# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Mar 24 23:32:56 2022
#   Inital geometry file: a 135 line input string
#   Ligand name: (11alpha,12alpha,13E,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-oic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=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
 XPG  XPG  '(11alpha,12alpha,13E,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-oic acid'  ligand  58  25  .  2022-03-29  2022-03-29
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_XPG
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
 XPG  C20  C  CH3    0  -0.661   9.1740  -3.4607   0.7103
 XPG  C19  C  CH2    0  -0.419   7.9205  -3.2678  -0.1323
 XPG  C18  C  CH2    0  -0.407   6.9432  -2.2742   0.4838
 XPG  C17  C  CH2    0  -0.412   5.6788  -2.0807  -0.3446
 XPG  C16  C  CH2    0  -0.461   4.7488  -1.0304   0.2489
 XPG  C15  C  CH1    0   0.006   3.4249  -0.8723  -0.5022
 XPG  O15  O  OH1    0  -0.662   3.6130  -0.6055  -1.8727
 XPG  C14  C  C1     0  -0.264   2.5610   0.1503   0.1822
 XPG  C13  C  C1     0  -0.171   1.9890   1.1973  -0.4015
 XPG  C12  C  CH1    0  -0.352   1.1580   2.2138   0.3044
 XPG  C11  C  CH1    0   0.083   1.6194   3.6527   0.0566
 XPG  O11  O  OH1    0  -0.662   2.8144   3.9024   0.7461
 XPG  C10  C  CH2    0  -0.605   0.4267   4.4932   0.5032
 XPG  C9   C  C      0   0.419  -0.7786   3.6313   0.2058
 XPG  O9   O  O      0  -0.396  -1.9268   3.9996   0.2644
 XPG  C8   C  CH1    0  -0.362  -0.3113   2.2298  -0.1476
 XPG  C7   C  CH2    0  -0.412  -1.1644   1.1005   0.4226
 XPG  C6   C  CH2    0  -0.418  -2.4586   0.8392  -0.3381
 XPG  C5   C  CH2    0  -0.413  -3.3167  -0.2411   0.3088
 XPG  C4   C  CH2    0  -0.409  -4.6057  -0.5143  -0.4564
 XPG  C3   C  CH2    0  -0.402  -5.5189  -1.5236   0.2300
 XPG  C2   C  CH2    0  -0.581  -6.7965  -1.7818  -0.5518
 XPG  C1   C  C      0   0.410  -7.7986  -2.7621   0.0822
 XPG  O1A  O  OC    -1  -0.635  -8.8334  -2.9889  -0.5815
 XPG  O1B  O  O      0  -0.610  -7.5162  -3.2511   1.1937
 XPG  H1   H  HCH3   0   0.215   9.7021  -2.5153   0.8500
 XPG  H2   H  HCH3   0   0.216   8.9281  -3.8484   1.7007
 XPG  H3   H  HCH3   0   0.225   9.8688  -4.1610   0.2450
 XPG  H4   H  HCH2   0   0.210   8.2002  -2.9234  -1.1328
 XPG  H5   H  HCH2   0   0.210   7.4191  -4.2303  -0.2729
 XPG  H6   H  HCH2   0   0.207   6.6732  -2.6088   1.4915
 XPG  H7   H  HCH2   0   0.207   7.4461  -1.3088   0.6112
 XPG  H8   H  HCH2   0   0.213   5.9565  -1.7963  -1.3634
 XPG  H9   H  HCH2   0   0.210   5.1476  -3.0355  -0.4272
 XPG  H10  H  HCH2   0   0.225   4.5210  -1.2911   1.2873
 XPG  H11  H  HCH2   0   0.223   5.2617  -0.0617   0.2879
 XPG  H12  H  HCH1   0   0.234   2.9033  -1.8372  -0.4649
 XPG  H13  H  HOH1   0   0.443   4.1402   0.1975  -1.9516
 XPG  H14  H  H      0   0.240   2.4241  -0.0028   1.2504
 XPG  H15  H  H      0   0.235   2.1053   1.3527  -1.4725
