# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Aug  1 14:22:04 2021
#   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  67  37  .  2022-07-24  2022-11-17
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

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  -0.302  31.9971  29.8070  99.9870
 8UU  C21  C  CT    0   1.051  32.9532  29.7371  99.0559
 8UU  F35  F  F     0  -0.316  34.1138  30.0130  99.6704
 8UU  F36  F  F     0  -0.316  33.0269  28.4535  98.6705
 8UU  C18  C  CR6   0  -0.155  32.7090  30.6517  97.8959
 8UU  C17  C  CR16  0  -0.414  31.5681  31.4437  97.8412
 8UU  C34  C  CR16  0  -0.376  33.6429  30.6638  96.8763
 8UU  C19  C  CR6   0   0.411  33.4649  31.5043  95.7722
 8UU  N23  N  NT    0  -0.515  34.4026  31.4910  94.7404
 8UU  C28  C  CH2   0  -0.300  35.7921  31.7280  95.1193
 8UU  C27  C  CH2   0  -0.433  36.7529  31.2808  94.0312
 8UU  C26  C  CH1   0  -0.244  36.4386  31.9633  92.7038
 8UU  C29  C  CH2   0  -0.420  37.3387  31.5009  91.5616
 8UU  C30  C  CH2   0  -0.565  38.8149  31.8165  91.8060
 8UU  C31  C  C     0   0.538  39.7072  31.5541  90.6254
 8UU  O33  O  O     0  -0.450  40.5331  32.3258  90.2013
 8UU  O32  O  OH1   0  -0.592  39.5072  30.3521  90.0937
 8UU  C25  C  CH2   0  -0.415  34.9714  31.7163  92.3711
 8UU  C24  C  CH2   0  -0.316  34.0454  32.1484  93.4974
 8UU  C20  C  CR16  0  -0.396  32.3237  32.3074  95.7406
 8UU  C16  C  CR6   0   0.223  31.3625  32.2723  96.7465
 8UU  C4   C  CR6   0  -0.189  30.1701  33.2337  96.6652
 8UU  C14  C  CH1   0  -0.211  28.9688  32.7992  97.5636
 8UU  C22  C  CH3   0  -0.664  27.8524  33.8398  97.5818
 8UU  C15  C  CH3   0  -0.676  28.3764  31.4455  97.1853
 8UU  C3   C  CR6   0  -0.152  30.6645  34.6053  97.1384
 8UU  C8   C  CSP   0   0.026  31.3738  34.6660  98.3490
 8UU  N9   N  NS    0  -0.288  31.9594  34.7185  99.3473
 8UU  C2   C  CR6   0   0.597  30.3449  35.7984  96.5444
 8UU  N7   N  NH2   0  -0.834  30.5876  37.0175  97.0442
 8UU  C5   C  CR56  0  -0.208  29.7410  33.4386  95.2436
 8UU  C10  C  CR5   0   0.357  29.4892  32.6019  94.1675
 8UU  C13  C  CH3   0  -0.748  29.6591  31.1398  93.9635
 8UU  N11  N  NR15  0  -0.484  29.1226  33.4117  93.1573
 8UU  N12  N  N     0  -0.289  29.1337  34.7121  93.4641
 8UU  C6   C  CR56  0   0.461  29.5133  34.7067  94.7134
 8UU  O1   O  O     0  -0.454  29.6874  35.8751  95.3766
 8UU  H1   H  HCR6  0   0.265  30.8558  31.4101  98.6509
 8UU  H2   H  HCR6  0   0.275  34.5043  30.0085  96.9123
 8UU  H3   H  HCH2  0   0.253  36.0197  31.1950  96.0408
 8UU  H4   H  HCH2  0   0.215  35.9507  32.7983  95.3248
 8UU  H5   H  HCH2  0   0.220  36.6881  30.1943  93.9102
 8UU  H6   H  HCH2  0   0.242  37.7681  31.5075  94.3650
 8UU  H7   H  HCH1  0   0.219  36.5795  33.0449  92.8393
 8UU  H8   H  HCH2  0   0.238  37.0100  31.9918  90.6406
