# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Jul 30 05:52:46 2021
#   Inital geometry file: a 133 line input string
#   Ligand name: (3~{S},5~{R},8~{R},9~{S},10~{S},13~{S},14~{S},17~{S})-17-(furan-3-yl)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,15,16-dodecahydro-1~{H}-cyclopenta[a]phenanthrene-3,14,17-triol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@]12CC[C@H](O)C[C@H]1CC[C@@H]3[C@@H]2CC[C@@]4(C)[C@]3(O)CC[C@]4(O)c5cocc5
#
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
 E4R  E4R  (3~{S},5~{R},8~{R},9~{S},10~{S},13~{S},14~{S},17~{S})-17-(furan-3-yl)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,15,16-dodecahydro-1~{H}-cyclopenta[a]phenanthrene-3,14,17-triol  ligand  61  27  .  2022-03-18  2022-03-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_E4R
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
 E4R  C1   C  CH2   0  -0.408  -1.0879  -22.2323  49.0602
 E4R  C2   C  CH2   0  -0.485  -1.9989  -21.0229  48.9056
 E4R  C3   C  CH1   0   0.048  -1.3928  -19.9840  47.9692
 E4R  O2   O  OH1   0  -0.668  -0.4796  -20.7422  55.9392
 E4R  C4   C  CH2   0  -0.450   0.0069  -19.6174  48.4318
 E4R  C5   C  CH1   0  -0.201   0.9305  -20.8267  48.6274
 E4R  C6   C  CH2   0  -0.434   2.3088  -20.3801  49.1104
 E4R  C7   C  CH2   0  -0.433   2.2745  -19.8459  50.5362
 E4R  C8   C  CH1   0  -0.241   1.6573  -20.8499  51.5152
 E4R  C9   C  CH1   0  -0.211   0.2964  -21.3668  51.0242
 E4R  C10  C  CT    0  -0.060   0.3285  -21.8984  49.5661
 E4R  C11  C  CH2   0  -0.441  -0.2367  -22.3764  52.0341
 E4R  C12  C  CH2   0  -0.414  -0.4195  -21.7281  53.3962
 E4R  C13  C  CT    0  -0.124   0.8878  -21.1633  53.9900
 E4R  C14  C  CT    0   0.308   1.5937  -20.2557  52.9379
 E4R  C15  C  CH2   0  -0.497   0.7995  -18.9254  53.0164
 E4R  C16  C  CH2   0  -0.509   0.0164  -18.9330  54.3367
 E4R  C17  C  CT    0   0.225   0.5159  -20.1557  55.1277
 E4R  C18  C  CH3   0  -0.666   1.7526  -22.3293  54.4571
 E4R  C19  C  CH3   0  -0.671   1.1517  -23.1879  49.4628
 E4R  C20  C  CR5   0  -0.038   1.6704  -19.7827  56.0284
 E4R  C21  C  CR15  0  -0.366   2.2471  -20.6030  57.0573
 E4R  C22  C  CR15  0  -0.053   2.3134  -18.5886  56.1281
 E4R  C24  C  CR15  0   0.013   3.1856  -19.8481  57.6671
 E4R  O14  O  OH1   0  -0.688   2.9576  -20.0490  53.2760
 E4R  O23  O  O     0  -0.395   3.2383  -18.6218  57.1087
 E4R  O3   O  OH1   0  -0.679  -1.2972  -20.4695  46.6399
 E4R  H1   H  HCH2  0   0.226  -1.5613  -22.9719  49.7097
 E4R  H2   H  HCH2  0   0.217  -0.9882  -22.7200  48.0849
 E4R  H3   H  HCH2  0   0.223  -2.1952  -20.5569  49.8753
 E4R  H4   H  HCH2  0   0.233  -2.9782  -21.3373  48.5284
 E4R  H5   H  HCH1  0   0.205  -2.0181  -19.0795  47.9909
