data_EA9
#

_chem_comp.id                                   EA9
_chem_comp.name                                 "(4R)-3-(2-hydroxyphenyl)-4-(3-methoxy-4-propoxy-phenyl)-5-(pyridin-3-ylmethyl)-1,4-dihydropyrrolo[3,4-c]pyrazol-6-one"
_chem_comp.type                                 non-polymer
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C27 H26 N4 O4"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        ?
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2019-12-03
_chem_comp.pdbx_modified_date                   2021-05-21
_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                       470.520
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    EA9
_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       6LE7
_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
EA9  C1   C1   C  0  1  N  N  N   -7.909   7.573  -2.268   6.285  -4.232   2.042  C1   EA9   1  
EA9  C2   C2   C  0  1  N  N  N   -8.718   6.627  -1.398   5.742  -3.629   0.744  C2   EA9   2  
EA9  C3   C3   C  0  1  N  N  N   -9.832   7.368  -0.727   4.381  -2.985   1.012  C3   EA9   3  
EA9  O4   O1   O  0  1  N  N  N  -10.845   6.521  -0.408   3.874  -2.422  -0.200  O4   EA9   4  
EA9  C5   C4   C  0  1  Y  N  N  -12.084   6.804  -0.948   2.663  -1.806  -0.135  C5   EA9   5  
EA9  C6   C5   C  0  1  Y  N  N  -13.065   5.828  -0.977   1.978  -1.746   1.068  C6   EA9   6  
EA9  C7   C6   C  0  1  Y  N  N  -14.324   6.095  -1.519   0.747  -1.120   1.131  C7   EA9   7  
EA9  C8   C7   C  0  1  Y  N  N  -14.628   7.335  -2.029   0.197  -0.553  -0.003  C8   EA9   8  
EA9  C9   C8   C  0  1  N  N  R  -15.912   7.894  -2.678  -1.148   0.123   0.071  C9   EA9   9  
EA9  C10  C9   C  0  1  Y  N  N  -17.003   6.820  -2.968  -1.022   1.452   0.764  C10  EA9  10  
EA9  C11  C10  C  0  1  Y  N  N  -17.883   5.835  -2.425  -0.449   2.728   0.773  C11  EA9  11  
EA9  C12  C11  C  0  1  Y  N  N  -18.134   5.619  -1.063   0.493   3.275  -0.235  C12  EA9  12  
EA9  C13  C12  C  0  1  Y  N  N  -19.228   6.341  -0.655   0.227   3.126  -1.594  C13  EA9  13  
EA9  C14  C13  C  0  1  Y  N  N  -19.730   6.431   0.624   1.106   3.637  -2.528  C14  EA9  14  
EA9  C15  C14  C  0  1  Y  N  N  -19.079   5.694   1.560   2.251   4.297  -2.119  C15  EA9  15  
EA9  C16  C15  C  0  1  Y  N  N  -17.963   4.962   1.196   2.524   4.451  -0.773  C16  EA9  16  
EA9  C17  C16  C  0  1  Y  N  N  -17.471   4.908  -0.085   1.648   3.948   0.175  C17  EA9  17  
EA9  O18  O2   O  0  1  N  N  N  -16.326   4.110  -0.267   1.913   4.103   1.498  O18  EA9  18  
EA9  N19  N1   N  0  1  Y  N  N  -18.513   5.315  -3.454  -0.899   3.356   1.842  N19  EA9  19  
EA9  N20  N2   N  0  1  Y  N  N  -18.041   5.829  -4.598  -1.699   2.602   2.509  N20  EA9  20  
EA9  C21  C17  C  0  1  Y  N  N  -17.135   6.768  -4.305  -1.822   1.391   1.889  C21  EA9  21  
EA9  C22  C18  C  0  1  N  N  N  -16.178   7.824  -4.911  -2.456   0.069   1.939  C22  EA9  22  
EA9  O23  O3   O  0  1  N  N  N  -15.948   8.107  -5.956  -3.222  -0.301   2.808  O23  EA9  23  
EA9  N24  N3   N  0  1  N  N  N  -15.495   8.500  -3.921  -2.072  -0.676   0.886  N24  EA9  24  
EA9  C25  C19  C  0  1  N  N  N  -14.488   9.534  -4.235  -2.500  -2.048   0.603  C25  EA9  25  
EA9  C26  C20  C  0  1  Y  N  N  -14.689  10.814  -5.052  -3.745  -2.021  -0.246  C26  EA9  26  
