# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat May  2 18:26:47 2020
#   Inital geometry file: a 171 line input string
#   Ligand name: (2E,4E,6E,8E)-10-({(1R,2S,3S,4R)-4-hydroxy-2-methoxy-4-methyl-3-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]cyclohexyl}oxy)-10-oxodeca-2,4,6,8-tetraenoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CO[C@@H]1[C@@H](CC[C@@](C)(O)[C@H]1[C@@]2(C)O[C@@H]2CC=C(C)C)OC(=O)\C=C\C=C\C=C\C=C\C(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
 FUG  FUG  '(2E,4E,6E,8E)-10-({(1R,2S,3S,4R)-4-hydroxy-2-methoxy-4-methyl-3-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]cyclohexyl}oxy)-10-oxodeca-2,4,6,8-tetraenoic acid'  ligand  68  33  .  2022-09-22  2023-02-15
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_FUG
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
 FUG  C5    C  CH2    0  -0.465  -1.8609   3.3964   1.6331
 FUG  C4    C  CH1    0  -0.017  -1.6072   3.0272   0.1802
 FUG  C3    C  CH1    0   0.082  -2.8879   2.5093  -0.4774
 FUG  C2    C  CH1    0  -0.332  -3.4857   1.3297   0.3030
 FUG  C1    C  CT     0   0.215  -3.7994   1.7585   1.7553
 FUG  C6    C  CH2    0  -0.452  -2.5018   2.2532   2.4075
 FUG  O11   O  OH1    0  -0.670  -4.7369   2.8229   1.6930
 FUG  C11   C  CH3    0  -0.680  -4.3772   0.6139   2.5828
 FUG  C21   C  CT     0   0.276  -4.6556   0.6832  -0.4318
 FUG  C22   C  CH1    0   0.007  -4.8389  -0.7609  -0.2364
 FUG  C23   C  CH2    0  -0.567  -6.1509  -1.4999  -0.3223
 FUG  C24   C  C1     0  -0.249  -5.9655  -2.8463  -0.9566
 FUG  C25   C  C      0   0.084  -5.9691  -4.0390  -0.3561
 FUG  C2A   C  CH3    0  -0.710  -5.8189   1.5622  -0.8149
 FUG  O2A   O  O2     0  -0.495  -4.2617  -0.2613  -1.4282
 FUG  C2B   C  CH3    0  -0.717  -6.1810  -4.2588   1.1123
 FUG  C2C   C  CH3    0  -0.705  -5.7463  -5.2984  -1.1420
 FUG  O31   O  O2     0  -0.484  -2.6627   2.1001  -1.8014
 FUG  C31   C  CH3    0  -0.410  -2.5999   3.1526  -2.7305
 FUG  O41   O  O2     0  -0.476  -0.6475   1.9677   0.0659
 FUG  C41   C  C      0   0.600   0.6491   2.2456   0.1488
 FUG  O4A   O  O      0  -0.466   1.0906   3.3554   0.3504
 FUG  C42   C  C1     0  -0.435   1.4569   1.0360  -0.0441
 FUG  C43   C  C1     0  -0.171   2.7923   1.0610   0.1035
 FUG  C44   C  C1     0  -0.256   3.6434  -0.0808  -0.0851
 FUG  C45   C  C1     0  -0.230   4.9776  -0.0278   0.1117
 FUG  C46   C  C1     0  -0.255   5.8645  -1.1417  -0.0769
 FUG  C47   C  C1     0  -0.233   7.1930  -1.0674   0.1422
 FUG  C48   C  C1     0  -0.207   8.1013  -2.1710  -0.0476
 FUG  C49   C  C1     0  -0.421   9.4199  -2.0918   0.1767
 FUG  C4A   C  C      0   0.396  10.3757  -3.2431  -0.0247
 FUG  O4B   O  OC    -1  -0.614  11.5748  -2.9932   0.2176
 FUG  O4C   O  O      0  -0.600   9.8998  -4.3293  -0.4110
 FUG  H51   H  HCH2   0   0.256  -0.9325   3.7127   2.1105
 FUG  H52   H  HCH2   0   0.242  -2.5180   4.2694   1.6412
 FUG  H4    H  HCH1   0   0.260  -1.2414   3.9034  -0.3632
 FUG  H3    H  HCH1   0   0.225  -3.5969   3.3497  -0.4632
