data_QH4
#

_chem_comp.id                                   QH4
_chem_comp.name                                 "{(2S)-4-[2-{[(2S)-1-methylpyrrolidin-2-yl]methoxy}-7-(naphthalen-1-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl]-1-propanoylpiperazin-2-yl}acetonitrile"
_chem_comp.type                                 non-polymer
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C32 H39 N7 O2"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        ?
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2019-11-01
_chem_comp.pdbx_modified_date                   2020-04-17
_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                       553.698
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    QH4
_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       6USZ
_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
QH4  C18  C1   C  0  1  N  N  N  24.638   1.379  -20.293   4.293  -2.680   1.888  C18  QH4   1  
QH4  N5   N1   N  0  1  Y  N  N  24.615   4.363  -22.595   1.209   1.227  -0.058  N5   QH4   2  
QH4  C14  C2   C  0  1  N  N  N  26.959   0.987  -22.824   3.900  -1.667  -1.780  C14  QH4   3  
QH4  C13  C3   C  0  1  N  N  N  26.192   2.300  -22.993   2.912  -0.528  -1.508  C13  QH4   4  
QH4  C17  C4   C  0  1  N  N  N  24.104   0.815  -22.627   2.544  -1.284   0.767  C17  QH4   5  
QH4  C16  C5   C  0  1  N  N  S  24.893   0.329  -21.390   3.517  -2.454   0.589  C16  QH4   6  
QH4  N3   N2   N  0  1  Y  N  N  22.584   5.607  -22.856  -1.024   1.817  -0.077  N3   QH4   7  
QH4  C10  C6   C  0  1  N  N  N  20.473   4.665  -23.671  -2.857   0.277  -0.574  C10  QH4   8  
QH4  C8   C7   C  0  1  N  N  N  20.820   2.572  -24.939  -2.203  -1.875  -1.444  C8   QH4   9  
QH4  C22  C8   C  0  1  N  N  N  26.017  10.378  -21.564   0.793   7.768   0.003  C22  QH4  10  
QH4  C7   C9   C  0  1  N  N  N  21.883   2.063  -23.959  -0.773  -1.807  -0.904  C7   QH4  11  
QH4  C6   C10  C  0  1  Y  N  N  23.954   3.266  -23.048   0.912  -0.030  -0.373  C6   QH4  12  
QH4  C1   C11  C  0  1  Y  N  N  22.596   3.313  -23.406  -0.428  -0.386  -0.551  C1   QH4  13  
QH4  C4   C12  C  0  1  Y  N  N  23.896   5.502  -22.542   0.250   2.127   0.086  C4   QH4  14  
QH4  C19  C13  C  0  1  N  N  N  25.866   6.700  -21.899  -0.488   4.334   0.553  C19  QH4  15  
QH4  C20  C14  C  0  1  N  N  S  26.241   8.012  -21.171   0.079   5.708   0.917  C20  QH4  16  
QH4  C2   C15  C  0  1  Y  N  N  21.937   4.539  -23.293  -1.394   0.580  -0.395  C2   QH4  17  
QH4  N9   N3   N  0  1  N  N  N  19.930   3.355  -24.034  -3.092  -1.169  -0.508  N9   QH4  18  
