data_D89
#

_chem_comp.id                                   D89
_chem_comp.name                                 "6-[2-[2,4-bis(fluoranyl)phenoxy]-5-(ethylsulfonylmethyl)pyridin-3-yl]-8-methyl-4H-pyrrolo[1,2-a]pyrazin-1-one"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C22 H19 F2 N3 O4 S"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        ?
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2019-07-16
_chem_comp.pdbx_modified_date                   2020-07-03
_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                       459.466
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    D89
_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       6KEG
_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
D89  C10   C1   C  0  1  N  N  N  -11.683   -3.481  -2.253  -0.865   5.321  -1.262  C10   D89   1  
D89  C13   C2   C  0  1  Y  N  N   -7.535   -7.133  -1.361   1.289  -0.380  -1.054  C13   D89   2  
D89  C15   C3   C  0  1  Y  N  N   -6.144   -8.286   0.253  -0.067  -2.339  -0.872  C15   D89   3  
D89  C17   C4   C  0  1  Y  N  N   -8.177   -7.470   0.912  -1.048  -0.290  -0.466  C17   D89   4  
D89  C20   C5   C  0  1  N  N  N   -5.310   -8.007  -2.085   2.346  -2.612  -1.494  C20   D89   5  
D89  C22   C6   C  0  1  N  N  N   -6.146   -7.776  -4.964   4.592  -4.089  -0.649  C22   D89   6  
D89  C26   C7   C  0  1  Y  N  N   -7.268   -4.873   3.920  -5.423  -0.967  -0.923  C26   D89   7  
D89  C28   C8   C  0  1  Y  N  N   -8.544   -6.312   5.364  -4.817  -1.595   1.312  C28   D89   8  
D89  N1    N1   N  0  1  N  N  N  -13.623   -6.360   0.680   2.910   4.494   1.234  N1    D89   9  
D89  C2    C9   C  0  1  N  N  N  -12.806   -7.273   1.166   3.234   3.257   1.417  C2    D89  10  
D89  C3    C10  C  0  1  N  N  N  -11.475   -7.294   0.786   2.386   2.157   0.821  C3    D89  11  
D89  N4    N2   N  0  1  Y  N  N  -11.009   -6.373  -0.098   1.204   2.549   0.043  N4    D89  12  
D89  C5    C11  C  0  1  Y  N  N  -11.829   -5.487  -0.580   0.940   3.898  -0.096  C5    D89  13  
D89  C6    C12  C  0  1  N  N  N  -13.183   -5.467  -0.181   1.835   4.871   0.527  C6    D89  14  
D89  C7    C13  C  0  1  Y  N  N   -9.763   -6.217  -0.640   0.244   1.846  -0.617  C7    D89  15  
D89  C8    C14  C  0  1  Y  N  N   -9.808   -5.124  -1.498  -0.640   2.745  -1.183  C8    D89  16  
D89  C9    C15  C  0  1  Y  N  N  -11.119   -4.660  -1.479  -0.206   4.028  -0.857  C9    D89  17  
D89  O11   O1   O  0  1  N  N  N  -13.915   -4.652  -0.632   1.597   6.059   0.401  O11   D89  18  
D89  C12   C16  C  0  1  Y  N  N   -8.471   -6.985  -0.359   0.162   0.376  -0.714  C12   D89  19  
D89  C14   C17  C  0  1  Y  N  N   -6.371   -7.808  -1.030   1.160  -1.756  -1.131  C14   D89  20  
D89  N16   N3   N  0  1  Y  N  N   -7.054   -8.110   1.193  -1.117  -1.607  -0.553  N16   D89  21  
D89  O18   O2   O  0  1  N  N  N   -9.126   -7.291   1.911  -2.153   0.422  -0.135  O18   D89  22  
