# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat May  2 07:49:07 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  58  24  .  2021-08-09  2021-08-09  
;
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  OH1   0  -0.598   10.2776   0.1634   2.0998
 EET  C20  C  C     0   0.549    9.4051  -0.5352   1.3781
 EET  O3   O  O     0  -0.445    9.3678  -1.7405   1.3822
 EET  C19  C  CH2   0  -0.580    8.4987   0.3588   0.5783
 EET  C18  C  CH2   0  -0.417    7.4449  -0.3931  -0.2178
 EET  C17  C  CH2   0  -0.494    6.5433   0.5670  -0.9963
 EET  C16  C  C1    0  -0.216    5.5169  -0.1631  -1.8049
 EET  C15  C  C1    0  -0.200    4.2038  -0.2157  -1.5865
 EET  C14  C  CH2   0  -0.576    3.4336   0.4698  -0.4947
 EET  C13  C  C1    0  -0.200    2.4925   1.4953  -1.0583
 EET  C12  C  C1    0  -0.208    1.1640   1.5115  -0.9657
 EET  C11  C  CH2   0  -0.583    0.2885   0.5282  -0.2424
 EET  C10  C  C1    0  -0.203   -0.2221   1.1379   1.0327
 EET  C9   C  C1    0  -0.203   -1.4583   1.5574   1.2977
 EET  C8   C  CH2   0  -0.546   -2.6464   1.4964   0.3897
 EET  C7   C  CH1   0   0.036   -3.7616   0.6001   0.9354
 EET  O2   O  OH1   0  -0.670   -4.1800   1.0102   2.2224
 EET  C6   C  CH1   0   0.026   -4.9422   0.5006  -0.0405
 EET  C5   C  CH2   0  -0.463   -5.9521  -0.5556   0.3915
 EET  C4   C  CH2   0  -0.410   -7.1017  -0.7515  -0.5912
 EET  C3   C  CH2   0  -0.407   -8.0508  -1.8637  -0.1640
 EET  C2   C  CH2   0  -0.418   -9.2156  -2.0639  -1.1265
 EET  C1   C  CH3   0  -0.662  -10.1538  -3.1822  -0.6946
 EET  O1   O  OH1   0  -0.673   -5.5467   1.7645  -0.2455
 EET  H1   H  HOH1  0   0.478   10.8498  -0.4372   2.6006
 EET  H2   H  HCH2  0   0.276    8.0270   1.0691   1.2648
 EET  H3   H  HCH2  0   0.279    9.1227   0.9658  -0.0860
 EET  H4   H  HCH2  0   0.232    7.9255  -1.0878  -0.9110
 EET  H5   H  HCH2  0   0.234    6.8287  -0.9960   0.4531
 EET  H6   H  HCH2  0   0.234    6.0732   1.2652  -0.3002
 EET  H7   H  HCH2  0   0.236    7.1625   1.1718  -1.6669
 EET  H8   H  H     0   0.234    5.9068  -0.7268  -2.6486
 EET  H9   H  H     0   0.236    3.5980  -0.8027  -2.2711
 EET  H10  H  HCH2  0   0.252    2.8859  -0.2796   0.0813
 EET  H11  H  HCH2  0   0.252    4.1110   0.9608   0.2081
 EET  H12  H  H     0   0.239    2.9721   2.3042  -1.6022
 EET  H14  H  H     0   0.239    0.6339   2.3427  -1.4213
 EET  H16  H  HCH2  0   0.253   -0.5362   0.2297  -0.8932
 EET  H17  H  HCH2  0   0.254    0.8408  -0.3834  -0.0046
 EET  H18  H  H     0   0.236    0.5329   1.2694   1.8026
 EET  H19  H  H     0   0.234   -1.6361   1.9927   2.2762
 EET  H20  H  HCH2  0   0.242   -3.0446   2.5077   0.2447
 EET  H21  H  HCH2  0   0.242   -2.3638   1.1369  -0.6017
 EET  H22  H  HCH1  0   0.228   -3.3556  -0.4095   1.0614
 EET  H23  H  HOH1  0   0.440   -4.3899   1.9496   2.1888
 EET  H24  H  HCH1  0   0.218   -4.5318   0.2059  -1.0137
 EET  H25  H  HCH2  0   0.223   -5.4214  -1.5051   0.5164
 EET  H26  H  HCH2  0   0.220   -6.3513  -0.2993   1.3795
 EET  H27  H  HCH2  0   0.211   -7.6649   0.1800  -0.6991