QH4  O11  O1   O  0  1  N  N  N  24.504   6.658  -22.128   0.584   3.399   0.409  O11  QH4  19  
QH4  N12  N4   N  0  1  N  N  N  24.705   2.028  -23.187   1.916  -0.973  -0.524  N12  QH4  20  
QH4  N15  N5   N  0  1  N  N  N  26.385   0.229  -21.628   4.455  -2.121  -0.495  N15  QH4  21  
QH4  N21  N6   N  0  1  N  N  N  26.376   9.070  -22.285   0.779   6.311  -0.246  N21  QH4  22  
QH4  C23  C16  C  0  1  N  N  N  24.814   9.951  -20.684  -0.400   8.081   0.925  C23  QH4  23  
QH4  C24  C17  C  0  1  N  N  N  25.107   8.517  -20.275  -1.065   6.713   1.202  C24  QH4  24  
QH4  C25  C18  C  0  1  N  N  N  27.839   9.130  -22.777   2.145   5.784  -0.370  C25  QH4  25  
QH4  C26  C19  C  0  1  Y  N  N  18.536   3.479  -24.469  -4.427  -1.470  -0.764  C26  QH4  26  
QH4  C27  C20  C  0  1  Y  N  N  18.175   3.549  -25.823  -4.981  -1.185  -1.994  C27  QH4  27  
QH4  C28  C21  C  0  1  Y  N  N  16.804   3.672  -26.178  -6.315  -1.482  -2.260  C28  QH4  28  
QH4  C29  C22  C  0  1  Y  N  N  15.781   3.725  -25.213  -7.108  -2.061  -1.317  C29  QH4  29  
QH4  C30  C23  C  0  1  Y  N  N  16.153   3.649  -23.847  -6.582  -2.368  -0.051  C30  QH4  30  
QH4  C31  C24  C  0  1  Y  N  N  17.524   3.535  -23.489  -5.225  -2.076   0.231  C31  QH4  31  
QH4  C32  C25  C  0  1  Y  N  N  15.174   3.700  -22.834  -7.377  -2.967   0.942  C32  QH4  32  
QH4  C33  C26  C  0  1  Y  N  N  15.544   3.636  -21.465  -6.836  -3.252   2.158  C33  QH4  33  
QH4  C34  C27  C  0  1  Y  N  N  16.892   3.510  -21.145  -5.502  -2.959   2.435  C34  QH4  34  
QH4  C35  C28  C  0  1  Y  N  N  17.888   3.467  -22.146  -4.699  -2.389   1.494  C35  QH4  35  
QH4  C36  C29  C  0  1  N  N  N  27.155  -0.592  -20.822   5.786  -2.230  -0.316  C36  QH4  36  
QH4  O37  O2   O  0  1  N  N  N  26.726  -0.957  -19.699   6.223  -2.689   0.718  O37  QH4  37  
QH4  C38  C30  C  0  1  N  N  N  28.621  -0.882  -21.305   6.731  -1.780  -1.400  C38  QH4  38  
QH4  C39  C31  C  0  1  N  N  N  29.716  -0.607  -20.219   8.174  -2.010  -0.946  C39  QH4  39  
QH4  C40  C32  C  0  1  N  N  N  23.232   1.202  -19.747   4.902  -4.020   1.869  C40  QH4  40  
QH4  N41  N7   N  0  1  N  N  N  22.147   1.202  -19.331   5.372  -5.054   1.855  N41  QH4  41  
QH4  H1   H1   H  0  1  N  N  N  25.367   1.246  -19.480   5.076  -1.926   1.980  H1   QH4  42  
QH4  H2   H2   H  0  1  N  N  N  24.743   2.388  -20.718   3.613  -2.602   2.736  H2   QH4  43  
QH4  H3   H3   H  0  1  N  N  N  26.852   0.377  -23.733   3.382  -2.493  -2.267  H3   QH4  44  
QH4  H4   H4   H  0  1  N  N  N  28.024   1.201  -22.649   4.707  -1.311  -2.421  H4   QH4  45  
