# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Mar  7 17:20:40 2022
#   Inital geometry file: a 160 line input string
#   Ligand name: (3beta,8alpha,9beta)-3-hydroxycholest-5-en-7-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@@]4(C)CC[C@H](O)CC4=CC3=O
#
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
 0GV  0GV  (3beta,8alpha,9beta)-3-hydroxycholest-5-en-7-one  ligand  73  29  .  2022-03-08  2022-03-08
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_0GV
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
 0GV  C10  C  CT    0  -0.151    3.7782   0.6168  -0.1468
 0GV  C11  C  CH2   0  -0.448    1.4524   1.5949   0.3220
 0GV  C12  C  CH2   0  -0.411   -0.0014   1.3236   0.6948
 0GV  C13  C  CT    0  -0.057   -0.6093   0.2484  -0.2014
 0GV  C14  C  CH1   0  -0.171    0.2282  -1.0328  -0.0019
 0GV  C15  C  CH2   0  -0.438   -0.6055  -2.1086  -0.6932
 0GV  C16  C  CH2   0  -0.450   -2.0570  -1.6949  -0.3864
 0GV  C17  C  CH1   0  -0.167   -2.0090  -0.2650   0.2131
 0GV  C18  C  CH3   0  -0.692   -0.6234   0.6919  -1.6692
 0GV  C9   C  CH1   0  -0.199    2.3333   0.3427   0.3388
 0GV  C19  C  CH3   0  -0.666    3.8136   1.1666  -1.5829
 0GV  C1   C  CH2   0  -0.439    4.4420   1.6245   0.8167
 0GV  C2   C  CH2   0  -0.470    5.9477   1.7716   0.6452
 0GV  C3   C  CH1   0   0.087    6.6300   0.4310   0.8222
 0GV  O1   O  OH1   0  -0.674    8.0209   0.6023   0.6641
 0GV  C4   C  CH2   0  -0.555    6.0689  -0.5637  -0.1949
 0GV  C5   C  C     0   0.249    4.5739  -0.6703  -0.1293
 0GV  C6   C  C1    0  -0.447    3.9896  -1.8750  -0.0779
 0GV  C7   C  C     0   0.444    2.5410  -2.0805  -0.1003
 0GV  O7   O  O     0  -0.427    2.0804  -3.1941   0.0779
 0GV  C8   C  CH1   0  -0.405    1.6932  -0.8611  -0.3882
 0GV  C20  C  CH1   0  -0.229   -3.2483   0.5591  -0.1653
 0GV  C21  C  CH3   0  -0.673   -3.1758   2.0143   0.2898
 0GV  C22  C  CH2   0  -0.407   -4.5096  -0.1112   0.3997
 0GV  C23  C  CH2   0  -0.429   -5.8269   0.4238  -0.1524
 0GV  C24  C  CH2   0  -0.393   -7.0328  -0.3341   0.3914
 0GV  C25  C  CH1   0  -0.229   -8.3828   0.1152  -0.1714
 0GV  C26  C  CH3   0  -0.652   -9.4915  -0.8260   0.2902
 0GV  C27  C  CH3   0  -0.657   -8.7192   1.5539   0.2093
 0GV  H1   H  HCH2  0   0.225    1.4802   2.0747  -0.6589
 0GV  H2   H  HCH2  0   0.243    1.8633   2.3270   1.0197
 0GV  H3   H  HCH2  0   0.210   -0.0622   0.9866   1.7363
 0GV  H4   H  HCH2  0   0.231   -0.5558   2.2614   0.6456
 0GV  H5   H  HCH1  0   0.214    0.2034  -1.2445   1.0772
 0GV  H6   H  HCH2  0   0.212   -0.4136  -2.1109  -1.7697
 0GV  H7   H  HCH2  0   0.236   -0.3781  -3.1077  -0.3318
 0GV  H8   H  HCH2  0   0.218   -2.6723  -1.7057  -1.2902
 0GV  H9   H  HCH2  0   0.228   -2.5250  -2.3955   0.3060
 0GV  H10  H  HCH1  0   0.204   -1.9974  -0.3476   1.3094
 0GV  H11  H  HCH3  0   0.235   -1.1632  -0.0107  -2.3058
 0GV  H12  H  HCH3  0   0.232   -1.1082   1.6631  -1.7822
 0GV  H13  H  HCH3  0   0.232    0.3770   0.7939  -2.0911
