# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun May  3 23:40:01 2020
#   Inital geometry file: a 169 line input string
#   Ligand name: (3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyl-5-hydroxy-4,6,9,10-tetramethyl-1-oxodecahydro-3a,9-propanocyclopenta[8]annulen-8-yl (piperidin-4-ylsulfanyl)acetate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@@H]1CC[C@@]23CCC(=O)[C@H]2[C@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]3C)OC(=O)CSC4CCNCC4
#
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
 G80  G80  '(3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyl-5-hydroxy-4,6,9,10-tetramethyl-1-oxodecahydro-3a,9-propanocyclopenta[8]annulen-8-yl (piperidin-4-ylsulfanyl)acetate'  ligand  76  33  .  2021-08-10  2021-08-10  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_G80
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
 G80  O1    O  O     0  -0.396   5.9480  -6.3721   7.1707
 G80  O2    O  OH1   0  -0.665  10.0920  -2.1758   4.3887
 G80  C1    C  CH2   0  -0.438   8.6647  -4.0569   7.4262
 G80  C2    C  CH2   0  -0.566   8.0024  -5.3523   7.8724
 G80  C3    C  C     0   0.427   6.7444  -5.4750   7.0399
 G80  C4    C  CH1   0  -0.374   6.7104  -4.3254   6.0332
 G80  C5    C  CT    0  -0.080   5.3339  -3.9095   5.4532
 G80  C6    C  CH1   0  -0.221   4.5134  -3.3055   6.6253
 G80  C7    C  CH2   0  -0.431   5.2765  -2.1836   7.3303
 G80  C8    C  CH2   0  -0.437   6.6393  -2.6331   7.8361
 G80  C9    C  CT    0  -0.083   7.5494  -3.2346   6.7484
 G80  C10   C  CH1   0  -0.275   8.1623  -2.1373   5.8349
 G80  C11   C  CH1   0   0.110   8.8017  -2.7243   4.5439
 G80  C12   C  CT    0  -0.180   7.9805  -2.5276   3.2373
 G80  C13   C  CH2   0  -0.475   6.6185  -3.2664   3.2672
 G80  C14   C  CH1   0   0.087   5.5691  -2.8714   4.3182
 G80  C15   C  CH3   0  -0.676   4.6278  -5.1407   4.8606
 G80  C16   C  CH3   0  -0.668   3.0856  -2.8601   6.3115
 G80  C17   C  CH3   0  -0.653   9.1400  -1.2514   6.6152
 G80  C18   C  CH3   0  -0.704   8.7534  -3.1820   2.0852
 G80  C19   C  C1    0  -0.102   7.7526  -1.0603   2.9804
 G80  C20   C  C2    0  -0.549   8.1873  -0.3527   1.9439
 G80  O3    O  O2    0  -0.469   4.3187  -2.6965   3.6166
 G80  C21   C  C     0   0.612   3.8762  -1.4869   3.3237
 G80  O4    O  O     0  -0.434   4.3968  -0.4518   3.6535
 G80  C22   C  CH2   0  -0.685   2.6063  -1.5728   2.5176
 G80  S1    S  S2    0  -0.012   2.0357   0.0932   2.1162
 G80  C23   C  CH1   0  -0.381   0.5756  -0.3254   1.0934
 G80  C24   C  CH2   0  -0.422   0.9556  -0.8835  -0.2762
 G80  C25   C  CH2   0  -0.288   1.5833   0.1790  -1.1656
 G80  C27   C  CH2   0  -0.294   0.4122   1.9413  -0.0110
 G80  C26   C  CH2   0  -0.432  -0.2608   0.9421   0.9197
 G80  N1    N  NH1   0  -0.597   0.6834   1.3135  -1.2925
 G80  H11A  H  HCH2  0   0.251   9.1123  -3.5116   8.2575
 G80  H12   H  HCH2  0   0.247   9.4660  -4.2664   6.7138
 G80  H21   H  HCH2  0   0.277   7.7193  -5.3409   8.9276
 G80  H22   H  HCH2  0   0.284   8.6290  -6.2352   7.7315
 G80  H4    H  HCH1  0   0.293   7.3188  -4.7497   5.2209
 G80  H6    H  HCH1  0   0.229   4.4142  -4.1211   7.3517
 G80  H71   H  HCH2  0   0.240   4.6842  -1.8407   8.1833
 G80  H72   H  HCH2  0   0.217   5.3684  -1.3085   6.6782
