data_N14
#

_chem_comp.id                                   N14
_chem_comp.name                                 "5-fluoro-N-[5-(4-methylpiperazin-1-yl)pyridin-2-yl]-4-[(4S)-4-methyl-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a]azepin-3-yl]pyrimidin-2-amine"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C23 H29 F N8"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        ?
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2019-04-29
_chem_comp.pdbx_modified_date                   2020-07-24
_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                       436.528
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    N14
_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       6OQI
_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
N14  C4   C1   C  0  1  N  N  N  14.644   -8.083   7.684  -6.306   2.884  -0.916  C4   N14   1  
N14  C14  C2   C  0  1  Y  N  N  12.825  -10.467  14.357  -0.721  -2.260  -0.518  C14  N14   2  
N14  C5   C3   C  0  1  N  N  N  15.906   -7.224   7.696  -6.976   2.177   0.262  C5   N14   3  
N14  C6   C4   C  0  1  N  N  N  15.983   -6.452   9.015  -7.290   0.728  -0.119  C6   N14   4  
N14  C8   C5   C  0  1  Y  N  N  14.497   -7.880  10.468  -4.860   0.124  -0.077  C8   N14   5  
N14  C9   C6   C  0  1  Y  N  N  14.671   -8.645  11.600  -4.115  -0.922   0.384  C9   N14   6  
N14  C10  C7   C  0  1  Y  N  N  16.036   -8.540  11.951  -5.000  -1.833   0.997  C10  N14   7  
N14  C12  C8   C  0  1  Y  N  N  13.651   -9.447  12.346  -2.646  -1.074   0.261  C12  N14   8  
N14  C13  C9   C  0  1  Y  N  N  13.794   -9.709  13.721  -2.099  -2.162  -0.430  C13  N14   9  
N14  C3   C10  C  0  1  N  N  N  13.470   -7.281   8.236  -5.439   1.903  -1.700  C3   N14  10  
N14  C1   C11  C  0  1  N  N  N  12.421   -6.536  10.367  -3.119   0.975  -1.625  C1   N14  11  
N14  C16  C12  C  0  1  Y  N  N  11.669  -10.681  12.375  -0.513  -0.314   0.701  C16  N14  12  
N14  C19  C13  C  0  1  Y  N  N  10.221  -10.996  10.385   1.693   0.570   1.095  C19  N14  13  
N14  C2   C14  C  0  1  N  N  S  13.212   -7.661   9.699  -4.343   1.348  -0.786  C2   N14  14  
N14  C20  C15  C  0  1  Y  N  N  10.378   -9.745   9.792   2.503   1.588   1.587  C20  N14  15  
N14  C21  C16  C  0  1  Y  N  N  10.047   -9.574   8.462   3.870   1.515   1.393  C21  N14  16  
N14  C22  C17  C  0  1  Y  N  N   9.541  -10.661   7.753   4.385   0.416   0.708  C22  N14  17  
N14  C23  C18  C  0  1  Y  N  N   9.400  -11.879   8.405   3.516  -0.561   0.246  C23  N14  18  
N14  C26  C19  C  0  1  N  N  N   8.149  -11.418   5.925   6.078  -0.937  -0.241  C26  N14  19  
N14  C27  C20  C  0  1  N  N  N   8.145  -11.372   4.393   7.596  -1.069  -0.385  C27  N14  20  
N14  C29  C21  C  0  1  N  N  N   8.986   -9.066   4.481   7.808   1.342  -0.356  C29  N14  21  
N14  C30  C22  C  0  1  N  N  N   8.931   -9.129   6.009   6.290   1.474  -0.212  C30  N14  22  
N14  C31  C23  C  0  1  N  N  N   8.050   -9.946   2.438   9.569  -0.016  -1.315  C31  N14  23  
N14  F32  F1   F  0  1  N  N  N  14.842   -9.238  14.430  -2.896  -3.093  -0.997  F32  N14  24  
N14  N11  N1   N  0  1  Y  N  N  16.635   -7.765  11.091  -6.210  -1.350   0.900  N11  N14  25  
N14  N15  N2   N  0  1  Y  N  N  11.795  -10.930  13.668   0.032  -1.332   0.054  N15  N14  26  
N14  N17  N3   N  0  1  Y  N  N  12.586   -9.967  11.728  -1.826  -0.178   0.805  N17  N14  27  
N14  N18  N4   N  0  1  N  N  N  10.548  -11.209  11.731   0.312   0.635   1.285  N18  N14  28  
