# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Apr  7 15:38:45 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  54  25  .  2021-08-04  2021-08-04  
;
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  -0.663  -1.2219   8.2993   0.5137
 5OP  C2    C  CH2    0  -0.419  -0.5183   7.1558  -0.2035
 5OP  C3    C  CH2    0  -0.409  -1.0131   5.7859   0.2432
 5OP  C4    C  CH2    0  -0.416  -0.3092   4.6341  -0.4637
 5OP  C5    C  CH2    0  -0.570  -0.8570   3.2849  -0.0320
 5OP  C6    C  C      0   0.382  -0.2078   2.0860  -0.6733
 5OP  C7    C  C1     0  -0.364  -0.8718   0.7930  -0.4089
 5OP  C8    C  C1     0  -0.086  -0.4483  -0.3503  -0.9499
 5OP  C9    C  CH1    0  -0.354  -1.1094  -1.6668  -0.7436
 5OP  C10   C  CH1    0   0.039  -0.2974  -2.6130   0.1610
 5OP  O1    O  OH1    0  -0.664   1.0267  -2.6298  -0.3195
 5OP  C11   C  CH2    0  -0.602  -0.9886  -3.9516  -0.0525
 5OP  C12   C  C      0   0.439  -1.3982  -3.9287  -1.5057
 5OP  O2    O  O      0  -0.398  -1.7325  -4.8849  -2.1605
 5OP  C13   C  CH1    0  -0.387  -1.3427  -2.4964  -2.0204
 5OP  C14   C  CH2    0  -0.454  -2.5768  -2.1265  -2.8350
 5OP  C15   C  C1     0  -0.243  -2.5011  -0.8377  -3.6014
 5OP  C16   C  C1     0  -0.178  -1.4045  -0.1917  -3.9842
 5OP  C17   C  CH2    0  -0.481  -1.3890   1.1007  -4.7355
 5OP  C18   C  CH2    0  -0.405  -0.7111   0.9902  -6.1015
 5OP  C19   C  CH2    0  -0.578  -0.5085   2.3394  -6.7746
 5OP  C20   C  C      0   0.406  -1.7921   3.0774  -7.1959
 5OP  O3    O  OC    -1  -0.630  -1.6989   4.3159  -7.3318
 5OP  O4    O  O      0  -0.423   0.7880   2.1795  -1.3646
 5OP  O5    O  O      0  -0.611  -2.8117   2.3898  -7.4058
 5OP  H11   H  HCH3   0   0.227  -0.8576   9.2700   0.1761
 5OP  H12   H  HCH3   0   0.216  -1.0642   8.2442   1.5925
 5OP  H13A  H  HCH3   0   0.216  -2.2991   8.2710   0.3386
 5OP  H21   H  HCH2   0   0.211   0.5607   7.2245  -0.0335
 5OP  H22   H  HCH2   0   0.212  -0.6610   7.2555  -1.2839
 5OP  H31   H  HCH2   0   0.209  -2.0925   5.7171   0.0677
 5OP  H32   H  HCH2   0   0.210  -0.8774   5.6868   1.3259
 5OP  H41   H  HCH2   0   0.220  -0.4248   4.7464  -1.5459
 5OP  H42   H  HCH2   0   0.221   0.7641   4.6862  -0.2629
 5OP  H51   H  HCH2   0   0.268  -0.7640   3.1582   1.0546
 5OP  H52   H  HCH2   0   0.260  -1.9349   3.2277  -0.2217
 5OP  H7    H  H      0   0.252  -1.7553   0.8085   0.2214
 5OP  H8    H  H      0   0.266   0.4349  -0.3326  -1.5810
 5OP  H9    H  HCH1   0   0.277  -2.0757  -1.5085  -0.2514
 5OP  H10   H  HCH1   0   0.240  -0.3422  -2.2857   1.2053
 5OP  HO1   H  HOH1   0   0.457   1.5255  -3.2841   0.1797
 5OP  H111  H  HCH2   0   0.287  -1.9052  -3.9963   0.5465
 5OP  H112  H  HCH2   0   0.287  -0.3891  -4.8258   0.2078
 5OP  H13   H  HCH1   0   0.295  -0.4479  -2.4509  -2.6547
 5OP  H141  H  HCH2   0   0.239  -3.4376  -2.0790  -2.1606
 5OP  H142  H  HCH2   0   0.253  -2.8007  -2.9406  -3.5328
 5OP  H15   H  H      0   0.230  -3.4655  -0.4113  -3.8678
 5OP  H16   H  H      0   0.223  -0.4250  -0.5979  -3.7432
 5OP  H171  H  HCH2   0   0.216  -0.8473   1.8433  -4.1368
 5OP  H172  H  HCH2   0   0.227  -2.4072   1.4759  -4.8609
 5OP  H181  H  HCH2   0   0.206   0.2611   0.5010  -5.9780
