data_GN0
#

_chem_comp.id                                   GN0
_chem_comp.name                                 "(2~{R})-5-(2-chlorophenyl)sulfanyl-2-(4-morpholin-4-ylphenyl)-4-oxidanyl-2-thiophen-3-yl-1,3-dihydropyridin-6-one"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C25 H23 Cl N2 O3 S2"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        "inhibitor GNE-140"
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2015-05-19
_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                       499.045
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    GN0
_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       4ZVV
_chem_comp.pdbx_subcomponent_list               ?
_chem_comp.pdbx_processing_site                 RCSB
#   #
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
GN0  C4   C1   C   0  1  Y  N  N  43.400  13.978  24.062  -2.577  -0.459  -1.019  C4   GN0   1  
GN0  C5   C2   C   0  1  Y  N  N  42.071  13.708  24.314  -1.981  -0.446   0.229  C5   GN0   2  
GN0  C6   C3   C   0  1  Y  N  N  41.373  12.895  23.444  -2.759  -0.508   1.371  C6   GN0   3  
GN0  C8   C4   C   0  1  N  N  R  41.335  14.264  25.492  -0.481  -0.363   0.346  C8   GN0   4  
GN0  C9   C5   C   0  1  Y  N  N  42.294  14.898  26.422  -0.064   1.084   0.398  C9   GN0   5  
GN0  C10  C6   C   0  1  Y  N  N  42.617  16.239  26.436   0.049   1.757   1.544  C10  GN0   6  
GN0  C12  C7   C   0  1  Y  N  N  43.823  15.016  28.190   0.589   3.082  -0.516  C12  GN0   7  
GN0  C13  C8   C   0  1  Y  N  N  42.996  14.207  27.446   0.237   1.814  -0.739  C13  GN0   8  
GN0  C3   C9   C   0  1  Y  N  N  44.015  13.435  22.956  -3.951  -0.530  -1.129  C3   GN0   9  
GN0  C1   C10  C   0  1  Y  N  N  41.988  12.356  22.340  -4.134  -0.584   1.268  C1   GN0  10  
GN0  C2   C11  C   0  1  Y  N  N  43.316  12.620  22.086  -4.736  -0.586   0.016  C2   GN0  11  
GN0  N7   N1   N   0  1  N  N  N  43.936  12.066  20.954  -6.127  -0.662  -0.092  N7   GN0  12  
GN0  S11  S1   S   0  1  Y  N  N  43.753  16.643  27.653   0.554   3.409   1.211  S11  GN0  13  
GN0  N14  N2   N   0  1  N  N  N  40.680  13.228  26.238   0.131  -1.001  -0.820  N14  GN0  14  
GN0  C15  C12  C   0  1  N  N  N  39.582  13.481  27.032   1.404  -1.437  -0.771  C15  GN0  15  
GN0  C16  C13  C   0  1  N  N  N  39.078  14.871  27.011   2.138  -1.398   0.497  C16  GN0  16  
GN0  C17  C14  C   0  1  N  N  N  39.409  15.704  26.021   1.466  -1.199   1.647  C17  GN0  17  
GN0  C18  C15  C   0  1  N  N  N  40.333  15.257  24.955  -0.034  -1.061   1.628  C18  GN0  18  
GN0  O19  O1   O   0  1  N  N  N  39.082  16.894  25.816   2.137  -1.123   2.818  O19  GN0  19  
GN0  O20  O2   O   0  1  N  N  N  39.001  12.637  27.700   1.943  -1.861  -1.776  O20  GN0  20  
GN0  S21  S2   S   0  1  N  N  N  37.997  15.301  28.268   3.887  -1.612   0.517  S21  GN0  21  
GN0  C22  C16  C   0  1  Y  N  N  38.961  16.206  29.451   4.471  -0.180  -0.328  C22  GN0  22  
GN0  C23  C17  C   0  1  Y  N  N  40.250  16.629  29.199   3.581   0.820  -0.700  C23  GN0  23  
GN0  C24  C18  C   0  1  Y  N  N  40.949  17.329  30.161   4.042   1.941  -1.362  C24  GN0  24  
GN0  C25  C19  C   0  1  Y  N  N  40.364  17.607  31.379   5.388   2.069  -1.655  C25  GN0  25  
