# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Apr 29 21:58:11 2020
#   Inital geometry file: a 151 line input string
#   Ligand 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
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)[C@]1(c2cc(F)cc(c2)N3CCC(CC3)CC(O)=O)C(=C(N)Oc4n[nH]c(C)c14)C#N
#
data_comp_list
loop_
_chem_comp.id
_chem_comp.three_letter_code
_chem_comp.name
_chem_comp.group
_chem_comp.number_atoms_all
_chem_comp.number_atoms_nh
_chem_comp.desc_level
_chem_comp.initial_date
_chem_comp.modified_date
_chem_comp.source
 8UO  8UO  '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'  ligand  61  33  .  2022-07-24  2022-11-17
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_8UO
loop_
_chem_comp_atom.comp_id
_chem_comp_atom.atom_id
_chem_comp_atom.type_symbol
_chem_comp_atom.type_energy
_chem_comp_atom.charge
_chem_comp_atom.partial_charge
_chem_comp_atom.x
_chem_comp_atom.y
_chem_comp_atom.z
 8UO  C4   C  CT    0  -0.168   2.7128   0.2508   0.2884
 8UO  C14  C  CH1   0  -0.211   4.0050   1.0370   0.6631
 8UO  C5   C  CR5   0  -0.146   2.8722  -0.3672  -1.0686
 8UO  C6   C  CR5   0   0.457   3.0825  -1.7276  -1.2598
 8UO  C8   C  CSP   0   0.036   1.9521  -0.6735   2.5158
 8UO  C15  C  CH3   0  -0.677   3.9821   1.6204   2.0749
 8UO  C16  C  CR6   0   0.207   1.4595   1.1367   0.2574
 8UO  C20  C  CR16  0  -0.381   0.2200   0.5173   0.2017
 8UO  C19  C  CR6   0   0.418  -0.9793   1.2382   0.1172
 8UO  C18  C  CR6   0   0.599   0.3435   3.2269   0.1009
 8UO  N11  N  NR15  0  -0.493   3.1160  -0.9182  -3.1568
 8UO  C2   C  C     0   0.604   2.7682  -2.2352   0.9490
 8UO  N7   N  NH2   0  -0.836   2.7387  -3.2551   1.8173
 8UO  C3   C  C     0  -0.219   2.4908  -0.9233   1.2411
 8UO  O1   O  O2    0  -0.454   3.1404  -2.6522  -0.2717
 8UO  C10  C  CR5   0   0.364   2.8989   0.1403  -2.3555
 8UO  O33  O  O     0  -0.444  -7.6205  -0.1036   0.2374
 8UO  C31  C  C     0   0.550  -7.2472  -1.0851  -0.3565
 8UO  O32  O  OH1   0  -0.596  -8.0479  -1.8017  -1.1400
 8UO  C29  C  CH2   0  -0.577  -5.8646  -1.6729  -0.2801
 8UO  C26  C  CH1   0  -0.245  -4.8014  -0.7180   0.2433
 8UO  C25  C  CH2   0  -0.421  -3.4993  -1.4656   0.5088
 8UO  C24  C  CH2   0  -0.302  -2.4156  -0.5224   0.9981
 8UO  C27  C  CH2   0  -0.419  -4.5146   0.4270  -0.7223
 8UO  C28  C  CH2   0  -0.307  -3.3956   1.3280  -0.2182
 8UO  N23  N  NT    0  -0.518  -2.1917   0.5645   0.0505
 8UO  C30  C  CR16  0  -0.563  -0.9013   2.6356   0.0705
 8UO  F21  F  F     0  -0.324   0.4031   4.5711   0.0516
 8UO  C17  C  CR16  0  -0.556   1.5274   2.5275   0.1997
 8UO  C22  C  CH3   0  -0.662   5.2637   0.1923   0.4983
 8UO  N9   N  NS    0  -0.290   1.4901  -0.4958   3.5630
 8UO  N12  N  N     0  -0.296   3.2307  -2.0817  -2.5094
 8UO  H1   H  HCH1  0   0.232   4.0834   1.8615  -0.0534
 8UO  H2   H  HCH3  0   0.264   1.7254   1.8937  -2.6599
 8UO  H3   H  HCH3  0   0.259   3.4376   2.2061  -2.4231
 8UO  H4   H  HCH3  0   0.266   2.8713   1.5533  -3.9581
