# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Jul 30 15:23:29 2021
#   Inital geometry file: a 113 line input string
#   Ligand name: (1S,2S,4aR,4bR,7R,9aR,10S,10aR)-2-hydroxy-1-methyl-8-methylidene-13-oxododecahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@]12[C@@H](O)CC[C@@]3(OC1=O)[C@@H]4CC[C@@H]5C[C@]4(CC5=C)[C@H]([C@H]23)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
 GA4  GA4  '(1S,2S,4aR,4bR,7R,9aR,10S,10aR)-2-hydroxy-1-methyl-8-methylidene-13-oxododecahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid'  ligand  48  24  .  2021-08-10  2022-11-17
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_GA4
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
 GA4  C1    C  CH2   0  -0.426  50.5327  23.9899  -2.5522
 GA4  C2    C  CH2   0  -0.506  49.7527  24.6204  -1.3930
 GA4  C3    C  CH1   0   0.096  50.5342  25.6855  -0.6214
 GA4  O31   O  OH1   0  -0.659  50.4863  26.8861  -1.3530
 GA4  C4    C  CR5   0  -0.294  52.0122  25.2479  -0.3688
 GA4  C5    C  CR15  0  -0.225  52.6690  25.0186  -1.7260
 GA4  C6    C  CH1   0  -0.377  54.1493  24.6460  -1.7334
 GA4  C7    C  C     0   0.559  55.0636  25.8382  -1.8180
 GA4  O71   O  O     0  -0.434  54.7411  26.9338  -2.2058
 GA4  O72   O  OH1   0  -0.588  56.2987  25.5405  -1.4308
 GA4  C8    C  CT    0  -0.075  54.3099  23.6721  -2.9333
 GA4  C9    C  CH1   0  -0.207  52.8783  23.0804  -3.1754
 GA4  C10   C  CR5   0   0.222  51.9730  23.7327  -2.1449
 GA4  C11   C  CH2   0  -0.454  52.8643  21.5563  -3.2222
 GA4  C12   C  CH2   0  -0.410  53.9374  21.0206  -4.1768
 GA4  C13   C  CH1   0  -0.321  55.2338  21.8622  -4.1126
 GA4  C14   C  CH2   0  -0.429  55.3255  22.5436  -2.7435
 GA4  C15   C  CH2   0  -0.493  54.8107  24.2786  -4.2541
 GA4  C16   C  C     0   0.210  55.1685  23.0484  -5.0571
 GA4  C17   C  C2    0  -0.628  55.3893  23.0066  -6.3651
 GA4  C18   C  CH3   0  -0.685  52.7258  26.1851   0.5875
 GA4  C19   C  CR5   0   0.576  51.9603  23.8168   0.1366
 GA4  O91   O  O     0  -0.416  51.9101  23.4267   1.2713
 GA4  O92   O  O     0  -0.462  51.9654  22.9758  -0.9012
 GA4  H11   H  HCH2  0   0.256  50.0444  23.0652  -2.8694
 GA4  H12   H  HCH2  0   0.244  50.5439  24.6526  -3.4203
 GA4  H21   H  HCH2  0   0.265  48.8236  25.0611  -1.7585
 GA4  H22   H  HCH2  0   0.252  49.4451  23.8408  -0.6924
 GA4  H3    H  HCH1  0   0.241  50.0590  25.8189   0.3600
 GA4  HO3   H  HOH1  0   0.455  50.8332  27.5989  -0.8076
 GA4  H5    H  HCR5  0   0.282  52.4774  25.8285  -2.4300
 GA4  H6    H  HCH1  0   0.290  54.4178  24.0960  -0.8242
 GA4  HO7   H  HOH1  0   0.482  56.8753  26.3135  -1.5304
 GA4  H9    H  HCH1  0   0.257  52.5194  23.4457  -4.1451
 GA4  H111  H  HCH2  0   0.234  53.0414  21.1548  -2.2235