 E4R  H6   H  HOH1  0   0.447  -0.6922  -20.1254  56.6477
 E4R  H7   H  HCH2  0   0.230   0.4644  -18.9324  47.7104
 E4R  H8   H  HCH2  0   0.221  -0.0915  -19.0447  49.3575
 E4R  H9   H  HCH1  0   0.213   1.0554  -21.2967  47.6446
 E4R  H10  H  HCH2  0   0.221   3.0121  -21.2153  49.0487
 E4R  H11  H  HCH2  0   0.221   2.6998  -19.6091  48.4393
 E4R  H12  H  HCH2  0   0.231   3.2843  -19.5843  50.8544
 E4R  H13  H  HCH2  0   0.219   1.7013  -18.9143  50.5544
 E4R  H14  H  HCH1  0   0.216   2.3372  -21.7106  51.5773
 E4R  H15  H  HCH1  0   0.211  -0.3937  -20.5132  51.0422
 E4R  H16  H  HCH2  0   0.233  -1.2038  -22.7739  51.7174
 E4R  H17  H  HCH2  0   0.218   0.4333  -23.2383  52.0968
 E4R  H18  H  HCH2  0   0.227  -1.1716  -20.9433  53.2797
 E4R  H19  H  HCH2  0   0.233  -0.8467  -22.4507  54.0940
 E4R  H20  H  HCH2  0   0.245   1.4848  -18.0790  52.9434
 E4R  H21  H  HCH2  0   0.242   0.1076  -18.8271  52.1773
 E4R  H22  H  HCH2  0   0.245   0.1122  -18.0020  54.8971
 E4R  H23  H  HCH2  0   0.255  -1.0506  -19.0564  54.1497
 E4R  H24  H  HCH3  0   0.225   1.2412  -22.8918  55.2408
 E4R  H25  H  HCH3  0   0.234   1.9479  -23.0289  53.6431
 E4R  H26  H  HCH3  0   0.233   2.7178  -22.0170  54.8495
 E4R  H27  H  HCH3  0   0.227   0.6752  -24.0086  50.0014
 E4R  H28  H  HCH3  0   0.223   1.2361  -23.4953  48.4178
 E4R  H29  H  HCH3  0   0.228   2.1644  -23.0892  49.8527
 E4R  H30  H  HCR5  0   0.267   1.9900  -21.6197  57.3033
 E4R  H31  H  HCR5  0   0.292   2.2179  -17.6534  55.5982
 E4R  H32  H  HCR5  0   0.284   3.8642  -20.0392  58.4828
 E4R  H33  H  HOH1  0   0.447   3.0118  -19.6242  54.1383
 E4R  H34  H  HOH1  0   0.444  -2.1688  -20.7719  46.3665

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
 E4R  O3   C3   single    1.418  0.020  1.418
 E4R  C3   C4   single    1.519  0.020  1.519
 E4R  C3   C2   single    1.524  0.020  1.524
 E4R  C4   C5   single    1.534  0.020  1.534
 E4R  C5   C6   single    1.527  0.020  1.527
 E4R  C5   C10  single    1.547  0.020  1.547
 E4R  C2   C1   single    1.522  0.020  1.522
 E4R  C1   C10  single    1.541  0.020  1.541
 E4R  C6   C7   single    1.523  0.020  1.523
 E4R  C19  C10  single    1.533  0.020  1.533
 E4R  C10  C9   single    1.552  0.020  1.552
 E4R  C7   C8   single    1.532  0.020  1.532
 E4R  C9   C8   single    1.536  0.020  1.536
 E4R  C9   C11  single    1.524  0.020  1.524
 E4R  C8   C14  single    1.543  0.020  1.543
 E4R  C11  C12  single    1.520  0.020  1.520
 E4R  C14  C15  single    1.551  0.020  1.551
 E4R  C14  O14  single    1.420  0.020  1.420
 E4R  C14  C13  single    1.559  0.020  1.559
 E4R  C15  C16  single    1.535  0.020  1.535
