# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Apr  3 21:32:09 2020
#   Inital geometry file: a 105 line input string
#   Ligand name: (3R,4S,5R)-3,4-dihydroxy-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohex-1-ene-1-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: O[C@@H]1C=C(C[C@@H](OC(=O)\C=C\c2ccc(O)cc2)[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
 4KE  4KE  '(3R,4S,5R)-3,4-dihydroxy-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohex-1-ene-1-carboxylic acid'  ligand  38  23  .  2021-08-04  2021-08-04  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_4KE
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
 4KE  C01  C  CH2    0  -0.516   2.6383   0.6934  -0.2823
 4KE  C02  C  CH1    0   0.036   2.0049  -0.5833   0.2469
 4KE  C03  C  CH1    0  -0.008   2.6942  -1.8182  -0.2989
 4KE  C04  C  CH1    0  -0.025   4.1415  -1.8275   0.1953
 4KE  C05  C  C1     0  -0.290   4.7915  -0.4825   0.0551
 4KE  C06  C  C      0  -0.087   4.1341   0.6576  -0.1558
 4KE  C07  C  C      0   0.393   4.8894   1.9755  -0.3010
 4KE  O08  O  OC    -1  -0.595   4.1893   2.9823  -0.5278
 4KE  O09  O  O      0  -0.595   6.1300   1.9429  -0.1887
 4KE  O10  O  OH1    0  -0.670   4.1211  -2.2636   1.5454
 4KE  O11  O  OH1    0  -0.670   2.6374  -1.7681  -1.7023
 4KE  O12  O  O2     0  -0.491   0.6244  -0.6670  -0.1286
 4KE  C13  C  C      0   0.600  -0.2878  -0.0421   0.6117
 4KE  C14  C  C1     0  -0.446  -1.6341  -0.2513   0.0635
 4KE  C15  C  C1     0  -0.211  -2.7014   0.3152   0.6429
 4KE  C16  C  CR6    0   0.124  -4.0882   0.2099   0.2230
 4KE  O17  O  O      0  -0.462  -0.0260   0.6057   1.6004
 4KE  C18  C  CR16   0  -0.287  -5.0624   0.9109   0.9376
 4KE  C19  C  CR16   0  -0.371  -6.3991   0.8620   0.5841
 4KE  C20  C  CR6    0   0.356  -6.7967   0.0962  -0.5091
 4KE  C21  C  CR16   0  -0.314  -5.8381  -0.6177  -1.2347
 4KE  C22  C  CR16   0  -0.296  -4.5101  -0.5579  -0.8704
 4KE  O23  O  OH1    0  -0.619  -8.0738   0.0063  -0.9087
 4KE  H1   H  HCH2   0   0.246   2.3591   0.8471  -1.3293
 4KE  H2   H  HCH2   0   0.251   2.2438   1.5526   0.2616
 4KE  H3   H  HCH1   0   0.253   2.0899  -0.6085   1.3363
 4KE  H4   H  HCH1   0   0.235   2.1909  -2.7156   0.0890
 4KE  H5   H  HCH1   0   0.220   4.6993  -2.5514  -0.4187
 4KE  H6   H  H      0   0.245   5.8726  -0.4523   0.1432
 4KE  H8   H  HOH1   0   0.453   5.0113  -2.1848   1.9021
 4KE  H9   H  HOH1   0   0.454   3.0267  -2.5752  -2.0532
 4KE  H10  H  H      0   0.270  -1.7184  -0.8741  -0.8183
 4KE  H11  H  H      0   0.266  -2.5335   0.9305   1.5221
 4KE  H12  H  HCR6   0   0.265  -4.7679   1.5093   1.7914
 4KE  H13  H  HCR6   0   0.278  -7.1298   1.4213   1.1568
 4KE  H14  H  HCR6   0   0.272  -6.1447  -1.2144  -2.0844
 4KE  H15  H  HCR6   0   0.258  -3.7943  -1.1255  -1.4509
 4KE  H16  H  HOH1   0   0.479  -8.6447   0.5439  -0.3475

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
 4KE  O09  C07  deloc     1.246  0.020  1.246
 4KE  O08  C07  deloc     1.247  0.020  1.247