 FUG  H2    H  HCH1   0   0.255  -2.7152   0.5541   0.3847
 FUG  H61   H  HCH2   0   0.233  -1.8013   1.4186   2.4977
 FUG  H62   H  HCH2   0   0.242  -2.7160   2.5773   3.4309
 FUG  HOB   H  HOH1   0   0.446  -4.8969   3.1329   2.5911
 FUG  H111  H  HCH3   0   0.235  -4.5259   0.9420   3.6146
 FUG  H112  H  HCH3   0   0.241  -5.3429   0.2840   2.1999
 FUG  H113  H  HCH3   0   0.227  -3.7069  -0.2457   2.6070
 FUG  H22   H  HCH1   0   0.233  -4.1216  -1.2640   0.4154
 FUG  H231  H  HCH2   0   0.247  -6.5514  -1.5835   0.6907
 FUG  H232  H  HCH2   0   0.254  -6.8822  -0.9272  -0.8962
 FUG  H24   H  H      0   0.228  -5.7892  -2.8230  -2.0291
 FUG  H2A1  H  HCH3   0   0.241  -5.4838   2.4650  -1.3275
 FUG  H2A2  H  HCH3   0   0.235  -6.5023   1.0480  -1.4880
 FUG  H2A3  H  HCH3   0   0.242  -6.3766   1.8754   0.0648
 FUG  H2B1  H  HCH3   0   0.236  -7.0233  -4.9344   1.2813
 FUG  H2B2  H  HCH3   0   0.238  -5.3061  -4.7412   1.5553
 FUG  H2B3  H  HCH3   0   0.237  -6.3692  -3.3438   1.6696
 FUG  H2C1  H  HCH3   0   0.237  -5.6097  -5.1029  -2.2052
 FUG  H2C2  H  HCH3   0   0.232  -4.8646  -5.8334  -0.7794
 FUG  H2C3  H  HCH3   0   0.232  -6.5907  -5.9828  -1.0294
 FUG  H311  H  HCH3   0   0.236  -2.5427   2.7128  -3.7256
 FUG  H312  H  HCH3   0   0.205  -3.4918   3.7885  -2.6841
 FUG  H313  H  HCH3   0   0.207  -1.7227   3.7951  -2.5960
 FUG  H42   H  H      0   0.271   0.9441   0.1189  -0.3098
 FUG  H43   H  H      0   0.270   3.2748   1.9924   0.3855
 FUG  H44   H  H      0   0.260   3.1828  -1.0123  -0.4008
 FUG  H45   H  H      0   0.263   5.4232   0.9099   0.4342
 FUG  H46   H  H      0   0.257   5.4305  -2.0788  -0.4147
 FUG  H47   H  H      0   0.257   7.6171  -0.1263   0.4832
 FUG  H48   H  H      0   0.245   7.6807  -3.1104  -0.3939
 FUG  H49   H  H      0   0.232   9.8422  -1.1516   0.5224

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
 FUG  C5   C4    single  1.520  0.020  1.520
 FUG  C5   C6    single  1.522  0.020  1.522
 FUG  C5   H51   single  0.970  0.020  1.090
 FUG  C5   H52   single  0.970  0.020  1.090
 FUG  C4   C3    single  1.530  0.020  1.530
 FUG  C4   O41   single  1.434  0.020  1.434
 FUG  C4   H4    single  0.970  0.020  1.090
 FUG  C3   C2    single  1.535  0.020  1.535
 FUG  C3   O31   single  1.404  0.020  1.404
 FUG  C3   H3    single  0.970  0.020  1.090
 FUG  C2   C1    single  1.546  0.020  1.546
 FUG  C2   C21   single  1.525  0.020  1.525
 FUG  C2   H2    single  0.970  0.020  1.090
 FUG  C1   C6    single  1.534  0.020  1.534
 FUG  C1   O11   single  1.420  0.020  1.420
 FUG  C1   C11   single  1.526  0.020  1.526
 FUG  C6   H61   single  0.970  0.020  1.090
 FUG  C6   H62   single  0.970  0.020  1.090
 FUG  O11  HOB   single  0.850  0.020  0.980
 FUG  C11  H111  single  0.970  0.020  1.090
 FUG  C11  H112  single  0.970  0.020  1.090
 FUG  C11  H113  single  0.970  0.020  1.090
 FUG  C21  C22   single  1.469  0.020  1.469
 FUG  C21  C2A   single  1.508  0.020  1.508
 FUG  C21  O2A   single  1.428  0.020  1.428