 8UO  H5   H  HCH3  0   0.229   4.1419   0.8440   2.8248
 8UO  H6   H  HCH3  0   0.240   4.7903   2.3448   2.1865
 8UO  H7   H  HCH3  0   0.238   3.0511   2.1319   2.3174
 8UO  H8   H  HCR6  0   0.255   0.1866  -0.5640   0.1934
 8UO  H9   H  HNR5  0   0.421   3.1893  -0.9045  -4.1617
 8UO  H10  H  HNH2  0   0.419   2.4264  -3.1011   2.7614
 8UO  H11  H  HNH2  0   0.415   2.6357  -4.1950   1.4695
 8UO  H12  H  HOH1  0   0.478  -8.9401  -1.4232  -1.1352
 8UO  H13  H  HCH2  0   0.291  -5.9338  -2.5451   0.3812
 8UO  H14  H  HCH2  0   0.268  -5.5796  -2.0682  -1.2591
 8UO  H15  H  HCH1  0   0.230  -5.1461  -0.2930   1.1933
 8UO  H16  H  HCH2  0   0.240  -3.6512  -2.2458   1.2587
 8UO  H17  H  HCH2  0   0.222  -3.1598  -1.9594  -0.4075
 8UO  H18  H  HCH2  0   0.217  -2.7016  -0.1134   1.9792
 8UO  H19  H  HCH2  0   0.254  -1.4943  -1.0796   1.1492
 8UO  H20  H  HCH2  0   0.220  -4.2304   0.0179  -1.6976
 8UO  H21  H  HCH2  0   0.243  -5.4028   1.0421  -0.8782
 8UO  H22  H  HCH2  0   0.253  -3.1849   2.0758  -0.9829
 8UO  H23  H  HCH2  0   0.212  -3.7374   1.8679   0.6789
 8UO  H24  H  HCR6  0   0.284  -1.7793   3.2645   0.0306
 8UO  H25  H  HCR6  0   0.270   2.4581   3.0758   0.2278
 8UO  H26  H  HCH3  0   0.237   5.4067  -0.1528  -0.5250
 8UO  H27  H  HCH3  0   0.237   6.1403   0.7841   0.7660
 8UO  H28  H  HCH3  0   0.222   5.2498  -0.6785   1.1573
 8UO  C13  C  CH3   0  -0.746   2.7254   1.5190  -2.8791

loop_
_chem_comp_bond.comp_id
_chem_comp_bond.atom_id_1
_chem_comp_bond.atom_id_2
_chem_comp_bond.type
_chem_comp_bond.value_dist
_chem_comp_bond.value_dist_esd
_chem_comp_bond.value_dist_neutron
 8UO  O33  C31  double    1.206  0.020  1.206
 8UO  O32  C31  single    1.330  0.020  1.330
 8UO  C31  C29  single    1.504  0.020  1.504
 8UO  C29  C26  single    1.522  0.020  1.522
 8UO  C27  C26  single    1.525  0.020  1.525
 8UO  C27  C28  single    1.523  0.020  1.523
 8UO  N11  N12  aromatic  1.336  0.020  1.336
 8UO  N11  C10  aromatic  1.345  0.020  1.345
 8UO  C26  C25  single    1.525  0.020  1.525
 8UO  N12  C6   aromatic  1.307  0.020  1.307
 8UO  C28  N23  single    1.451  0.020  1.451
 8UO  C13  C10  single    1.485  0.020  1.485
 8UO  C10  C5   aromatic  1.384  0.020  1.384
 8UO  C6   C5   aromatic  1.390  0.020  1.390
 8UO  C6   O1   single    1.354  0.020  1.354
 8UO  C25  C24  single    1.518  0.020  1.518
 8UO  N23  C24  single    1.459  0.020  1.459
 8UO  N23  C19  single    1.389  0.020  1.389
 8UO  C5   C4   single    1.500  0.020  1.500
 8UO  O1   C2   single    1.343  0.020  1.343
 8UO  C20  C19  aromatic  1.402  0.020  1.402
 8UO  C20  C16  aromatic  1.387  0.020  1.387
 8UO  C19  C30  aromatic  1.400  0.020  1.400
 8UO  C15  C14  single    1.528  0.020  1.528
 8UO  C4   C16  single    1.535  0.020  1.535
 8UO  C4   C14  single    1.558  0.020  1.558
 8UO  C4   C3   single    1.528  0.020  1.528
 8UO  C16  C17  aromatic  1.394  0.020  1.394
 8UO  C30  C18  aromatic  1.378  0.020  1.378
