# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version 1.18.1-3865-
#   - file written: Sun Jun 14 15:02:04 2020
#   Inital geometry file: a 163 line input string
#   Ligand name: 3-[1-[3-[(4~{S})-6-azanyl-5-cyano-3-methyl-4-propan-2-yl-2~{H}-pyrano[2,3-c]pyrazol-4-yl]-5-(trifluoromethyl)phenyl]piperidin-4-yl]propanoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)[C@]1(c2cc(cc(c2)C(F)(F)F)N3CCC(CC3)CCC(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
 8UU  8UU  '3-[1-[3-[(4~{S})-6-azanyl-5-cyano-3-methyl-4-propan-2-yl-2~{H}-pyrano[2,3-c]pyrazol-4-yl]-5-(trifluoromethyl)phenyl]piperidin-4-yl]propanoic acid'  ligand  66  37  .  2022-07-24  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_8UU
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
 8UU  F37  F  F      0  -0.308  -0.9138   5.0689  -0.2285
 8UU  C21  C  CT     0   1.049  -1.8188   4.1647   0.1648
 8UU  F35  F  F      0  -0.317  -2.1225   4.4583   1.4404
 8UU  F36  F  F      0  -0.309  -2.9283   4.3891  -0.5505
 8UU  C18  C  CR6    0  -0.143  -1.3267   2.7574   0.0312
 8UU  C17  C  CR16   0  -0.417  -2.2490   1.7349  -0.1362
 8UU  C34  C  CR16   0  -0.432   0.0335   2.5013   0.1263
 8UU  C19  C  CR6    0   0.420   0.4993   1.1832   0.0766
 8UU  N23  N  NT     0  -0.517   1.8473   0.8633   0.1983
 8UU  C28  C  CH2    0  -0.313   2.7626   1.9239   0.5755
 8UU  C27  C  CH2    0  -0.414   4.0879   1.3569   1.0582
 8UU  C26  C  CH1    0  -0.235   4.7355   0.4342   0.0327
 8UU  C29  C  CH2    0  -0.390   6.0509  -0.1387   0.5557
 8UU  C30  C  CH2    0  -0.596   6.8224  -0.9512  -0.4717
 8UU  C31  C  C      0   0.415   8.2143  -1.4440  -0.0370
 8UU  O33  O  O      0  -0.609   8.6123  -1.1429   1.1054
 8UU  O32  O  OC    -1  -0.635   8.8411  -2.1181  -0.8825
 8UU  C25  C  CH2    0  -0.429   3.7237  -0.6406  -0.3510
 8UU  C24  C  CH2    0  -0.294   2.4063  -0.0376  -0.8065
 8UU  C20  C  CR16   0  -0.359  -0.4474   0.1646  -0.0774
 8UU  C16  C  CR6    0   0.207  -1.8045   0.4176  -0.2004
 8UU  C4   C  CR6    0  -0.167  -2.7629  -0.7773  -0.3079
 8UU  C14  C  CH1    0  -0.218  -4.1861  -0.3788  -0.8017
 8UU  C22  C  CH3    0  -0.676  -4.2057   0.1890  -2.2199
 8UU  C15  C  CH3    0  -0.661  -5.1696  -1.5414  -0.7141
 8UU  C3   C  CR6    0  -0.228  -2.1529  -1.8490  -1.2099
 8UU  C8   C  CSP    0   0.034  -1.6110  -1.4684  -2.4498
 8UU  N9   N  NS     0  -0.289  -1.1338  -1.1603  -3.4594
 8UU  C2   C  CR6    0   0.612  -2.0572  -3.1826  -0.8956
 8UU  N7   N  NH2    0  -0.838  -1.5930  -4.1407  -1.7054
 8UU  C5   C  CR56   0  -0.143  -2.8582  -1.4079   1.0491
 8UU  C10  C  CR5    0   0.367  -3.1454  -0.9222   2.3126
 8UU  C13  C  CH3    0  -0.750  -3.4352   0.4483   2.8071
 8UU  N11  N  NR15   0  -0.492  -3.1230  -1.9942   3.1250
 8UU  N12  N  N      0  -0.295  -2.8421  -3.1450   2.5070
 8UU  C6   C  CR56   0   0.459  -2.6890  -2.7707   1.2643
 8UU  O1   O  O      0  -0.454  -2.3948  -3.6797   0.3042
 8UU  H1   H  HCR6   0   0.268  -3.3014   1.9668  -0.2096
 8UU  H2   H  HCR6   0   0.283   0.7302   3.3218   0.2154
