# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Jul 31 06:01:53 2021
#   Inital geometry file: a 143 line input string
#   Ligand name: (2R,3R)-2,3-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)[C@H](OC(=O)\C=C\c1ccc(O)c(O)c1)[C@@H](OC(=O)/C=C/c2ccc(O)c(O)c2)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
 GKP  GKP  '(2R,3R)-2,3-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid'  ligand  52  34  .  2021-08-10  2022-11-17
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_GKP
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
 GKP  C1   C  CR16  0  -0.322   2.5864  -12.9588   3.3496
 GKP  C10  C  CH1   0  -0.113   4.5076  -19.2274   3.5726
 GKP  C11  C  C     0   0.538   3.9259  -19.7469   4.8829
 GKP  C12  C  CH1   0  -0.110   4.0676  -20.1023   2.4058
 GKP  C14  C  C1    0  -0.447   0.6275  -21.1471   1.9218
 GKP  C15  C  C1    0  -0.208  -0.1415  -22.0905   1.3582
 GKP  C16  C  CR6   0   0.138  -1.5906  -22.1746   1.4125
 GKP  C17  C  CR16  0  -0.396  -2.2124  -23.2861   0.8320
 GKP  C18  C  CR6   0   0.311  -3.5868  -23.4335   0.8484
 GKP  C19  C  CR6   0   0.262  -4.3735  -22.4438   1.4551
 GKP  C2   C  CR16  0  -0.321   2.0525  -11.6872   3.2545
 GKP  C20  C  CR16  0  -0.351  -3.7645  -21.3350   2.0299
 GKP  C21  C  CR16  0  -0.322  -2.3883  -21.1986   2.0120
 GKP  C22  C  C     0   0.537   4.5704  -19.4883   1.1050
 GKP  C3   C  CR6   0   0.297   2.5621  -10.6429   4.0174
 GKP  C4   C  CR6   0   0.279   3.6332  -10.8905   4.8885
 GKP  C5   C  CR16  0  -0.428   4.1604  -12.1638   4.9816
 GKP  C6   C  CR6   0   0.138   3.6481  -13.2200   4.2177
 GKP  C7   C  C1    0  -0.209   4.2397  -14.5356   4.3795
 GKP  C8   C  C1    0  -0.449   3.8778  -15.6629   3.7490
 GKP  C9   C  C     0   0.616   4.5515  -16.9239   4.0486
 GKP  O1   O  O     0  -0.446   5.4594  -17.0923   4.8258
 GKP  O10  O  O     0  -0.429   5.7465  -19.4038   0.8687
 GKP  O11  O  OH1   0  -0.642   4.0790   -9.8293   5.5955
 GKP  O12  O  OH1   0  -0.620   2.0145   -9.4232   3.8996
 GKP  O2   O  O2    0  -0.480   4.0250  -17.9291   3.3253
 GKP  O3   O  O     0  -0.408   3.1664  -19.1235   5.5697
 GKP  O4   O  OH1   0  -0.586   4.3737  -20.9611   5.1403
 GKP  O5   O  O2    0  -0.481   2.6627  -20.1969   2.4648
 GKP  O6   O  O     0  -0.444   2.7172  -21.9891   1.1277
 GKP  O7   O  OH1   0  -0.632  -5.7035  -22.6458   1.4343
 GKP  O8   O  OH1   0  -0.631  -4.1368  -24.5238   0.2777
 GKP  O9   O  OH1   0  -0.567   3.6020  -19.0737   0.3190
 GKP  H1   H  HCR6  0   0.260   2.1629  -13.7457   2.7401
 GKP  H2   H  HCH1  0   0.326   5.6004  -19.2558   3.6311
 GKP  H3   H  HCH1  0   0.327   4.5437  -21.0815   2.5090
 GKP  H4   H  H     0   0.282   0.2098  -20.3330   2.5002
 GKP  H5   H  H     0   0.272   0.3506  -22.8847   0.8047
 GKP  H6   H  HCR6  0   0.271  -1.6130  -24.0549   0.3580
 GKP  H7   H  HCR6  0   0.275   1.2259  -11.4929   2.5830
 GKP  H8   H  HCR6  0   0.283  -4.3756  -20.5702   2.4951
 GKP  H9   H  HCR6  0   0.262  -1.9457  -20.3215   2.4642
 GKP  H10  H  HCR6  0   0.281   4.9864  -12.3464   5.6612
 GKP  H11  H  H     0   0.272   5.0518  -14.5943   5.0981
