# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr 27 00:16:29 2020
#   Inital geometry file: a 138 line input string
#   Ligand name: (5~{Z},11~{Z},14~{R},15~{R})-14,15-bis(oxidanyl)icosa-5,8,11-trienoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCCC[C@@H](O)[C@H](O)C\C=C/C/C=C\C\C=C/CCCC(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
 EET  EET  '(5~{Z},11~{Z},14~{R},15~{R})-14,15-bis(oxidanyl)icosa-5,8,11-trienoic acid'  ligand  57  24  .  2021-08-08  2021-08-08  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_EET
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
 EET  O4   O  OC    -1  -0.634   10.7700  -0.0973   1.4153
 EET  C20  C  C      0   0.410    9.7629  -0.6309   0.9025
 EET  O3   O  O      0  -0.609    9.5425  -1.8548   0.8152
 EET  C19  C  CH2    0  -0.580    8.7030   0.3347   0.3424
 EET  C18  C  CH2    0  -0.403    7.5253  -0.3106  -0.3685
 EET  C17  C  CH2    0  -0.486    6.5138   0.7200  -0.8768
 EET  C16  C  C1     0  -0.207    5.3768   0.0770  -1.6059
 EET  C15  C  C1     0  -0.209    4.0840   0.0885  -1.2840
 EET  C14  C  CH2    0  -0.576    3.4359   0.7920  -0.1256
 EET  C13  C  C1     0  -0.204    2.5441   1.8964  -0.6152
 EET  C12  C  C1     0  -0.205    1.2163   1.9642  -0.5365
 EET  C11  C  CH2    0  -0.578    0.2846   0.9760   0.1044
 EET  C10  C  C1     0  -0.207   -0.3774   1.5894   1.3058
 EET  C9   C  C1     0  -0.204   -1.6598   1.9230   1.4450
 EET  C8   C  CH2    0  -0.538   -2.7568   1.7303   0.4457
 EET  C7   C  CH1    0   0.031   -3.8967   0.8649   0.9910
 EET  O2   O  OH1    0  -0.670   -4.5147   1.4645   2.1129
 EET  C6   C  CH1    0   0.023   -4.9094   0.4962  -0.1003
 EET  C5   C  CH2    0  -0.457   -5.9627  -0.4858   0.3993
 EET  C4   C  CH2    0  -0.411   -6.8547  -1.0376  -0.7060
 EET  C3   C  CH2    0  -0.408   -7.8953  -2.0216  -0.1859
 EET  C2   C  CH2    0  -0.418   -8.7369  -2.6472  -1.2907
 EET  C1   C  CH3    0  -0.663   -9.7841  -3.6167  -0.7603
 EET  O1   O  OH1    0  -0.673   -5.4910   1.6468  -0.6865
 EET  H2   H  HCH2   0   0.219    8.3353   0.9490   1.1734
 EET  H3   H  HCH2   0   0.216    9.2023   1.0413  -0.3304
 EET  H4   H  HCH2   0   0.206    7.8814  -0.9102  -1.2113
 EET  H5   H  HCH2   0   0.209    7.0181  -1.0056   0.3050
 EET  H6   H  HCH2   0   0.225    6.1571   1.3249  -0.0398
 EET  H7   H  HCH2   0   0.225    7.0253   1.4112  -1.5568
 EET  H8   H  H      0   0.228    5.6615  -0.4833  -2.4935
 EET  H9   H  H      0   0.234    3.3951  -0.4476  -1.9311
 EET  H10  H  HCH2   0   0.250    2.8675   0.0683   0.4628
 EET  H11  H  HCH2   0   0.252    4.1899   1.2112   0.5439
 EET  H12  H  H      0   0.238    3.0623   2.7138  -1.1086
 EET  H14  H  H      0   0.238    0.7296   2.8408  -0.9545
 EET  H16  H  HCH2   0   0.251   -0.4593   0.6567  -0.6290
 EET  H17  H  HCH2   0   0.252    0.8233   0.0766   0.4111
 EET  H18  H  H      0   0.236    0.2940   1.8022   2.1328
