# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version 1.18.1-3865-
#   - file written: Sun Jun 14 20:01:35 2020
#   Inital geometry file: a 151 line input string
#   Ligand name: (1~{S},2~{S},4~{R},6~{R},8~{S},9~{S},11~{S},12~{S},13~{R})-9,13-dimethyl-11-oxidanyl-8-(2-oxidanylethanoyl)-6-propyl-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-16-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCC[C@@H]1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@@]2(O1)C(=O)CO
#
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
 8W5  8W5  (1~{S},2~{S},4~{R},6~{R},8~{S},9~{S},11~{S},12~{S},13~{R})-9,13-dimethyl-11-oxidanyl-8-(2-oxidanylethanoyl)-6-propyl-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-16-one  ligand  65  31  .  2021-08-06  2021-08-06  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_8W5
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
 8W5  C1   C  CH3   0  -0.663  -4.2307   4.9718  -0.9432
 8W5  C2   C  CH2   0  -0.432  -4.3090   3.6739  -0.1522
 8W5  C3   C  CH2   0  -0.480  -3.4247   2.5871  -0.7538
 8W5  C7   C  CR15  0   0.059  -2.6388   0.0746   1.6790
 8W5  C9   C  CH2   0  -0.473  -1.2253   0.2048   2.2530
 8W5  C10  C  CH1   0  -0.196  -0.3391  -0.0120   1.0340
 8W5  C12  C  CH1   0  -0.244   1.1621  -0.1932   1.2127
 8W5  C14  C  CH2   0  -0.420   1.7412   1.0146   1.9461
 8W5  C15  C  CH2   0  -0.506   3.2688   1.0194   1.9667
 8W5  C16  C  C     0   0.244   3.7905   0.8642   0.5771
 8W5  C20  C  C1    0  -0.387   4.6531   0.4860  -2.0997
 8W5  C21  C  C1    0  -0.124   3.8972  -0.4549  -1.5321
 8W5  C22  C  CT    0  -0.212   3.3577  -0.3880  -0.1396
 8W5  C27  C  CH2   0  -0.468  -0.3952  -1.2934  -1.0869
 8W5  C4   C  CR15  0   0.326  -3.5557   1.2617  -0.0450
 8W5  O6   O  O     0  -0.505  -3.1253   1.3460   1.2835
 8W5  C17  C  C1    0  -0.469   4.5476   1.8074  -0.0013
 8W5  C18  C  C     0   0.395   5.0257   1.7043  -1.3764
 8W5  O19  O  O     0  -0.456   5.7042   2.5808  -1.8968
 8W5  C23  C  CH1   0  -0.215   1.7890  -0.3358  -0.1890
 8W5  C25  C  CH1   0   0.053   1.1350  -1.4211  -1.0578
 8W5  C28  C  CT    0  -0.082  -1.0183  -1.1795   0.3005
 8W5  C29  C  CR5   0   0.080  -2.5025  -0.6998   0.3298
 8W5  O30  O  O     0  -0.504  -2.7191   0.3006  -0.6393
 8W5  O34  O  OH1   0  -0.657  -4.6859  -3.2829  -1.3151
 8W5  O36  O  OH1   0  -0.656   1.5645  -2.6944  -0.6306
 8W5  C37  C  CH3   0  -0.656   3.9463  -1.5973   0.6237
 8W5  H1   H  HCH3  0   0.220  -3.2100   5.3577  -0.9680
 8W5  H2   H  HCH3  0   0.219  -4.5524   4.8250  -1.9758
 8W5  H3   H  HCH3  0   0.231  -4.8647   5.7430  -0.5053
 8W5  H4   H  HCH2  0   0.226  -4.0160   3.8592   0.8837
 8W5  H5   H  HCH2  0   0.220  -5.3460   3.3262  -0.1227
