# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr 26 23:36:15 2020
#   Inital geometry file: a 134 line input string
#   Ligand name: (8beta,13E)-11-hydroxy-9,15-dioxoprosta-5,13-dien-1-oic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCCCC(=O)\C=C\[C@@H]1C(O)CC(=O)[C@H]1CC=CCCCC(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
 5OP  5OP  '(8beta,13E)-11-hydroxy-9,15-dioxoprosta-5,13-dien-1-oic acid'  ligand  55  25  .  2021-08-05  2021-08-05  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_5OP
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
 5OP  C1    C  CH3   0  -0.662  -1.1906   8.1986  -0.4011
 5OP  C2    C  CH2   0  -0.419  -0.2843   6.9821  -0.5289
 5OP  C3    C  CH2   0  -0.408  -1.0382   5.6671  -0.3747
 5OP  C4    C  CH2   0  -0.414  -0.1408   4.4453  -0.5257
 5OP  C5    C  CH2   0  -0.575  -0.9053   3.1455  -0.3485
 5OP  C6    C  C     0   0.372  -0.0918   1.8919  -0.5388
 5OP  C7    C  C1    0  -0.348  -0.8351   0.6257  -0.3763
 5OP  C8    C  C1    0  -0.103  -0.3359  -0.5416  -0.7836
 5OP  C9    C  CH1   0  -0.353  -1.0550  -1.8416  -0.7081
 5OP  C10   C  CH1   0   0.035  -0.3364  -2.8600   0.1995
 5OP  O1    O  OH1   0  -0.664   1.0260  -2.8651  -0.1607
 5OP  C11   C  CH2   0  -0.604  -1.0015  -4.1745  -0.1727
 5OP  C12   C  C     0   0.437  -1.2083  -4.0576  -1.6611
 5OP  O2    O  O     0  -0.395  -1.3706  -4.9723  -2.4301
 5OP  C13   C  CH1   0  -0.383  -1.2100  -2.5835  -2.0535
 5OP  C14   C  CH2   0  -0.454  -2.4696  -2.2436  -2.8490
 5OP  C15   C  C1    0  -0.243  -2.5283  -0.8718  -3.4526
 5OP  C16   C  C1    0  -0.166  -1.5062  -0.0586  -3.6927
 5OP  C17   C  CH2   0  -0.486  -1.6269   1.3192  -4.2604
 5OP  C18   C  CH2   0  -0.428  -0.8190   1.4991  -5.5453
 5OP  C19   C  CH2   0  -0.585  -0.7669   2.9394  -6.0314
 5OP  C20   C  C     0   0.548  -2.0828   3.4718  -6.5299
 5OP  O3    O  OH1   0  -0.596  -2.0791   4.7988  -6.6180
 5OP  O4    O  O     0  -0.420   1.0873   1.9219  -0.8342
 5OP  O5    O  O     0  -0.446  -3.0308   2.7973  -6.8484
 5OP  H11   H  HCH3  0   0.226  -0.6304   9.1296  -0.4967
 5OP  H12   H  HCH3  0   0.216  -1.6933   8.2149   0.5679
 5OP  H13A  H  HCH3  0   0.216  -1.9637   8.1972  -1.1716
 5OP  H21   H  HCH2  0   0.212   0.5088   7.0348   0.2233
 5OP  H22   H  HCH2  0   0.211   0.2189   6.9988  -1.5009
 5OP  H31   H  HCH2  0   0.210  -1.8434   5.6230  -1.1166
 5OP  H32   H  HCH2  0   0.210  -1.5289   5.6449   0.6050
 5OP  H41   H  HCH2  0   0.218   0.3321   4.4634  -1.5118
 5OP  H42   H  HCH2  0   0.221   0.6719   4.4968   0.2043
 5OP  H51   H  HCH2  0   0.268  -1.3724   3.0975   0.6427
 5OP  H52   H  HCH2  0   0.263  -1.7482   3.0952  -1.0503
 5OP  H7    H  H     0   0.254  -1.8427   0.6872   0.0223
 5OP  H8    H  H     0   0.268   0.6605  -0.5600  -1.2151
 5OP  H9    H  HCH1  0   0.278  -2.0518  -1.6794  -0.2833
 5OP  H10   H  HCH1  0   0.242  -0.4743  -2.6058   1.2556
 5OP  HO1   H  HOH1  0   0.457   1.4727  -3.5555   0.3394
