# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Jul 29 23:01:10 2022
#   Inital geometry file: a 131 line input string
#   Ligand name: (2~{R},4~{S})-6-ethyl-2-(2-hydroxyethyl)-2,8-dimethyl-4-(2-methylprop-1-enyl)-3,4-dihydropyrano[3,2-c][1,8]naphthyridin-5-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCN1C(=O)C2=C(O[C@@](C)(CCO)C[C@H]2C=C(C)C)c3ccc(C)nc13
#
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
 8GO  8GO  "(2R,4S)-6-ethyl-2-(2-hydroxyethyl)-2,8-dimethyl-4-(2-methylprop-1-enyl)-3,4-dihydropyrano[3,2-c][1,8]naphthyridin-5-one"
  ligand  54  26  .  2022-09-16  2022-09-16
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_8GO
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
 8GO  C1   C  CR16  0  -0.344  -22.3211  -1.7025  -22.4503
 8GO  C4   C  CR66  0   0.488  -24.0995  -3.4034  -23.6126
 8GO  C5   C  CR66  0  -0.157  -23.3134  -2.5907  -24.4418
 8GO  C6   C  CR16  0  -0.172  -22.4114  -1.7239  -23.8223
 8GO  N7   N  NR6   0  -0.592  -25.0207  -4.2600  -24.1637
 8GO  C13  C  CH2   0  -0.313  -25.8683  -5.0688  -23.2871
 8GO  C14  C  CR16  0  -0.350  -24.5238  -3.7180  -27.8905
 8GO  C15  C  C1    0  -0.195  -24.4770  -5.1566  -28.3339
 8GO  C16  C  C     0   0.071  -25.1449  -5.7084  -29.3477
 8GO  C17  C  CH3   0  -0.721  -26.1493  -4.9922  -30.2007
 8GO  C18  C  CH3   0  -0.705  -24.9244  -7.1457  -29.7215
 8GO  C20  C  CR6   0   0.207  -23.0547  -1.6340  -27.9661
 8GO  C21  C  CH2   0  -0.479  -21.7675  -1.0348  -28.5416
 8GO  C22  C  CH2   0  -0.171  -21.6837  -0.8797  -30.0490
 8GO  C23  C  CH3   0  -0.662  -24.2279  -0.6629  -27.9999
 8GO  C19  C  C     0  -0.459  -23.3867  -2.9748  -28.6025
 8GO  C9   C  CR66  0  -0.201  -24.3712  -3.5658  -26.4001
 8GO  C8   C  CR6   0   0.542  -25.2504  -4.3245  -25.5324
 8GO  O12  O  O     0  -0.477  -26.1697  -5.0077  -25.9662
 8GO  C25  C  CH3   0  -0.665  -27.1129  -4.3286  -22.8300
 8GO  N3   N  N     0  -0.470  -24.0084  -3.3738  -22.2862
 8GO  C2   C  CR6   0   0.252  -23.1459  -2.5544  -21.7076
 8GO  C24  C  CH3   0  -0.729  -23.0798  -2.5591  -20.2121
 8GO  C10  C  CR66  0   0.469  -23.4808  -2.6901  -25.8657
 8GO  O11  O  O     0  -0.482  -22.7146  -1.8667  -26.5744
 8GO  O26  O  OH1   0  -0.660  -22.6135   0.0738  -30.5124
 8GO  H1   H  HCR6  0   0.264  -21.6298  -1.0382  -21.9495
 8GO  H2   H  HCR6  0   0.269  -21.7875  -1.0733  -24.4197
 8GO  H3   H  HCH2  0   0.257  -26.1386  -5.9695  -23.8313
 8GO  H4   H  HCH2  0   0.257  -25.2709  -5.3700  -22.4310
 8GO  H5   H  HCR6  0   0.267  -25.4777  -3.2709  -28.1866
 8GO  H6   H  H     0   0.222  -23.7561  -5.7754  -27.8041
 8GO  H7   H  HCH3  0   0.240  -26.3123  -3.9559  -29.9106
 8GO  H8   H  HCH3  0   0.234  -25.8318  -4.9960  -31.2465
 8GO  H9   H  HCH3  0   0.234  -27.1149  -5.5040  -30.1706
 8GO  H10  H  HCH3  0   0.235  -24.1827  -7.6259  -29.0835
 8GO  H11  H  HCH3  0   0.228  -25.8535  -7.7177  -29.6487
 8GO  H12  H  HCH3  0   0.228  -24.5872  -7.2347  -30.7571
