# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Jun  1 15:34:40 2020
#   Inital geometry file: a 98 line input string
#   Ligand name: (1R,4R,5R)-1,4,5-trihydroxy-3-[(1S)-1-hydroxy-2-phenylethyl]cyclohex-2-ene-1-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: O[C@@H]1C[C@@](O)(C=C([C@@H](O)Cc2ccccc2)[C@H]1O)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
 W4N  W4N  '(1R,4R,5R)-1,4,5-trihydroxy-3-[(1S)-1-hydroxy-2-phenylethyl]cyclohex-2-ene-1-carboxylic acid'  ligand  39  21  .  2021-08-24  2022-11-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_W4N
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
 W4N  CAK   C  CR16  0  -0.318  -3.9886   0.6168   1.0802
 W4N  CAI   C  CR16  0  -0.242  -5.3548   0.3679   1.0944
 W4N  CAH   C  CR16  0  -0.273  -6.0081  -0.0060  -0.0726
 W4N  CAJ   C  CR16  0  -0.240  -5.2858  -0.1246  -1.2531
 W4N  CAL   C  CR16  0  -0.308  -3.9209   0.1296  -1.2619
 W4N  CAQ   C  CR6   0   0.170  -3.2541   0.5035  -0.0970
 W4N  CAM   C  CH2   0  -0.588  -1.7715   0.7458  -0.1138
 W4N  CAR   C  CH1   0  -0.004  -0.9889  -0.5609   0.0199
 W4N  OAC   O  OH1   0  -0.655  -1.3675  -1.2809   1.1777
 W4N  CAP   C  C     0   0.020   0.5172  -0.4122  -0.0243
 W4N  CAG   C  C1    0  -0.259   1.1237   0.7517  -0.2396
 W4N  CAU   C  CT    0   0.063   2.6164   0.9212  -0.3500
 W4N  CAO   C  C     0   0.530   3.0385   2.1146   0.5102
 W4N  OAB   O  OH1   0  -0.579   4.0762   2.7666   0.0167
 W4N  OAA   O  O     0  -0.430   2.4991   2.3947   1.5509
 W4N  OAF   O  OH1   0  -0.653   3.0108   1.0753  -1.6917
 W4N  CAN   C  CH2   0  -0.513   3.3411  -0.3083   0.1998
 W4N  CAS   C  CH1   0   0.052   2.7047  -1.5933  -0.3142
 W4N  OAD   O  OH1   0  -0.672   3.4181  -2.7243   0.1255
 W4N  CAT   C  CH1   0   0.001   1.2894  -1.6987   0.2234
 W4N  OAE   O  OH1   0  -0.668   0.6702  -2.8074  -0.3855
 W4N  HAK   H  HCR6  0   0.242  -3.4915   0.9160   1.9953
 W4N  HAI   H  HCR6  0   0.253  -5.9101   0.4662   2.0186
 W4N  HAH   H  HCR6  0   0.253  -7.0733  -0.1974  -0.0630
 W4N  HAJ   H  HCR6  0   0.253  -5.7856  -0.4117  -2.1694
 W4N  HAL   H  HCR6  0   0.246  -3.3656   0.0406  -2.1890
 W4N  HAM1  H  HCH2  0   0.260  -1.4904   1.2287  -1.0519
 W4N  HAM2  H  HCH2  0   0.255  -1.4951   1.4324   0.6921
 W4N  HAR   H  HCH1  0   0.255  -1.2802  -1.2012  -0.8194
 W4N  HAC   H  HOH1  0   0.449  -1.1170  -0.7668   1.9533
 W4N  HAG   H  H     0   0.280   0.5376   1.6508  -0.3996
 W4N  HAT   H  HCH1  0   0.230   1.3603  -1.8476   1.3112
 W4N  HAF   H  HOH1  0   0.456   2.4519   1.7345  -2.1180
 W4N  HAN1  H  HCH2  0   0.270   4.3965  -0.2616  -0.0825
 W4N  HAN2  H  HCH2  0   0.261   3.2996  -0.3076   1.2927
 W4N  HAB   H  HOH1  0   0.484   4.3301   3.4813   0.6205
 W4N  HAS   H  HCH1  0   0.217   2.6574  -1.5620  -1.4118
 W4N  HAD   H  HOH1  0   0.452   4.2806  -2.7185  -0.3009
 W4N  HAE   H  HOH1  0   0.456  -0.0636  -3.0843   0.1724

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
 W4N  CAK  CAI   aromatic  1.389  0.020  1.389