 8UO  C2   C3   double    1.372  0.020  1.372
 8UO  C2   N7   single    1.340  0.020  1.340
 8UO  C22  C14  single    1.525  0.020  1.525
 8UO  C3   C8   single    1.406  0.020  1.406
 8UO  C17  C18  aromatic  1.379  0.020  1.379
 8UO  C18  F21  single    1.346  0.020  1.346
 8UO  C8   N9   triple    1.158  0.020  1.158
 8UO  C14  H1   single    0.970  0.020  1.090
 8UO  C13  H2   single    0.970  0.020  1.090
 8UO  C13  H3   single    0.970  0.020  1.090
 8UO  C13  H4   single    0.970  0.020  1.090
 8UO  C15  H5   single    0.970  0.020  1.090
 8UO  C15  H6   single    0.970  0.020  1.090
 8UO  C15  H7   single    0.970  0.020  1.090
 8UO  C20  H8   single    0.930  0.020  1.080
 8UO  N11  H9   single    0.860  0.020  1.020
 8UO  N7   H10  single    0.890  0.020  1.040
 8UO  N7   H11  single    0.890  0.020  1.040
 8UO  O32  H12  single    0.850  0.020  0.980
 8UO  C29  H13  single    0.970  0.020  1.090
 8UO  C29  H14  single    0.970  0.020  1.090
 8UO  C26  H15  single    0.970  0.020  1.090
 8UO  C25  H16  single    0.970  0.020  1.090
 8UO  C25  H17  single    0.970  0.020  1.090
 8UO  C24  H18  single    0.970  0.020  1.090
 8UO  C24  H19  single    0.970  0.020  1.090
 8UO  C27  H20  single    0.970  0.020  1.090
 8UO  C27  H21  single    0.970  0.020  1.090
 8UO  C28  H22  single    0.970  0.020  1.090
 8UO  C28  H23  single    0.970  0.020  1.090
 8UO  C30  H24  single    0.930  0.020  1.080
 8UO  C17  H25  single    0.930  0.020  1.080
 8UO  C22  H26  single    0.970  0.020  1.090
 8UO  C22  H27  single    0.970  0.020  1.090
 8UO  C22  H28  single    0.970  0.020  1.090

loop_
_chem_comp_angle.comp_id
_chem_comp_angle.atom_id_1
_chem_comp_angle.atom_id_2
_chem_comp_angle.atom_id_3
_chem_comp_angle.value_angle
_chem_comp_angle.value_angle_esd
 8UO  C3   C4   C16  109.72  3.000
 8UO  C3   C4   C5   105.25  3.000
 8UO  C16  C4   C5   107.84  3.000
 8UO  C3   C4   C14  110.99  3.000
 8UO  C16  C4   C14  113.00  3.000
 8UO  C5   C4   C14  109.71  3.000
 8UO  H1   C14  C22  106.70  3.000
 8UO  H1   C14  C15  108.55  3.000
 8UO  C22  C14  C15  108.89  3.000
 8UO  H1   C14  C4   106.37  3.000
 8UO  C22  C14  C4   112.28  3.000
 8UO  C15  C14  C4   113.73  3.000
 8UO  C10  C5   C6   103.19  3.000
 8UO  C6   C5   C4   122.95  3.000
 8UO  C10  C5   C4   133.83  3.000
 8UO  N12  C6   O1   120.51  3.000
 8UO  O1   C6   C5   125.05  3.000
 8UO  N12  C6   C5   114.44  3.000
 8UO  N9   C8   C3   180.00  3.000
 8UO  H7   C15  H6   107.37  3.000
 8UO  H7   C15  H5   107.83  3.000
 8UO  H6   C15  H5   107.08  3.000
 8UO  H7   C15  C14  113.44  3.000
 8UO  H6   C15  C14  109.69  3.000
 8UO  H5   C15  C14  111.17  3.000
 8UO  C17  C16  C20  119.18  3.000
 8UO  C17  C16  C4   122.48  3.000
 8UO  C20  C16  C4   118.21  3.000
 8UO  H8   C20  C19  119.16  3.000
 8UO  H8   C20  C16  118.31  3.000
 8UO  C19  C20  C16  122.51  3.000
 8UO  C30  C19  N23  122.08  3.000
 8UO  C30  C19  C20  117.88  3.000
 8UO  N23  C19  C20  120.02  3.000
 8UO  C17  C18  F21  118.10  3.000
