data_5A1
#

_chem_comp.id                                   5A1
_chem_comp.name                                 "4-[4-(5,5-dimethyl-4,5-dihydro-1,3-thiazol-2-yl)piperazin-1-yl]-6-(pentafluoroethyl)thieno[2,3-d]pyrimidine"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C17 H18 F5 N5 S2"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        MI-273
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2015-08-28
_chem_comp.pdbx_modified_date                   2021-03-01
_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                       451.480
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    5A1
_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       5DDF
_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
5A1  C4   C1   C  0  1  Y  N  N  13.224   7.609  12.151   2.883   2.280  -0.485  C4   5A1   1  
5A1  C5   C2   C  0  1  Y  N  N  13.343   8.925  11.864   1.802   1.586   0.068  C5   5A1   2  
5A1  C6   C3   C  0  1  Y  N  N  12.262   9.600  11.385   0.549   2.250   0.109  C6   5A1   3  
5A1  N1   N1   N  0  1  Y  N  N  11.122   8.923  11.200   0.459   3.481  -0.372  N1   5A1   4  
5A1  N3   N2   N  0  1  Y  N  N  12.098   6.953  11.988   2.692   3.523  -0.945  N3   5A1   5  
5A1  FAC  F1   F  0  1  N  N  N  19.043   8.067  12.393   2.598  -2.538  -0.794  FAC  5A1   6  
5A1  CBB  C4   C  0  1  N  N  N  17.812   7.898  11.921   3.948  -2.347  -0.479  CBB  5A1   7  
5A1  FAD  F2   F  0  1  N  N  N  17.635   6.623  11.590   4.522  -3.573  -0.128  FAD  5A1   8  
5A1  FAE  F3   F  0  1  N  N  N  17.641   8.662  10.848   4.615  -1.820  -1.590  FAE  5A1   9  
5A1  CBC  C5   C  0  1  N  N  N  16.808   8.287  12.982   4.065  -1.373   0.695  CBC  5A1  10  
5A1  FAF  F4   F  0  1  N  N  N  16.949   7.460  14.003   3.398  -1.900   1.806  FAF  5A1  11  
5A1  FAG  F5   F  0  1  N  N  N  17.101   9.506  13.396   5.415  -1.183   1.010  FAG  5A1  12  
5A1  CAU  C6   C  0  1  Y  N  N  15.363   8.274  12.574   3.446  -0.053   0.317  CAU  5A1  13  
5A1  SAS  S1   S  0  1  Y  N  N  14.579   7.006  12.731   4.319   1.268  -0.437  SAS  5A1  14  
5A1  CAI  C7   C  0  1  Y  N  N  14.612   9.300  12.132   2.180   0.259   0.516  CAI  5A1  15  
5A1  C2   C8   C  0  1  Y  N  N  10.975   7.590  11.518   1.512   4.093  -0.884  C2   5A1  16  
5A1  NAZ  N3   N  0  1  N  N  N  12.230  10.937  11.092  -0.562   1.621   0.642  NAZ  5A1  17  
5A1  CAM  C9   C  0  1  N  N  N  11.198  11.555  10.225  -1.742   2.494   0.579  CAM  5A1  18  
5A1  CAK  C10  C  0  1  N  N  N  11.303  13.099  10.228  -2.900   1.837   1.338  CAK  5A1  19  
5A1  CAL  C11  C  0  1  N  N  N  13.192  11.844  11.764  -0.812   0.338  -0.028  CAL  5A1  20  
5A1  CAJ  C12  C  0  1  N  N  N  12.459  12.979  12.501  -1.932  -0.408   0.706  CAJ  5A1  21  
5A1  NAY  N4   N  0  1  N  N  N  11.529  13.684  11.585  -3.100   0.481   0.802  NAY  5A1  22  