QH4  H5   H5   H  0  1  N  N  N  26.580   2.835  -23.872   3.451   0.335  -1.116  H5   QH4  46  
QH4  H6   H6   H  0  1  N  N  N  26.333   2.920  -22.095   2.410  -0.253  -2.436  H6   QH4  47  
QH4  H7   H7   H  0  1  N  N  N  23.067   1.031  -22.331   1.775  -1.557   1.489  H7   QH4  48  
QH4  H8   H8   H  0  1  N  N  N  24.110   0.024  -23.392   3.088  -0.410   1.127  H8   QH4  49  
QH4  H9   H9   H  0  1  N  N  N  24.500  -0.646  -21.065   2.962  -3.356   0.332  H9   QH4  50  
QH4  H10  H10  H  0  1  N  N  N  20.376   5.348  -24.528  -3.426   0.771   0.214  H10  QH4  51  
QH4  H11  H11  H  0  1  N  N  N  19.910   5.067  -22.816  -3.186   0.650  -1.544  H11  QH4  52  
QH4  H12  H12  H  0  1  N  N  N  20.279   1.740  -25.413  -2.247  -1.397  -2.423  H12  QH4  53  
QH4  H13  H13  H  0  1  N  N  N  21.264   3.211  -25.717  -2.513  -2.917  -1.529  H13  QH4  54  
QH4  H14  H14  H  0  1  N  N  N  26.855  10.736  -20.947   1.725   8.052   0.493  H14  QH4  55  
QH4  H15  H15  H  0  1  N  N  N  25.728  11.161  -22.280   0.688   8.310  -0.937  H15  QH4  56  
QH4  H16  H16  H  0  1  N  N  N  21.409   1.502  -23.140  -0.692  -2.431  -0.014  H16  QH4  57  
QH4  H17  H17  H  0  1  N  N  N  22.602   1.414  -24.480  -0.081  -2.170  -1.664  H17  QH4  58  
QH4  H18  H18  H  0  1  N  N  N  26.157   5.842  -21.276  -1.160   3.997   1.343  H18  QH4  59  
QH4  H19  H19  H  0  1  N  N  N  26.398   6.652  -22.860  -1.037   4.404  -0.386  H19  QH4  60  
QH4  H20  H20  H  0  1  N  N  N  27.180   7.902  -20.609   0.748   5.632   1.774  H20  QH4  61  
QH4  H22  H22  H  0  1  N  N  N  24.737  10.597  -19.797  -0.052   8.528   1.856  H22  QH4  62  
QH4  H23  H23  H  0  1  N  N  N  23.878  10.004  -21.259  -1.102   8.747   0.423  H23  QH4  63  
QH4  H24  H24  H  0  1  N  N  N  24.211   7.895  -20.415  -1.903   6.547   0.525  H24  QH4  64  
QH4  H25  H25  H  0  1  N  N  N  25.416   8.482  -19.220  -1.388   6.645   2.241  H25  QH4  65  
QH4  H26  H26  H  0  1  N  N  N  28.092   8.192  -23.293   2.692   5.973   0.553  H26  QH4  66  
QH4  H27  H27  H  0  1  N  N  N  27.957   9.974  -23.473   2.105   4.711  -0.555  H27  QH4  67  
QH4  H28  H28  H  0  1  N  N  N  28.510   9.267  -21.916   2.651   6.278  -1.200  H28  QH4  68  
QH4  H29  H29  H  0  1  N  N  N  18.934   3.510  -26.591  -4.374  -0.725  -2.760  H29  QH4  69  
QH4  H30  H30  H  0  1  N  N  N  16.539   3.727  -27.223  -6.727  -1.249  -3.231  H30  QH4  70  
QH4  H31  H31  H  0  1  N  N  N  14.745   3.821  -25.504  -8.141  -2.283  -1.542  H31  QH4  71  
QH4  H32  H32  H  0  1  N  N  N  14.132   3.789  -23.102  -8.413  -3.199   0.742  H32  QH4  72  
