data_8AU
#

_chem_comp.id                                   8AU
_chem_comp.name                                 
;(4~{S})-6-azanyl-4-[3-(2-chlorophenyl)-5-(trifluoromethyl)phenyl]-3-methyl-4-propan-2-yl-2~{H}-pyrano[2,3-c]pyrazole-5-
carbonitrile
;

_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C24 H20 Cl F3 N4 O"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        
;(S)-6-amino-4-(2'-chloro-5-(trifluoromethyl)-[1,1-biphenyl]-3-yl)-4-isopropyl-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole
-5-carbonitrile
;

_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2017-05-25
_chem_comp.pdbx_modified_date                   2020-06-17
_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                       472.890
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    8AU
_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       5XMV
_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
8AU  C4   C1   C   0  1  N  N  S  30.160  43.462  20.697  -2.038  -0.230   0.269  C4    8AU   1  
8AU  C6   C2   C   0  1  Y  N  N  29.605  41.734  22.577  -3.097   1.742  -0.966  C6    8AU   2  
8AU  C8   C3   C   0  1  N  N  N  30.803  42.340  18.659  -1.941   0.228   2.752  C8    8AU   3  
8AU  C15  C4   C   0  1  N  N  N  28.656  45.602  20.513  -2.064  -2.193   1.814  C15   8AU   4  
8AU  C17  C5   C   0  1  Y  N  N  31.768  45.144  19.612  -0.062  -1.725  -0.089  C17   8AU   5  
8AU  C22  C6   C   0  1  Y  N  N  34.612  44.877  22.811   2.542   1.614  -0.477  C22   8AU   6  
8AU  C2   C7   C   0  1  N  N  N  30.198  40.951  20.342  -2.648   1.983   1.291  C2    8AU   7  
8AU  C3   C8   C   0  1  N  N  N  30.418  42.193  19.860  -2.226   0.710   1.434  C3    8AU   8  
8AU  N9   N1   N   0  1  N  N  N  31.158  42.485  17.553  -1.716  -0.154   3.798  N9    8AU   9  
8AU  C14  C9   C   0  1  N  N  N  28.931  44.163  20.047  -2.709  -1.571   0.574  C14   8AU  10  
8AU  C18  C10  C   0  1  Y  N  N  32.957  45.888  19.573   1.286  -1.926  -0.324  C18   8AU  11  
8AU  CL3  CL1  CL  0  0  N  N  N  32.598  45.335  24.767   4.141   0.362   1.329  CL33  8AU  12  
8AU  C25  C11  C   0  1  Y  N  N  34.276  45.036  24.246   3.728   1.662   0.255  C25   8AU  13  
8AU  C26  C12  C   0  1  Y  N  N  35.262  44.966  25.212   4.573   2.747   0.125  C26   8AU  14  
8AU  C27  C13  C   0  1  Y  N  N  36.583  44.739  24.832   4.245   3.783  -0.730  C27   8AU  15  
8AU  C28  C14  C   0  1  Y  N  N  36.920  44.589  23.492   3.070   3.740  -1.459  C28   8AU  16  
8AU  C29  C15  C   0  1  Y  N  N  35.951  44.646  22.488   2.217   2.661  -1.337  C29   8AU  17  
8AU  C20  C16  C   0  1  Y  N  N  33.589  44.952  21.724   1.632   0.449  -0.346  C20   8AU  18  
8AU  C19  C17  C   0  1  Y  N  N  33.853  45.776  20.634   2.135  -0.846  -0.453  C19   8AU  19  
8AU  C23  C18  C   0  1  N  N  N  33.303  46.830  18.423   1.828  -3.328  -0.440  C23   8AU  20  
8AU  F32  F1   F   0  1  N  N  N  33.151  48.086  18.823   1.772  -3.741  -1.775  F32   8AU  21  
8AU  F31  F2   F   0  1  N  N  N  32.537  46.625  17.359   3.155  -3.352   0.001  F31   8AU  22  
8AU  F30  F3   F   0  1  N  N  N  34.587  46.680  18.078   1.060  -4.191   0.348  F30   8AU  23  
8AU  C21  C19  C   0  1  Y  N  N  32.408  44.190  21.743   0.274   0.646  -0.104  C21   8AU  24  
