# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue May 19 18:28:34 2020
#   Inital geometry file: a 135 line input string
#   Ligand name: (5E,8E,11Z,13E)-15-oxoicosa-5,8,11,13-tetraenoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCCCC(=O)\C=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
 OCR  OCR  '(5E,8E,11Z,13E)-15-oxoicosa-5,8,11,13-tetraenoic acid'  ligand  53  23  .  2021-08-19  2021-08-19  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_OCR
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
 OCR  C1    C  CH3   0  -0.662   11.9075   0.2932   0.0070
 OCR  C2    C  CH2   0  -0.421   10.5580   0.7821  -0.5001
 OCR  C3    C  CH2   0  -0.409    9.3838   0.1445   0.2317
 OCR  C4    C  CH2   0  -0.416    8.0319   0.6197  -0.2857
 OCR  C5    C  CH2   0  -0.569    6.8745   0.0095   0.4858
 OCR  C6    C  C     0   0.380    5.5027   0.3907  -0.0078
 OCR  O7    O  O     0  -0.423    5.3339   1.0071  -1.0435
 OCR  C8    C  C1    0  -0.367    4.3775  -0.0412   0.8421
 OCR  C9    C  C1    0  -0.192    3.0974   0.1627   0.4927
 OCR  C11   C  C1    0  -0.255    1.9734  -0.2256   1.3142
 OCR  C12   C  C1    0  -0.181    0.6816  -0.0486   1.0000
 OCR  C13   C  CH2   0  -0.572    0.1177   0.5365  -0.2576
 OCR  C14   C  C1    0  -0.205   -0.7904  -0.4451  -0.9423
 OCR  C15   C  C1    0  -0.199   -2.0756  -0.2245  -1.1998
 OCR  C16   C  CH2   0  -0.555   -2.9986  -1.1956  -1.8751
 OCR  C17   C  C1    0  -0.209   -4.1935  -1.4951  -1.0170
 OCR  C18   C  C1    0  -0.206   -5.4492  -1.2119  -1.3493
 OCR  C19   C  CH2   0  -0.483   -6.6491  -1.4527  -0.4896
 OCR  C20   C  CH2   0  -0.420   -7.3754  -0.1480  -0.1604
 OCR  C21   C  CH2   0  -0.580   -8.6347  -0.3937   0.6541
 OCR  C22   C  C     0   0.550   -9.4060   0.8598   0.9612
 OCR  O23   O  OH1   0  -0.598  -10.5254   0.6023   1.6329
 OCR  O24   O  O     0  -0.446   -9.0741   1.9762   0.6483
 OCR  H1    H  HCH3  0   0.216   12.0322   0.5110   1.0694
 OCR  H1A   H  HCH3  0   0.216   12.0089  -0.7864  -0.1196
 OCR  H1B   H  HCH3  0   0.226   12.7324   0.7670  -0.5264
 OCR  H2    H  HCH2  0   0.212   10.4989   1.8700  -0.3962
 OCR  H2A   H  HCH2  0   0.212   10.4717   0.5761  -1.5714
 OCR  H3    H  HCH2  0   0.210    9.4469  -0.9455   0.1393
 OCR  H3A   H  HCH2  0   0.210    9.4650   0.3609   1.3027
 OCR  H4    H  HCH2  0   0.220    7.9799   1.7105  -0.2187
 OCR  H4A   H  HCH2  0   0.221    7.9435   0.3749  -1.3473
 OCR  H5    H  HCH2  0   0.269    6.9291  -1.0868   0.4614
 OCR  H5A   H  HCH2  0   0.261    6.9402   0.2637   1.5498
 OCR  H8    H  H     0   0.259    4.6201  -0.5350   1.7774
 OCR  H9    H  H     0   0.267    2.8961   0.6531  -0.4538
 OCR  H11   H  H     0   0.255    2.2097  -0.6861   2.2679
 OCR  H12   H  H     0   0.260   -0.0584  -0.3764   1.7235
 OCR  H13   H  HCH2  0   0.264   -0.4494   1.4383  -0.0071