 8UU  H9   H  HCH2  0   0.229  37.2034  30.4269  91.4074
 8UU  H10  H  HCH2  0   0.278  39.1955  31.2178  92.6397
 8UU  H11  H  HCH2  0   0.259  38.9380  32.8626  92.0894
 8UU  H12  H  HOH1  0   0.480  40.1079  30.2187  89.3453
 8UU  H13  H  HCH2  0   0.237  34.6871  32.2552  91.4637
 8UU  H14  H  HCH2  0   0.220  34.8190  30.6507  92.1706
 8UU  H15  H  HCH2  0   0.212  34.0728  33.2454  93.5940
 8UU  H16  H  HCH2  0   0.246  33.0216  31.8766  93.2333
 8UU  H17  H  HCR6  0   0.271  32.1793  33.0021  94.9247
 8UU  H18  H  HCH1  0   0.237  29.3511  32.7343  98.5883
 8UU  H19  H  HCH3  0   0.239  27.0354  33.4860  98.2121
 8UU  H20  H  HCH3  0   0.236  28.1769  34.7977  97.9865
 8UU  H21  H  HCH3  0   0.226  27.4391  34.0083  96.5852
 8UU  H22  H  HCH3  0   0.243  27.6308  31.1500  97.9247
 8UU  H23  H  HCH3  0   0.228  27.8679  31.4970  96.2208
 8UU  H24  H  HCH3  0   0.236  29.1169  30.6483  97.1340
 8UU  H25  H  HNH2  0   0.415  30.5942  37.8102  96.4223
 8UU  H26  H  HNH2  0   0.418  31.1426  37.1140  97.8779
 8UU  H27  H  HCH3  0   0.262  30.6358  30.9279  93.5234
 8UU  H28  H  HCH3  0   0.266  29.6018  30.5929  94.8991
 8UU  H29  H  HCH3  0   0.267  28.9001  30.7422  93.2902
 8UU  H30  H  HNR5  0   0.422  28.8687  33.1281  92.2242

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  double    1.207  0.020  1.207
 8UU  O32  C31  single    1.329  0.020  1.329
 8UU  C31  C30  single    1.503  0.020  1.503
 8UU  C29  C30  single    1.529  0.020  1.529
 8UU  C29  C26  single    1.526  0.020  1.526
 8UU  C25  C26  single    1.525  0.020  1.525
 8UU  C25  C24  single    1.521  0.020  1.521
 8UU  C26  C27  single    1.525  0.020  1.525
 8UU  N11  N12  aromatic  1.336  0.020  1.336
 8UU  N11  C10  aromatic  1.346  0.020  1.346
 8UU  C24  N23  single    1.451  0.020  1.451
 8UU  N12  C6   aromatic  1.306  0.020  1.306
 8UU  C13  C10  single    1.486  0.020  1.486
 8UU  C27  C28  single    1.519  0.020  1.519
 8UU  C10  C5   aromatic  1.386  0.020  1.386
 8UU  N23  C28  single    1.460  0.020  1.460
 8UU  N23  C19  single    1.394  0.020  1.394
 8UU  C6   C5   aromatic  1.393  0.020  1.393
 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  1.396  0.020  1.396
 8UU  C20  C16  aromatic  1.392  0.020  1.392
 8UU  C19  C34  aromatic  1.399  0.020  1.399
 8UU  C4   C16  single    1.534  0.020  1.534
 8UU  C4   C14  single    1.562  0.020  1.562
 8UU  C4   C3   single    1.533  0.020  1.533
 8UU  C16  C17  aromatic  1.388  0.020  1.388
 8UU  C15  C14  single    1.525  0.020  1.525
 8UU  C34  C18  aromatic  1.383  0.020  1.383
 8UU  C22  C14  single    1.526  0.020  1.526
 8UU  C2   C3   double    1.371  0.020  1.371
 8UU  C2   N7   single    1.340  0.020  1.340
 8UU  C3   C8   single    1.404  0.020  1.404
 8UU  C17  C18  aromatic  1.390  0.020  1.390
 8UU  C18  C21  single    1.497  0.020  1.497
 8UU  F36  C21  single    1.342  0.020  1.342