8AU  C16  C20  C   0  1  Y  N  N  31.460  44.280  20.697  -0.567  -0.441   0.019  C16   8AU  25  
8AU  C24  C21  C   0  1  N  N  N  27.626  43.353  20.123  -4.200  -1.348   0.832  C24   8AU  26  
8AU  N7   N2   N   0  1  N  N  N  30.374  39.834  19.650  -2.777   2.744   2.426  N7    8AU  27  
8AU  C5   C22  C   0  1  Y  N  N  29.791  43.106  22.111  -2.677   0.394  -0.945  C5    8AU  28  
8AU  C10  C23  C   0  1  Y  N  N  29.549  43.869  23.371  -2.951  -0.147  -2.141  C10   8AU  29  
8AU  C13  C24  C   0  1  N  N  N  29.602  45.360  23.597  -2.672  -1.567  -2.560  C13   8AU  30  
8AU  N11  N3   N   0  1  Y  N  N  29.272  42.952  24.317  -3.524   0.813  -2.904  N11   8AU  31  
8AU  N12  N4   N   0  1  Y  N  N  29.298  41.607  23.880  -3.603   1.988  -2.140  N12   8AU  32  
8AU  O1   O1   O   0  1  N  N  N  29.744  40.728  21.689  -2.955   2.559   0.112  O1    8AU  33  
8AU  H1   H1   H   0  1  N  N  N  29.585  46.188  20.462  -2.224  -3.271   1.805  H1    8AU  34  
8AU  H2   H2   H   0  1  N  N  N  27.897  46.060  19.861  -0.994  -1.985   1.811  H2    8AU  35  
8AU  H3   H3   H   0  1  N  N  N  28.288  45.588  21.550  -2.514  -1.767   2.711  H3    8AU  36  
8AU  H4   H4   H   0  1  N  N  N  31.067  45.231  18.795  -0.724  -2.573   0.007  H4    8AU  37  
8AU  H5   H5   H   0  1  N  N  N  29.170  44.239  18.976  -2.583  -2.241  -0.276  H5    8AU  38  
8AU  H6   H6   H   0  1  N  N  N  35.010  45.087  26.255   5.492   2.786   0.691  H6    8AU  39  
8AU  H7   H7   H   0  1  N  N  N  37.353  44.679  25.587   4.908   4.630  -0.829  H7    8AU  40  
8AU  H8   H8   H   0  1  N  N  N  37.953  44.425  23.222   2.818   4.552  -2.125  H8    8AU  41  
8AU  H9   H9   H   0  1  N  N  N  36.239  44.511  21.456   1.301   2.629  -1.907  H9    8AU  42  
8AU  H10  H10  H   0  1  N  N  N  34.773  46.341  20.610   3.188  -1.004  -0.636  H10   8AU  43  
8AU  H11  H11  H   0  1  N  N  N  32.221  43.523  22.572  -0.119   1.648  -0.013  H11   8AU  44  
8AU  H12  H12  H   0  1  N  N  N  27.814  42.321  19.791  -4.646  -0.845  -0.026  H12   8AU  45  
8AU  H13  H13  H   0  1  N  N  N  27.261  43.343  21.160  -4.690  -2.309   0.986  H13   8AU  46  
8AU  H14  H14  H   0  1  N  N  N  26.869  43.815  19.472  -4.326  -0.730   1.721  H14   8AU  47  
8AU  H15  H15  H   0  1  N  N  N  30.148  39.047  20.224  -3.079   3.664   2.362  H15   8AU  48  
8AU  H16  H16  H   0  1  N  N  N  29.778  39.842  18.847  -2.565   2.363   3.293  H16   8AU  49  
8AU  H17  H17  H   0  1  N  N  N  28.607  45.794  23.420  -3.491  -2.209  -2.235  H17   8AU  50  
8AU  H18  H18  H   0  1  N  N  N  29.912  45.563  24.633  -2.582  -1.615  -3.645  H18   8AU  51  
8AU  H19  H19  H   0  1  N  N  N  30.327  45.810  22.903  -1.742  -1.905  -2.103  H19   8AU  52  
8AU  H20  H20  H   0  1  N  N  N  29.063  43.204  25.262  -3.828   0.707  -3.819  H20   8AU  53  
#   #
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
8AU  F31  C23  SING  N  N   1  
8AU  N9   C8   TRIP  N  N   2  
8AU  F30  C23  SING  N  N   3  
8AU  C23  F32  SING  N  N   4  
8AU  C23  C18  SING  N  N   5  
8AU  C8   C3   SING  N  N   6  
8AU  C18  C17  DOUB  Y  N   7  
8AU  C18  C19  SING  Y  N   8  
8AU  C17  C16  SING  Y  N   9  
