# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri May  8 18:17:45 2020
#   Inital geometry file: a 141 line input string
#   Ligand name: (11alpha,12alpha,13E,16S)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCC[C@](C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(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
 J9P  J9P  '(11alpha,12alpha,13E,16S)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oic acid'  ligand  62  26  .  2021-08-12  2021-08-12  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_J9P
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
 J9P  C01  C  CH3   0  -0.661   9.1815  -3.1983  -0.4343
 J9P  C02  C  CH2   0  -0.417   7.6882  -3.1651  -0.7299
 J9P  C03  C  CH2   0  -0.413   6.9924  -1.9557  -0.1157
 J9P  C04  C  CH2   0  -0.432   5.4980  -1.9333  -0.4152
 J9P  C05  C  CT    0   0.215   4.7007  -0.7991   0.2458
 J9P  C06  C  CH3   0  -0.671   5.1985   0.5666  -0.2080
 J9P  C07  C  CH2   0  -0.508   3.2111  -0.9776  -0.1205
 J9P  C08  C  C1    0  -0.208   2.3213   0.0522   0.4938
 J9P  C09  C  C1    0  -0.154   1.6629   0.9814  -0.1910
 J9P  C10  C  CH1   0  -0.357   0.8390   2.0635   0.4145
 J9P  C11  C  CH1   0   0.085   1.3898   3.4645   0.1282
 J9P  C12  C  CH2   0  -0.601   0.2236   4.3828   0.4866
 J9P  C13  C  C     0   0.419  -1.0116   3.5693   0.1708
 J9P  C15  C  CH1   0  -0.363  -0.5998   2.1363  -0.1161
 J9P  C16  C  CH2   0  -0.412  -1.5394   1.0662   0.4298
 J9P  C17  C  CH2   0  -0.419  -2.7966   0.8418  -0.4021
 J9P  C18  C  CH2   0  -0.416  -3.7224  -0.2020   0.2093
 J9P  C19  C  CH2   0  -0.415  -4.9734  -0.4506  -0.6237
 J9P  C20  C  CH2   0  -0.417  -5.9374  -1.4297   0.0349
 J9P  C21  C  CH2   0  -0.580  -7.1747  -1.6629  -0.8164
 J9P  C22  C  C     0   0.550  -8.1760  -2.5952  -0.1945
 J9P  O14  O  O     0  -0.397  -2.1421   3.9934   0.1731
 J9P  O23  O  OH1   0  -0.599  -9.2476  -2.7588  -0.9667
 J9P  O24  O  O     0  -0.446  -8.0504  -3.1434   0.8726
 J9P  O25  O  OH1   0  -0.658   2.5660   3.6807   0.8591
 J9P  O26  O  OH1   0  -0.678   4.8578  -0.8332   1.6575
 J9P  H1   H  HCH3  0   0.225   9.6613  -4.0661  -0.8886
 J9P  H2   H  HCH3  0   0.215   9.6806  -2.3061  -0.8175
 J9P  H3   H  HCH3  0   0.215   9.3685  -3.2429   0.6403
 J9P  H4   H  HCH2  0   0.210   7.5280  -3.1658  -1.8127
 J9P  H5   H  HCH2  0   0.210   7.2210  -4.0809  -0.3547
 J9P  H6   H  HCH2  0   0.210   7.1531  -1.9599   0.9661
 J9P  H7   H  HCH2  0   0.214   7.4680  -1.0453  -0.4932
 J9P  H8   H  HCH2  0   0.217   5.3458  -1.8795  -1.4981
 J9P  H9   H  HCH2  0   0.217   5.0610  -2.8901  -0.1006
 J9P  H10  H  HCH3  0   0.219   5.1027   0.6632  -1.2904
 J9P  H11  H  HCH3  0   0.242   4.6220   1.3731   0.2468
 J9P  H12  H  HCH3  0   0.234   6.2481   0.7136   0.0480
 J9P  H13  H  HCH2  0   0.235   3.1074  -0.9591  -1.2089
 J9P  H14  H  HCH2  0   0.234   2.8987  -1.9782   0.2033
 J9P  H15  H  H     0   0.229   2.2398   0.0462   1.5777
 J9P  H16  H  H     0   0.230   1.7435   1.0001  -1.2778