 E4R  C12  C13  single    1.543  0.020  1.543
 E4R  C13  C18  single    1.525  0.020  1.525
 E4R  C13  C17  single    1.565  0.020  1.565
 E4R  C16  C17  single    1.540  0.020  1.540
 E4R  C17  O2   single    1.412  0.020  1.412
 E4R  C17  C20  single    1.511  0.020  1.511
 E4R  C22  C20  aromatic  1.360  0.020  1.360
 E4R  C22  O23  aromatic  1.348  0.020  1.348
 E4R  C20  C21  aromatic  1.437  0.020  1.437
 E4R  O23  C24  aromatic  1.348  0.020  1.348
 E4R  C21  C24  aromatic  1.350  0.020  1.350
 E4R  C1   H1   single    0.970  0.020  1.090
 E4R  C1   H2   single    0.970  0.020  1.090
 E4R  C2   H3   single    0.970  0.020  1.090
 E4R  C2   H4   single    0.970  0.020  1.090
 E4R  C3   H5   single    0.970  0.020  1.090
 E4R  O2   H6   single    0.850  0.020  0.980
 E4R  C4   H7   single    0.970  0.020  1.090
 E4R  C4   H8   single    0.970  0.020  1.090
 E4R  C5   H9   single    0.970  0.020  1.090
 E4R  C6   H10  single    0.970  0.020  1.090
 E4R  C6   H11  single    0.970  0.020  1.090
 E4R  C7   H12  single    0.970  0.020  1.090
 E4R  C7   H13  single    0.970  0.020  1.090
 E4R  C8   H14  single    0.970  0.020  1.090
 E4R  C9   H15  single    0.970  0.020  1.090
 E4R  C11  H16  single    0.970  0.020  1.090
 E4R  C11  H17  single    0.970  0.020  1.090
 E4R  C12  H18  single    0.970  0.020  1.090
 E4R  C12  H19  single    0.970  0.020  1.090
 E4R  C15  H20  single    0.970  0.020  1.090
 E4R  C15  H21  single    0.970  0.020  1.090
 E4R  C16  H22  single    0.970  0.020  1.090
 E4R  C16  H23  single    0.970  0.020  1.090
 E4R  C18  H24  single    0.970  0.020  1.090
 E4R  C18  H25  single    0.970  0.020  1.090
 E4R  C18  H26  single    0.970  0.020  1.090
 E4R  C19  H27  single    0.970  0.020  1.090
 E4R  C19  H28  single    0.970  0.020  1.090
 E4R  C19  H29  single    0.970  0.020  1.090
 E4R  C21  H30  single    0.930  0.020  1.080
 E4R  C22  H31  single    0.930  0.020  1.080
 E4R  C24  H32  single    0.930  0.020  1.080
 E4R  O14  H33  single    0.850  0.020  0.980
 E4R  O3   H34  single    0.850  0.020  0.980

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
 E4R  H2   C1   H1   105.51  3.000
 E4R  H2   C1   C10  107.78  3.000
 E4R  H1   C1   C10  110.49  3.000
 E4R  H2   C1   C2   108.54  3.000
 E4R  H1   C1   C2   109.82  3.000
 E4R  C10  C1   C2   114.30  3.000
 E4R  H4   C2   H3   105.49  3.000
 E4R  H4   C2   C3   109.85  3.000
 E4R  H3   C2   C3   109.01  3.000
 E4R  H4   C2   C1   110.00  3.000
 E4R  H3   C2   C1   110.85  3.000
 E4R  C3   C2   C1   111.47  3.000
 E4R  H5   C3   O3   109.77  3.000
 E4R  H5   C3   C4   108.63  3.000
 E4R  O3   C3   C4   107.81  3.000
 E4R  H5   C3   C2   108.80  3.000
 E4R  C4   C3   C2   110.11  3.000