 8UU  H3   H  HCH2   0   0.208   2.9407   2.6191  -0.2608
 8UU  H4   H  HCH2   0   0.249   2.3150   2.5055   1.3831
 8UU  H5   H  HCH2   0   0.231   4.7527   2.1910   1.2976
 8UU  H6   H  HCH2   0   0.214   3.9233   0.8045   1.9898
 8UU  H7   H  HCH1   0   0.203   4.9558   1.0267  -0.8672
 8UU  H8   H  HCH2   0   0.208   6.6748   0.6895   0.9042
 8UU  H9   H  HCH2   0   0.198   5.8442  -0.7508   1.4402
 8UU  H10  H  HCH2   0   0.223   6.2436  -1.8288  -0.7786
 8UU  H11  H  HCH2   0   0.216   6.9399  -0.3607  -1.3885
 8UU  H13  H  HCH2   0   0.237   4.1073  -1.2668  -1.1591
 8UU  H14  H  HCH2   0   0.214   3.5483  -1.3004   0.5066
 8UU  H15  H  HCH2   0   0.248   1.7003  -0.8384  -1.0168
 8UU  H16  H  HCH2   0   0.212   2.5600   0.5040  -1.7528
 8UU  H17  H  HCR6   0   0.262  -0.1130  -0.8651  -0.0784
 8UU  H18  H  HCH1   0   0.233  -4.5549   0.3949  -0.1185
 8UU  H19  H  HCH3   0   0.240  -5.1788   0.6393  -2.4205
 8UU  H20  H  HCH3   0   0.236  -3.4489   0.9549  -2.3874
 8UU  H21  H  HCH3   0   0.231  -4.0552  -0.5955  -2.9628
 8UU  H22  H  HCH3   0   0.237  -5.3169  -1.8880   0.3084
 8UU  H23  H  HCH3   0   0.237  -6.1426  -1.2283  -1.0951
 8UU  H24  H  HCH3   0   0.223  -4.8406  -2.3891  -1.3195
 8UU  H25  H  HNH2   0   0.421  -1.5206  -3.9812  -2.6956
 8UU  H26  H  HNH2   0   0.418  -1.6138  -5.1013  -1.4058
 8UU  H27  H  HCH3   0   0.260  -4.2801   0.8852   2.2761
 8UU  H28  H  HCH3   0   0.267  -3.6762   0.4409   3.8693
 8UU  H29  H  HCH3   0   0.264  -2.5803   1.1080   2.6594
 8UU  H30  H  HNR5   0   0.421  -3.2856  -1.9970   4.1195

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
 8UU  O33  C31  deloc     1.247  0.020  1.247
 8UU  O32  C31  deloc     1.250  0.020  1.250
 8UU  C31  C30  single    1.539  0.020  1.539
 8UU  C29  C30  single    1.520  0.020  1.520
 8UU  C29  C26  single    1.527  0.020  1.527
 8UU  C25  C26  single    1.525  0.020  1.525
 8UU  C25  C24  single    1.519  0.020  1.519
 8UU  C26  C27  single    1.524  0.020  1.524
 8UU  N11  N12  aromatic  1.336  0.020  1.336
 8UU  N11  C10  aromatic  1.345  0.020  1.345
 8UU  C24  N23  single    1.461  0.020  1.461
 8UU  N12  C6   aromatic  1.307  0.020  1.307
 8UU  C13  C10  single    1.486  0.020  1.486
 8UU  C27  C28  single    1.520  0.020  1.520
 8UU  C10  C5   aromatic  1.384  0.020  1.384
 8UU  N23  C28  single    1.451  0.020  1.451
 8UU  N23  C19  single    1.391  0.020  1.391
 8UU  C6   C5   aromatic  1.390  0.020  1.390
 8UU  C6   O1   single    1.355  0.020  1.355
 8UU  C5   C4   single    1.499  0.020  1.499
 8UU  O1   C2   single    1.342  0.020  1.342
 8UU  C20  C19  aromatic  1.399  0.020  1.399
 8UU  C20  C16  aromatic  1.386  0.020  1.386
 8UU  C19  C34  aromatic  1.399  0.020  1.399
 8UU  C4   C16  single    1.536  0.020  1.536
 8UU  C4   C14  single    1.558  0.020  1.558
 8UU  C4   C3   single    1.528  0.020  1.528
 8UU  C16  C17  aromatic  1.392  0.020  1.392
 8UU  C15  C14  single    1.525  0.020  1.525
 8UU  C34  C18  aromatic  1.387  0.020  1.387
 8UU  C22  C14  single    1.528  0.020  1.528