 XPG  H16  H  HCH1   0   0.252   1.1835   2.0305   1.3870
 XPG  H17  H  HCH1   0   0.208   1.7571   3.7862  -1.0270
 XPG  H18  H  HOH1   0   0.453   3.1122   4.7901   0.5244
 XPG  H19  H  HCH2   0   0.280   0.4659   4.6416   1.5891
 XPG  H20  H  HCH2   0   0.281   0.3541   5.4782   0.0391
 XPG  H21  H  HCH1   0   0.279  -0.3320   2.1751  -1.2477
 XPG  H22  H  HCH2   0   0.233  -0.5590   0.1882   0.4202
 XPG  H23  H  HCH2   0   0.222  -1.3832   1.3124   1.4744
 XPG  H24  H  HCH2   0   0.222  -3.0400   1.7609  -0.4098
 XPG  H25  H  HCH2   0   0.209  -2.2166   0.5478  -1.3662
 XPG  H26  H  HCH2   0   0.206  -2.7394  -1.1683   0.3962
 XPG  H27  H  HCH2   0   0.205  -3.5615   0.0613   1.3333
 XPG  H28  H  HCH2   0   0.201  -5.1481   0.4283  -0.5938
 XPG  H29  H  HCH2   0   0.202  -4.3606  -0.8682  -1.4643
 XPG  H30  H  HCH2   0   0.199  -4.9762  -2.4623   0.3769
 XPG  H31  H  HCH2   0   0.200  -5.7656  -1.1596   1.2316
 XPG  H32  H  HCH2   0   0.216  -7.3154  -0.8314  -0.7266
 XPG  H33  H  HCH2   0   0.215  -6.5471  -2.1513  -1.5534

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
 XPG  O15  C15  single  1.409  0.020  1.409
 XPG  C18  C17  single  1.524  0.020  1.524
 XPG  C18  C19  single  1.524  0.020  1.524
 XPG  C20  C19  single  1.523  0.020  1.523
 XPG  C16  C17  single  1.523  0.020  1.523
 XPG  C16  C15  single  1.530  0.020  1.530
 XPG  C15  C14  single  1.503  0.020  1.503
 XPG  C14  C13  double  1.328  0.020  1.328
 XPG  C13  C12  single  1.491  0.020  1.491
 XPG  O11  C11  single  1.402  0.020  1.402
 XPG  C11  C12  single  1.531  0.020  1.531
 XPG  C11  C10  single  1.526  0.020  1.526
 XPG  C12  C8   single  1.537  0.020  1.537
 XPG  C8   C9   single  1.519  0.020  1.519
 XPG  C8   C7   single  1.526  0.020  1.526
 XPG  C10  C9   single  1.511  0.020  1.511
 XPG  C9   O9   double  1.207  0.020  1.207
 XPG  C7   C6   single  1.524  0.020  1.524
 XPG  C6   C5   single  1.524  0.020  1.524
 XPG  C5   C4   single  1.524  0.020  1.524
 XPG  C4   C3   single  1.524  0.020  1.524
 XPG  C3   C2   single  1.520  0.020  1.520
 XPG  C2   C1   single  1.539  0.020  1.539
 XPG  O1B  C1   deloc   1.247  0.020  1.247
 XPG  C1   O1A  deloc   1.250  0.020  1.250
 XPG  C20  H1   single  0.970  0.020  1.090
 XPG  C20  H2   single  0.970  0.020  1.090
 XPG  C20  H3   single  0.970  0.020  1.090
 XPG  C19  H4   single  0.970  0.020  1.090
 XPG  C19  H5   single  0.970  0.020  1.090
 XPG  C18  H6   single  0.970  0.020  1.090
 XPG  C18  H7   single  0.970  0.020  1.090
 XPG  C17  H8   single  0.970  0.020  1.090
 XPG  C17  H9   single  0.970  0.020  1.090
 XPG  C16  H10  single  0.970  0.020  1.090
 XPG  C16  H11  single  0.970  0.020  1.090
 XPG  C15  H12  single  0.970  0.020  1.090
 XPG  O15  H13  single  0.850  0.020  0.980
 XPG  C14  H14  single  0.930  0.020  1.080
 XPG  C13  H15  single  0.930  0.020  1.080
 XPG  C12  H16  single  0.970  0.020  1.090
 XPG  C11  H17  single  0.970  0.020  1.090