 GKP  H12  H  H     0   0.281   3.0780  -15.6863   3.0201
 GKP  H13  H  HOH1  0   0.485   4.8309  -10.0713   6.1473
 GKP  H14  H  HOH1  0   0.478   2.4442   -8.7948   4.4927
 GKP  H15  H  HOH1  0   0.496   3.9909  -21.3033   5.9634
 GKP  H16  H  HOH1  0   0.487  -6.1754  -21.9080   1.8375
 GKP  H17  H  HOH1  0   0.475  -5.0976  -24.5032   0.3577
 GKP  H18  H  HOH1  0   0.495   3.9664  -18.6958  -0.4969
 GKP  C13  C  C     0   0.619   2.0795  -21.1915   1.7710

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
 GKP  O8   C18  single    1.348  0.020  1.348
 GKP  C18  C17  aromatic  1.382  0.020  1.382
 GKP  C18  C19  aromatic  1.402  0.020  1.402
 GKP  C17  C16  aromatic  1.400  0.020  1.400
 GKP  O10  C22  double    1.203  0.020  1.203
 GKP  O9   C22  single    1.314  0.020  1.314
 GKP  O7   C19  single    1.345  0.020  1.345
 GKP  C19  C20  aromatic  1.389  0.020  1.389
 GKP  C16  C15  single    1.453  0.020  1.453
 GKP  C16  C21  aromatic  1.396  0.020  1.396
 GKP  C15  C14  double    1.341  0.020  1.341
 GKP  C22  C12  single    1.524  0.020  1.524
 GKP  O6   C13  double    1.207  0.020  1.207
 GKP  C20  C21  aromatic  1.383  0.020  1.383
 GKP  C14  C13  single    1.461  0.020  1.461
 GKP  C13  O5   single    1.346  0.020  1.346
 GKP  C12  O5   single    1.409  0.020  1.409
 GKP  C12  C10  single    1.523  0.020  1.523
 GKP  C10  O2   single    1.407  0.020  1.407
 GKP  C10  C11  single    1.525  0.020  1.525
 GKP  O2   C9   single    1.346  0.020  1.346
 GKP  C2   C1   aromatic  1.382  0.020  1.382
 GKP  C2   C3   aromatic  1.390  0.020  1.390
 GKP  C1   C6   aromatic  1.396  0.020  1.396
 GKP  O12  C3   single    1.342  0.020  1.342
 GKP  C3   C4   aromatic  1.403  0.020  1.403
 GKP  C8   C9   single    1.461  0.020  1.461
 GKP  C8   C7   double    1.341  0.020  1.341
 GKP  C9   O1   double    1.207  0.020  1.207
 GKP  C6   C7   single    1.452  0.020  1.452
 GKP  C6   C5   aromatic  1.401  0.020  1.401
 GKP  C4   C5   aromatic  1.381  0.020  1.381
 GKP  C4   O11  single    1.351  0.020  1.351
 GKP  C11  O3   double    1.199  0.020  1.199
 GKP  C11  O4   single    1.319  0.020  1.319
 GKP  C1   H1   single    0.930  0.020  1.080
 GKP  C10  H2   single    0.970  0.020  1.090
 GKP  C12  H3   single    0.970  0.020  1.090
 GKP  C14  H4   single    0.930  0.020  1.080
 GKP  C15  H5   single    0.930  0.020  1.080
 GKP  C17  H6   single    0.930  0.020  1.080
 GKP  C2   H7   single    0.930  0.020  1.080
 GKP  C20  H8   single    0.930  0.020  1.080
 GKP  C21  H9   single    0.930  0.020  1.080
 GKP  C5   H10  single    0.930  0.020  1.080
 GKP  C7   H11  single    0.930  0.020  1.080
 GKP  C8   H12  single    0.930  0.020  1.080
 GKP  O11  H13  single    0.850  0.020  0.980
 GKP  O12  H14  single    0.850  0.020  0.980
 GKP  O4   H15  single    0.850  0.020  0.980
 GKP  O7   H16  single    0.850  0.020  0.980
 GKP  O8   H17  single    0.850  0.020  0.980
 GKP  O9   H18  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
 GKP  H1   C1   C6   120.80  3.000
 GKP  H1   C1   C2   118.63  3.000
 GKP  C6   C1   C2   120.57  3.000
 GKP  H2   C10  O2   112.08  3.000
 GKP  H2   C10  C12  108.32  3.000