 EET  H19  H  H      0   0.235   -1.9566   2.3795   2.3843
 EET  H20  H  HCH2   0   0.241   -3.1608   2.7068   0.1530
 EET  H21  H  HCH2   0   0.242   -2.3755   1.2756  -0.4708
 EET  H22  H  HCH1   0   0.229   -3.4667  -0.0745   1.3558
 EET  H23  H  HOH1   0   0.440   -4.7624   2.3656   1.8799
 EET  H24  H  HCH1   0   0.218   -4.3414   0.0100  -0.9026
 EET  H25  H  HCH2   0   0.223   -5.4522  -1.3178   0.8946
 EET  H26  H  HCH2   0   0.220   -6.5770  -0.0073   1.1703
 EET  H27  H  HCH2   0   0.213   -7.3599  -0.2183  -1.2251
 EET  H28  H  HCH2   0   0.208   -6.2288  -1.5348  -1.4558
 EET  H29  H  HCH2   0   0.206   -7.3940  -2.8154   0.3791
 EET  H30  H  HCH2   0   0.207   -8.5532  -1.5129   0.5277
 EET  H31  H  HCH2   0   0.210   -9.2281  -1.8562  -1.8658
 EET  H32  H  HCH2   0   0.210   -8.0777  -3.1667  -1.9930
 EET  H33  H  HCH3   0   0.215   -9.3209  -4.4245  -0.1905
 EET  H34  H  HCH3   0   0.216  -10.4900  -3.1117  -0.0979
 EET  H35  H  HCH3   0   0.226  -10.3579  -4.0701  -1.5695
 EET  H36  H  HOH1   0   0.441   -6.1934   1.9638  -0.1089

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
 EET  C18  C19  single  1.519  0.020  1.519
 EET  C18  C17  single  1.531  0.020  1.531
 EET  C19  C20  single  1.539  0.020  1.539
 EET  C16  C17  single  1.496  0.020  1.496
 EET  C16  C15  double  1.332  0.020  1.332
 EET  O3   C20  deloc   1.247  0.020  1.247
 EET  C20  O4   deloc   1.250  0.020  1.250
 EET  C15  C14  single  1.502  0.020  1.502
 EET  C14  C13  single  1.502  0.020  1.502
 EET  C13  C12  double  1.332  0.020  1.332
 EET  C10  C11  single  1.503  0.020  1.503
 EET  C10  C9   double  1.332  0.020  1.332
 EET  C12  C11  single  1.502  0.020  1.502
 EET  C9   C8   single  1.496  0.020  1.496
 EET  C8   C7   single  1.532  0.020  1.532
 EET  C7   C6   single  1.534  0.020  1.534
 EET  C7   O2   single  1.414  0.020  1.414
 EET  C6   C5   single  1.524  0.020  1.524
 EET  C5   C4   single  1.524  0.020  1.524
 EET  C4   C3   single  1.524  0.020  1.524
 EET  C3   C2   single  1.523  0.020  1.523
 EET  C2   C1   single  1.523  0.020  1.523
 EET  C6   O1   single  1.416  0.020  1.416
 EET  C19  H2   single  0.970  0.020  1.090
 EET  C19  H3   single  0.970  0.020  1.090
 EET  C18  H4   single  0.970  0.020  1.090
 EET  C18  H5   single  0.970  0.020  1.090
 EET  C17  H6   single  0.970  0.020  1.090
 EET  C17  H7   single  0.970  0.020  1.090
 EET  C16  H8   single  0.930  0.020  1.080
 EET  C15  H9   single  0.930  0.020  1.080
 EET  C14  H10  single  0.970  0.020  1.090
 EET  C14  H11  single  0.970  0.020  1.090
 EET  C13  H12  single  0.930  0.020  1.080
 EET  C12  H14  single  0.930  0.020  1.080
 EET  C11  H16  single  0.970  0.020  1.090
 EET  C11  H17  single  0.970  0.020  1.090
 EET  C10  H18  single  0.930  0.020  1.080
 EET  C9   H19  single  0.930  0.020  1.080
 EET  C8   H20  single  0.970  0.020  1.090
 EET  C8   H21  single  0.970  0.020  1.090