 E4R  O3   C3   C2   111.67  3.000
 E4R  H6   O2   C17  108.20  3.000
 E4R  H8   C4   H7   105.54  3.000
 E4R  H8   C4   C5   111.05  3.000
 E4R  H7   C4   C5   109.00  3.000
 E4R  H8   C4   C3   107.55  3.000
 E4R  H7   C4   C3   109.59  3.000
 E4R  C5   C4   C3   113.78  3.000
 E4R  H9   C5   C10  106.94  3.000
 E4R  H9   C5   C6   107.81  3.000
 E4R  C10  C5   C6   111.22  3.000
 E4R  H9   C5   C4   106.99  3.000
 E4R  C10  C5   C4   112.91  3.000
 E4R  C6   C5   C4   110.68  3.000
 E4R  H11  C6   H10  105.88  3.000
 E4R  H11  C6   C7   109.57  3.000
 E4R  H10  C6   C7   109.58  3.000
 E4R  H11  C6   C5   109.55  3.000
 E4R  H10  C6   C5   109.83  3.000
 E4R  C7   C6   C5   112.23  3.000
 E4R  H13  C7   H12  106.02  3.000
 E4R  H13  C7   C8   109.65  3.000
 E4R  H12  C7   C8   110.10  3.000
 E4R  H13  C7   C6   109.03  3.000
 E4R  H12  C7   C6   109.66  3.000
 E4R  C8   C7   C6   112.17  3.000
 E4R  H14  C8   C14  105.97  3.000
 E4R  H14  C8   C9   107.61  3.000
 E4R  C14  C8   C9   112.81  3.000
 E4R  H14  C8   C7   107.47  3.000
 E4R  C14  C8   C7   110.70  3.000
 E4R  C9   C8   C7   111.91  3.000
 E4R  H15  C9   C11  106.52  3.000
 E4R  H15  C9   C10  107.14  3.000
 E4R  C11  C9   C10  113.75  3.000
 E4R  H15  C9   C8   106.85  3.000
 E4R  C11  C9   C8   108.72  3.000
 E4R  C10  C9   C8   113.40  3.000
 E4R  C19  C10  C9   111.25  3.000
 E4R  C9   C10  C5   109.93  3.000
 E4R  C19  C10  C5   109.45  3.000
 E4R  C9   C10  C1   111.32  3.000
 E4R  C19  C10  C1   106.81  3.000
 E4R  C5   C10  C1   107.98  3.000
 E4R  H17  C11  H16  105.80  3.000
 E4R  H17  C11  C12  111.01  3.000
 E4R  H16  C11  C12  107.97  3.000
 E4R  H17  C11  C9   110.23  3.000
 E4R  H16  C11  C9   111.01  3.000
 E4R  C12  C11  C9   110.70  3.000
 E4R  H19  C12  H18  105.91  3.000
 E4R  H19  C12  C13  109.13  3.000
 E4R  H18  C12  C13  111.16  3.000
 E4R  H19  C12  C11  109.74  3.000
 E4R  H18  C12  C11  107.07  3.000
 E4R  C13  C12  C11  113.53  3.000
 E4R  C18  C13  C17  113.86  3.000
 E4R  C17  C13  C14  102.92  3.000
 E4R  C18  C13  C14  113.28  3.000
 E4R  C17  C13  C12  108.31  3.000
 E4R  C18  C13  C12  108.57  3.000
 E4R  C14  C13  C12  109.70  3.000
 E4R  O14  C14  C15  110.78  3.000
 E4R  O14  C14  C13  111.03  3.000
 E4R  C15  C14  C13  103.49  3.000
 E4R  C13  C14  C8   114.64  3.000
 E4R  O14  C14  C8   103.65  3.000
 E4R  C15  C14  C8   113.45  3.000
 E4R  H21  C15  H20  106.06  3.000
 E4R  H21  C15  C16  109.76  3.000
 E4R  H20  C15  C16  112.43  3.000
 E4R  H21  C15  C14  111.27  3.000
 E4R  H20  C15  C14  109.88  3.000
 E4R  C16  C15  C14  107.48  3.000
 E4R  H23  C16  H22  105.71  3.000
 E4R  H23  C16  C17  108.41  3.000
 E4R  H22  C16  C17  112.67  3.000
