# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Mar 18 13:24:55 2022
#   Inital geometry file: a 157 line input string
#   Ligand name: (3beta,5beta,9beta)-3-(acetyloxy)cholan-24-oic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@H](CCC(O)=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](CC[C@]4(C)[C@H]3CC[C@]12C)OC(C)=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
 LOA  LOA  '(3beta,5beta,9beta)-3-(acetyloxy)cholan-24-oic acid'  ligand  71  30  .  2022-03-22  2022-03-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_LOA
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
 LOA  C1   C  CH2    0  -0.434  -3.5972  -0.3922   1.8621
 LOA  C2   C  CH2    0  -0.468  -4.0864   0.8465   1.1220
 LOA  C3   C  CH1    0   0.064  -4.8980   0.4105  -0.0845
 LOA  O3   O  O2     0  -0.469  -5.3093   1.5426  -0.8756
 LOA  C4   C  CH2    0  -0.456  -4.0798  -0.4836  -0.9955
 LOA  C5   C  CH1    0  -0.215  -3.5326  -1.7116  -0.2555
 LOA  C6   C  CH2    0  -0.434  -2.7177  -2.5865  -1.2073
 LOA  C7   C  CH2    0  -0.426  -1.3871  -1.9476  -1.5843
 LOA  C8   C  CH1    0  -0.219  -0.5696  -1.5758  -0.3510
 LOA  C9   C  CH1    0  -0.190  -1.3869  -0.6792   0.5999
 LOA  C10  C  CT     0  -0.063  -2.7294  -1.3387   1.0158
 LOA  C11  C  CH2    0  -0.440  -0.5406  -0.1936   1.7816
 LOA  C12  C  CH2    0  -0.410   0.7842   0.4481   1.3589
 LOA  C13  C  CT     0  -0.053   1.6111  -0.4784   0.4672
 LOA  C14  C  CH1    0  -0.172   0.7142  -0.8524  -0.7268
 LOA  C15  C  CH2    0  -0.448   1.6631  -1.5218  -1.7135
 LOA  C16  C  CH2    0  -0.447   2.9897  -0.7621  -1.5156
 LOA  C17  C  CH1    0  -0.156   2.8068   0.1629  -0.2819
 LOA  C18  C  CH3    0  -0.686   2.0761  -1.7100   1.2509
 LOA  C19  C  CH3    0  -0.667  -2.4947  -2.5938   1.8636
 LOA  C20  C  CH1    0  -0.231   4.1248   0.4081   0.4688
 LOA  C21  C  CH3    0  -0.671   3.9409   1.2615   1.7214
 LOA  C22  C  CH2    0  -0.394   5.1506   1.0486  -0.4785
 LOA  C23  C  CH2    0  -0.595   6.5527   1.1758   0.0979
 LOA  C24  C  C      0   0.414   7.6387   1.6644  -0.8782
 LOA  C25  C  CH3    0  -0.777  -6.6844   3.3491  -1.4808
 LOA  C26  C  C      0   0.567  -6.4025   2.2128  -0.5402
 LOA  OT1  O  O      0  -0.610   7.2907   1.9961  -2.0288
 LOA  OT2  O  OC    -1  -0.636   8.8028   1.6975  -0.4233
 LOA  O25  O  O      0  -0.463  -7.0976   1.9409   0.4089
 LOA  H1   H  HCH2   0   0.238  -3.0676  -0.0980   2.7706
 LOA  H2   H  HCH2   0   0.224  -4.4732  -0.9561   2.2045
 LOA  H3   H  HCH2   0   0.245  -4.6917   1.4599   1.7929
 LOA  H4   H  HCH2   0   0.228  -3.2428   1.4631   0.7960
 LOA  H5   H  HCH1   0   0.228  -5.7871  -0.1309   0.2545
 LOA  H6   H  HCH2   0   0.241  -4.6979  -0.8263  -1.8306
 LOA  H7   H  HCH2   0   0.229  -3.2672   0.1028  -1.4325
 LOA  H8   H  HCH1   0   0.217  -4.4028  -2.2948   0.0753
 LOA  H9   H  HCH2   0   0.224  -2.5266  -3.5566  -0.7395
