   #
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
GBM  "SYSTEMATIC NAME"  ACDLabs               12.01  "5-chloro-N-(2-{4-[(cyclohexylcarbamoyl)sulfamoyl]phenyl}ethyl)-2-methoxybenzamide"  
GBM  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.9.2  "5-chloranyl-N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-2-methoxy-benzamide"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
GBM  "Create component"  2015-04-03  PDBJ  
GBM  "Initial release"   2015-11-25  RCSB  
GBM  "Modify synonyms"   2016-03-28  RCSB  
GBM  "Modify synonyms"   2021-03-13  RCSB  
#   #
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  GBM  Glibenclamide  PDB  ?  
2  GBM  Glyburide      PDB  ?  
##