 8UO  F21  C18  C30  117.86  3.000
 8UO  C17  C18  C30  124.03  3.000
 8UO  H9   N11  N12  119.26  3.000
 8UO  H9   N11  C10  126.52  3.000
 8UO  N12  N11  C10  114.22  3.000
 8UO  O1   C2   C3   123.13  3.000
 8UO  C3   C2   N7   125.82  3.000
 8UO  O1   C2   N7   111.03  3.000
 8UO  H11  N7   H10  115.78  3.000
 8UO  H11  N7   C2   119.25  3.000
 8UO  H10  N7   C2   119.89  3.000
 8UO  C2   C3   C8   116.12  3.000
 8UO  C8   C3   C4   118.96  3.000
 8UO  C2   C3   C4   124.92  3.000
 8UO  C2   O1   C6   116.07  3.000
 8UO  N11  C10  C13  122.64  3.000
 8UO  C13  C10  C5   131.78  3.000
 8UO  N11  C10  C5   105.58  3.000
 8UO  C29  C31  O32  111.88  3.000
 8UO  C29  C31  O33  125.26  3.000
 8UO  O32  C31  O33  122.83  3.000
 8UO  H12  O32  C31  109.93  3.000
 8UO  H14  C29  H13  105.59  3.000
 8UO  H14  C29  C26  110.64  3.000
 8UO  H13  C29  C26  109.61  3.000
 8UO  H14  C29  C31  109.60  3.000
 8UO  H13  C29  C31  106.46  3.000
 8UO  C26  C29  C31  114.48  3.000
 8UO  H15  C26  C27  108.47  3.000
 8UO  H15  C26  C25  107.91  3.000
 8UO  C27  C26  C25  108.53  3.000
 8UO  H15  C26  C29  108.76  3.000
 8UO  C25  C26  C29  110.42  3.000
 8UO  C27  C26  C29  112.63  3.000
 8UO  H17  C25  H16  107.18  3.000
 8UO  H17  C25  C24  109.19  3.000
 8UO  H16  C25  C24  108.77  3.000
 8UO  H17  C25  C26  109.89  3.000
 8UO  H16  C25  C26  110.54  3.000
 8UO  C24  C25  C26  111.18  3.000
 8UO  H19  C24  H18  106.66  3.000
 8UO  H19  C24  N23  110.00  3.000
 8UO  H18  C24  N23  109.99  3.000
 8UO  H19  C24  C25  109.36  3.000
 8UO  H18  C24  C25  109.43  3.000
 8UO  N23  C24  C25  111.28  3.000
 8UO  H21  C27  H20  107.13  3.000
 8UO  H21  C27  C28  108.17  3.000
 8UO  H20  C27  C28  108.98  3.000
 8UO  H21  C27  C26  111.13  3.000
 8UO  H20  C27  C26  109.40  3.000
 8UO  C28  C27  C26  111.89  3.000
 8UO  H23  C28  H22  107.16  3.000
 8UO  H23  C28  N23  111.39  3.000
 8UO  H22  C28  N23  109.30  3.000
 8UO  H23  C28  C27  109.37  3.000
 8UO  H22  C28  C27  108.40  3.000
 8UO  N23  C28  C27  111.09  3.000
 8UO  C28  N23  C24  112.64  3.000
 8UO  C24  N23  C19  117.65  3.000
 8UO  C28  N23  C19  118.56  3.000
 8UO  H24  C30  C18  119.01  3.000
 8UO  H24  C30  C19  122.46  3.000
 8UO  C18  C30  C19  118.53  3.000
 8UO  H25  C17  C18  118.96  3.000
 8UO  H25  C17  C16  123.18  3.000
 8UO  C18  C17  C16  117.86  3.000
 8UO  H28  C22  H27  107.14  3.000
 8UO  H28  C22  H26  108.41  3.000
 8UO  H27  C22  H26  107.27  3.000
 8UO  H28  C22  C14  111.47  3.000
 8UO  H27  C22  C14  109.65  3.000
 8UO  H26  C22  C14  112.67  3.000
 8UO  N11  N12  C6   102.56  3.000
 8UO  H4   C13  H3   107.89  3.000
 8UO  H4   C13  H2   108.14  3.000
 8UO  H3   C13  H2   107.38  3.000
 8UO  H4   C13  C10  111.27  3.000
 8UO  H3   C13  C10  111.19  3.000
 8UO  H2   C13  C10  110.82  3.000

loop_
_chem_comp_tor.comp_id
_chem_comp_tor.id
_chem_comp_tor.atom_id_1
_chem_comp_tor.atom_id_2
_chem_comp_tor.atom_id_3
_chem_comp_tor.atom_id_4
_chem_comp_tor.value_angle
