# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version 1.18.1-3865-
#   - file written: Mon Jun  8 05:49:04 2020
#   Inital geometry file: a 153 line input string
#   Ligand name: (8alpha,10alpha,13alpha,17beta)-17-[(4-hydroxyphenyl)carbonyl]androsta-3,5-diene-3-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@]12CC[C@H]3[C@@H](CC=C4C=C(CC[C@]34C)C(O)=O)[C@@H]1CC[C@@H]2C(=O)c5ccc(O)cc5
#
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
 MUF  MUF  '(8alpha,10alpha,13alpha,17beta)-17-[(4-hydroxyphenyl)carbonyl]androsta-3,5-diene-3-carboxylic acid'  ligand  62  31  .  2021-08-14  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_MUF
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
 MUF  C1    C  CH2    0  -0.444  -3.0434  -1.7697  -0.0788
 MUF  C2    C  CH2    0  -0.489  -4.1770  -1.9023   0.9365
 MUF  C3    C  C      0  -0.083  -5.3560  -1.0619   0.5456
 MUF  C4    C  C1     0  -0.287  -5.0984   0.1814   0.1278
 MUF  C5    C  C      0   0.163  -3.7158   0.6602   0.0600
 MUF  C6    C  C1     0  -0.297  -3.4059   1.8908   0.4768
 MUF  C7    C  CH2    0  -0.444  -2.0208   2.4337   0.5791
 MUF  C8    C  CH1    0  -0.237  -0.9764   1.5760  -0.1283
 MUF  C9    C  CH1    0  -0.199  -1.2731   0.0745   0.0427
 MUF  C10   C  CT     0  -0.093  -2.6780  -0.3117  -0.4830
 MUF  C11   C  CH2    0  -0.435  -0.1479  -0.7774  -0.5600
 MUF  C12   C  CH2    0  -0.393   1.2385  -0.4132  -0.0256
 MUF  C13   C  CT     0  -0.051   1.5358   1.0642  -0.2520
 MUF  C14   C  CH1    0  -0.178   0.4139   1.8788   0.4074
 MUF  C15   C  CH2    0  -0.434   0.9284   3.3142   0.3732
 MUF  C16   C  CH2    0  -0.418   2.4518   3.1670   0.5844
 MUF  C17   C  CH1    0  -0.372   2.7517   1.6543   0.5206
 MUF  C18   C  CH3    0  -0.671   1.6711   1.3591  -1.7494
 MUF  C19   C  CH3    0  -0.656  -2.7545  -0.2074  -2.0158
 MUF  C20   C  C      0   0.394   4.0863   1.2998  -0.0881
 MUF  O52   O  O      0  -0.402   4.6496   2.0534  -0.8582
 MUF  C28   C  C      0   0.372  -6.7735  -1.5715   0.7112
 MUF  O76   O  O      0  -0.601  -7.6955  -0.8503   0.2783
 MUF  O82   O  OC    -1  -0.602  -6.9033  -2.6757   1.2792
 MUF  C52   C  CR6    0  -0.025   4.6910  -0.0236   0.2117
 MUF  C53   C  CR16   0  -0.240   5.6693  -0.5227  -0.6558
 MUF  C54   C  CR16   0  -0.304   6.2827  -1.7355  -0.4298
 MUF  C55   C  CR6    0   0.373   5.9477  -2.4838   0.7001
 MUF  C56   C  CR16   0  -0.347   4.9847  -2.0000   1.5811
 MUF  C57   C  CR16   0  -0.255   4.3644  -0.7886   1.3308
 MUF  O57   O  OH1    0  -0.600   6.5853  -3.6473   0.8862
 MUF  H1    H  HCH2   0   0.227  -2.1653  -2.2864   0.3127
 MUF  H1A   H  HCH2   0   0.224  -3.3372  -2.3243  -0.9739
 MUF  H2    H  HCH2   0   0.239  -4.4602  -2.9496   1.0342
 MUF  H2A   H  HCH2   0   0.216  -3.8236  -1.5899   1.9271
 MUF  H4    H  H      0   0.224  -5.9077   0.8693  -0.0931
 MUF  H6    H  H      0   0.215  -4.2054   2.5357   0.8324