 G80  H81   H  HCH2  0   0.246   7.1383  -1.8100   8.3507
 G80  H82   H  HCH2  0   0.235   6.4732  -3.3880   8.6129
 G80  H10   H  HCH1  0   0.229   7.3528  -1.4622   5.5595
 G80  H11   H  HCH1  0   0.209   8.9032  -3.8119   4.6649
 G80  H131  H  HCH2  0   0.252   6.8132  -4.3419   3.3071
 G80  H132  H  HCH2  0   0.264   6.1757  -3.1014   2.2832
 G80  H14   H  HCH1  0   0.249   5.8219  -1.9092   4.7508
 G80  H151  H  HCH3  0   0.247   4.2552  -5.7911   5.6455
 G80  H152  H  HCH3  0   0.239   3.7799  -4.8638   4.2395
 G80  H153  H  HCH3  0   0.227   5.3125  -5.7309   4.2481
 G80  H161  H  HCH3  0   0.232   2.5336  -2.7482   7.2464
 G80  H162  H  HCH3  0   0.214   3.0458  -1.8908   5.8142
 G80  H163  H  HCH3  0   0.234   2.5440  -3.5836   5.7026
 G80  H171  H  HCH3  0   0.235   9.4329  -0.3849   6.0240
 G80  H172  H  HCH3  0   0.226   8.6677  -0.8698   7.5191
 G80  H173  H  HCH3  0   0.226  10.0476  -1.7735   6.9119
 G80  H181  H  HCH3  0   0.246   8.1556  -3.1895   1.1727
 G80  H182  H  HCH3  0   0.237   9.6853  -2.6705   1.8444
 G80  H183  H  HCH3  0   0.243   8.9923  -4.2205   2.3248
 G80  H19   H  H     0   0.243   7.1516  -0.5314   3.7130
 G80  H201  H  H     0   0.237   7.9465   0.6990   1.8557
 G80  H202  H  H     0   0.231   8.7877  -0.7729   1.1472
 G80  H221  H  HCH2  0   0.304   1.8487  -2.1184   3.0867
 G80  H222  H  HCH2  0   0.302   2.8023  -2.1519   1.6121
 G80  H23   H  HCH1  0   0.283  -0.0009  -1.0653   1.6544
 G80  H241  H  HCH2  0   0.235   0.0423  -1.2546  -0.7525
 G80  H242  H  HCH2  0   0.239   1.6276  -1.7397  -0.1859
 G80  H251  H  HCH2  0   0.194   2.5658   0.4584  -0.7548
 G80  H252  H  HCH2  0   0.233   1.7637  -0.2397  -2.1575
 G80  H271  H  HCH2  0   0.236  -0.2517   2.7935  -0.1689
 G80  H272  H  HCH2  0   0.194   1.3207   2.3389   0.4702
 G80  H261  H  HCH2  0   0.244  -0.4693   1.4035   1.8870
 G80  H262  H  HCH2  0   0.242  -1.2230   0.6501   0.4893
 G80  HN1   H  HNH1  0   0.351   1.0894   1.9956  -1.9193
 G80  HO2   H  HOH1  0   0.452  10.5795  -2.7161   3.7611

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
 G80  O1   C3    double  1.207  0.020  1.207
 G80  O2   C11   single  1.411  0.020  1.411
 G80  O2   HO2   single  0.850  0.020  0.980
 G80  C1   C9    single  1.543  0.020  1.543
 G80  C1   C2    single  1.522  0.020  1.522
 G80  C1   H11A  single  0.970  0.020  1.090
 G80  C1   H12   single  0.970  0.020  1.090
 G80  C2   C3    single  1.513  0.020  1.513
 G80  C2   H21   single  0.970  0.020  1.090
 G80  C2   H22   single  0.970  0.020  1.090
 G80  C3   C4    single  1.528  0.020  1.528
 G80  C4   C9    single  1.551  0.020  1.551
 G80  C4   C5    single  1.550  0.020  1.550
 G80  C4   H4    single  0.970  0.020  1.090
 G80  C5   C6    single  1.553  0.020  1.553
 G80  C5   C14   single  1.556  0.020  1.556
 G80  C5   C15   single  1.538  0.020  1.538
 G80  C6   C7    single  1.529  0.020  1.529
 G80  C6   C16   single  1.528  0.020  1.528
 G80  C6   H6    single  0.970  0.020  1.090
 G80  C7   C8    single  1.522  0.020  1.522
 G80  C7   H71   single  0.970  0.020  1.090
 G80  C7   H72   single  0.970  0.020  1.090
 G80  C8   C9    single  1.541  0.020  1.541
 G80  C8   H81   single  0.970  0.020  1.090
