# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun May  3 17:41:11 2020
#   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  47  24  .  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_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  -0.422  -1.2053   1.9284   1.4238
 GA4  C2    C  CH2    0  -0.515  -1.3776   1.4780   2.8801
 GA4  C3    C  CH1    0   0.101  -0.2949   0.5059   3.3752
 GA4  O31   O  OH1    0  -0.666   0.9022   1.1668   3.7153
 GA4  C4    C  CT     0  -0.284   0.0786  -0.5597   2.3075
 GA4  C5    C  CH1    0  -0.221   0.5558   0.1828   1.0624
 GA4  C6    C  CH1    0  -0.348   1.1469  -0.6281  -0.1082
 GA4  C7    C  C      0   0.430   2.6371  -0.3192  -0.3441
 GA4  O71   O  O      0  -0.605   2.9808   0.8792  -0.2832
 GA4  O72   O  OC    -1  -0.612   3.3775  -1.2862  -0.6150
 GA4  C8    C  CT     0  -0.078   0.2793  -0.2638  -1.3500
 GA4  C9    C  CH1    0  -0.181  -0.5501   0.9609  -0.9048
 GA4  C10   C  CT     0   0.198  -0.7708   0.7487   0.5738
 GA4  C11   C  CH2    0  -0.462  -1.7349   1.3230  -1.8087
 GA4  C12   C  CH2    0  -0.402  -2.3507   0.1475  -2.5681
 GA4  C13   C  CH1    0  -0.319  -1.2775  -0.8394  -3.0475
 GA4  C14   C  CH2    0  -0.424  -0.6110  -1.4291  -1.8106
 GA4  C15   C  CH2    0  -0.480   0.9770   0.0576  -2.6840
 GA4  C16   C  C      0   0.218  -0.1166  -0.1294  -3.7169
 GA4  C17   C  C2     0  -0.643  -0.0685   0.2507  -4.9883
 GA4  C18   C  CH3    0  -0.662   0.9983  -1.6259   2.8720
 GA4  C19   C  C      0   0.588  -1.2398  -1.1185   1.7985
 GA4  O91   O  O      0  -0.427  -1.8373  -2.0910   2.1765
 GA4  O92   O  O2     0  -0.459  -1.7050  -0.3397   0.8222
 GA4  H11   H  HCH2   0   0.247  -2.1381   2.3671   1.0591
 GA4  H12   H  HCH2   0   0.236  -0.4390   2.7027   1.3437
 GA4  H21   H  HCH2   0   0.242  -2.3545   1.0037   3.0039
 GA4  H22   H  HCH2   0   0.256  -1.4024   2.3459   3.5439
 GA4  H3    H  HCH1   0   0.230  -0.6949  -0.0254   4.2508
 GA4  HO3   H  HOH1   0   0.454   0.7105   1.7853   4.4273
 GA4  H5    H  HCH1   0   0.262   1.2392   0.9937   1.3110
 GA4  H6    H  HCH1   0   0.220   1.0493  -1.7033   0.0696
 GA4  H9    H  HCH1   0   0.247   0.1422   1.8115  -0.9225
 GA4  H111  H  HCH2   0   0.237  -2.5042   1.8463  -1.2349
 GA4  H112  H  HCH2   0   0.231  -1.3780   2.0464  -2.5450
 GA4  H121  H  HCH2   0   0.221  -3.0540  -0.4007  -1.9346
 GA4  H122  H  HCH2   0   0.227  -2.9229   0.5308  -3.4165
 GA4  H13   H  HCH1   0   0.236  -1.7306  -1.5902  -3.6989
 GA4  H141  H  HCH2   0   0.241  -1.3297  -1.7889  -1.0764
 GA4  H142  H  HCH2   0   0.234   0.0317  -2.2760  -2.0759
 GA4  H151  H  HCH2   0   0.243   1.4282   1.0509  -2.7098
 GA4  H152  H  HCH2   0   0.247   1.7779  -0.6674  -2.8634
 GA4  H171  H  H      0   0.225   0.7924   0.7645  -5.4000
 GA4  H172  H  H      0   0.225  -0.8908   0.0603  -5.6682
 GA4  H181  H  HCH3   0   0.235   0.5798  -2.0726   3.7751
 GA4  H182  H  HCH3   0   0.237   1.1650  -2.4286   2.1544
 GA4  H183  H  HCH3   0   0.242   1.9683  -1.2009   3.1250

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  1.534  0.020  1.534
 GA4  C1   C10   single  1.518  0.020  1.518