 8UU  C2   C3   double    1.374  0.020  1.374
 8UU  C2   N7   single    1.338  0.020  1.338
 8UU  C3   C8   single    1.406  0.020  1.406
 8UU  C17  C18  aromatic  1.387  0.020  1.387
 8UU  C18  C21  single    1.497  0.020  1.497
 8UU  F36  C21  single    1.339  0.020  1.339
 8UU  C8   N9   triple    1.158  0.020  1.158
 8UU  C21  F35  single    1.344  0.020  1.344
 8UU  C21  F37  single    1.338  0.020  1.338
 8UU  C17  H1   single    0.930  0.020  1.080
 8UU  C34  H2   single    0.930  0.020  1.080
 8UU  C28  H3   single    0.970  0.020  1.090
 8UU  C28  H4   single    0.970  0.020  1.090
 8UU  C27  H5   single    0.970  0.020  1.090
 8UU  C27  H6   single    0.970  0.020  1.090
 8UU  C26  H7   single    0.970  0.020  1.090
 8UU  C29  H8   single    0.970  0.020  1.090
 8UU  C29  H9   single    0.970  0.020  1.090
 8UU  C30  H10  single    0.970  0.020  1.090
 8UU  C30  H11  single    0.970  0.020  1.090
 8UU  C25  H13  single    0.970  0.020  1.090
 8UU  C25  H14  single    0.970  0.020  1.090
 8UU  C24  H15  single    0.970  0.020  1.090
 8UU  C24  H16  single    0.970  0.020  1.090
 8UU  C20  H17  single    0.930  0.020  1.080
 8UU  C14  H18  single    0.970  0.020  1.090
 8UU  C22  H19  single    0.970  0.020  1.090
 8UU  C22  H20  single    0.970  0.020  1.090
 8UU  C22  H21  single    0.970  0.020  1.090
 8UU  C15  H22  single    0.970  0.020  1.090
 8UU  C15  H23  single    0.970  0.020  1.090
 8UU  C15  H24  single    0.970  0.020  1.090
 8UU  N7   H25  single    0.890  0.020  1.040
 8UU  N7   H26  single    0.890  0.020  1.040
 8UU  C13  H27  single    0.970  0.020  1.090
 8UU  C13  H28  single    0.970  0.020  1.090
 8UU  C13  H29  single    0.970  0.020  1.090
 8UU  N11  H30  single    0.860  0.020  1.020

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
 8UU  C18  C21  F36  112.47  3.000
 8UU  F36  C21  F35  106.45  3.000
 8UU  C18  C21  F35  111.38  3.000
 8UU  F35  C21  F37  106.51  3.000
 8UU  F36  C21  F37  106.86  3.000
 8UU  C18  C21  F37  112.75  3.000
 8UU  C34  C18  C17  121.60  3.000
 8UU  C17  C18  C21  119.03  3.000
 8UU  C34  C18  C21  119.32  3.000
 8UU  H1   C17  C16  120.76  3.000
 8UU  H1   C17  C18  119.84  3.000
 8UU  C16  C17  C18  119.40  3.000
 8UU  H2   C34  C19  120.26  3.000
 8UU  H2   C34  C18  119.85  3.000
 8UU  C19  C34  C18  119.87  3.000
 8UU  C20  C19  N23  119.87  3.000
 8UU  C20  C19  C34  117.69  3.000
 8UU  N23  C19  C34  122.44  3.000
 8UU  C24  N23  C28  112.85  3.000
 8UU  C28  N23  C19  117.78  3.000
 8UU  C24  N23  C19  116.91  3.000
 8UU  H4   C28  H3   106.96  3.000
 8UU  H4   C28  C27  108.75  3.000
 8UU  H3   C28  C27  109.59  3.000
 8UU  H4   C28  N23  108.86  3.000
 8UU  H3   C28  N23  111.46  3.000
 8UU  C27  C28  N23  111.09  3.000
 8UU  H6   C27  H5   106.85  3.000
 8UU  H6   C27  C26  109.32  3.000
 8UU  H5   C27  C26  110.55  3.000
 8UU  H6   C27  C28  109.09  3.000
 8UU  H5   C27  C28  108.37  3.000
 8UU  C26  C27  C28  112.50  3.000
 8UU  H7   C26  C25  107.86  3.000
 8UU  H7   C26  C29  108.05  3.000
 8UU  C25  C26  C29  113.15  3.000
