data_8UO
# 
_chem_comp.id                                    8UO 
_chem_comp.name                                  "2-[1-[3-[(4~{S})-6-azanyl-5-cyano-3-methyl-4-propan-2-yl-2~{H}-pyrano[2,3-c]pyrazol-4-yl]-5-fluoranyl-phenyl]piperidin-4-yl]ethanoic acid" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C24 H28 F N5 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2017-09-26 
_chem_comp.pdbx_modified_date                    2018-06-01 
_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                        453.509 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     8UO 
_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        5YFZ 
_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 
8UO C4  C1  C 0 1 N N S 20.782 14.339 97.093  2.745  0.161  0.204  C4  8UO 1  
8UO C14 C2  C 0 1 N N N 22.111 14.948 97.660  3.868  1.115  0.616  C14 8UO 2  
8UO C5  C3  C 0 1 Y N N 21.045 13.926 95.684  3.060  -0.446 -1.139 C5  8UO 3  
8UO C6  C4  C 0 1 Y N N 21.315 12.549 95.281  3.448  -1.796 -1.284 C6  8UO 4  
8UO C8  C5  C 0 1 N N N 20.040 13.327 99.126  2.082  -0.663 2.499  C8  8UO 5  
8UO C13 C6  C 0 1 N N N 20.947 16.119 94.096  2.682  1.544  -2.673 C13 8UO 6  
8UO C15 C7  C 0 1 N N N 22.511 16.322 97.089  3.601  1.637  2.029  C15 8UO 7  
8UO C16 C8  C 0 1 Y N N 19.561 15.272 97.139  1.441  0.911  0.130  C16 8UO 8  
8UO C20 C9  C 0 1 Y N N 18.450 15.194 96.249  0.261  0.224  -0.085 C20 8UO 9  
8UO C19 C10 C 0 1 Y N N 17.345 16.076 96.340  -0.942 0.916  -0.153 C19 8UO 10 
8UO C18 C11 C 0 1 Y N N 18.434 17.109 98.233  0.228  2.979  0.210  C18 8UO 11 
8UO N11 N1  N 0 1 Y N N 21.408 13.712 93.460  3.402  -0.834 -3.252 N11 8UO 12 
8UO C2  C12 C 0 1 N N N 20.770 11.844 97.543  3.028  -2.221 0.953  C2  8UO 13 
8UO N7  N2  N 0 1 N N N 20.559 10.766 98.297  2.880  -3.152 1.951  N7  8UO 14 
8UO C3  C13 C 0 1 N N N 20.497 13.112 97.961  2.633  -0.957 1.211  C3  8UO 15 
8UO O1  O1  O 0 1 N N N 21.316 11.566 96.226  3.557  -2.634 -0.218 O1  8UO 16 
8UO C10 C14 C 0 1 Y N N 21.134 14.653 94.387  3.041  0.115  -2.358 C10 8UO 17 
8UO O33 O2  O 0 1 N N N 13.570 16.887 91.127  -7.146 0.480  0.235  O33 8UO 18 
8UO C31 C15 C 0 1 N N N 12.566 16.714 91.865  -7.245 -0.675 -0.105 C31 8UO 19 
8UO O32 O3  O 0 1 N N N 11.458 17.258 91.639  -8.448 -1.179 -0.424 O32 8UO 20 
8UO C29 C16 C 0 1 N N N 12.680 15.807 93.078  -6.020 -1.549 -0.172 C29 8UO 21 
8UO C26 C17 C 0 1 N N N 13.954 16.098 93.884  -4.790 -0.736 0.238  C26 8UO 22 
8UO C25 C18 C 0 1 N N N 13.756 15.768 95.343  -3.565 -1.653 0.291  C25 8UO 23 
8UO C24 C19 C 0 1 N N N 14.904 16.353 96.155  -2.328 -0.823 0.642  C24 8UO 24 
8UO C27 C20 C 0 1 N N N 15.160 15.348 93.364  -4.544 0.373  -0.789 C27 8UO 25 
8UO C28 C21 C 0 1 N N N 16.429 15.898 94.025  -3.279 1.144  -0.406 C28 8UO 26 
8UO N23 N3  N 0 1 N N N 16.208 16.065 95.479  -2.135 0.223  -0.370 N23 8UO 27 
8UO C30 C22 C 0 1 Y N N 17.370 17.034 97.358  -0.956 2.296  -0.005 C30 8UO 28 
8UO F21 F1  F 0 1 N N N 18.450 18.019 99.202  0.217  4.322  0.354  F21 8UO 29 