EA9  C27  C21  C  0  1  Y  N  N  -15.051  10.761  -6.365  -4.998  -1.996   0.347  C27  EA9  27  
EA9  C28  C22  C  0  1  Y  N  N  -15.186  11.926  -7.016  -6.116  -1.966  -0.473  C28  EA9  28  
EA9  C29  C23  C  0  1  Y  N  N  -14.866  13.098  -6.336  -5.944  -1.962  -1.845  C29  EA9  29  
EA9  N30  N4   N  0  1  Y  N  N  -14.479  13.138  -5.092  -4.737  -1.987  -2.374  N30  EA9  30  
EA9  C31  C24  C  0  1  Y  N  N  -14.371  12.042  -4.443  -3.652  -2.015  -1.625  C31  EA9  31  
EA9  C32  C25  C  0  1  Y  N  N  -13.634   8.235  -1.914   0.875  -0.610  -1.207  C32  EA9  32  
EA9  C33  C26  C  0  1  Y  N  N  -12.413   8.037  -1.445   2.112  -1.231  -1.276  C33  EA9  33  
EA9  O34  O4   O  0  1  N  N  N  -11.663   9.158  -1.587   2.780  -1.288  -2.459  O34  EA9  34  
EA9  C35  C27  C  0  1  N  N  N  -11.498   9.369  -2.936   2.148  -0.687  -3.591  C35  EA9  35  
EA9  H1   H1   H  0  1  N  N  N   -7.094   7.017  -2.755   6.395  -3.447   2.789  H1   EA9  36  
EA9  H2   H2   H  0  1  N  N  N   -8.562   8.014  -3.035   5.591  -4.988   2.409  H2   EA9  37  
EA9  H3   H3   H  0  1  N  N  N   -7.485   8.373  -1.643   7.255  -4.691   1.851  H3   EA9  38  
EA9  H4   H4   H  0  1  N  N  N   -9.139   5.827  -2.025   6.436  -2.873   0.377  H4   EA9  39  
EA9  H5   H5   H  0  1  N  N  N   -8.062   6.186  -0.633   5.632  -4.415  -0.003  H5   EA9  40  
EA9  H6   H6   H  0  1  N  N  N   -9.451   7.839   0.191   3.687  -3.741   1.379  H6   EA9  41  
EA9  H7   H7   H  0  1  N  N  N  -10.211   8.145  -1.407   4.491  -2.199   1.759  H7   EA9  42  
EA9  H8   H8   H  0  1  N  N  N  -12.854   4.848  -0.575   2.405  -2.188   1.955  H8   EA9  43  
EA9  H9   H9   H  0  1  N  N  N  -15.071   5.315  -1.538   0.214  -1.073   2.070  H9   EA9  44  
EA9  H10  H10  H  0  1  N  N  N  -16.341   8.657  -2.012  -1.554   0.261  -0.932  H10  EA9  45  
EA9  H11  H11  H  0  1  N  N  N  -19.751   6.898  -1.419  -0.665   2.611  -1.916  H11  EA9  46  
EA9  H12  H12  H  0  1  N  N  N  -20.584   7.046   0.866   0.899   3.521  -3.582  H12  EA9  47  
EA9  H13  H13  H  0  1  N  N  N  -19.430   5.679   2.581   2.935   4.694  -2.855  H13  EA9  48  
EA9  H14  H14  H  0  1  N  N  N  -17.449   4.401   1.963   3.420   4.967  -0.460  H14  EA9  49  
EA9  H15  H15  H  0  1  N  N  N  -16.069   3.730   0.565   2.434   3.385   1.882  H15  EA9  50  
EA9  H17  H17  H  0  1  N  N  N  -13.683   8.993  -4.754  -1.708  -2.574   0.069  H17  EA9  51  
EA9  H18  H18  H  0  1  N  N  N  -14.126   9.880  -3.256  -2.711  -2.563   1.540  H18  EA9  52  
EA9  H19  H19  H  0  1  N  N  N  -15.222   9.818  -6.862  -5.102  -2.000   1.422  H19  EA9  53  
EA9  H20  H20  H  0  1  N  N  N  -15.533  11.954  -8.038  -7.107  -1.946  -0.046  H20  EA9  54  
EA9  H21  H21  H  0  1  N  N  N  -14.943  14.032  -6.873  -6.810  -1.938  -2.491  H21  EA9  55  
EA9  H22  H22  H  0  1  N  N  N  -14.032  12.059  -3.418  -2.679  -2.030  -2.094  H22  EA9  56  
EA9  H23  H23  H  0  1  N  N  N  -13.860   9.238  -2.244   0.443  -0.167  -2.092  H23  EA9  57  
EA9  H24  H24  H  0  1  N  N  N  -10.892  10.273  -3.095   2.786  -0.803  -4.467  H24  EA9  58  
EA9  H25  H25  H  0  1  N  N  N  -10.988   8.503  -3.383   1.189  -1.173  -3.773  H25  EA9  59  
EA9  H26  H26  H  0  1  N  N  N  -12.482   9.499  -3.410   1.987   0.374  -3.396  H26  EA9  60  
EA9  H16  H16  H  0  1  N  N  N  -18.320   5.556  -5.519  -2.148   2.856   3.330  H16  EA9  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