 MUF  H7    H  HCH2   0   0.235  -1.9887   3.4570   0.1922
 MUF  H7A   H  HCH2   0   0.219  -1.7663   2.5271   1.6440
 MUF  H8    H  HCH1   0   0.212  -1.0076   1.8270  -1.1956
 MUF  H9    H  HCH1   0   0.204  -1.2831  -0.1234   1.1264
 MUF  H11   H  HCH2   0   0.232  -0.3260  -1.8354  -0.3580
 MUF  H11A  H  HCH2   0   0.217  -0.1495  -0.6844  -1.6486
 MUF  H12   H  HCH2   0   0.201   1.2738  -0.6310   1.0483
 MUF  H12A  H  HCH2   0   0.229   1.9923  -1.0511  -0.4955
 MUF  H14   H  HCH1   0   0.202   0.4046   1.5731   1.4661
 MUF  H15   H  HCH2   0   0.216   0.7063   3.7821  -0.5891
 MUF  H15A  H  HCH2   0   0.230   0.4665   3.9380   1.1389
 MUF  H16   H  HCH2   0   0.236   3.0113   3.7100  -0.1753
 MUF  H16A  H  HCH2   0   0.234   2.7634   3.5700   1.5484
 MUF  H17   H  HCH1   0   0.242   2.7009   1.2515   1.5355
 MUF  H18   H  HCH3   0   0.232   0.7397   1.1804  -2.2848
 MUF  H18A  H  HCH3   0   0.238   1.9664   2.3890  -1.9487
 MUF  H18B  H  HCH3   0   0.228   2.4233   0.7126  -2.2055
 MUF  H19   H  HCH3   0   0.219  -2.1075  -0.9369  -2.5058
 MUF  H19A  H  HCH3   0   0.233  -3.7732  -0.4054  -2.3537
 MUF  H19B  H  HCH3   0   0.220  -2.4801   0.7845  -2.3767
 MUF  H53   H  HCR6   0   0.248   5.9481   0.0470  -1.5320
 MUF  H54   H  HCR6   0   0.253   7.0270  -2.1117  -1.1192
 MUF  H56   H  HCR6   0   0.244   4.7156  -2.5612   2.4682
 MUF  H57   H  HCR6   0   0.237   3.6312  -0.4440   2.0463
 MUF  HO57  H  HOH1   0   0.451   6.2796  -4.0745   1.6916

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
 MUF  C10  C1    single    1.556  0.020  1.556
 MUF  C1   C2    single    1.528  0.020  1.528
 MUF  C1   H1    single    0.970  0.020  1.090
 MUF  C1   H1A   single    0.970  0.020  1.090
 MUF  C2   C3    single    1.500  0.020  1.500
 MUF  C2   H2    single    0.970  0.020  1.090
 MUF  C2   H2A   single    0.970  0.020  1.090
 MUF  C3   C4    double    1.337  0.020  1.337
 MUF  C3   C28   single    1.515  0.020  1.515
 MUF  C5   C4    single    1.465  0.020  1.465
 MUF  C4   H4    single    0.930  0.020  1.080
 MUF  C10  C5    single    1.522  0.020  1.522
 MUF  C5   C6    double    1.336  0.020  1.336
 MUF  C7   C6    single    1.491  0.020  1.491
 MUF  C6   H6    single    0.930  0.020  1.080
 MUF  C8   C7    single    1.525  0.020  1.525
 MUF  C7   H7    single    0.970  0.020  1.090
 MUF  C7   H7A   single    0.970  0.020  1.090
 MUF  C14  C8    single    1.520  0.020  1.520
 MUF  C9   C8    single    1.540  0.020  1.540
 MUF  C8   H8    single    0.970  0.020  1.090
 MUF  C11  C9    single    1.535  0.020  1.535
 MUF  C9   C10   single    1.549  0.020  1.549
 MUF  C9   H9    single    0.970  0.020  1.090
 MUF  C19  C10   single    1.538  0.020  1.538
 MUF  C12  C11   single    1.530  0.020  1.530
 MUF  C11  H11   single    0.970  0.020  1.090
 MUF  C11  H11A  single    0.970  0.020  1.090
 MUF  C12  C13   single    1.524  0.020  1.524