 8W5  H6   H  HCH2  0   0.237  -3.6999   2.4355  -1.8017
 8W5  H7   H  HCH2  0   0.231  -2.3753   2.8972  -0.7383
 8W5  H8   H  HCR5  0   0.248  -3.3351  -0.4009   2.3742
 8W5  H9   H  HCH2  0   0.259  -1.0902   1.1755   2.7309
 8W5  H10  H  HCH2  0   0.240  -1.0496  -0.5574   3.0146
 8W5  H11  H  HCH1  0   0.235  -0.4512   0.8748   0.3942
 8W5  H12  H  HCH1  0   0.234   1.3636  -1.0885   1.8100
 8W5  H13  H  HCH2  0   0.224   1.3911   1.9317   1.4594
 8W5  H14  H  HCH2  0   0.251   1.3708   1.0424   2.9727
 8W5  H15  H  HCH2  0   0.259   3.6388   1.9450   2.4102
 8W5  H16  H  HCH2  0   0.255   3.6281   0.1992   2.5956
 8W5  H17  H  H     0   0.261   5.0225   0.3667  -3.1113
 8W5  H18  H  H     0   0.283   3.6710  -1.3558  -2.0915
 8W5  H19  H  HCH2  0   0.247  -0.6344  -0.4011  -1.6699
 8W5  H20  H  HCH2  0   0.241  -0.8011  -2.1440  -1.6461
 8W5  H21  H  HCH2  0   0.249  -4.4943  -1.2397  -1.6618
 8W5  H22  H  HCH2  0   0.237  -3.0289  -2.1644  -1.9101
 8W5  H26  H  HCR5  0   0.196  -4.6048   0.9144  -0.0817
 8W5  H27  H  H     0   0.250   4.8311   2.6969   0.5520
 8W5  H28  H  HCH1  0   0.244   1.5563   0.6012  -0.7150
 8W5  H29  H  HCH1  0   0.224   1.4635  -1.2511  -2.0927
 8W5  H30  H  HOH1  0   0.463  -5.0453  -3.3807  -2.2013
 8W5  H31  H  HOH1  0   0.450   1.1188  -3.3584  -1.1663
 8W5  H32  H  HCH3  0   0.243   3.4299  -1.7887   1.5627
 8W5  H33  H  HCH3  0   0.256   3.8912  -2.5029   0.0273
 8W5  H34  H  HCH3  0   0.237   4.9963  -1.4082   0.8522
 8W5  C31  C  C     0   0.363  -3.5267  -1.8147   0.1371
 8W5  C35  C  CH3   0  -0.694  -0.9130  -2.4940   1.0862
 8W5  O32  O  O     0  -0.376  -3.9817  -2.4365   1.0648
 8W5  C33  C  CH2   0  -0.246  -3.9339  -2.1077  -1.2880
 8W5  H23  H  HCH3  0   0.236  -1.5049  -2.4835   2.0011
 8W5  H24  H  HCH3  0   0.235  -1.2661  -3.3366   0.4886
 8W5  H25  H  HCH3  0   0.261   0.1125  -2.7132   1.3664

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
 8W5  O19  C18  double  1.225  0.020  1.225
 8W5  C18  C20  single  1.465  0.020  1.465
 8W5  C18  C17  single  1.460  0.020  1.460
 8W5  C20  C21  double  1.334  0.020  1.334
 8W5  C17  C16  double  1.341  0.020  1.341
 8W5  C21  C22  single  1.495  0.020  1.495
 8W5  C16  C15  single  1.492  0.020  1.492
 8W5  C16  C22  single  1.506  0.020  1.506
 8W5  C37  C22  single  1.546  0.020  1.546
 8W5  C15  C14  single  1.528  0.020  1.528
 8W5  C22  C23  single  1.570  0.020  1.570
 8W5  C23  C12  single  1.542  0.020  1.542
 8W5  C23  C25  single  1.536  0.020  1.536
 8W5  C14  C12  single  1.527  0.020  1.527
 8W5  O36  C25  single  1.410  0.020  1.410
 8W5  C12  C10  single  1.523  0.020  1.523
 8W5  C25  C27  single  1.536  0.020  1.536
 8W5  C10  C28  single  1.537  0.020  1.537
