# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Apr 24 06:50:29 2020
#   Inital geometry file: a 138 line input string
#   Ligand name: (3alpha,5beta,8alpha,12beta)-3,12,14-trihydroxycard-20(22)-enolide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@]12CC[C@H](O)C[C@H]1CC[C@@H]3[C@@H]2C[C@@H](O)[C@]4(C)[C@H](CC[C@]34O)C5=CC(=O)OC5
#
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
 DOG  DOG  (3alpha,5beta,8alpha,12beta)-3,12,14-trihydroxycard-20(22)-enolide  ligand  62  28  .  2021-08-08  2021-08-08  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_DOG
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
 DOG  O23   O  O     0  -0.454   0.6658  -0.2372  -7.1495
 DOG  C23   C  CR5   0   0.556   0.2800  -0.0267  -6.0272
 DOG  C22   C  CR15  0  -0.472   1.0153   0.4158  -4.8456
 DOG  O21   O  O     0  -0.459  -1.0105  -0.1824  -5.6857
 DOG  C21   C  CH2   0  -0.199  -1.1885   0.1147  -4.3047
 DOG  C20   C  CR5   0   0.158   0.1704   0.5143  -3.8149
 DOG  C17   C  CH1   0  -0.324   0.5132   0.9780  -2.4394
 DOG  C16   C  CH2   0  -0.428  -0.4173   2.1081  -1.9265
 DOG  C13   C  CT    0  -0.083   0.5057  -0.1208  -1.3187
 DOG  C18   C  CH3   0  -0.684   0.6128  -1.5507  -1.8462
 DOG  C12   C  CH1   0   0.089   1.6982   0.1878  -0.3917
 DOG  O12   O  OH1   0  -0.671   2.8836  -0.1336  -1.0904
 DOG  C14   C  CT    0   0.306  -0.8063   0.1630  -0.5446
 DOG  C15   C  CH2   0  -0.516  -0.8761   1.6915  -0.5269
 DOG  O14   O  OH1   0  -0.681  -1.8534  -0.3209  -1.3744
 DOG  C8    C  CH1   0  -0.232  -0.8810  -0.5171   0.8338
 DOG  C7    C  CH2   0  -0.451  -2.1806  -0.1739   1.5645
 DOG  C9    C  CH1   0  -0.235   0.3479  -0.2142   1.7058
 DOG  C11   C  CH2   0  -0.481   1.6244  -0.5447   0.9385
 DOG  C10   C  CT    0  -0.049   0.2776  -0.9139   3.0901
 DOG  C19   C  CH3   0  -0.679   0.3592  -2.4389   2.9443
 DOG  C5    C  CH1   0  -0.206  -1.0437  -0.5317   3.8002
 DOG  C6    C  CH2   0  -0.431  -2.2576  -0.8461   2.9298
 DOG  C4    C  CH2   0  -0.449  -1.0667   0.9318   4.2565
 DOG  C3    C  CH1   0   0.048   0.1091   1.3123   5.1401
 DOG  O32   O  OH1   0  -0.679  -0.0318   0.6256   6.3722
 DOG  C2    C  CH2   0  -0.483   1.4183   0.9614   4.4417
 DOG  C1    C  CH2   0  -0.413   1.4438  -0.4966   4.0060
 DOG  H22   H  HCR5  0   0.274   2.0733   0.6312  -4.8527
 DOG  H211  H  HCH2  0   0.275  -1.5755  -0.7661  -3.7959
 DOG  H212  H  HCH2  0   0.264  -1.9260   0.9132  -4.2029
 DOG  H17   H  HCH1  0   0.270   1.5328   1.3578  -2.5176
 DOG  H161  H  HCH2  0   0.249   0.1049   3.0643  -1.9163
 DOG  H162  H  HCH2  0   0.237  -1.2782   2.2387  -2.5817
 DOG  H181  H  HCH3  0   0.240   1.4404  -1.6511  -2.5474
