# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun May  3 16:03:49 2020
#   Inital geometry file: a 115 line input string
#   Ligand name: (1S,2S,4aR,4bR,7S,9aS,10S,10aR)-2,7-dihydroxy-1-methyl-8-methylidene-13-oxo-1,2,4b,5,6,7,8,9,10,10a-decahydro-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)C=C[C@@]3(OC1=O)[C@@H]4CC[C@]5(O)C[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
 GA3  GA3  '(1S,2S,4aR,4bR,7S,9aS,10S,10aR)-2,7-dihydroxy-1-methyl-8-methylidene-13-oxo-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid'  ligand  46  25  .  2021-08-10  2021-08-10  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_GA3
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
 GA3  O71   O  OC    -1  -0.609  -0.1991   3.5345  -0.8663
 GA3  C7    C  C      0   0.432   0.1026   2.7206   0.0286
 GA3  O72   O  O      0  -0.604   0.3280   2.9875   1.2269
 GA3  C6    C  CH1    0  -0.346   0.1494   1.2342  -0.3746
 GA3  C5    C  CH1    0  -0.223   1.3037   0.4718   0.2966
 GA3  C8    C  CT     0  -0.088  -1.1487   0.4783   0.0502
 GA3  C15   C  CH2    0  -0.479  -2.3445   1.2766   0.5981
 GA3  C16   C  C      0   0.190  -3.5160   0.3397   0.4059
 GA3  C17   C  C2     0  -0.645  -4.7316   0.4805   0.9173
 GA3  C13   C  CT     0   0.197  -3.0725  -0.7982  -0.5105
 GA3  C14   C  CH2    0  -0.449  -1.8233  -0.2116  -1.1448
 GA3  O13   O  OH1    0  -0.678  -4.0147  -1.1550  -1.4920
 GA3  C12   C  CH2    0  -0.450  -2.6318  -2.0203   0.3061
 GA3  C11   C  CH2    0  -0.469  -1.6899  -1.6454   1.4510
 GA3  C9    C  CH1    0  -0.210  -0.6893  -0.5310   1.1254
 GA3  C10   C  CT     0   0.141   0.7250  -0.8675   0.7335
 GA3  O92   O  O2     0  -0.445   0.7819  -1.6609  -0.4894
 GA3  C1    C  C1     0  -0.157   1.6353  -1.5379   1.7199
 GA3  C2    C  C1     0  -0.274   2.9455  -1.4190   1.5300
 GA3  C3    C  CH1    0   0.066   3.5445  -0.5991   0.4077
 GA3  O31   O  OH1    0  -0.659   4.2579   0.4965   0.9392
 GA3  C4    C  CT     0  -0.296   2.4649  -0.0330  -0.5540
 GA3  C18   C  CH3    0  -0.658   3.0592   0.9293  -1.5657
 GA3  C19   C  C      0   0.596   1.8093  -1.2361  -1.2244
 GA3  O91   O  O      0  -0.424   2.1155  -1.7684  -2.2567
 GA3  H6    H  HCH1   0   0.226   0.2285   1.1822  -1.4645
 GA3  H5    H  HCH1   0   0.268   1.6464   1.0331   1.1649
 GA3  H15   H  HCH2   0   0.247  -2.2153   1.5987   1.6328
 GA3  H15A  H  HCH2   0   0.253  -2.4983   2.1792  -0.0027
 GA3  H17   H  H      0   0.234  -4.9852   1.3129   1.5628
 GA3  H17A  H  H      0   0.225  -5.5278  -0.2274   0.7166
 GA3  H14   H  HCH2   0   0.245  -2.0829   0.5550  -1.8834
 GA3  H14A  H  HCH2   0   0.250  -1.2132  -0.9605  -1.6469
 GA3  HO13  H  HOH1   0   0.443  -4.7182  -1.6634  -1.0753
 GA3  H12   H  HCH2   0   0.233  -3.5082  -2.5249   0.7258
 GA3  H12A  H  HCH2   0   0.231  -2.1518  -2.7263  -0.3786
 GA3  H11   H  HCH2   0   0.238  -2.2969  -1.3053   2.2918
 GA3  H11A  H  HCH2   0   0.248  -1.1692  -2.5371   1.8080
 GA3  H9    H  HCH1   0   0.260  -0.5485   0.0497   2.0459
 GA3  H1    H  H      0   0.261   1.2282  -2.1232   2.5369
 GA3  H2    H  H      0   0.263   3.6478  -1.9046   2.2000
 GA3  H3    H  HCH1   0   0.241   4.2216  -1.2388  -0.1768
 GA3  HO31  H  HOH1   0   0.458   5.0432   0.1600   1.3826
 GA3  H18   H  HCH3   0   0.245   3.4107   1.8339  -1.0740
 GA3  H18A  H  HCH3   0   0.236   3.9016   0.4792  -2.0932
 GA3  H18B  H  HCH3   0   0.236   2.3203   1.2221  -2.3111

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