 E4R  H23  C16  C15  110.62  3.000
 E4R  H22  C16  C15  113.13  3.000
 E4R  C17  C16  C15  106.28  3.000
 E4R  C20  C17  C16  110.99  3.000
 E4R  C20  C17  C13  114.26  3.000
 E4R  C16  C17  C13  102.42  3.000
 E4R  C20  C17  O2   107.37  3.000
 E4R  C16  C17  O2   113.36  3.000
 E4R  C13  C17  O2   108.54  3.000
 E4R  H26  C18  H25  107.12  3.000
 E4R  H26  C18  H24  107.74  3.000
 E4R  H25  C18  H24  106.80  3.000
 E4R  H26  C18  C13  113.22  3.000
 E4R  H25  C18  C13  111.31  3.000
 E4R  H24  C18  C13  110.37  3.000
 E4R  H29  C19  H28  107.21  3.000
 E4R  H29  C19  H27  107.29  3.000
 E4R  H28  C19  H27  107.11  3.000
 E4R  H29  C19  C10  113.50  3.000
 E4R  H28  C19  C10  110.03  3.000
 E4R  H27  C19  C10  111.40  3.000
 E4R  C22  C20  C21  105.02  3.000
 E4R  C21  C20  C17  126.35  3.000
 E4R  C22  C20  C17  128.44  3.000
 E4R  H30  C21  C24  126.19  3.000
 E4R  H30  C21  C20  127.35  3.000
 E4R  C24  C21  C20  106.46  3.000
 E4R  H31  C22  O23  116.05  3.000
 E4R  H31  C22  C20  133.09  3.000
 E4R  O23  C22  C20  110.85  3.000
 E4R  H32  C24  O23  116.74  3.000
 E4R  H32  C24  C21  132.86  3.000
 E4R  O23  C24  C21  110.40  3.000
 E4R  H33  O14  C14  109.36  3.000
 E4R  C24  O23  C22  107.26  3.000
 E4R  H34  O3   C3   108.22  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
 E4R  CONST_01  C24  O23  C22  C20    0.00   0.0  0
 E4R  CONST_02  O23  C24  C21  C20    0.00   0.0  0
 E4R  CONST_03  O23  C22  C20  C21    0.00   0.0  0
 E4R  CONST_04  C22  O23  C24  C21    0.00   0.0  0
 E4R  CONST_05  C24  C21  C20  C22    0.00   0.0  0
 E4R  CONST_06  O23  C22  C20  C17  180.00   0.0  0
 E4R  CONST_07  C24  C21  C20  C17  180.00   0.0  0
 E4R  CONST_08  H31  C22  C20  C17    0.00   0.0  0
 E4R  CONST_09  H30  C21  C20  C17    0.00   0.0  0
 E4R  CONST_10  H32  C24  C21  C20  180.00   0.0  0
 E4R  Var_01    C10  C1   C2   C3    56.98  30.0  1
 E4R  Var_02    C8   C7   C6   C5    54.65  30.0  1
 E4R  Var_03    C13  C12  C11  C9   -60.31  30.0  1
 E4R  Var_04    C17  C16  C15  C14    8.56  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
 E4R  chir_01  C3   O3   C4   C2   positiv
 E4R  chir_02  C5   C4   C6   C10  negativ
 E4R  chir_03  C8   C7   C9   C14  positiv
 E4R  chir_04  C9   C10  C8   C11  positiv
 E4R  chir_05  C10  C9   C1   C5   negativ
 E4R  chir_06  C13  C12  C14  C17  negativ
 E4R  chir_07  C14  C8   C15  C13  negativ
 E4R  chir_08  C17  C13  C16  C20  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
 E4R  plan-1  C17  0.020
 E4R  plan-1  C20  0.020
 E4R  plan-1  C21  0.020
 E4R  plan-1  C22  0.020
 E4R  plan-1  C24  0.020
 E4R  plan-1  O23  0.020
 E4R  plan-1  H30  0.020
 E4R  plan-1  H31  0.020
 E4R  plan-1  H32  0.020

