data_72F
#

_chem_comp.id                                   72F
_chem_comp.name                                 "N-[3-({6-[(2S)-2-cyano-3-(methylamino)-3-oxopropyl]-7-(2-methoxyethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethynyl)-4-methylphenyl]-3-(trifluoromethyl)benzamide"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C31 H27 F3 N6 O3"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        "N-[3-({6-[(1E)-2-cyano-3-(methylamino)-3-oxoprop-1-en-1-yl]-7-(2-methoxyethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethynyl)-4-methylphenyl]-3-(trifluoromethyl)benzamide inhibitor, bound form"
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2016-08-15
_chem_comp.pdbx_modified_date                   2021-03-13
_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                       588.580
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    72F
_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       5SYS
_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
72F  C7   C1   C  0  1  Y  N  N   6.072  37.283   5.737  -2.502   1.007   0.372  C7   72F   1  
72F  C10  C2   C  0  1  Y  N  N   3.064  35.149   7.415   0.275  -1.923   0.268  C10  72F   2  
72F  C6   C3   C  0  1  Y  N  N   7.328  36.676   5.446  -2.289   2.434   0.082  C6   72F   3  
72F  C4   C4   C  0  1  Y  N  N   9.861  36.311   4.579  -2.569   5.062  -0.306  C4   72F   4  
72F  C5   C5   C  0  1  Y  N  N   8.081  35.533   5.730  -1.197   3.211  -0.289  C5   72F   5  
72F  C9   C6   C  0  1  N  N  N   4.155  35.931   6.908  -0.710  -0.884   0.305  C9   72F   6  
72F  C1   C7   C  0  1  N  N  N   6.680  39.627   2.178  -6.658   2.163  -0.411  C1   72F   7  
72F  N1   N1   N  0  1  Y  N  N   9.283  37.449   4.188  -3.630   4.368   0.045  N1   72F   8  
72F  C2   C8   C  0  1  N  N  N   7.482  39.804   3.460  -5.859   2.319   0.883  C2   72F   9  
72F  O1   O1   O  0  1  N  N  N  -1.521  32.408   6.927   3.733  -0.330   0.511  O1   72F  10  
72F  N2   N2   N  0  1  Y  N  N   9.338  35.336   5.318  -1.380   4.510  -0.471  N2   72F  11  
72F  C3   C9   C  0  1  Y  N  N   8.029  37.599   4.640  -3.542   3.057   0.249  C3   72F  12  
72F  C11  C10  C  0  1  Y  N  N   2.345  34.292   6.579   1.598  -1.624  -0.064  C11  72F  13  
72F  C13  C11  C  0  1  N  N  N  -0.514  31.918   6.417   4.417  -1.166  -0.045  C13  72F  14  
72F  C12  C12  C  0  1  Y  N  N   1.218  33.626   7.066   2.545  -2.634  -0.092  C12  72F  15  
72F  N3   N3   N  0  1  N  N  N   0.652  32.603   6.253   3.872  -2.339  -0.424  N3   72F  16  
72F  C8   C13  C  0  1  N  N  N   5.036  36.565   6.407  -1.518  -0.032   0.335  C8   72F  17  
72F  N5   N4   N  0  1  N  N  N   2.382  38.417   7.061  -3.034  -1.784  -1.734  N5   72F  18  
72F  C30  C14  C  0  1  N  N  N   2.902  38.846   6.143  -3.903  -1.488  -1.065  C30  72F  19  
72F  C27  C15  C  0  1  N  N  S   3.625  39.374   4.984  -5.029  -1.104  -0.198  C27  72F  20  
72F  C28  C16  C  0  1  N  N  N   2.899  40.609   4.443  -5.808  -2.335   0.188  C28  72F  21  
