# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Jul 30 00:42:59 2021
#   Inital geometry file: a 144 line input string
#   Ligand name: (3beta,5beta,14beta,17alpha)-3-hydroxycholan-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](O)CC[C@]4(C)[C@H]3CC[C@]12C
#
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
 4OA  4OA  '(3beta,5beta,14beta,17alpha)-3-hydroxycholan-24-oic acid'  ligand  67  27  .  2022-03-10  2022-11-17
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_4OA
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
 4OA  C1    C  CH2   0  -0.428  27.9707   -0.6066  -31.5712
 4OA  C10   C  CT    0  -0.063  27.1849   -0.6223  -30.2482
 4OA  C11   C  CH2   0  -0.440  28.1999   -2.8928  -29.5602
 4OA  C12   C  CH2   0  -0.407  27.9422   -4.3126  -29.0506
 4OA  C13   C  CT    0  -0.045  27.1058   -4.3163  -27.7717
 4OA  C14   C  CH1   0  -0.173  25.8143   -3.5353  -28.0741
 4OA  C15   C  CH2   0  -0.449  24.9115   -3.8327  -26.8810
 4OA  C16   C  CH2   0  -0.445  25.2722   -5.2832  -26.5002
 4OA  C17   C  CH1   0  -0.186  26.5044   -5.6795  -27.3533
 4OA  C18   C  CH3   0  -0.690  27.8870   -3.7044  -26.6056
 4OA  C19   C  CH3   0  -0.667  28.0076    0.1807  -29.2338
 4OA  O1B   O  OH1   0  -0.677  25.1917   -0.9428  -34.0943
 4OA  C2    C  CH2   0  -0.468  27.2224   -1.2009  -32.7577
 4OA  C20   C  CH1   0  -0.238  27.3996   -6.6988  -26.6381
 4OA  C21   C  CH3   0  -0.675  28.6482   -7.0865  -27.4291
 4OA  C22   C  CH2   0  -0.444  26.6133   -7.9563  -26.2367
 4OA  C23   C  CH2   0  -0.559  26.0360   -8.7336  -27.4287
 4OA  C24   C  C     0   0.534  25.3853  -10.0147  -26.9941
 4OA  C3    C  CH1   0   0.066  25.9166   -0.4533  -32.9804
 4OA  C4    C  CH2   0  -0.463  25.0783   -0.4575  -31.7092
 4OA  O4    O  OH1   0  -0.593  24.2635   -9.8010  -26.3116
 4OA  O4A   O  O     0  -0.449  25.8161  -11.1215  -27.2108
 4OA  C5    C  CH1   0  -0.208  25.8322    0.0896  -30.4901
 4OA  C6    C  CH2   0  -0.432  24.9421    0.0598  -29.2459
 4OA  C7    C  CH2   0  -0.425  24.7250   -1.3531  -28.7175
 4OA  C8    C  CH1   0  -0.220  26.0426   -2.0873  -28.4779
 4OA  C9    C  CH1   0  -0.188  26.9238   -2.0644  -29.7433
 4OA  H1    H  HCH2  0   0.231  28.9365   -1.1029  -31.4495
 4OA  H1A   H  HCH2  0   0.218  28.2088    0.4379  -31.8052
 4OA  H11   H  HCH2  0   0.228  28.7267   -2.9651  -30.5145
 4OA  H11A  H  HCH2  0   0.215  28.8881   -2.3815  -28.8818
 4OA  H12   H  HCH2  0   0.206  27.4072   -4.8814  -29.8210
 4OA  H12A  H  HCH2  0   0.223  28.9028   -4.8128  -28.9109
 4OA  H14   H  HCH1  0   0.202  25.3573   -4.0304  -28.9461
 4OA  H15   H  HCH2  0   0.215  25.1200   -3.1444  -26.0568
 4OA  H15A  H  HCH2  0   0.229  23.8537   -3.7170  -27.1217
 4OA  H16   H  HCH2  0   0.220  25.5060   -5.3594  -25.4344
 4OA  H16A  H  HCH2  0   0.229  24.4389   -5.9664  -26.6754