 MUF  C12  H12   single    0.970  0.020  1.090
 MUF  C12  H12A  single    0.970  0.020  1.090
 MUF  C18  C13   single    1.532  0.020  1.532
 MUF  C17  C13   single    1.557  0.020  1.557
 MUF  C13  C14   single    1.535  0.020  1.535
 MUF  C14  C15   single    1.525  0.020  1.525
 MUF  C14  H14   single    0.970  0.020  1.090
 MUF  C16  C15   single    1.545  0.020  1.545
 MUF  C15  H15   single    0.970  0.020  1.090
 MUF  C15  H15A  single    0.970  0.020  1.090
 MUF  C17  C16   single    1.543  0.020  1.543
 MUF  C16  H16   single    0.970  0.020  1.090
 MUF  C16  H16A  single    0.970  0.020  1.090
 MUF  C20  C17   single    1.509  0.020  1.509
 MUF  C17  H17   single    0.970  0.020  1.090
 MUF  C18  H18   single    0.970  0.020  1.090
 MUF  C18  H18A  single    0.970  0.020  1.090
 MUF  C18  H18B  single    0.970  0.020  1.090
 MUF  C19  H19   single    0.970  0.020  1.090
 MUF  C19  H19A  single    0.970  0.020  1.090
 MUF  C19  H19B  single    0.970  0.020  1.090
 MUF  O52  C20   double    1.216  0.020  1.216
 MUF  C52  C20   single    1.486  0.020  1.486
 MUF  O76  C28   deloc     1.248  0.020  1.248
 MUF  C28  O82   deloc     1.248  0.020  1.248
 MUF  C57  C52   aromatic  1.394  0.020  1.394
 MUF  C52  C53   aromatic  1.400  0.020  1.400
 MUF  C54  C53   aromatic  1.378  0.020  1.378
 MUF  C53  H53   single    0.930  0.020  1.080
 MUF  C55  C54   aromatic  1.396  0.020  1.396
 MUF  C54  H54   single    0.930  0.020  1.080
 MUF  C56  C55   aromatic  1.392  0.020  1.392
 MUF  O57  C55   single    1.340  0.020  1.340
 MUF  C56  C57   aromatic  1.384  0.020  1.384
 MUF  C56  H56   single    0.930  0.020  1.080
 MUF  C57  H57   single    0.930  0.020  1.080
 MUF  O57  HO57  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
 MUF  H1A   C1   H1    105.65  3.000
 MUF  H1A   C1   C10   109.01  3.000
 MUF  H1    C1   C10   110.35  3.000
 MUF  H1A   C1   C2    107.50  3.000
 MUF  H1    C1   C2    108.51  3.000
 MUF  C10   C1   C2    115.35  3.000
 MUF  H2A   C2   H2    106.05  3.000
 MUF  H2A   C2   C3    109.21  3.000
 MUF  H2    C2   C3    110.96  3.000
 MUF  H2A   C2   C1    109.65  3.000
 MUF  H2    C2   C1    109.64  3.000
 MUF  C3    C2   C1    111.20  3.000
 MUF  C28   C3   C4    121.82  3.000
 MUF  C28   C3   C2    121.23  3.000
 MUF  C4    C3   C2    116.82  3.000
 MUF  H4    C4   C5    119.17  3.000
 MUF  H4    C4   C3    120.64  3.000
 MUF  C5    C4   C3    120.03  3.000
 MUF  C10   C5   C6    122.78  3.000
 MUF  C6    C5   C4    120.38  3.000
 MUF  C10   C5   C4    116.83  3.000
 MUF  H6    C6   C7    116.41  3.000
 MUF  H6    C6   C5    118.55  3.000
 MUF  C7    C6   C5    124.92  3.000
 MUF  H7A   C7   H7    104.85  3.000
 MUF  H7A   C7   C8    109.79  3.000
 MUF  H7    C7   C8    109.98  3.000
 MUF  H7A   C7   C6    108.21  3.000
 MUF  H7    C7   C6    110.09  3.000
 MUF  C8    C7   C6    113.54  3.000