 GA4  C1   H11   single  0.970  0.020  1.090
 GA4  C1   H12   single  0.970  0.020  1.090
 GA4  C2   C3    single  1.537  0.020  1.537
 GA4  C2   H21   single  0.970  0.020  1.090
 GA4  C2   H22   single  0.970  0.020  1.090
 GA4  C3   O31   single  1.409  0.020  1.409
 GA4  C3   C4    single  1.554  0.020  1.554
 GA4  C3   H3    single  0.970  0.020  1.090
 GA4  O31  HO3   single  0.850  0.020  0.980
 GA4  C4   C5    single  1.526  0.020  1.526
 GA4  C4   C18   single  1.517  0.020  1.517
 GA4  C4   C19   single  1.520  0.020  1.520
 GA4  C5   C6    single  1.542  0.020  1.542
 GA4  C5   C10   single  1.523  0.020  1.523
 GA4  C5   H5    single  0.970  0.020  1.090
 GA4  C6   C7    single  1.540  0.020  1.540
 GA4  C6   C8    single  1.558  0.020  1.558
 GA4  C6   H6    single  0.970  0.020  1.090
 GA4  C7   O71   deloc   1.248  0.020  1.248
 GA4  C7   O72   deloc   1.248  0.020  1.248
 GA4  C8   C9    single  1.545  0.020  1.545
 GA4  C8   C14   single  1.537  0.020  1.537
 GA4  C8   C15   single  1.539  0.020  1.539
 GA4  C9   C10   single  1.510  0.020  1.510
 GA4  C9   C11   single  1.534  0.020  1.534
 GA4  C9   H9    single  0.970  0.020  1.090
 GA4  C10  O92   single  1.456  0.020  1.456
 GA4  C11  C12   single  1.529  0.020  1.529
 GA4  C11  H111  single  0.970  0.020  1.090
 GA4  C11  H112  single  0.970  0.020  1.090
 GA4  C12  C13   single  1.535  0.020  1.535
 GA4  C12  H121  single  0.970  0.020  1.090
 GA4  C12  H122  single  0.970  0.020  1.090
 GA4  C13  C14   single  1.524  0.020  1.524
 GA4  C13  C16   single  1.516  0.020  1.516
 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  1.516  0.020  1.516
 GA4  C15  H151  single  0.970  0.020  1.090
 GA4  C15  H152  single  0.970  0.020  1.090
 GA4  C16  C17   double  1.328  0.020  1.328
 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  1.202  0.020  1.202
 GA4  C19  O92   single  1.333  0.020  1.333

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   106.83  3.000
 GA4  H12   C1   C10   108.01  3.000
 GA4  H11   C1   C10   111.67  3.000
 GA4  H12   C1   C2    110.89  3.000
 GA4  H11   C1   C2    109.79  3.000
 GA4  C10   C1   C2    109.61  3.000
 GA4  H22   C2   H21   104.81  3.000
 GA4  H22   C2   C3    108.82  3.000
 GA4  H21   C2   C3    108.58  3.000
 GA4  H22   C2   C1    110.24  3.000
 GA4  H21   C2   C1    109.59  3.000
 GA4  C3    C2   C1    114.35  3.000
 GA4  H3    C3   C4    107.65  3.000
 GA4  H3    C3   O31   110.10  3.000
 GA4  C4    C3   O31   106.45  3.000
 GA4  H3    C3   C2    107.81  3.000
 GA4  C4    C3   C2    112.44  3.000
 GA4  O31   C3   C2    112.31  3.000
 GA4  HO3   O31  C3    108.10  3.000
 GA4  C19   C4   C18   113.09  3.000
 GA4  C19   C4   C5    100.19  3.000
 GA4  C18   C4   C5    117.12  3.000
 GA4  C19   C4   C3    105.89  3.000
 GA4  C18   C4   C3    111.84  3.000
 GA4  C5    C4   C3    107.58  3.000
 GA4  H5    C5   C10   110.07  3.000
 GA4  H5    C5   C6    108.92  3.000
 GA4  C10   C5   C6    106.61  3.000
 GA4  H5    C5   C4    111.85  3.000
 GA4  C10   C5   C4     99.80  3.000
 GA4  C6    C5   C4    118.91  3.000
 GA4  H6    C6   C8    108.03  3.000
