data_KES
#

_chem_comp.id                                   KES
_chem_comp.name                                 "N-{5-[5-chloro-2-(difluoromethoxy)phenyl]-1H-pyrazol-4-yl}pyrazolo[1,5-a]pyrimidine-3-carboxamide"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C17 H11 Cl F2 N6 O2"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        ?
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2018-11-29
_chem_comp.pdbx_modified_date                   2019-04-19
_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                       404.758
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    KES
_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       6N79
_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
KES  C4   C1   C   0  1  Y  N  N  22.237  199.015  17.749   2.428   1.323   0.938  C4   KES   1  
KES  C14  C2   C   0  1  Y  N  N  19.019  192.556  16.091  -3.263   1.573  -0.208  C14  KES   2  
KES  C5   C3   C   0  1  Y  N  N  20.520  198.829  14.726   5.968   1.514   1.082  C5   KES   3  
KES  C6   C4   C   0  1  N  N  N  22.200  196.622  18.779   1.938  -0.970  -0.104  C6   KES   4  
KES  C11  C5   C   0  1  Y  N  N  21.214  191.326  17.274  -3.320  -0.896   1.064  C11  KES   5  
KES  C7   C6   C   0  1  Y  N  N  21.740  194.285  19.405  -0.247  -1.826  -0.521  C7   KES   6  
KES  C8   C7   C   0  1  Y  N  N  22.159  194.249  20.766   0.154  -3.051  -1.067  C8   KES   7  
KES  C9   C8   C   0  1  Y  N  N  21.299  192.973  19.108  -1.628  -1.801  -0.524  C9   KES   8  
KES  C10  C9   C   0  1  Y  N  N  20.677  192.472  17.864  -2.488  -0.702  -0.039  C10  KES   9  
KES  C12  C10  C   0  1  Y  N  N  20.645  190.816  16.127  -4.121   0.135   1.512  C12  KES  10  
KES  C13  C11  C   0  1  Y  N  N  19.565  191.420  15.521  -4.088   1.368   0.882  C13  KES  11  
KES  N1   N1   N   0  1  Y  N  N  21.770  199.652  16.684   3.497   2.000   1.264  N1   KES  12  
KES  N2   N2   N   0  1  Y  N  N  21.219  198.663  15.902   4.637   1.255   0.943  N2   KES  13  
KES  C3   C12  C   0  1  Y  N  N  22.006  197.632  17.701   2.823   0.091   0.388  C3   KES  14  
KES  N3   N3   N   0  1  N  N  N  21.777  195.351  18.475   0.601  -0.810  -0.051  N3   KES  15  
KES  CL   CL1  CL  0  0  N  N  N  21.281  189.347  15.452  -5.157  -0.107   2.884  CL   KES  16  
KES  C15  C13  C   0  1  Y  N  N  19.563  193.075  17.256  -2.463   0.544  -0.677  C15  KES  17  
KES  O1   O1   O   0  1  N  N  N  19.072  194.210  17.857  -1.656   0.744  -1.752  O1   KES  18  
KES  C16  C14  C   0  1  N  N  N  17.810  194.191  18.317  -1.683   2.041  -2.351  C16  KES  19  
KES  F1   F1   F   0  1  N  N  N  17.801  194.544  19.587  -2.979   2.321  -2.797  F1   KES  20  
KES  F    F2   F   0  1  N  N  N  16.918  194.724  17.474  -1.296   2.999  -1.408  F    KES  21  
KES  N5   N4   N   0  1  Y  N  N  21.475  192.204  20.189  -2.049  -2.986  -1.060  N5   KES  22  
KES  N4   N5   N   0  1  Y  N  N  21.984  192.988  21.165  -0.914  -3.737  -1.386  N4   KES  23  
KES  O    O2   O   0  1  N  N  N  22.660  196.943  19.876   2.411  -1.995  -0.559  O    KES  24  
KES  C    C15  C   0  1  Y  N  N  20.005  197.726  14.140   6.869   0.584   0.673  C    KES  25  
KES  C2   C16  C   0  1  Y  N  N  21.382  197.422  16.463   4.231   0.071   0.396  C2   KES  26  
KES  N    N6   N   0  1  Y  N  N  20.915  196.285  15.874   5.121  -0.837  -0.004  N    KES  27  
KES  C1   C17  C   0  1  Y  N  N  20.245  196.463  14.741   6.412  -0.616   0.118  C1   KES  28  
KES  H1   H1   H   0  1  N  N  N  22.742  199.508  18.567   1.408   1.654   1.072  H1   KES  29  
KES  H2   H2   H   0  1  N  N  N  18.170  193.038  15.629  -3.246   2.535  -0.698  H2   KES  30  
