# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr 26 17:49:27 2020
#   Inital geometry file: a 114 line input string
#   Ligand name: (4Z,6R,7S,8S,9E)-7-hydroxy-8-methoxy-4,6-dimethylcyclotetradeca-4,9-dien-1-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CO[C@H]1\C=C\CCCCC(=O)CCC(=C\[C@@H](C)[C@@H]1O)/C
#
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
 O8K  O8K  (4Z,6R,7S,8S,9E)-7-hydroxy-8-methoxy-4,6-dimethylcyclotetradeca-4,9-dien-1-one  ligand  48  20  .  2021-08-17  2021-08-17  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_O8K
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
 O8K  C1    C  CH3   0  -0.717  -0.9485   3.0123   1.7434
 O8K  C2    C  C     0   0.101  -0.5837   2.1997   0.5335
 O8K  C3    C  C1    0  -0.220   0.6942   1.9508   0.2380
 O8K  C4    C  CH1   0  -0.333   1.2318   1.2681  -0.9921
 O8K  C5    C  CH3   0  -0.641   1.2721   2.2949  -2.1333
 O8K  C6    C  CH1   0   0.055   2.6246   0.6782  -0.7376
 O8K  O7    O  OH1   0  -0.670   3.1819   0.3251  -1.9855
 O8K  C8    C  CH1   0   0.006   2.6544  -0.5677   0.1775
 O8K  O9    O  O2    0  -0.484   2.2965  -0.2029   1.4832
 O8K  C10   C  CH3   0  -0.408   2.9913  -0.9059   2.4857
 O8K  C11   C  C1    0  -0.255   1.8193  -1.6847  -0.3806
 O8K  C12   C  C1    0  -0.204   0.8707  -2.3551   0.2632
 O8K  C13   C  CH2   0  -0.480   0.0215  -3.4264  -0.3500
 O8K  C14   C  CH2   0  -0.427  -1.4694  -3.1642  -0.1187
 O8K  C15   C  CH2   0  -0.449  -1.8966  -1.7854  -0.6022
 O8K  C16   C  CH2   0  -0.559  -3.3508  -1.4456  -0.2579
 O8K  C17   C  C     0   0.419  -3.6079   0.0356  -0.3634
 O8K  O18   O  O     0  -0.408  -4.4198   0.5116  -1.1273
 O8K  C19   C  CH2   0  -0.576  -2.7565   0.9115   0.5287
 O8K  C20   C  CH2   0  -0.511  -1.7439   1.7305  -0.2990
 O8K  H1    H  HCH3  0   0.238  -0.0639   3.3946   2.2523
 O8K  H1A   H  HCH3  0   0.230  -1.5741   3.8655   1.4671
 O8K  H1B   H  HCH3  0   0.236  -1.5220   2.4303   2.4693
 O8K  H3    H  H     0   0.213   1.4439   2.3756   0.9007
 O8K  H4    H  HCH1  0   0.241   0.5679   0.4490  -1.2904
 O8K  H5    H  HCH3  0   0.215   1.9651   3.1073  -1.9029
 O8K  H5A   H  HCH3  0   0.230   1.5739   1.8516  -3.0808
 O8K  H5B   H  HCH3  0   0.228   0.2848   2.7364  -2.2701
 O8K  H6    H  HCH1  0   0.210   3.2404   1.4517  -0.2515
 O8K  HO7   H  HOH1  0   0.451   4.0986   0.0670  -1.8471
 O8K  H8    H  HCH1  0   0.215   3.7081  -0.9015   0.1687
 O8K  H10   H  HCH3  0   0.206   2.8272  -1.9869   2.4341
 O8K  H10A  H  HCH3  0   0.210   4.0712  -0.7253   2.4349
 O8K  H10B  H  HCH3  0   0.232   2.6290  -0.5522   3.4504
 O8K  H11   H  H     0   0.235   2.0299  -1.9374  -1.4164
 O8K  H12   H  H     0   0.235   0.6432  -2.1094   1.2981
 O8K  H13   H  HCH2  0   0.227   0.2313  -3.5004  -1.4209
 O8K  H13A  H  HCH2  0   0.239   0.2738  -4.3987   0.0858
 O8K  H14   H  HCH2  0   0.232  -2.0597  -3.9423  -0.6099
 O8K  H14A  H  HCH2  0   0.217  -1.6820  -3.2457   0.9525
 O8K  H15   H  HCH2  0   0.250  -1.2303  -1.0487  -0.1467
 O8K  H15A  H  HCH2  0   0.232  -1.7453  -1.7015  -1.6825
 O8K  H16   H  HCH2  0   0.254  -4.0471  -2.0003  -0.8885
 O8K  H16A  H  HCH2  0   0.254  -3.5409  -1.7328   0.7829
 O8K  H19   H  HCH2  0   0.278  -3.4119   1.5810   1.0902
 O8K  H19A  H  HCH2  0   0.253  -2.2281   0.2964   1.2593
 O8K  H20   H  HCH2  0   0.253  -2.2618   2.5942  -0.7269
 O8K  H20A  H  HCH2  0   0.248  -1.3939   1.1438  -1.1503