5A1  CAT  C13  C  0  1  N  N  N  10.898  14.800  11.941  -4.346   0.057   0.403  CAT  5A1  23  
5A1  SAR  S2   S  0  1  N  N  N  11.044  15.550  13.395  -4.709  -1.543  -0.254  SAR  5A1  24  
5A1  CBA  C14  C  0  1  N  N  N   9.994  16.887  13.051  -6.490  -1.240  -0.493  CBA  5A1  25  
5A1  CAA  C15  C  0  1  N  N  N   8.856  16.932  14.080  -6.864  -1.356  -1.972  CAA  5A1  26  
5A1  CAB  C16  C  0  1  N  N  N  10.788  18.198  13.104  -7.321  -2.209   0.350  CAB  5A1  27  
5A1  CAN  C17  C  0  1  N  N  N   9.443  16.665  11.671  -6.671   0.205   0.000  CAN  5A1  28  
5A1  NAO  N5   N  0  1  N  N  N  10.071  15.438  11.125  -5.417   0.763   0.456  NAO  5A1  29  
5A1  H2   H2   H  0  1  N  N  N  14.982  10.307  12.006   1.477  -0.424   0.970  H2   5A1  30  
5A1  H3   H3   H  0  1  N  N  N  10.032   7.076  11.404   1.397   5.097  -1.266  H3   5A1  31  
5A1  H4   H4   H  0  1  N  N  N  11.331  11.190   9.196  -1.507   3.455   1.035  H4   5A1  32  
5A1  H5   H5   H  0  1  N  N  N  10.203  11.264  10.592  -2.028   2.644  -0.462  H5   5A1  33  
5A1  H6   H6   H  0  1  N  N  N  12.142  13.391   9.580  -2.657   1.779   2.399  H6   5A1  34  
5A1  H7   H7   H  0  1  N  N  N  10.367  13.511   9.824  -3.808   2.423   1.198  H7   5A1  35  
5A1  H8   H8   H  0  1  N  N  N  13.783  11.267  12.490  -1.111   0.518  -1.061  H8   5A1  36  
5A1  H9   H9   H  0  1  N  N  N  13.863  12.280  11.009   0.096  -0.264  -0.012  H9   5A1  37  
5A1  H10  H10  H  0  1  N  N  N  11.887  12.555  13.340  -2.201  -1.305   0.149  H10  5A1  38  
5A1  H11  H11  H  0  1  N  N  N  13.199  13.696  12.887  -1.596  -0.681   1.706  H11  5A1  39  
5A1  H12  H12  H  0  1  N  N  N   8.193  17.781  13.858  -6.651  -2.365  -2.322  H12  5A1  40  
5A1  H13  H13  H  0  1  N  N  N   8.281  15.996  14.032  -7.927  -1.145  -2.095  H13  5A1  41  
5A1  H14  H14  H  0  1  N  N  N   9.278  17.051  15.089  -6.282  -0.639  -2.551  H14  5A1  42  
5A1  H15  H15  H  0  1  N  N  N  10.118  19.042  12.885  -7.059  -2.092   1.402  H15  5A1  43  
5A1  H16  H16  H  0  1  N  N  N  11.221  18.324  14.107  -8.380  -1.994   0.213  H16  5A1  44  
5A1  H17  H17  H  0  1  N  N  N  11.595  18.168  12.358  -7.114  -3.232   0.036  H17  5A1  45  
5A1  H18  H18  H  0  1  N  N  N   8.352  16.537  11.720  -7.062   0.814  -0.814  H18  5A1  46  
5A1  H19  H19  H  0  1  N  N  N   9.683  17.526  11.029  -7.383   0.214   0.825  H19  5A1  47  
#   #
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
5A1  C4   C5   DOUB  Y  N   1  
5A1  C4   N3   SING  Y  N   2  
5A1  C4   SAS  SING  Y  N   3  
5A1  C5   C6   SING  Y  N   4  
5A1  C5   CAI  SING  Y  N   5  
5A1  C6   N1   DOUB  Y  N   6  
5A1  C6   NAZ  SING  N  N   7  
5A1  N1   C2   SING  Y  N   8  
5A1  N3   C2   DOUB  Y  N   9  
5A1  FAC  CBB  SING  N  N  10  
5A1  CBB  FAD  SING  N  N  11  
5A1  CBB  FAE  SING  N  N  12  