 DOG  H182  H  HCH3  0   0.237   0.7832  -2.2668  -1.0416
 DOG  H183  H  HCH3  0   0.239  -0.2907  -1.8699  -2.3608
 DOG  H12   H  HCH1  0   0.211   1.6895   1.2674  -0.1749
 DOG  H12O  H  HOH1  0   0.448   3.6289   0.1093  -0.5322
 DOG  H151  H  HCH2  0   0.241  -0.2265   2.1072   0.2448
 DOG  H152  H  HCH2  0   0.250  -1.8816   2.0574  -0.3034
 DOG  H14O  H  HOH1  0   0.447  -2.6728   0.1169  -1.1239
 DOG  HC8   H  HCH1  0   0.222  -0.8968  -1.5965   0.6357
 DOG  HC71  H  HCH2  0   0.224  -3.0449  -0.4874   0.9727
 DOG  HC72  H  HCH2  0   0.224  -2.2667   0.9107   1.6827
 DOG  HC9   H  HCH1  0   0.219   0.3554   0.8674   1.8904
 DOG  H111  H  HCH2  0   0.238   2.5007  -0.2558   1.5261
 DOG  H112  H  HCH2  0   0.228   1.7063  -1.6223   0.7712
 DOG  H191  H  HCH3  0   0.228   0.1064  -2.9191   3.8920
 DOG  H192  H  HCH3  0   0.231  -0.3124  -2.8417   2.1867
 DOG  H193  H  HCH3  0   0.229   1.3691  -2.7604   2.6835
 DOG  HC5   H  HCH1  0   0.217  -1.1057  -1.1530   4.7007
 DOG  HC61  H  HCH2  0   0.225  -2.3501  -1.9282   2.7977
 DOG  HC62  H  HCH2  0   0.225  -3.1697  -0.5278   3.4431
 DOG  HC41  H  HCH2  0   0.231  -2.0050   1.1300   4.7851
 DOG  HC42  H  HCH2  0   0.223  -1.0600   1.6082   3.3984
 DOG  HC3   H  HCH1  0   0.206   0.0802   2.3980   5.3135
 DOG  H32O  H  HOH1  0   0.445   0.7421   0.8165   6.9112
 DOG  HC21  H  HCH2  0   0.234   2.2625   1.1657   5.1092
 DOG  HC22  H  HCH2  0   0.221   1.5488   1.6307   3.5863
 DOG  HC11  H  HCH2  0   0.220   1.4010  -1.1270   4.9006
 DOG  HC12  H  HCH2  0   0.228   2.4023  -0.7313   3.5368

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
 DOG  O23  C23   double  1.205  0.020  1.205
 DOG  C23  C22   single  1.460  0.020  1.460
 DOG  C23  O21   single  1.344  0.020  1.344
 DOG  C22  C20   double  1.336  0.020  1.336
 DOG  C22  H22   single  0.930  0.020  1.080
 DOG  O21  C21   single  1.424  0.020  1.424
 DOG  C21  C20   single  1.499  0.020  1.499
 DOG  C21  H211  single  0.970  0.020  1.090
 DOG  C21  H212  single  0.970  0.020  1.090
 DOG  C20  C17   single  1.491  0.020  1.491
 DOG  C17  C16   single  1.551  0.020  1.551
 DOG  C17  C13   single  1.569  0.020  1.569
 DOG  C17  H17   single  0.970  0.020  1.090
 DOG  C16  C15   single  1.531  0.020  1.531
 DOG  C16  H161  single  0.970  0.020  1.090
 DOG  C16  H162  single  0.970  0.020  1.090
 DOG  C13  C18   single  1.528  0.020  1.528
 DOG  C13  C12   single  1.542  0.020  1.542
 DOG  C13  C14   single  1.550  0.020  1.550
 DOG  C18  H181  single  0.970  0.020  1.090
 DOG  C18  H182  single  0.970  0.020  1.090
 DOG  C18  H183  single  0.970  0.020  1.090