 5OP  H111  H  HCH2  0   0.285  -1.9924  -4.2395   0.2923
 5OP  H112  H  HCH2  0   0.287  -0.4484  -5.0692   0.1179
 5OP  H13   H  HCH1  0   0.293  -0.3230  -2.4291  -2.6809
 5OP  H141  H  HCH2  0   0.241  -3.3381  -2.3695  -2.1943
 5OP  H142  H  HCH2  0   0.255  -2.5958  -2.9864  -3.6438
 5OP  H15   H  H     0   0.233  -3.5282  -0.5327  -3.7136
 5OP  H16   H  H     0   0.226  -0.4949  -0.3730  -3.4488
 5OP  H171  H  HCH2  0   0.220  -1.2614   2.0379  -3.5159
 5OP  H172  H  HCH2  0   0.238  -2.6785   1.5595  -4.4311
 5OP  H181  H  HCH2  0   0.240   0.2082   1.1690  -5.3705
 5OP  H182  H  HCH2  0   0.235  -1.2190   0.8517  -6.3288
 5OP  H191  H  HCH2  0   0.295  -0.0595   3.0267  -6.8631
 5OP  H192  H  HCH2  0   0.266  -0.3823   3.5991  -5.2494
 5OP  HO3   H  HOH1  0   0.477  -2.9238   5.1090  -6.9773

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
 5OP  C1   C2    single  1.522  0.020  1.522
 5OP  C1   H11   single  0.970  0.020  1.090
 5OP  C1   H12   single  0.970  0.020  1.090
 5OP  C1   H13A  single  0.970  0.020  1.090
 5OP  C2   C3    single  1.524  0.020  1.524
 5OP  C2   H21   single  0.970  0.020  1.090
 5OP  C2   H22   single  0.970  0.020  1.090
 5OP  C3   C4    single  1.523  0.020  1.523
 5OP  C3   H31   single  0.970  0.020  1.090
 5OP  C3   H32   single  0.970  0.020  1.090
 5OP  C4   C5    single  1.518  0.020  1.518
 5OP  C4   H41   single  0.970  0.020  1.090
 5OP  C4   H42   single  0.970  0.020  1.090
 5OP  C5   C6    single  1.506  0.020  1.506
 5OP  C5   H51   single  0.970  0.020  1.090
 5OP  C5   H52   single  0.970  0.020  1.090
 5OP  C6   C7    single  1.477  0.020  1.477
 5OP  C6   O4    double  1.216  0.020  1.216
 5OP  C7   C8    double  1.333  0.020  1.333
 5OP  C7   H7    single  0.930  0.020  1.080
 5OP  C8   C9    single  1.488  0.020  1.488
 5OP  C8   H8    single  0.930  0.020  1.080
 5OP  C9   C10   single  1.542  0.020  1.542
 5OP  C9   C13   single  1.544  0.020  1.544
 5OP  C9   H9    single  0.970  0.020  1.090
 5OP  C10  O1    single  1.409  0.020  1.409
 5OP  C10  C11   single  1.519  0.020  1.519
 5OP  C10  H10   single  0.970  0.020  1.090
 5OP  O1   HO1   single  0.850  0.020  0.980
 5OP  C11  C12   single  1.507  0.020  1.507
 5OP  C11  H111  single  0.970  0.020  1.090
 5OP  C11  H112  single  0.970  0.020  1.090
 5OP  C12  O2    double  1.206  0.020  1.206
 5OP  C12  C13   single  1.525  0.020  1.525
 5OP  C13  C14   single  1.528  0.020  1.528
 5OP  C13  H13   single  0.970  0.020  1.090
 5OP  C14  C15   single  1.500  0.020  1.500
 5OP  C14  H141  single  0.970  0.020  1.090
 5OP  C14  H142  single  0.970  0.020  1.090
 5OP  C15  C16   double  1.328  0.020  1.328
 5OP  C15  H15   single  0.930  0.020  1.080
 5OP  C16  C17   single  1.495  0.020  1.495
 5OP  C16  H16   single  0.930  0.020  1.080
 5OP  C17  C18   single  1.528  0.020  1.528
 5OP  C17  H171  single  0.970  0.020  1.090
 5OP  C17  H172  single  0.970  0.020  1.090