 OCR  H13A  H  HCH2  0   0.258    0.9117   0.8445  -0.9408
 OCR  H14   H  H     0   0.243   -0.3403  -1.3916  -1.2331
 OCR  H15   H  H     0   0.239   -2.5199   0.7234  -0.9034
 OCR  H16   H  HCH2  0   0.247   -3.3366  -0.7792  -2.8295
 OCR  H16A  H  HCH2  0   0.246   -2.4545  -2.1169  -2.1039
 OCR  H17   H  H     0   0.235   -3.9861  -1.9522  -0.0518
 OCR  H18   H  H     0   0.231   -5.6431  -0.7486  -2.3151
 OCR  H19   H  HCH2  0   0.232   -7.3435  -2.1208  -1.0112
 OCR  H19A  H  HCH2  0   0.233   -6.3544  -1.9634   0.4317
 OCR  H20   H  HCH2  0   0.234   -6.6981   0.5130   0.3850
 OCR  H20A  H  HCH2  0   0.231   -7.6329   0.3663  -1.0900
 OCR  H21   H  HCH2  0   0.276   -9.3026  -1.0848   0.1303
 OCR  H21A  H  HCH2  0   0.278   -8.3917  -0.8844   1.6023
 OCR  HO23  H  HOH1  0   0.478  -10.9974   1.4290   1.8117

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
 OCR  C1   C2    single  1.522  0.020  1.522
 OCR  C2   C3    single  1.523  0.020  1.523
 OCR  C3   C4    single  1.524  0.020  1.524
 OCR  C4   C5    single  1.519  0.020  1.519
 OCR  C5   C6    single  1.507  0.020  1.507
 OCR  C6   O7    double  1.217  0.020  1.217
 OCR  C6   C8    single  1.475  0.020  1.475
 OCR  C8   C9    double  1.343  0.020  1.343
 OCR  C9   C11   single  1.445  0.020  1.445
 OCR  C11  C12   double  1.341  0.020  1.341
 OCR  C12  C13   single  1.497  0.020  1.497
 OCR  C13  C14   single  1.502  0.020  1.502
 OCR  C14  C15   double  1.329  0.020  1.329
 OCR  C15  C16   single  1.500  0.020  1.500
 OCR  C16  C17   single  1.501  0.020  1.501
 OCR  C17  C18   double  1.329  0.020  1.329
 OCR  C18  C19   single  1.496  0.020  1.496
 OCR  C19  C20   single  1.529  0.020  1.529
 OCR  C20  C21   single  1.520  0.020  1.520
 OCR  C21  C22   single  1.503  0.020  1.503
 OCR  C22  O23   single  1.331  0.020  1.331
 OCR  C22  O24   double  1.206  0.020  1.206
 OCR  C1   H1    single  0.970  0.020  1.090
 OCR  C1   H1A   single  0.970  0.020  1.090
 OCR  C1   H1B   single  0.970  0.020  1.090
 OCR  C2   H2    single  0.970  0.020  1.090
 OCR  C2   H2A   single  0.970  0.020  1.090
 OCR  C3   H3    single  0.970  0.020  1.090
 OCR  C3   H3A   single  0.970  0.020  1.090
 OCR  C4   H4    single  0.970  0.020  1.090
 OCR  C4   H4A   single  0.970  0.020  1.090
 OCR  C5   H5    single  0.970  0.020  1.090
 OCR  C5   H5A   single  0.970  0.020  1.090
 OCR  C8   H8    single  0.930  0.020  1.080
 OCR  C9   H9    single  0.930  0.020  1.080
 OCR  C11  H11   single  0.930  0.020  1.080
 OCR  C12  H12   single  0.930  0.020  1.080
 OCR  C13  H13   single  0.970  0.020  1.090
 OCR  C13  H13A  single  0.970  0.020  1.090
 OCR  C14  H14   single  0.930  0.020  1.080
 OCR  C15  H15   single  0.930  0.020  1.080
 OCR  C16  H16   single  0.970  0.020  1.090
 OCR  C16  H16A  single  0.970  0.020  1.090
 OCR  C17  H17   single  0.930  0.020  1.080