 LOA  H10  H  HCH2   0   0.224  -3.3048  -2.7975  -2.1063
 LOA  H11  H  HCH2   0   0.231  -0.8184  -2.6373  -2.2145
 LOA  H12  H  HCH2   0   0.206  -1.5531  -1.0515  -2.1941
 LOA  H13  H  HCH1   0   0.206  -0.3035  -2.5086   0.1628
 LOA  H14  H  HCH1   0   0.207  -1.6331   0.2215   0.0194
 LOA  H15  H  HCH2   0   0.228  -1.1014   0.5461   2.3590
 LOA  H16  H  HCH2   0   0.215  -0.3428  -1.0177   2.4735
 LOA  H17  H  HCH2   0   0.206   0.5753   1.3701   0.8025
 LOA  H18  H  HCH2   0   0.223   1.3269   0.7491   2.2563
 LOA  H19  H  HCH1   0   0.201   0.4121   0.1041  -1.1832
 LOA  H20  H  HCH2   0   0.213   1.7771  -2.5858  -1.4871
 LOA  H21  H  HCH2   0   0.227   1.3012  -1.4615  -2.7414
 LOA  H22  H  HCH2   0   0.217   3.8165  -1.4587  -1.3519
 LOA  H23  H  HCH2   0   0.227   3.2518  -0.1859  -2.4037
 LOA  H24  H  HCH1   0   0.198   2.4558   1.1425  -0.6386
 LOA  H25  H  HCH3   0   0.230   1.2449  -2.2564   1.6956
 LOA  H26  H  HCH3   0   0.230   2.6237  -2.4171   0.6265
 LOA  H27  H  HCH3   0   0.229   2.7392  -1.4264   2.0699
 LOA  H28  H  HCH3   0   0.224  -3.4481  -3.0714   2.1010
 LOA  H29  H  HCH3   0   0.230  -1.8693  -3.3371   1.3713
 LOA  H30  H  HCH3   0   0.228  -2.0188  -2.3453   2.8133
 LOA  H31  H  HCH1   0   0.196   4.5300  -0.5654   0.7763
 LOA  H32  H  HCH3   0   0.208   3.4526   2.2090   1.4796
 LOA  H33  H  HCH3   0   0.226   3.3379   0.7615   2.4777
 LOA  H34  H  HCH3   0   0.232   4.8977   1.4953   2.1890
 LOA  H35  H  HCH2   0   0.221   5.2120   0.4543  -1.3918
 LOA  H36  H  HCH2   0   0.193   4.7796   2.0330  -0.7859
 LOA  H37  H  HCH2   0   0.221   6.5614   1.8550   0.9566
 LOA  H38  H  HCH2   0   0.212   6.8694   0.2065   0.5019
 LOA  H39  H  HCH3   0   0.258  -5.9477   3.4380  -2.2744
 LOA  H40  H  HCH3   0   0.273  -7.6699   3.2114  -1.9263
 LOA  H41  H  HCH3   0   0.273  -6.7153   4.2829  -0.9193

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
 LOA  C19  C10  single  1.533  0.020  1.533
 LOA  C1   C10  single  1.538  0.020  1.538
 LOA  C1   C2   single  1.524  0.020  1.524
 LOA  C10  C5   single  1.549  0.020  1.549
 LOA  C10  C9   single  1.552  0.020  1.552
 LOA  C5   C6   single  1.528  0.020  1.528
 LOA  C5   C4   single  1.535  0.020  1.535
 LOA  C2   C3   single  1.518  0.020  1.518
 LOA  C6   C7   single  1.523  0.020  1.523
 LOA  O25  C26  double  1.207  0.020  1.207
 LOA  C3   C4   single  1.516  0.020  1.516
 LOA  C3   O3   single  1.441  0.020  1.441
 LOA  C11  C9   single  1.532  0.020  1.532
 LOA  C11  C12  single  1.532  0.020  1.532
 LOA  C9   C8   single  1.541  0.020  1.541
 LOA  C8   C7   single  1.526  0.020  1.526
 LOA  C8   C14  single  1.521  0.020  1.521
 LOA  C18  C13  single  1.532  0.020  1.532
 LOA  C26  O3   single  1.325  0.020  1.325
 LOA  C26  C25  single  1.502  0.020  1.502
 LOA  C12  C13  single  1.529  0.020  1.529
 LOA  C13  C14  single  1.540  0.020  1.540
 LOA  C13  C17  single  1.550  0.020  1.550