8UO C17 C23 C 0 1 Y N N 19.506 16.255 98.134  1.425  2.285  0.283  C17 8UO 30 
8UO C22 C24 C 0 1 N N N 23.347 14.017 97.629  5.205  0.372  0.590  C22 8UO 31 
8UO N9  N4  N 0 1 N N N 19.622 13.519 100.196 1.645  -0.430 3.521  N9  8UO 32 
8UO N12 N5  N 0 1 Y N N 21.526 12.400 93.962  3.652  -2.023 -2.549 N12 8UO 33 
8UO H1  H1  H 0 1 N N N 21.910 15.125 98.727  3.905  1.954  -0.080 H1  8UO 34 
8UO H2  H2  H 0 1 N N N 19.888 16.317 93.876  1.611  1.617  -2.859 H2  8UO 35 
8UO H3  H3  H 0 1 N N N 21.256 16.709 94.971  2.949  2.181  -1.829 H3  8UO 36 
8UO H4  H4  H 0 1 N N N 21.561 16.402 93.228  3.228  1.869  -3.559 H4  8UO 37 
8UO H5  H5  H 0 1 N N N 23.452 16.653 97.553  3.704  0.820  2.743  H5  8UO 38 
8UO H6  H6  H 0 1 N N N 22.648 16.241 96.001  4.319  2.421  2.269  H6  8UO 39 
8UO H7  H7  H 0 1 N N N 21.719 17.054 97.305  2.590  2.041  2.083  H7  8UO 40 
8UO H8  H8  H 0 1 N N N 18.451 14.437 95.479  0.275  -0.849 -0.200 H8  8UO 41 
8UO H9  H9  H 0 1 N N N 21.519 13.929 92.490  3.476  -0.713 -4.212 H9  8UO 42 
8UO H10 H10 H 0 1 N N N 20.827 9.947  97.791  2.503  -2.891 2.806  H10 8UO 43 
8UO H11 H11 H 0 1 N N N 21.102 10.833 99.134  3.153  -4.071 1.801  H11 8UO 44 
8UO H12 H12 H 0 1 N N N 11.520 17.790 90.855  -9.204 -0.580 -0.366 H12 8UO 45 
8UO H13 H13 H 0 1 N N N 11.805 15.965 93.725  -6.139 -2.394 0.506  H13 8UO 46 
8UO H14 H14 H 0 1 N N N 12.703 14.760 92.740  -5.890 -1.915 -1.191 H14 8UO 47 
8UO H15 H15 H 0 1 N N N 14.163 17.175 93.803  -4.957 -0.294 1.220  H15 8UO 48 
8UO H16 H16 H 0 1 N N N 12.805 16.197 95.690  -3.717 -2.419 1.051  H16 8UO 49 
8UO H17 H17 H 0 1 N N N 13.734 14.676 95.472  -3.422 -2.126 -0.680 H17 8UO 50 
8UO H18 H18 H 0 1 N N N 14.771 17.442 96.242  -2.466 -0.361 1.620  H18 8UO 51 
8UO H19 H19 H 0 1 N N N 14.907 15.903 97.159  -1.451 -1.470 0.667  H19 8UO 52 
8UO H20 H20 H 0 1 N N N 15.057 14.279 93.601  -4.417 -0.068 -1.777 H20 8UO 53 
8UO H21 H21 H 0 1 N N N 15.229 15.477 92.274  -5.395 1.054  -0.800 H21 8UO 54 
8UO H22 H22 H 0 1 N N N 17.260 15.196 93.861  -3.092 1.925  -1.143 H22 8UO 55 
8UO H23 H23 H 0 1 N N N 16.679 16.872 93.580  -3.412 1.596  0.576  H23 8UO 56 
8UO H24 H24 H 0 1 N N N 16.546 17.724 97.461  -1.889 2.837  -0.058 H24 8UO 57 
8UO H25 H25 H 0 1 N N N 20.321 16.344 98.837  2.348  2.818  0.456  H25 8UO 58 
8UO H26 H26 H 0 1 N N N 23.075 13.031 98.035  5.395  0.001  -0.417 H26 8UO 59 
8UO H27 H27 H 0 1 N N N 23.694 13.903 96.591  6.004  1.053  0.884  H27 8UO 60 
8UO H28 H28 H 0 1 N N N 24.151 14.455 98.239  5.168  -0.466 1.286  H28 8UO 61 
# 
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 
8UO O33 C31 DOUB N N 1  
8UO O32 C31 SING N N 2  
8UO C31 C29 SING N N 3  
8UO C29 C26 SING N N 4  
8UO C27 C26 SING N N 5  
8UO C27 C28 SING N N 6  
8UO N11 N12 SING Y N 7  
8UO N11 C10 SING Y N 8  
8UO C26 C25 SING N N 9  
8UO N12 C6  DOUB Y N 10 
8UO C28 N23 SING N N 11 
8UO C13 C10 SING N N 12 
8UO C10 C5  DOUB Y N 13 
8UO C6  C5  SING Y N 14 
8UO C6  O1  SING N N 15 
8UO C25 C24 SING N N 16 
8UO N23 C24 SING N N 17 
8UO N23 C19 SING N N 18 