 4KE  C07  C06  single    1.526  0.020  1.526
 4KE  C06  C01  single    1.502  0.020  1.502
 4KE  C06  C05  double    1.333  0.020  1.333
 4KE  C01  C02  single    1.520  0.020  1.520
 4KE  C05  C04  single    1.500  0.020  1.500
 4KE  C02  O12  single    1.433  0.020  1.433
 4KE  C02  C03  single    1.516  0.020  1.516
 4KE  O12  C13  single    1.331  0.020  1.331
 4KE  C04  C03  single    1.529  0.020  1.529
 4KE  C04  O10  single    1.419  0.020  1.419
 4KE  C03  O11  single    1.405  0.020  1.405
 4KE  C13  C14  single    1.469  0.020  1.469
 4KE  C13  O17  double    1.211  0.020  1.211
 4KE  C14  C15  double    1.340  0.020  1.340
 4KE  C22  C21  aromatic  1.378  0.020  1.378
 4KE  C22  C16  aromatic  1.401  0.020  1.401
 4KE  C21  C20  aromatic  1.398  0.020  1.398
 4KE  C15  C16  single    1.453  0.020  1.453
 4KE  C16  C18  aromatic  1.397  0.020  1.397
 4KE  C20  O23  single    1.341  0.020  1.341
 4KE  C20  C19  aromatic  1.393  0.020  1.393
 4KE  C18  C19  aromatic  1.384  0.020  1.384
 4KE  C01  H1   single    0.970  0.020  1.090
 4KE  C01  H2   single    0.970  0.020  1.090
 4KE  C02  H3   single    0.970  0.020  1.090
 4KE  C03  H4   single    0.970  0.020  1.090
 4KE  C04  H5   single    0.970  0.020  1.090
 4KE  C05  H6   single    0.930  0.020  1.080
 4KE  O10  H8   single    0.850  0.020  0.980
 4KE  O11  H9   single    0.850  0.020  0.980
 4KE  C14  H10  single    0.930  0.020  1.080
 4KE  C15  H11  single    0.930  0.020  1.080
 4KE  C18  H12  single    0.930  0.020  1.080
 4KE  C19  H13  single    0.930  0.020  1.080
 4KE  C21  H14  single    0.930  0.020  1.080
 4KE  C22  H15  single    0.930  0.020  1.080
 4KE  O23  H16  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
 4KE  H2   C01  H1   105.91  3.000
 4KE  H2   C01  C06  109.70  3.000
 4KE  H1   C01  C06  109.76  3.000
 4KE  H2   C01  C02  109.71  3.000
 4KE  H1   C01  C02  110.16  3.000
 4KE  C06  C01  C02  111.45  3.000
 4KE  H3   C02  O12  109.55  3.000
 4KE  H3   C02  C03  107.74  3.000
 4KE  O12  C02  C03  107.22  3.000
 4KE  H3   C02  C01  109.51  3.000
 4KE  C03  C02  C01  111.68  3.000
 4KE  O12  C02  C01  111.05  3.000
 4KE  H4   C03  O11  111.27  3.000
 4KE  H4   C03  C04  108.32  3.000
 4KE  O11  C03  C04  111.17  3.000
 4KE  H4   C03  C02  109.26  3.000
 4KE  O11  C03  C02  108.18  3.000
 4KE  C04  C03  C02  108.60  3.000
 4KE  H5   C04  O10  109.62  3.000
 4KE  H5   C04  C05  108.53  3.000
 4KE  O10  C04  C05  111.76  3.000
 4KE  H5   C04  C03  107.65  3.000
 4KE  O10  C04  C03  107.20  3.000
 4KE  C05  C04  C03  111.98  3.000
 4KE  H6   C05  C06  118.71  3.000
 4KE  H6   C05  C04  116.68  3.000
 4KE  C06  C05  C04  124.61  3.000
 4KE  C07  C06  C05  120.64  3.000
 4KE  C05  C06  C01  121.67  3.000
 4KE  C07  C06  C01  117.68  3.000
 4KE  O09  C07  O08  126.61  3.000
 4KE  O08  C07  C06  115.89  3.000
 4KE  O09  C07  C06  117.50  3.000
 4KE  H8   O10  C04  108.32  3.000
 4KE  H9   O11  C03  108.53  3.000
 4KE  C13  O12  C02  119.15  3.000