8AU  N7   C2   SING  N  N  10  
8AU  C3   C2   DOUB  N  N  11  
8AU  C3   C4   SING  N  N  12  
8AU  C14  C24  SING  N  N  13  
8AU  C14  C15  SING  N  N  14  
8AU  C14  C4   SING  N  N  15  
8AU  C2   O1   SING  N  N  16  
8AU  C19  C20  DOUB  Y  N  17  
8AU  C16  C4   SING  N  N  18  
8AU  C16  C21  DOUB  Y  N  19  
8AU  C4   C5   SING  N  N  20  
8AU  O1   C6   SING  N  N  21  
8AU  C20  C21  SING  Y  N  22  
8AU  C20  C22  SING  N  N  23  
8AU  C5   C6   SING  Y  N  24  
8AU  C5   C10  DOUB  Y  N  25  
8AU  C29  C22  DOUB  Y  N  26  
8AU  C29  C28  SING  Y  N  27  
8AU  C6   N12  DOUB  Y  N  28  
8AU  C22  C25  SING  Y  N  29  
8AU  C10  C13  SING  N  N  30  
8AU  C10  N11  SING  Y  N  31  
8AU  C28  C27  DOUB  Y  N  32  
8AU  N12  N11  SING  Y  N  33  
8AU  C25  CL3  SING  N  N  34  
8AU  C25  C26  DOUB  Y  N  35  
8AU  C27  C26  SING  Y  N  36  
8AU  C15  H1   SING  N  N  37  
8AU  C15  H2   SING  N  N  38  
8AU  C15  H3   SING  N  N  39  
8AU  C17  H4   SING  N  N  40  
8AU  C14  H5   SING  N  N  41  
8AU  C26  H6   SING  N  N  42  
8AU  C27  H7   SING  N  N  43  
8AU  C28  H8   SING  N  N  44  
8AU  C29  H9   SING  N  N  45  
8AU  C19  H10  SING  N  N  46  
8AU  C21  H11  SING  N  N  47  
8AU  C24  H12  SING  N  N  48  
8AU  C24  H13  SING  N  N  49  
8AU  C24  H14  SING  N  N  50  
8AU  N7   H15  SING  N  N  51  
8AU  N7   H16  SING  N  N  52  
8AU  C13  H17  SING  N  N  53  
8AU  C13  H18  SING  N  N  54  
8AU  C13  H19  SING  N  N  55  
8AU  N11  H20  SING  N  N  56  
#   #
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
8AU  InChI             InChI                 1.03   "InChI=1S/C24H20ClF3N4O/c1-12(2)23(18(11-29)21(30)33-22-20(23)13(3)31-32-22)15-8-14(9-16(10-15)24(26,27)28)17-6-4-5-7-19(17)25/h4-10,12H,30H2,1-3H3,(H,31,32)/t23-/m0/s1"  
8AU  InChIKey          InChI                 1.03   MHJHVTMVGRIZDH-QHCPKHFHSA-N  
8AU  SMILES_CANONICAL  CACTVS                3.385  "CC(C)[C@]1(c2cc(cc(c2)C(F)(F)F)c3ccccc3Cl)C(=C(N)Oc4n[nH]c(C)c14)C#N"  
8AU  SMILES            CACTVS                3.385  "CC(C)[C]1(c2cc(cc(c2)C(F)(F)F)c3ccccc3Cl)C(=C(N)Oc4n[nH]c(C)c14)C#N"  
8AU  SMILES_CANONICAL  "OpenEye OEToolkits"  2.0.6  "Cc1c2c(n[nH]1)OC(=C([C@@]2(c3cc(cc(c3)C(F)(F)F)c4ccccc4Cl)C(C)C)C#N)N"  
8AU  SMILES            "OpenEye OEToolkits"  2.0.6  "Cc1c2c(n[nH]1)OC(=C(C2(c3cc(cc(c3)C(F)(F)F)c4ccccc4Cl)C(C)C)C#N)N"  
#
_pdbx_chem_comp_identifier.comp_id          8AU
_pdbx_chem_comp_identifier.type             "SYSTEMATIC NAME"
_pdbx_chem_comp_identifier.program          "OpenEye OEToolkits"
_pdbx_chem_comp_identifier.program_version  2.0.6
_pdbx_chem_comp_identifier.identifier       "(4~{S})-6-azanyl-4-[3-(2-chlorophenyl)-5-(trifluoromethyl)phenyl]-3-methyl-4-propan-2-yl-2~{H}-pyrano[2,3-c]pyrazole-5-carbonitrile"
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
8AU  "Create component"  2017-05-25  PDBJ  
8AU  "Initial release"   2017-11-29  RCSB  
8AU  "Modify synonyms"   2020-06-05  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     8AU
_pdbx_chem_comp_synonyms.name        "(S)-6-amino-4-(2'-chloro-5-(trifluoromethyl)-[1,1-biphenyl]-3-yl)-4-isopropyl-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile"
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