 GA4  H112  H  HCH2  0   0.244  51.8783  21.1974  -3.5258
 GA4  H121  H  HCH2  0   0.235  54.1614  19.9856  -3.9097
 GA4  H122  H  HCH2  0   0.229  53.5667  21.0038  -5.2038
 GA4  H13   H  HCH1  0   0.249  56.0935  21.2274  -4.3345
 GA4  H141  H  HCH2  0   0.252  56.3244  22.9530  -2.5721
 GA4  H142  H  HCH2  0   0.246  55.0986  21.8775  -1.9087
 GA4  H151  H  HCH2  0   0.257  54.0791  24.9196  -4.7507
 GA4  H152  H  HCH2  0   0.256  55.7163  24.8759  -4.1018
 GA4  H171  H  H     0   0.230  55.6630  22.0834  -6.8624
 GA4  H172  H  H     0   0.231  55.3054  23.8882  -6.9890
 GA4  H181  H  HCH3  0   0.247  53.7177  25.8170   0.8508
 GA4  H182  H  HCH3  0   0.242  52.8582  27.1713   0.1423
 GA4  H183  H  HCH3  0   0.252  52.1638  26.3054   1.5141

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
 GA4  C1   C2    single  1.533  0.020  1.533
 GA4  C1   C10   single  1.519  0.020  1.519
 GA4  C1   H11   single  0.970  0.020  1.090
 GA4  C1   H12   single  0.970  0.020  1.090
 GA4  C2   C3    single  1.530  0.020  1.530
 GA4  C2   H21   single  0.970  0.020  1.090
 GA4  C2   H22   single  0.970  0.020  1.090
 GA4  C3   O31   single  1.407  0.020  1.407
 GA4  C3   C4    single  1.562  0.020  1.562
 GA4  C3   H3    single  0.970  0.020  1.090
 GA4  O31  HO3   single  0.850  0.020  0.980
 GA4  C4   C5    single  1.525  0.020  1.525
 GA4  C4   C18   single  1.517  0.020  1.517
 GA4  C4   C19   single  1.519  0.020  1.519
 GA4  C5   C6    single  1.526  0.020  1.526
 GA4  C5   C10   single  1.521  0.020  1.521
 GA4  C5   H5    single  0.970  0.020  1.090
 GA4  C6   C7    single  1.505  0.020  1.505
 GA4  C6   C8    single  1.554  0.020  1.554
 GA4  C6   H6    single  0.970  0.020  1.090
 GA4  C7   O71   double  1.206  0.020  1.206
 GA4  C7   O72   single  1.328  0.020  1.328
 GA4  O72  HO7   single  0.850  0.020  0.980
 GA4  C8   C9    single  1.568  0.020  1.568
 GA4  C8   C14   single  1.530  0.020  1.530
 GA4  C8   C15   single  1.537  0.020  1.537
 GA4  C9   C10   single  1.519  0.020  1.519
 GA4  C9   C11   single  1.525  0.020  1.525
 GA4  C9   H9    single  0.970  0.020  1.090
 GA4  C10  O92   single  1.456  0.020  1.456
 GA4  C11  C12   single  1.533  0.020  1.533
 GA4  C11  H111  single  0.970  0.020  1.090
 GA4  C11  H112  single  0.970  0.020  1.090
 GA4  C12  C13   single  1.547  0.020  1.547
 GA4  C12  H121  single  0.970  0.020  1.090
 GA4  C12  H122  single  0.970  0.020  1.090
 GA4  C13  C14   single  1.532  0.020  1.532
 GA4  C13  C16   single  1.518  0.020  1.518
 GA4  C13  H13   single  0.970  0.020  1.090
 GA4  C14  H141  single  0.970  0.020  1.090
 GA4  C14  H142  single  0.970  0.020  1.090
 GA4  C15  C16   single  1.512  0.020  1.512
 GA4  C15  H151  single  0.970  0.020  1.090