 4OA  H17   H  HCH1  0   0.212  26.1466   -6.1430  -28.2831
 4OA  H18   H  HCH3  0   0.230  28.7935   -4.2752  -26.3957
 4OA  H18A  H  HCH3  0   0.234  28.2016   -2.6799  -26.8023
 4OA  H18B  H  HCH3  0   0.231  27.2979   -3.6827  -25.6871
 4OA  H19   H  HCH3  0   0.226  29.0026   -0.2456  -29.0948
 4OA  H19A  H  HCH3  0   0.223  28.1448    1.2050  -29.5887
 4OA  H19B  H  HCH3  0   0.229  27.5403    0.2373  -28.2514
 4OA  HO1B  H  HOH1  0   0.436  24.9184   -1.8447  -33.8955
 4OA  H2    H  HCH2  0   0.232  27.8449   -1.1386  -33.6547
 4OA  H2A   H  HCH2  0   0.214  27.0181   -2.2658  -32.5955
 4OA  H20   H  HCH1  0   0.225  27.7291   -6.2484  -25.6941
 4OA  H21   H  HCH3  0   0.217  28.4122   -7.3664  -28.4574
 4OA  H21A  H  HCH3  0   0.233  29.3699   -6.2725  -27.4747
 4OA  H21B  H  HCH3  0   0.229  29.1521   -7.9366  -26.9641
 4OA  H22   H  HCH2  0   0.240  27.2855   -8.6141  -25.6772
 4OA  H22A  H  HCH2  0   0.247  25.8069   -7.6895  -25.5509
 4OA  H23   H  HCH2  0   0.266  25.2979   -8.1223  -27.9538
 4OA  H23A  H  HCH2  0   0.262  26.8239   -8.9814  -28.1391
 4OA  H3    H  HCH1  0   0.208  26.1604    0.5854  -33.2331
 4OA  H4    H  HCH2  0   0.230  24.1788    0.1465  -31.8646
 4OA  H4A   H  HCH2  0   0.213  24.7293   -1.4804  -31.5257
 4OA  HO4   H  HOH1  0   0.479  23.8796  -10.6462  -26.0343
 4OA  H5    H  HCH1  0   0.212  26.0607    1.1415  -30.7101
 4OA  H6    H  HCH2  0   0.222  25.3907    0.6719  -28.4581
 4OA  H6A   H  HCH2  0   0.222  23.9799    0.5280  -29.4757
 4OA  H7    H  HCH2  0   0.230  24.1520   -1.3111  -27.7869
 4OA  H7A   H  HCH2  0   0.205  24.1124   -1.9333  -29.4177
 4OA  H8    H  HCH1  0   0.205  26.5666   -1.5757  -27.6606
 4OA  H9    H  HCH1  0   0.205  26.3348   -2.5819  -30.5130

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
 4OA  C2   C1    single  1.523  0.020  1.523
 4OA  C1   C10   single  1.539  0.020  1.539
 4OA  C1   H1    single  0.970  0.020  1.090
 4OA  C1   H1A   single  0.970  0.020  1.090
 4OA  C5   C10   single  1.548  0.020  1.548
 4OA  C10  C9    single  1.550  0.020  1.550
 4OA  C10  C19   single  1.533  0.020  1.533
 4OA  C9   C11   single  1.532  0.020  1.532
 4OA  C11  C12   single  1.530  0.020  1.530
 4OA  C11  H11   single  0.970  0.020  1.090
 4OA  C11  H11A  single  0.970  0.020  1.090
 4OA  C12  C13   single  1.528  0.020  1.528
 4OA  C12  H12   single  0.970  0.020  1.090
 4OA  C12  H12A  single  0.970  0.020  1.090
 4OA  C14  C13   single  1.539  0.020  1.539
 4OA  C13  C17   single  1.548  0.020  1.548
 4OA  C13  C18   single  1.531  0.020  1.531
 4OA  C8   C14   single  1.520  0.020  1.520
 4OA  C14  C15   single  1.525  0.020  1.525
 4OA  C14  H14   single  0.970  0.020  1.090
 4OA  C15  C16   single  1.542  0.020  1.542
 4OA  C15  H15   single  0.970  0.020  1.090
 4OA  C15  H15A  single  0.970  0.020  1.090