D89  C19   C18  C  0  1  Y  N  N   -8.618   -6.595   2.988  -3.329  -0.248  -0.003  C19   D89  23  
D89  S21   S1   S  0  1  N  N  N   -6.002   -8.876  -3.535   3.234  -3.086   0.015  S21   D89  24  
D89  O23   O3   O  0  1  N  N  N   -7.322   -9.467  -3.301   3.782  -1.915   0.605  O23   D89  25  
D89  O24   O4   O  0  1  N  N  N   -5.212  -10.082  -3.789   2.390  -3.925   0.792  O24   D89  26  
D89  C25   C19  C  0  1  Y  N  N   -7.748   -5.540   2.805  -4.230  -0.281  -1.056  C25   D89  27  
D89  C27   C20  C  0  1  Y  N  N   -7.668   -5.266   5.195  -5.718  -1.622   0.260  C27   D89  28  
D89  C29   C21  C  0  1  Y  N  N   -9.011   -6.977   4.253  -3.621  -0.915   1.180  C29   D89  29  
D89  F30   F1   F  0  1  N  N  N   -9.871   -8.013   4.411  -2.737  -0.897   2.202  F30   D89  30  
D89  F31   F2   F  0  1  N  N  N   -7.214   -4.623   6.309  -6.887  -2.287   0.389  F31   D89  31  
D89  C32   C22  C  0  1  N  N  N   -6.863   -6.483  -4.552   5.467  -4.588   0.503  C32   D89  32  
D89  H102  H1   H  0  0  N  N  N  -12.063   -3.828  -3.225  -1.595   5.609  -0.505  H102  D89  33  
D89  H103  H2   H  0  0  N  N  N  -12.504   -3.026  -1.680  -0.110   6.101  -1.353  H103  D89  34  
D89  H101  H3   H  0  0  N  N  N  -10.891   -2.735  -2.414  -1.368   5.188  -2.219  H101  D89  35  
D89  H131  H4   H  0  0  N  N  N   -7.701   -6.742  -2.354   2.236   0.099  -1.256  H131  D89  36  
D89  H151  H5   H  0  0  N  N  N   -5.223   -8.802   0.482  -0.168  -3.412  -0.933  H151  D89  37  
D89  H202  H6   H  0  0  N  N  N   -4.488   -8.605  -1.663   2.003  -3.508  -2.011  H202  D89  38  
D89  H201  H7   H  0  0  N  N  N   -4.925   -7.026  -2.401   3.014  -2.049  -2.146  H201  D89  39  
D89  H222  H8   H  0  0  N  N  N   -6.723   -8.278  -5.755   4.183  -4.942  -1.190  H222  D89  40  
D89  H221  H9   H  0  0  N  N  N   -5.142   -7.533  -5.341   5.194  -3.483  -1.326  H221  D89  41  
D89  H261  H10  H  0  0  N  N  N   -6.583   -4.047   3.801  -6.126  -0.989  -1.742  H261  D89  42  
D89  H281  H11  H  0  0  N  N  N   -8.861   -6.607   6.353  -5.049  -2.106   2.234  H281  D89  43  
D89  H021  H12  H  0  0  N  N  N  -13.177   -8.009   1.864   4.111   3.009   1.995  H021  D89  44  
D89  H031  H13  H  0  0  N  N  N  -11.286   -8.283   0.344   3.027   1.557   0.174  H031  D89  45  
D89  H1    H14  H  0  1  N  N  N  -10.880   -7.183   1.705   2.050   1.516   1.636  H1    D89  46  
D89  H081  H15  H  0  0  N  N  N   -8.986   -4.715  -2.067  -1.511   2.498  -1.770  H081  D89  47  
D89  H251  H16  H  0  0  N  N  N   -7.447   -5.240   1.812  -4.000   0.229  -1.980  H251  D89  48  
D89  H321  H17  H  0  0  N  N  N   -6.949   -5.817  -5.423   5.876  -3.735   1.044  H321  D89  49  
D89  H323  H18  H  0  0  N  N  N   -7.868   -6.725  -4.176   4.866  -5.194   1.180  H323  D89  50  
D89  H322  H19  H  0  0  N  N  N   -6.287   -5.980  -3.761   6.283  -5.191   0.104  H322  D89  51  
#   #
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