 GA4  C15  H152  single  0.970  0.020  1.090
 GA4  C16  C17   double  1.327  0.020  1.327
 GA4  C17  H171  single  0.930  0.020  1.080
 GA4  C17  H172  single  0.930  0.020  1.080
 GA4  C18  H181  single  0.970  0.020  1.090
 GA4  C18  H182  single  0.970  0.020  1.090
 GA4  C18  H183  single  0.970  0.020  1.090
 GA4  C19  O91   double  1.201  0.020  1.201
 GA4  C19  O92   single  1.336  0.020  1.336

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
 GA4  H12   C1   H11   106.69  3.000
 GA4  H12   C1   C10   107.83  3.000
 GA4  H11   C1   C10   111.00  3.000
 GA4  H12   C1   C2    110.90  3.000
 GA4  H11   C1   C2    109.89  3.000
 GA4  C10   C1   C2    110.45  3.000
 GA4  H22   C2   H21   105.26  3.000
 GA4  H22   C2   C3    108.50  3.000
 GA4  H21   C2   C3    108.83  3.000
 GA4  H22   C2   C1    109.56  3.000
 GA4  H21   C2   C1    110.24  3.000
 GA4  C3    C2   C1    114.07  3.000
 GA4  H3    C3   C4    107.39  3.000
 GA4  H3    C3   O31   110.25  3.000
 GA4  C4    C3   O31   110.82  3.000
 GA4  H3    C3   C2    108.31  3.000
 GA4  C4    C3   C2    111.71  3.000
 GA4  O31   C3   C2    108.33  3.000
 GA4  HO3   O31  C3    108.98  3.000
 GA4  C19   C4   C18   112.85  3.000
 GA4  C19   C4   C5     99.74  3.000
 GA4  C18   C4   C5    116.82  3.000
 GA4  C19   C4   C3    106.59  3.000
 GA4  C18   C4   C3    111.96  3.000
 GA4  C5    C4   C3    107.80  3.000
 GA4  H5    C5   C10   111.71  3.000
 GA4  H5    C5   C6    110.41  3.000
 GA4  C10   C5   C6    103.65  3.000
 GA4  H5    C5   C4    112.79  3.000
 GA4  C10   C5   C4    100.08  3.000
 GA4  C6    C5   C4    117.30  3.000
 GA4  H6    C6   C8    107.50  3.000
 GA4  H6    C6   C7    107.18  3.000
 GA4  C8    C6   C7    112.98  3.000
 GA4  H6    C6   C5    110.86  3.000
 GA4  C8    C6   C5    104.89  3.000
 GA4  C7    C6   C5    113.33  3.000
 GA4  O72   C7   O71   123.09  3.000
 GA4  O72   C7   C6    111.78  3.000
 GA4  O71   C7   C6    125.12  3.000
 GA4  HO7   O72  C7    110.15  3.000
 GA4  C15   C8   C14   100.45  3.000
 GA4  C15   C8   C9    108.28  3.000
 GA4  C14   C8   C9    110.30  3.000
 GA4  C15   C8   C6    116.74  3.000
 GA4  C14   C8   C6    115.79  3.000
 GA4  C9    C8   C6    105.15  3.000
 GA4  H9    C9   C11   107.62  3.000
 GA4  H9    C9   C10   105.17  3.000
 GA4  C11   C9   C10   116.40  3.000
 GA4  H9    C9   C8    108.04  3.000
 GA4  C11   C9   C8    112.98  3.000
 GA4  C10   C9   C8    106.11  3.000
 GA4  O92   C10  C9    111.07  3.000
 GA4  O92   C10  C5    101.92  3.000
 GA4  C9    C10  C5    106.09  3.000
 GA4  O92   C10  C1    108.19  3.000
 GA4  C9    C10  C1    117.13  3.000
 GA4  C5    C10  C1    111.38  3.000
 GA4  H112  C11  H111  106.27  3.000
 GA4  H112  C11  C12   110.12  3.000
 GA4  H111  C11  C12   109.14  3.000