EA9  C28  C27  DOUB  Y  N   1  
EA9  C28  C29  SING  Y  N   2  
EA9  C27  C26  SING  Y  N   3  
EA9  C29  N30  DOUB  Y  N   4  
EA9  O23  C22  DOUB  N  N   5  
EA9  N30  C31  SING  Y  N   6  
EA9  C26  C31  DOUB  Y  N   7  
EA9  C26  C25  SING  N  N   8  
EA9  C22  C21  SING  N  N   9  
EA9  C22  N24  SING  N  N  10  
EA9  N20  C21  SING  Y  N  11  
EA9  N20  N19  SING  Y  N  12  
EA9  C21  C10  DOUB  Y  N  13  
EA9  C25  N24  SING  N  N  14  
EA9  N24  C9   SING  N  N  15  
EA9  N19  C11  DOUB  Y  N  16  
EA9  C10  C9   SING  N  N  17  
EA9  C10  C11  SING  Y  N  18  
EA9  C35  O34  SING  N  N  19  
EA9  C9   C8   SING  N  N  20  
EA9  C11  C12  SING  N  N  21  
EA9  C1   C2   SING  N  N  22  
EA9  C8   C32  DOUB  Y  N  23  
EA9  C8   C7   SING  Y  N  24  
EA9  C32  C33  SING  Y  N  25  
EA9  O34  C33  SING  N  N  26  
EA9  C7   C6   DOUB  Y  N  27  
EA9  C33  C5   DOUB  Y  N  28  
EA9  C2   C3   SING  N  N  29  
EA9  C12  C13  DOUB  Y  N  30  
EA9  C12  C17  SING  Y  N  31  
EA9  C6   C5   SING  Y  N  32  
EA9  C5   O4   SING  N  N  33  
EA9  C3   O4   SING  N  N  34  
EA9  C13  C14  SING  Y  N  35  
EA9  O18  C17  SING  N  N  36  
EA9  C17  C16  DOUB  Y  N  37  
EA9  C14  C15  DOUB  Y  N  38  
EA9  C16  C15  SING  Y  N  39  
EA9  C1   H1   SING  N  N  40  
EA9  C1   H2   SING  N  N  41  
EA9  C1   H3   SING  N  N  42  
EA9  C2   H4   SING  N  N  43  
EA9  C2   H5   SING  N  N  44  
EA9  C3   H6   SING  N  N  45  
EA9  C3   H7   SING  N  N  46  
EA9  C6   H8   SING  N  N  47  
EA9  C7   H9   SING  N  N  48  
EA9  C9   H10  SING  N  N  49  
EA9  C13  H11  SING  N  N  50  
EA9  C14  H12  SING  N  N  51  
EA9  C15  H13  SING  N  N  52  
EA9  C16  H14  SING  N  N  53  
EA9  O18  H15  SING  N  N  54  
EA9  C25  H17  SING  N  N  55  
EA9  C25  H18  SING  N  N  56  
EA9  C27  H19  SING  N  N  57  
EA9  C28  H20  SING  N  N  58  
EA9  C29  H21  SING  N  N  59  
EA9  C31  H22  SING  N  N  60  
EA9  C32  H23  SING  N  N  61  
EA9  C35  H24  SING  N  N  62  
EA9  C35  H25  SING  N  N  63  
EA9  C35  H26  SING  N  N  64  
EA9  N20  H16  SING  N  N  65  
#   #
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
EA9  InChI             InChI                 1.03   "InChI=1S/C27H26N4O4/c1-3-13-35-21-11-10-18(14-22(21)34-2)26-23-24(19-8-4-5-9-20(19)32)29-30-25(23)27(33)31(26)16-17-7-6-12-28-15-17/h4-12,14-15,26,32H,3,13,16H2,1-2H3,(H,29,30)/t26-/m1/s1"  
EA9  InChIKey          InChI                 1.03   VDJNZGXOMKRJML-AREMUKBSSA-N  
EA9  SMILES_CANONICAL  CACTVS                3.385  "CCCOc1ccc(cc1OC)[C@H]2N(Cc3cccnc3)C(=O)c4[nH]nc(c5ccccc5O)c24"  
EA9  SMILES            CACTVS                3.385  "CCCOc1ccc(cc1OC)[CH]2N(Cc3cccnc3)C(=O)c4[nH]nc(c5ccccc5O)c24"  
EA9  SMILES_CANONICAL  "OpenEye OEToolkits"  2.0.7  "CCCOc1ccc(cc1OC)[C@@H]2c3c(n[nH]c3C(=O)N2Cc4cccnc4)c5ccccc5O"  
EA9  SMILES            "OpenEye OEToolkits"  2.0.7  "CCCOc1ccc(cc1OC)C2c3c(n[nH]c3C(=O)N2Cc4cccnc4)c5ccccc5O"  
#
_pdbx_chem_comp_identifier.comp_id          EA9
_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       "(4~{R})-3-(2-hydroxyphenyl)-4-(3-methoxy-4-propoxy-phenyl)-5-(pyridin-3-ylmethyl)-1,4-dihydropyrrolo[3,4-c]pyrazol-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
EA9  "Create component"  2019-12-03  PDBJ  
EA9  "Initial release"   2021-05-26  RCSB  
##