 W4N  CAK  CAQ   aromatic  1.392  0.020  1.392
 W4N  CAI  CAH   aromatic  1.389  0.020  1.389
 W4N  CAH  CAJ   aromatic  1.389  0.020  1.389
 W4N  CAJ  CAL   aromatic  1.388  0.020  1.388
 W4N  CAL  CAQ   aromatic  1.393  0.020  1.393
 W4N  CAQ  CAM   single    1.502  0.020  1.502
 W4N  CAM  CAR   single    1.529  0.020  1.529
 W4N  CAR  OAC   single    1.415  0.020  1.415
 W4N  CAR  CAP   single    1.514  0.020  1.514
 W4N  CAP  CAG   double    1.330  0.020  1.330
 W4N  CAP  CAT   single    1.521  0.020  1.521
 W4N  CAG  CAU   single    1.506  0.020  1.506
 W4N  CAU  CAO   single    1.530  0.020  1.530
 W4N  CAU  OAF   single    1.407  0.020  1.407
 W4N  CAU  CAN   single    1.529  0.020  1.529
 W4N  CAO  OAB   single    1.321  0.020  1.321
 W4N  CAO  OAA   double    1.205  0.020  1.205
 W4N  CAN  CAS   single    1.523  0.020  1.523
 W4N  CAS  OAD   single    1.408  0.020  1.408
 W4N  CAS  CAT   single    1.518  0.020  1.518
 W4N  CAT  OAE   single    1.408  0.020  1.408
 W4N  CAK  HAK   single    0.930  0.020  1.080
 W4N  CAI  HAI   single    0.930  0.020  1.080
 W4N  CAH  HAH   single    0.930  0.020  1.080
 W4N  CAJ  HAJ   single    0.930  0.020  1.080
 W4N  CAL  HAL   single    0.930  0.020  1.080
 W4N  CAM  HAM1  single    0.970  0.020  1.090
 W4N  CAM  HAM2  single    0.970  0.020  1.090
 W4N  CAR  HAR   single    0.970  0.020  1.090
 W4N  OAC  HAC   single    0.850  0.020  0.980
 W4N  CAG  HAG   single    0.930  0.020  1.080
 W4N  CAT  HAT   single    0.970  0.020  1.090
 W4N  OAF  HAF   single    0.850  0.020  0.980
 W4N  CAN  HAN1  single    0.970  0.020  1.090
 W4N  CAN  HAN2  single    0.970  0.020  1.090
 W4N  OAB  HAB   single    0.850  0.020  0.980
 W4N  CAS  HAS   single    0.970  0.020  1.090
 W4N  OAD  HAD   single    0.850  0.020  0.980
 W4N  OAE  HAE   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
 W4N  HAK   CAK  CAQ   119.64  3.000
 W4N  HAK   CAK  CAI   119.49  3.000
 W4N  CAQ   CAK  CAI   120.87  3.000
 W4N  HAI   CAI  CAH   120.03  3.000
 W4N  HAI   CAI  CAK   119.80  3.000
 W4N  CAH   CAI  CAK   120.17  3.000
 W4N  HAH   CAH  CAJ   120.28  3.000
 W4N  HAH   CAH  CAI   120.21  3.000
 W4N  CAJ   CAH  CAI   119.51  3.000
 W4N  HAJ   CAJ  CAL   119.81  3.000
 W4N  HAJ   CAJ  CAH   120.13  3.000
 W4N  CAL   CAJ  CAH   120.06  3.000
 W4N  HAL   CAL  CAQ   119.46  3.000
 W4N  HAL   CAL  CAJ   119.59  3.000
 W4N  CAQ   CAL  CAJ   120.95  3.000
 W4N  CAM   CAQ  CAL   120.41  3.000
 W4N  CAM   CAQ  CAK   121.13  3.000
 W4N  CAL   CAQ  CAK   118.44  3.000
 W4N  HAM2  CAM  HAM1  106.88  3.000
 W4N  HAM2  CAM  CAR   110.03  3.000
 W4N  HAM1  CAM  CAR   108.74  3.000
 W4N  HAM2  CAM  CAQ   110.01  3.000
 W4N  HAM1  CAM  CAQ   109.57  3.000
 W4N  CAR   CAM  CAQ   111.49  3.000
 W4N  HAR   CAR  CAP   107.44  3.000
 W4N  HAR   CAR  OAC   104.98  3.000
 W4N  CAP   CAR  OAC   109.88  3.000
 W4N  HAR   CAR  CAM   107.25  3.000
 W4N  CAP   CAR  CAM   115.00  3.000
 W4N  OAC   CAR  CAM   111.68  3.000