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
 O8K  C1   C2    single  1.502  0.020  1.502
 O8K  C2   C3    double  1.335  0.020  1.335
 O8K  C2   C20   single  1.503  0.020  1.503
 O8K  C3   C4    single  1.506  0.020  1.506
 O8K  C4   C5    single  1.536  0.020  1.536
 O8K  C4   C6    single  1.534  0.020  1.534
 O8K  C6   O7    single  1.412  0.020  1.412
 O8K  C6   C8    single  1.546  0.020  1.546
 O8K  C8   O9    single  1.402  0.020  1.402
 O8K  C8   C11   single  1.502  0.020  1.502
 O8K  O9   C10   single  1.408  0.020  1.408
 O8K  C11  C12   double  1.328  0.020  1.328
 O8K  C12  C13   single  1.498  0.020  1.498
 O8K  C13  C14   single  1.531  0.020  1.531
 O8K  C14  C15   single  1.522  0.020  1.522
 O8K  C15  C16   single  1.532  0.020  1.532
 O8K  C16  C17   single  1.507  0.020  1.507
 O8K  C17  O18   double  1.212  0.020  1.212
 O8K  C17  C19   single  1.513  0.020  1.513
 O8K  C19  C20   single  1.543  0.020  1.543
 O8K  C1   H1    single  0.970  0.020  1.090
 O8K  C1   H1A   single  0.970  0.020  1.090
 O8K  C1   H1B   single  0.970  0.020  1.090
 O8K  C3   H3    single  0.930  0.020  1.080
 O8K  C4   H4    single  0.970  0.020  1.090
 O8K  C5   H5    single  0.970  0.020  1.090
 O8K  C5   H5A   single  0.970  0.020  1.090
 O8K  C5   H5B   single  0.970  0.020  1.090
 O8K  C6   H6    single  0.970  0.020  1.090
 O8K  O7   HO7   single  0.850  0.020  0.980
 O8K  C8   H8    single  0.970  0.020  1.090
 O8K  C10  H10   single  0.970  0.020  1.090
 O8K  C10  H10A  single  0.970  0.020  1.090
 O8K  C10  H10B  single  0.970  0.020  1.090
 O8K  C11  H11   single  0.930  0.020  1.080
 O8K  C12  H12   single  0.930  0.020  1.080
 O8K  C13  H13   single  0.970  0.020  1.090
 O8K  C13  H13A  single  0.970  0.020  1.090
 O8K  C14  H14   single  0.970  0.020  1.090
 O8K  C14  H14A  single  0.970  0.020  1.090
 O8K  C15  H15   single  0.970  0.020  1.090
 O8K  C15  H15A  single  0.970  0.020  1.090
 O8K  C16  H16   single  0.970  0.020  1.090
 O8K  C16  H16A  single  0.970  0.020  1.090
 O8K  C19  H19   single  0.970  0.020  1.090
 O8K  C19  H19A  single  0.970  0.020  1.090
 O8K  C20  H20   single  0.970  0.020  1.090
 O8K  C20  H20A  single  0.970  0.020  1.090

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
 O8K  H1B   C1   H1A   106.45  3.000
 O8K  H1B   C1   H1    107.61  3.000
 O8K  H1A   C1   H1    107.98  3.000
 O8K  H1B   C1   C2    111.98  3.000
 O8K  H1A   C1   C2    110.95  3.000
 O8K  H1    C1   C2    111.63  3.000
 O8K  C20   C2   C3    123.92  3.000
 O8K  C20   C2   C1    115.30  3.000
 O8K  C3    C2   C1    120.77  3.000
 O8K  H3    C3   C4    115.39  3.000
 O8K  H3    C3   C2    116.89  3.000
 O8K  C4    C3   C2    127.37  3.000
 O8K  H4    C4   C6    107.93  3.000
 O8K  H4    C4   C5    108.26  3.000
 O8K  C6    C4   C5    110.90  3.000
 O8K  H4    C4   C3    110.17  3.000
 O8K  C6    C4   C3    111.28  3.000
 O8K  C5    C4   C3    108.26  3.000
 O8K  H5B   C5   H5A   107.86  3.000
 O8K  H5B   C5   H5    107.45  3.000
 O8K  H5A   C5   H5    108.09  3.000
 O8K  H5B   C5   C4    109.90  3.000
 O8K  H5A   C5   C4    112.44  3.000
 O8K  H5    C5   C4    110.93  3.000
 O8K  H6    C6   C8    107.09  3.000
 O8K  H6    C6   O7    110.18  3.000
 O8K  C8    C6   O7    108.31  3.000
 O8K  H6    C6   C4    108.10  3.000
 O8K  C8    C6   C4    115.19  3.000
 O8K  O7    C6   C4    107.94  3.000
 O8K  HO7   O7   C6    108.42  3.000
 O8K  H8    C8   C11   107.61  3.000