5A1  CBB  CBC  SING  N  N  13  
5A1  CBC  FAF  SING  N  N  14  
5A1  CBC  FAG  SING  N  N  15  
5A1  CBC  CAU  SING  N  N  16  
5A1  CAU  SAS  SING  Y  N  17  
5A1  CAU  CAI  DOUB  Y  N  18  
5A1  NAZ  CAM  SING  N  N  19  
5A1  NAZ  CAL  SING  N  N  20  
5A1  CAM  CAK  SING  N  N  21  
5A1  CAK  NAY  SING  N  N  22  
5A1  CAL  CAJ  SING  N  N  23  
5A1  CAJ  NAY  SING  N  N  24  
5A1  NAY  CAT  SING  N  N  25  
5A1  CAT  SAR  SING  N  N  26  
5A1  CAT  NAO  DOUB  N  N  27  
5A1  SAR  CBA  SING  N  N  28  
5A1  CBA  CAA  SING  N  N  29  
5A1  CBA  CAB  SING  N  N  30  
5A1  CBA  CAN  SING  N  N  31  
5A1  CAN  NAO  SING  N  N  32  
5A1  CAI  H2   SING  N  N  33  
5A1  C2   H3   SING  N  N  34  
5A1  CAM  H4   SING  N  N  35  
5A1  CAM  H5   SING  N  N  36  
5A1  CAK  H6   SING  N  N  37  
5A1  CAK  H7   SING  N  N  38  
5A1  CAL  H8   SING  N  N  39  
5A1  CAL  H9   SING  N  N  40  
5A1  CAJ  H10  SING  N  N  41  
5A1  CAJ  H11  SING  N  N  42  
5A1  CAA  H12  SING  N  N  43  
5A1  CAA  H13  SING  N  N  44  
5A1  CAA  H14  SING  N  N  45  
5A1  CAB  H15  SING  N  N  46  
5A1  CAB  H16  SING  N  N  47  
5A1  CAB  H17  SING  N  N  48  
5A1  CAN  H18  SING  N  N  49  
5A1  CAN  H19  SING  N  N  50  
#   #
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
5A1  SMILES            ACDLabs               12.01  "c14c(c(ncn1)N2CCN(CC2)C=3SC(C)(C)CN=3)cc(C(C(F)(F)F)(F)F)s4"  
5A1  InChI             InChI                 1.03   "InChI=1S/C17H18F5N5S2/c1-15(2)8-23-14(29-15)27-5-3-26(4-6-27)12-10-7-11(16(18,19)17(20,21)22)28-13(10)25-9-24-12/h7,9H,3-6,8H2,1-2H3"  
5A1  InChIKey          InChI                 1.03   GFFCPACLFKCZTI-UHFFFAOYSA-N  
5A1  SMILES_CANONICAL  CACTVS                3.385  "CC1(C)CN=C(S1)N2CCN(CC2)c3ncnc4sc(cc34)C(F)(F)C(F)(F)F"  
5A1  SMILES            CACTVS                3.385  "CC1(C)CN=C(S1)N2CCN(CC2)c3ncnc4sc(cc34)C(F)(F)C(F)(F)F"  
5A1  SMILES_CANONICAL  "OpenEye OEToolkits"  1.9.2  "CC1(CN=C(S1)N2CCN(CC2)c3c4cc(sc4ncn3)C(C(F)(F)F)(F)F)C"  
5A1  SMILES            "OpenEye OEToolkits"  1.9.2  "CC1(CN=C(S1)N2CCN(CC2)c3c4cc(sc4ncn3)C(C(F)(F)F)(F)F)C"  
#   #
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
5A1  "SYSTEMATIC NAME"  ACDLabs               12.01  "4-[4-(5,5-dimethyl-4,5-dihydro-1,3-thiazol-2-yl)piperazin-1-yl]-6-(pentafluoroethyl)thieno[2,3-d]pyrimidine"  
5A1  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.9.2  "4-[4-(5,5-dimethyl-4H-1,3-thiazol-2-yl)piperazin-1-yl]-6-[1,1,2,2,2-pentakis(fluoranyl)ethyl]thieno[2,3-d]pyrimidine"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
5A1  "Create component"  2015-08-28  RCSB  
5A1  "Initial release"   2015-09-09  RCSB  
5A1  "Modify synonyms"   2021-03-01  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     5A1
_pdbx_chem_comp_synonyms.name        MI-273
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