 DOG  C12  O12   single  1.413  0.020  1.413
 DOG  C12  C11   single  1.520  0.020  1.520
 DOG  C12  H12   single  0.970  0.020  1.090
 DOG  O12  H12O  single  0.850  0.020  0.980
 DOG  C14  C15   single  1.530  0.020  1.530
 DOG  C14  O14   single  1.421  0.020  1.421
 DOG  C14  C8    single  1.539  0.020  1.539
 DOG  C15  H151  single  0.970  0.020  1.090
 DOG  C15  H152  single  0.970  0.020  1.090
 DOG  O14  H14O  single  0.850  0.020  0.980
 DOG  C8   C7    single  1.530  0.020  1.530
 DOG  C8   C9    single  1.537  0.020  1.537
 DOG  C8   HC8   single  0.970  0.020  1.090
 DOG  C7   C6    single  1.524  0.020  1.524
 DOG  C7   HC71  single  0.970  0.020  1.090
 DOG  C7   HC72  single  0.970  0.020  1.090
 DOG  C9   C11   single  1.526  0.020  1.526
 DOG  C9   C10   single  1.553  0.020  1.553
 DOG  C9   HC9   single  0.970  0.020  1.090
 DOG  C11  H111  single  0.970  0.020  1.090
 DOG  C11  H112  single  0.970  0.020  1.090
 DOG  C10  C19   single  1.534  0.020  1.534
 DOG  C10  C5    single  1.548  0.020  1.548
 DOG  C10  C1    single  1.541  0.020  1.541
 DOG  C19  H191  single  0.970  0.020  1.090
 DOG  C19  H192  single  0.970  0.020  1.090
 DOG  C19  H193  single  0.970  0.020  1.090
 DOG  C5   C6    single  1.526  0.020  1.526
 DOG  C5   C4    single  1.533  0.020  1.533
 DOG  C5   HC5   single  0.970  0.020  1.090
 DOG  C6   HC61  single  0.970  0.020  1.090
 DOG  C6   HC62  single  0.970  0.020  1.090
 DOG  C4   C3    single  1.519  0.020  1.519
 DOG  C4   HC41  single  0.970  0.020  1.090
 DOG  C4   HC42  single  0.970  0.020  1.090
 DOG  C3   O32   single  1.418  0.020  1.418
 DOG  C3   C2    single  1.525  0.020  1.525
 DOG  C3   HC3   single  0.970  0.020  1.090
 DOG  O32  H32O  single  0.850  0.020  0.980
 DOG  C2   C1    single  1.522  0.020  1.522
 DOG  C2   HC21  single  0.970  0.020  1.090
 DOG  C2   HC22  single  0.970  0.020  1.090
 DOG  C1   HC11  single  0.970  0.020  1.090
 DOG  C1   HC12  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
 DOG  O21   C23  C22   108.24  3.000
 DOG  O21   C23  O23   121.58  3.000
 DOG  C22   C23  O23   130.18  3.000
 DOG  H22   C22  C20   127.58  3.000
 DOG  H22   C22  C23   123.26  3.000
 DOG  C20   C22  C23   109.15  3.000
 DOG  C21   O21  C23   110.02  3.000
 DOG  H212  C21  H211  107.95  3.000
 DOG  H212  C21  C20   112.77  3.000
 DOG  H211  C21  C20   112.67  3.000
 DOG  H212  C21  O21   109.12  3.000
 DOG  H211  C21  O21   109.21  3.000
 DOG  C20   C21  O21   105.02  3.000
 DOG  C17   C20  C21   126.34  3.000
 DOG  C17   C20  C22   126.08  3.000
 DOG  C21   C20  C22   107.55  3.000
 DOG  H17   C17  C13   107.42  3.000
