# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Jul 30 16:10:22 2021
#   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  69  33  .  2022-09-22  2022-11-17
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

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  -0.456  18.1164  27.6818  20.8551
 FUG  C4    C  CH1   0  -0.035  16.7593  28.3226  21.0693
 FUG  C3    C  CH1   0   0.095  16.2420  28.9617  19.7796
 FUG  C2    C  CH1   0  -0.327  17.2445  29.9669  19.1926
 FUG  C1    C  CT    0   0.205  18.6140  29.2735  18.9304
 FUG  C6    C  CH2   0  -0.430  19.1092  28.6564  20.2418
 FUG  O11   O  OH1   0  -0.674  18.4845  28.1940  18.0141
 FUG  C11   C  CH3   0  -0.705  19.6750  30.2479  18.4285
 FUG  C21   C  CT    0   0.265  16.6400  30.7028  17.9968
 FUG  C22   C  CH1   0   0.031  17.1731  32.0350  17.6711
 FUG  C23   C  CH2   0  -0.578  17.1779  32.6491  16.2896
 FUG  C24   C  C1    0  -0.272  18.2997  32.0825  15.4722
 FUG  C25   C  C     0   0.100  19.5023  32.6208  15.2568
 FUG  C2A   C  CH3   0  -0.732  15.9265  29.8805  16.9491
 FUG  O2A   O  O2    0  -0.499  15.9403  31.8983  18.3492
 FUG  C2B   C  CH3   0  -0.707  20.5401  31.8921  14.4553
 FUG  C2C   C  CH3   0  -0.720  19.9481  33.9468  15.7958
 FUG  O31   O  O2    0  -0.485  15.0249  29.6287  19.9970
 FUG  C31   C  CH3   0  -0.413  13.8954  28.7891  20.0244
 FUG  O41   O  O2    0  -0.475  16.9013  29.3627  22.0461
 FUG  C41   C  C     0   0.603  16.0262  29.4903  23.0356
 FUG  O4A   O  O     0  -0.457  15.1387  28.7054  23.2793
 FUG  C42   C  C1    0  -0.424  16.3053  30.7095  23.8099
 FUG  C43   C  C1    0  -0.172  15.6273  30.9989  24.9307
 FUG  C44   C  C1    0  -0.241  15.8651  32.1866  25.7073
 FUG  C45   C  C1    0  -0.234  15.2053  32.4589  26.8506
 FUG  C46   C  C1    0  -0.232  15.4386  33.6491  27.6212
 FUG  C47   C  C1    0  -0.243  14.7975  33.9301  28.7734
 FUG  C48   C  C1    0  -0.169  15.0526  35.1336  29.5182
 FUG  C49   C  C1    0  -0.412  14.4345  35.4437  30.6687
 FUG  C4A   C  C     0   0.528  14.7425  36.6912  31.3792
 FUG  O4B   O  OH1   0  -0.603  14.0188  36.8176  32.4884
 FUG  O4C   O  O     0  -0.453  15.5502  37.5187  31.0204
 FUG  H51   H  HCH2  0   0.244  17.9814  26.8153  20.2040
 FUG  H52   H  HCH2  0   0.252  18.4944  27.2955  21.8041
 FUG  H4    H  HCH1  0   0.269  16.0525  27.5725  21.4307
 FUG  H3    H  HCH1  0   0.223  16.1052  28.1420  19.0588
 FUG  H2    H  HCH1  0   0.247  17.4346  30.7329  19.9528
 FUG  H61   H  HCH2  0   0.242  20.0582  28.1484  20.0525
 FUG  H62   H  HCH2  0   0.234  19.3272  29.4611  20.9481
 FUG  HOB   H  HOH1  0   0.446  18.5269  28.5384  17.1171
 FUG  H111  H  HCH3  0   0.243  20.6374  29.7372  18.3610
 FUG  H112  H  HCH3  0   0.232  19.7927  31.0942  19.1052
 FUG  H113  H  HCH3  0   0.251  19.4425  30.6494  17.4410
 FUG  H22   H  HCH1  0   0.233  17.9846  32.4030  18.3000
 FUG  H231  H  HCH2  0   0.259  17.2596  33.7334  16.3924
 FUG  H232  H  HCH2  0   0.253  16.2245  32.4609  15.7924
 FUG  H24   H  H     0   0.229  18.1070  31.0979  15.0518
 FUG  H2A1  H  HCH3  0   0.254  14.9671  29.5286  17.3300