 MUF  H8    C8   C14   108.86  3.000
 MUF  H8    C8   C9    109.00  3.000
 MUF  C14   C8   C9    109.34  3.000
 MUF  H8    C8   C7    107.64  3.000
 MUF  C9    C8   C7    111.40  3.000
 MUF  C14   C8   C7    110.53  3.000
 MUF  H9    C9   C11   107.05  3.000
 MUF  H9    C9   C10   106.31  3.000
 MUF  C11   C9   C10   113.16  3.000
 MUF  H9    C9   C8    106.62  3.000
 MUF  C10   C9   C8    112.34  3.000
 MUF  C11   C9   C8    110.88  3.000
 MUF  C19   C10  C9    111.49  3.000
 MUF  C19   C10  C5    106.16  3.000
 MUF  C9    C10  C5    109.77  3.000
 MUF  C19   C10  C1    108.09  3.000
 MUF  C9    C10  C1    111.00  3.000
 MUF  C5    C10  C1    110.21  3.000
 MUF  H11A  C11  H11   105.46  3.000
 MUF  H11A  C11  C12   109.21  3.000
 MUF  H11   C11  C12   108.29  3.000
 MUF  H11A  C11  C9    110.06  3.000
 MUF  H11   C11  C9    110.23  3.000
 MUF  C12   C11  C9    113.28  3.000
 MUF  H12A  C12  H12   106.43  3.000
 MUF  H12A  C12  C13   111.54  3.000
 MUF  H12   C12  C13   109.38  3.000
 MUF  H12A  C12  C11   109.62  3.000
 MUF  H12   C12  C11   108.91  3.000
 MUF  C13   C12  C11   110.83  3.000
 MUF  C18   C13  C17   110.07  3.000
 MUF  C17   C13  C14    99.00  3.000
 MUF  C18   C13  C14   112.47  3.000
 MUF  C14   C13  C12   107.94  3.000
 MUF  C17   C13  C12   116.50  3.000
 MUF  C18   C13  C12   110.43  3.000
 MUF  H14   C14  C15   106.59  3.000
 MUF  H14   C14  C13   105.76  3.000
 MUF  C15   C14  C13   104.08  3.000
 MUF  H14   C14  C8    106.00  3.000
 MUF  C15   C14  C8    119.21  3.000
 MUF  C13   C14  C8    114.28  3.000
 MUF  H15A  C15  H15   106.71  3.000
 MUF  H15A  C15  C16   112.10  3.000
 MUF  H15   C15  C16   111.20  3.000
 MUF  H15A  C15  C14   112.32  3.000
 MUF  H15   C15  C14   110.74  3.000
 MUF  C16   C15  C14   103.88  3.000
 MUF  H16A  C16  H16   106.60  3.000
 MUF  H16A  C16  C17   110.08  3.000
 MUF  H16   C16  C17   111.11  3.000
 MUF  H16A  C16  C15   111.56  3.000
 MUF  H16   C16  C15   111.34  3.000
 MUF  C17   C16  C15   106.22  3.000
 MUF  H17   C17  C20   109.21  3.000
 MUF  H17   C17  C16   108.29  3.000
 MUF  C20   C17  C16   114.76  3.000
 MUF  H17   C17  C13   106.55  3.000
 MUF  C20   C17  C13   113.67  3.000
 MUF  C16   C17  C13   103.90  3.000
 MUF  H18B  C18  H18A  107.25  3.000
 MUF  H18B  C18  H18   106.67  3.000
 MUF  H18A  C18  H18   107.27  3.000
 MUF  H18B  C18  C13   110.80  3.000
 MUF  H18A  C18  C13   112.61  3.000
 MUF  H18   C18  C13   111.92  3.000
 MUF  H19B  C19  H19A  107.30  3.000
 MUF  H19B  C19  H19   108.08  3.000
 MUF  H19A  C19  H19   107.05  3.000
 MUF  H19B  C19  C10   112.27  3.000
 MUF  H19A  C19  C10   110.03  3.000
 MUF  H19   C19  C10   111.87  3.000
 MUF  C52   C20  O52   119.43  3.000
 MUF  C52   C20  C17   119.20  3.000
 MUF  O52   C20  C17   121.30  3.000
 MUF  O82   C28  O76   126.31  3.000
 MUF  O82   C28  C3    116.38  3.000
 MUF  O76   C28  C3    117.31  3.000