QH4  H33  H33  H  0  1  N  N  N  14.795   3.684  -20.688  -7.449  -3.711   2.919  H33  QH4  73  
QH4  H34  H34  H  0  1  N  N  N  17.184   3.444  -20.107  -5.096  -3.195   3.408  H34  QH4  74  
QH4  H35  H35  H  0  1  N  N  N  18.929   3.382  -21.871  -3.667  -2.168   1.723  H35  QH4  75  
QH4  H36  H36  H  0  1  N  N  N  28.685  -1.940  -21.601   6.541  -2.351  -2.308  H36  QH4  76  
QH4  H37  H37  H  0  1  N  N  N  28.830  -0.244  -22.177   6.578  -0.719  -1.598  H37  QH4  77  
QH4  H38  H38  H  0  1  N  N  N  30.709  -0.833  -20.634   8.858  -1.684  -1.730  H38  QH4  78  
QH4  H39  H39  H  0  1  N  N  N  29.676   0.450  -19.918   8.365  -1.439  -0.037  H39  QH4  79  
QH4  H40  H40  H  0  1  N  N  N  29.531  -1.245  -19.342   8.328  -3.071  -0.747  H40  QH4  80  
#   #
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
QH4  C28  C27  DOUB  Y  N   1  
QH4  C28  C29  SING  Y  N   2  
QH4  C27  C26  SING  Y  N   3  
QH4  C29  C30  DOUB  Y  N   4  
QH4  C8   N9   SING  N  N   5  
QH4  C8   C7   SING  N  N   6  
QH4  C26  N9   SING  N  N   7  
QH4  C26  C31  DOUB  Y  N   8  
QH4  N9   C10  SING  N  N   9  
QH4  C7   C1   SING  N  N  10  
QH4  C30  C31  SING  Y  N  11  
QH4  C30  C32  SING  Y  N  12  
QH4  C10  C2   SING  N  N  13  
QH4  C31  C35  SING  Y  N  14  
QH4  C1   C2   DOUB  Y  N  15  
QH4  C1   C6   SING  Y  N  16  
QH4  C2   N3   SING  Y  N  17  
QH4  N12  C6   SING  N  N  18  
QH4  N12  C13  SING  N  N  19  
QH4  N12  C17  SING  N  N  20  
QH4  C6   N5   DOUB  Y  N  21  
QH4  C13  C14  SING  N  N  22  
QH4  N3   C4   DOUB  Y  N  23  
QH4  C32  C33  DOUB  Y  N  24  
QH4  C14  N15  SING  N  N  25  
QH4  C25  N21  SING  N  N  26  
QH4  C17  C16  SING  N  N  27  
QH4  N5   C4   SING  Y  N  28  
QH4  C4   O11  SING  N  N  29  
QH4  N21  C22  SING  N  N  30  
QH4  N21  C20  SING  N  N  31  
QH4  C35  C34  DOUB  Y  N  32  
QH4  O11  C19  SING  N  N  33  
QH4  C19  C20  SING  N  N  34  
QH4  N15  C16  SING  N  N  35  
QH4  N15  C36  SING  N  N  36  
QH4  C22  C23  SING  N  N  37  
QH4  C33  C34  SING  Y  N  38  
QH4  C16  C18  SING  N  N  39  
QH4  C38  C36  SING  N  N  40  
QH4  C38  C39  SING  N  N  41  
QH4  C20  C24  SING  N  N  42  
QH4  C36  O37  DOUB  N  N  43  
QH4  C23  C24  SING  N  N  44  
QH4  C18  C40  SING  N  N  45  
QH4  C40  N41  TRIP  N  N  46  
QH4  C18  H1   SING  N  N  47  
QH4  C18  H2   SING  N  N  48  
QH4  C14  H3   SING  N  N  49  
QH4  C14  H4   SING  N  N  50  
QH4  C13  H5   SING  N  N  51  
QH4  C13  H6   SING  N  N  52  
QH4  C17  H7   SING  N  N  53  
QH4  C17  H8   SING  N  N  54  
QH4  C16  H9   SING  N  N  55  
QH4  C10  H10  SING  N  N  56  