 FUG  H2A2  H  HCH3  0   0.225  16.4946  29.0019  16.6534
 FUG  H2A3  H  HCH3  0   0.248  15.7199  30.4524  16.0465
 FUG  H2B1  H  HCH3  0   0.237  20.1896  30.9163  14.1209
 FUG  H2B2  H  HCH3  0   0.232  21.4496  31.7418  15.0429
 FUG  H2B3  H  HCH3  0   0.234  20.8330  32.4687  13.5742
 FUG  H2C1  H  HCH3  0   0.240  19.1566  34.5019  16.2953
 FUG  H2C2  H  HCH3  0   0.236  20.3495  34.5747  14.9970
 FUG  H2C3  H  HCH3  0   0.239  20.7583  33.8063  16.5160
 FUG  H311  H  HCH3  0   0.205  13.8107  28.1941  19.1075
 FUG  H312  H  HCH3  0   0.234  13.0146  29.4259  20.1008
 FUG  H313  H  HCH3  0   0.214  13.8927  28.1046  20.8775
 FUG  H42   H  H     0   0.276  17.0816  31.3724  23.4459
 FUG  H43   H  H     0   0.275  14.8611  30.3170  25.2870
 FUG  H44   H  H     0   0.268  16.6107  32.8858  25.3405
 FUG  H45   H  H     0   0.270  14.4627  31.7577  27.2205
 FUG  H46   H  H     0   0.270  16.1739  34.3516  27.2387
 FUG  H47   H  H     0   0.269  14.0627  33.2342  29.1665
 FUG  H48   H  H     0   0.276  15.7891  35.8183  29.1086
 FUG  H49   H  H     0   0.281  13.6949  34.7796  31.0999
 FUG  HOB4  H  HOH1  0   0.481  14.2477  37.6455  32.9357

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  1.516  0.020  1.516
 FUG  C5   C6    single  1.520  0.020  1.520
 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  1.536  0.020  1.536
 FUG  C3   O31   single  1.405  0.020  1.405
 FUG  C3   H3    single  0.970  0.020  1.090
 FUG  C2   C1    single  1.557  0.020  1.557
 FUG  C2   C21   single  1.529  0.020  1.529
 FUG  C2   H2    single  0.970  0.020  1.090
 FUG  C1   C6    single  1.532  0.020  1.532
 FUG  C1   O11   single  1.422  0.020  1.422
 FUG  C1   C11   single  1.525  0.020  1.525
 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  1.471  0.020  1.471
 FUG  C21  C2A   single  1.511  0.020  1.511
 FUG  C21  O2A   single  1.429  0.020  1.429
 FUG  C22  C23   single  1.512  0.020  1.512
 FUG  C22  O2A   single  1.414  0.020  1.414
 FUG  C22  H22   single  0.970  0.020  1.090
 FUG  C23  C24   single  1.499  0.020  1.499
 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  1.499  0.020  1.499
 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  1.408  0.020  1.408
 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  1.327  0.020  1.327
 FUG  C41  O4A   double  1.210  0.020  1.210
 FUG  C41  C42   single  1.471  0.020  1.471
 FUG  C42  C43   double  1.342  0.020  1.342
 FUG  C42  H42   single  0.930  0.020  1.080
 FUG  C43  C44   single  1.439  0.020  1.439
 FUG  C43  H43   single  0.930  0.020  1.080
 FUG  C44  C45   double  1.348  0.020  1.348
 FUG  C44  H44   single  0.930  0.020  1.080
 FUG  C45  C46   single  1.437  0.020  1.437
 FUG  C45  H45   single  0.930  0.020  1.080
 FUG  C46  C47   double  1.348  0.020  1.348
 FUG  C46  H46   single  0.930  0.020  1.080
 FUG  C47  C48   single  1.438  0.020  1.438
 FUG  C47  H47   single  0.930  0.020  1.080
 FUG  C48  C49   double  1.342  0.020  1.342
 FUG  C48  H48   single  0.930  0.020  1.080
 FUG  C49  C4A   single  1.468  0.020  1.468
