# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu May 21 08:21:16 2020
#   Inital geometry file: a 134 line input string
#   Ligand name: (5Z,9beta,11alpha,12alpha,13E,15S)-9-chloro-11,15-dihydroxyprosta-5,13-dien-1-oic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H](Cl)[C@@H]1C\C=C/CCCC(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
 ON5  ON5  '(5Z,9beta,11alpha,12alpha,13E,15S)-9-chloro-11,15-dihydroxyprosta-5,13-dien-1-oic acid'  ligand  58  25  .  2021-08-19  2021-08-19  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_ON5
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
 ON5  C20  C   CH3   0  -0.662   7.0584   4.6685  -0.4561
 ON5  C19  C   CH2   0  -0.418   5.7400   4.2236   0.1619
 ON5  C18  C   CH2   0  -0.408   5.1960   2.9385  -0.4498
 ON5  C17  C   CH2   0  -0.413   3.8756   2.4971   0.1695
 ON5  C16  C   CH2   0  -0.453   3.3357   1.2073  -0.4334
 ON5  C15  C   CH1   0   0.001   1.9714   0.8006   0.1252
 ON5  O15  O   OH1   0  -0.662   1.9923   0.6341   1.5230
 ON5  C14  C   C1    0  -0.262   1.4207  -0.3938  -0.6024
 ON5  C13  C   C1    0  -0.182   0.9213  -1.4842  -0.0302
 ON5  C12  C   CH1   0  -0.347   0.3008  -2.6237  -0.7673
 ON5  C11  C   CH1   0   0.075   0.8000  -4.0177  -0.3298
 ON5  O11  O   OH1   0  -0.672   1.7729  -4.4479  -1.2538
 ON5  C10  C   CH2   0  -0.461  -0.4598  -4.9096  -0.2709
 ON5  C9   C   CH1   0  -0.276  -1.5312  -4.0953  -0.9728
 ON5  CL9  CL  CL    0  -0.162  -3.1959  -4.6252  -0.5310
 ON5  C8   C   CH1   0  -0.188  -1.2284  -2.6622  -0.5731
 ON5  C7   C   CH2   0  -0.508  -1.9566  -1.5693  -1.3574
 ON5  C6   C   C1    0  -0.214  -3.3159  -1.2278  -0.8183
 ON5  C5   C   C1    0  -0.206  -3.5549  -0.3190   0.1260
 ON5  C4   C   CH2   0  -0.501  -2.5376   0.5373   0.8155
 ON5  C3   C   CH2   0  -0.416  -2.6525   2.0053   0.4021
 ON5  C2   C   CH2   0  -0.585  -1.6411   2.8714   1.1343
 ON5  C1   C   C     0   0.550  -1.7137   4.3290   0.7730
 ON5  O1A  O   O     0  -0.445  -2.5154   4.8200   0.0179
 ON5  O1B  O   OH1   0  -0.596  -0.7749   5.0382   1.3932
 ON5  H1   H   HCH3  0   0.226   7.4323   5.5788   0.0139
 ON5  H2   H   HCH3  0   0.216   7.8256   3.9000  -0.3436
 ON5  H3   H   HCH3  0   0.216   6.9488   4.8690  -1.5235
 ON5  H4   H   HCH2  0   0.210   5.8726   4.0814   1.2389
 ON5  H5   H   HCH2  0   0.211   4.9960   5.0189   0.0520
 ON5  H6   H   HCH2  0   0.207   5.0647   3.0772  -1.5287
 ON5  H7   H   HCH2  0   0.208   5.9384   2.1403  -0.3365
 ON5  H8   H   HCH2  0   0.213   4.0078   2.3738   1.2478
 ON5  H9   H   HCH2  0   0.209   3.1321   3.2924   0.0425
 ON5  H10  H   HCH2  0   0.225   3.2391   1.3241  -1.5173
 ON5  H11  H   HCH2  0   0.225   4.0501   0.3891  -0.2796
 ON5  H12  H   HCH1  0   0.231   1.2833   1.6377  -0.0549
 ON5  H13  H   HOH1  0   0.444   2.6491  -0.0394   1.7339
 ON5  H14  H   H     0   0.242   1.4297  -0.3167  -1.6874
 ON5  H15  H   H     0   0.237   0.8911  -1.5585   1.0543