 G80  C8   H82   single  0.970  0.020  1.090
 G80  C9   C10   single  1.554  0.020  1.554
 G80  C10  C17   single  1.533  0.020  1.533
 G80  C10  C11   single  1.556  0.020  1.556
 G80  C10  H10   single  0.970  0.020  1.090
 G80  C11  C12   single  1.556  0.020  1.556
 G80  C11  H11   single  0.970  0.020  1.090
 G80  C12  C19   single  1.507  0.020  1.507
 G80  C12  C13   single  1.550  0.020  1.550
 G80  C12  C18   single  1.534  0.020  1.534
 G80  C13  C14   single  1.537  0.020  1.537
 G80  C13  H131  single  0.970  0.020  1.090
 G80  C13  H132  single  0.970  0.020  1.090
 G80  C14  O3    single  1.444  0.020  1.444
 G80  C14  H14   single  0.970  0.020  1.090
 G80  C15  H151  single  0.970  0.020  1.090
 G80  C15  H152  single  0.970  0.020  1.090
 G80  C15  H153  single  0.970  0.020  1.090
 G80  C16  H161  single  0.970  0.020  1.090
 G80  C16  H162  single  0.970  0.020  1.090
 G80  C16  H163  single  0.970  0.020  1.090
 G80  C17  H171  single  0.970  0.020  1.090
 G80  C17  H172  single  0.970  0.020  1.090
 G80  C17  H173  single  0.970  0.020  1.090
 G80  C18  H181  single  0.970  0.020  1.090
 G80  C18  H182  single  0.970  0.020  1.090
 G80  C18  H183  single  0.970  0.020  1.090
 G80  C19  C20   double  1.328  0.020  1.328
 G80  C19  H19   single  0.930  0.020  1.080
 G80  C20  H201  single  0.930  0.020  1.080
 G80  C20  H202  single  0.930  0.020  1.080
 G80  O3   C21   single  1.321  0.020  1.321
 G80  C21  O4    double  1.205  0.020  1.205
 G80  C21  C22   single  1.507  0.020  1.507
 G80  C22  S1    single  1.806  0.020  1.806
 G80  C22  H221  single  0.970  0.020  1.090
 G80  C22  H222  single  0.970  0.020  1.090
 G80  S1   C23   single  1.831  0.020  1.831
 G80  C23  C24   single  1.527  0.020  1.527
 G80  C23  C26   single  1.528  0.020  1.528
 G80  C23  H23   single  0.970  0.020  1.090
 G80  C24  C25   single  1.521  0.020  1.521
 G80  C24  H241  single  0.970  0.020  1.090
 G80  C24  H242  single  0.970  0.020  1.090
 G80  C25  N1    single  1.454  0.020  1.454
 G80  C25  H251  single  0.970  0.020  1.090
 G80  C25  H252  single  0.970  0.020  1.090
 G80  C27  C26   single  1.522  0.020  1.522
 G80  C27  N1    single  1.452  0.020  1.452
 G80  C27  H271  single  0.970  0.020  1.090
 G80  C27  H272  single  0.970  0.020  1.090
 G80  C26  H261  single  0.970  0.020  1.090
 G80  C26  H262  single  0.970  0.020  1.090
 G80  N1   HN1   single  0.890  0.020  1.040

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
 G80  HO2   O2   C11   108.50  3.000
 G80  H12   C1   H11A  106.98  3.000
 G80  H12   C1   C9    110.24  3.000
 G80  H11A  C1   C9    111.42  3.000
 G80  H12   C1   C2    110.32  3.000
 G80  H11A  C1   C2    112.39  3.000
 G80  C9    C1   C2    105.54  3.000
 G80  H22   C2   H21   106.37  3.000
 G80  H22   C2   C3    109.91  3.000
 G80  H21   C2   C3    108.47  3.000
 G80  H22   C2   C1    113.62  3.000
 G80  H21   C2   C1    112.77  3.000
 G80  C3    C2   C1    105.63  3.000
 G80  C4    C3   C2    108.65  3.000
 G80  C4    C3   O1    128.01  3.000
 G80  C2    C3   O1    123.31  3.000
 G80  H4    C4   C9    108.22  3.000
 G80  H4    C4   C5    108.56  3.000
 G80  C9    C4   C5    117.65  3.000
 G80  H4    C4   C3    100.60  3.000
 G80  C5    C4   C3    117.90  3.000