 EET  H28  H  HCH2  0   0.209   -6.6975  -0.9823  -1.5831
 EET  H29  H  HCH2  0   0.206   -7.4931  -2.8022  -0.0695
 EET  H30  H  HCH2  0   0.207   -8.4431  -1.6435   0.8352
 EET  H31  H  HCH2  0   0.210   -9.7751  -1.1275  -1.2146
 EET  H32  H  HCH2  0   0.210   -8.8259  -2.2793  -2.1263
 EET  H33  H  HCH3  0   0.215   -9.6238  -4.1339  -0.6218
 EET  H34  H  HCH3  0   0.216  -10.5914  -2.9754   0.2840
 EET  H35  H  HCH3  0   0.226  -10.9740  -3.3142  -1.4012
 EET  H36  H  HOH1  0   0.441   -6.1353   1.9448   0.4952

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  1.520  0.020  1.520
 EET  C18  C17  single  1.530  0.020  1.530
 EET  C19  C20  single  1.503  0.020  1.503
 EET  C16  C17  single  1.497  0.020  1.497
 EET  C16  C15  double  1.332  0.020  1.332
 EET  O3   C20  double  1.206  0.020  1.206
 EET  C20  O4   single  1.330  0.020  1.330
 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  1.497  0.020  1.497
 EET  C8   C7   single  1.531  0.020  1.531
 EET  C7   C6   single  1.535  0.020  1.535
 EET  C7   O2   single  1.414  0.020  1.414
 EET  C6   C5   single  1.524  0.020  1.524
 EET  C5   C4   single  1.525  0.020  1.525
 EET  C4   C3   single  1.523  0.020  1.523
 EET  C3   C2   single  1.524  0.020  1.524
 EET  C2   C1   single  1.522  0.020  1.522
 EET  C6   O1   single  1.416  0.020  1.416
 EET  O4   H1   single  0.850  0.020  0.980
 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  H1   O4   C20  110.01  3.000
 EET  C19  C20  O3   125.28  3.000
 EET  O3   C20  O4   122.90  3.000
 EET  C19  C20  O4   111.82  3.000
 EET  H3   C19  H2   105.44  3.000
 EET  H3   C19  C18  110.59  3.000
 EET  H2   C19  C18  110.53  3.000
 EET  H3   C19  C20  107.99  3.000
 EET  H2   C19  C20  108.18  3.000
 EET  C18  C19  C20  113.74  3.000
 EET  H5   C18  H4   106.67  3.000
 EET  H5   C18  C17  109.06  3.000
 EET  H4   C18  C17  109.59  3.000
 EET  H5   C18  C19  110.03  3.000
 EET  H4   C18  C19  109.98  3.000
 EET  C17  C18  C19  111.39  3.000
 EET  H7   C17  H6   106.30  3.000
 EET  H7   C17  C16  109.05  3.000
 EET  H6   C17  C16  111.16  3.000
 EET  H7   C17  C18  108.97  3.000
 EET  H6   C17  C18  109.30  3.000
 EET  C16  C17  C18  111.89  3.000
 EET  H8   C16  C15  117.41  3.000
 EET  H8   C16  C17  115.23  3.000
 EET  C15  C16  C17  127.34  3.000
 EET  H9   C15  C14  114.76  3.000
 EET  H9   C15  C16  117.88  3.000
 EET  C14  C15  C16  127.35  3.000
 EET  H11  C14  H10  106.26  3.000
 EET  H11  C14  C13  108.85  3.000
 EET  H10  C14  C13  110.61  3.000
 EET  H11  C14  C15  110.78  3.000
 EET  H10  C14  C15  109.11  3.000
 EET  C13  C14  C15  111.12  3.000
 EET  H12  C13  C12  117.79  3.000
 EET  H12  C13  C14  114.81  3.000
 EET  C12  C13  C14  127.40  3.000
 EET  H14  C12  C11  114.74  3.000
 EET  H14  C12  C13  117.84  3.000
 EET  C11  C12  C13  127.37  3.000
 EET  H17  C11  H16  106.46  3.000
 EET  H17  C11  C10  109.01  3.000
 EET  H16  C11  C10  111.10  3.000
 EET  H17  C11  C12  110.88  3.000
 EET  H16  C11  C12  109.40  3.000