 ON5  H16  H   HCH1  0   0.254   0.5000  -2.5216  -1.8415
 ON5  H17  H   HCH1  0   0.219   1.2332  -3.9562   0.6760
 ON5  H18  H   HOH1  0   0.451   2.1610  -5.2645  -0.9249
 ON5  H19  H   HCH2  0   0.261  -0.3051  -5.8919  -0.7190
 ON5  H20  H   HCH2  0   0.248  -0.7524  -5.0641   0.7695
 ON5  H21  H   HCH1  0   0.286  -1.4695  -4.2015  -2.0574
 ON5  H22  H   HCH1  0   0.251  -1.4463  -2.5512   0.4961
 ON5  H23  H   HCH2  0   0.251  -1.3274  -0.6753  -1.3546
 ON5  H24  H   HCH2  0   0.243  -2.0364  -1.8772  -2.4041
 ON5  H25  H   H     0   0.230  -4.1571  -1.7804  -1.2218
 ON5  H26  H   H     0   0.231  -4.5851  -0.1583   0.4326
 ON5  H27  H   HCH2  0   0.236  -2.6855   0.4607   1.8981
 ON5  H28  H   HCH2  0   0.237  -1.5223   0.1809   0.6221
 ON5  H29  H   HCH2  0   0.233  -2.5013   2.0874  -0.6768
 ON5  H30  H   HCH2  0   0.233  -3.6658   2.3611   0.6042
 ON5  H31  H   HCH2  0   0.281  -1.7687   2.7816   2.2180
 ON5  H32  H   HCH2  0   0.271  -0.6221   2.5242   0.9345
 ON5  H33  H   HOH1  0   0.478  -0.8478   5.9720   1.1456

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
 ON5  O15  C15  single  1.408  0.020  1.408
 ON5  C18  C17  single  1.524  0.020  1.524
 ON5  C18  C19  single  1.524  0.020  1.524
 ON5  C20  C19  single  1.522  0.020  1.522
 ON5  C16  C17  single  1.523  0.020  1.523
 ON5  C16  C15  single  1.529  0.020  1.529
 ON5  C15  C14  single  1.503  0.020  1.503
 ON5  C14  C13  double  1.329  0.020  1.329
 ON5  C13  C12  single  1.492  0.020  1.492
 ON5  O11  C11  single  1.409  0.020  1.409
 ON5  C11  C12  single  1.544  0.020  1.544
 ON5  C11  C10  single  1.545  0.020  1.545
 ON5  C12  C8   single  1.542  0.020  1.542
 ON5  C10  C9   single  1.518  0.020  1.518
 ON5  C8   C7   single  1.530  0.020  1.530
 ON5  C8   C9   single  1.518  0.020  1.518
 ON5  C7   C6   single  1.502  0.020  1.502
 ON5  C6   C5   double  1.332  0.020  1.332
 ON5  C9   CL9  single  1.802  0.020  1.802
 ON5  C5   C4   single  1.498  0.020  1.498
 ON5  C4   C3   single  1.529  0.020  1.529
 ON5  C3   C2   single  1.520  0.020  1.520
 ON5  C2   C1   single  1.504  0.020  1.504
 ON5  O1A  C1   double  1.206  0.020  1.206
 ON5  C1   O1B  single  1.330  0.020  1.330
 ON5  C20  H1   single  0.970  0.020  1.090
 ON5  C20  H2   single  0.970  0.020  1.090
 ON5  C20  H3   single  0.970  0.020  1.090
 ON5  C19  H4   single  0.970  0.020  1.090
 ON5  C19  H5   single  0.970  0.020  1.090
 ON5  C18  H6   single  0.970  0.020  1.090
 ON5  C18  H7   single  0.970  0.020  1.090
 ON5  C17  H8   single  0.970  0.020  1.090
 ON5  C17  H9   single  0.970  0.020  1.090
 ON5  C16  H10  single  0.970  0.020  1.090
 ON5  C16  H11  single  0.970  0.020  1.090
 ON5  C15  H12  single  0.970  0.020  1.090
 ON5  O15  H13  single  0.850  0.020  0.980
 ON5  C14  H14  single  0.930  0.020  1.080
 ON5  C13  H15  single  0.930  0.020  1.080
 ON5  C12  H16  single  0.970  0.020  1.090
 ON5  C11  H17  single  0.970  0.020  1.090
 ON5  O11  H18  single  0.850  0.020  0.980