 O8K  H8    C8   O9    109.23  3.000
 O8K  C11   C8   O9    113.43  3.000
 O8K  H8    C8   C6    104.89  3.000
 O8K  C11   C8   C6    111.62  3.000
 O8K  O9    C8   C6    109.67  3.000
 O8K  C10   O9   C8    114.03  3.000
 O8K  H10B  C10  H10A  108.37  3.000
 O8K  H10B  C10  H10   108.21  3.000
 O8K  H10A  C10  H10   107.95  3.000
 O8K  H10B  C10  O9    107.72  3.000
 O8K  H10A  C10  O9    111.78  3.000
 O8K  H10   C10  O9    112.68  3.000
 O8K  H11   C11  C12   118.89  3.000
 O8K  H11   C11  C8    114.78  3.000
 O8K  C12   C11  C8    126.32  3.000
 O8K  H12   C12  C13   115.62  3.000
 O8K  H12   C12  C11   119.78  3.000
 O8K  C13   C12  C11   124.56  3.000
 O8K  H13A  C13  H13   106.59  3.000
 O8K  H13A  C13  C14   108.43  3.000
 O8K  H13   C13  C14   110.26  3.000
 O8K  H13A  C13  C12   109.96  3.000
 O8K  H13   C13  C12   109.90  3.000
 O8K  C14   C13  C12   111.57  3.000
 O8K  H14A  C14  H14   106.36  3.000
 O8K  H14A  C14  C15   108.88  3.000
 O8K  H14   C14  C15   110.52  3.000
 O8K  H14A  C14  C13   108.90  3.000
 O8K  H14   C14  C13   109.63  3.000
 O8K  C15   C14  C13   112.35  3.000
 O8K  H15A  C15  H15   105.99  3.000
 O8K  H15A  C15  C16   109.64  3.000
 O8K  H15   C15  C16   109.60  3.000
 O8K  H15A  C15  C14   110.13  3.000
 O8K  H15   C15  C14   107.89  3.000
 O8K  C16   C15  C14   113.31  3.000
 O8K  H16A  C16  H16   107.75  3.000
 O8K  H16A  C16  C17   107.12  3.000
 O8K  H16   C16  C17   110.51  3.000
 O8K  H16A  C16  C15   108.65  3.000
 O8K  H16   C16  C15   111.29  3.000
 O8K  C17   C16  C15   111.35  3.000
 O8K  C19   C17  O18   121.42  3.000
 O8K  C19   C17  C16   115.58  3.000
 O8K  O18   C17  C16   122.98  3.000
 O8K  H19A  C19  H19   106.97  3.000
 O8K  H19A  C19  C20   109.90  3.000
 O8K  H19   C19  C20   110.13  3.000
 O8K  H19A  C19  C17   109.93  3.000
 O8K  H19   C19  C17   108.69  3.000
 O8K  C20   C19  C17   111.12  3.000
 O8K  H20A  C20  H20   105.72  3.000
 O8K  H20A  C20  C19   110.08  3.000
 O8K  H20   C20  C19   108.54  3.000
 O8K  H20A  C20  C2    110.63  3.000
 O8K  H20   C20  C2    109.61  3.000
 O8K  C19   C20  C2    112.03  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
 O8K  Var_01  C20  C2   C3   C4      4.87   0.0  0
 O8K  Var_02  C13  C12  C11  C8    177.35   0.0  0
 O8K  Var_03  C17  C19  C20  C2   -158.90  30.0  1
 O8K  Var_04  C19  C20  C2   C3    124.76  30.0  1
 O8K  Var_05  C14  C13  C12  C11  -128.21  30.0  1
 O8K  Var_06  C15  C14  C13  C12    54.59  30.0  1
 O8K  Var_07  C16  C15  C14  C13  -174.33  30.0  1
 O8K  Var_08  C17  C16  C15  C14   162.61  30.0  1
 O8K  Var_09  C19  C17  C16  C15   -59.18  30.0  1
 O8K  Var_10  C20  C19  C17  C16   110.28  30.0  1
 O8K  Var_11  H12  C12  C11  C8     -0.23   0.0  0
 O8K  Var_12  H1   C1   C2   C3      3.99  30.0  3
 O8K  Var_13  H10  C10  O9   C8    -60.14  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
 O8K  chir_01  C4  C3  C5   C6  negativ
 O8K  chir_02  C6  O7  C4   C8  negativ
 O8K  chir_03  C8  O9  C11  C6  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
 O8K  plan-1  C16  0.020
 O8K  plan-1  C17  0.020
 O8K  plan-1  O18  0.020
 O8K  plan-1  C19  0.020
 O8K  plan-2  C1   0.020
 O8K  plan-2  C2   0.020
 O8K  plan-2  C3   0.020
 O8K  plan-2  C4   0.020
 O8K  plan-2  C20  0.020
 O8K  plan-2  H3   0.020
 O8K  plan-3  C8   0.020
 O8K  plan-3  C11  0.020
 O8K  plan-3  C12  0.020
 O8K  plan-3  C13  0.020
 O8K  plan-3  H11  0.020
 O8K  plan-3  H12  0.020