 FUG  C49  H49   single  0.930  0.020  1.080
 FUG  C4A  O4B   single  1.330  0.020  1.330
 FUG  C4A  O4C   double  1.211  0.020  1.211
 FUG  O4B  HOB4  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
 FUG  H52   C5   H51   106.27  3.000
 FUG  H52   C5   C6    110.56  3.000
 FUG  H51   C5   C6    110.41  3.000
 FUG  H52   C5   C4    109.67  3.000
 FUG  H51   C5   C4    108.00  3.000
 FUG  C6    C5   C4    111.75  3.000
 FUG  H4    C4   O41   109.69  3.000
 FUG  H4    C4   C3    110.31  3.000
 FUG  O41   C4   C3    107.74  3.000
 FUG  H4    C4   C5    109.62  3.000
 FUG  O41   C4   C5    108.32  3.000
 FUG  C3    C4   C5    111.11  3.000
 FUG  H3    C3   O31   110.33  3.000
 FUG  H3    C3   C2    108.56  3.000
 FUG  O31   C3   C2    108.29  3.000
 FUG  H3    C3   C4    106.45  3.000
 FUG  O31   C3   C4    111.16  3.000
 FUG  C2    C3   C4    112.02  3.000
 FUG  H2    C2   C21   105.95  3.000
 FUG  H2    C2   C1    105.99  3.000
 FUG  C21   C2   C1    115.49  3.000
 FUG  H2    C2   C3    107.79  3.000
 FUG  C21   C2   C3    110.84  3.000
 FUG  C1    C2   C3    110.30  3.000
 FUG  C11   C1   O11   109.65  3.000
 FUG  C11   C1   C6    108.31  3.000
 FUG  O11   C1   C6    105.98  3.000
 FUG  C11   C1   C2    112.50  3.000
 FUG  O11   C1   C2    111.50  3.000
 FUG  C6    C1   C2    108.64  3.000
 FUG  H62   C6   H61   106.33  3.000
 FUG  H62   C6   C1    108.73  3.000
 FUG  H61   C6   C1    108.65  3.000
 FUG  H62   C6   C5    109.98  3.000
 FUG  H61   C6   C5    109.81  3.000
 FUG  C1    C6   C5    113.11  3.000
 FUG  HOB   O11  C1    108.97  3.000
 FUG  H113  C11  H112  107.41  3.000
 FUG  H113  C11  H111  107.70  3.000
 FUG  H112  C11  H111  107.85  3.000
 FUG  H113  C11  C1    112.62  3.000
 FUG  H112  C11  C1    111.52  3.000
 FUG  H111  C11  C1    109.56  3.000
 FUG  O2A   C21  C2A   113.26  3.000
 FUG  O2A   C21  C22    58.31  3.000
 FUG  C2A   C21  C22   120.68  3.000
 FUG  O2A   C21  C2    113.79  3.000
 FUG  C2A   C21  C2    117.85  3.000
 FUG  C22   C21  C2    117.76  3.000
 FUG  H22   C22  O2A   113.89  3.000
 FUG  H22   C22  C23   112.80  3.000
 FUG  O2A   C22  C23   118.71  3.000
 FUG  H22   C22  C21   116.58  3.000
 FUG  O2A   C22  C21    59.36  3.000
 FUG  C23   C22  C21   124.83  3.000
 FUG  H232  C23  H231  106.22  3.000
 FUG  H232  C23  C24   109.88  3.000
 FUG  H231  C23  C24   111.74  3.000
 FUG  H232  C23  C22   110.08  3.000
 FUG  H231  C23  C22   108.51  3.000
 FUG  C24   C23  C22   110.31  3.000
 FUG  H24   C24  C25   117.53  3.000
 FUG  H24   C24  C23   114.84  3.000
 FUG  C25   C24  C23   127.56  3.000
 FUG  C2C   C25  C2B   114.58  3.000
 FUG  C2C   C25  C24   124.51  3.000
 FUG  C2B   C25  C24   120.90  3.000
 FUG  H2A3  C2A  H2A2  107.35  3.000
 FUG  H2A3  C2A  H2A1  106.99  3.000
 FUG  H2A2  C2A  H2A1  107.09  3.000
 FUG  H2A3  C2A  C21   112.26  3.000
 FUG  H2A2  C2A  C21   112.44  3.000
 FUG  H2A1  C2A  C21   110.42  3.000
 FUG  C22   O2A  C21    62.33  3.000
 FUG  H2B3  C2B  H2B2  106.43  3.000
 FUG  H2B3  C2B  H2B1  108.14  3.000
 FUG  H2B2  C2B  H2B1  108.03  3.000