 0GV  H14  H  HCH1  0   0.227    2.4215   0.0439   1.3937
 0GV  H15  H  HCH3  0   0.239    3.3021   0.5064  -2.2851
 0GV  H16  H  HCH3  0   0.241    3.3439   2.1487  -1.6383
 0GV  H17  H  HCH3  0   0.243    4.8369   1.2843  -1.9392
 0GV  H18  H  HCH2  0   0.249    3.9721   2.6013   0.6933
 0GV  H19  H  HCH2  0   0.233    4.2338   1.3093   1.8452
 0GV  H20  H  HCH2  0   0.226    6.1882   2.1782  -0.3427
 0GV  H21  H  HCH2  0   0.246    6.3252   2.4857   1.3813
 0GV  H22  H  HCH1  0   0.203    6.4013   0.0565   1.8314
 0GV  H23  H  HOH1  0   0.449    8.4553  -0.2270   0.8858
 0GV  H24  H  HCH2  0   0.254    6.3591  -0.2241  -1.1960
 0GV  H25  H  HCH2  0   0.258    6.5152  -1.5512  -0.0539
 0GV  H26  H  H     0   0.246    4.5998  -2.7718  -0.0324
 0GV  H27  H  HCH1  0   0.262    1.7637  -0.7075  -1.4742
 0GV  H28  H  HCH1  0   0.203   -3.3343   0.5464  -1.2602
 0GV  H29  H  HCH3  0   0.212   -2.9789   2.0830   1.3625
 0GV  H30  H  HCH3  0   0.227   -2.3948   2.5706  -0.2271
 0GV  H31  H  HCH3  0   0.232   -4.1110   2.5394   0.0944
 0GV  H32  H  HCH2  0   0.228   -4.4758  -1.1859   0.1991
 0GV  H33  H  HCH2  0   0.203   -4.5043  -0.0123   1.4924
 0GV  H34  H  HCH2  0   0.216   -5.9306   1.4878   0.0741
 0GV  H35  H  HCH2  0   0.204   -5.8163   0.3462  -1.2459
 0GV  H36  H  HCH2  0   0.211   -6.9028  -1.4010   0.1782
 0GV  H37  H  HCH2  0   0.201   -7.0550  -0.2476   1.4849
 0GV  H38  H  HCH1  0   0.207   -8.3240   0.0566  -1.2654
 0GV  H39  H  HCH3  0   0.211   -9.5839  -0.8130   1.3792
 0GV  H40  H  HCH3  0   0.223  -10.4587  -0.5367  -0.1252
 0GV  H41  H  HCH3  0   0.222   -9.2948  -1.8561  -0.0130
 0GV  H42  H  HCH3  0   0.210   -8.7787   1.6629   1.2954
 0GV  H43  H  HCH3  0   0.226   -7.9749   2.2632  -0.1540
 0GV  H44  H  HCH3  0   0.224   -9.6832   1.8537  -0.2052

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
 0GV  C27  C25  single  1.526  0.020  1.526
 0GV  C25  C24  single  1.530  0.020  1.530
 0GV  C25  C26  single  1.526  0.020  1.526
 0GV  C24  C23  single  1.525  0.020  1.525
 0GV  C23  C22  single  1.525  0.020  1.525
 0GV  C22  C20  single  1.536  0.020  1.536
 0GV  C20  C21  single  1.526  0.020  1.526
 0GV  C20  C17  single  1.536  0.020  1.536
 0GV  C16  C17  single  1.551  0.020  1.551
 0GV  C16  C15  single  1.540  0.020  1.540
 0GV  C17  C13  single  1.548  0.020  1.548
 0GV  C15  C14  single  1.527  0.020  1.527
 0GV  C13  C14  single  1.544  0.020  1.544
 0GV  C13  C12  single  1.526  0.020  1.526
 0GV  C13  C18  single  1.533  0.020  1.533
 0GV  C14  C8   single  1.525  0.020  1.525
 0GV  C12  C11  single  1.525  0.020  1.525
 0GV  O7   C7   double  1.218  0.020  1.218
 0GV  C8   C7   single  1.513  0.020  1.513
 0GV  C8   C9   single  1.545  0.020  1.545
 0GV  C7   C6   single  1.463  0.020  1.463
 0GV  C11  C9   single  1.531  0.020  1.531
 0GV  C9   C10  single  1.549  0.020  1.549
 0GV  C6   C5   double  1.340  0.020  1.340