 8W5  C10  C9   single  1.523  0.020  1.523
 8W5  C27  C28  single  1.525  0.020  1.525
 8W5  C28  C35  single  1.535  0.020  1.535
 8W5  C28  C29  single  1.560  0.020  1.560
 8W5  C9   C7   single  1.531  0.020  1.531
 8W5  C1   C2   single  1.522  0.020  1.522
 8W5  C3   C2   single  1.525  0.020  1.525
 8W5  C3   C4   single  1.509  0.020  1.509
 8W5  C29  O30  single  1.410  0.020  1.410
 8W5  C29  C7   single  1.562  0.020  1.562
 8W5  C29  C31  single  1.526  0.020  1.526
 8W5  O30  C4   single  1.406  0.020  1.406
 8W5  C7   O6   single  1.418  0.020  1.418
 8W5  O6   C4   single  1.399  0.020  1.399
 8W5  C31  C33  single  1.511  0.020  1.511
 8W5  C31  O32  double  1.206  0.020  1.206
 8W5  C33  O34  single  1.395  0.020  1.395
 8W5  C1   H1   single  0.970  0.020  1.090
 8W5  C1   H2   single  0.970  0.020  1.090
 8W5  C1   H3   single  0.970  0.020  1.090
 8W5  C2   H4   single  0.970  0.020  1.090
 8W5  C2   H5   single  0.970  0.020  1.090
 8W5  C3   H6   single  0.970  0.020  1.090
 8W5  C3   H7   single  0.970  0.020  1.090
 8W5  C7   H8   single  0.970  0.020  1.090
 8W5  C9   H9   single  0.970  0.020  1.090
 8W5  C9   H10  single  0.970  0.020  1.090
 8W5  C10  H11  single  0.970  0.020  1.090
 8W5  C12  H12  single  0.970  0.020  1.090
 8W5  C14  H13  single  0.970  0.020  1.090
 8W5  C14  H14  single  0.970  0.020  1.090
 8W5  C15  H15  single  0.970  0.020  1.090
 8W5  C15  H16  single  0.970  0.020  1.090
 8W5  C20  H17  single  0.930  0.020  1.080
 8W5  C21  H18  single  0.930  0.020  1.080
 8W5  C27  H19  single  0.970  0.020  1.090
 8W5  C27  H20  single  0.970  0.020  1.090
 8W5  C33  H21  single  0.970  0.020  1.090
 8W5  C33  H22  single  0.970  0.020  1.090
 8W5  C35  H23  single  0.970  0.020  1.090
 8W5  C35  H24  single  0.970  0.020  1.090
 8W5  C35  H25  single  0.970  0.020  1.090
 8W5  C4   H26  single  0.970  0.020  1.090
 8W5  C17  H27  single  0.930  0.020  1.080
 8W5  C23  H28  single  0.970  0.020  1.090
 8W5  C25  H29  single  0.970  0.020  1.090
 8W5  O34  H30  single  0.850  0.020  0.980
 8W5  O36  H31  single  0.850  0.020  0.980
 8W5  C37  H32  single  0.970  0.020  1.090
 8W5  C37  H33  single  0.970  0.020  1.090
 8W5  C37  H34  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
 8W5  H3   C1   H2   107.68  3.000
 8W5  H3   C1   H1   107.63  3.000
 8W5  H2   C1   H1   107.56  3.000
 8W5  H3   C1   C2   111.38  3.000
 8W5  H2   C1   C2   111.21  3.000
 8W5  H1   C1   C2   111.19  3.000
 8W5  H5   C2   H4   106.42  3.000
 8W5  H5   C2   C3   109.50  3.000
 8W5  H4   C2   C3   109.85  3.000
 8W5  H5   C2   C1   109.50  3.000
 8W5  H4   C2   C1   109.53  3.000
 8W5  C3   C2   C1   111.89  3.000
 8W5  H7   C3   H6   107.10  3.000
 8W5  H7   C3   C4   109.00  3.000