 LOA  C14  C15  single  1.524  0.020  1.524
 LOA  C15  C16  single  1.541  0.020  1.541
 LOA  C21  C20  single  1.527  0.020  1.527
 LOA  C17  C20  single  1.536  0.020  1.536
 LOA  C17  C16  single  1.553  0.020  1.553
 LOA  C20  C22  single  1.536  0.020  1.536
 LOA  C22  C23  single  1.521  0.020  1.521
 LOA  C23  C24  single  1.540  0.020  1.540
 LOA  C24  OT1  deloc   1.247  0.020  1.247
 LOA  C24  OT2  deloc   1.250  0.020  1.250
 LOA  C1   H1   single  0.970  0.020  1.090
 LOA  C1   H2   single  0.970  0.020  1.090
 LOA  C2   H3   single  0.970  0.020  1.090
 LOA  C2   H4   single  0.970  0.020  1.090
 LOA  C3   H5   single  0.970  0.020  1.090
 LOA  C4   H6   single  0.970  0.020  1.090
 LOA  C4   H7   single  0.970  0.020  1.090
 LOA  C5   H8   single  0.970  0.020  1.090
 LOA  C6   H9   single  0.970  0.020  1.090
 LOA  C6   H10  single  0.970  0.020  1.090
 LOA  C7   H11  single  0.970  0.020  1.090
 LOA  C7   H12  single  0.970  0.020  1.090
 LOA  C8   H13  single  0.970  0.020  1.090
 LOA  C9   H14  single  0.970  0.020  1.090
 LOA  C11  H15  single  0.970  0.020  1.090
 LOA  C11  H16  single  0.970  0.020  1.090
 LOA  C12  H17  single  0.970  0.020  1.090
 LOA  C12  H18  single  0.970  0.020  1.090
 LOA  C14  H19  single  0.970  0.020  1.090
 LOA  C15  H20  single  0.970  0.020  1.090
 LOA  C15  H21  single  0.970  0.020  1.090
 LOA  C16  H22  single  0.970  0.020  1.090
 LOA  C16  H23  single  0.970  0.020  1.090
 LOA  C17  H24  single  0.970  0.020  1.090
 LOA  C18  H25  single  0.970  0.020  1.090
 LOA  C18  H26  single  0.970  0.020  1.090
 LOA  C18  H27  single  0.970  0.020  1.090
 LOA  C19  H28  single  0.970  0.020  1.090
 LOA  C19  H29  single  0.970  0.020  1.090
 LOA  C19  H30  single  0.970  0.020  1.090
 LOA  C20  H31  single  0.970  0.020  1.090
 LOA  C21  H32  single  0.970  0.020  1.090
 LOA  C21  H33  single  0.970  0.020  1.090
 LOA  C21  H34  single  0.970  0.020  1.090
 LOA  C22  H35  single  0.970  0.020  1.090
 LOA  C22  H36  single  0.970  0.020  1.090
 LOA  C23  H37  single  0.970  0.020  1.090
 LOA  C23  H38  single  0.970  0.020  1.090
 LOA  C25  H39  single  0.970  0.020  1.090
 LOA  C25  H40  single  0.970  0.020  1.090
 LOA  C25  H41  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
 LOA  H2   C1   H1   105.44  3.000
 LOA  H2   C1   C10  107.82  3.000
 LOA  H1   C1   C10  110.48  3.000
 LOA  H2   C1   C2   108.26  3.000
 LOA  H1   C1   C2   109.93  3.000
 LOA  C10  C1   C2   114.47  3.000
 LOA  H4   C2   H3   107.08  3.000
 LOA  H4   C2   C3   109.70  3.000
 LOA  H3   C2   C3   110.69  3.000
 LOA  H4   C2   C1   110.81  3.000
 LOA  H3   C2   C1   109.65  3.000
 LOA  C3   C2   C1   108.92  3.000
 LOA  H5   C3   C4   109.43  3.000
 LOA  H5   C3   O3   109.07  3.000
 LOA  C4   C3   O3   106.71  3.000
 LOA  H5   C3   C2   109.27  3.000
 LOA  O3   C3   C2   111.30  3.000
 LOA  C4   C3   C2   111.00  3.000