72F  O2   O2   O  0  1  N  N  N   2.551  41.519   5.195  -5.923  -2.638   1.356  O2   72F  22  
72F  N4   N5   N  0  1  N  N  N   2.662  40.617   3.136  -6.377  -3.099  -0.766  N4   72F  23  
72F  C29  C17  C  0  1  N  N  N   1.661  41.479   2.533  -7.135  -4.295  -0.391  C29  72F  24  
72F  C26  C18  C  0  1  N  N  N   5.080  39.675   5.422  -4.493  -0.424   1.063  C26  72F  25  
72F  C25  C19  C  0  1  Y  N  N   6.066  38.530   5.166  -3.819   0.871   0.688  C25  72F  26  
72F  N    N6   N  0  1  Y  N  N   7.226  38.719   4.428  -4.438   2.086   0.611  N    72F  27  
72F  O    O3   O  0  1  N  N  N   7.471  40.073   1.072  -8.044   2.391  -0.146  O    72F  28  
72F  C    C20  C  0  1  N  N  N   7.491  41.484   0.843  -8.884   2.269  -1.295  C    72F  29  
72F  C23  C21  C  0  1  Y  N  N   2.689  35.327   8.754  -0.083  -3.240   0.571  C23  72F  30  
72F  C24  C22  C  0  1  N  N  N   3.601  36.023   9.731  -1.508  -3.569   0.936  C24  72F  31  
72F  C22  C23  C  0  1  Y  N  N   1.519  34.710   9.190   0.868  -4.239   0.534  C22  72F  32  
72F  C21  C24  C  0  1  Y  N  N   0.782  33.882   8.364   2.178  -3.941   0.211  C21  72F  33  
72F  C14  C25  C  0  1  Y  N  N  -0.528  30.510   5.903   5.847  -0.897  -0.306  C14  72F  34  
72F  C20  C26  C  0  1  Y  N  N   0.638  29.756   5.758   6.635  -1.856  -0.945  C20  72F  35  
72F  C19  C27  C  0  1  Y  N  N   0.582  28.472   5.238   7.969  -1.599  -1.185  C19  72F  36  
72F  C18  C28  C  0  1  Y  N  N  -0.631  27.930   4.859   8.526  -0.394  -0.794  C18  72F  37  
72F  C16  C29  C  0  1  Y  N  N  -1.801  28.666   4.995   7.750   0.561  -0.161  C16  72F  38  
72F  C15  C30  C  0  1  Y  N  N  -1.746  29.949   5.530   6.413   0.318   0.080  C15  72F  39  
72F  C17  C31  C  0  1  N  N  N  -3.101  28.125   4.510   8.365   1.870   0.262  C17  72F  40  
72F  F    F1   F  0  1  N  N  N  -3.634  28.886   3.561   8.242   2.017   1.648  F    72F  41  
72F  F1   F2   F  0  1  N  N  N  -4.026  28.077   5.463   9.718   1.885  -0.091  F1   72F  42  
72F  F2   F3   F  0  1  N  N  N  -2.987  26.891   4.011   7.704   2.924  -0.379  F2   72F  43  
72F  H1   H1   H  0  1  N  N  N  10.881  36.163   4.255  -2.673   6.125  -0.465  H1   72F  44  
72F  H2   H2   H  0  1  N  N  N   7.617  34.758   6.321  -0.223   2.766  -0.425  H2   72F  45  
72F  H3   H3   H  0  1  N  N  N   5.756  40.222   2.235  -6.306   2.888  -1.146  H3   72F  46  
72F  H4   H4   H  0  1  N  N  N   6.425  38.565   2.045  -6.524   1.155  -0.802  H4   72F  47  
72F  H5   H5   H  0  1  N  N  N   8.553  39.811   3.210  -5.993   3.328   1.274  H5   72F  48  
72F  H6   H6   H  0  1  N  N  N   7.206  40.764   3.921  -6.211   1.595   1.618  H6   72F  49  
72F  H7   H7   H  0  1  N  N  N   2.660  34.144   5.557   1.881  -0.608  -0.299  H7   72F  50  
72F  H8   H8   H  0  1  N  N  N   1.187  32.352   5.446   4.399  -2.979  -0.927  H8   72F  51  
72F  H9   H9   H  0  1  N  N  N   3.653  38.611   4.192  -5.681  -0.414  -0.734  H9   72F  52  
72F  H10  H10  H  0  1  N  N  N   3.192  40.008   2.546  -6.285  -2.856  -1.701  H10  72F  53  
72F  H11  H11  H  0  1  N  N  N   1.642  41.314   1.446  -6.482  -4.985   0.145  H11  72F  54  