 EET  C10  C11  C12  109.94  3.000
 EET  H18  C10  C9   117.77  3.000
 EET  H18  C10  C11  114.48  3.000
 EET  C9   C10  C11  127.72  3.000
 EET  H19  C9   C8   115.67  3.000
 EET  H19  C9   C10  117.23  3.000
 EET  C8   C9   C10  127.10  3.000
 EET  H21  C8   H20  106.12  3.000
 EET  H21  C8   C7   108.63  3.000
 EET  H20  C8   C7   108.81  3.000
 EET  H21  C8   C9   111.03  3.000
 EET  H20  C8   C9   109.32  3.000
 EET  C7   C8   C9   112.69  3.000
 EET  H22  C7   C6   107.36  3.000
 EET  H22  C7   O2   105.80  3.000
 EET  C6   C7   O2   111.71  3.000
 EET  H22  C7   C8   108.09  3.000
 EET  O2   C7   C8   111.72  3.000
 EET  C6   C7   C8   111.81  3.000
 EET  H23  O2   C7   108.40  3.000
 EET  H24  C6   O1   105.74  3.000
 EET  H24  C6   C5   108.27  3.000
 EET  O1   C6   C5   112.14  3.000
 EET  H24  C6   C7   107.09  3.000
 EET  O1   C6   C7   111.25  3.000
 EET  C5   C6   C7   111.99  3.000
 EET  H26  C5   H25  106.05  3.000
 EET  H26  C5   C4   109.65  3.000
 EET  H25  C5   C4   109.12  3.000
 EET  H26  C5   C6   109.56  3.000
 EET  H25  C5   C6   108.19  3.000
 EET  C4   C5   C6   113.95  3.000
 EET  H28  C4   H27  106.26  3.000
 EET  H28  C4   C3   109.26  3.000
 EET  H27  C4   C3   109.18  3.000
 EET  H28  C4   C5   109.41  3.000
 EET  H27  C4   C5   110.02  3.000
 EET  C3   C4   C5   112.50  3.000
 EET  H30  C3   H29  106.00  3.000
 EET  H30  C3   C2   109.19  3.000
 EET  H29  C3   C2   109.32  3.000
 EET  H30  C3   C4   109.39  3.000
 EET  H29  C3   C4   109.42  3.000
 EET  C2   C3   C4   113.26  3.000
 EET  H32  C2   H31  106.07  3.000
 EET  H32  C2   C1   109.52  3.000
 EET  H31  C2   C1   109.66  3.000
 EET  H32  C2   C3   109.31  3.000
 EET  H31  C2   C3   109.22  3.000
 EET  C1   C2   C3   112.85  3.000
 EET  H35  C1   H34  107.59  3.000
 EET  H35  C1   H33  107.62  3.000
 EET  H34  C1   H33  107.46  3.000
 EET  H35  C1   C2   111.63  3.000
 EET  H34  C1   C2   111.24  3.000
 EET  H33  C1   C2   111.10  3.000
 EET  H36  O1   C6   108.47  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  CONST_01  H1   O4   C20  O3      0.00   0.0  0
 EET  Var_01    C14  C15  C16  C17     1.48   0.0  2
 EET  Var_02    C11  C12  C13  C14     1.86   0.0  2
 EET  Var_03    C8   C9   C10  C11     1.26   0.0  2
 EET  Var_04    C18  C19  C20  O4   -177.54  30.0  2
 EET  Var_05    C17  C18  C19  C20   179.30  30.0  1
 EET  Var_06    C16  C17  C18  C19   178.93  30.0  3
 EET  Var_07    C15  C16  C17  C18   109.52  30.0  1
 EET  Var_08    C13  C14  C15  C16   114.77  30.0  3
 EET  Var_09    C12  C13  C14  C15   118.08  30.0  3
 EET  Var_10    C10  C11  C12  C13   105.20  30.0  3
 EET  Var_11    C9   C10  C11  C12   107.36  30.0  2
 EET  Var_12    C7   C8   C9   C10   116.62  30.0  3
 EET  Var_13    C3   C4   C5   C6    177.00  30.0  3
 EET  Var_14    C2   C3   C4   C5    179.36  30.0  3
 EET  Var_15    C1   C2   C3   C4    179.69  30.0  3
 EET  Var_16    H33  C1   C2   C3    -59.34  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-1  H1   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