 8W5  H6   C3   C4   107.85  3.000
 8W5  H7   C3   C2   110.40  3.000
 8W5  H6   C3   C2   109.32  3.000
 8W5  C4   C3   C2   112.98  3.000
 8W5  H8   C7   C29  112.93  3.000
 8W5  H8   C7   O6   110.43  3.000
 8W5  C29  C7   O6   103.51  3.000
 8W5  H8   C7   C9   112.75  3.000
 8W5  O6   C7   C9   110.19  3.000
 8W5  C29  C7   C9   106.59  3.000
 8W5  H10  C9   H9   107.20  3.000
 8W5  H10  C9   C10  111.44  3.000
 8W5  H9   C9   C10  113.92  3.000
 8W5  H10  C9   C7   110.53  3.000
 8W5  H9   C9   C7   110.76  3.000
 8W5  C10  C9   C7   103.01  3.000
 8W5  H11  C10  C28  106.85  3.000
 8W5  H11  C10  C12  105.36  3.000
 8W5  C28  C10  C12  113.66  3.000
 8W5  H11  C10  C9   106.97  3.000
 8W5  C28  C10  C9   103.47  3.000
 8W5  C12  C10  C9   119.79  3.000
 8W5  H12  C12  C23  110.21  3.000
 8W5  H12  C12  C14  108.36  3.000
 8W5  C23  C12  C14  110.82  3.000
 8W5  H12  C12  C10  110.05  3.000
 8W5  C14  C12  C10  109.64  3.000
 8W5  C23  C12  C10  107.77  3.000
 8W5  H14  C14  H13  106.74  3.000
 8W5  H14  C14  C15  109.06  3.000
 8W5  H13  C14  C15  108.83  3.000
 8W5  H14  C14  C12  110.06  3.000
 8W5  H13  C14  C12  109.12  3.000
 8W5  C15  C14  C12  112.84  3.000
 8W5  H16  C15  H15  106.91  3.000
 8W5  H16  C15  C16  110.02  3.000
 8W5  H15  C15  C16  110.37  3.000
 8W5  H16  C15  C14  109.49  3.000
 8W5  H15  C15  C14  110.32  3.000
 8W5  C16  C15  C14  109.68  3.000
 8W5  C17  C16  C22  122.81  3.000
 8W5  C22  C16  C15  115.40  3.000
 8W5  C17  C16  C15  121.73  3.000
 8W5  H17  C20  C18  117.77  3.000
 8W5  H17  C20  C21  120.85  3.000
 8W5  C18  C20  C21  121.38  3.000
 8W5  H18  C21  C22  116.26  3.000
 8W5  H18  C21  C20  119.00  3.000
 8W5  C22  C21  C20  124.71  3.000
 8W5  C37  C22  C23  114.94  3.000
 8W5  C23  C22  C21  109.43  3.000
 8W5  C37  C22  C21  106.70  3.000
 8W5  C23  C22  C16  105.93  3.000
 8W5  C37  C22  C16  107.81  3.000
 8W5  C21  C22  C16  112.13  3.000
 8W5  H20  C27  H19  106.30  3.000
 8W5  H20  C27  C28  111.77  3.000
 8W5  H19  C27  C28  109.58  3.000
 8W5  H20  C27  C25  108.30  3.000
 8W5  H19  C27  C25  107.23  3.000
 8W5  C28  C27  C25  113.33  3.000
 8W5  H26  C4   O30  109.62  3.000
 8W5  H26  C4   O6   110.02  3.000
 8W5  O30  C4   O6   105.04  3.000
 8W5  H26  C4   C3   110.04  3.000
 8W5  O6   C4   C3   111.50  3.000
 8W5  O30  C4   C3   110.50  3.000
 8W5  C4   O6   C7   108.45  3.000
 8W5  H27  C17  C18  116.91  3.000
 8W5  H27  C17  C16  120.28  3.000
 8W5  C18  C17  C16  122.81  3.000
 8W5  O19  C18  C17  122.10  3.000
 8W5  C17  C18  C20  116.14  3.000
 8W5  O19  C18  C20  121.76  3.000
 8W5  H28  C23  C25  103.97  3.000
 8W5  H28  C23  C22  104.76  3.000
 8W5  C25  C23  C22  114.81  3.000
 8W5  H28  C23  C12  105.66  3.000