 0GV  C10  C5   single  1.513  0.020  1.513
 0GV  C10  C1   single  1.544  0.020  1.544
 0GV  C10  C19  single  1.538  0.020  1.538
 0GV  C5   C4   single  1.500  0.020  1.500
 0GV  C1   C2   single  1.523  0.020  1.523
 0GV  C4   C3   single  1.529  0.020  1.529
 0GV  C3   C2   single  1.515  0.020  1.515
 0GV  C3   O1   single  1.410  0.020  1.410
 0GV  C11  H1   single  0.970  0.020  1.090
 0GV  C11  H2   single  0.970  0.020  1.090
 0GV  C12  H3   single  0.970  0.020  1.090
 0GV  C12  H4   single  0.970  0.020  1.090
 0GV  C14  H5   single  0.970  0.020  1.090
 0GV  C15  H6   single  0.970  0.020  1.090
 0GV  C15  H7   single  0.970  0.020  1.090
 0GV  C16  H8   single  0.970  0.020  1.090
 0GV  C16  H9   single  0.970  0.020  1.090
 0GV  C17  H10  single  0.970  0.020  1.090
 0GV  C18  H11  single  0.970  0.020  1.090
 0GV  C18  H12  single  0.970  0.020  1.090
 0GV  C18  H13  single  0.970  0.020  1.090
 0GV  C9   H14  single  0.970  0.020  1.090
 0GV  C19  H15  single  0.970  0.020  1.090
 0GV  C19  H16  single  0.970  0.020  1.090
 0GV  C19  H17  single  0.970  0.020  1.090
 0GV  C1   H18  single  0.970  0.020  1.090
 0GV  C1   H19  single  0.970  0.020  1.090
 0GV  C2   H20  single  0.970  0.020  1.090
 0GV  C2   H21  single  0.970  0.020  1.090
 0GV  C3   H22  single  0.970  0.020  1.090
 0GV  O1   H23  single  0.850  0.020  0.980
 0GV  C4   H24  single  0.970  0.020  1.090
 0GV  C4   H25  single  0.970  0.020  1.090
 0GV  C6   H26  single  0.930  0.020  1.080
 0GV  C8   H27  single  0.970  0.020  1.090
 0GV  C20  H28  single  0.970  0.020  1.090
 0GV  C21  H29  single  0.970  0.020  1.090
 0GV  C21  H30  single  0.970  0.020  1.090
 0GV  C21  H31  single  0.970  0.020  1.090
 0GV  C22  H32  single  0.970  0.020  1.090
 0GV  C22  H33  single  0.970  0.020  1.090
 0GV  C23  H34  single  0.970  0.020  1.090
 0GV  C23  H35  single  0.970  0.020  1.090
 0GV  C24  H36  single  0.970  0.020  1.090
 0GV  C24  H37  single  0.970  0.020  1.090
 0GV  C25  H38  single  0.970  0.020  1.090
 0GV  C26  H39  single  0.970  0.020  1.090
 0GV  C26  H40  single  0.970  0.020  1.090
 0GV  C26  H41  single  0.970  0.020  1.090
 0GV  C27  H42  single  0.970  0.020  1.090
 0GV  C27  H43  single  0.970  0.020  1.090
 0GV  C27  H44  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
 0GV  C5   C10  C1   108.78  3.000
 0GV  C1   C10  C19  109.84  3.000
 0GV  C5   C10  C19  107.62  3.000
 0GV  C19  C10  C9   112.18  3.000
 0GV  C1   C10  C9   108.71  3.000
 0GV  C5   C10  C9   109.65  3.000
 0GV  H2   C11  H1   105.65  3.000
 0GV  H2   C11  C9   108.96  3.000
 0GV  H1   C11  C9   110.76  3.000
 0GV  H2   C11  C12  108.78  3.000
 0GV  H1   C11  C12  108.78  3.000
 0GV  C9   C11  C12  113.60  3.000
 0GV  H4   C12  H3   106.20  3.000
 0GV  H4   C12  C13  112.14  3.000
 0GV  H3   C12  C13  108.61  3.000
 0GV  H4   C12  C11  108.70  3.000
 0GV  H3   C12  C11  109.86  3.000
 0GV  C13  C12  C11  111.19  3.000