 G80  C9    C4   C3    102.31  3.000
 G80  C15   C5   C14   108.81  3.000
 G80  C15   C5   C6    111.07  3.000
 G80  C14   C5   C6    111.77  3.000
 G80  C15   C5   C4    109.69  3.000
 G80  C14   C5   C4    108.52  3.000
 G80  C6    C5   C4    106.92  3.000
 G80  H6    C6   C16   105.56  3.000
 G80  H6    C6   C7    106.58  3.000
 G80  C16   C6   C7    110.31  3.000
 G80  H6    C6   C5    104.98  3.000
 G80  C16   C6   C5    116.87  3.000
 G80  C7    C6   C5    111.69  3.000
 G80  H72   C7   H71   105.03  3.000
 G80  H72   C7   C8    111.03  3.000
 G80  H71   C7   C8    108.57  3.000
 G80  H72   C7   C6    110.71  3.000
 G80  H71   C7   C6    108.63  3.000
 G80  C8    C7   C6    112.55  3.000
 G80  H82   C8   H81   104.75  3.000
 G80  H82   C8   C9    108.73  3.000
 G80  H81   C8   C9    110.93  3.000
 G80  H82   C8   C7    107.66  3.000
 G80  H81   C8   C7    110.09  3.000
 G80  C9    C8   C7    114.19  3.000
 G80  C10   C9   C8    111.86  3.000
 G80  C10   C9   C4    116.04  3.000
 G80  C8    C9   C4    106.30  3.000
 G80  C10   C9   C1    110.46  3.000
 G80  C8    C9   C1    108.97  3.000
 G80  C4    C9   C1    102.64  3.000
 G80  H10   C10  C17   104.15  3.000
 G80  H10   C10  C11   109.23  3.000
 G80  C17   C10  C11   112.23  3.000
 G80  H10   C10  C9    107.05  3.000
 G80  C11   C10  C9    112.55  3.000
 G80  C17   C10  C9    111.13  3.000
 G80  H11   C11  C12   105.44  3.000
 G80  H11   C11  C10   108.67  3.000
 G80  C12   C11  C10   115.62  3.000
 G80  H11   C11  O2    108.20  3.000
 G80  C12   C11  O2    109.96  3.000
 G80  C10   C11  O2    108.69  3.000
 G80  C19   C12  C18   111.32  3.000
 G80  C18   C12  C13   104.71  3.000
 G80  C19   C12  C13   109.55  3.000
 G80  C18   C12  C11   108.11  3.000
 G80  C13   C12  C11   112.79  3.000
 G80  C19   C12  C11   110.24  3.000
 G80  H132  C13  H131  104.70  3.000
 G80  H132  C13  C14   107.50  3.000
 G80  H131  C13  C14   110.45  3.000
 G80  H132  C13  C12   105.49  3.000
 G80  H131  C13  C12   108.24  3.000
 G80  C14   C13  C12   119.39  3.000
 G80  H14   C14  O3    106.74  3.000
 G80  H14   C14  C13   109.98  3.000
 G80  O3    C14  C13   106.86  3.000
 G80  H14   C14  C5    109.64  3.000
 G80  O3    C14  C5    107.71  3.000
 G80  C13   C14  C5    115.50  3.000
 G80  H153  C15  H152  107.84  3.000
 G80  H153  C15  H151  107.28  3.000
 G80  H152  C15  H151  107.34  3.000
 G80  H153  C15  C5    111.16  3.000
 G80  H152  C15  C5    111.99  3.000
 G80  H151  C15  C5    111.02  3.000
 G80  H163  C16  H162  108.50  3.000
 G80  H163  C16  H161  107.18  3.000
 G80  H162  C16  H161  106.33  3.000
 G80  H163  C16  C6    112.68  3.000
 G80  H162  C16  C6    112.76  3.000
 G80  H161  C16  C6    109.06  3.000
 G80  H173  C17  H172  107.67  3.000
 G80  H173  C17  H171  107.78  3.000
 G80  H172  C17  H171  106.76  3.000
 G80  H173  C17  C10   113.17  3.000
 G80  H172  C17  C10   110.39  3.000
 G80  H171  C17  C10   110.79  3.000
 G80  H183  C18  H182  107.92  3.000
 G80  H183  C18  H181  107.27  3.000
 G80  H182  C18  H181  106.68  3.000
 G80  H183  C18  C12   110.55  3.000
 G80  H182  C18  C12   113.36  3.000
 G80  H181  C18  C12   110.79  3.000
 G80  H19   C19  C20   116.65  3.000
 G80  H19   C19  C12   116.31  3.000