 ON5  C10  H19  single  0.970  0.020  1.090
 ON5  C10  H20  single  0.970  0.020  1.090
 ON5  C9   H21  single  0.970  0.020  1.090
 ON5  C8   H22  single  0.970  0.020  1.090
 ON5  C7   H23  single  0.970  0.020  1.090
 ON5  C7   H24  single  0.970  0.020  1.090
 ON5  C6   H25  single  0.930  0.020  1.080
 ON5  C5   H26  single  0.930  0.020  1.080
 ON5  C4   H27  single  0.970  0.020  1.090
 ON5  C4   H28  single  0.970  0.020  1.090
 ON5  C3   H29  single  0.970  0.020  1.090
 ON5  C3   H30  single  0.970  0.020  1.090
 ON5  C2   H31  single  0.970  0.020  1.090
 ON5  C2   H32  single  0.970  0.020  1.090
 ON5  O1B  H33  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
 ON5  H3   C20  H2   107.50  3.000
 ON5  H3   C20  H1   107.61  3.000
 ON5  H2   C20  H1   107.60  3.000
 ON5  H3   C20  C19  111.32  3.000
 ON5  H2   C20  C19  111.16  3.000
 ON5  H1   C20  C19  111.46  3.000
 ON5  H5   C19  H4   105.99  3.000
 ON5  H5   C19  C18  109.25  3.000
 ON5  H4   C19  C18  109.19  3.000
 ON5  H5   C19  C20  109.61  3.000
 ON5  H4   C19  C20  109.43  3.000
 ON5  C18  C19  C20  113.12  3.000
 ON5  H7   C18  H6   105.97  3.000
 ON5  H7   C18  C17  109.52  3.000
 ON5  H6   C18  C17  109.46  3.000
 ON5  H7   C18  C19  109.32  3.000
 ON5  H6   C18  C19  109.35  3.000
 ON5  C17  C18  C19  112.99  3.000
 ON5  H9   C17  H8   106.15  3.000
 ON5  H9   C17  C16  109.16  3.000
 ON5  H8   C17  C16  109.75  3.000
 ON5  H9   C17  C18  109.30  3.000
 ON5  H8   C17  C18  109.20  3.000
 ON5  C16  C17  C18  113.06  3.000
 ON5  H11  C16  H10  106.02  3.000
 ON5  H11  C16  C15  109.36  3.000
 ON5  H10  C16  C15  108.14  3.000
 ON5  H11  C16  C17  110.20  3.000
 ON5  H10  C16  C17  109.45  3.000
 ON5  C15  C16  C17  113.39  3.000
 ON5  H12  C15  C14  107.26  3.000
 ON5  H12  C15  O15  105.21  3.000
 ON5  C14  C15  O15  113.08  3.000
 ON5  H12  C15  C16  107.24  3.000
 ON5  C14  C15  C16  111.18  3.000
 ON5  O15  C15  C16  112.38  3.000
 ON5  H13  O15  C15  108.06  3.000
 ON5  H14  C14  C13  119.39  3.000
 ON5  H14  C14  C15  115.06  3.000
 ON5  C13  C14  C15  125.54  3.000
 ON5  H15  C13  C12  115.40  3.000
 ON5  H15  C13  C14  119.73  3.000
 ON5  C12  C13  C14  124.76  3.000
 ON5  H16  C12  C8   107.80  3.000
 ON5  H16  C12  C11  107.62  3.000
 ON5  C8   C12  C11  105.22  3.000
 ON5  H16  C12  C13  109.70  3.000
 ON5  C8   C12  C13  111.66  3.000
 ON5  C11  C12  C13  114.52  3.000
 ON5  H17  C11  C10  108.63  3.000
 ON5  H17  C11  O11  110.23  3.000
 ON5  C10  C11  O11  114.32  3.000
 ON5  H17  C11  C12  109.69  3.000
 ON5  C10  C11  C12  105.57  3.000
 ON5  O11  C11  C12  108.24  3.000
 ON5  H18  O11  C11  108.27  3.000
 ON5  H20  C10  H19  107.58  3.000
 ON5  H20  C10  C9   109.12  3.000
 ON5  H19  C10  C9   113.16  3.000
 ON5  H20  C10  C11  109.67  3.000
 ON5  H19  C10  C11  112.87  3.000
 ON5  C9   C10  C11  104.38  3.000
 ON5  H21  C9   C8   110.01  3.000
 ON5  H21  C9   CL9  105.50  3.000