D89  C22  C32   SING  N  N   1  
D89  C22  S21   SING  N  N   2  
D89  O24  S21   DOUB  N  N   3  
D89  S21  O23   DOUB  N  N   4  
D89  S21  C20   SING  N  N   5  
D89  C10  C9    SING  N  N   6  
D89  C20  C14   SING  N  N   7  
D89  C8   C9    SING  Y  N   8  
D89  C8   C7    DOUB  Y  N   9  
D89  C9   C5    DOUB  Y  N  10  
D89  C13  C14   DOUB  Y  N  11  
D89  C13  C12   SING  Y  N  12  
D89  C14  C15   SING  Y  N  13  
D89  C7   C12   SING  N  N  14  
D89  C7   N4    SING  Y  N  15  
D89  O11  C6    DOUB  N  N  16  
D89  C5   C6    SING  N  N  17  
D89  C5   N4    SING  Y  N  18  
D89  C12  C17   DOUB  Y  N  19  
D89  C6   N1    SING  N  N  20  
D89  N4   C3    SING  N  N  21  
D89  C15  N16   DOUB  Y  N  22  
D89  N1   C2    DOUB  N  N  23  
D89  C3   C2    SING  N  N  24  
D89  C17  N16   SING  Y  N  25  
D89  C17  O18   SING  N  N  26  
D89  O18  C19   SING  N  N  27  
D89  C25  C19   DOUB  Y  N  28  
D89  C25  C26   SING  Y  N  29  
D89  C19  C29   SING  Y  N  30  
D89  C26  C27   DOUB  Y  N  31  
D89  C29  F30   SING  N  N  32  
D89  C29  C28   DOUB  Y  N  33  
D89  C27  C28   SING  Y  N  34  
D89  C27  F31   SING  N  N  35  
D89  C10  H102  SING  N  N  36  
D89  C10  H103  SING  N  N  37  
D89  C10  H101  SING  N  N  38  
D89  C13  H131  SING  N  N  39  
D89  C15  H151  SING  N  N  40  
D89  C20  H202  SING  N  N  41  
D89  C20  H201  SING  N  N  42  
D89  C22  H222  SING  N  N  43  
D89  C22  H221  SING  N  N  44  
D89  C26  H261  SING  N  N  45  
D89  C28  H281  SING  N  N  46  
D89  C2   H021  SING  N  N  47  
D89  C3   H031  SING  N  N  48  
D89  C3   H1    SING  N  N  49  
D89  C8   H081  SING  N  N  50  
D89  C25  H251  SING  N  N  51  
D89  C32  H321  SING  N  N  52  
D89  C32  H323  SING  N  N  53  
D89  C32  H322  SING  N  N  54  
#   #
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
D89  InChI             InChI                 1.03   "InChI=1S/C22H19F2N3O4S/c1-3-32(29,30)12-14-9-16(18-8-13(2)20-21(28)25-6-7-27(18)20)22(26-11-14)31-19-5-4-15(23)10-17(19)24/h4-6,8-11H,3,7,12H2,1-2H3"  
D89  InChIKey          InChI                 1.03   HEFLLXAQDOXBPR-UHFFFAOYSA-N  
D89  SMILES_CANONICAL  CACTVS                3.385  "CC[S](=O)(=O)Cc1cnc(Oc2ccc(F)cc2F)c(c1)c3cc(C)c4n3CC=NC4=O"  
D89  SMILES            CACTVS                3.385  "CC[S](=O)(=O)Cc1cnc(Oc2ccc(F)cc2F)c(c1)c3cc(C)c4n3CC=NC4=O"  
D89  SMILES_CANONICAL  "OpenEye OEToolkits"  2.0.7  "CCS(=O)(=O)Cc1cc(c(nc1)Oc2ccc(cc2F)F)c3cc(c4n3CC=NC4=O)C"  
D89  SMILES            "OpenEye OEToolkits"  2.0.7  "CCS(=O)(=O)Cc1cc(c(nc1)Oc2ccc(cc2F)F)c3cc(c4n3CC=NC4=O)C"  
#
_pdbx_chem_comp_identifier.comp_id          D89
_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       "6-[2-[2,4-bis(fluoranyl)phenoxy]-5-(ethylsulfonylmethyl)pyridin-3-yl]-8-methyl-4~{H}-pyrrolo[1,2-a]pyrazin-1-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
D89  "Create component"  2019-07-16  PDBJ  
D89  "Initial release"   2020-07-08  RCSB  
##