 8W5  C25  C23  C12  113.97  3.000
 8W5  C22  C23  C12  112.37  3.000
 8W5  H29  C25  O36  109.51  3.000
 8W5  H29  C25  C23  107.21  3.000
 8W5  O36  C25  C23  109.69  3.000
 8W5  H29  C25  C27  105.49  3.000
 8W5  O36  C25  C27  112.61  3.000
 8W5  C23  C25  C27  112.09  3.000
 8W5  C29  C28  C35  108.60  3.000
 8W5  C29  C28  C27  115.39  3.000
 8W5  C35  C28  C27  111.94  3.000
 8W5  C29  C28  C10  100.24  3.000
 8W5  C35  C28  C10  112.08  3.000
 8W5  C27  C28  C10  108.08  3.000
 8W5  O30  C29  C28  110.58  3.000
 8W5  O30  C29  C31  109.18  3.000
 8W5  C28  C29  C31  114.29  3.000
 8W5  C31  C29  C7   114.38  3.000
 8W5  O30  C29  C7   103.22  3.000
 8W5  C28  C29  C7   104.58  3.000
 8W5  C29  O30  C4   106.62  3.000
 8W5  H30  O34  C33  107.76  3.000
 8W5  H31  O36  C25  108.25  3.000
 8W5  H34  C37  H33  107.97  3.000
 8W5  H34  C37  H32  107.84  3.000
 8W5  H33  C37  H32  107.64  3.000
 8W5  H34  C37  C22  109.51  3.000
 8W5  H33  C37  C22  111.22  3.000
 8W5  H32  C37  C22  112.50  3.000
 8W5  O32  C31  C29  122.19  3.000
 8W5  O32  C31  C33  121.59  3.000
 8W5  C29  C31  C33  116.21  3.000
 8W5  H25  C35  H24  106.92  3.000
 8W5  H25  C35  H23  107.36  3.000
 8W5  H24  C35  H23  106.94  3.000
 8W5  H25  C35  C28  111.71  3.000
 8W5  H24  C35  C28  111.01  3.000
 8W5  H23  C35  C28  112.59  3.000
 8W5  H22  C33  H21  105.55  3.000
 8W5  H22  C33  O34  112.90  3.000
 8W5  H21  C33  O34  112.57  3.000
 8W5  H22  C33  C31  108.77  3.000
 8W5  H21  C33  C31  107.76  3.000
 8W5  O34  C33  C31  109.08  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
 8W5  Var_01  C16  C15  C14  C12    52.56  30.0  1
 8W5  Var_02  C17  C16  C15  C14   118.65  30.0  1
 8W5  Var_03  C18  C17  C16  C15  -177.49  30.0  1
 8W5  Var_04  C20  C18  C17  C16    -1.15  30.0  1
 8W5  Var_05  C17  C18  C20  C21     1.31  30.0  1
 8W5  Var_06  C18  C20  C21  C22    -0.08  30.0  1
 8W5  Var_07  C4   C3   C2   C1   -176.06  30.0  1
 8W5  Var_08  O34  C33  C31  C29   169.97  30.0  3
 8W5  Var_09  H1   C1   C2   C3    -59.88  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
 8W5  chir_01  C7   C9   C29  O6   positiv
 8W5  chir_02  C10  C9   C28  C12  positiv
 8W5  chir_03  C12  C10  C14  C23  positiv
 8W5  chir_04  C22  C16  C21  C23  positiv
 8W5  chir_05  C4   C3   O30  O6   negativ
 8W5  chir_06  C23  C22  C12  C25  positiv
 8W5  chir_07  C25  O36  C23  C27  positiv
 8W5  chir_08  C28  C29  C27  C10  negativ
 8W5  chir_09  C29  C28  C7   O30  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
 8W5  plan-1  C20  0.020
 8W5  plan-1  C17  0.020
 8W5  plan-1  C18  0.020
 8W5  plan-1  O19  0.020
 8W5  plan-2  C29  0.020
 8W5  plan-2  C31  0.020
 8W5  plan-2  O32  0.020
 8W5  plan-2  C33  0.020