 0GV  C18  C13  C17  110.12  3.000
 0GV  C18  C13  C14  111.64  3.000
 0GV  C17  C13  C14  100.41  3.000
 0GV  C18  C13  C12  111.22  3.000
 0GV  C14  C13  C12  107.03  3.000
 0GV  C17  C13  C12  115.90  3.000
 0GV  H5   C14  C8   106.97  3.000
 0GV  H5   C14  C15  107.24  3.000
 0GV  C8   C14  C15  119.30  3.000
 0GV  H5   C14  C13  105.92  3.000
 0GV  C8   C14  C13  113.27  3.000
 0GV  C15  C14  C13  103.30  3.000
 0GV  H7   C15  H6   106.78  3.000
 0GV  H7   C15  C16  112.21  3.000
 0GV  H6   C15  C16  111.23  3.000
 0GV  H7   C15  C14  112.53  3.000
 0GV  H6   C15  C14  110.57  3.000
 0GV  C16  C15  C14  103.60  3.000
 0GV  H9   C16  H8   106.08  3.000
 0GV  H9   C16  C17  111.10  3.000
 0GV  H8   C16  C17  110.24  3.000
 0GV  H9   C16  C15  110.99  3.000
 0GV  H8   C16  C15  111.29  3.000
 0GV  C17  C16  C15  107.19  3.000
 0GV  H10  C17  C20  107.13  3.000
 0GV  H10  C17  C16  108.45  3.000
 0GV  C20  C17  C16  111.99  3.000
 0GV  H10  C17  C13  106.40  3.000
 0GV  C16  C17  C13  103.31  3.000
 0GV  C20  C17  C13  119.07  3.000
 0GV  H13  C18  H12  106.51  3.000
 0GV  H13  C18  H11  106.77  3.000
 0GV  H12  C18  H11  107.03  3.000
 0GV  H13  C18  C13  112.89  3.000
 0GV  H12  C18  C13  111.13  3.000
 0GV  H11  C18  C13  112.14  3.000
 0GV  H14  C9   C8   105.83  3.000
 0GV  H14  C9   C11  106.19  3.000
 0GV  C8   C9   C11  113.18  3.000
 0GV  H14  C9   C10  105.90  3.000
 0GV  C11  C9   C10  112.86  3.000
 0GV  C8   C9   C10  112.14  3.000
 0GV  H17  C19  H16  106.90  3.000
 0GV  H17  C19  H15  107.16  3.000
 0GV  H16  C19  H15  108.08  3.000
 0GV  H17  C19  C10  111.43  3.000
 0GV  H16  C19  C10  111.07  3.000
 0GV  H15  C19  C10  111.95  3.000
 0GV  H19  C1   H18  106.37  3.000
 0GV  H19  C1   C2   108.75  3.000
 0GV  H18  C1   C2   109.07  3.000
 0GV  H19  C1   C10  108.44  3.000
 0GV  H18  C1   C10  109.18  3.000
 0GV  C2   C1   C10  114.70  3.000
 0GV  H21  C2   H20  106.81  3.000
 0GV  H21  C2   C3   110.12  3.000
 0GV  H20  C2   C3   109.58  3.000
 0GV  H21  C2   C1   109.20  3.000
 0GV  H20  C2   C1   110.78  3.000
 0GV  C3   C2   C1   110.30  3.000
 0GV  H22  C3   C4   108.20  3.000
 0GV  H22  C3   O1   110.44  3.000
 0GV  C4   C3   O1   111.48  3.000
 0GV  H22  C3   C2   108.34  3.000
 0GV  O1   C3   C2   108.89  3.000
 0GV  C4   C3   C2   109.43  3.000
 0GV  H23  O1   C3   108.35  3.000
 0GV  H25  C4   H24  106.84  3.000
 0GV  H25  C4   C5   109.70  3.000
 0GV  H24  C4   C5   109.01  3.000
 0GV  H25  C4   C3   110.62  3.000
 0GV  H24  C4   C3   107.98  3.000
 0GV  C5   C4   C3   112.50  3.000
 0GV  C6   C5   C4   120.01  3.000
 0GV  C4   C5   C10  117.58  3.000
 0GV  C6   C5   C10  122.40  3.000
 0GV  H26  C6   C7   116.17  3.000
 0GV  H26  C6   C5   119.94  3.000
 0GV  C7   C6   C5   123.87  3.000
 0GV  C8   C7   O7   123.55  3.000
 0GV  C8   C7   C6   116.40  3.000
 0GV  O7   C7   C6   120.03  3.000
 0GV  H27  C8   C7   105.35  3.000
 0GV  H27  C8   C9   109.23  3.000
 0GV  C7   C8   C9   107.84  3.000