 4OA  C17  C16   single  1.550  0.020  1.550
 4OA  C16  H16   single  0.970  0.020  1.090
 4OA  C16  H16A  single  0.970  0.020  1.090
 4OA  C17  C20   single  1.533  0.020  1.533
 4OA  C17  H17   single  0.970  0.020  1.090
 4OA  C18  H18   single  0.970  0.020  1.090
 4OA  C18  H18A  single  0.970  0.020  1.090
 4OA  C18  H18B  single  0.970  0.020  1.090
 4OA  C19  H19   single  0.970  0.020  1.090
 4OA  C19  H19A  single  0.970  0.020  1.090
 4OA  C19  H19B  single  0.970  0.020  1.090
 4OA  O1B  C3    single  1.416  0.020  1.416
 4OA  O1B  HO1B  single  0.850  0.020  0.980
 4OA  C3   C2    single  1.521  0.020  1.521
 4OA  C2   H2    single  0.970  0.020  1.090
 4OA  C2   H2A   single  0.970  0.020  1.090
 4OA  C21  C20   single  1.528  0.020  1.528
 4OA  C20  C22   single  1.537  0.020  1.537
 4OA  C20  H20   single  0.970  0.020  1.090
 4OA  C21  H21   single  0.970  0.020  1.090
 4OA  C21  H21A  single  0.970  0.020  1.090
 4OA  C21  H21B  single  0.970  0.020  1.090
 4OA  C23  C22   single  1.536  0.020  1.536
 4OA  C22  H22   single  0.970  0.020  1.090
 4OA  C22  H22A  single  0.970  0.020  1.090
 4OA  C23  C24   single  1.501  0.020  1.501
 4OA  C23  H23   single  0.970  0.020  1.090
 4OA  C23  H23A  single  0.970  0.020  1.090
 4OA  O4A  C24   double  1.207  0.020  1.207
 4OA  C24  O4    single  1.330  0.020  1.330
 4OA  C3   C4    single  1.523  0.020  1.523
 4OA  C3   H3    single  0.970  0.020  1.090
 4OA  C4   C5    single  1.534  0.020  1.534
 4OA  C4   H4    single  0.970  0.020  1.090
 4OA  C4   H4A   single  0.970  0.020  1.090
 4OA  O4   HO4   single  0.850  0.020  0.980
 4OA  C5   C6    single  1.530  0.020  1.530
 4OA  C5   H5    single  0.970  0.020  1.090
 4OA  C6   C7    single  1.524  0.020  1.524
 4OA  C6   H6    single  0.970  0.020  1.090
 4OA  C6   H6A   single  0.970  0.020  1.090
 4OA  C7   C8    single  1.527  0.020  1.527
 4OA  C7   H7    single  0.970  0.020  1.090
 4OA  C7   H7A   single  0.970  0.020  1.090
 4OA  C9   C8    single  1.542  0.020  1.542
 4OA  C8   H8    single  0.970  0.020  1.090
 4OA  C9   H9    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
 4OA  H1A   C1   H1    105.33  3.000
 4OA  H1A   C1   C2    108.18  3.000
 4OA  H1    C1   C2    110.10  3.000
 4OA  H1A   C1   C10   107.71  3.000
 4OA  H1    C1   C10   110.55  3.000
 4OA  C2    C1   C10   114.51  3.000
 4OA  C9    C10  C5    109.37  3.000
 4OA  C9    C10  C19   111.23  3.000
 4OA  C5    C10  C19   109.36  3.000
 4OA  C19   C10  C1    106.83  3.000
 4OA  C9    C10  C1    112.06  3.000
 4OA  C5    C10  C1    107.89  3.000
 4OA  H11A  C11  H11   105.63  3.000
 4OA  H11A  C11  C9    110.21  3.000
 4OA  H11   C11  C9    109.45  3.000
 4OA  H11A  C11  C12   109.47  3.000
 4OA  H11   C11  C12   108.10  3.000
 4OA  C9    C11  C12   113.65  3.000