 EET  C7   H22  single  0.970  0.020  1.090
 EET  O2   H23  single  0.850  0.020  0.980
 EET  C6   H24  single  0.970  0.020  1.090
 EET  C5   H25  single  0.970  0.020  1.090
 EET  C5   H26  single  0.970  0.020  1.090
 EET  C4   H27  single  0.970  0.020  1.090
 EET  C4   H28  single  0.970  0.020  1.090
 EET  C3   H29  single  0.970  0.020  1.090
 EET  C3   H30  single  0.970  0.020  1.090
 EET  C2   H31  single  0.970  0.020  1.090
 EET  C2   H32  single  0.970  0.020  1.090
 EET  C1   H33  single  0.970  0.020  1.090
 EET  C1   H34  single  0.970  0.020  1.090
 EET  C1   H35  single  0.970  0.020  1.090
 EET  O1   H36  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
 EET  C19  C20  O3   117.95  3.000
 EET  O3   C20  O4   126.18  3.000
 EET  C19  C20  O4   115.87  3.000
 EET  H3   C19  H2   104.87  3.000
 EET  H3   C19  C18  109.85  3.000
 EET  H2   C19  C18  109.41  3.000
 EET  H3   C19  C20  108.31  3.000
 EET  H2   C19  C20  107.85  3.000
 EET  C18  C19  C20  115.95  3.000
 EET  H5   C18  H4   106.10  3.000
 EET  H5   C18  C17  109.04  3.000
 EET  H4   C18  C17  109.17  3.000
 EET  H5   C18  C19  109.97  3.000
 EET  H4   C18  C19  109.93  3.000
 EET  C17  C18  C19  112.43  3.000
 EET  H7   C17  H6   106.17  3.000
 EET  H7   C17  C16  108.86  3.000
 EET  H6   C17  C16  111.30  3.000
 EET  H7   C17  C18  108.79  3.000
 EET  H6   C17  C18  109.52  3.000
 EET  C16  C17  C18  112.00  3.000
 EET  H8   C16  C15  117.11  3.000
 EET  H8   C16  C17  114.85  3.000
 EET  C15  C16  C17  128.03  3.000
 EET  H9   C15  C14  114.63  3.000
 EET  H9   C15  C16  117.84  3.000
 EET  C14  C15  C16  127.51  3.000
 EET  H11  C14  H10  106.47  3.000
 EET  H11  C14  C13  109.12  3.000
 EET  H10  C14  C13  110.73  3.000
 EET  H11  C14  C15  110.77  3.000
 EET  H10  C14  C15  109.24  3.000
 EET  C13  C14  C15  110.44  3.000
 EET  H12  C13  C12  117.65  3.000
 EET  H12  C13  C14  114.72  3.000
 EET  C12  C13  C14  127.61  3.000
 EET  H14  C12  C11  114.66  3.000
 EET  H14  C12  C13  117.71  3.000
 EET  C11  C12  C13  127.61  3.000
 EET  H17  C11  H16  106.48  3.000
 EET  H17  C11  C10  109.21  3.000
 EET  H16  C11  C10  110.86  3.000
 EET  H17  C11  C12  110.83  3.000
 EET  H16  C11  C12  109.16  3.000
 EET  C10  C11  C12  110.24  3.000
 EET  H18  C10  C9   117.79  3.000
 EET  H18  C10  C11  114.60  3.000
 EET  C9   C10  C11  127.58  3.000
 EET  H19  C9   C8   115.56  3.000
 EET  H19  C9   C10  117.31  3.000
 EET  C8   C9   C10  127.12  3.000
 EET  H21  C8   H20  105.99  3.000
 EET  H21  C8   C7   108.87  3.000
 EET  H20  C8   C7   108.91  3.000
 EET  H21  C8   C9   110.99  3.000
 EET  H20  C8   C9   109.49  3.000
 EET  C7   C8   C9   112.37  3.000
 EET  H22  C7   C6   106.85  3.000
 EET  H22  C7   O2   105.72  3.000
 EET  C6   C7   O2   112.20  3.000
 EET  H22  C7   C8   108.11  3.000
 EET  O2   C7   C8   111.60  3.000
 EET  C6   C7   C8   111.96  3.000