 J9P  H17  H  HCH1  0   0.251   0.8028   1.9326   1.5045
 J9P  H18  H  HCH1  0   0.208   1.5796   3.5448  -0.9526
 J9P  H19  H  HCH2  0   0.280   0.2245   4.5739   1.5665
 J9P  H20  H  HCH2  0   0.280   0.2213   5.3497  -0.0191
 J9P  H21  H  HCH1  0   0.278  -0.5588   2.0522  -1.2140
 J9P  H22  H  HCH2  0   0.232  -0.9808   0.1264   0.4884
 J9P  H23  H  HCH2  0   0.223  -1.8124   1.3180   1.4598
 J9P  H24  H  HCH2  0   0.223  -3.3409   1.7817  -0.5162
 J9P  H25  H  HCH2  0   0.210  -2.5077   0.5286  -1.4115
 J9P  H26  H  HCH2  0   0.210  -3.1787  -1.1440   0.3412
 J9P  H27  H  HCH2  0   0.210  -4.0155   0.1226   1.2138
 J9P  H28  H  HCH2  0   0.212  -5.4870   0.5012  -0.7991
 J9P  H29  H  HCH2  0   0.213  -4.6862  -0.8268  -1.6114
 J9P  H30  H  HCH2  0   0.225  -5.4263  -2.3790   0.2161
 J9P  H31  H  HCH2  0   0.224  -6.2291  -1.0427   1.0147
 J9P  H32  H  HCH2  0   0.275  -7.6785  -0.7141  -1.0279
 J9P  H33  H  HCH2  0   0.276  -6.8981  -2.0680  -1.7952
 J9P  H34  H  HOH1  0   0.478  -9.8729  -3.3613  -0.5375
 J9P  H35  H  HOH1  0   0.453   2.9538   4.5127   0.5711
 J9P  H36  H  HOH1  0   0.440   4.5783  -1.7006   1.9705

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
 J9P  O26  C05  single  1.421  0.020  1.421
 J9P  C06  C05  single  1.523  0.020  1.523
 J9P  C05  C04  single  1.536  0.020  1.536
 J9P  C05  C07  single  1.544  0.020  1.544
 J9P  C04  C03  single  1.524  0.020  1.524
 J9P  O25  C11  single  1.402  0.020  1.402
 J9P  C07  C08  single  1.493  0.020  1.493
 J9P  C02  C03  single  1.524  0.020  1.524
 J9P  C02  C01  single  1.523  0.020  1.523
 J9P  C08  C09  double  1.329  0.020  1.329
 J9P  C11  C10  single  1.532  0.020  1.532
 J9P  C11  C12  single  1.527  0.020  1.527
 J9P  C09  C10  single  1.489  0.020  1.489
 J9P  C10  C15  single  1.535  0.020  1.535
 J9P  C12  C13  single  1.512  0.020  1.512
 J9P  C15  C13  single  1.518  0.020  1.518
 J9P  C15  C16  single  1.525  0.020  1.525
 J9P  C13  O14  double  1.208  0.020  1.208
 J9P  C16  C17  single  1.524  0.020  1.524
 J9P  C17  C18  single  1.523  0.020  1.523
 J9P  C18  C19  single  1.523  0.020  1.523
 J9P  C19  C20  single  1.524  0.020  1.524
 J9P  C20  C21  single  1.520  0.020  1.520
 J9P  O24  C22  double  1.206  0.020  1.206
 J9P  C21  C22  single  1.503  0.020  1.503
 J9P  C22  O23  single  1.331  0.020  1.331
 J9P  C01  H1   single  0.970  0.020  1.090
 J9P  C01  H2   single  0.970  0.020  1.090
 J9P  C01  H3   single  0.970  0.020  1.090
 J9P  C02  H4   single  0.970  0.020  1.090
 J9P  C02  H5   single  0.970  0.020  1.090
 J9P  C03  H6   single  0.970  0.020  1.090
 J9P  C03  H7   single  0.970  0.020  1.090
 J9P  C04  H8   single  0.970  0.020  1.090
 J9P  C04  H9   single  0.970  0.020  1.090
 J9P  C06  H10  single  0.970  0.020  1.090
 J9P  C06  H11  single  0.970  0.020  1.090
 J9P  C06  H12  single  0.970  0.020  1.090
 J9P  C07  H13  single  0.970  0.020  1.090
 J9P  C07  H14  single  0.970  0.020  1.090