 4OA  H12A  C12  H12   106.35  3.000
 4OA  H12A  C12  C13   111.92  3.000
 4OA  H12   C12  C13   108.64  3.000
 4OA  H12A  C12  C11   108.63  3.000
 4OA  H12   C12  C11   109.23  3.000
 4OA  C13   C12  C11   111.91  3.000
 4OA  C18   C13  C17   110.14  3.000
 4OA  C18   C13  C14   112.02  3.000
 4OA  C17   C13  C14   100.02  3.000
 4OA  C18   C13  C12   110.93  3.000
 4OA  C17   C13  C12   116.17  3.000
 4OA  C14   C13  C12   107.07  3.000
 4OA  H14   C14  C8    106.26  3.000
 4OA  H14   C14  C15   106.61  3.000
 4OA  C8    C14  C15   118.83  3.000
 4OA  H14   C14  C13   105.99  3.000
 4OA  C15   C14  C13   104.12  3.000
 4OA  C8    C14  C13   114.17  3.000
 4OA  H15A  C15  H15   106.52  3.000
 4OA  H15A  C15  C16   112.39  3.000
 4OA  H15   C15  C16   111.17  3.000
 4OA  H15A  C15  C14   112.37  3.000
 4OA  H15   C15  C14   110.72  3.000
 4OA  C16   C15  C14   103.77  3.000
 4OA  H16A  C16  H16   106.02  3.000
 4OA  H16A  C16  C17   111.00  3.000
 4OA  H16   C16  C17   110.39  3.000
 4OA  H16A  C16  C15   111.74  3.000
 4OA  H16   C16  C15   110.86  3.000
 4OA  C17   C16  C15   106.89  3.000
 4OA  H17   C17  C20   107.72  3.000
 4OA  H17   C17  C16   108.34  3.000
 4OA  C20   C17  C16   112.17  3.000
 4OA  H17   C17  C13   105.62  3.000
 4OA  C20   C17  C13   118.99  3.000
 4OA  C16   C17  C13   103.44  3.000
 4OA  H18B  C18  H18A  106.80  3.000
 4OA  H18B  C18  H18   107.27  3.000
 4OA  H18A  C18  H18   106.66  3.000
 4OA  H18B  C18  C13   111.93  3.000
 4OA  H18A  C18  C13   112.68  3.000
 4OA  H18   C18  C13   111.17  3.000
 4OA  H19B  C19  H19A  107.34  3.000
 4OA  H19B  C19  H19   107.25  3.000
 4OA  H19A  C19  H19   107.04  3.000
 4OA  H19B  C19  C10   113.18  3.000
 4OA  H19A  C19  C10   110.09  3.000
 4OA  H19   C19  C10   111.64  3.000
 4OA  HO1B  O1B  C3    107.85  3.000
 4OA  H2A   C2   H2    106.42  3.000
 4OA  H2A   C2   C3    109.82  3.000
 4OA  H2    C2   C3    109.91  3.000
 4OA  H2A   C2   C1    110.80  3.000
 4OA  H2    C2   C1    109.70  3.000
 4OA  C3    C2   C1    110.12  3.000
 4OA  H20   C20  C22   105.37  3.000
 4OA  H20   C20  C21   107.72  3.000
 4OA  C22   C20  C21   110.22  3.000
 4OA  H20   C20  C17   107.69  3.000
 4OA  C22   C20  C17   111.54  3.000
 4OA  C21   C20  C17   113.84  3.000
 4OA  H21B  C21  H21A  107.09  3.000
 4OA  H21B  C21  H21   107.53  3.000
 4OA  H21A  C21  H21   107.19  3.000
 4OA  H21B  C21  C20   110.74  3.000
 4OA  H21A  C21  C20   111.94  3.000
 4OA  H21   C21  C20   112.09  3.000
 4OA  H22A  C22  H22   106.23  3.000
 4OA  H22A  C22  C23   109.49  3.000
 4OA  H22   C22  C23   108.88  3.000
 4OA  H22A  C22  C20   110.00  3.000
 4OA  H22   C22  C20   108.13  3.000
 4OA  C23   C22  C20   113.82  3.000
 4OA  H23A  C23  H23   107.60  3.000
 4OA  H23A  C23  C24   107.95  3.000
 4OA  H23   C23  C24   108.89  3.000