 FUG  C22  C23   single  1.508  0.020  1.508
 FUG  C22  O2A   single  1.415  0.020  1.415
 FUG  C22  H22   single  0.970  0.020  1.090
 FUG  C23  C24   single  1.500  0.020  1.500
 FUG  C23  H231  single  0.970  0.020  1.090
 FUG  C23  H232  single  0.970  0.020  1.090
 FUG  C24  C25   double  1.335  0.020  1.335
 FUG  C24  H24   single  0.930  0.020  1.080
 FUG  C25  C2B   single  1.500  0.020  1.500
 FUG  C25  C2C   single  1.501  0.020  1.501
 FUG  C2A  H2A1  single  0.970  0.020  1.090
 FUG  C2A  H2A2  single  0.970  0.020  1.090
 FUG  C2A  H2A3  single  0.970  0.020  1.090
 FUG  C2B  H2B1  single  0.970  0.020  1.090
 FUG  C2B  H2B2  single  0.970  0.020  1.090
 FUG  C2B  H2B3  single  0.970  0.020  1.090
 FUG  C2C  H2C1  single  0.970  0.020  1.090
 FUG  C2C  H2C2  single  0.970  0.020  1.090
 FUG  C2C  H2C3  single  0.970  0.020  1.090
 FUG  O31  C31   single  1.405  0.020  1.405
 FUG  C31  H311  single  0.970  0.020  1.090
 FUG  C31  H312  single  0.970  0.020  1.090
 FUG  C31  H313  single  0.970  0.020  1.090
 FUG  O41  C41   single  1.329  0.020  1.329
 FUG  C41  O4A   double  1.211  0.020  1.211
 FUG  C41  C42   single  1.467  0.020  1.467
 FUG  C42  C43   double  1.344  0.020  1.344
 FUG  C42  H42   single  0.930  0.020  1.080
 FUG  C43  C44   single  1.437  0.020  1.437
 FUG  C43  H43   single  0.930  0.020  1.080
 FUG  C44  C45   double  1.350  0.020  1.350
 FUG  C44  H44   single  0.930  0.020  1.080
 FUG  C45  C46   single  1.436  0.020  1.436
 FUG  C45  H45   single  0.930  0.020  1.080
 FUG  C46  C47   double  1.349  0.020  1.349
 FUG  C46  H46   single  0.930  0.020  1.080
 FUG  C47  C48   single  1.442  0.020  1.442
 FUG  C47  H47   single  0.930  0.020  1.080
 FUG  C48  C49   double  1.340  0.020  1.340
 FUG  C48  H48   single  0.930  0.020  1.080
 FUG  C49  C4A   single  1.510  0.020  1.510
 FUG  C49  H49   single  0.930  0.020  1.080
 FUG  C4A  O4B   deloc   1.249  0.020  1.249
 FUG  C4A  O4C   deloc   1.247  0.020  1.247

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
 FUG  H52   C5   H51   106.08  3.000
 FUG  H52   C5   C6    110.07  3.000
 FUG  H51   C5   C6    110.70  3.000
 FUG  H52   C5   C4    107.54  3.000
 FUG  H51   C5   C4    110.28  3.000
 FUG  C6    C5   C4    111.96  3.000
 FUG  H4    C4   O41   109.17  3.000
 FUG  H4    C4   C3    109.72  3.000
 FUG  O41   C4   C3    106.01  3.000
 FUG  H4    C4   C5    109.63  3.000
 FUG  O41   C4   C5    111.54  3.000
 FUG  C3    C4   C5    110.69  3.000
 FUG  H3    C3   O31   109.78  3.000
 FUG  H3    C3   C2    109.24  3.000
 FUG  O31   C3   C2    108.53  3.000
 FUG  H3    C3   C4    105.99  3.000
 FUG  O31   C3   C4    111.70  3.000
 FUG  C2    C3   C4    111.56  3.000
 FUG  H2    C2   C21   105.97  3.000
 FUG  H2    C2   C1    105.59  3.000
 FUG  C21   C2   C1    114.48  3.000
 FUG  H2    C2   C3    107.92  3.000
 FUG  C21   C2   C3    112.30  3.000
 FUG  C1    C2   C3    110.08  3.000
 FUG  C11   C1   O11   109.64  3.000
 FUG  C11   C1   C6    109.36  3.000
