# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue May 19 18:42:58 2020
#   Inital geometry file: a 135 line input string
#   Ligand name: (5E,9E,11E,14E)-8-oxoicosa-5,9,11,14-tetraenoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCCC\C=C\C\C=C\C=C\C(=O)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
 OCX  OCX  '(5E,9E,11E,14E)-8-oxoicosa-5,9,11,14-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_OCX
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
 OCX  C1    C  CH3   0  -0.662   9.0944   4.4737  -0.0544
 OCX  C2    C  CH2   0  -0.420   8.3147   3.3338   0.5866
 OCX  C3    C  CH2   0  -0.408   8.1617   2.1328  -0.3384
 OCX  C4    C  CH2   0  -0.416   7.3671   0.9917   0.2841
 OCX  C5    C  CH2   0  -0.482   7.2315  -0.2107  -0.6505
 OCX  C6    C  C1    0  -0.197   6.4561  -1.3299  -0.0329
 OCX  C7    C  C1    0  -0.216   5.3324  -1.8415  -0.5265
 OCX  C8    C  CH2   0  -0.567   4.5356  -2.9455   0.1111
 OCX  C9    C  C1    0  -0.183   3.1939  -2.4376   0.5309
 OCX  C10   C  C1    0  -0.246   2.0315  -2.7965  -0.0286
 OCX  C11   C  C1    0  -0.177   0.7652  -2.2398   0.3842
 OCX  C13   C  C1    0  -0.377  -0.4164  -2.5645  -0.1654
 OCX  C14   C  C     0   0.374  -1.6839  -1.9646   0.2806
 OCX  O15   O  O     0  -0.414  -1.7455  -1.1480   1.1795
 OCX  C16   C  CH2   0  -0.645  -2.9159  -2.4308  -0.4631
 OCX  C17   C  C1    0  -0.195  -4.1955  -1.8744   0.0661
 OCX  C18   C  C1    0  -0.206  -5.0380  -1.1299  -0.6419
 OCX  C19   C  CH2   0  -0.484  -6.3313  -0.5800  -0.1309
 OCX  C20   C  CH2   0  -0.420  -6.3678   0.9474  -0.1801
 OCX  C21   C  CH2   0  -0.580  -7.7090   1.4852   0.2906
 OCX  C22   C  C     0   0.550  -7.8154   2.9835   0.2344
 OCX  O23   O  OH1   0  -0.598  -9.0091   3.4092   0.6394
 OCX  O24   O  O     0  -0.445  -6.9423   3.7312  -0.1303
 OCX  H1    H  HCH3  0   0.216  10.1038   4.1576  -0.3240
 OCX  H1A   H  HCH3  0   0.216   8.6034   4.8177  -0.9666
 OCX  H1B   H  HCH3  0   0.226   9.1839   5.3285   0.6168
 OCX  H2    H  HCH2  0   0.211   8.8136   3.0193   1.5087
 OCX  H2A   H  HCH2  0   0.211   7.3236   3.6895   0.8847
 OCX  H3    H  HCH2  0   0.209   7.6723   2.4484  -1.2666
 OCX  H3A   H  HCH2  0   0.209   9.1540   1.7689  -0.6280
 OCX  H4    H  HCH2  0   0.214   7.8495   0.6773   1.2158
 OCX  H4A   H  HCH2  0   0.216   6.3699   1.3482   0.5612
 OCX  H5    H  HCH2  0   0.228   6.7562   0.0993  -1.5857
 OCX  H5A   H  HCH2  0   0.228   8.2350  -0.5639  -0.9133
 OCX  H6    H  H     0   0.232   6.8544  -1.7318   0.8975
 OCX  H7    H  H     0   0.239   4.9245  -1.4415  -1.4522
 OCX  H8    H  HCH2  0   0.256   4.4135  -3.7745  -0.5913
 OCX  H8A   H  HCH2  0   0.259   5.0736  -3.3298   0.9823
 OCX  H9    H  H     0   0.262   3.1907  -1.6966   1.3262
 OCX  H10   H  H     0   0.255   2.0222  -3.5296  -0.8301
