data_8AO
#

_chem_comp.id                                   8AO
_chem_comp.name                                 
;(4~{S})-6-azanyl-3-methyl-4-[3-[4-(phenylmethyl)sulfonylphenyl]-5-(trifluoromethyl)phenyl]-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                              "C31 H27 F3 N4 O3 S"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        
;(S)-6-amino-4-(4'-(benzylsulfonyl)-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                       592.631
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    8AO
_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       5XMR
_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
8AO  C2   C1   C  0  1  N  N  N  29.960  35.824   97.079    2.885   3.090  -1.050  C2   8AO   1  
8AO  C3   C2   C  0  1  N  N  N  30.290  34.594   97.545    3.409   1.881  -1.338  C3   8AO   2  
8AO  C4   C3   C  0  1  N  N  S  30.133  33.333   96.699    3.899   0.924  -0.280  C4   8AO   3  
8AO  C5   C4   C  0  1  Y  N  N  29.833  33.673   95.260    3.973   1.668   1.028  C5   8AO   4  
8AO  C6   C5   C  0  1  Y  N  N  29.507  35.026   94.801    3.397   2.946   1.202  C6   8AO   5  
8AO  C8   C6   C  0  1  N  N  N  30.725  34.433   98.746    3.506   1.488  -2.712  C8   8AO   6  
8AO  C10  C7   C  0  1  Y  N  N  29.766  32.904   93.972    4.545   1.307   2.187  C10  8AO   7  
8AO  C12  C8   C  0  1  N  N  N  30.019  31.444   93.678    5.278   0.018   2.454  C12  8AO   8  
8AO  C13  C9   C  0  1  N  N  N  28.924  32.552   97.274    5.286   0.402  -0.658  C13  8AO   9  
8AO  C14  C10  C  0  1  N  N  N  28.887  31.105   96.797    5.215  -0.301  -2.015  C14  8AO  10  
8AO  C15  C11  C  0  1  Y  N  N  31.450  32.550   96.804    2.938  -0.230  -0.155  C15  8AO  11  
8AO  C16  C12  C  0  1  Y  N  N  31.706  31.766   97.947    3.409  -1.530  -0.209  C16  8AO  12  
8AO  C17  C13  C  0  1  Y  N  N  32.880  31.040   98.075    2.533  -2.594  -0.095  C17  8AO  13  
8AO  C18  C14  C  0  1  Y  N  N  33.835  31.094   97.079    1.182  -2.364   0.073  C18  8AO  14  
8AO  C19  C15  C  0  1  Y  N  N  33.625  31.851   95.935    0.702  -1.057   0.128  C19  8AO  15  
8AO  C20  C16  C  0  1  Y  N  N  32.443  32.577   95.794    1.590   0.011   0.018  C20  8AO  16  
8AO  O52  O1   O  0  1  N  N  N  39.001  32.442   92.233   -5.238   1.253   1.466  O52  8AO  17  
8AO  S44  S1   S  0  1  N  N  N  37.836  31.701   91.827   -5.179  -0.031   0.860  S44  8AO  18  
8AO  O51  O2   O  0  1  N  N  N  37.343  32.273   90.630   -5.654  -1.184   1.540  O51  8AO  19  
8AO  C56  C17  C  0  1  N  N  N  38.188  30.145   91.326   -5.840   0.031  -0.828  C56  8AO  20  
8AO  C57  C18  C  0  1  Y  N  N  38.678  29.173   92.389   -7.325   0.287  -0.776  C57  8AO  21  
8AO  C62  C19  C  0  1  Y  N  N  39.453  29.560   93.503   -7.804   1.583  -0.789  C62  8AO  22  