 FUG  O11   C1   C6    109.60  3.000
 FUG  C11   C1   C2    112.22  3.000
 FUG  O11   C1   C2    107.50  3.000
 FUG  C6    C1   C2    108.48  3.000
 FUG  H62   C6   H61   105.92  3.000
 FUG  H62   C6   C1    109.11  3.000
 FUG  H61   C6   C1    109.32  3.000
 FUG  H62   C6   C5    109.61  3.000
 FUG  H61   C6   C5    110.21  3.000
 FUG  C1    C6   C5    112.46  3.000
 FUG  HOB   O11  C1    108.06  3.000
 FUG  H113  C11  H112  108.29  3.000
 FUG  H113  C11  H111  107.42  3.000
 FUG  H112  C11  H111  107.58  3.000
 FUG  H113  C11  C1    111.75  3.000
 FUG  H112  C11  C1    111.83  3.000
 FUG  H111  C11  C1    109.77  3.000
 FUG  O2A   C21  C2A   114.90  3.000
 FUG  O2A   C21  C22    58.47  3.000
 FUG  C2A   C21  C22   120.72  3.000
 FUG  O2A   C21  C2    113.88  3.000
 FUG  C2A   C21  C2    117.85  3.000
 FUG  C22   C21  C2    116.64  3.000
 FUG  H22   C22  O2A   113.42  3.000
 FUG  H22   C22  C23   112.32  3.000
 FUG  O2A   C22  C23   118.67  3.000
 FUG  H22   C22  C21   116.77  3.000
 FUG  O2A   C22  C21    59.34  3.000
 FUG  C23   C22  C21   125.64  3.000
 FUG  H232  C23  H231  106.38  3.000
 FUG  H232  C23  C24   109.35  3.000
 FUG  H231  C23  C24   111.64  3.000
 FUG  H232  C23  C22   110.83  3.000
 FUG  H231  C23  C22   107.67  3.000
 FUG  C24   C23  C22   110.87  3.000
 FUG  H24   C24  C25   117.59  3.000
 FUG  H24   C24  C23   114.71  3.000
 FUG  C25   C24  C23   127.68  3.000
 FUG  C2C   C25  C2B   114.24  3.000
 FUG  C2C   C25  C24   120.90  3.000
 FUG  C2B   C25  C24   124.86  3.000
 FUG  H2A3  C2A  H2A2  108.32  3.000
 FUG  H2A3  C2A  H2A1  107.41  3.000
 FUG  H2A2  C2A  H2A1  107.06  3.000
 FUG  H2A3  C2A  C21   110.97  3.000
 FUG  H2A2  C2A  C21   111.49  3.000
 FUG  H2A1  C2A  C21   111.40  3.000
 FUG  C22   O2A  C21    62.19  3.000
 FUG  H2B3  C2B  H2B2  107.59  3.000
 FUG  H2B3  C2B  H2B1  107.91  3.000
 FUG  H2B2  C2B  H2B1  106.34  3.000
 FUG  H2B3  C2B  C25   113.75  3.000
 FUG  H2B2  C2B  C25   110.39  3.000
 FUG  H2B1  C2B  C25   110.54  3.000
 FUG  H2C3  C2C  H2C2  106.41  3.000
 FUG  H2C3  C2C  H2C1  108.05  3.000
 FUG  H2C2  C2C  H2C1  108.07  3.000
 FUG  H2C3  C2C  C25   110.91  3.000
 FUG  H2C2  C2C  C25   110.89  3.000
 FUG  H2C1  C2C  C25   112.27  3.000
 FUG  C31   O31  C3    114.35  3.000
 FUG  H313  C31  H312  107.82  3.000
 FUG  H313  C31  H311  107.87  3.000
 FUG  H312  C31  H311  108.39  3.000
 FUG  H313  C31  O31   113.20  3.000
 FUG  H312  C31  O31   111.72  3.000
 FUG  H311  C31  O31   107.69  3.000
 FUG  C41   O41  C4    119.58  3.000
 FUG  C42   C41  O4A   125.20  3.000
 FUG  C42   C41  O41   110.90  3.000
 FUG  O4A   C41  O41   123.90  3.000
 FUG  H42   C42  C43   120.85  3.000
 FUG  H42   C42  C41   117.99  3.000
 FUG  C43   C42  C41   121.16  3.000
 FUG  H43   C43  C44   116.91  3.000
 FUG  H43   C43  C42   119.07  3.000
 FUG  C44   C43  C42   124.03  3.000
 FUG  H44   C44  C45   119.69  3.000
 FUG  H44   C44  C43   117.94  3.000
 FUG  C45   C44  C43   122.37  3.000
 FUG  H45   C45  C46   117.05  3.000