 GA3  O71  C7    deloc   1.247  0.020  1.247
 GA3  C7   O72   deloc   1.248  0.020  1.248
 GA3  C7   C6    single  1.541  0.020  1.541
 GA3  C6   C5    single  1.538  0.020  1.538
 GA3  C6   C8    single  1.561  0.020  1.561
 GA3  C5   C10   single  1.523  0.020  1.523
 GA3  C5   C4    single  1.525  0.020  1.525
 GA3  C8   C15   single  1.539  0.020  1.539
 GA3  C8   C14   single  1.536  0.020  1.536
 GA3  C8   C9    single  1.545  0.020  1.545
 GA3  C15  C16   single  1.512  0.020  1.512
 GA3  C16  C17   double  1.326  0.020  1.326
 GA3  C16  C13   single  1.527  0.020  1.527
 GA3  C13  C14   single  1.519  0.020  1.519
 GA3  C13  O13   single  1.407  0.020  1.407
 GA3  C13  C12   single  1.534  0.020  1.534
 GA3  C12  C11   single  1.529  0.020  1.529
 GA3  C11  C9    single  1.533  0.020  1.533
 GA3  C9   C10   single  1.506  0.020  1.506
 GA3  C10  O92   single  1.459  0.020  1.459
 GA3  C10  C1    single  1.500  0.020  1.500
 GA3  O92  C19   single  1.333  0.020  1.333
 GA3  C1   C2    double  1.329  0.020  1.329
 GA3  C2   C3    single  1.514  0.020  1.514
 GA3  C3   O31   single  1.411  0.020  1.411
 GA3  C3   C4    single  1.553  0.020  1.553
 GA3  C4   C18   single  1.518  0.020  1.518
 GA3  C4   C19   single  1.525  0.020  1.525
 GA3  C19  O91   double  1.201  0.020  1.201
 GA3  C6   H6    single  0.970  0.020  1.090
 GA3  C5   H5    single  0.970  0.020  1.090
 GA3  C15  H15   single  0.970  0.020  1.090
 GA3  C15  H15A  single  0.970  0.020  1.090
 GA3  C17  H17   single  0.930  0.020  1.080
 GA3  C17  H17A  single  0.930  0.020  1.080
 GA3  C14  H14   single  0.970  0.020  1.090
 GA3  C14  H14A  single  0.970  0.020  1.090
 GA3  O13  HO13  single  0.850  0.020  0.980
 GA3  C12  H12   single  0.970  0.020  1.090
 GA3  C12  H12A  single  0.970  0.020  1.090
 GA3  C11  H11   single  0.970  0.020  1.090
 GA3  C11  H11A  single  0.970  0.020  1.090
 GA3  C9   H9    single  0.970  0.020  1.090
 GA3  C1   H1    single  0.930  0.020  1.080
 GA3  C2   H2    single  0.930  0.020  1.080
 GA3  C3   H3    single  0.970  0.020  1.090
 GA3  O31  HO31  single  0.850  0.020  0.980
 GA3  C18  H18   single  0.970  0.020  1.090
 GA3  C18  H18A  single  0.970  0.020  1.090
 GA3  C18  H18B  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
 GA3  C6    C7   O72   116.87  3.000
 GA3  C6    C7   O71   116.70  3.000
 GA3  O72   C7   O71   126.38  3.000
 GA3  H6    C6   C8    107.95  3.000
 GA3  H6    C6   C5    110.92  3.000
 GA3  C8    C6   C5    105.39  3.000
 GA3  H6    C6   C7    107.98  3.000
 GA3  C8    C6   C7    111.75  3.000
 GA3  C5    C6   C7    112.76  3.000
 GA3  H5    C5   C4    112.06  3.000
 GA3  H5    C5   C10   110.12  3.000
 GA3  C4    C5   C10    99.10  3.000
 GA3  H5    C5   C6    109.19  3.000
 GA3  C4    C5   C6    119.48  3.000
 GA3  C10   C5   C6    106.02  3.000
 GA3  C9    C8   C14   112.25  3.000
 GA3  C9    C8   C15   108.80  3.000
 GA3  C14   C8   C15    99.71  3.000
 GA3  C9    C8   C6    104.98  3.000
 GA3  C14   C8   C6    111.78  3.000
 GA3  C15   C8   C6    119.47  3.000
 GA3  H15A  C15  H15   107.07  3.000
 GA3  H15A  C15  C16   109.40  3.000
 GA3  H15   C15  C16   113.27  3.000
 GA3  H15A  C15  C8    109.97  3.000
 GA3  H15   C15  C8    113.50  3.000
 GA3  C16   C15  C8    103.61  3.000
 GA3  C13   C16  C17   125.22  3.000
 GA3  C13   C16  C15   108.24  3.000
 GA3  C17   C16  C15   126.53  3.000
 GA3  H17A  C17  H17   116.11  3.000