 5OP  C18  C19   single  1.521  0.020  1.521
 5OP  C18  H181  single  0.970  0.020  1.090
 5OP  C18  H182  single  0.970  0.020  1.090
 5OP  C19  C20   single  1.505  0.020  1.505
 5OP  C19  H191  single  0.970  0.020  1.090
 5OP  C19  H192  single  0.970  0.020  1.090
 5OP  C20  O3    single  1.330  0.020  1.330
 5OP  C20  O5    double  1.206  0.020  1.206
 5OP  O3   HO3   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
 5OP  H13A  C1   H12   107.48  3.000
 5OP  H13A  C1   H11   107.63  3.000
 5OP  H12   C1   H11   107.55  3.000
 5OP  H13A  C1   C2    111.19  3.000
 5OP  H12   C1   C2    111.13  3.000
 5OP  H11   C1   C2    111.65  3.000
 5OP  H22   C2   H21   106.05  3.000
 5OP  H22   C2   C3    109.30  3.000
 5OP  H21   C2   C3    109.30  3.000
 5OP  H22   C2   C1    109.63  3.000
 5OP  H21   C2   C1    109.59  3.000
 5OP  C3    C2   C1    112.74  3.000
 5OP  H32   C3   H31   105.99  3.000
 5OP  H32   C3   C4    109.64  3.000
 5OP  H31   C3   C4    109.48  3.000
 5OP  H32   C3   C2    109.24  3.000
 5OP  H31   C3   C2    109.25  3.000
 5OP  C4    C3   C2    112.99  3.000
 5OP  H42   C4   H41   106.25  3.000
 5OP  H42   C4   C5    109.67  3.000
 5OP  H41   C4   C5    109.70  3.000
 5OP  H42   C4   C3    109.50  3.000
 5OP  H41   C4   C3    109.32  3.000
 5OP  C5    C4   C3    112.23  3.000
 5OP  H52   C5   H51   104.40  3.000
 5OP  H52   C5   C6    107.20  3.000
 5OP  H51   C5   C6    107.92  3.000
 5OP  H52   C5   C4    110.56  3.000
 5OP  H51   C5   C4    110.94  3.000
 5OP  C6    C5   C4    115.20  3.000
 5OP  O4    C6   C7    122.40  3.000
 5OP  O4    C6   C5    122.27  3.000
 5OP  C7    C6   C5    115.32  3.000
 5OP  H7    C7   C8    120.62  3.000
 5OP  H7    C7   C6    117.32  3.000
 5OP  C8    C7   C6    121.90  3.000
 5OP  H8    C8   C9    116.67  3.000
 5OP  H8    C8   C7    118.68  3.000
 5OP  C9    C8   C7    124.65  3.000
 5OP  H9    C9   C13   108.52  3.000
 5OP  H9    C9   C10   107.07  3.000
 5OP  C13   C9   C10   104.02  3.000
 5OP  H9    C9   C8    109.28  3.000
 5OP  C13   C9   C8    115.10  3.000
 5OP  C10   C9   C8    112.44  3.000
 5OP  H10   C10  C11   112.45  3.000
 5OP  H10   C10  O1    111.66  3.000
 5OP  C11   C10  O1    110.95  3.000
 5OP  H10   C10  C9    110.83  3.000
 5OP  C11   C10  C9    102.90  3.000
 5OP  O1    C10  C9    107.61  3.000
 5OP  HO1   O1   C10   108.57  3.000
 5OP  H112  C11  H111  107.25  3.000
 5OP  H112  C11  C12   113.33  3.000
 5OP  H111  C11  C12   107.42  3.000
 5OP  H112  C11  C10   114.97  3.000
 5OP  H111  C11  C10   110.06  3.000
 5OP  C12   C11  C10   103.58  3.000
 5OP  C13   C12  O2    124.67  3.000
 5OP  C13   C12  C11   109.21  3.000
 5OP  O2    C12  C11   126.11  3.000
 5OP  H13   C13  C14   109.72  3.000
 5OP  H13   C13  C12   106.39  3.000
 5OP  C14   C13  C12   110.47  3.000
 5OP  H13   C13  C9    110.45  3.000
 5OP  C14   C13  C9    115.43  3.000
 5OP  C12   C13  C9    103.89  3.000