 GKP  O2   C10  C12  107.24  3.000
 GKP  H2   C10  C11  109.03  3.000
 GKP  O2   C10  C11  109.54  3.000
 GKP  C12  C10  C11  110.63  3.000
 GKP  O4   C11  O3   125.57  3.000
 GKP  O4   C11  C10  110.59  3.000
 GKP  O3   C11  C10  123.84  3.000
 GKP  H3   C12  O5   111.71  3.000
 GKP  H3   C12  C22  107.31  3.000
 GKP  O5   C12  C22  113.06  3.000
 GKP  H3   C12  C10  108.44  3.000
 GKP  O5   C12  C10  107.13  3.000
 GKP  C22  C12  C10  109.09  3.000
 GKP  H4   C14  C15  122.16  3.000
 GKP  H4   C14  C13  117.49  3.000
 GKP  C15  C14  C13  120.34  3.000
 GKP  H5   C15  C16  115.39  3.000
 GKP  H5   C15  C14  117.96  3.000
 GKP  C16  C15  C14  126.65  3.000
 GKP  C21  C16  C17  118.65  3.000
 GKP  C21  C16  C15  123.08  3.000
 GKP  C17  C16  C15  118.27  3.000
 GKP  H6   C17  C18  118.65  3.000
 GKP  H6   C17  C16  119.93  3.000
 GKP  C18  C17  C16  121.43  3.000
 GKP  O8   C18  C19  121.68  3.000
 GKP  C19  C18  C17  119.19  3.000
 GKP  O8   C18  C17  119.13  3.000
 GKP  O7   C19  C20  124.02  3.000
 GKP  C20  C19  C18  119.75  3.000
 GKP  O7   C19  C18  116.22  3.000
 GKP  H7   C2   C3   119.05  3.000
 GKP  H7   C2   C1   120.18  3.000
 GKP  C3   C2   C1   120.78  3.000
 GKP  H8   C20  C21  119.81  3.000
 GKP  H8   C20  C19  119.57  3.000
 GKP  C21  C20  C19  120.63  3.000
 GKP  H9   C21  C20  118.80  3.000
 GKP  H9   C21  C16  120.85  3.000
 GKP  C20  C21  C16  120.35  3.000
 GKP  O9   C22  O10  125.51  3.000
 GKP  O9   C22  C12  113.24  3.000
 GKP  O10  C22  C12  121.25  3.000
 GKP  O12  C3   C4   121.77  3.000
 GKP  C4   C3   C2   119.22  3.000
 GKP  O12  C3   C2   119.01  3.000
 GKP  O11  C4   C5   124.26  3.000
 GKP  O11  C4   C3   116.00  3.000
 GKP  C5   C4   C3   119.74  3.000
 GKP  H10  C5   C6   119.54  3.000
 GKP  H10  C5   C4   119.20  3.000
 GKP  C6   C5   C4   121.25  3.000
 GKP  C7   C6   C5   118.27  3.000
 GKP  C5   C6   C1   118.44  3.000
 GKP  C7   C6   C1   123.28  3.000
 GKP  H11  C7   C8   117.86  3.000
 GKP  H11  C7   C6   115.31  3.000
 GKP  C8   C7   C6   126.82  3.000
 GKP  H12  C8   C9   117.40  3.000
 GKP  H12  C8   C7   122.28  3.000
 GKP  C9   C8   C7   120.31  3.000
 GKP  O2   C9   O1   122.42  3.000
 GKP  O1   C9   C8   126.83  3.000
 GKP  O2   C9   C8   110.74  3.000
 GKP  H13  O11  C4   111.10  3.000
 GKP  H14  O12  C3   110.86  3.000
 GKP  C9   O2   C10  117.43  3.000
 GKP  H15  O4   C11  110.87  3.000
 GKP  C13  O5   C12  117.40  3.000
 GKP  H16  O7   C19  111.25  3.000
 GKP  H17  O8   C18  110.74  3.000
 GKP  H18  O9   C22  110.43  3.000
 GKP  O6   C13  O5   122.30  3.000
 GKP  O5   C13  C14  110.80  3.000
 GKP  O6   C13  C14  126.90  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
 GKP  CONST_01  C4   C3   C2   C1      0.00   0.0  0
 GKP  CONST_02  C4   C5   C6   C1      0.00   0.0  0
 GKP  CONST_03  C19  C18  C17  C16     0.00   0.0  0
 GKP  CONST_04  C19  C20  C21  C16     0.00   0.0  0
 GKP  CONST_05  C20  C19  C18  C17     0.00   0.0  0
 GKP  CONST_06  C20  C21  C16  C17     0.00   0.0  0
 GKP  CONST_07  C21  C16  C17  C18     0.00   0.0  0
 GKP  CONST_08  C21  C20  C19  C18     0.00   0.0  0
 GKP  CONST_09  C5   C6   C1   C2      0.00   0.0  0