 OCX  H11   H  H     0   0.266   0.7886  -1.5099   1.1886
 OCX  H13   H  H     0   0.261  -0.4634  -3.2898  -0.9710
 OCX  H16   H  HCH2  0   0.286  -2.7835  -2.1831  -1.5223
 OCX  H16A  H  HCH2  0   0.278  -2.9228  -3.5273  -0.4265
 OCX  H17   H  H     0   0.239  -4.4447  -2.1248   1.0938
 OCX  H18   H  H     0   0.235  -4.7856  -0.8791  -1.6708
 OCX  H19   H  HCH2  0   0.233  -7.1564  -0.9709  -0.7370
 OCX  H19A  H  HCH2  0   0.234  -6.5054  -0.9267   0.8920
 OCX  H20   H  HCH2  0   0.234  -5.5630   1.3492   0.4396
 OCX  H20A  H  HCH2  0   0.231  -6.1723   1.2815  -1.2023
 OCX  H21   H  HCH2  0   0.277  -8.5220   1.0636  -0.3093
 OCX  H21A  H  HCH2  0   0.278  -7.9128   1.1678   1.3184
 OCX  H30   H  HOH1  0   0.478  -9.0514   4.3757   0.5879

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
 OCX  C1   C2    single  1.523  0.020  1.523
 OCX  C1   H1    single  0.970  0.020  1.090
 OCX  C1   H1A   single  0.970  0.020  1.090
 OCX  C1   H1B   single  0.970  0.020  1.090
 OCX  C2   C3    single  1.524  0.020  1.524
 OCX  C2   H2    single  0.970  0.020  1.090
 OCX  C2   H2A   single  0.970  0.020  1.090
 OCX  C3   C4    single  1.523  0.020  1.523
 OCX  C3   H3    single  0.970  0.020  1.090
 OCX  C3   H3A   single  0.970  0.020  1.090
 OCX  C4   C5    single  1.529  0.020  1.529
 OCX  C4   H4    single  0.970  0.020  1.090
 OCX  C4   H4A   single  0.970  0.020  1.090
 OCX  C5   C6    single  1.495  0.020  1.495
 OCX  C5   H5    single  0.970  0.020  1.090
 OCX  C5   H5A   single  0.970  0.020  1.090
 OCX  C6   C7    double  1.330  0.020  1.330
 OCX  C6   H6    single  0.930  0.020  1.080
 OCX  C7   C8    single  1.503  0.020  1.503
 OCX  C7   H7    single  0.930  0.020  1.080
 OCX  C8   C9    single  1.495  0.020  1.495
 OCX  C8   H8    single  0.970  0.020  1.090
 OCX  C8   H8A   single  0.970  0.020  1.090
 OCX  C9   C10   double  1.339  0.020  1.339
 OCX  C9   H9    single  0.930  0.020  1.080
 OCX  C10  C11   single  1.444  0.020  1.444
 OCX  C10  H10   single  0.930  0.020  1.080
 OCX  C11  C13   double  1.343  0.020  1.343
 OCX  C11  H11   single  0.930  0.020  1.080
 OCX  C13  C14   single  1.471  0.020  1.471
 OCX  C13  H13   single  0.930  0.020  1.080
 OCX  C14  O15   double  1.216  0.020  1.216
 OCX  C14  C16   single  1.513  0.020  1.513
 OCX  C16  C17   single  1.492  0.020  1.492
 OCX  C16  H16   single  0.970  0.020  1.090
 OCX  C16  H16A  single  0.970  0.020  1.090
 OCX  C17  C18   double  1.329  0.020  1.329
 OCX  C17  H17   single  0.930  0.020  1.080
 OCX  C18  C19   single  1.495  0.020  1.495
 OCX  C18  H18   single  0.930  0.020  1.080
 OCX  C19  C20   single  1.529  0.020  1.529
 OCX  C19  H19   single  0.970  0.020  1.090
 OCX  C19  H19A  single  0.970  0.020  1.090
 OCX  C20  C21   single  1.520  0.020  1.520
 OCX  C20  H20   single  0.970  0.020  1.090