 4OA  H23A  C23  C22   110.45  3.000
 4OA  H23   C23  C22   110.10  3.000
 4OA  C24   C23  C22   111.73  3.000
 4OA  O4A   C24  O4    122.69  3.000
 4OA  O4    C24  C23   112.15  3.000
 4OA  O4A   C24  C23   125.16  3.000
 4OA  H3    C3   C4    108.50  3.000
 4OA  H3    C3   C2    107.97  3.000
 4OA  C4    C3   C2    110.43  3.000
 4OA  H3    C3   O1B   105.07  3.000
 4OA  C4    C3   O1B   111.95  3.000
 4OA  C2    C3   O1B   112.63  3.000
 4OA  H4A   C4   H4    106.08  3.000
 4OA  H4A   C4   C5    110.87  3.000
 4OA  H4    C4   C5    108.65  3.000
 4OA  H4A   C4   C3    108.52  3.000
 4OA  H4    C4   C3    109.41  3.000
 4OA  C5    C4   C3    113.07  3.000
 4OA  HO4   O4   C24   109.93  3.000
 4OA  H5    C5   C6    107.61  3.000
 4OA  H5    C5   C4    106.53  3.000
 4OA  C6    C5   C4    110.69  3.000
 4OA  H5    C5   C10   106.85  3.000
 4OA  C6    C5   C10   111.87  3.000
 4OA  C4    C5   C10   112.93  3.000
 4OA  H6A   C6   H6    105.81  3.000
 4OA  H6A   C6   C7    110.13  3.000
 4OA  H6    C6   C7    109.11  3.000
 4OA  H6A   C6   C5    109.41  3.000
 4OA  H6    C6   C5    109.64  3.000
 4OA  C7    C6   C5    112.51  3.000
 4OA  H7A   C7   H7    105.72  3.000
 4OA  H7A   C7   C8    109.14  3.000
 4OA  H7    C7   C8    109.70  3.000
 4OA  H7A   C7   C6    110.40  3.000
 4OA  H7    C7   C6    109.51  3.000
 4OA  C8    C7   C6    112.16  3.000
 4OA  H8    C8   C9    109.34  3.000
 4OA  H8    C8   C7    107.74  3.000
 4OA  C9    C8   C7    110.92  3.000
 4OA  H8    C8   C14   108.54  3.000
 4OA  C9    C8   C14   108.53  3.000
 4OA  C7    C8   C14   111.71  3.000
 4OA  H9    C9   C8    105.16  3.000
 4OA  H9    C9   C11   105.99  3.000
 4OA  C8    C9   C11   111.70  3.000
 4OA  H9    C9   C10   107.48  3.000
 4OA  C8    C9   C10   112.17  3.000
 4OA  C11   C9   C10   113.68  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
 4OA  CONST_01  HO4  O4   C24  C23   180.00   0.0  0
 4OA  Var_01    C3   C2   C1   C10    58.20  30.0  1
 4OA  Var_02    C9   C11  C12  C13   -53.62  30.0  1
 4OA  Var_03    C17  C16  C15  C14     8.10  30.0  1
 4OA  Var_04    C8   C7   C6   C5     53.46  30.0  1
 4OA  Var_05    C24  C23  C22  C20   174.87  30.0  1
 4OA  Var_06    O4A  C24  C23  C22  -109.70  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
 4OA  chir_01  C10  C5   C9   C1   negativ
 4OA  chir_02  C13  C17  C14  C12  positiv
 4OA  chir_03  C14  C13  C8   C15  positiv
 4OA  chir_04  C17  C13  C16  C20  positiv
 4OA  chir_05  C20  C17  C21  C22  positiv
 4OA  chir_06  C3   O1B  C2   C4   positiv
 4OA  chir_07  C5   C6   C4   C10  positiv
 4OA  chir_08  C8   C14  C7   C9   positiv
 4OA  chir_09  C9   C10  C11  C8   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
 4OA  plan-1  C23  0.020
 4OA  plan-1  C24  0.020
 4OA  plan-1  O4   0.020
 4OA  plan-1  O4A  0.020
 4OA  plan-1  HO4  0.020