 FUG  H2B3  C2B  C25   111.09  3.000
 FUG  H2B2  C2B  C25   110.80  3.000
 FUG  H2B1  C2B  C25   112.12  3.000
 FUG  H2C3  C2C  H2C2  106.46  3.000
 FUG  H2C3  C2C  H2C1  107.59  3.000
 FUG  H2C2  C2C  H2C1  108.04  3.000
 FUG  H2C3  C2C  C25   110.10  3.000
 FUG  H2C2  C2C  C25   110.77  3.000
 FUG  H2C1  C2C  C25   113.57  3.000
 FUG  C31   O31  C3    114.52  3.000
 FUG  H313  C31  H312  108.01  3.000
 FUG  H313  C31  H311  108.20  3.000
 FUG  H312  C31  H311  108.26  3.000
 FUG  H313  C31  O31   112.98  3.000
 FUG  H312  C31  O31   107.54  3.000
 FUG  H311  C31  O31   111.68  3.000
 FUG  C41   O41  C4    120.82  3.000
 FUG  C42   C41  O4A   124.82  3.000
 FUG  C42   C41  O41   110.31  3.000
 FUG  O4A   C41  O41   124.86  3.000
 FUG  H42   C42  C43   120.71  3.000
 FUG  H42   C42  C41   117.78  3.000
 FUG  C43   C42  C41   121.52  3.000
 FUG  H43   C43  C44   117.26  3.000
 FUG  H43   C43  C42   119.68  3.000
 FUG  C44   C43  C42   123.06  3.000
 FUG  H44   C44  C45   119.51  3.000
 FUG  H44   C44  C43   117.56  3.000
 FUG  C45   C44  C43   122.93  3.000
 FUG  H45   C45  C46   117.59  3.000
 FUG  H45   C45  C44   119.55  3.000
 FUG  C46   C45  C44   122.87  3.000
 FUG  H46   C46  C47   119.21  3.000
 FUG  H46   C46  C45   117.17  3.000
 FUG  C47   C46  C45   123.62  3.000
 FUG  H47   C47  C48   117.96  3.000
 FUG  H47   C47  C46   119.85  3.000
 FUG  C48   C47  C46   122.19  3.000
 FUG  H48   C48  C49   119.34  3.000
 FUG  H48   C48  C47   116.91  3.000
 FUG  C49   C48  C47   123.75  3.000
 FUG  H49   C49  C4A   118.12  3.000
 FUG  H49   C49  C48   120.92  3.000
 FUG  C4A   C49  C48   120.96  3.000
 FUG  O4C   C4A  O4B   123.02  3.000
 FUG  O4C   C4A  C49   125.26  3.000
 FUG  O4B   C4A  C49   111.72  3.000
 FUG  HOB4  O4B  C4A   109.74  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  CONST_01  HOB4  O4B  C4A  C49   180.00   0.0  0
 FUG  Var_01    C1    C6   C5   C4    -55.47  30.0  1
 FUG  Var_02    O2A   C22  C21  C2   -102.17  30.0  1
 FUG  Var_03    C2A   C21  O2A  C22  -112.79  30.0  1
 FUG  Var_04    C24   C23  C22  C21   -78.87  30.0  3
 FUG  Var_05    H2A1  C2A  C21  C2     72.90  30.0  3
 FUG  Var_06    O4A   C41  O41  C4      7.24  30.0  3
 FUG  Var_07    C25   C24  C23  C22   -97.92  30.0  3
 FUG  Var_08    H311  C31  O31  C3    -55.94  30.0  3
 FUG  Var_09    C2B   C25  C24  C23   177.38   0.0  2
 FUG  Var_10    C44   C43  C42  C41  -179.47   0.0  2
 FUG  Var_11    C46   C45  C44  C43  -179.65   0.0  2
 FUG  Var_12    C48   C47  C46  C45  -179.81   0.0  2
 FUG  Var_13    C4A   C49  C48  C47  -179.99   0.0  2
 FUG  Var_14    C43   C42  C41  O41  -174.28  30.0  2
 FUG  Var_15    C45   C44  C43  C42  -178.32  30.0  2
 FUG  Var_16    C47   C46  C45  C44  -179.30  30.0  2
 FUG  Var_17    C49   C48  C47  C46  -179.90  30.0  2
 FUG  Var_18    O4B   C4A  C49  C48   179.50  30.0  2
 FUG  Var_19    H2B1  C2B  C25  C24    -1.20  30.0  3
 FUG  Var_20    H2C1  C2C  C25  C24    -6.71  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-1  HOB4  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