 5OP  H182  H  HCH2   0   0.209  -1.3042   0.3375  -6.7458
 5OP  H191  H  HCH2   0   0.231   0.0959   2.2012  -7.6796
 5OP  H192  H  HCH2   0   0.206   0.0859   2.9905  -6.1257

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  1.523  0.020  1.523
 5OP  C2   H21   single  0.970  0.020  1.090
 5OP  C2   H22   single  0.970  0.020  1.090
 5OP  C3   C4    single  1.524  0.020  1.524
 5OP  C3   H31   single  0.970  0.020  1.090
 5OP  C3   H32   single  0.970  0.020  1.090
 5OP  C4   C5    single  1.519  0.020  1.519
 5OP  C4   H41   single  0.970  0.020  1.090
 5OP  C4   H42   single  0.970  0.020  1.090
 5OP  C5   C6    single  1.507  0.020  1.507
 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  1.334  0.020  1.334
 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  1.540  0.020  1.540
 5OP  C9   C13   single  1.540  0.020  1.540
 5OP  C9   H9    single  0.970  0.020  1.090
 5OP  C10  O1    single  1.409  0.020  1.409
 5OP  C10  C11   single  1.522  0.020  1.522
 5OP  C10  H10   single  0.970  0.020  1.090
 5OP  O1   HO1   single  0.850  0.020  0.980
 5OP  C11  C12   single  1.510  0.020  1.510
 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  1.523  0.020  1.523
 5OP  C13  C14   single  1.524  0.020  1.524
 5OP  C13  H13   single  0.970  0.020  1.090
 5OP  C14  C15   single  1.501  0.020  1.501
 5OP  C14  H141  single  0.970  0.020  1.090
 5OP  C14  H142  single  0.970  0.020  1.090
 5OP  C15  C16   double  1.329  0.020  1.329
 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  1.529  0.020  1.529
 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  1.539  0.020  1.539
 5OP  C19  H191  single  0.970  0.020  1.090
 5OP  C19  H192  single  0.970  0.020  1.090
 5OP  C20  O3    deloc   1.249  0.020  1.249
 5OP  C20  O5    deloc   1.248  0.020  1.248

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   107.44  3.000
 5OP  H13A  C1   H11   107.65  3.000
 5OP  H12   C1   H11   107.62  3.000
 5OP  H13A  C1   C2    111.16  3.000
 5OP  H12   C1   C2    111.15  3.000
 5OP  H11   C1   C2    111.62  3.000
 5OP  H22   C2   H21   106.03  3.000
 5OP  H22   C2   C3    109.21  3.000
 5OP  H21   C2   C3    109.34  3.000
 5OP  H22   C2   C1    109.66  3.000
 5OP  H21   C2   C1    109.59  3.000
 5OP  C3    C2   C1    112.79  3.000
 5OP  H32   C3   H31   105.93  3.000
 5OP  H32   C3   C4    109.44  3.000
 5OP  H31   C3   C4    109.47  3.000
 5OP  H32   C3   C2    109.32  3.000
 5OP  H31   C3   C2    109.24  3.000
 5OP  C4    C3   C2    113.19  3.000
 5OP  H42   C4   H41   106.28  3.000
 5OP  H42   C4   C5    110.13  3.000
 5OP  H41   C4   C5    109.53  3.000
 5OP  H42   C4   C3    109.41  3.000
 5OP  H41   C4   C3    109.42  3.000
 5OP  C5    C4   C3    111.90  3.000
 5OP  H52   C5   H51   104.40  3.000
 5OP  H52   C5   C6    107.97  3.000
 5OP  H51   C5   C6    107.04  3.000
 5OP  H52   C5   C4    110.60  3.000
 5OP  H51   C5   C4    110.69  3.000
 5OP  C6    C5   C4    115.50  3.000
 5OP  O4    C6   C7    122.49  3.000
 5OP  O4    C6   C5    122.26  3.000
 5OP  C7    C6   C5    115.25  3.000
 5OP  H7    C7   C8    120.41  3.000
 5OP  H7    C7   C6    117.21  3.000
 5OP  C8    C7   C6    122.34  3.000
 5OP  H8    C8   C9    117.17  3.000