 MUF  C57   C52  C53   117.74  3.000
 MUF  C53   C52  C20   118.50  3.000
 MUF  C57   C52  C20   123.74  3.000
 MUF  H53   C53  C54   118.80  3.000
 MUF  H53   C53  C52   119.63  3.000
 MUF  C54   C53  C52   121.56  3.000
 MUF  H54   C54  C55   119.63  3.000
 MUF  H54   C54  C53   120.51  3.000
 MUF  C55   C54  C53   119.85  3.000
 MUF  O57   C55  C56   122.90  3.000
 MUF  O57   C55  C54   117.63  3.000
 MUF  C56   C55  C54   119.47  3.000
 MUF  H56   C56  C57   119.34  3.000
 MUF  H56   C56  C55   120.66  3.000
 MUF  C57   C56  C55   120.00  3.000
 MUF  H57   C57  C56   117.61  3.000
 MUF  H57   C57  C52   121.01  3.000
 MUF  C56   C57  C52   121.36  3.000
 MUF  HO57  O57  C55   110.54  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
 MUF  CONST_01  C55  C56  C57  C52     0.00   0.0  0
 MUF  CONST_02  C55  C54  C53  C52     0.00   0.0  0
 MUF  CONST_03  C56  C57  C52  C53     0.00   0.0  0
 MUF  CONST_04  C56  C55  C54  C53     0.00   0.0  0
 MUF  CONST_05  C57  C52  C53  C54     0.00   0.0  0
 MUF  CONST_06  C57  C56  C55  C54     0.00   0.0  0
 MUF  CONST_07  C56  C57  C52  C20   180.00   0.0  0
 MUF  CONST_08  C54  C53  C52  C20   180.00   0.0  0
 MUF  CONST_09  O57  C55  C54  C53   180.00   0.0  0
 MUF  CONST_10  O57  C55  C56  C57   180.00   0.0  0
 MUF  CONST_11  H56  C56  C57  C52   180.00   0.0  0
 MUF  CONST_12  H54  C54  C53  C52   180.00   0.0  0
 MUF  CONST_13  H57  C57  C52  C53   180.00   0.0  0
 MUF  CONST_14  H53  C53  C54  C55   180.00   0.0  0
 MUF  Var_01    C4   C3   C2   C1    -44.38  30.0  1
 MUF  Var_02    C5   C4   C3   C2      0.41  30.0  1
 MUF  Var_03    C10  C1   C2   C3     48.09  30.0  1
 MUF  Var_04    C10  C5   C4   C3     41.69  30.0  1
 MUF  Var_05    C7   C6   C5   C4    173.70  30.0  1
 MUF  Var_06    C8   C7   C6   C5     13.00  30.0  1
 MUF  Var_07    C13  C12  C11  C9    -56.22  30.0  1
 MUF  Var_08    C17  C16  C15  C14     8.09  30.0  1
 MUF  Var_09    C57  C52  C20  C17   -22.03  30.0  2
 MUF  Var_10    O76  C28  C3   C2   -175.21  30.0  2

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
 MUF  chir_01  C8   C7   C14  C9   negativ
 MUF  chir_02  C9   C10  C11  C8   negativ
 MUF  chir_03  C10  C5   C9   C1   negativ
 MUF  chir_04  C13  C12  C17  C14  positiv
 MUF  chir_05  C14  C15  C13  C8   positiv
 MUF  chir_06  C17  C20  C16  C13  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
 MUF  plan-1  C20  0.020
 MUF  plan-1  C52  0.020
 MUF  plan-1  C53  0.020
 MUF  plan-1  C54  0.020
 MUF  plan-1  C55  0.020
 MUF  plan-1  C56  0.020
 MUF  plan-1  C57  0.020
 MUF  plan-1  O57  0.020
 MUF  plan-1  H53  0.020
 MUF  plan-1  H54  0.020
 MUF  plan-1  H56  0.020
 MUF  plan-1  H57  0.020
 MUF  plan-2  C17  0.020
 MUF  plan-2  C20  0.020
 MUF  plan-2  O52  0.020
 MUF  plan-2  C52  0.020
 MUF  plan-3  C3   0.020
 MUF  plan-3  C28  0.020
 MUF  plan-3  O76  0.020
 MUF  plan-3  O82  0.020