 GA4  H112  C11  C9    110.20  3.000
 GA4  H111  C11  C9    109.77  3.000
 GA4  C12   C11  C9    111.22  3.000
 GA4  H122  C12  H121  106.56  3.000
 GA4  H122  C12  C13   109.39  3.000
 GA4  H121  C12  C13   109.49  3.000
 GA4  H122  C12  C11   110.69  3.000
 GA4  H121  C12  C11   108.81  3.000
 GA4  C13   C12  C11   111.76  3.000
 GA4  H13   C13  C16   111.22  3.000
 GA4  H13   C13  C14   113.15  3.000
 GA4  C16   C13  C14   102.18  3.000
 GA4  H13   C13  C12   109.59  3.000
 GA4  C16   C13  C12   111.30  3.000
 GA4  C14   C13  C12   109.23  3.000
 GA4  H142  C14  H141  107.37  3.000
 GA4  H142  C14  C13   113.54  3.000
 GA4  H141  C14  C13   111.19  3.000
 GA4  H142  C14  C8    114.01  3.000
 GA4  H141  C14  C8    110.48  3.000
 GA4  C13   C14  C8    100.22  3.000
 GA4  H152  C15  H151  107.28  3.000
 GA4  H152  C15  C16   108.77  3.000
 GA4  H151  C15  C16   113.24  3.000
 GA4  H152  C15  C8    111.40  3.000
 GA4  H151  C15  C8    113.83  3.000
 GA4  C16   C15  C8    102.26  3.000
 GA4  C17   C16  C15   126.04  3.000
 GA4  C17   C16  C13   125.56  3.000
 GA4  C15   C16  C13   108.40  3.000
 GA4  H172  C17  H171  116.65  3.000
 GA4  H172  C17  C16   121.94  3.000
 GA4  H171  C17  C16   121.41  3.000
 GA4  H183  C18  H182  108.05  3.000
 GA4  H183  C18  H181  107.51  3.000
 GA4  H182  C18  H181  107.07  3.000
 GA4  H183  C18  C4    111.18  3.000
 GA4  H182  C18  C4    111.01  3.000
 GA4  H181  C18  C4    111.81  3.000
 GA4  O92   C19  O91   121.99  3.000
 GA4  O92   C19  C4    109.55  3.000
 GA4  O91   C19  C4    128.46  3.000
 GA4  C19   O92  C10   109.66  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
 GA4  CONST_01  HO7   O72  C7   C6   180.00   0.0  0
 GA4  Var_01    C10   C1   C2   C3    41.14  30.0  1
 GA4  Var_02    C13   C16  C15  C8   -14.90  30.0  3
 GA4  Var_03    C13   C12  C11  C9    37.49  30.0  1
 GA4  Var_04    H171  C17  C16  C13   -1.34   0.0  2

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
 GA4  chir_01  C3   C2   O31  C4   positiv
 GA4  chir_02  C4   C18  C5   C3   positiv
 GA4  chir_03  C5   C4   C6   C10  negativ
 GA4  chir_04  C6   C5   C7   C8   positiv
 GA4  chir_05  C8   C14  C9   C6   negativ
 GA4  chir_06  C9   C11  C10  C8   negativ
 GA4  chir_07  C10  C9   C5   C1   negativ
 GA4  chir_08  C13  C12  C14  C16  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
 GA4  plan-1  C6    0.020
 GA4  plan-1  C7    0.020
 GA4  plan-1  O71   0.020
 GA4  plan-1  O72   0.020
 GA4  plan-1  HO7   0.020
 GA4  plan-2  C4    0.020
 GA4  plan-2  C19   0.020
 GA4  plan-2  O91   0.020
 GA4  plan-2  O92   0.020
 GA4  plan-3  C13   0.020
 GA4  plan-3  C15   0.020
 GA4  plan-3  C16   0.020
 GA4  plan-3  C17   0.020
 GA4  plan-3  H171  0.020
 GA4  plan-3  H172  0.020