 GA4  H6    C6   C7    107.96  3.000
 GA4  C8    C6   C7    111.71  3.000
 GA4  H6    C6   C5    111.05  3.000
 GA4  C8    C6   C5    105.59  3.000
 GA4  C7    C6   C5    112.44  3.000
 GA4  O72   C7   O71   126.25  3.000
 GA4  O72   C7   C6    116.87  3.000
 GA4  O71   C7   C6    116.84  3.000
 GA4  C15   C8   C14    99.27  3.000
 GA4  C15   C8   C9    109.12  3.000
 GA4  C14   C8   C9    112.11  3.000
 GA4  C15   C8   C6    119.15  3.000
 GA4  C14   C8   C6    112.59  3.000
 GA4  C9    C8   C6    104.75  3.000
 GA4  H9    C9   C11   107.15  3.000
 GA4  H9    C9   C10   102.53  3.000
 GA4  C11   C9   C10   119.83  3.000
 GA4  H9    C9   C8    105.75  3.000
 GA4  C11   C9   C8    115.60  3.000
 GA4  C10   C9   C8    104.44  3.000
 GA4  O92   C10  C9    111.47  3.000
 GA4  O92   C10  C5    103.09  3.000
 GA4  C9    C10  C5    103.83  3.000
 GA4  O92   C10  C1    107.57  3.000
 GA4  C9    C10  C1    118.76  3.000
 GA4  C5    C10  C1    111.01  3.000
 GA4  H112  C11  H111  105.47  3.000
 GA4  H112  C11  C12   107.82  3.000
 GA4  H111  C11  C12   110.20  3.000
 GA4  H112  C11  C9    107.54  3.000
 GA4  H111  C11  C9    110.32  3.000
 GA4  C12   C11  C9    114.99  3.000
 GA4  H122  C12  H121  106.78  3.000
 GA4  H122  C12  C13   110.44  3.000
 GA4  H121  C12  C13   107.96  3.000
 GA4  H122  C12  C11   109.08  3.000
 GA4  H121  C12  C11   110.89  3.000
 GA4  C13   C12  C11   111.58  3.000
 GA4  H13   C13  C16   112.09  3.000
 GA4  H13   C13  C14   113.55  3.000
 GA4  C16   C13  C14   101.81  3.000
 GA4  H13   C13  C12   109.76  3.000
 GA4  C16   C13  C12   111.85  3.000
 GA4  C14   C13  C12   107.53  3.000
 GA4  H142  C14  H141  107.16  3.000
 GA4  H142  C14  C13   111.04  3.000
 GA4  H141  C14  C13   112.75  3.000
 GA4  H142  C14  C8    108.59  3.000
 GA4  H141  C14  C8    115.52  3.000
 GA4  C13   C14  C8    101.72  3.000
 GA4  H152  C15  H151  107.24  3.000
 GA4  H152  C15  C16   109.53  3.000
 GA4  H151  C15  C16   113.23  3.000
 GA4  H152  C15  C8    109.59  3.000
 GA4  H151  C15  C8    113.45  3.000
 GA4  C16   C15  C8    103.75  3.000
 GA4  C17   C16  C15   126.22  3.000
 GA4  C17   C16  C13   125.76  3.000
 GA4  C15   C16  C13   108.01  3.000
 GA4  H172  C17  H171  116.60  3.000
 GA4  H172  C17  C16   121.52  3.000
 GA4  H171  C17  C16   121.88  3.000
 GA4  H183  C18  H182  107.72  3.000
 GA4  H183  C18  H181  108.01  3.000
 GA4  H182  C18  H181  107.59  3.000
 GA4  H183  C18  C4    110.62  3.000
 GA4  H182  C18  C4    111.44  3.000
 GA4  H181  C18  C4    111.30  3.000
 GA4  O92   C19  O91   121.97  3.000
 GA4  O92   C19  C4    109.47  3.000
 GA4  O91   C19  C4    128.55  3.000
 GA4  C19   O92  C10   109.75  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  Var_01  C10   C1   C2   C3    40.63  30.0  1
 GA4  Var_02  C13   C16  C15  C8   -12.81  30.0  3
 GA4  Var_03  C13   C12  C11  C9   -38.10  30.0  1
 GA4  Var_04  H171  C17  C16  C13  179.38  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
 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-2  C4   0.020
 GA4  plan-2  C19  0.020
 GA4  plan-2  O91  0.020
 GA4  plan-2  O92  0.020