 8GO  H13  H  HCH2  0   0.246  -20.9387  -1.6902  -28.2582
 8GO  H14  H  HCH2  0   0.243  -21.5755  -0.0679  -28.0654
 8GO  H15  H  HCH2  0   0.203  -21.8329  -1.8531  -30.5316
 8GO  H16  H  HCH2  0   0.210  -20.6560  -0.5753  -30.2847
 8GO  H17  H  HCH3  0   0.237  -23.9458   0.2959  -27.5637
 8GO  H18  H  HCH3  0   0.246  -24.5422  -0.4851  -29.0256
 8GO  H19  H  HCH3  0   0.237  -25.0896  -1.0408  -27.4473
 8GO  H20  H  H     0   0.261  -23.6633  -2.8328  -29.6481
 8GO  H21  H  H     0   0.248  -22.4848  -3.5960  -28.5977
 8GO  H22  H  HCH3  0   0.234  -27.7090  -4.9733  -22.1840
 8GO  H23  H  HCH3  0   0.230  -26.8550  -3.4332  -22.2650
 8GO  H24  H  HCH3  0   0.231  -27.7342  -4.0350  -23.6757
 8GO  H25  H  HCH3  0   0.252  -23.7878  -3.2700  -19.7926
 8GO  H26  H  HCH3  0   0.255  -22.0783  -2.8225  -19.8690
 8GO  H27  H  HCH3  0   0.255  -23.3028  -1.5691  -19.8112
 8GO  H28  H  HOH1  0   0.453  -22.5601   0.0997  -31.4720

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
 8GO  O26  C22  single    1.410  0.020  1.410
 8GO  C17  C16  single    1.500  0.020  1.500
 8GO  C22  C21  single    1.518  0.020  1.518
 8GO  C18  C16  single    1.501  0.020  1.501
 8GO  C16  C15  double    1.334  0.020  1.334
 8GO  C19  C20  single    1.521  0.020  1.521
 8GO  C19  C14  single    1.534  0.020  1.534
 8GO  C23  C20  single    1.523  0.020  1.523
 8GO  C15  C14  single    1.506  0.020  1.506
 8GO  C21  C20  single    1.532  0.020  1.532
 8GO  C20  O11  single    1.451  0.020  1.451
 8GO  C14  C9   single    1.506  0.020  1.506
 8GO  O11  C10  single    1.329  0.020  1.329
 8GO  C9   C10  double    1.358  0.020  1.358
 8GO  C9   C8   single    1.450  0.020  1.450
 8GO  O12  C8   double    1.225  0.020  1.225
 8GO  C10  C5   single    1.437  0.020  1.437
 8GO  C8   N7   single    1.389  0.020  1.389
 8GO  C5   C6   aromatic  1.396  0.020  1.396
 8GO  C5   C4   aromatic  1.402  0.020  1.402
 8GO  N7   C4   single    1.373  0.020  1.373
 8GO  N7   C13  single    1.463  0.020  1.463
 8GO  C6   C1   aromatic  1.375  0.020  1.375
 8GO  C4   N3   aromatic  1.330  0.020  1.330
 8GO  C13  C25  single    1.519  0.020  1.519
 8GO  C1   C2   aromatic  1.399  0.020  1.399
 8GO  N3   C2   aromatic  1.323  0.020  1.323
 8GO  C2   C24  single    1.497  0.020  1.497
 8GO  C1   H1   single    0.930  0.020  1.080
 8GO  C6   H2   single    0.930  0.020  1.080
 8GO  C13  H3   single    0.970  0.020  1.090
 8GO  C13  H4   single    0.970  0.020  1.090
 8GO  C14  H5   single    0.970  0.020  1.090
 8GO  C15  H6   single    0.930  0.020  1.080
 8GO  C17  H7   single    0.970  0.020  1.090
 8GO  C17  H8   single    0.970  0.020  1.090
 8GO  C17  H9   single    0.970  0.020  1.090
 8GO  C18  H10  single    0.970  0.020  1.090
 8GO  C18  H11  single    0.970  0.020  1.090
 8GO  C18  H12  single    0.970  0.020  1.090
 8GO  C21  H13  single    0.970  0.020  1.090
 8GO  C21  H14  single    0.970  0.020  1.090