8AO  C61  C20  C  0  1  Y  N  N  39.866  28.613   94.445   -9.165   1.817  -0.742  C61  8AO  23  
8AO  C60  C21  C  0  1  Y  N  N  39.519  27.270   94.281  -10.048   0.754  -0.682  C60  8AO  24  
8AO  C59  C22  C  0  1  Y  N  N  38.753  26.872   93.179   -9.568  -0.542  -0.670  C59  8AO  25  
8AO  C58  C23  C  0  1  Y  N  N  38.335  27.819   92.236   -8.207  -0.776  -0.723  C58  8AO  26  
8AO  C41  C24  C  0  1  Y  N  N  36.690  31.765   92.942   -3.456  -0.331   0.646  C41  8AO  27  
8AO  C40  C25  C  0  1  Y  N  N  35.339  31.700   92.582   -2.985  -1.631   0.591  C40  8AO  28  
8AO  C39  C26  C  0  1  Y  N  N  34.340  31.720   93.550   -1.636  -1.872   0.423  C39  8AO  29  
8AO  C42  C27  C  0  1  Y  N  N  37.030  31.874   94.291   -2.580   0.733   0.527  C42  8AO  30  
8AO  C43  C28  C  0  1  Y  N  N  36.031  31.906   95.249   -1.230   0.503   0.359  C43  8AO  31  
8AO  C32  C29  C  0  1  Y  N  N  34.681  31.842   94.888   -0.749  -0.804   0.308  C32  8AO  32  
8AO  C33  C30  C  0  1  N  N  N  33.132  30.229   99.314    3.053  -4.007  -0.155  C33  8AO  33  
8AO  F49  F1   F  0  1  N  N  N  32.040  29.982  100.026    3.379  -4.439   1.135  F49  8AO  34  
8AO  F48  F2   F  0  1  N  N  N  33.932  30.983  100.034    2.070  -4.844  -0.693  F48  8AO  35  
8AO  F47  F3   F  0  1  N  N  N  33.736  29.096   98.984    4.195  -4.049  -0.963  F47  8AO  36  
8AO  C34  C31  C  0  1  N  N  N  27.546  33.207   97.071    6.267   1.574  -0.742  C34  8AO  37  
8AO  N9   N1   N  0  1  N  N  N  31.126  34.297   99.829    3.582   1.176  -3.801  N9   8AO  38  
8AO  N7   N2   N  0  1  N  N  N  30.082  36.936   97.824    2.469   3.872  -2.099  N7   8AO  39  
8AO  N54  N3   N  0  1  Y  N  N  29.444  33.805   93.018    4.345   2.310   3.073  N54  8AO  40  
8AO  N11  N4   N  0  1  Y  N  N  29.271  35.127   93.474    3.621   3.325   2.427  N11  8AO  41  
8AO  O1   O3   O  0  1  N  N  N  29.453  36.035   95.723    2.736   3.582   0.196  O1   8AO  42  
8AO  H1   H1   H  0  1  N  N  N  31.084  31.295   93.447    6.335   0.146   2.220  H1   8AO  43  
8AO  H2   H2   H  0  1  N  N  N  29.747  30.841   94.557    5.168  -0.252   3.504  H2   8AO  44  
8AO  H3   H3   H  0  1  N  N  N  29.410  31.133   92.817    4.861  -0.773   1.830  H3   8AO  45  
8AO  H4   H4   H  0  1  N  N  N  29.082  32.511   98.362    5.628  -0.304   0.099  H4   8AO  46  
8AO  H5   H5   H  0  1  N  N  N  28.014  30.597   97.232    6.044  -1.002  -2.106  H5   8AO  47  
8AO  H6   H6   H  0  1  N  N  N  28.815  31.083   95.700    4.272  -0.842  -2.095  H6   8AO  48  
8AO  H7   H7   H  0  1  N  N  N  29.806  30.591   97.115    5.277   0.440  -2.812  H7   8AO  49  
8AO  H8   H8   H  0  1  N  N  N  30.973  31.730   98.739    4.465  -1.714  -0.342  H8   8AO  50  
8AO  H9   H9   H  0  1  N  N  N  34.756  30.541   97.192    0.499  -3.196   0.161  H9   8AO  51  