 4KE  O17  C13  C14  125.40  3.000
 4KE  O17  C13  O12  123.88  3.000
 4KE  C14  C13  O12  110.72  3.000
 4KE  H10  C14  C15  122.22  3.000
 4KE  H10  C14  C13  117.21  3.000
 4KE  C15  C14  C13  120.57  3.000
 4KE  H11  C15  C16  115.00  3.000
 4KE  H11  C15  C14  117.79  3.000
 4KE  C16  C15  C14  127.21  3.000
 4KE  C22  C16  C18  117.66  3.000
 4KE  C18  C16  C15  118.79  3.000
 4KE  C22  C16  C15  123.55  3.000
 4KE  H12  C18  C19  118.91  3.000
 4KE  H12  C18  C16  119.40  3.000
 4KE  C19  C18  C16  121.69  3.000
 4KE  H13  C19  C20  120.39  3.000
 4KE  H13  C19  C18  119.88  3.000
 4KE  C20  C19  C18  119.73  3.000
 4KE  O23  C20  C21  117.65  3.000
 4KE  O23  C20  C19  122.86  3.000
 4KE  C21  C20  C19  119.49  3.000
 4KE  H14  C21  C22  120.28  3.000
 4KE  H14  C21  C20  119.63  3.000
 4KE  C22  C21  C20  120.09  3.000
 4KE  H15  C22  C21  118.21  3.000
 4KE  H15  C22  C16  120.45  3.000
 4KE  C21  C22  C16  121.34  3.000
 4KE  H16  O23  C20  110.67  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
 4KE  CONST_01  C20  C21  C22  C16     0.00   0.0  0
 4KE  CONST_02  C20  C19  C18  C16     0.00   0.0  0
 4KE  CONST_03  C21  C22  C16  C18     0.00   0.0  0
 4KE  CONST_04  C21  C20  C19  C18     0.00   0.0  0
 4KE  CONST_05  C22  C21  C20  C19     0.00   0.0  0
 4KE  CONST_06  C22  C16  C18  C19     0.00   0.0  0
 4KE  CONST_07  C21  C22  C16  C15   180.00   0.0  0
 4KE  CONST_08  C19  C18  C16  C15   180.00   0.0  0
 4KE  CONST_09  O23  C20  C19  C18   180.00   0.0  0
 4KE  CONST_10  O23  C20  C21  C22   180.00   0.0  0
 4KE  CONST_11  H14  C21  C22  C16   180.00   0.0  0
 4KE  CONST_12  H13  C19  C18  C16   180.00   0.0  0
 4KE  CONST_13  H15  C22  C16  C18   180.00   0.0  0
 4KE  CONST_14  H12  C18  C19  C20   180.00   0.0  0
 4KE  Var_01    C04  C05  C06  C01    -0.33  30.0  1
 4KE  Var_02    C05  C06  C01  C02    16.39  30.0  1
 4KE  Var_03    O09  C07  C06  C01   179.64  30.0  2
 4KE  Var_04    C22  C16  C15  C14     1.70  30.0  2
 4KE  Var_05    C16  C15  C14  C13   179.77   0.0  2
 4KE  Var_06    C14  C13  O12  C02  -179.92  30.0  3
 4KE  Var_07    C15  C14  C13  O12  -178.66  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
 4KE  chir_01  C02  C01  O12  C03  negativ
 4KE  chir_02  C03  O11  C02  C04  positiv
 4KE  chir_03  C04  O10  C03  C05  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
 4KE  plan-1  C15  0.020
 4KE  plan-1  C16  0.020
 4KE  plan-1  C18  0.020
 4KE  plan-1  C19  0.020
 4KE  plan-1  C20  0.020
 4KE  plan-1  C21  0.020
 4KE  plan-1  C22  0.020
 4KE  plan-1  O23  0.020
 4KE  plan-1  H12  0.020
 4KE  plan-1  H13  0.020
 4KE  plan-1  H14  0.020
 4KE  plan-1  H15  0.020
 4KE  plan-2  C06  0.020
 4KE  plan-2  C07  0.020
 4KE  plan-2  O08  0.020
 4KE  plan-2  O09  0.020
 4KE  plan-3  O12  0.020
 4KE  plan-3  C13  0.020
 4KE  plan-3  C14  0.020
 4KE  plan-3  O17  0.020
 4KE  plan-4  C13  0.020
 4KE  plan-4  C14  0.020
 4KE  plan-4  C15  0.020
 4KE  plan-4  C16  0.020
 4KE  plan-4  H10  0.020
 4KE  plan-4  H11  0.020