 OCR  C18  H18   single  0.930  0.020  1.080
 OCR  C19  H19   single  0.970  0.020  1.090
 OCR  C19  H19A  single  0.970  0.020  1.090
 OCR  C20  H20   single  0.970  0.020  1.090
 OCR  C20  H20A  single  0.970  0.020  1.090
 OCR  C21  H21   single  0.970  0.020  1.090
 OCR  C21  H21A  single  0.970  0.020  1.090
 OCR  O23  HO23  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
 OCR  H1B   C1   H1A  107.62  3.000
 OCR  H1B   C1   H1   107.64  3.000
 OCR  H1A   C1   H1   107.43  3.000
 OCR  H1B   C1   C2   111.59  3.000
 OCR  H1A   C1   C2   111.18  3.000
 OCR  H1    C1   C2   111.18  3.000
 OCR  H2A   C2   H2   106.00  3.000
 OCR  H2A   C2   C3   109.31  3.000
 OCR  H2    C2   C3   109.19  3.000
 OCR  H2A   C2   C1   109.61  3.000
 OCR  H2    C2   C1   109.61  3.000
 OCR  C3    C2   C1   112.89  3.000
 OCR  H3A   C3   H3   105.94  3.000
 OCR  H3A   C3   C4   109.64  3.000
 OCR  H3    C3   C4   109.43  3.000
 OCR  H3A   C3   C2   109.25  3.000
 OCR  H3    C3   C2   109.36  3.000
 OCR  C4    C3   C2   112.97  3.000
 OCR  H4A   C4   H4   106.20  3.000
 OCR  H4A   C4   C5   109.98  3.000
 OCR  H4    C4   C5   109.46  3.000
 OCR  H4A   C4   C3   109.38  3.000
 OCR  H4    C4   C3   109.41  3.000
 OCR  C5    C4   C3   112.23  3.000
 OCR  H5A   C5   H5   104.49  3.000
 OCR  H5A   C5   C6   108.30  3.000
 OCR  H5    C5   C6   106.89  3.000
 OCR  H5A   C5   C4   110.75  3.000
 OCR  H5    C5   C4   110.61  3.000
 OCR  C6    C5   C4   115.19  3.000
 OCR  C8    C6   O7   122.20  3.000
 OCR  C8    C6   C5   115.58  3.000
 OCR  O7    C6   C5   122.22  3.000
 OCR  H8    C8   C9   120.43  3.000
 OCR  H8    C8   C6   117.35  3.000
 OCR  C9    C8   C6   122.21  3.000
 OCR  H9    C9   C11  118.23  3.000
 OCR  H9    C9   C8   118.20  3.000
 OCR  C11   C9   C8   123.56  3.000
 OCR  H11   C11  C12  118.14  3.000
 OCR  H11   C11  C9   116.37  3.000
 OCR  C12   C11  C9   125.48  3.000
 OCR  H12   C12  C13  114.90  3.000
 OCR  H12   C12  C11  117.42  3.000
 OCR  C13   C12  C11  127.67  3.000
 OCR  H13A  C13  H13  106.72  3.000
 OCR  H13A  C13  C14  109.80  3.000
 OCR  H13   C13  C14  109.24  3.000
 OCR  H13A  C13  C12  111.21  3.000
 OCR  H13   C13  C12  108.96  3.000
 OCR  C14   C13  C12  110.80  3.000
 OCR  H14   C14  C15  119.51  3.000
 OCR  H14   C14  C13  116.13  3.000
 OCR  C15   C14  C13  124.36  3.000
 OCR  H15   C15  C16  115.80  3.000
 OCR  H15   C15  C14  119.12  3.000
 OCR  C16   C15  C14  125.08  3.000
 OCR  H16A  C16  H16  106.95  3.000
 OCR  H16A  C16  C17  110.32  3.000
 OCR  H16   C16  C17  109.17  3.000
 OCR  H16A  C16  C15  109.46  3.000
 OCR  H16   C16  C15  109.64  3.000
 OCR  C17   C16  C15  111.19  3.000
 OCR  H17   C17  C18  119.43  3.000
 OCR  H17   C17  C16  116.05  3.000
 OCR  C18   C17  C16  124.50  3.000
 OCR  H18   C18  C19  115.82  3.000
 OCR  H18   C18  C17  118.73  3.000
 OCR  C19   C18  C17  125.44  3.000