GN0  C26  C20  C   0  1  Y  N  N  39.077  17.187  31.638   6.277   1.076  -1.286  C26  GN0  26  
GN0  C27  C21  C   0  1  Y  N  N  38.383  16.489  30.672   5.825  -0.046  -0.619  C27  GN0  27  
GN0  CL   CL1  CL  0  0  N  N  N  36.769  15.959  30.994   6.942  -1.289  -0.151  CL   GN0  28  
GN0  C29  C22  C   0  1  N  N  N  43.316  10.938  20.268  -6.548  -0.650  -1.501  C29  GN0  29  
GN0  C30  C23  C   0  1  N  N  N  44.402   9.913  19.763  -8.070  -0.795  -1.574  C30  GN0  30  
GN0  O31  O3   O   0  1  N  N  N  45.432  10.745  19.106  -8.681   0.254  -0.818  O31  GN0  31  
GN0  C32  C24  C   0  1  N  N  N  46.136  11.503  20.130  -8.294   0.271   0.559  C32  GN0  32  
GN0  C33  C25  C   0  1  N  N  N  45.182  12.641  20.472  -6.774   0.427   0.654  C33  GN0  33  
GN0  H1   H1   H   0  1  N  N  N  43.958  14.615  24.732  -1.966  -0.411  -1.908  H1   GN0  34  
GN0  H2   H2   H   0  1  N  N  N  40.332  12.680  23.633  -2.291  -0.498   2.344  H2   GN0  35  
GN0  H3   H3   H   0  1  N  N  N  42.197  16.960  25.750  -0.141   1.350   2.526  H3   GN0  36  
GN0  H4   H4   H   0  1  N  N  N  44.438  14.671  29.008   0.857   3.796  -1.280  H4   GN0  37  
GN0  H5   H5   H   0  1  N  N  N  42.890  13.147  27.623   0.190   1.390  -1.731  H5   GN0  38  
GN0  H6   H6   H   0  1  N  N  N  45.056  13.649  22.766  -4.416  -0.540  -2.104  H6   GN0  39  
GN0  H7   H7   H   0  1  N  N  N  41.428  11.722  21.668  -4.741  -0.633   2.160  H7   GN0  40  
GN0  H8   H8   H   0  1  N  N  N  41.031  12.293  26.180  -0.384  -1.112  -1.634  H8   GN0  41  
GN0  H10  H10  H   0  1  N  N  N  40.870  16.130  24.555  -0.354  -0.475   2.489  H10  GN0  42  
GN0  H11  H11  H   0  1  N  N  N  39.752  14.783  24.150  -0.488  -2.051   1.678  H11  GN0  43  
GN0  H12  H12  H   0  1  N  N  N  40.712  16.412  28.247   2.530   0.721  -0.473  H12  GN0  44  
GN0  H13  H13  H   0  1  N  N  N  41.957  17.660  29.960   3.351   2.719  -1.652  H13  GN0  45  
GN0  H14  H14  H   0  1  N  N  N  40.915  18.154  32.130   5.745   2.947  -2.173  H14  GN0  46  
GN0  H15  H15  H   0  1  N  N  N  38.616  17.403  32.590   7.327   1.179  -1.517  H15  GN0  47  
GN0  H16  H16  H   0  1  N  N  N  42.746  11.312  19.405  -6.249   0.292  -1.962  H16  GN0  48  
GN0  H17  H17  H   0  1  N  N  N  42.634  10.426  20.963  -6.076  -1.479  -2.028  H17  GN0  49  
GN0  H18  H18  H   0  1  N  N  N  43.962   9.204  19.046  -8.392  -0.729  -2.614  H18  GN0  50  
GN0  H19  H19  H   0  1  N  N  N  44.834   9.358  20.609  -8.364  -1.761  -1.163  H19  GN0  51  
GN0  H20  H20  H   0  1  N  N  N  46.331  10.878  21.014  -8.778   1.108   1.063  H20  GN0  52  
GN0  H21  H21  H   0  1  N  N  N  47.087  11.895  19.741  -8.594  -0.663   1.033  H21  GN0  53  
GN0  H22  H22  H   0  1  N  N  N  45.625  13.275  21.254  -6.468   0.383   1.700  H22  GN0  54  
GN0  H23  H23  H   0  1  N  N  N  44.989  13.247  19.574  -6.479   1.385   0.228  H23  GN0  55  
GN0  H9   H9   H   0  1  N  N  N  38.489  17.182  26.500   3.099  -1.145   2.722  H9   GN0  56  
#   #
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
GN0  O31  C30  SING  N  N   1  
GN0  O31  C32  SING  N  N   2  
GN0  C30  C29  SING  N  N   3  
GN0  C32  C33  SING  N  N   4  
GN0  C29  N7   SING  N  N   5  
GN0  C33  N7   SING  N  N   6  
GN0  N7   C2   SING  N  N   7  
GN0  C2   C1   DOUB  Y  N   8  