 GA3  H17A  C17  C16   122.17  3.000
 GA3  H17   C17  C16   121.72  3.000
 GA3  C12   C13  O13   111.21  3.000
 GA3  C12   C13  C14   107.07  3.000
 GA3  O13   C13  C14   110.95  3.000
 GA3  C12   C13  C16   110.95  3.000
 GA3  O13   C13  C16   114.41  3.000
 GA3  C14   C13  C16   101.64  3.000
 GA3  H14A  C14  H14   107.65  3.000
 GA3  H14A  C14  C13   112.82  3.000
 GA3  H14   C14  C13   110.90  3.000
 GA3  H14A  C14  C8    114.94  3.000
 GA3  H14   C14  C8    108.32  3.000
 GA3  C13   C14  C8    102.11  3.000
 GA3  HO13  O13  C13   108.74  3.000
 GA3  H12A  C12  H12   107.07  3.000
 GA3  H12A  C12  C11   110.89  3.000
 GA3  H12   C12  C11   108.60  3.000
 GA3  H12A  C12  C13   107.87  3.000
 GA3  H12   C12  C13   109.94  3.000
 GA3  C11   C12  C13   112.34  3.000
 GA3  H11A  C11  H11   105.52  3.000
 GA3  H11A  C11  C9    110.59  3.000
 GA3  H11   C11  C9    107.46  3.000
 GA3  H11A  C11  C12   109.76  3.000
 GA3  H11   C11  C12   108.10  3.000
 GA3  C9    C11  C12   114.92  3.000
 GA3  H9    C9   C10   102.48  3.000
 GA3  H9    C9   C11   106.88  3.000
 GA3  C10   C9   C11   120.40  3.000
 GA3  H9    C9   C8    106.04  3.000
 GA3  C10   C9   C8    104.14  3.000
 GA3  C11   C9   C8    115.39  3.000
 GA3  C1    C10  O92   106.52  3.000
 GA3  C1    C10  C9    119.91  3.000
 GA3  O92   C10  C9    112.11  3.000
 GA3  C1    C10  C5    110.55  3.000
 GA3  O92   C10  C5    102.88  3.000
 GA3  C9    C10  C5    103.59  3.000
 GA3  C19   O92  C10   108.60  3.000
 GA3  H1    C1   C2    121.73  3.000
 GA3  H1    C1   C10   120.58  3.000
 GA3  C2    C1   C10   117.66  3.000
 GA3  H2    C2   C3    116.36  3.000
 GA3  H2    C2   C1    120.64  3.000
 GA3  C3    C2   C1    122.99  3.000
 GA3  H3    C3   C4    108.12  3.000
 GA3  H3    C3   O31   109.91  3.000
 GA3  C4    C3   O31   107.56  3.000
 GA3  H3    C3   C2    108.83  3.000
 GA3  C4    C3   C2    112.43  3.000
 GA3  O31   C3   C2    109.96  3.000
 GA3  HO31  O31  C3    108.34  3.000
 GA3  C19   C4   C18   112.06  3.000
 GA3  C19   C4   C3    106.47  3.000
 GA3  C18   C4   C3    111.83  3.000
 GA3  C19   C4   C5    100.31  3.000
 GA3  C18   C4   C5    117.39  3.000
 GA3  C3    C4   C5    107.73  3.000
 GA3  H18B  C18  H18A  107.68  3.000
 GA3  H18B  C18  H18   107.75  3.000
 GA3  H18A  C18  H18   108.18  3.000
 GA3  H18B  C18  C4    111.15  3.000
 GA3  H18A  C18  C4    111.28  3.000
 GA3  H18   C18  C4    110.64  3.000
 GA3  O91   C19  C4    128.15  3.000
 GA3  O91   C19  O92   121.95  3.000
 GA3  C4    C19  O92   109.90  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
 GA3  Var_01  C13  C16  C15  C8   -12.90  30.0  3
 GA3  Var_02  C9   C11  C12  C13  -37.58  30.0  1
 GA3  Var_03  C4   C19  O92  C10   -3.81  30.0  1
 GA3  Var_04  C3   C2   C1   C10    2.55  30.0  2
 GA3  Var_05  H17  C17  C16  C15   -1.30  30.0  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
 GA3  chir_01  C6   C7   C5   C8   negativ
 GA3  chir_02  C5   C4   C10  C6   positiv
 GA3  chir_03  C8   C6   C14  C9   negativ
 GA3  chir_04  C13  C16  C14  C12  negativ
 GA3  chir_05  C9   C10  C11  C8   positiv
 GA3  chir_06  C10  O92  C9   C5   positiv
 GA3  chir_07  C3   O31  C2   C4   negativ
 GA3  chir_08  C4   C19  C3   C5   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
 GA3  plan-1  O71  0.020
 GA3  plan-1  C7   0.020
 GA3  plan-1  O72  0.020
 GA3  plan-1  C6   0.020
 GA3  plan-2  O92  0.020
 GA3  plan-2  C4   0.020
 GA3  plan-2  C19  0.020
 GA3  plan-2  O91  0.020