 W4N  HAC   OAC  CAR   108.51  3.000
 W4N  CAT   CAP  CAG   122.35  3.000
 W4N  CAT   CAP  CAR   114.66  3.000
 W4N  CAG   CAP  CAR   122.98  3.000
 W4N  HAG   CAG  CAU   115.54  3.000
 W4N  HAG   CAG  CAP   120.18  3.000
 W4N  CAU   CAG  CAP   124.21  3.000
 W4N  CAN   CAU  OAF   107.34  3.000
 W4N  CAN   CAU  CAO   107.11  3.000
 W4N  OAF   CAU  CAO   111.92  3.000
 W4N  CAN   CAU  CAG   110.65  3.000
 W4N  OAF   CAU  CAG   111.10  3.000
 W4N  CAO   CAU  CAG   108.66  3.000
 W4N  OAA   CAO  OAB   124.02  3.000
 W4N  OAA   CAO  CAU   122.89  3.000
 W4N  OAB   CAO  CAU   113.05  3.000
 W4N  HAB   OAB  CAO   109.68  3.000
 W4N  HAF   OAF  CAU   109.52  3.000
 W4N  HAN2  CAN  HAN1  107.13  3.000
 W4N  HAN2  CAN  CAS   108.78  3.000
 W4N  HAN1  CAN  CAS   110.62  3.000
 W4N  HAN2  CAN  CAU   109.92  3.000
 W4N  HAN1  CAN  CAU   109.28  3.000
 W4N  CAS   CAN  CAU   111.03  3.000
 W4N  HAS   CAS  CAT   108.40  3.000
 W4N  HAS   CAS  OAD   110.89  3.000
 W4N  CAT   CAS  OAD   107.83  3.000
 W4N  HAS   CAS  CAN   109.33  3.000
 W4N  CAT   CAS  CAN   109.19  3.000
 W4N  OAD   CAS  CAN   111.14  3.000
 W4N  HAD   OAD  CAS   108.12  3.000
 W4N  HAT   CAT  OAE   110.44  3.000
 W4N  HAT   CAT  CAS   107.43  3.000
 W4N  OAE   CAT  CAS   108.16  3.000
 W4N  HAT   CAT  CAP   107.95  3.000
 W4N  OAE   CAT  CAP   111.86  3.000
 W4N  CAS   CAT  CAP   110.92  3.000
 W4N  HAE   OAE  CAT   108.13  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
 W4N  CONST_01  CAJ  CAH  CAI  CAK    0.00   0.0  0
 W4N  CONST_02  CAJ  CAL  CAQ  CAK    0.00   0.0  0
 W4N  CONST_03  CAL  CAQ  CAK  CAI    0.00   0.0  0
 W4N  CONST_04  CAL  CAJ  CAH  CAI    0.00   0.0  0
 W4N  CONST_05  CAQ  CAK  CAI  CAH    0.00   0.0  0
 W4N  CONST_06  CAQ  CAL  CAJ  CAH    0.00   0.0  0
 W4N  CONST_07  CAM  CAQ  CAK  CAI  180.00   0.0  0
 W4N  CONST_08  CAM  CAQ  CAL  CAJ  180.00   0.0  0
 W4N  CONST_09  HAH  CAH  CAI  CAK  180.00   0.0  0
 W4N  CONST_10  HAL  CAL  CAQ  CAK  180.00   0.0  0
 W4N  CONST_11  HAJ  CAJ  CAH  CAI  180.00   0.0  0
 W4N  CONST_12  HAK  CAK  CAI  CAH  180.00   0.0  0
 W4N  CONST_13  HAI  CAI  CAH  CAJ  180.00   0.0  0
 W4N  CONST_14  HAB  OAB  CAO  CAU  180.00   0.0  0
 W4N  Var_01    CAT  CAP  CAG  CAU    4.00  30.0  1
 W4N  Var_02    CAR  CAM  CAQ  CAK   95.50  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
 W4N  chir_01  CAR  CAM  OAC  CAP  positiv
 W4N  chir_02  CAU  CAN  CAO  CAG  positiv
 W4N  chir_03  CAS  OAD  CAN  CAT  positiv
 W4N  chir_04  CAT  OAE  CAS  CAP  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
 W4N  plan-1  CAK  0.020
 W4N  plan-1  CAI  0.020
 W4N  plan-1  CAH  0.020
 W4N  plan-1  CAJ  0.020
 W4N  plan-1  CAL  0.020
 W4N  plan-1  CAQ  0.020
 W4N  plan-1  CAM  0.020
 W4N  plan-1  HAK  0.020
 W4N  plan-1  HAI  0.020
 W4N  plan-1  HAH  0.020
 W4N  plan-1  HAJ  0.020
 W4N  plan-1  HAL  0.020
 W4N  plan-2  CAU  0.020
 W4N  plan-2  CAO  0.020
 W4N  plan-2  OAB  0.020
 W4N  plan-2  OAA  0.020
 W4N  plan-2  HAB  0.020