GN0  C2   C3   SING  Y  N   9  
GN0  C1   C6   SING  Y  N  10  
GN0  C3   C4   DOUB  Y  N  11  
GN0  C6   C5   DOUB  Y  N  12  
GN0  C4   C5   SING  Y  N  13  
GN0  C5   C8   SING  N  N  14  
GN0  C18  C8   SING  N  N  15  
GN0  C18  C17  SING  N  N  16  
GN0  C8   N14  SING  N  N  17  
GN0  C8   C9   SING  N  N  18  
GN0  O19  C17  SING  N  N  19  
GN0  C17  C16  DOUB  N  N  20  
GN0  N14  C15  SING  N  N  21  
GN0  C9   C10  DOUB  Y  N  22  
GN0  C9   C13  SING  Y  N  23  
GN0  C10  S11  SING  Y  N  24  
GN0  C16  C15  SING  N  N  25  
GN0  C16  S21  SING  N  N  26  
GN0  C15  O20  DOUB  N  N  27  
GN0  C13  C12  DOUB  Y  N  28  
GN0  S11  C12  SING  Y  N  29  
GN0  S21  C22  SING  N  N  30  
GN0  C23  C22  DOUB  Y  N  31  
GN0  C23  C24  SING  Y  N  32  
GN0  C22  C27  SING  Y  N  33  
GN0  C24  C25  DOUB  Y  N  34  
GN0  C27  CL   SING  N  N  35  
GN0  C27  C26  DOUB  Y  N  36  
GN0  C25  C26  SING  Y  N  37  
GN0  C4   H1   SING  N  N  38  
GN0  C6   H2   SING  N  N  39  
GN0  C10  H3   SING  N  N  40  
GN0  C12  H4   SING  N  N  41  
GN0  C13  H5   SING  N  N  42  
GN0  C3   H6   SING  N  N  43  
GN0  C1   H7   SING  N  N  44  
GN0  N14  H8   SING  N  N  45  
GN0  C18  H10  SING  N  N  46  
GN0  C18  H11  SING  N  N  47  
GN0  C23  H12  SING  N  N  48  
GN0  C24  H13  SING  N  N  49  
GN0  C25  H14  SING  N  N  50  
GN0  C26  H15  SING  N  N  51  
GN0  C29  H16  SING  N  N  52  
GN0  C29  H17  SING  N  N  53  
GN0  C30  H18  SING  N  N  54  
GN0  C30  H19  SING  N  N  55  
GN0  C32  H20  SING  N  N  56  
GN0  C32  H21  SING  N  N  57  
GN0  C33  H22  SING  N  N  58  
GN0  C33  H23  SING  N  N  59  
GN0  O19  H9   SING  N  N  60  
#   #
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
GN0  InChI             InChI                 1.03   "InChI=1S/C25H23ClN2O3S2/c26-20-3-1-2-4-22(20)33-23-21(29)15-25(27-24(23)30,18-9-14-32-16-18)17-5-7-19(8-6-17)28-10-12-31-13-11-28/h1-9,14,16,29H,10-13,15H2,(H,27,30)/t25-/m1/s1"  
GN0  InChIKey          InChI                 1.03   SUFXXEIVBZJOAP-RUZDIDTESA-N  
GN0  SMILES_CANONICAL  CACTVS                3.385  "OC1=C(Sc2ccccc2Cl)C(=O)N[C@@](C1)(c3cscc3)c4ccc(cc4)N5CCOCC5"  
GN0  SMILES            CACTVS                3.385  "OC1=C(Sc2ccccc2Cl)C(=O)N[C](C1)(c3cscc3)c4ccc(cc4)N5CCOCC5"  
GN0  SMILES_CANONICAL  "OpenEye OEToolkits"  2.0.4  "c1ccc(c(c1)SC2=C(C[C@@](NC2=O)(c3ccc(cc3)N4CCOCC4)c5ccsc5)O)Cl"  
GN0  SMILES            "OpenEye OEToolkits"  2.0.4  "c1ccc(c(c1)SC2=C(CC(NC2=O)(c3ccc(cc3)N4CCOCC4)c5ccsc5)O)Cl"  
#
_pdbx_chem_comp_identifier.comp_id          GN0
_pdbx_chem_comp_identifier.type             "SYSTEMATIC NAME"
_pdbx_chem_comp_identifier.program          "OpenEye OEToolkits"
_pdbx_chem_comp_identifier.program_version  2.0.4
_pdbx_chem_comp_identifier.identifier       "(2~{R})-5-(2-chlorophenyl)sulfanyl-2-(4-morpholin-4-ylphenyl)-4-oxidanyl-2-thiophen-3-yl-1,3-dihydropyridin-6-one"
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
GN0  "Create component"    2015-05-19  RCSB  
GN0  "Other modification"  2015-10-27  RCSB  
GN0  "Initial release"     2016-05-18  RCSB  
GN0  "Modify synonyms"     2021-03-01  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     GN0
_pdbx_chem_comp_synonyms.name        "inhibitor GNE-140"
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