 8UU  C8   N9   triple    1.159  0.020  1.159
 8UU  C21  F35  single    1.342  0.020  1.342
 8UU  C21  F37  single    1.336  0.020  1.336
 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  O32  H12  single    0.850  0.020  0.980
 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  111.76  3.000
 8UU  F36  C21  F35  106.29  3.000
 8UU  C18  C21  F35  111.73  3.000
 8UU  F35  C21  F37  106.79  3.000
 8UU  F36  C21  F37  106.82  3.000
 8UU  C18  C21  F37  113.03  3.000
 8UU  C34  C18  C17  121.36  3.000
 8UU  C17  C18  C21  120.82  3.000
 8UU  C34  C18  C21  117.81  3.000
 8UU  H1   C17  C16  120.83  3.000
 8UU  H1   C17  C18  119.65  3.000
 8UU  C16  C17  C18  119.52  3.000
 8UU  H2   C34  C19  119.40  3.000
 8UU  H2   C34  C18  120.49  3.000
 8UU  C19  C34  C18  120.09  3.000
 8UU  C20  C19  N23  122.59  3.000
 8UU  C20  C19  C34  117.87  3.000
 8UU  N23  C19  C34  119.52  3.000
 8UU  C24  N23  C28  112.54  3.000
 8UU  C28  N23  C19  116.53  3.000
 8UU  C24  N23  C19  117.65  3.000
 8UU  H4   C28  H3   106.73  3.000
 8UU  H4   C28  C27  109.19  3.000
 8UU  H3   C28  C27  109.27  3.000
 8UU  H4   C28  N23  110.08  3.000
 8UU  H3   C28  N23  109.83  3.000
 8UU  C27  C28  N23  111.62  3.000
 8UU  H6   C27  H5   107.13  3.000
 8UU  H6   C27  C26  111.38  3.000
 8UU  H5   C27  C26  109.61  3.000
 8UU  H6   C27  C28  107.93  3.000
 8UU  H5   C27  C28  109.50  3.000
 8UU  C26  C27  C28  111.19  3.000
 8UU  H7   C26  C25  108.04  3.000
 8UU  H7   C26  C29  108.35  3.000
 8UU  C25  C26  C29  110.80  3.000
 8UU  H7   C26  C27  107.86  3.000
 8UU  C25  C26  C27  108.41  3.000
 8UU  C29  C26  C27  113.22  3.000
 8UU  H9   C29  H8   106.55  3.000
 8UU  H9   C29  C30  110.16  3.000
 8UU  H8   C29  C30  109.38  3.000
 8UU  H9   C29  C26  109.28  3.000
 8UU  H8   C29  C26  108.48  3.000
 8UU  C30  C29  C26  112.78  3.000
 8UU  H11  C30  H10  106.70  3.000
 8UU  H11  C30  C31  107.73  3.000
 8UU  H10  C30  C31  107.24  3.000
 8UU  H11  C30  C29  110.39  3.000
 8UU  H10  C30  C29  110.15  3.000
 8UU  C31  C30  C29  114.30  3.000
 8UU  O32  C31  O33  122.71  3.000
 8UU  O32  C31  C30  112.50  3.000
 8UU  O33  C31  C30  124.79  3.000
 8UU  H12  O32  C31  109.89  3.000
 8UU  H14  C25  H13  106.96  3.000
 8UU  H14  C25  C24  109.11  3.000
 8UU  H13  C25  C24  108.45  3.000
 8UU  H14  C25  C26  109.36  3.000
 8UU  H13  C25  C26  110.59  3.000
 8UU  C24  C25  C26  112.23  3.000
 8UU  H16  C24  H15  107.01  3.000
 8UU  H16  C24  C25  108.73  3.000
 8UU  H15  C24  C25  109.43  3.000
 8UU  H16  C24  N23  108.99  3.000
 8UU  H15  C24  N23  111.71  3.000
 8UU  C25  C24  N23  110.85  3.000
 8UU  H17  C20  C16  117.99  3.000
 8UU  H17  C20  C19  119.73  3.000
 8UU  C16  C20  C19  122.26  3.000
 8UU  C4   C16  C20  118.87  3.000
 8UU  C4   C16  C17  122.08  3.000
 8UU  C20  C16  C17  118.86  3.000