 XPG  O11  H18  single  0.850  0.020  0.980
 XPG  C10  H19  single  0.970  0.020  1.090
 XPG  C10  H20  single  0.970  0.020  1.090
 XPG  C8   H21  single  0.970  0.020  1.090
 XPG  C7   H22  single  0.970  0.020  1.090
 XPG  C7   H23  single  0.970  0.020  1.090
 XPG  C6   H24  single  0.970  0.020  1.090
 XPG  C6   H25  single  0.970  0.020  1.090
 XPG  C5   H26  single  0.970  0.020  1.090
 XPG  C5   H27  single  0.970  0.020  1.090
 XPG  C4   H28  single  0.970  0.020  1.090
 XPG  C4   H29  single  0.970  0.020  1.090
 XPG  C3   H30  single  0.970  0.020  1.090
 XPG  C3   H31  single  0.970  0.020  1.090
 XPG  C2   H32  single  0.970  0.020  1.090
 XPG  C2   H33  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
 XPG  H3   C20  H2   107.61  3.000
 XPG  H3   C20  H1   107.60  3.000
 XPG  H2   C20  H1   107.48  3.000
 XPG  H3   C20  C19  111.70  3.000
 XPG  H2   C20  C19  111.20  3.000
 XPG  H1   C20  C19  111.05  3.000
 XPG  H5   C19  H4   106.04  3.000
 XPG  H5   C19  C18  109.36  3.000
 XPG  H4   C19  C18  109.17  3.000
 XPG  H5   C19  C20  109.69  3.000
 XPG  H4   C19  C20  109.59  3.000
 XPG  C18  C19  C20  112.76  3.000
 XPG  H7   C18  H6   105.98  3.000
 XPG  H7   C18  C17  109.39  3.000
 XPG  H6   C18  C17  109.53  3.000
 XPG  H7   C18  C19  109.09  3.000
 XPG  H6   C18  C19  109.32  3.000
 XPG  C17  C18  C19  113.27  3.000
 XPG  H9   C17  H8   106.23  3.000
 XPG  H9   C17  C16  109.52  3.000
 XPG  H8   C17  C16  109.80  3.000
 XPG  H9   C17  C18  109.43  3.000
 XPG  H8   C17  C18  109.19  3.000
 XPG  C16  C17  C18  112.47  3.000
 XPG  H11  C16  H10  105.90  3.000
 XPG  H11  C16  C15  109.32  3.000
 XPG  H10  C16  C15  108.08  3.000
 XPG  H11  C16  C17  109.71  3.000
 XPG  H10  C16  C17  109.42  3.000
 XPG  C15  C16  C17  114.09  3.000
 XPG  H12  C15  C14  108.02  3.000
 XPG  H12  C15  O15  105.25  3.000
 XPG  C14  C15  O15  113.00  3.000
 XPG  H12  C15  C16  107.68  3.000
 XPG  C14  C15  C16  110.11  3.000
 XPG  O15  C15  C16  112.43  3.000
 XPG  H13  O15  C15  108.08  3.000
 XPG  H14  C14  C13  119.23  3.000
 XPG  H14  C14  C15  115.07  3.000
 XPG  C13  C14  C15  125.70  3.000
 XPG  H15  C13  C12  115.36  3.000
 XPG  H15  C13  C14  119.93  3.000
 XPG  C12  C13  C14  124.71  3.000
 XPG  H16  C12  C8   108.29  3.000
 XPG  H16  C12  C11  108.02  3.000
 XPG  C8   C12  C11  103.34  3.000
 XPG  H16  C12  C13  109.88  3.000
 XPG  C8   C12  C13  113.62  3.000
 XPG  C11  C12  C13  113.34  3.000
 XPG  H17  C11  C10  108.61  3.000
 XPG  H17  C11  O11  110.86  3.000
 XPG  C10  C11  O11  115.10  3.000
 XPG  H17  C11  C12  108.12  3.000
 XPG  C10  C11  C12  103.57  3.000
 XPG  O11  C11  C12  110.16  3.000
 XPG  H18  O11  C11  108.35  3.000
 XPG  H20  C10  H19  107.54  3.000
 XPG  H20  C10  C9   112.21  3.000
 XPG  H19  C10  C9   107.49  3.000
 XPG  H20  C10  C11  115.13  3.000
 XPG  H19  C10  C11  109.66  3.000
 XPG  C9   C10  C11  104.57  3.000
 XPG  C8   C9   O9   125.83  3.000