QH4  C10  H11  SING  N  N  57  
QH4  C8   H12  SING  N  N  58  
QH4  C8   H13  SING  N  N  59  
QH4  C22  H14  SING  N  N  60  
QH4  C22  H15  SING  N  N  61  
QH4  C7   H16  SING  N  N  62  
QH4  C7   H17  SING  N  N  63  
QH4  C19  H18  SING  N  N  64  
QH4  C19  H19  SING  N  N  65  
QH4  C20  H20  SING  N  N  66  
QH4  C23  H22  SING  N  N  67  
QH4  C23  H23  SING  N  N  68  
QH4  C24  H24  SING  N  N  69  
QH4  C24  H25  SING  N  N  70  
QH4  C25  H26  SING  N  N  71  
QH4  C25  H27  SING  N  N  72  
QH4  C25  H28  SING  N  N  73  
QH4  C27  H29  SING  N  N  74  
QH4  C28  H30  SING  N  N  75  
QH4  C29  H31  SING  N  N  76  
QH4  C32  H32  SING  N  N  77  
QH4  C33  H33  SING  N  N  78  
QH4  C34  H34  SING  N  N  79  
QH4  C35  H35  SING  N  N  80  
QH4  C38  H36  SING  N  N  81  
QH4  C38  H37  SING  N  N  82  
QH4  C39  H38  SING  N  N  83  
QH4  C39  H39  SING  N  N  84  
QH4  C39  H40  SING  N  N  85  
#   #
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
QH4  SMILES            ACDLabs               12.01  "C(C#N)C1CN(CCN1C(=O)CC)c2nc(nc3CN(CCc23)c4c5c(ccc4)cccc5)OCC6CCCN6C"  
QH4  InChI             InChI                 1.03   "InChI=1S/C32H39N7O2/c1-3-30(40)39-19-18-38(20-24(39)13-15-33)31-27-14-17-37(29-12-6-9-23-8-4-5-11-26(23)29)21-28(27)34-32(35-31)41-22-25-10-7-16-36(25)2/h4-6,8-9,11-12,24-25H,3,7,10,13-14,16-22H2,1-2H3/t24-,25-/m0/s1"  
QH4  InChIKey          InChI                 1.03   CRZFLRFKRKGUET-DQEYMECFSA-N  
QH4  SMILES_CANONICAL  CACTVS                3.385  "CCC(=O)N1CCN(C[C@@H]1CC#N)c2nc(OC[C@@H]3CCCN3C)nc4CN(CCc24)c5cccc6ccccc56"  
QH4  SMILES            CACTVS                3.385  "CCC(=O)N1CCN(C[CH]1CC#N)c2nc(OC[CH]3CCCN3C)nc4CN(CCc24)c5cccc6ccccc56"  
QH4  SMILES_CANONICAL  "OpenEye OEToolkits"  2.0.7  "CCC(=O)N1CCN(C[C@@H]1CC#N)c2c3c(nc(n2)OC[C@@H]4CCCN4C)CN(CC3)c5cccc6c5cccc6"  
QH4  SMILES            "OpenEye OEToolkits"  2.0.7  "CCC(=O)N1CCN(CC1CC#N)c2c3c(nc(n2)OCC4CCCN4C)CN(CC3)c5cccc6c5cccc6"  
#   #
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
QH4  "SYSTEMATIC NAME"  ACDLabs               12.01  "{(2S)-4-[2-{[(2S)-1-methylpyrrolidin-2-yl]methoxy}-7-(naphthalen-1-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl]-1-propanoylpiperazin-2-yl}acetonitrile"  
QH4  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  2.0.7  "2-[(2~{S})-4-[2-[[(2~{S})-1-methylpyrrolidin-2-yl]methoxy]-7-naphthalen-1-yl-6,8-dihydro-5~{H}-pyrido[3,4-d]pyrimidin-4-yl]-1-propanoyl-piperazin-2-yl]ethanenitrile"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
QH4  "Create component"  2019-11-01  RCSB  
QH4  "Initial release"   2020-04-22  RCSB  
##