 LOA  C26  O3   C3   119.59  3.000
 LOA  H7   C4   H6   106.43  3.000
 LOA  H7   C4   C5   110.92  3.000
 LOA  H6   C4   C5   108.60  3.000
 LOA  H7   C4   C3   108.96  3.000
 LOA  H6   C4   C3   109.78  3.000
 LOA  C5   C4   C3   112.00  3.000
 LOA  H8   C5   C10  106.94  3.000
 LOA  H8   C5   C6   107.82  3.000
 LOA  C10  C5   C6   111.87  3.000
 LOA  H8   C5   C4   106.71  3.000
 LOA  C6   C5   C4   110.36  3.000
 LOA  C10  C5   C4   112.83  3.000
 LOA  H10  C6   H9   105.91  3.000
 LOA  H10  C6   C7   110.25  3.000
 LOA  H9   C6   C7   108.97  3.000
 LOA  H10  C6   C5   109.63  3.000
 LOA  H9   C6   C5   109.54  3.000
 LOA  C7   C6   C5   112.32  3.000
 LOA  H12  C7   H11  105.88  3.000
 LOA  H12  C7   C8   109.36  3.000
 LOA  H11  C7   C8   109.93  3.000
 LOA  H12  C7   C6   110.37  3.000
 LOA  H11  C7   C6   109.41  3.000
 LOA  C8   C7   C6   111.73  3.000
 LOA  H13  C8   C14  108.38  3.000
 LOA  H13  C8   C9   109.52  3.000
 LOA  C14  C8   C9   108.87  3.000
 LOA  H13  C8   C7   107.53  3.000
 LOA  C14  C8   C7   111.62  3.000
 LOA  C9   C8   C7   110.87  3.000
 LOA  H14  C9   C11  105.74  3.000
 LOA  H14  C9   C10  107.21  3.000
 LOA  C11  C9   C10  113.93  3.000
 LOA  H14  C9   C8   105.63  3.000
 LOA  C11  C9   C8   111.54  3.000
 LOA  C10  C9   C8   112.13  3.000
 LOA  C19  C10  C9   111.32  3.000
 LOA  C9   C10  C5   109.31  3.000
 LOA  C19  C10  C5   109.64  3.000
 LOA  C9   C10  C1   111.96  3.000
 LOA  C5   C10  C1   107.89  3.000
 LOA  C19  C10  C1   106.62  3.000
 LOA  H16  C11  H15  105.57  3.000
 LOA  H16  C11  C12  109.49  3.000
 LOA  H15  C11  C12  107.82  3.000
 LOA  H16  C11  C9   110.42  3.000
 LOA  H15  C11  C9   109.78  3.000
 LOA  C12  C11  C9   113.43  3.000
 LOA  H18  C12  H17  106.26  3.000
 LOA  H18  C12  C13  112.20  3.000
 LOA  H17  C12  C13  108.45  3.000
 LOA  H18  C12  C11  108.60  3.000
 LOA  H17  C12  C11  109.11  3.000
 LOA  C13  C12  C11  112.02  3.000
 LOA  C18  C13  C17  110.22  3.000
 LOA  C17  C13  C14  100.09  3.000
 LOA  C18  C13  C14  112.22  3.000
 LOA  C17  C13  C12  116.65  3.000
 LOA  C14  C13  C12  106.53  3.000
 LOA  C18  C13  C12  110.67  3.000
 LOA  H19  C14  C15  106.49  3.000
 LOA  H19  C14  C13  105.67  3.000
 LOA  C15  C14  C13  104.25  3.000
 LOA  H19  C14  C8   106.49  3.000
 LOA  C15  C14  C8   118.47  3.000
 LOA  C13  C14  C8   114.57  3.000
 LOA  H21  C15  H20  106.46  3.000
 LOA  H21  C15  C16  112.27  3.000
 LOA  H20  C15  C16  111.29  3.000
 LOA  H21  C15  C14  112.28  3.000
 LOA  H20  C15  C14  110.99  3.000
 LOA  C16  C15  C14  103.67  3.000
 LOA  H23  C16  H22  106.07  3.000
 LOA  H23  C16  C17  111.13  3.000
 LOA  H22  C16  C17  110.46  3.000
 LOA  H23  C16  C15  111.27  3.000
 LOA  H22  C16  C15  110.86  3.000
 LOA  C17  C16  C15  107.11  3.000
 LOA  H24  C17  C20  106.86  3.000
 LOA  H24  C17  C16  108.08  3.000
 LOA  C20  C17  C16  112.47  3.000