 OCR  H19A  C19  H19  106.67  3.000
 OCR  H19A  C19  C20  110.18  3.000
 OCR  H19   C19  C20  108.77  3.000
 OCR  H19A  C19  C18  110.07  3.000
 OCR  H19   C19  C18  109.46  3.000
 OCR  C20   C19  C18  111.56  3.000
 OCR  H20A  C20  H20  106.62  3.000
 OCR  H20A  C20  C21  109.67  3.000
 OCR  H20   C20  C21  110.12  3.000
 OCR  H20A  C20  C19  109.28  3.000
 OCR  H20   C20  C19  109.23  3.000
 OCR  C21   C20  C19  111.78  3.000
 OCR  H21A  C21  H21  105.48  3.000
 OCR  H21A  C21  C22  108.10  3.000
 OCR  H21   C21  C22  108.12  3.000
 OCR  H21A  C21  C20  110.65  3.000
 OCR  H21   C21  C20  110.56  3.000
 OCR  C22   C21  C20  113.56  3.000
 OCR  O24   C22  O23  122.79  3.000
 OCR  O24   C22  C21  125.29  3.000
 OCR  O23   C22  C21  111.92  3.000
 OCR  HO23  O23  C22  109.75  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
 OCR  CONST_01  HO23  O23  C22  C21   180.00   0.0  0
 OCR  Var_01    C11   C9   C8   C6   -178.80   0.0  2
 OCR  Var_02    C13   C12  C11  C9      2.05   0.0  2
 OCR  Var_03    C16   C15  C14  C13  -179.63   0.0  2
 OCR  Var_04    C19   C18  C17  C16  -177.51   0.0  2
 OCR  Var_05    C4    C3   C2   C1   -179.30  30.0  3
 OCR  Var_06    C5    C4   C3   C2   -178.09  30.0  3
 OCR  Var_07    C6    C5   C4   C3   -177.59  30.0  3
 OCR  Var_08    O7    C6   C5   C4      8.57  30.0  3
 OCR  Var_09    C9    C8   C6   C5   -176.28  30.0  2
 OCR  Var_10    C12   C11  C9   C8   -179.56  30.0  2
 OCR  Var_11    C14   C13  C12  C11   121.41  30.0  3
 OCR  Var_12    C15   C14  C13  C12   120.47  30.0  3
 OCR  Var_13    C17   C16  C15  C14   123.21  30.0  3
 OCR  Var_14    C18   C17  C16  C15   117.18  30.0  3
 OCR  Var_15    C20   C19  C18  C17   118.67  30.0  3
 OCR  Var_16    C21   C20  C19  C18   177.12  30.0  3
 OCR  Var_17    C22   C21  C20  C19  -178.05  30.0  3
 OCR  Var_18    O23   C22  C21  C20   177.74  30.0  3
 OCR  Var_19    H1    C1   C2   C3    -59.46  30.0  3

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
 OCR  plan-1  C5    0.020
 OCR  plan-1  C6    0.020
 OCR  plan-1  O7    0.020
 OCR  plan-1  C8    0.020
 OCR  plan-2  C21   0.020
 OCR  plan-2  C22   0.020
 OCR  plan-2  O23   0.020
 OCR  plan-2  O24   0.020
 OCR  plan-2  HO23  0.020
 OCR  plan-3  C6    0.020
 OCR  plan-3  C8    0.020
 OCR  plan-3  C9    0.020
 OCR  plan-3  C11   0.020
 OCR  plan-3  H8    0.020
 OCR  plan-3  H9    0.020
 OCR  plan-4  C9    0.020
 OCR  plan-4  C11   0.020
 OCR  plan-4  C12   0.020
 OCR  plan-4  C13   0.020
 OCR  plan-4  H11   0.020
 OCR  plan-4  H12   0.020
 OCR  plan-5  C13   0.020
 OCR  plan-5  C14   0.020
 OCR  plan-5  C15   0.020
 OCR  plan-5  C16   0.020
 OCR  plan-5  H14   0.020
 OCR  plan-5  H15   0.020
 OCR  plan-6  C16   0.020
 OCR  plan-6  C17   0.020
 OCR  plan-6  C18   0.020
 OCR  plan-6  C19   0.020
 OCR  plan-6  H17   0.020
 OCR  plan-6  H18   0.020