 5OP  H142  C14  H141  105.34  3.000
 5OP  H142  C14  C15   108.89  3.000
 5OP  H141  C14  C15   108.35  3.000
 5OP  H142  C14  C13   108.78  3.000
 5OP  H141  C14  C13   108.48  3.000
 5OP  C15   C14  C13   116.44  3.000
 5OP  H15   C15  C16   118.25  3.000
 5OP  H15   C15  C14   114.69  3.000
 5OP  C16   C15  C14   127.06  3.000
 5OP  H16   C16  C17   115.27  3.000
 5OP  H16   C16  C15   119.90  3.000
 5OP  C17   C16  C15   124.81  3.000
 5OP  H172  C17  H171  106.42  3.000
 5OP  H172  C17  C18   110.59  3.000
 5OP  H171  C17  C18   108.50  3.000
 5OP  H172  C17  C16   109.86  3.000
 5OP  H171  C17  C16   108.60  3.000
 5OP  C18   C17  C16   112.64  3.000
 5OP  H182  C18  H181  106.26  3.000
 5OP  H182  C18  C19   110.16  3.000
 5OP  H181  C18  C19   107.75  3.000
 5OP  H182  C18  C17   109.86  3.000
 5OP  H181  C18  C17   109.07  3.000
 5OP  C19   C18  C17   113.46  3.000
 5OP  H192  C19  H191  105.54  3.000
 5OP  H192  C19  C20   109.34  3.000
 5OP  H191  C19  C20   106.56  3.000
 5OP  H192  C19  C18   110.79  3.000
 5OP  H191  C19  C18   109.89  3.000
 5OP  C20   C19  C18   114.27  3.000
 5OP  O5    C20  O3    122.86  3.000
 5OP  O5    C20  C19   125.24  3.000
 5OP  O3    C20  C19   111.88  3.000
 5OP  HO3   O3   C20   109.97  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
 5OP  CONST_01  HO3  O3   C20  C19   180.00   0.0  0
 5OP  Var_01    C13  C12  C11  C10   -22.21  30.0  1
 5OP  Var_02    C9   C8   C7   C6   -177.03   0.0  2
 5OP  Var_03    C16  C15  C14  C13    19.77  30.0  3
 5OP  Var_04    C17  C16  C15  C14  -178.06   0.0  2
 5OP  Var_05    C4   C3   C2   C1    179.00  30.0  3
 5OP  Var_06    C5   C4   C3   C2    179.15  30.0  3
 5OP  Var_07    C6   C5   C4   C3    177.67  30.0  3
 5OP  Var_08    C7   C6   C5   C4   -179.59  30.0  3
 5OP  Var_09    C8   C7   C6   C5    165.60  30.0  2
 5OP  Var_10    C18  C17  C16  C15  -122.86  30.0  3
 5OP  Var_11    C19  C18  C17  C16  -171.81  30.0  3
 5OP  Var_12    C20  C19  C18  C17   -68.55  30.0  3
 5OP  Var_13    O3   C20  C19  C18   163.94  30.0  3
 5OP  Var_14    H11  C1   C2   C3    178.99  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
 5OP  chir_01  C9   C8  C10  C13  positiv
 5OP  chir_02  C10  O1  C9   C11  negativ
 5OP  chir_03  C13  C9  C12  C14  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
 5OP  plan-1  C5   0.020
 5OP  plan-1  C6   0.020
 5OP  plan-1  C7   0.020
 5OP  plan-1  O4   0.020
 5OP  plan-2  C11  0.020
 5OP  plan-2  C12  0.020
 5OP  plan-2  O2   0.020
 5OP  plan-2  C13  0.020
 5OP  plan-3  C19  0.020
 5OP  plan-3  C20  0.020
 5OP  plan-3  O3   0.020
 5OP  plan-3  O5   0.020
 5OP  plan-3  HO3  0.020
 5OP  plan-4  C6   0.020
 5OP  plan-4  C7   0.020
 5OP  plan-4  C8   0.020
 5OP  plan-4  C9   0.020
 5OP  plan-4  H7   0.020
 5OP  plan-4  H8   0.020
 5OP  plan-5  C14  0.020
 5OP  plan-5  C15  0.020
 5OP  plan-5  C16  0.020
 5OP  plan-5  C17  0.020
 5OP  plan-5  H15  0.020
 5OP  plan-5  H16  0.020