8AO  H10  H10  H  0  1  N  N  N  32.283  33.167   94.904    1.223   1.026   0.060  H10  8AO  52  
8AO  H11  H11  H  0  1  N  N  N  37.272  29.723   90.886   -5.352   0.835  -1.380  H11  8AO  53  
8AO  H12  H12  H  0  1  N  N  N  38.968  30.213   90.553   -5.652  -0.919  -1.327  H12  8AO  54  
8AO  H13  H13  H  0  1  N  N  N  39.729  30.596   93.629   -7.115   2.413  -0.835  H13  8AO  55  
8AO  H14  H14  H  0  1  N  N  N  40.453  28.920   95.298   -9.540   2.830  -0.751  H14  8AO  56  
8AO  H15  H15  H  0  1  N  N  N  39.842  26.537   95.006  -11.111   0.937  -0.645  H15  8AO  57  
8AO  H16  H16  H  0  1  N  N  N  38.484  25.833   93.056  -10.258  -1.372  -0.624  H16  8AO  58  
8AO  H17  H17  H  0  1  N  N  N  37.746  27.507   91.386   -7.833  -1.789  -0.718  H17  8AO  59  
8AO  H18  H18  H  0  1  N  N  N  35.068  31.633   91.539   -3.673  -2.458   0.681  H18  8AO  60  
8AO  H19  H19  H  0  1  N  N  N  33.303  31.641   93.260   -1.269  -2.887   0.381  H19  8AO  61  
8AO  H20  H20  H  0  1  N  N  N  38.067  31.933   94.586   -2.954   1.745   0.567  H20  8AO  62  
8AO  H21  H21  H  0  1  N  N  N  36.298  31.982   96.293   -0.547   1.335   0.266  H21  8AO  63  
8AO  H22  H22  H  0  1  N  N  N  26.767  32.570   97.516    6.318   2.074   0.225  H22  8AO  64  
8AO  H23  H23  H  0  1  N  N  N  27.534  34.194   97.557    7.255   1.202  -1.011  H23  8AO  65  
8AO  H24  H24  H  0  1  N  N  N  27.352  33.326   95.995    5.925   2.279  -1.499  H24  8AO  66  
8AO  H25  H25  H  0  1  N  N  N  29.792  37.730   97.289    2.557   3.549  -3.009  H25  8AO  67  
8AO  H26  H26  H  0  1  N  N  N  29.509  36.855   98.639    2.087   4.747  -1.929  H26  8AO  68  
8AO  H27  H27  H  0  1  N  N  N  29.336  33.552   92.057    4.648   2.326   3.994  H27  8AO  69  
#   #
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
8AO  O51  S44  DOUB  N  N   1  
8AO  C56  S44  SING  N  N   2  
8AO  C56  C57  SING  N  N   3  
8AO  S44  O52  DOUB  N  N   4  
8AO  S44  C41  SING  N  N   5  
8AO  C58  C57  DOUB  Y  N   6  
8AO  C58  C59  SING  Y  N   7  
8AO  C57  C62  SING  Y  N   8  
8AO  C40  C41  DOUB  Y  N   9  
8AO  C40  C39  SING  Y  N  10  
8AO  C41  C42  SING  Y  N  11  
8AO  N54  N11  SING  Y  N  12  
8AO  N54  C10  SING  Y  N  13  
8AO  C59  C60  DOUB  Y  N  14  
8AO  N11  C6   DOUB  Y  N  15  
8AO  C62  C61  DOUB  Y  N  16  
8AO  C39  C32  DOUB  Y  N  17  
8AO  C12  C10  SING  N  N  18  
8AO  C10  C5   DOUB  Y  N  19  
8AO  C60  C61  SING  Y  N  20  
8AO  C42  C43  DOUB  Y  N  21  
8AO  C6   C5   SING  Y  N  22  
8AO  C6   O1   SING  N  N  23  
8AO  C32  C43  SING  Y  N  24  
8AO  C32  C19  SING  N  N  25  
8AO  C5   C4   SING  N  N  26  
8AO  O1   C2   SING  N  N  27  
8AO  C20  C19  DOUB  Y  N  28  
8AO  C20  C15  SING  Y  N  29  
8AO  C19  C18  SING  Y  N  30  
8AO  C4   C15  SING  N  N  31  