 8GO  C22  H15  single    0.970  0.020  1.090
 8GO  C22  H16  single    0.970  0.020  1.090
 8GO  C23  H17  single    0.970  0.020  1.090
 8GO  C23  H18  single    0.970  0.020  1.090
 8GO  C23  H19  single    0.970  0.020  1.090
 8GO  C19  H20  single    0.970  0.020  1.090
 8GO  C19  H21  single    0.970  0.020  1.090
 8GO  C25  H22  single    0.970  0.020  1.090
 8GO  C25  H23  single    0.970  0.020  1.090
 8GO  C25  H24  single    0.970  0.020  1.090
 8GO  C24  H25  single    0.970  0.020  1.090
 8GO  C24  H26  single    0.970  0.020  1.090
 8GO  C24  H27  single    0.970  0.020  1.090
 8GO  O26  H28  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
 8GO  H1   C1   C2   120.33  3.000
 8GO  H1   C1   C6   120.89  3.000
 8GO  C2   C1   C6   118.78  3.000
 8GO  N3   C4   N7   117.39  3.000
 8GO  N3   C4   C5   122.58  3.000
 8GO  N7   C4   C5   120.02  3.000
 8GO  C10  C5   C6   123.91  3.000
 8GO  C6   C5   C4   117.37  3.000
 8GO  C10  C5   C4   118.72  3.000
 8GO  H2   C6   C5   120.08  3.000
 8GO  H2   C6   C1   120.26  3.000
 8GO  C5   C6   C1   119.66  3.000
 8GO  C8   N7   C13  117.95  3.000
 8GO  C13  N7   C4   119.53  3.000
 8GO  C8   N7   C4   122.36  3.000
 8GO  H4   C13  H3   107.55  3.000
 8GO  H4   C13  C25  110.40  3.000
 8GO  H3   C13  C25  110.55  3.000
 8GO  H4   C13  N7   107.87  3.000
 8GO  H3   C13  N7   107.60  3.000
 8GO  C25  C13  N7   112.69  3.000
 8GO  H5   C14  C9   108.35  3.000
 8GO  H5   C14  C19  108.83  3.000
 8GO  C9   C14  C19  109.60  3.000
 8GO  H5   C14  C15  109.73  3.000
 8GO  C9   C14  C15  112.63  3.000
 8GO  C19  C14  C15  107.64  3.000
 8GO  H6   C15  C16  117.83  3.000
 8GO  H6   C15  C14  114.87  3.000
 8GO  C16  C15  C14  127.12  3.000
 8GO  C18  C16  C17  114.45  3.000
 8GO  C18  C16  C15  120.78  3.000
 8GO  C17  C16  C15  124.77  3.000
 8GO  H9   C17  H8   106.34  3.000
 8GO  H9   C17  H7   107.82  3.000
 8GO  H8   C17  H7   107.57  3.000
 8GO  H9   C17  C16  110.63  3.000
 8GO  H8   C17  C16  110.37  3.000
 8GO  H7   C17  C16  113.78  3.000
 8GO  H12  C18  H11  106.42  3.000
 8GO  H12  C18  H10  107.99  3.000
 8GO  H11  C18  H10  107.98  3.000
 8GO  H12  C18  C16  111.06  3.000
 8GO  H11  C18  C16  111.07  3.000
 8GO  H10  C18  C16  112.09  3.000
 8GO  O11  C20  C19  108.12  3.000
 8GO  O11  C20  C23  107.70  3.000
 8GO  C19  C20  C23  112.61  3.000
 8GO  O11  C20  C21  103.06  3.000
 8GO  C23  C20  C21  112.92  3.000
 8GO  C19  C20  C21  111.78  3.000
 8GO  H14  C21  H13  106.48  3.000
 8GO  H14  C21  C22  109.40  3.000
 8GO  H13  C21  C22  106.07  3.000
 8GO  H14  C21  C20  109.23  3.000
 8GO  H13  C21  C20  107.75  3.000
 8GO  C22  C21  C20  117.35  3.000
 8GO  H16  C22  H15  106.20  3.000
 8GO  H16  C22  O26  111.06  3.000
 8GO  H15  C22  O26  111.46  3.000
 8GO  H16  C22  C21  107.06  3.000
 8GO  H15  C22  C21  109.81  3.000
 8GO  O26  C22  C21  111.05  3.000
 8GO  H19  C23  H18  107.83  3.000
 8GO  H19  C23  H17  107.83  3.000