 GKP  CONST_10  C5   C4   C3   C2      0.00   0.0  0
 GKP  CONST_11  C6   C1   C2   C3      0.00   0.0  0
 GKP  CONST_12  C6   C5   C4   C3      0.00   0.0  0
 GKP  CONST_13  O12  C3   C2   C1    180.00   0.0  0
 GKP  CONST_14  C18  C17  C16  C15   180.00   0.0  0
 GKP  CONST_15  C20  C21  C16  C15   180.00   0.0  0
 GKP  CONST_16  O8   C18  C17  C16   180.00   0.0  0
 GKP  CONST_17  O7   C19  C18  C17   180.00   0.0  0
 GKP  CONST_18  C7   C6   C1   C2    180.00   0.0  0
 GKP  CONST_19  O11  C4   C3   C2    180.00   0.0  0
 GKP  CONST_20  O8   C18  C19  C20   180.00   0.0  0
 GKP  CONST_21  O7   C19  C20  C21   180.00   0.0  0
 GKP  CONST_22  C7   C6   C5   C4    180.00   0.0  0
 GKP  CONST_23  O12  C3   C4   C5    180.00   0.0  0
 GKP  CONST_24  O11  C4   C5   C6    180.00   0.0  0
 GKP  CONST_25  H10  C5   C6   C1    180.00   0.0  0
 GKP  CONST_26  H8   C20  C21  C16   180.00   0.0  0
 GKP  CONST_27  H9   C21  C16  C17   180.00   0.0  0
 GKP  CONST_28  H6   C17  C18  C19   180.00   0.0  0
 GKP  CONST_29  H1   C1   C2   C3    180.00   0.0  0
 GKP  CONST_30  H7   C2   C3   C4    180.00   0.0  0
 GKP  CONST_31  H15  O4   C11  C10   180.00   0.0  0
 GKP  CONST_32  H18  O9   C22  C12   180.00   0.0  0
 GKP  Var_01    C8   C7   C6   C1      0.01  30.0  2
 GKP  Var_02    C17  C16  C15  C14  -175.92  30.0  3
 GKP  Var_03    C16  C15  C14  C13  -179.56   0.0  2
 GKP  Var_04    C9   C8   C7   C6   -178.34   0.0  2
 GKP  Var_05    C8   C9   O2   C10  -175.66  30.0  3
 GKP  Var_06    O6   C13  O5   C12     0.69  30.0  1
 GKP  Var_07    O2   C9   C8   C7    179.05  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
 GKP  chir_01  C10  C12  O2   C11  negativ
 GKP  chir_02  C12  O5   C10  C22  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
 GKP  plan-1  C15  0.020
 GKP  plan-1  C16  0.020
 GKP  plan-1  C17  0.020
 GKP  plan-1  C18  0.020
 GKP  plan-1  C19  0.020
 GKP  plan-1  C20  0.020
 GKP  plan-1  C21  0.020
 GKP  plan-1  O7   0.020
 GKP  plan-1  O8   0.020
 GKP  plan-1  H6   0.020
 GKP  plan-1  H8   0.020
 GKP  plan-1  H9   0.020
 GKP  plan-2  C1   0.020
 GKP  plan-2  C2   0.020
 GKP  plan-2  C3   0.020
 GKP  plan-2  C4   0.020
 GKP  plan-2  C5   0.020
 GKP  plan-2  C6   0.020
 GKP  plan-2  C7   0.020
 GKP  plan-2  O11  0.020
 GKP  plan-2  O12  0.020
 GKP  plan-2  H1   0.020
 GKP  plan-2  H7   0.020
 GKP  plan-2  H10  0.020
 GKP  plan-3  C10  0.020
 GKP  plan-3  C11  0.020
 GKP  plan-3  O3   0.020
 GKP  plan-3  O4   0.020
 GKP  plan-3  H15  0.020
 GKP  plan-4  C12  0.020
 GKP  plan-4  C22  0.020
 GKP  plan-4  O10  0.020
 GKP  plan-4  O9   0.020
 GKP  plan-4  H18  0.020
 GKP  plan-5  C14  0.020
 GKP  plan-5  C15  0.020
 GKP  plan-5  C16  0.020
 GKP  plan-5  H4   0.020
 GKP  plan-5  H5   0.020
 GKP  plan-5  C13  0.020
 GKP  plan-6  C14  0.020
 GKP  plan-6  O5   0.020
 GKP  plan-6  O6   0.020
 GKP  plan-6  C13  0.020
 GKP  plan-7  C6   0.020
 GKP  plan-7  C7   0.020
 GKP  plan-7  C8   0.020
 GKP  plan-7  C9   0.020
 GKP  plan-7  H11  0.020
 GKP  plan-7  H12  0.020
 GKP  plan-8  C8   0.020
 GKP  plan-8  C9   0.020
 GKP  plan-8  O1   0.020
 GKP  plan-8  O2   0.020