 FUG  H45   C45  C44   118.84  3.000
 FUG  C46   C45  C44   124.11  3.000
 FUG  H46   C46  C47   119.45  3.000
 FUG  H46   C46  C45   117.58  3.000
 FUG  C47   C46  C45   122.97  3.000
 FUG  H47   C47  C48   117.27  3.000
 FUG  H47   C47  C46   118.88  3.000
 FUG  C48   C47  C46   123.85  3.000
 FUG  H48   C48  C49   119.05  3.000
 FUG  H48   C48  C47   117.40  3.000
 FUG  C49   C48  C47   123.55  3.000
 FUG  H49   C49  C4A   117.13  3.000
 FUG  H49   C49  C48   119.12  3.000
 FUG  C4A   C49  C48   123.75  3.000
 FUG  O4C   C4A  O4B   126.94  3.000
 FUG  O4C   C4A  C49   117.63  3.000
 FUG  O4B   C4A  C49   115.43  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
 FUG  Var_01  C1    C6   C5   C4    -55.44  30.0  1
 FUG  Var_02  O2A   C22  C21  C2   -102.92  30.0  1
 FUG  Var_03  C2A   C21  O2A  C22  -112.08  30.0  1
 FUG  Var_04  C24   C23  C22  C21   142.61  30.0  3
 FUG  Var_05  H2A1  C2A  C21  C2     49.87  30.0  3
 FUG  Var_06  O4A   C41  O41  C4      1.83  30.0  3
 FUG  Var_07  C25   C24  C23  C22   105.41  30.0  3
 FUG  Var_08  H311  C31  O31  C3   -173.37  30.0  3
 FUG  Var_09  C2B   C25  C24  C23     0.70   0.0  2
 FUG  Var_10  C44   C43  C42  C41  -179.26   0.0  2
 FUG  Var_11  C46   C45  C44  C43  -179.43   0.0  2
 FUG  Var_12  C48   C47  C46  C45  -179.66   0.0  2
 FUG  Var_13  C4A   C49  C48  C47  -179.80   0.0  2
 FUG  Var_14  C43   C42  C41  O41  -174.67  30.0  2
 FUG  Var_15  C45   C44  C43  C42  -177.94  30.0  2
 FUG  Var_16  C47   C46  C45  C44  -179.17  30.0  2
 FUG  Var_17  C49   C48  C47  C46  -179.74  30.0  2
 FUG  Var_18  O4B   C4A  C49  C48   179.26  30.0  2
 FUG  Var_19  H2B1  C2B  C25  C24   123.42  30.0  3
 FUG  Var_20  H2C1  C2C  C25  C24    -1.00  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
 FUG  chir_01  C4   C5   C3   O41  positiv
 FUG  chir_02  C3   O31  C4   C2   positiv
 FUG  chir_03  C2   C3   C1   C21  negativ
 FUG  chir_04  C1   C2   C6   C11  positiv
 FUG  chir_05  C21  C22  C2A  O2A  both
 FUG  chir_06  C22  O2A  C21  C23  both

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
 FUG  plan-1  C49  0.020
 FUG  plan-1  C4A  0.020
 FUG  plan-1  O4B  0.020
 FUG  plan-1  O4C  0.020
 FUG  plan-2  C23  0.020
 FUG  plan-2  C24  0.020
 FUG  plan-2  C25  0.020
 FUG  plan-2  C2B  0.020
 FUG  plan-2  C2C  0.020
 FUG  plan-2  H24  0.020
 FUG  plan-3  O41  0.020
 FUG  plan-3  C41  0.020
 FUG  plan-3  O4A  0.020
 FUG  plan-3  C42  0.020
 FUG  plan-4  C41  0.020
 FUG  plan-4  C42  0.020
 FUG  plan-4  C43  0.020
 FUG  plan-4  C44  0.020
 FUG  plan-4  H42  0.020
 FUG  plan-4  H43  0.020
 FUG  plan-5  C43  0.020
 FUG  plan-5  C44  0.020
 FUG  plan-5  C45  0.020
 FUG  plan-5  C46  0.020
 FUG  plan-5  H44  0.020
 FUG  plan-5  H45  0.020
 FUG  plan-6  C45  0.020
 FUG  plan-6  C46  0.020
 FUG  plan-6  C47  0.020
 FUG  plan-6  C48  0.020
 FUG  plan-6  H46  0.020
 FUG  plan-6  H47  0.020
 FUG  plan-7  C47  0.020
 FUG  plan-7  C48  0.020
 FUG  plan-7  C49  0.020
 FUG  plan-7  C4A  0.020
 FUG  plan-7  H48  0.020
 FUG  plan-7  H49  0.020