 8UU  H7   C26  C27  108.03  3.000
 8UU  C25  C26  C27  108.30  3.000
 8UU  C29  C26  C27  111.27  3.000
 8UU  H9   C29  H8   105.87  3.000
 8UU  H9   C29  C30  110.05  3.000
 8UU  H8   C29  C30  109.30  3.000
 8UU  H9   C29  C26  108.88  3.000
 8UU  H8   C29  C26  108.44  3.000
 8UU  C30  C29  C26  113.97  3.000
 8UU  H11  C30  H10  104.70  3.000
 8UU  H11  C30  C31  108.15  3.000
 8UU  H10  C30  C31  107.49  3.000
 8UU  H11  C30  C29  109.36  3.000
 8UU  H10  C30  C29  110.45  3.000
 8UU  C31  C30  C29  116.05  3.000
 8UU  O32  C31  O33  126.16  3.000
 8UU  O32  C31  C30  115.79  3.000
 8UU  O33  C31  C30  118.05  3.000
 8UU  H14  C25  H13  106.86  3.000
 8UU  H14  C25  C24  109.56  3.000
 8UU  H13  C25  C24  108.09  3.000
 8UU  H14  C25  C26  109.48  3.000
 8UU  H13  C25  C26  110.93  3.000
 8UU  C24  C25  C26  111.78  3.000
 8UU  H16  C24  H15  106.65  3.000
 8UU  H16  C24  C25  109.38  3.000
 8UU  H15  C24  C25  109.18  3.000
 8UU  H16  C24  N23  109.96  3.000
 8UU  H15  C24  N23  109.79  3.000
 8UU  C25  C24  N23  111.75  3.000
 8UU  H17  C20  C16  118.43  3.000
 8UU  H17  C20  C19  118.92  3.000
 8UU  C16  C20  C19  122.64  3.000
 8UU  C4   C16  C20  118.37  3.000
 8UU  C4   C16  C17  122.71  3.000
 8UU  C20  C16  C17  118.79  3.000
 8UU  C5   C4   C3   105.35  3.000
 8UU  C3   C4   C14  110.91  3.000
 8UU  C5   C4   C14  109.65  3.000
 8UU  C3   C4   C16  109.76  3.000
 8UU  C14  C4   C16  113.15  3.000
 8UU  C5   C4   C16  107.67  3.000
 8UU  H18  C14  C15  106.57  3.000
 8UU  H18  C14  C22  108.18  3.000
 8UU  C15  C14  C22  109.17  3.000
 8UU  H18  C14  C4   106.87  3.000
 8UU  C22  C14  C4   113.64  3.000
 8UU  C15  C14  C4   112.07  3.000
 8UU  H21  C22  H20  107.75  3.000
 8UU  H21  C22  H19  107.13  3.000
 8UU  H20  C22  H19  107.52  3.000
 8UU  H21  C22  C14  111.30  3.000
 8UU  H20  C22  C14  113.27  3.000
 8UU  H19  C22  C14  109.61  3.000
 8UU  H24  C15  H23  107.32  3.000
 8UU  H24  C15  H22  108.30  3.000
 8UU  H23  C15  H22  107.37  3.000
 8UU  H24  C15  C14  111.43  3.000
 8UU  H23  C15  C14  109.65  3.000
 8UU  H22  C15  C14  112.55  3.000
 8UU  C2   C3   C8   115.97  3.000
 8UU  C8   C3   C4   119.00  3.000
 8UU  C2   C3   C4   125.02  3.000
 8UU  N9   C8   C3   180.00  3.000
 8UU  O1   C2   N7   111.31  3.000
 8UU  N7   C2   C3   125.53  3.000
 8UU  O1   C2   C3   123.14  3.000
 8UU  H26  N7   H25  116.48  3.000
 8UU  H26  N7   C2   119.75  3.000
 8UU  H25  N7   C2   120.51  3.000
 8UU  C6   C5   C10  103.18  3.000
 8UU  C6   C5   C4   123.00  3.000
 8UU  C10  C5   C4   133.79  3.000
 8UU  N11  C10  C13  122.51  3.000
 8UU  C13  C10  C5   131.93  3.000
 8UU  N11  C10  C5   105.57  3.000
 8UU  H29  C13  H28  108.05  3.000
 8UU  H29  C13  H27  107.43  3.000
 8UU  H28  C13  H27  107.85  3.000
 8UU  H29  C13  C10  111.12  3.000
 8UU  H28  C13  C10  111.19  3.000
 8UU  H27  C13  C10  111.04  3.000
 8UU  H30  N11  N12  119.21  3.000
 8UU  H30  N11  C10  126.55  3.000
 8UU  N12  N11  C10  114.24  3.000
 8UU  C6   N12  N11  102.58  3.000
 8UU  O1   C6   N12  120.48  3.000