 8GO  H18  C23  H17  107.96  3.000
 8GO  H19  C23  C20  112.10  3.000
 8GO  H18  C23  C20  110.35  3.000
 8GO  H17  C23  C20  110.63  3.000
 8GO  H21  C19  H20  106.67  3.000
 8GO  H21  C19  C20  108.57  3.000
 8GO  H20  C19  C20  109.98  3.000
 8GO  H21  C19  C14  109.49  3.000
 8GO  H20  C19  C14  108.67  3.000
 8GO  C20  C19  C14  113.25  3.000
 8GO  C10  C9   C8   119.97  3.000
 8GO  C8   C9   C14  118.56  3.000
 8GO  C10  C9   C14  121.39  3.000
 8GO  O12  C8   C9   122.36  3.000
 8GO  O12  C8   N7   119.93  3.000
 8GO  C9   C8   N7   117.72  3.000
 8GO  H24  C25  H23  108.42  3.000
 8GO  H24  C25  H22  107.91  3.000
 8GO  H23  C25  H22  107.94  3.000
 8GO  H24  C25  C13  111.42  3.000
 8GO  H23  C25  C13  111.26  3.000
 8GO  H22  C25  C13  109.77  3.000
 8GO  C2   N3   C4   119.65  3.000
 8GO  C24  C2   N3   117.63  3.000
 8GO  C24  C2   C1   120.41  3.000
 8GO  N3   C2   C1   121.96  3.000
 8GO  H27  C24  H26  106.92  3.000
 8GO  H27  C24  H25  108.57  3.000
 8GO  H26  C24  H25  108.57  3.000
 8GO  H27  C24  C2   110.81  3.000
 8GO  H26  C24  C2   110.82  3.000
 8GO  H25  C24  C2   111.02  3.000
 8GO  O11  C10  C9   124.57  3.000
 8GO  C9   C10  C5   120.71  3.000
 8GO  O11  C10  C5   114.72  3.000
 8GO  C10  O11  C20  118.38  3.000
 8GO  H28  O26  C22  108.03  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
 8GO  CONST_01  C4   C5   C6   C1      0.00   0.0  0
 8GO  CONST_02  C4   N3   C2   C1      0.00   0.0  0
 8GO  CONST_03  C2   C1   C6   C5      0.00   0.0  0
 8GO  CONST_04  C2   N3   C4   C5      0.00   0.0  0
 8GO  CONST_05  N3   C4   C5   C6      0.00   0.0  0
 8GO  CONST_06  N3   C2   C1   C6      0.00   0.0  0
 8GO  CONST_07  C9   C8   N7   C4      0.00   0.0  0
 8GO  CONST_08  C24  C2   N3   C4    180.00   0.0  0
 8GO  CONST_09  C24  C2   C1   C6    180.00   0.0  0
 8GO  CONST_10  O12  C8   N7   C4    180.00   0.0  0
 8GO  CONST_11  C9   C8   N7   C13   180.00   0.0  0
 8GO  CONST_12  H2   C6   C5   C4    180.00   0.0  0
 8GO  CONST_13  H1   C1   C6   C5    180.00   0.0  0
 8GO  CONST_14  H1   C1   C2   N3    180.00   0.0  0
 8GO  CONST_15  H2   C6   C1   C2    180.00   0.0  0
 8GO  CONST_16  H2   C6   C5   C10     0.00   0.0  0
 8GO  CONST_17  O12  C8   N7   C13     0.00   0.0  0
 8GO  CONST_18  C17  C16  C15  C14     0.00   0.0  0
 8GO  CONST_19  C18  C16  C15  C14   180.00   0.0  0
 8GO  CONST_20  H6   C15  C16  C17   180.00   0.0  0
 8GO  CONST_21  H6   C15  C16  C18     0.00   0.0  0
 8GO  Var_01    O11  C10  C5   C4    178.79  30.0  1
 8GO  Var_02    C9   C10  C5   C4     -0.81  30.0  1
 8GO  Var_03    C20  O11  C10  C5   -163.80  30.0  1
 8GO  Var_04    C14  C9   C10  C5   -177.77  30.0  1
 8GO  Var_05    C8   C9   C10  C5      5.61  30.0  1
 8GO  Var_06    C8   N7   C4   C5     -2.51  30.0  1
 8GO  Var_07    O11  C10  C5   C6     -0.97  30.0  1
 8GO  Var_08    C9   C10  C5   C6    179.43  30.0  1
 8GO  Var_09    C14  C9   C8   N7    174.60  30.0  1