 G80  C20   C19  C12   127.03  3.000
 G80  H202  C20  H201  116.14  3.000
 G80  H202  C20  C19   123.31  3.000
 G80  H201  C20  C19   120.55  3.000
 G80  C21   O3   C14   120.57  3.000
 G80  C22   C21  O4    124.04  3.000
 G80  C22   C21  O3    110.41  3.000
 G80  O4    C21  O3    125.55  3.000
 G80  H222  C22  H221  106.93  3.000
 G80  H222  C22  S1    111.19  3.000
 G80  H221  C22  S1    110.92  3.000
 G80  H222  C22  C21   108.81  3.000
 G80  H221  C22  C21   109.51  3.000
 G80  S1    C22  C21   109.43  3.000
 G80  C23   S1   C22    99.51  3.000
 G80  H23   C23  C26   109.33  3.000
 G80  H23   C23  C24   110.13  3.000
 G80  C26   C23  C24   109.71  3.000
 G80  H23   C23  S1    106.78  3.000
 G80  C26   C23  S1    108.07  3.000
 G80  C24   C23  S1    112.71  3.000
 G80  H242  C24  H241  106.47  3.000
 G80  H242  C24  C25   110.01  3.000
 G80  H241  C24  C25   109.07  3.000
 G80  H242  C24  C23   111.43  3.000
 G80  H241  C24  C23   107.84  3.000
 G80  C25   C24  C23   111.83  3.000
 G80  H252  C25  H251  106.79  3.000
 G80  H252  C25  N1    108.80  3.000
 G80  H251  C25  N1    112.77  3.000
 G80  H252  C25  C24   109.36  3.000
 G80  H251  C25  C24   109.11  3.000
 G80  N1    C25  C24   109.92  3.000
 G80  H272  C27  H271  106.43  3.000
 G80  H272  C27  N1    112.78  3.000
 G80  H271  C27  N1    108.86  3.000
 G80  H272  C27  C26   109.53  3.000
 G80  H271  C27  C26   109.39  3.000
 G80  N1    C27  C26   109.77  3.000
 G80  H262  C26  H261  107.06  3.000
 G80  H262  C26  C27   108.88  3.000
 G80  H261  C26  C27   110.41  3.000
 G80  H262  C26  C23   107.74  3.000
 G80  H261  C26  C23   110.75  3.000
 G80  C27   C26  C23   111.83  3.000
 G80  HN1   N1   C27   109.28  3.000
 G80  HN1   N1   C25   109.39  3.000
 G80  C27   N1   C25   112.08  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
 G80  Var_01  C4    C3   C2   C1      4.30  30.0  1
 G80  Var_02  C9    C1   C2   C3     20.04  30.0  1
 G80  Var_03  C9    C8   C7   C6     55.73  30.0  1
 G80  Var_04  N1    C25  C24  C23   -56.03  30.0  1
 G80  Var_05  N1    C27  C26  C23    56.19  30.0  1
 G80  Var_06  C27   N1   C25  C24    61.25  30.0  1
 G80  Var_07  C26   C27  N1   C25   -61.28  30.0  1
 G80  Var_08  O4    C21  O3   C14    -4.13  30.0  3
 G80  Var_09  H201  C20  C19  C12   178.96   0.0  2
 G80  Var_10  H221  C22  S1   C23   -61.84  30.0  1
 G80  Var_11  S1    C22  C21  O3   -179.36  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
 G80  chir_01  C4   C3   C9   C5   positiv
 G80  chir_02  C5   C6   C4   C15  negativ
 G80  chir_03  C6   C5   C7   C16  negativ
 G80  chir_04  C9   C8   C4   C1   positiv
 G80  chir_05  C10  C9   C17  C11  negativ
 G80  chir_06  C11  O2   C10  C12  negativ
 G80  chir_07  C12  C13  C19  C11  negativ
 G80  chir_08  C14  O3   C5   C13  negativ
 G80  chir_09  C23  S1   C24  C26  positiv

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
 G80  plan-1  O1    0.020
 G80  plan-1  C2    0.020
 G80  plan-1  C3    0.020
 G80  plan-1  C4    0.020
 G80  plan-2  C12   0.020
 G80  plan-2  C19   0.020
 G80  plan-2  C20   0.020
 G80  plan-2  H19   0.020
 G80  plan-2  H201  0.020
 G80  plan-2  H202  0.020
 G80  plan-3  O3    0.020
 G80  plan-3  C21   0.020
 G80  plan-3  O4    0.020
 G80  plan-3  C22   0.020