N14  N24  N5   N  0  1  Y  N  N   9.731  -12.004   9.679   2.216  -0.456   0.444  N24  N14  29  
N14  N25  N6   N  0  1  N  N  N   9.203  -10.515   6.400   5.764   0.297   0.493  N25  N14  30  
N14  N28  N7   N  0  1  N  N  N   7.992   -9.988   3.906   8.123   0.108  -1.090  N28  N14  31  
N14  N7   N8   N  0  1  Y  N  N  15.695   -7.339  10.149  -6.149  -0.128   0.221  N7   N14  32  
N14  H1   H1   H  0  1  N  N  N  14.422   -8.392   6.652  -7.072   3.295  -1.574  H1   N14  33  
N14  H2   H2   H  0  1  N  N  N  14.803   -8.975   8.308  -5.683   3.697  -0.541  H2   N14  34  
N14  H3   H3   H  0  1  N  N  N  12.910  -10.680  15.412  -0.265  -3.086  -1.043  H3   N14  35  
N14  H4   H4   H  0  1  N  N  N  16.791   -7.870   7.597  -6.306   2.189   1.121  H4   N14  36  
N14  H5   H5   H  0  1  N  N  N  15.875   -6.514   6.856  -7.901   2.694   0.516  H5   N14  37  
N14  H6   H6   H  0  1  N  N  N  16.994   -6.033   9.131  -8.172   0.393   0.428  H6   N14  38  
N14  H7   H7   H  0  1  N  N  N  15.247   -5.635   8.999  -7.483   0.668  -1.190  H7   N14  39  
N14  H8   H8   H  0  1  N  N  N  16.506   -9.023  12.795  -4.725  -2.767   1.464  H8   N14  40  
N14  H9   H9   H  0  1  N  N  N  13.702   -6.208   8.175  -6.057   1.082  -2.065  H9   N14  41  
N14  H10  H10  H  0  1  N  N  N  12.571   -7.496   7.640  -4.982   2.417  -2.546  H10  N14  42  
N14  H11  H11  H  0  1  N  N  N  12.229   -6.796  11.418  -2.844   1.816  -2.261  H11  N14  43  
N14  H12  H12  H  0  1  N  N  N  13.001   -5.602  10.321  -2.287   0.731  -0.965  H12  N14  44  
N14  H13  H13  H  0  1  N  N  N  11.464   -6.399   9.842  -3.355   0.110  -2.246  H13  N14  45  
N14  H14  H14  H  0  1  N  N  N  12.613   -8.583   9.727  -4.064   2.104  -0.052  H14  N14  46  
N14  H15  H15  H  0  1  N  N  N  10.756   -8.914  10.369   2.069   2.426   2.113  H15  N14  47  
N14  H16  H16  H  0  1  N  N  N  10.178   -8.616   7.981   4.523   2.291   1.763  H16  N14  48  
N14  H17  H17  H  0  1  N  N  N   9.016  -12.733   7.866   3.908  -1.416  -0.286  H17  N14  49  
N14  H18  H18  H  0  1  N  N  N   7.173  -11.089   6.311   5.621  -0.898  -1.229  H18  N14  50  
N14  H19  H19  H  0  1  N  N  N   8.353  -12.443   6.268   5.689  -1.795   0.307  H19  N14  51  
N14  H20  H20  H  0  1  N  N  N   7.309  -11.980   4.017   8.051  -1.134   0.603  H20  N14  52  
N14  H21  H21  H  0  1  N  N  N   9.094  -11.782   4.018   7.830  -1.968  -0.954  H21  N14  53  
N14  H22  H22  H  0  1  N  N  N   9.991   -9.354   4.140   8.197   2.201  -0.904  H22  N14  54  
N14  H23  H23  H  0  1  N  N  N   8.767   -8.040   4.150   8.266   1.304   0.633  H23  N14  55  
N14  H24  H24  H  0  1  N  N  N   9.691   -8.461   6.441   6.056   2.374   0.358  H24  N14  56  
N14  H25  H25  H  0  1  N  N  N   7.934   -8.827   6.362   5.835   1.540  -1.200  H25  N14  57  
N14  H26  H26  H  0  1  N  N  N   7.934   -8.907   2.096   9.768  -0.902  -1.918  H26  N14  58  
N14  H27  H27  H  0  1  N  N  N   9.020  -10.338   2.098   9.933   0.868  -1.838  H27  N14  59  
N14  H28  H28  H  0  1  N  N  N   7.239  -10.562   2.021  10.079  -0.107  -0.356  H28  N14  60  
N14  H29  H29  H  0  1  N  N  N   9.932  -11.782  12.271  -0.070   1.344   1.826  H29  N14  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
N14  C31  N28  SING  N  N   1  
N14  N28  C27  SING  N  N   2  
N14  N28  C29  SING  N  N   3  
N14  C27  C26  SING  N  N   4  
N14  C29  C30  SING  N  N   5  