8AO  C4   C13  SING  N  N  32  
8AO  C4   C3   SING  N  N  33  
8AO  C14  C13  SING  N  N  34  
8AO  C15  C16  DOUB  Y  N  35  
8AO  C34  C13  SING  N  N  36  
8AO  C2   C3   DOUB  N  N  37  
8AO  C2   N7   SING  N  N  38  
8AO  C18  C17  DOUB  Y  N  39  
8AO  C3   C8   SING  N  N  40  
8AO  C16  C17  SING  Y  N  41  
8AO  C17  C33  SING  N  N  42  
8AO  C8   N9   TRIP  N  N  43  
8AO  F47  C33  SING  N  N  44  
8AO  C33  F49  SING  N  N  45  
8AO  C33  F48  SING  N  N  46  
8AO  C12  H1   SING  N  N  47  
8AO  C12  H2   SING  N  N  48  
8AO  C12  H3   SING  N  N  49  
8AO  C13  H4   SING  N  N  50  
8AO  C14  H5   SING  N  N  51  
8AO  C14  H6   SING  N  N  52  
8AO  C14  H7   SING  N  N  53  
8AO  C16  H8   SING  N  N  54  
8AO  C18  H9   SING  N  N  55  
8AO  C20  H10  SING  N  N  56  
8AO  C56  H11  SING  N  N  57  
8AO  C56  H12  SING  N  N  58  
8AO  C62  H13  SING  N  N  59  
8AO  C61  H14  SING  N  N  60  
8AO  C60  H15  SING  N  N  61  
8AO  C59  H16  SING  N  N  62  
8AO  C58  H17  SING  N  N  63  
8AO  C40  H18  SING  N  N  64  
8AO  C39  H19  SING  N  N  65  
8AO  C42  H20  SING  N  N  66  
8AO  C43  H21  SING  N  N  67  
8AO  C34  H22  SING  N  N  68  
8AO  C34  H23  SING  N  N  69  
8AO  C34  H24  SING  N  N  70  
8AO  N7   H25  SING  N  N  71  
8AO  N7   H26  SING  N  N  72  
8AO  N54  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
8AO  InChI             InChI                 1.03   "InChI=1S/C31H27F3N4O3S/c1-18(2)30(26(16-35)28(36)41-29-27(30)19(3)37-38-29)23-13-22(14-24(15-23)31(32,33)34)21-9-11-25(12-10-21)42(39,40)17-20-7-5-4-6-8-20/h4-15,18H,17,36H2,1-3H3,(H,37,38)/t30-/m0/s1"  
8AO  InChIKey          InChI                 1.03   PGTUNNBRJSLXTJ-PMERELPUSA-N  
8AO  SMILES_CANONICAL  CACTVS                3.385  "CC(C)[C@]1(c2cc(cc(c2)C(F)(F)F)c3ccc(cc3)[S](=O)(=O)Cc4ccccc4)C(=C(N)Oc5n[nH]c(C)c15)C#N"  
8AO  SMILES            CACTVS                3.385  "CC(C)[C]1(c2cc(cc(c2)C(F)(F)F)c3ccc(cc3)[S](=O)(=O)Cc4ccccc4)C(=C(N)Oc5n[nH]c(C)c15)C#N"  
8AO  SMILES_CANONICAL  "OpenEye OEToolkits"  2.0.6  "Cc1c2c(n[nH]1)OC(=C([C@@]2(c3cc(cc(c3)C(F)(F)F)c4ccc(cc4)S(=O)(=O)Cc5ccccc5)C(C)C)C#N)N"  
8AO  SMILES            "OpenEye OEToolkits"  2.0.6  "Cc1c2c(n[nH]1)OC(=C(C2(c3cc(cc(c3)C(F)(F)F)c4ccc(cc4)S(=O)(=O)Cc5ccccc5)C(C)C)C#N)N"  
#
_pdbx_chem_comp_identifier.comp_id          8AO
_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-3-methyl-4-[3-[4-(phenylmethyl)sulfonylphenyl]-5-(trifluoromethyl)phenyl]-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
8AO  "Create component"  2017-05-25  PDBJ  
8AO  "Initial release"   2017-11-29  RCSB  
8AO  "Modify synonyms"   2020-06-05  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     8AO
_pdbx_chem_comp_synonyms.name        "(S)-6-amino-4-(4'-(benzylsulfonyl)-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        ?
##