72F  H12  H12  H  0  1  N  N  N   0.673  41.246   2.957  -7.968  -4.011   0.251  H12  72F  55  
72F  H13  H13  H  0  1  N  N  N   1.910  42.530   2.740  -7.516  -4.780  -1.290  H13  72F  56  
72F  H14  H14  H  0  1  N  N  N   5.430  40.560   4.870  -5.319  -0.220   1.745  H14  72F  57  
72F  H15  H15  H  0  1  N  N  N   5.077  39.892   6.500  -3.772  -1.080   1.551  H15  72F  58  
72F  H16  H16  H  0  1  N  N  N   8.127  41.706  -0.027  -9.919   2.456  -1.010  H16  72F  59  
72F  H17  H17  H  0  1  N  N  N   6.468  41.838   0.649  -8.577   2.995  -2.048  H17  72F  60  
72F  H18  H18  H  0  1  N  N  N   7.893  41.994   1.731  -8.796   1.262  -1.705  H18  72F  61  
72F  H19  H19  H  0  1  N  N  N   3.344  37.092   9.775  -2.066  -3.817   0.034  H19  72F  62  
72F  H20  H20  H  0  1  N  N  N   3.480  35.575  10.728  -1.521  -4.420   1.617  H20  72F  63  
72F  H21  H21  H  0  1  N  N  N   4.645  35.910   9.403  -1.967  -2.708   1.422  H21  72F  64  
72F  H22  H22  H  0  1  N  N  N   1.178  34.883  10.200   0.589  -5.256   0.768  H22  72F  65  
72F  H23  H23  H  0  1  N  N  N  -0.132  33.434   8.725   2.919  -4.726   0.188  H23  72F  66  
72F  H24  H24  H  0  1  N  N  N   1.589  30.175   6.052   6.202  -2.797  -1.249  H24  72F  67  
72F  H25  H25  H  0  1  N  N  N   1.488  27.895   5.129   8.580  -2.339  -1.679  H25  72F  68  
72F  H26  H26  H  0  1  N  N  N  -0.670  26.929   4.455   9.571  -0.199  -0.980  H26  72F  69  
72F  H27  H27  H  0  1  N  N  N  -2.657  30.515   5.657   5.808   1.064   0.574  H27  72F  70  
#   #
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
72F  C    O    SING  N  N   1  
72F  O    C1   SING  N  N   2  
72F  C1   C2   SING  N  N   3  
72F  C29  N4   SING  N  N   4  
72F  N4   C28  SING  N  N   5  
72F  C2   N    SING  N  N   6  
72F  F    C17  SING  N  N   7  
72F  F2   C17  SING  N  N   8  
72F  N1   C4   DOUB  Y  N   9  
72F  N1   C3   SING  Y  N  10  
72F  N    C3   SING  Y  N  11  
72F  N    C25  SING  Y  N  12  
72F  C28  C27  SING  N  N  13  
72F  C28  O2   DOUB  N  N  14  
72F  C17  C16  SING  N  N  15  
72F  C17  F1   SING  N  N  16  
72F  C4   N2   SING  Y  N  17  
72F  C3   C6   DOUB  Y  N  18  
72F  C18  C16  DOUB  Y  N  19  
72F  C18  C19  SING  Y  N  20  
72F  C27  C26  SING  N  N  21  
72F  C27  C30  SING  N  N  22  
72F  C16  C15  SING  Y  N  23  
72F  C25  C26  SING  N  N  24  
72F  C25  C7   DOUB  Y  N  25  
72F  C19  C20  DOUB  Y  N  26  
72F  N2   C5   DOUB  Y  N  27  
72F  C6   C5   SING  Y  N  28  
72F  C6   C7   SING  Y  N  29  
72F  C15  C14  DOUB  Y  N  30  
72F  C7   C8   SING  N  N  31  
72F  C20  C14  SING  Y  N  32  
72F  C14  C13  SING  N  N  33  
72F  C30  N5   TRIP  N  N  34  
72F  N3   C13  SING  N  N  35  
72F  N3   C12  SING  N  N  36  
72F  C8   C9   TRIP  N  N  37  
72F  C13  O1   DOUB  N  N  38  
72F  C11  C12  DOUB  Y  N  39  
72F  C11  C10  SING  Y  N  40  
72F  C9   C10  SING  N  N  41  
72F  C12  C21  SING  Y  N  42  
72F  C10  C23  DOUB  Y  N  43  
72F  C21  C22  DOUB  Y  N  44  
72F  C23  C22  SING  Y  N  45  