N14  C26  N25  SING  N  N   6  
N14  C30  N25  SING  N  N   7  
N14  N25  C22  SING  N  N   8  
N14  C4   C5   SING  N  N   9  
N14  C4   C3   SING  N  N  10  
N14  C5   C6   SING  N  N  11  
N14  C22  C23  DOUB  Y  N  12  
N14  C22  C21  SING  Y  N  13  
N14  C3   C2   SING  N  N  14  
N14  C23  N24  SING  Y  N  15  
N14  C21  C20  DOUB  Y  N  16  
N14  C6   N7   SING  N  N  17  
N14  N24  C19  DOUB  Y  N  18  
N14  C2   C1   SING  N  N  19  
N14  C2   C8   SING  N  N  20  
N14  C20  C19  SING  Y  N  21  
N14  N7   C8   SING  Y  N  22  
N14  N7   N11  SING  Y  N  23  
N14  C19  N18  SING  N  N  24  
N14  C8   C9   DOUB  Y  N  25  
N14  N11  C10  DOUB  Y  N  26  
N14  C9   C10  SING  Y  N  27  
N14  C9   C12  SING  N  N  28  
N14  N17  C12  DOUB  Y  N  29  
N14  N17  C16  SING  Y  N  30  
N14  N18  C16  SING  N  N  31  
N14  C12  C13  SING  Y  N  32  
N14  C16  N15  DOUB  Y  N  33  
N14  N15  C14  SING  Y  N  34  
N14  C13  C14  DOUB  Y  N  35  
N14  C13  F32  SING  N  N  36  
N14  C4   H1   SING  N  N  37  
N14  C4   H2   SING  N  N  38  
N14  C14  H3   SING  N  N  39  
N14  C5   H4   SING  N  N  40  
N14  C5   H5   SING  N  N  41  
N14  C6   H6   SING  N  N  42  
N14  C6   H7   SING  N  N  43  
N14  C10  H8   SING  N  N  44  
N14  C3   H9   SING  N  N  45  
N14  C3   H10  SING  N  N  46  
N14  C1   H11  SING  N  N  47  
N14  C1   H12  SING  N  N  48  
N14  C1   H13  SING  N  N  49  
N14  C2   H14  SING  N  N  50  
N14  C20  H15  SING  N  N  51  
N14  C21  H16  SING  N  N  52  
N14  C23  H17  SING  N  N  53  
N14  C26  H18  SING  N  N  54  
N14  C26  H19  SING  N  N  55  
N14  C27  H20  SING  N  N  56  
N14  C27  H21  SING  N  N  57  
N14  C29  H22  SING  N  N  58  
N14  C29  H23  SING  N  N  59  
N14  C30  H24  SING  N  N  60  
N14  C30  H25  SING  N  N  61  
N14  C31  H26  SING  N  N  62  
N14  C31  H27  SING  N  N  63  
N14  C31  H28  SING  N  N  64  
N14  N18  H29  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
N14  SMILES            ACDLabs               12.01  "C5CCn1c(c(cn1)c2c(cnc(n2)Nc3ccc(cn3)N4CCN(CC4)C)F)C(C5)C"  
N14  InChI             InChI                 1.03   "InChI=1S/C23H29FN8/c1-16-5-3-4-8-32-22(16)18(14-27-32)21-19(24)15-26-23(29-21)28-20-7-6-17(13-25-20)31-11-9-30(2)10-12-31/h6-7,13-16H,3-5,8-12H2,1-2H3,(H,25,26,28,29)/t16-/m0/s1"  
N14  InChIKey          InChI                 1.03   UHCMUGYUWQCODZ-INIZCTEOSA-N  
N14  SMILES_CANONICAL  CACTVS                3.385  "C[C@H]1CCCCn2ncc(c3nc(Nc4ccc(cn4)N5CCN(C)CC5)ncc3F)c12"  
N14  SMILES            CACTVS                3.385  "C[CH]1CCCCn2ncc(c3nc(Nc4ccc(cn4)N5CCN(C)CC5)ncc3F)c12"  
N14  SMILES_CANONICAL  "OpenEye OEToolkits"  2.0.7  "C[C@H]1CCCCn2c1c(cn2)c3c(cnc(n3)Nc4ccc(cn4)N5CCN(CC5)C)F"  
N14  SMILES            "OpenEye OEToolkits"  2.0.7  "CC1CCCCn2c1c(cn2)c3c(cnc(n3)Nc4ccc(cn4)N5CCN(CC5)C)F"  
#   #
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
N14  "SYSTEMATIC NAME"  ACDLabs               12.01  "5-fluoro-N-[5-(4-methylpiperazin-1-yl)pyridin-2-yl]-4-[(4S)-4-methyl-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a]azepin-3-yl]pyrimidin-2-amine"  
N14  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  2.0.7  "5-fluoranyl-~{N}-[5-(4-methylpiperazin-1-yl)pyridin-2-yl]-4-[(4~{S})-4-methyl-5,6,7,8-tetrahydro-4~{H}-pyrazolo[1,5-a]azepin-3-yl]pyrimidin-2-amine"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
N14  "Create component"  2019-04-29  RCSB  
N14  "Initial release"   2020-07-29  RCSB  
##