 8UU  O1   C6   C5   125.08  3.000
 8UU  N12  C6   C5   114.44  3.000
 8UU  C6   O1   C2   116.09  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
 8UU  CONST_01  C20  C19  C34  C18     0.00   0.0  0
 8UU  CONST_02  C20  C16  C17  C18     0.00   0.0  0
 8UU  CONST_03  C19  C20  C16  C17     0.00   0.0  0
 8UU  CONST_04  C19  C34  C18  C17     0.00   0.0  0
 8UU  CONST_05  C16  C20  C19  C34     0.00   0.0  0
 8UU  CONST_06  C16  C17  C18  C34     0.00   0.0  0
 8UU  CONST_07  N12  N11  C10  C5      0.00   0.0  0
 8UU  CONST_08  N11  N12  C6   C5      0.00   0.0  0
 8UU  CONST_09  C6   N12  N11  C10     0.00   0.0  0
 8UU  CONST_10  N12  C6   C5   C10     0.00   0.0  0
 8UU  CONST_11  C6   C5   C10  N11     0.00   0.0  0
 8UU  CONST_12  N23  C19  C34  C18   180.00   0.0  0
 8UU  CONST_13  C4   C16  C17  C18   180.00   0.0  0
 8UU  CONST_14  C4   C16  C20  C19   180.00   0.0  0
 8UU  CONST_15  C16  C20  C19  N23   180.00   0.0  0
 8UU  CONST_16  C19  C34  C18  C21   180.00   0.0  0
 8UU  CONST_17  C16  C17  C18  C21   180.00   0.0  0
 8UU  CONST_18  C13  C10  C5   C4      0.00   0.0  0
 8UU  CONST_19  N12  N11  C10  C13   180.00   0.0  0
 8UU  CONST_20  C6   C5   C10  C13   180.00   0.0  0
 8UU  CONST_21  H17  C20  C16  C17   180.00   0.0  0
 8UU  CONST_22  H2   C34  C18  C17   180.00   0.0  0
 8UU  CONST_23  H1   C17  C18  C34   180.00   0.0  0
 8UU  CONST_24  H30  N11  C10  C5    180.00   0.0  0
 8UU  Var_01    C24  N23  C19  C34  -130.64  30.0  2
 8UU  Var_02    C25  C24  N23  C19  -162.66  30.0  1
 8UU  Var_03    C27  C28  N23  C19   163.35  30.0  1
 8UU  Var_04    C26  C25  C24  N23   -55.28  30.0  1
 8UU  Var_05    C26  C27  C28  N23    55.58  30.0  1
 8UU  Var_06    O1   C2   C3   C4     -5.79  30.0  1
 8UU  Var_07    N12  C6   O1   C2   -170.22  30.0  1
 8UU  Var_08    C34  C18  C21  F37    28.38  30.0  2
 8UU  Var_09    C2   C3   C8   N9    -70.35  30.0  1
 8UU  Var_10    H25  N7   C2   C3    -17.36  30.0  2
 8UU  Var_11    H27  C13  C10  C5     56.50  30.0  2
 8UU  Var_12    C31  C30  C29  C26   174.65  30.0  3
 8UU  Var_13    H22  C15  C14  C4     62.18  30.0  3
 8UU  Var_14    H19  C22  C14  C4   -167.98  30.0  3
 8UU  Var_15    O33  C31  C30  C29    -0.39  30.0  2

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
 8UU  chir_01  C26  C29  C25  C27  negativ
 8UU  chir_02  C4   C16  C5   C3   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
 8UU  plan-1  C21  0.020
 8UU  plan-1  C18  0.020
 8UU  plan-1  C17  0.020
 8UU  plan-1  C34  0.020
 8UU  plan-1  C19  0.020
 8UU  plan-1  N23  0.020
 8UU  plan-1  C20  0.020
 8UU  plan-1  C16  0.020
 8UU  plan-1  C4   0.020
 8UU  plan-1  H1   0.020
 8UU  plan-1  H2   0.020
 8UU  plan-1  H17  0.020
 8UU  plan-2  C4   0.020
 8UU  plan-2  C5   0.020
 8UU  plan-2  C10  0.020
 8UU  plan-2  C13  0.020
 8UU  plan-2  N11  0.020
 8UU  plan-2  N12  0.020
 8UU  plan-2  C6   0.020
 8UU  plan-2  O1   0.020
 8UU  plan-2  H30  0.020
 8UU  plan-3  C30  0.020
 8UU  plan-3  C31  0.020
 8UU  plan-3  O33  0.020
 8UU  plan-3  O32  0.020