 0GV  H27  C8   C14  109.13  3.000
 0GV  C9   C8   C14  111.50  3.000
 0GV  C7   C8   C14  113.55  3.000
 0GV  H28  C20  C22  107.30  3.000
 0GV  H28  C20  C21  108.18  3.000
 0GV  C22  C20  C21  110.21  3.000
 0GV  H28  C20  C17  107.62  3.000
 0GV  C21  C20  C17  113.57  3.000
 0GV  C22  C20  C17  109.74  3.000
 0GV  H31  C21  H30  106.50  3.000
 0GV  H31  C21  H29  107.47  3.000
 0GV  H30  C21  H29  107.73  3.000
 0GV  H31  C21  C20  111.41  3.000
 0GV  H30  C21  C20  112.30  3.000
 0GV  H29  C21  C20  111.17  3.000
 0GV  H33  C22  H32  105.73  3.000
 0GV  H33  C22  C23  109.45  3.000
 0GV  H32  C22  C23  107.75  3.000
 0GV  H33  C22  C20  108.85  3.000
 0GV  H32  C22  C20  109.63  3.000
 0GV  C23  C22  C20  115.02  3.000
 0GV  H35  C23  H34  106.05  3.000
 0GV  H35  C23  C24  109.16  3.000
 0GV  H34  C23  C24  109.57  3.000
 0GV  H35  C23  C22  109.14  3.000
 0GV  H34  C23  C22  110.39  3.000
 0GV  C24  C23  C22  112.31  3.000
 0GV  H37  C24  H36  105.85  3.000
 0GV  H37  C24  C25  109.00  3.000
 0GV  H36  C24  C25  108.60  3.000
 0GV  H37  C24  C23  109.41  3.000
 0GV  H36  C24  C23  108.71  3.000
 0GV  C25  C24  C23  114.88  3.000
 0GV  H38  C25  C27  108.12  3.000
 0GV  H38  C25  C26  107.92  3.000
 0GV  C27  C25  C26  110.24  3.000
 0GV  H38  C25  C24  107.68  3.000
 0GV  C26  C25  C24  110.41  3.000
 0GV  C27  C25  C24  112.31  3.000
 0GV  H41  C26  H40  107.70  3.000
 0GV  H41  C26  H39  107.65  3.000
 0GV  H40  C26  H39  107.52  3.000
 0GV  H41  C26  C25  111.54  3.000
 0GV  H40  C26  C25  111.42  3.000
 0GV  H39  C26  C25  110.82  3.000
 0GV  H44  C27  H43  107.32  3.000
 0GV  H44  C27  H42  107.57  3.000
 0GV  H43  C27  H42  107.66  3.000
 0GV  H44  C27  C25  111.04  3.000
 0GV  H43  C27  C25  112.32  3.000
 0GV  H42  C27  C25  110.73  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
 0GV  Var_01  C7   C6   C5   C10     3.15  30.0  1
 0GV  Var_02  C3   C4   C5   C10    49.68  30.0  1
 0GV  Var_03  C3   C2   C1   C10   -57.65  30.0  1
 0GV  Var_04  C9   C11  C12  C13   -55.39  30.0  1
 0GV  Var_05  C17  C16  C15  C14    11.16  30.0  1
 0GV  Var_06  C8   C7   C6   C5      8.58  30.0  1
 0GV  Var_07  C24  C23  C22  C20   176.88  30.0  1
 0GV  Var_08  C25  C24  C23  C22  -177.47  30.0  1
 0GV  Var_09  C27  C25  C24  C23   -64.22  30.0  1
 0GV  Var_10  H42  C27  C25  C24   -60.77  30.0  3
 0GV  Var_11  H39  C26  C25  C24    61.91  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
 0GV  chir_01  C10  C5   C1   C9   positiv
 0GV  chir_02  C13  C12  C14  C17  negativ
 0GV  chir_03  C14  C15  C13  C8   positiv
 0GV  chir_04  C17  C13  C16  C20  positiv
 0GV  chir_05  C9   C10  C11  C8   negativ
 0GV  chir_06  C3   O1   C2   C4   negativ
 0GV  chir_07  C8   C14  C7   C9   positiv
 0GV  chir_08  C20  C22  C21  C17  negativ

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
 0GV  plan-1  C6  0.020
 0GV  plan-1  C7  0.020
 0GV  plan-1  O7  0.020
 0GV  plan-1  C8  0.020