KES  H3   H3   H   0  1  N  N  N  20.388  199.807  14.288   6.302   2.446   1.513  H3   KES  31  
KES  H4   H4   H   0  1  N  N  N  22.072  190.841  17.715  -3.338  -1.852   1.566  H4   KES  32  
KES  H5   H5   H   0  1  N  N  N  22.539  195.072  21.353   1.175  -3.376  -1.203  H5   KES  33  
KES  H6   H6   H   0  1  N  N  N  19.150  191.011  14.612  -4.711   2.173   1.243  H6   KES  34  
KES  H7   H7   H   0  1  N  N  N  21.477  195.168  17.539   0.224   0.007   0.312  H7   KES  35  
KES  H8   H8   H   0  1  N  N  N  17.552  193.122  18.334  -0.995   2.065  -3.197  H8   KES  36  
KES  H9   H9   H   0  1  N  N  N  21.268  191.228  20.261  -2.971  -3.258  -1.191  H9   KES  37  
KES  H10  H10  H   0  1  N  N  N  19.423  197.804  13.234   7.928   0.770   0.775  H10  KES  38  
KES  H11  H11  H   0  1  N  N  N  19.856  195.587  14.243   7.120  -1.362  -0.211  H11  KES  39  
#   #
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
KES  C    C5   DOUB  Y  N   1  
KES  C    C1   SING  Y  N   2  
KES  C5   N2   SING  Y  N   3  
KES  C1   N    DOUB  Y  N   4  
KES  CL   C12  SING  N  N   5  
KES  C13  C14  DOUB  Y  N   6  
KES  C13  C12  SING  Y  N   7  
KES  N    C2   SING  Y  N   8  
KES  N2   C2   SING  Y  N   9  
KES  N2   N1   SING  Y  N  10  
KES  C14  C15  SING  Y  N  11  
KES  C12  C11  DOUB  Y  N  12  
KES  C2   C3   DOUB  Y  N  13  
KES  N1   C4   DOUB  Y  N  14  
KES  C15  O1   SING  N  N  15  
KES  C15  C10  DOUB  Y  N  16  
KES  C11  C10  SING  Y  N  17  
KES  F    C16  SING  N  N  18  
KES  C3   C4   SING  Y  N  19  
KES  C3   C6   SING  N  N  20  
KES  O1   C16  SING  N  N  21  
KES  C10  C9   SING  N  N  22  
KES  C16  F1   SING  N  N  23  
KES  N3   C6   SING  N  N  24  
KES  N3   C7   SING  N  N  25  
KES  C6   O    DOUB  N  N  26  
KES  C9   C7   DOUB  Y  N  27  
KES  C9   N5   SING  Y  N  28  
KES  C7   C8   SING  Y  N  29  
KES  N5   N4   SING  Y  N  30  
KES  C8   N4   DOUB  Y  N  31  
KES  C4   H1   SING  N  N  32  
KES  C14  H2   SING  N  N  33  
KES  C5   H3   SING  N  N  34  
KES  C11  H4   SING  N  N  35  
KES  C8   H5   SING  N  N  36  
KES  C13  H6   SING  N  N  37  
KES  N3   H7   SING  N  N  38  
KES  C16  H8   SING  N  N  39  
KES  N5   H9   SING  N  N  40  
KES  C    H10  SING  N  N  41  
KES  C1   H11  SING  N  N  42  
#   #
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
KES  SMILES            ACDLabs               12.01  "c2nn1cccnc1c2C(=O)Nc3cnnc3c4cc(ccc4OC(F)F)Cl"  
KES  InChI             InChI                 1.03   "InChI=1S/C17H11ClF2N6O2/c18-9-2-3-13(28-17(19)20)10(6-9)14-12(8-22-25-14)24-16(27)11-7-23-26-5-1-4-21-15(11)26/h1-8,17H,(H,22,25)(H,24,27)"  
KES  InChIKey          InChI                 1.03   KHCFKCPXXJQHMH-UHFFFAOYSA-N  
KES  SMILES_CANONICAL  CACTVS                3.385  "FC(F)Oc1ccc(Cl)cc1c2[nH]ncc2NC(=O)c3cnn4cccnc34"  
KES  SMILES            CACTVS                3.385  "FC(F)Oc1ccc(Cl)cc1c2[nH]ncc2NC(=O)c3cnn4cccnc34"  
KES  SMILES_CANONICAL  "OpenEye OEToolkits"  2.0.6  "c1cnc2c(cnn2c1)C(=O)Nc3cn[nH]c3c4cc(ccc4OC(F)F)Cl"  
KES  SMILES            "OpenEye OEToolkits"  2.0.6  "c1cnc2c(cnn2c1)C(=O)Nc3cn[nH]c3c4cc(ccc4OC(F)F)Cl"  
#   #
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
KES  "SYSTEMATIC NAME"  ACDLabs               12.01  "N-{5-[5-chloro-2-(difluoromethoxy)phenyl]-1H-pyrazol-4-yl}pyrazolo[1,5-a]pyrimidine-3-carboxamide"  
KES  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  2.0.6  "~{N}-[5-[2-[bis(fluoranyl)methoxy]-5-chloranyl-phenyl]-1~{H}-pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
KES  "Create component"  2018-11-29  RCSB  
KES  "Initial release"   2019-04-24  RCSB  
##