 DOG  H17   C17  C16   109.31  3.000
 DOG  C13   C17  C16   105.73  3.000
 DOG  H17   C17  C20   104.89  3.000
 DOG  C13   C17  C20   116.09  3.000
 DOG  C16   C17  C20   113.18  3.000
 DOG  H162  C16  H161  106.20  3.000
 DOG  H162  C16  C15   110.22  3.000
 DOG  H161  C16  C15   111.96  3.000
 DOG  H162  C16  C17   111.25  3.000
 DOG  H161  C16  C17   110.79  3.000
 DOG  C15   C16  C17   106.49  3.000
 DOG  C14   C13  C12   108.53  3.000
 DOG  C14   C13  C18   113.78  3.000
 DOG  C12   C13  C18   109.92  3.000
 DOG  C14   C13  C17   103.45  3.000
 DOG  C12   C13  C17   106.60  3.000
 DOG  C18   C13  C17   114.10  3.000
 DOG  H183  C18  H182  106.63  3.000
 DOG  H183  C18  H181  107.43  3.000
 DOG  H182  C18  H181  107.20  3.000
 DOG  H183  C18  C13   112.32  3.000
 DOG  H182  C18  C13   111.76  3.000
 DOG  H181  C18  C13   111.21  3.000
 DOG  H12   C12  C11   107.44  3.000
 DOG  H12   C12  O12   109.08  3.000
 DOG  C11   C12  O12   111.33  3.000
 DOG  H12   C12  C13   107.97  3.000
 DOG  C11   C12  C13   113.09  3.000
 DOG  O12   C12  C13   107.82  3.000
 DOG  H12O  O12  C12   107.79  3.000
 DOG  C8    C14  O14   109.68  3.000
 DOG  C8    C14  C15   115.40  3.000
 DOG  O14   C14  C15   108.26  3.000
 DOG  C8    C14  C13   114.06  3.000
 DOG  O14   C14  C13   105.66  3.000
 DOG  C15   C14  C13   103.14  3.000
 DOG  H152  C15  H151  105.99  3.000
 DOG  H152  C15  C14   112.25  3.000
 DOG  H151  C15  C14   111.20  3.000
 DOG  H152  C15  C16   111.81  3.000
 DOG  H151  C15  C16   111.38  3.000
 DOG  C14   C15  C16   104.34  3.000
 DOG  H14O  O14  C14   108.70  3.000
 DOG  HC8   C8   C9    107.92  3.000
 DOG  HC8   C8   C7    107.13  3.000
 DOG  C9    C8   C7    111.35  3.000
 DOG  HC8   C8   C14   105.88  3.000
 DOG  C9    C8   C14   112.48  3.000
 DOG  C7    C8   C14   111.71  3.000
 DOG  HC72  C7   HC71  106.28  3.000
 DOG  HC72  C7   C6    109.66  3.000
 DOG  HC71  C7   C6    108.58  3.000
 DOG  HC72  C7   C8    109.92  3.000
 DOG  HC71  C7   C8    110.41  3.000
 DOG  C6    C7   C8    111.83  3.000
 DOG  HC9   C9   C10   107.12  3.000
 DOG  HC9   C9   C11   107.01  3.000
 DOG  C10   C9   C11   112.87  3.000
 DOG  HC9   C9   C8    107.17  3.000
 DOG  C10   C9   C8    112.38  3.000
 DOG  C11   C9   C8    109.94  3.000
 DOG  H112  C11  H111  106.40  3.000
 DOG  H112  C11  C9    110.68  3.000
 DOG  H111  C11  C9    110.05  3.000
 DOG  H112  C11  C12   109.71  3.000
 DOG  H111  C11  C12   107.69  3.000
 DOG  C9    C11  C12   112.10  3.000
 DOG  C1    C10  C5    107.85  3.000
 DOG  C1    C10  C19   106.59  3.000
 DOG  C5    C10  C19   109.54  3.000
 DOG  C1    C10  C9    111.95  3.000