_chem_comp_tor.value_angle_esd
_chem_comp_tor.period
 8UO  CONST_01  N12  N11  C10  C5      0.00   0.0  0
 8UO  CONST_02  N11  N12  C6   C5      0.00   0.0  0
 8UO  CONST_03  C10  N11  N12  C6      0.00   0.0  0
 8UO  CONST_04  N11  C10  C5   C6      0.00   0.0  0
 8UO  CONST_05  C30  C19  C20  C16     0.00   0.0  0
 8UO  CONST_06  C30  C18  C17  C16     0.00   0.0  0
 8UO  CONST_07  C18  C30  C19  C20     0.00   0.0  0
 8UO  CONST_08  C18  C17  C16  C20     0.00   0.0  0
 8UO  CONST_09  C17  C16  C20  C19     0.00   0.0  0
 8UO  CONST_10  C17  C18  C30  C19     0.00   0.0  0
 8UO  CONST_11  N12  C6   C5   C10     0.00   0.0  0
 8UO  CONST_12  C19  C20  C16  C4    180.00   0.0  0
 8UO  CONST_13  C18  C17  C16  C4    180.00   0.0  0
 8UO  CONST_14  N23  C19  C20  C16   180.00   0.0  0
 8UO  CONST_15  N23  C19  C30  C18   180.00   0.0  0
 8UO  CONST_16  C13  C10  C5   C4      0.00   0.0  0
 8UO  CONST_17  C13  C10  C5   C6    180.00   0.0  0
 8UO  CONST_18  N12  N11  C10  C13   180.00   0.0  0
 8UO  CONST_19  F21  C18  C17  C16   180.00   0.0  0
 8UO  CONST_20  F21  C18  C30  C19   180.00   0.0  0
 8UO  CONST_21  H8   C20  C16  C4      0.00   0.0  0
 8UO  CONST_22  H25  C17  C16  C4      0.00   0.0  0
 8UO  CONST_23  H9   N11  C10  C5    180.00   0.0  0
 8UO  CONST_24  H24  C30  C19  C20   180.00   0.0  0
 8UO  CONST_25  H12  O32  C31  O33     0.00   0.0  0
 8UO  Var_01    O1   C2   C3   C4     -7.23  30.0  1
 8UO  Var_02    C3   C2   O1   C6     -7.38  30.0  1
 8UO  Var_03    C28  N23  C19  C20  -171.75  30.0  2
 8UO  Var_04    C27  C28  N23  C19   160.54  30.0  1
 8UO  Var_05    C25  C24  N23  C19  -159.27  30.0  1
 8UO  Var_06    N12  C6   O1   C2   -169.77  30.0  1
 8UO  Var_07    N23  C28  C27  C26    55.49  30.0  1
 8UO  Var_08    N23  C24  C25  C26   -56.59  30.0  1
 8UO  Var_09    H2   C13  C10  C5    -63.09  30.0  2
 8UO  Var_10    H10  N7   C2   C3      4.83  30.0  2
 8UO  Var_11    C26  C29  C31  O33   -18.96  30.0  3
 8UO  Var_12    H5   C15  C14  C4     75.23  30.0  3
 8UO  Var_13    H26  C22  C14  C4     60.31  30.0  3

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 8UO  chir_01  C4   C16  C5   C3   positiv
 8UO  chir_02  C26  C29  C27  C25  positiv

loop_
_chem_comp_plane_atom.comp_id
_chem_comp_plane_atom.plane_id
_chem_comp_plane_atom.atom_id
_chem_comp_plane_atom.dist_esd
 8UO  plan-1  C4   0.020
 8UO  plan-1  C16  0.020
 8UO  plan-1  C20  0.020
 8UO  plan-1  C19  0.020
 8UO  plan-1  C18  0.020
 8UO  plan-1  N23  0.020
 8UO  plan-1  C30  0.020
 8UO  plan-1  F21  0.020
 8UO  plan-1  C17  0.020
 8UO  plan-1  H8   0.020
 8UO  plan-1  H24  0.020
 8UO  plan-1  H25  0.020
 8UO  plan-2  C4   0.020
 8UO  plan-2  C5   0.020
 8UO  plan-2  C6   0.020
 8UO  plan-2  N11  0.020
 8UO  plan-2  O1   0.020
 8UO  plan-2  C10  0.020
 8UO  plan-2  N12  0.020
 8UO  plan-2  H9   0.020
 8UO  plan-2  C13  0.020
 8UO  plan-3  O33  0.020
 8UO  plan-3  C31  0.020
 8UO  plan-3  O32  0.020
 8UO  plan-3  C29  0.020
 8UO  plan-3  H12  0.020