 XPG  O9   C9   C10  125.09  3.000
 XPG  C8   C9   C10  109.07  3.000
 XPG  H21  C8   C7   109.02  3.000
 XPG  H21  C8   C9   105.80  3.000
 XPG  C7   C8   C9   115.09  3.000
 XPG  H21  C8   C12  108.12  3.000
 XPG  C7   C8   C12  114.63  3.000
 XPG  C9   C8   C12  103.60  3.000
 XPG  H23  C7   H22  105.89  3.000
 XPG  H23  C7   C6   110.05  3.000
 XPG  H22  C7   C6   109.00  3.000
 XPG  H23  C7   C8   109.12  3.000
 XPG  H22  C7   C8   107.87  3.000
 XPG  C6   C7   C8   114.54  3.000
 XPG  H25  C6   H24  106.28  3.000
 XPG  H25  C6   C5   109.52  3.000
 XPG  H24  C6   C5   109.05  3.000
 XPG  H25  C6   C7   109.05  3.000
 XPG  H24  C6   C7   109.89  3.000
 XPG  C5   C6   C7   112.83  3.000
 XPG  H27  C5   H26  106.05  3.000
 XPG  H27  C5   C4   109.27  3.000
 XPG  H26  C5   C4   109.51  3.000
 XPG  H27  C5   C6   109.09  3.000
 XPG  H26  C5   C6   109.70  3.000
 XPG  C4   C5   C6   112.98  3.000
 XPG  H29  C4   H28  105.85  3.000
 XPG  H29  C4   C3   109.53  3.000
 XPG  H28  C4   C3   109.23  3.000
 XPG  H29  C4   C5   109.30  3.000
 XPG  H28  C4   C5   109.11  3.000
 XPG  C3   C4   C5   113.54  3.000
 XPG  H31  C3   H30  105.93  3.000
 XPG  H31  C3   C2   109.75  3.000
 XPG  H30  C3   C2   109.89  3.000
 XPG  H31  C3   C4   109.09  3.000
 XPG  H30  C3   C4   109.35  3.000
 XPG  C2   C3   C4   112.61  3.000
 XPG  H33  C2   H32  104.72  3.000
 XPG  H33  C2   C1   108.05  3.000
 XPG  H32  C2   C1   108.04  3.000
 XPG  H33  C2   C3   109.63  3.000
 XPG  H32  C2   C3   109.41  3.000
 XPG  C1   C2   C3   116.35  3.000
 XPG  O1B  C1   O1A  126.13  3.000
 XPG  O1A  C1   C2   115.85  3.000
 XPG  O1B  C1   C2   118.02  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
 XPG  Var_01  C8   C9   C10  C11    10.67  30.0  1
 XPG  Var_02  C12  C13  C14  C15  -178.71   0.0  2
 XPG  Var_03  C5   C6   C7   C8   -176.76  30.0  3
 XPG  Var_04  C17  C18  C19  C20  -179.53  30.0  2
 XPG  Var_05  C16  C17  C18  C19  -176.97  30.0  3
 XPG  Var_06  C15  C16  C17  C18  -176.15  30.0  1
 XPG  Var_07  C4   C5   C6   C7   -179.46  30.0  3
 XPG  Var_08  C3   C4   C5   C6   -176.03  30.0  3
 XPG  Var_09  C2   C3   C4   C5   -179.91  30.0  3
 XPG  Var_10  C1   C2   C3   C4   -178.51  30.0  3
 XPG  Var_11  O1B  C1   C2   C3      1.56  30.0  3
 XPG  Var_12  H1   C20  C19  C18   -58.85  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
 XPG  chir_01  C15  O15  C16  C14  negativ
 XPG  chir_02  C12  C8   C11  C13  positiv
 XPG  chir_03  C11  O11  C12  C10  negativ
 XPG  chir_04  C8   C12  C9   C7   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
 XPG  plan-1  C10  0.020
 XPG  plan-1  C9   0.020
 XPG  plan-1  O9   0.020
 XPG  plan-1  C8   0.020
 XPG  plan-2  C2   0.020
 XPG  plan-2  C1   0.020
 XPG  plan-2  O1A  0.020
 XPG  plan-2  O1B  0.020
 XPG  plan-3  C15  0.020
 XPG  plan-3  C14  0.020
 XPG  plan-3  C13  0.020
 XPG  plan-3  C12  0.020
 XPG  plan-3  H14  0.020
 XPG  plan-3  H15  0.020