 DOG  C5    C10  C9    109.65  3.000
 DOG  C19   C10  C9    111.15  3.000
 DOG  H193  C19  H192  107.18  3.000
 DOG  H193  C19  H191  106.98  3.000
 DOG  H192  C19  H191  107.35  3.000
 DOG  H193  C19  C10   111.39  3.000
 DOG  H192  C19  C10   113.63  3.000
 DOG  H191  C19  C10   110.01  3.000
 DOG  HC5   C5   C4    107.20  3.000
 DOG  HC5   C5   C6    107.87  3.000
 DOG  C4    C5   C6    110.76  3.000
 DOG  HC5   C5   C10   106.58  3.000
 DOG  C4    C5   C10   112.65  3.000
 DOG  C6    C5   C10   111.49  3.000
 DOG  HC62  C6   HC61  105.90  3.000
 DOG  HC62  C6   C5    109.61  3.000
 DOG  HC61  C6   C5    109.87  3.000
 DOG  HC62  C6   C7    109.52  3.000
 DOG  HC61  C6   C7    109.41  3.000
 DOG  C5    C6   C7    112.33  3.000
 DOG  HC42  C4   HC41  105.80  3.000
 DOG  HC42  C4   C3    107.27  3.000
 DOG  HC41  C4   C3    109.70  3.000
 DOG  HC42  C4   C5    110.92  3.000
 DOG  HC41  C4   C5    109.23  3.000
 DOG  C3    C4   C5    113.61  3.000
 DOG  HC3   C3   C2    108.78  3.000
 DOG  HC3   C3   O32   109.79  3.000
 DOG  C2    C3   O32   111.84  3.000
 DOG  HC3   C3   C4    108.58  3.000
 DOG  C2    C3   C4    109.91  3.000
 DOG  O32   C3   C4    107.90  3.000
 DOG  H32O  O32  C3    108.11  3.000
 DOG  HC22  C2   HC21  105.69  3.000
 DOG  HC22  C2   C1    111.12  3.000
 DOG  HC21  C2   C1    109.89  3.000
 DOG  HC22  C2   C3    108.65  3.000
 DOG  HC21  C2   C3    109.86  3.000
 DOG  C1    C2   C3    111.46  3.000
 DOG  HC12  C1   HC11  105.15  3.000
 DOG  HC12  C1   C2    110.08  3.000
 DOG  HC11  C1   C2    108.48  3.000
 DOG  HC12  C1   C10   110.52  3.000
 DOG  HC11  C1   C10   107.47  3.000
 DOG  C2    C1   C10   114.65  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
 DOG  Var_01  C21  C20  C22  C23    0.47  30.0  1
 DOG  Var_02  C20  C21  O21  C23    1.24  30.0  1
 DOG  Var_03  O21  C21  C20  C22   -1.03  30.0  1
 DOG  Var_04  C20  C22  C23  O21    0.30  30.0  1
 DOG  Var_05  C14  C15  C16  C17  -26.79  30.0  1
 DOG  Var_06  C5   C6   C7   C8    54.53  30.0  1
 DOG  Var_07  C3   C2   C1   C10   56.41  30.0  1

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
 DOG  chir_01  C17  C20  C16  C13  negativ
 DOG  chir_02  C13  C12  C14  C17  negativ
 DOG  chir_03  C12  O12  C13  C11  negativ
 DOG  chir_04  C14  C8   C15  C13  negativ
 DOG  chir_05  C8   C14  C7   C9   positiv
 DOG  chir_06  C9   C10  C11  C8   negativ
 DOG  chir_07  C10  C9   C5   C1   positiv
 DOG  chir_08  C5   C4   C6   C10  negativ
 DOG  chir_09  C3   O32  C4   C2   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
 DOG  plan-1  O23  0.020
 DOG  plan-1  C23  0.020
 DOG  plan-1  C22  0.020
 DOG  plan-1  O21  0.020