 ON5  C8   C9   CL9  113.41  3.000
 ON5  H21  C9   C10  111.56  3.000
 ON5  CL9  C9   C10  112.39  3.000
 ON5  C8   C9   C10  104.12  3.000
 ON5  H22  C8   C7   109.45  3.000
 ON5  H22  C8   C9   108.21  3.000
 ON5  C7   C8   C9   116.39  3.000
 ON5  H22  C8   C12  108.50  3.000
 ON5  C9   C8   C12  100.84  3.000
 ON5  C7   C8   C12  112.94  3.000
 ON5  H24  C7   H23  105.94  3.000
 ON5  H24  C7   C6   109.96  3.000
 ON5  H23  C7   C6   109.52  3.000
 ON5  H24  C7   C8   108.92  3.000
 ON5  H23  C7   C8   108.00  3.000
 ON5  C6   C7   C8   114.16  3.000
 ON5  H25  C6   C5   118.18  3.000
 ON5  H25  C6   C7   116.92  3.000
 ON5  C5   C6   C7   124.89  3.000
 ON5  H26  C5   C4   115.43  3.000
 ON5  H26  C5   C6   118.10  3.000
 ON5  C4   C5   C6   126.47  3.000
 ON5  H28  C4   H27  106.11  3.000
 ON5  H28  C4   C3   109.56  3.000
 ON5  H27  C4   C3   108.92  3.000
 ON5  H28  C4   C5   111.28  3.000
 ON5  H27  C4   C5   108.86  3.000
 ON5  C3   C4   C5   111.92  3.000
 ON5  H30  C3   H29  106.64  3.000
 ON5  H30  C3   C2   110.02  3.000
 ON5  H29  C3   C2   109.93  3.000
 ON5  H30  C3   C4   109.40  3.000
 ON5  H29  C3   C4   109.19  3.000
 ON5  C2   C3   C4   111.52  3.000
 ON5  H32  C2   H31  105.26  3.000
 ON5  H32  C2   C1   107.96  3.000
 ON5  H31  C2   C1   108.16  3.000
 ON5  H32  C2   C3   110.54  3.000
 ON5  H31  C2   C3   110.65  3.000
 ON5  C1   C2   C3   113.87  3.000
 ON5  O1B  C1   O1A  122.97  3.000
 ON5  O1B  C1   C2   111.77  3.000
 ON5  O1A  C1   C2   125.26  3.000
 ON5  H33  O1B  C1   109.98  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
 ON5  CONST_01  H33  O1B  C1   C2    180.00   0.0  0
 ON5  Var_01    C12  C13  C14  C15   175.96   0.0  2
 ON5  Var_02    C5   C6   C7   C8     88.11  30.0  3
 ON5  Var_03    C4   C5   C6   C7      0.66   0.0  2
 ON5  Var_04    C17  C18  C19  C20  -179.92  30.0  1
 ON5  Var_05    C16  C17  C18  C19  -179.57  30.0  3
 ON5  Var_06    C15  C16  C17  C18  -176.65  30.0  1
 ON5  Var_07    C3   C4   C5   C6    109.97  30.0  3
 ON5  Var_08    C2   C3   C4   C5    178.48  30.0  3
 ON5  Var_09    C1   C2   C3   C4   -179.64  30.0  3
 ON5  Var_10    O1A  C1   C2   C3      2.77  30.0  3
 ON5  Var_11    H1   C20  C19  C18  -178.91  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
 ON5  chir_01  C15  O15  C16  C14  negativ
 ON5  chir_02  C12  C8   C11  C13  positiv
 ON5  chir_03  C11  O11  C12  C10  negativ
 ON5  chir_04  C9   CL9  C8   C10  negativ
 ON5  chir_05  C8   C12  C7   C9   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
 ON5  plan-1  C2   0.020
 ON5  plan-1  C1   0.020
 ON5  plan-1  O1A  0.020
 ON5  plan-1  O1B  0.020
 ON5  plan-1  H33  0.020
 ON5  plan-2  C15  0.020
 ON5  plan-2  C14  0.020
 ON5  plan-2  C13  0.020
 ON5  plan-2  C12  0.020
 ON5  plan-2  H14  0.020
 ON5  plan-2  H15  0.020
 ON5  plan-3  C7   0.020
 ON5  plan-3  C6   0.020
 ON5  plan-3  C5   0.020
 ON5  plan-3  C4   0.020
 ON5  plan-3  H25  0.020
 ON5  plan-3  H26  0.020