 8UU  C5   C4   C3   105.24  3.000
 8UU  C3   C4   C14  108.63  3.000
 8UU  C5   C4   C14  111.30  3.000
 8UU  C3   C4   C16  107.09  3.000
 8UU  C14  C4   C16  113.15  3.000
 8UU  C5   C4   C16  111.00  3.000
 8UU  H18  C14  C15  108.35  3.000
 8UU  H18  C14  C22  106.53  3.000
 8UU  C15  C14  C22  108.90  3.000
 8UU  H18  C14  C4   106.62  3.000
 8UU  C22  C14  C4   112.32  3.000
 8UU  C15  C14  C4   113.77  3.000
 8UU  H21  C22  H20  108.43  3.000
 8UU  H21  C22  H19  107.09  3.000
 8UU  H20  C22  H19  107.08  3.000
 8UU  H21  C22  C14  111.79  3.000
 8UU  H20  C22  C14  112.71  3.000
 8UU  H19  C22  C14  109.48  3.000
 8UU  H24  C15  H23  108.03  3.000
 8UU  H24  C15  H22  107.36  3.000
 8UU  H23  C15  H22  107.06  3.000
 8UU  H24  C15  C14  113.40  3.000
 8UU  H23  C15  C14  110.99  3.000
 8UU  H22  C15  C14  109.74  3.000
 8UU  C2   C3   C8   116.98  3.000
 8UU  C8   C3   C4   117.88  3.000
 8UU  C2   C3   C4   124.74  3.000
 8UU  N9   C8   C3   180.00  3.000
 8UU  O1   C2   N7   111.18  3.000
 8UU  N7   C2   C3   126.03  3.000
 8UU  O1   C2   C3   122.75  3.000
 8UU  H26  N7   H25  115.62  3.000
 8UU  H26  N7   C2   119.75  3.000
 8UU  H25  N7   C2   119.13  3.000
 8UU  C6   C5   C10  102.96  3.000
 8UU  C6   C5   C4   122.14  3.000
 8UU  C10  C5   C4   134.89  3.000
 8UU  N11  C10  C13  121.35  3.000
 8UU  C13  C10  C5   132.82  3.000
 8UU  N11  C10  C5   105.61  3.000
 8UU  H29  C13  H28  108.18  3.000
 8UU  H29  C13  H27  107.65  3.000
 8UU  H28  C13  H27  107.27  3.000
 8UU  H29  C13  C10  111.36  3.000
 8UU  H28  C13  C10  111.80  3.000
 8UU  H27  C13  C10  110.40  3.000
 8UU  H30  N11  N12  119.25  3.000
 8UU  H30  N11  C10  126.47  3.000
 8UU  N12  N11  C10  114.27  3.000
 8UU  C6   N12  N11  102.60  3.000
 8UU  O1   C6   N12  120.15  3.000
 8UU  O1   C6   C5   125.29  3.000
 8UU  N12  C6   C5   114.54  3.000
 8UU  C6   O1   C2   116.07  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  CONST_25  H12  O32  C31  C30   180.00   0.0  0
 8UU  Var_01    C24  N23  C19  C34   167.00  30.0  1
 8UU  Var_02    C25  C24  N23  C19  -163.85  30.0  1
 8UU  Var_03    C27  C28  N23  C19   162.62  30.0  1
 8UU  Var_04    C26  C25  C24  N23   -55.88  30.0  1
 8UU  Var_05    C26  C27  C28  N23    56.18  30.0  1
 8UU  Var_06    O1   C2   C3   C4     -8.35  30.0  1
 8UU  Var_07    N12  C6   O1   C2   -166.18  30.0  1
 8UU  Var_08    C34  C18  C21  F37   179.67  30.0  3
 8UU  Var_09    C2   C3   C8   N9    -14.10  30.0  2
 8UU  Var_10    H25  N7   C2   C3    160.16  30.0  2
 8UU  Var_11    H27  C13  C10  C5    -92.56  30.0  2
 8UU  Var_12    C31  C30  C29  C26  -171.80  30.0  3
 8UU  Var_13    H22  C15  C14  C4    172.96  30.0  3
 8UU  Var_14    H19  C22  C14  C4    179.40  30.0  3
 8UU  Var_15    O33  C31  C30  C29   132.06  30.0  1

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
 8UU  plan-3  H12  0.020