 OCX  C20  H20A  single  0.970  0.020  1.090
 OCX  C21  C22   single  1.503  0.020  1.503
 OCX  C21  H21   single  0.970  0.020  1.090
 OCX  C21  H21A  single  0.970  0.020  1.090
 OCX  C22  O23   single  1.330  0.020  1.330
 OCX  C22  O24   double  1.206  0.020  1.206
 OCX  O23  H30   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
 OCX  H1B   C1   H1A  107.71  3.000
 OCX  H1B   C1   H1   107.64  3.000
 OCX  H1A   C1   H1   107.50  3.000
 OCX  H1B   C1   C2   111.70  3.000
 OCX  H1A   C1   C2   110.94  3.000
 OCX  H1    C1   C2   111.15  3.000
 OCX  H2A   C2   H2   106.07  3.000
 OCX  H2A   C2   C3   109.31  3.000
 OCX  H2    C2   C3   109.32  3.000
 OCX  H2A   C2   C1   109.58  3.000
 OCX  H2    C2   C1   109.65  3.000
 OCX  C3    C2   C1   112.70  3.000
 OCX  H3A   C3   H3   106.04  3.000
 OCX  H3A   C3   C4   109.36  3.000
 OCX  H3    C3   C4   109.21  3.000
 OCX  H3A   C3   C2   109.35  3.000
 OCX  H3    C3   C2   109.39  3.000
 OCX  C4    C3   C2   113.24  3.000
 OCX  H4A   C4   H4   106.22  3.000
 OCX  H4A   C4   C5   109.27  3.000
 OCX  H4    C4   C5   109.47  3.000
 OCX  H4A   C4   C3   109.55  3.000
 OCX  H4    C4   C3   109.45  3.000
 OCX  C5    C4   C3   112.68  3.000
 OCX  H5A   C5   H5   106.51  3.000
 OCX  H5A   C5   C6   109.43  3.000
 OCX  H5    C5   C6   109.88  3.000
 OCX  H5A   C5   C4   108.59  3.000
 OCX  H5    C5   C4   109.77  3.000
 OCX  C6    C5   C4   112.47  3.000
 OCX  H6    C6   C7   118.97  3.000
 OCX  H6    C6   C5   116.07  3.000
 OCX  C7    C6   C5   124.95  3.000
 OCX  H7    C7   C8   115.61  3.000
 OCX  H7    C7   C6   119.43  3.000
 OCX  C8    C7   C6   124.96  3.000
 OCX  H8A   C8   H8   107.47  3.000
 OCX  H8A   C8   C9   109.71  3.000
 OCX  H8    C8   C9   109.74  3.000
 OCX  H8A   C8   C7   109.58  3.000
 OCX  H8    C8   C7   110.09  3.000
 OCX  C9    C8   C7   110.20  3.000
 OCX  H9    C9   C10  119.08  3.000
 OCX  H9    C9   C8   116.08  3.000
 OCX  C10   C9   C8   124.80  3.000
 OCX  H10   C10  C11  117.63  3.000
 OCX  H10   C10  C9   119.78  3.000
 OCX  C11   C10  C9   122.59  3.000
 OCX  H11   C11  C13  118.97  3.000
 OCX  H11   C11  C10  116.87  3.000
 OCX  C13   C11  C10  124.16  3.000
 OCX  H13   C13  C14  117.40  3.000
 OCX  H13   C13  C11  120.24  3.000
 OCX  C14   C13  C11  122.36  3.000
 OCX  C16   C14  O15  121.95  3.000
 OCX  C16   C14  C13  115.27  3.000
 OCX  O15   C14  C13  122.78  3.000
 OCX  H16A  C16  H16  105.01  3.000
 OCX  H16A  C16  C17  110.82  3.000
 OCX  H16   C16  C17  111.23  3.000
 OCX  H16A  C16  C14  107.26  3.000
 OCX  H16   C16  C14  107.89  3.000
 OCX  C17   C16  C14  114.15  3.000
 OCX  H17   C17  C18  119.19  3.000
 OCX  H17   C17  C16  116.49  3.000
 OCX  C18   C17  C16  124.31  3.000
 OCX  H18   C18  C19  116.03  3.000
 OCX  H18   C18  C17  119.06  3.000