 EET  H23  O2   C7   108.49  3.000
 EET  H24  C6   O1   105.67  3.000
 EET  H24  C6   C5   108.18  3.000
 EET  O1   C6   C5   112.05  3.000
 EET  H24  C6   C7   106.57  3.000
 EET  O1   C6   C7   111.74  3.000
 EET  C5   C6   C7   112.20  3.000
 EET  H26  C5   H25  105.97  3.000
 EET  H26  C5   C4   109.90  3.000
 EET  H25  C5   C4   109.03  3.000
 EET  H26  C5   C6   109.67  3.000
 EET  H25  C5   C6   108.41  3.000
 EET  C4   C5   C6   113.58  3.000
 EET  H28  C4   H27  106.20  3.000
 EET  H28  C4   C3   109.31  3.000
 EET  H27  C4   C3   109.29  3.000
 EET  H28  C4   C5   109.04  3.000
 EET  H27  C4   C5   110.09  3.000
 EET  C3   C4   C5   112.71  3.000
 EET  H30  C3   H29  105.98  3.000
 EET  H30  C3   C2   109.34  3.000
 EET  H29  C3   C2   109.22  3.000
 EET  H30  C3   C4   109.42  3.000
 EET  H29  C3   C4   109.35  3.000
 EET  C2   C3   C4   113.26  3.000
 EET  H32  C2   H31  106.03  3.000
 EET  H32  C2   C1   109.61  3.000
 EET  H31  C2   C1   109.55  3.000
 EET  H32  C2   C3   109.12  3.000
 EET  H31  C2   C3   109.41  3.000
 EET  C1   C2   C3   112.89  3.000
 EET  H35  C1   H34  107.60  3.000
 EET  H35  C1   H33  107.63  3.000
 EET  H34  C1   H33  107.45  3.000
 EET  H35  C1   C2   111.60  3.000
 EET  H34  C1   C2   111.19  3.000
 EET  H33  C1   C2   111.17  3.000
 EET  H36  O1   C6   108.58  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
 EET  Var_01  C14  C15  C16  C17     2.18   0.0  2
 EET  Var_02  C11  C12  C13  C14     2.36   0.0  2
 EET  Var_03  C8   C9   C10  C11     1.81   0.0  2
 EET  Var_04  C18  C19  C20  O4    175.84  30.0  2
 EET  Var_05  C17  C18  C19  C20   179.28  30.0  2
 EET  Var_06  C16  C17  C18  C19   178.51  30.0  3
 EET  Var_07  C15  C16  C17  C18   117.38  30.0  1
 EET  Var_08  C13  C14  C15  C16   113.07  30.0  3
 EET  Var_09  C12  C13  C14  C15   112.69  30.0  3
 EET  Var_10  C10  C11  C12  C13   113.48  30.0  3
 EET  Var_11  C9   C10  C11  C12   110.96  30.0  1
 EET  Var_12  C7   C8   C9   C10   121.24  30.0  3
 EET  Var_13  C3   C4   C5   C6    179.73  30.0  3
 EET  Var_14  C2   C3   C4   C5   -176.40  30.0  3
 EET  Var_15  C1   C2   C3   C4   -179.35  30.0  3
 EET  Var_16  H33  C1   C2   C3    -58.44  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
 EET  chir_01  C7  C8  C6  O2  positiv
 EET  chir_02  C6  O1  C7  C5  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
 EET  plan-1  O4   0.020
 EET  plan-1  C20  0.020
 EET  plan-1  O3   0.020
 EET  plan-1  C19  0.020
 EET  plan-2  C17  0.020
 EET  plan-2  C16  0.020
 EET  plan-2  C15  0.020
 EET  plan-2  C14  0.020
 EET  plan-2  H8   0.020
 EET  plan-2  H9   0.020
 EET  plan-3  C14  0.020
 EET  plan-3  C13  0.020
 EET  plan-3  C12  0.020
 EET  plan-3  C11  0.020
 EET  plan-3  H12  0.020
 EET  plan-3  H14  0.020
 EET  plan-4  C11  0.020
 EET  plan-4  C10  0.020
 EET  plan-4  C9   0.020
 EET  plan-4  C8   0.020
 EET  plan-4  H18  0.020
 EET  plan-4  H19  0.020