 8GO  Var_10    C10  C9   C8   N7     -8.69  30.0  1
 8GO  Var_11    O11  C10  C9   C14     2.67  30.0  1
 8GO  Var_12    C9   C10  O11  C20    15.78  30.0  1
 8GO  Var_13    O11  C10  C9   C8   -173.94  30.0  1
 8GO  Var_14    N3   C4   N7   C8    176.62  30.0  1
 8GO  Var_15    C13  N7   C4   C5   -177.85  30.0  1
 8GO  Var_16    N3   C4   N7   C13     1.27  30.0  1
 8GO  Var_17    O12  C8   C9   C14    -5.29  30.0  1
 8GO  Var_18    C10  C9   C8   O12   171.42  30.0  1
 8GO  Var_19    C25  C13  N7   C4     85.35  30.0  3
 8GO  Var_20    C25  C13  N7   C8    -90.20  30.0  3
 8GO  Var_21    H25  C24  C2   C1    179.59  30.0  2
 8GO  Var_22    H26  C24  C2   C1    -59.66  30.0  2
 8GO  Var_23    H27  C24  C2   C1     58.87  30.0  2
 8GO  Var_24    H3   C13  N7   C4   -152.54  30.0  3
 8GO  Var_25    H4   C13  N7   C4    -36.77  30.0  3
 8GO  Var_26    H3   C13  N7   C8     31.92  30.0  3
 8GO  Var_27    H4   C13  N7   C8    147.68  30.0  3
 8GO  Var_28    H25  C24  C2   N3     -0.13  30.0  2
 8GO  Var_29    H26  C24  C2   N3    120.61  30.0  2
 8GO  Var_30    H27  C24  C2   N3   -120.85  30.0  2
 8GO  Var_31    O26  C22  C21  C20    66.46  30.0  1
 8GO  Var_32    H22  C25  C13  N7    179.86  30.0  3
 8GO  Var_33    H23  C25  C13  N7    -60.73  30.0  3
 8GO  Var_34    H24  C25  C13  N7     60.39  30.0  3
 8GO  Var_35    H15  C22  C21  C20   -57.27  30.0  1
 8GO  Var_36    H16  C22  C21  C20  -172.15  30.0  1
 8GO  Var_37    H7   C17  C16  C15    -1.05  30.0  3
 8GO  Var_38    H8   C17  C16  C15   119.98  30.0  3
 8GO  Var_39    H9   C17  C16  C15  -122.61  30.0  3
 8GO  Var_40    H10  C18  C16  C15    -0.34  30.0  3
 8GO  Var_41    H11  C18  C16  C15   120.55  30.0  3
 8GO  Var_42    H12  C18  C16  C15  -121.23  30.0  3
 8GO  Var_43    H10  C18  C16  C17   179.53  30.0  3
 8GO  Var_44    H11  C18  C16  C17   -59.58  30.0  3
 8GO  Var_45    H12  C18  C16  C17    58.63  30.0  3
 8GO  Var_46    H7   C17  C16  C18   179.09  30.0  3
 8GO  Var_47    H8   C17  C16  C18   -59.88  30.0  3
 8GO  Var_48    H9   C17  C16  C18    57.54  30.0  3
 8GO  Var_49    H13  C21  C22  O26  -173.13  30.0  3
 8GO  Var_50    H14  C21  C22  O26   -58.65  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
 8GO  chir_01  C14  C19  C15  C9   negativ
 8GO  chir_02  C20  C19  O11  C21  negativ

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
 8GO  plan-1  C4   0.020
 8GO  plan-1  N7   0.020
 8GO  plan-1  C13  0.020
 8GO  plan-1  C9   0.020
 8GO  plan-1  C8   0.020
 8GO  plan-1  O12  0.020
 8GO  plan-2  C1   0.020
 8GO  plan-2  C4   0.020
 8GO  plan-2  C5   0.020
 8GO  plan-2  C6   0.020
 8GO  plan-2  N7   0.020
 8GO  plan-2  N3   0.020
 8GO  plan-2  C2   0.020
 8GO  plan-2  C24  0.020
 8GO  plan-2  C10  0.020
 8GO  plan-2  H1   0.020
 8GO  plan-2  H2   0.020
 8GO  plan-3  C14  0.020
 8GO  plan-3  C15  0.020
 8GO  plan-3  C16  0.020
 8GO  plan-3  C17  0.020
 8GO  plan-3  C18  0.020
 8GO  plan-3  H6   0.020