8UO C5  C4  SING N N 19 
8UO O1  C2  SING N N 20 
8UO C20 C19 DOUB Y N 21 
8UO C20 C16 SING Y N 22 
8UO C19 C30 SING Y N 23 
8UO C15 C14 SING N N 24 
8UO C4  C16 SING N N 25 
8UO C4  C14 SING N N 26 
8UO C4  C3  SING N N 27 
8UO C16 C17 DOUB Y N 28 
8UO C30 C18 DOUB Y N 29 
8UO C2  C3  DOUB N N 30 
8UO C2  N7  SING N N 31 
8UO C22 C14 SING N N 32 
8UO C3  C8  SING N N 33 
8UO C17 C18 SING Y N 34 
8UO C18 F21 SING N N 35 
8UO C8  N9  TRIP N N 36 
8UO C14 H1  SING N N 37 
8UO C13 H2  SING N N 38 
8UO C13 H3  SING N N 39 
8UO C13 H4  SING N N 40 
8UO C15 H5  SING N N 41 
8UO C15 H6  SING N N 42 
8UO C15 H7  SING N N 43 
8UO C20 H8  SING N N 44 
8UO N11 H9  SING N N 45 
8UO N7  H10 SING N N 46 
8UO N7  H11 SING N N 47 
8UO O32 H12 SING N N 48 
8UO C29 H13 SING N N 49 
8UO C29 H14 SING N N 50 
8UO C26 H15 SING N N 51 
8UO C25 H16 SING N N 52 
8UO C25 H17 SING N N 53 
8UO C24 H18 SING N N 54 
8UO C24 H19 SING N N 55 
8UO C27 H20 SING N N 56 
8UO C27 H21 SING N N 57 
8UO C28 H22 SING N N 58 
8UO C28 H23 SING N N 59 
8UO C30 H24 SING N N 60 
8UO C17 H25 SING N N 61 
8UO C22 H26 SING N N 62 
8UO C22 H27 SING N N 63 
8UO C22 H28 SING N N 64 
# 
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 
8UO InChI            InChI                1.03  "InChI=1S/C24H28FN5O3/c1-13(2)24(19(12-26)22(27)33-23-21(24)14(3)28-29-23)16-9-17(25)11-18(10-16)30-6-4-15(5-7-30)8-20(31)32/h9-11,13,15H,4-8,27H2,1-3H3,(H,28,29)(H,31,32)/t24-/m0/s1" 
8UO InChIKey         InChI                1.03  LNTOYLXMWSSXMA-DEOSSOPVSA-N                                                                                                                                                             
8UO SMILES_CANONICAL CACTVS               3.385 "CC(C)[C@]1(c2cc(F)cc(c2)N3CCC(CC3)CC(O)=O)C(=C(N)Oc4n[nH]c(C)c14)C#N"                                                                                                                  
8UO SMILES           CACTVS               3.385 "CC(C)[C]1(c2cc(F)cc(c2)N3CCC(CC3)CC(O)=O)C(=C(N)Oc4n[nH]c(C)c14)C#N"                                                                                                                   
8UO SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "Cc1c2c(n[nH]1)OC(=C([C@@]2(c3cc(cc(c3)F)N4CCC(CC4)CC(=O)O)C(C)C)C#N)N"                                                                                                                 
8UO SMILES           "OpenEye OEToolkits" 2.0.6 "Cc1c2c(n[nH]1)OC(=C(C2(c3cc(cc(c3)F)N4CCC(CC4)CC(=O)O)C(C)C)C#N)N"                                                                                                                     
# 
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 
8UO "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.6 "2-[1-[3-[(4~{S})-6-azanyl-5-cyano-3-methyl-4-propan-2-yl-2~{H}-pyrano[2,3-c]pyrazol-4-yl]-5-fluoranyl-phenyl]piperidin-4-yl]ethanoic acid" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
8UO "Create component" 2017-09-26 RCSB 
8UO "Initial release"  2018-06-06 RCSB 
# 