 OCX  C19   C18  C17  124.91  3.000
 OCX  H19A  C19  H19  106.51  3.000
 OCX  H19A  C19  C20  110.06  3.000
 OCX  H19   C19  C20  108.70  3.000
 OCX  H19A  C19  C18  109.92  3.000
 OCX  H19   C19  C18  109.33  3.000
 OCX  C20   C19  C18  112.15  3.000
 OCX  H20A  C20  H20  106.64  3.000
 OCX  H20A  C20  C21  109.84  3.000
 OCX  H20   C20  C21  110.14  3.000
 OCX  H20A  C20  C19  109.34  3.000
 OCX  H20   C20  C19  109.37  3.000
 OCX  C21   C20  C19  111.39  3.000
 OCX  H21A  C21  H21  105.34  3.000
 OCX  H21A  C21  C22  108.12  3.000
 OCX  H21   C21  C22  108.10  3.000
 OCX  H21A  C21  C20  110.64  3.000
 OCX  H21   C21  C20  110.45  3.000
 OCX  C22   C21  C20  113.81  3.000
 OCX  O24   C22  O23  122.91  3.000
 OCX  O24   C22  C21  125.31  3.000
 OCX  O23   C22  C21  111.78  3.000
 OCX  H30   O23  C22  110.01  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
 OCX  CONST_01  H30  O23  C22  C21   180.00   0.0  0
 OCX  Var_01    C8   C7   C6   C5   -178.51   0.0  2
 OCX  Var_02    C11  C10  C9   C8   -177.76   0.0  2
 OCX  Var_03    C14  C13  C11  C10  -179.56   0.0  2
 OCX  Var_04    C19  C18  C17  C16   179.19   0.0  2
 OCX  Var_05    C4   C3   C2   C1   -179.23  30.0  3
 OCX  Var_06    C5   C4   C3   C2   -179.52  30.0  3
 OCX  Var_07    C6   C5   C4   C3    179.75  30.0  3
 OCX  Var_08    C7   C6   C5   C4    120.60  30.0  3
 OCX  Var_09    C9   C8   C7   C6    115.05  30.0  3
 OCX  Var_10    C10  C9   C8   C7    111.52  30.0  3
 OCX  Var_11    C13  C11  C10  C9    179.16  30.0  2
 OCX  Var_12    O15  C14  C13  C11    -0.66  30.0  2
 OCX  Var_13    C17  C16  C14  C13   176.26  30.0  3
 OCX  Var_14    C18  C17  C16  C14   119.85  30.0  3
 OCX  Var_15    C20  C19  C18  C17   119.70  30.0  3
 OCX  Var_16    C21  C20  C19  C18   177.73  30.0  3
 OCX  Var_17    C22  C21  C20  C19  -178.68  30.0  3
 OCX  Var_18    O23  C22  C21  C20   179.25  30.0  3
 OCX  Var_19    H1   C1   C2   C3    -60.43  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
 OCX  plan-1  C13  0.020
 OCX  plan-1  C14  0.020
 OCX  plan-1  O15  0.020
 OCX  plan-1  C16  0.020
 OCX  plan-2  C21  0.020
 OCX  plan-2  C22  0.020
 OCX  plan-2  O23  0.020
 OCX  plan-2  O24  0.020
 OCX  plan-2  H30  0.020
 OCX  plan-3  C5   0.020
 OCX  plan-3  C6   0.020
 OCX  plan-3  C7   0.020
 OCX  plan-3  C8   0.020
 OCX  plan-3  H6   0.020
 OCX  plan-3  H7   0.020
 OCX  plan-4  C8   0.020
 OCX  plan-4  C9   0.020
 OCX  plan-4  C10  0.020
 OCX  plan-4  C11  0.020
 OCX  plan-4  H9   0.020
 OCX  plan-4  H10  0.020
 OCX  plan-5  C10  0.020
 OCX  plan-5  C11  0.020
 OCX  plan-5  C13  0.020
 OCX  plan-5  C14  0.020
 OCX  plan-5  H11  0.020
 OCX  plan-5  H13  0.020
 OCX  plan-6  C16  0.020
 OCX  plan-6  C17  0.020
 OCX  plan-6  C18  0.020
 OCX  plan-6  C19  0.020
 OCX  plan-6  H17  0.020
 OCX  plan-6  H18  0.020