 5OP  H8    C8   C7    118.69  3.000
 5OP  C9    C8   C7    124.14  3.000
 5OP  H9    C9   C13   108.45  3.000
 5OP  H9    C9   C10   106.84  3.000
 5OP  C13   C9   C10   103.64  3.000
 5OP  H9    C9   C8    109.05  3.000
 5OP  C13   C9   C8    115.40  3.000
 5OP  C10   C9   C8    113.00  3.000
 5OP  H10   C10  C11   112.21  3.000
 5OP  H10   C10  O1    111.55  3.000
 5OP  C11   C10  O1    111.63  3.000
 5OP  H10   C10  C9    110.78  3.000
 5OP  C11   C10  C9    102.62  3.000
 5OP  O1    C10  C9    107.61  3.000
 5OP  HO1   O1   C10   108.57  3.000
 5OP  H112  C11  H111  107.23  3.000
 5OP  H112  C11  C12   112.99  3.000
 5OP  H111  C11  C12   107.45  3.000
 5OP  H112  C11  C10   114.94  3.000
 5OP  H111  C11  C10   109.83  3.000
 5OP  C12   C11  C10   104.18  3.000
 5OP  C13   C12  O2    124.91  3.000
 5OP  C13   C12  C11   109.24  3.000
 5OP  O2    C12  C11   125.85  3.000
 5OP  H13   C13  C14   109.94  3.000
 5OP  H13   C13  C12   105.30  3.000
 5OP  C14   C13  C12   112.29  3.000
 5OP  H13   C13  C9    109.47  3.000
 5OP  C14   C13  C9    115.78  3.000
 5OP  C12   C13  C9    103.41  3.000
 5OP  H142  C14  H141  105.31  3.000
 5OP  H142  C14  C15   108.85  3.000
 5OP  H141  C14  C15   108.48  3.000
 5OP  H142  C14  C13   109.00  3.000
 5OP  H141  C14  C13   108.54  3.000
 5OP  C15   C14  C13   116.12  3.000
 5OP  H15   C15  C16   118.07  3.000
 5OP  H15   C15  C14   114.64  3.000
 5OP  C16   C15  C14   127.29  3.000
 5OP  H16   C16  C17   115.15  3.000
 5OP  H16   C16  C15   119.86  3.000
 5OP  C17   C16  C15   124.99  3.000
 5OP  H172  C17  H171  106.88  3.000
 5OP  H172  C17  C18   109.60  3.000
 5OP  H171  C17  C18   108.52  3.000
 5OP  H172  C17  C16   110.18  3.000
 5OP  H171  C17  C16   108.43  3.000
 5OP  C18   C17  C16   113.02  3.000
 5OP  H182  C18  H181  106.36  3.000
 5OP  H182  C18  C19   109.96  3.000
 5OP  H181  C18  C19   109.13  3.000
 5OP  H182  C18  C17   109.24  3.000
 5OP  H181  C18  C17   108.97  3.000
 5OP  C19   C18  C17   112.97  3.000
 5OP  H192  C19  H191  105.36  3.000
 5OP  H192  C19  C20   109.26  3.000
 5OP  H191  C19  C20   107.10  3.000
 5OP  H192  C19  C18   109.73  3.000
 5OP  H191  C19  C18   109.06  3.000
 5OP  C20   C19  C18   115.80  3.000
 5OP  O5    C20  O3    126.09  3.000
 5OP  O5    C20  C19   117.60  3.000
 5OP  O3    C20  C19   116.28  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  Var_01  C13  C12  C11  C10   -16.60  30.0  1
 5OP  Var_02  C9   C8   C7   C6   -178.12   0.0  2
 5OP  Var_03  C16  C15  C14  C13    21.87  30.0  3
 5OP  Var_04  C17  C16  C15  C14  -179.30   0.0  2
 5OP  Var_05  C4   C3   C2   C1   -179.68  30.0  3
 5OP  Var_06  C5   C4   C3   C2   -178.05  30.0  3
 5OP  Var_07  C6   C5   C4   C3   -179.45  30.0  3
 5OP  Var_08  C7   C6   C5   C4   -171.22  30.0  3
 5OP  Var_09  C8   C7   C6   C5    177.25  30.0  2
 5OP  Var_10  C18  C17  C16  C15  -118.85  30.0  3
 5OP  Var_11  C19  C18  C17  C16  -171.37  30.0  3
 5OP  Var_12  C20  C19  C18  C17   -66.57  30.0  3
 5OP  Var_13  O3   C20  C19  C18   157.25  30.0  3
 5OP  Var_14  H11  C1   C2   C3   -179.69  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-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