72F  C23  C24  SING  N  N  46  
72F  C4   H1   SING  N  N  47  
72F  C5   H2   SING  N  N  48  
72F  C1   H3   SING  N  N  49  
72F  C1   H4   SING  N  N  50  
72F  C2   H5   SING  N  N  51  
72F  C2   H6   SING  N  N  52  
72F  C11  H7   SING  N  N  53  
72F  N3   H8   SING  N  N  54  
72F  C27  H9   SING  N  N  55  
72F  N4   H10  SING  N  N  56  
72F  C29  H11  SING  N  N  57  
72F  C29  H12  SING  N  N  58  
72F  C29  H13  SING  N  N  59  
72F  C26  H14  SING  N  N  60  
72F  C26  H15  SING  N  N  61  
72F  C    H16  SING  N  N  62  
72F  C    H17  SING  N  N  63  
72F  C    H18  SING  N  N  64  
72F  C24  H19  SING  N  N  65  
72F  C24  H20  SING  N  N  66  
72F  C24  H21  SING  N  N  67  
72F  C22  H22  SING  N  N  68  
72F  C21  H23  SING  N  N  69  
72F  C20  H24  SING  N  N  70  
72F  C19  H25  SING  N  N  71  
72F  C18  H26  SING  N  N  72  
72F  C15  H27  SING  N  N  73  
#   #
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
72F  SMILES            ACDLabs               12.01  "c4(C#Cc1c(ccc(c1)NC(=O)c2cccc(c2)C(F)(F)F)C)c3cncnc3n(CCOC)c4CC(C#N)C(=O)NC"  
72F  InChI             InChI                 1.03   "InChI=1S/C31H27F3N6O3/c1-19-7-9-24(39-30(42)21-5-4-6-23(13-21)31(32,33)34)14-20(19)8-10-25-26-17-37-18-38-28(26)40(11-12-43-3)27(25)15-22(16-35)29(41)36-2/h4-7,9,13-14,17-18,22H,11-12,15H2,1-3H3,(H,36,41)(H,39,42)/t22-/m0/s1"  
72F  InChIKey          InChI                 1.03   JDCJZTAGQPRSAO-QFIPXVFZSA-N  
72F  SMILES_CANONICAL  CACTVS                3.385  "CNC(=O)[C@@H](Cc1n(CCOC)c2ncncc2c1C#Cc3cc(NC(=O)c4cccc(c4)C(F)(F)F)ccc3C)C#N"  
72F  SMILES            CACTVS                3.385  "CNC(=O)[CH](Cc1n(CCOC)c2ncncc2c1C#Cc3cc(NC(=O)c4cccc(c4)C(F)(F)F)ccc3C)C#N"  
72F  SMILES_CANONICAL  "OpenEye OEToolkits"  2.0.5  "Cc1ccc(cc1C#Cc2c3cncnc3n(c2C[C@@H](C#N)C(=O)NC)CCOC)NC(=O)c4cccc(c4)C(F)(F)F"  
72F  SMILES            "OpenEye OEToolkits"  2.0.5  "Cc1ccc(cc1C#Cc2c3cncnc3n(c2CC(C#N)C(=O)NC)CCOC)NC(=O)c4cccc(c4)C(F)(F)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
72F  "SYSTEMATIC NAME"  ACDLabs               12.01  "N-[3-({6-[(2S)-2-cyano-3-(methylamino)-3-oxopropyl]-7-(2-methoxyethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethynyl)-4-methylphenyl]-3-(trifluoromethyl)benzamide"  
72F  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  2.0.5  "~{N}-[3-[2-[6-[(2~{S})-2-cyano-3-(methylamino)-3-oxidanylidene-propyl]-7-(2-methoxyethyl)pyrrolo[2,3-d]pyrimidin-5-yl]ethynyl]-4-methyl-phenyl]-3-(trifluoromethyl)benzamide"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
72F  "Create component"  2016-08-15  RCSB  
72F  "Initial release"   2017-08-16  RCSB  
72F  "Modify synonyms"   2021-03-13  RCSB  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     72F
_pdbx_chem_comp_synonyms.name        "N-[3-({6-[(1E)-2-cyano-3-(methylamino)-3-oxoprop-1-en-1-yl]-7-(2-methoxyethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethynyl)-4-methylphenyl]-3-(trifluoromethyl)benzamide inhibitor, bound form"
_pdbx_chem_comp_synonyms.provenance  PDB
_pdbx_chem_comp_synonyms.type        ?
##