 LOA  H24  C17  C13  106.20  3.000
 LOA  C16  C17  C13  103.20  3.000
 LOA  C20  C17  C13  119.45  3.000
 LOA  H27  C18  H26  107.04  3.000
 LOA  H27  C18  H25  106.71  3.000
 LOA  H26  C18  H25  106.95  3.000
 LOA  H27  C18  C13  111.07  3.000
 LOA  H26  C18  C13  112.38  3.000
 LOA  H25  C18  C13  112.35  3.000
 LOA  H30  C19  H29  107.37  3.000
 LOA  H30  C19  H28  106.92  3.000
 LOA  H29  C19  H28  107.52  3.000
 LOA  H30  C19  C10  111.21  3.000
 LOA  H29  C19  C10  113.38  3.000
 LOA  H28  C19  C10  110.15  3.000
 LOA  H31  C20  C22  107.20  3.000
 LOA  H31  C20  C21  108.07  3.000
 LOA  C22  C20  C21  110.69  3.000
 LOA  H31  C20  C17  108.17  3.000
 LOA  C22  C20  C17  109.76  3.000
 LOA  C21  C20  C17  112.75  3.000
 LOA  H34  C21  H33  106.65  3.000
 LOA  H34  C21  H32  107.52  3.000
 LOA  H33  C21  H32  107.72  3.000
 LOA  H34  C21  C20  111.47  3.000
 LOA  H33  C21  C20  112.33  3.000
 LOA  H32  C21  C20  110.91  3.000
 LOA  H36  C22  H35  105.87  3.000
 LOA  H36  C22  C23  110.07  3.000
 LOA  H35  C22  C23  108.10  3.000
 LOA  H36  C22  C20  108.75  3.000
 LOA  H35  C22  C20  109.06  3.000
 LOA  C23  C22  C20  114.63  3.000
 LOA  H38  C23  H37  104.89  3.000
 LOA  H38  C23  C24  108.08  3.000
 LOA  H37  C23  C24  107.14  3.000
 LOA  H38  C23  C22  109.37  3.000
 LOA  H37  C23  C22  110.88  3.000
 LOA  C24  C23  C22  115.88  3.000
 LOA  OT2  C24  OT1  126.05  3.000
 LOA  OT2  C24  C23  115.75  3.000
 LOA  OT1  C24  C23  118.19  3.000
 LOA  H41  C25  H40  107.04  3.000
 LOA  H41  C25  H39  108.99  3.000
 LOA  H40  C25  H39  108.95  3.000
 LOA  H41  C25  C26  109.32  3.000
 LOA  H40  C25  C26  109.27  3.000
 LOA  H39  C25  C26  113.09  3.000
 LOA  O25  C26  C25  123.69  3.000
 LOA  C25  C26  O3   112.27  3.000
 LOA  O25  C26  O3   124.05  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
 LOA  Var_01  C10  C1   C2   C3    58.74  30.0  1
 LOA  Var_02  C8   C7   C6   C5    54.60  30.0  1
 LOA  Var_03  C13  C12  C11  C9   -54.65  30.0  1
 LOA  Var_04  C17  C16  C15  C14    8.28  30.0  1
 LOA  Var_05  O25  C26  O3   C3     0.28  30.0  1
 LOA  Var_06  C24  C23  C22  C20  173.31  30.0  3
 LOA  Var_07  OT1  C24  C23  C22    4.29  30.0  3
 LOA  Var_08  H39  C25  C26  O3    -0.28  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
 LOA  chir_01  C3   C2   C4   O3   positiv
 LOA  chir_02  C5   C10  C6   C4   positiv
 LOA  chir_03  C8   C14  C7   C9   positiv
 LOA  chir_04  C9   C10  C11  C8   negativ
 LOA  chir_05  C10  C1   C5   C9   negativ
 LOA  chir_06  C13  C12  C14  C17  negativ
 LOA  chir_07  C14  C15  C13  C8   positiv
 LOA  chir_08  C17  C16  C20  C13  positiv
 LOA  chir_09  C20  C22  C17  C21  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
 LOA  plan-1  C23  0.020
 LOA  plan-1  C24  0.020
 LOA  plan-1  OT1  0.020
 LOA  plan-1  OT2  0.020
 LOA  plan-2  O3   0.020
 LOA  plan-2  C25  0.020
 LOA  plan-2  C26  0.020
 LOA  plan-2  O25  0.020