 J9P  C08  H15  single  0.930  0.020  1.080
 J9P  C09  H16  single  0.930  0.020  1.080
 J9P  C10  H17  single  0.970  0.020  1.090
 J9P  C11  H18  single  0.970  0.020  1.090
 J9P  C12  H19  single  0.970  0.020  1.090
 J9P  C12  H20  single  0.970  0.020  1.090
 J9P  C15  H21  single  0.970  0.020  1.090
 J9P  C16  H22  single  0.970  0.020  1.090
 J9P  C16  H23  single  0.970  0.020  1.090
 J9P  C17  H24  single  0.970  0.020  1.090
 J9P  C17  H25  single  0.970  0.020  1.090
 J9P  C18  H26  single  0.970  0.020  1.090
 J9P  C18  H27  single  0.970  0.020  1.090
 J9P  C19  H28  single  0.970  0.020  1.090
 J9P  C19  H29  single  0.970  0.020  1.090
 J9P  C20  H30  single  0.970  0.020  1.090
 J9P  C20  H31  single  0.970  0.020  1.090
 J9P  C21  H32  single  0.970  0.020  1.090
 J9P  C21  H33  single  0.970  0.020  1.090
 J9P  O23  H34  single  0.850  0.020  0.980
 J9P  O25  H35  single  0.850  0.020  0.980
 J9P  O26  H36  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
 J9P  H3   C01  H2   107.49  3.000
 J9P  H3   C01  H1   107.58  3.000
 J9P  H2   C01  H1   107.63  3.000
 J9P  H3   C01  C02  111.10  3.000
 J9P  H2   C01  C02  111.25  3.000
 J9P  H1   C01  C02  111.59  3.000
 J9P  H5   C02  H4   106.03  3.000
 J9P  H5   C02  C03  109.32  3.000
 J9P  H4   C02  C03  109.41  3.000
 J9P  H5   C02  C01  109.50  3.000
 J9P  H4   C02  C01  109.61  3.000
 J9P  C03  C02  C01  112.75  3.000
 J9P  H7   C03  H6   106.30  3.000
 J9P  H7   C03  C04  110.25  3.000
 J9P  H6   C03  C04  109.78  3.000
 J9P  H7   C03  C02  108.82  3.000
 J9P  H6   C03  C02  109.17  3.000
 J9P  C04  C03  C02  112.33  3.000
 J9P  H9   C04  H8   105.71  3.000
 J9P  H9   C04  C05  108.27  3.000
 J9P  H8   C04  C05  108.49  3.000
 J9P  H9   C04  C03  108.73  3.000
 J9P  H8   C04  C03  109.35  3.000
 J9P  C05  C04  C03  115.80  3.000
 J9P  O26  C05  C07  109.85  3.000
 J9P  C07  C05  C06  110.39  3.000
 J9P  O26  C05  C06  106.35  3.000
 J9P  C07  C05  C04  108.26  3.000
 J9P  C06  C05  C04  111.36  3.000
 J9P  O26  C05  C04  110.64  3.000
 J9P  H12  C06  H11  108.14  3.000
 J9P  H12  C06  H10  107.79  3.000
 J9P  H11  C06  H10  107.57  3.000
 J9P  H12  C06  C05  111.45  3.000
 J9P  H11  C06  C05  111.47  3.000
 J9P  H10  C06  C05  110.26  3.000
 J9P  H14  C07  H13  106.38  3.000
 J9P  H14  C07  C08  109.75  3.000
 J9P  H13  C07  C08  109.95  3.000
 J9P  H14  C07  C05  108.07  3.000
 J9P  H13  C07  C05  109.01  3.000
 J9P  C08  C07  C05  113.42  3.000
 J9P  H15  C08  C09  118.73  3.000
 J9P  H15  C08  C07  116.81  3.000
 J9P  C09  C08  C07  124.44  3.000
 J9P  H16  C09  C10  115.72  3.000
 J9P  H16  C09  C08  119.29  3.000
 J9P  C10  C09  C08  124.95  3.000
 J9P  H17  C10  C15  108.53  3.000
 J9P  H17  C10  C11  107.83  3.000
 J9P  C15  C10  C11  103.23  3.000
 J9P  H17  C10  C09  109.59  3.000
 J9P  C15  C10  C09  114.36  3.000
 J9P  C11  C10  C09  112.93  3.000
 J9P  H18  C11  O25  110.87  3.000
 J9P  H18  C11  C12  108.57  3.000
 J9P  O25  C11  C12  115.20  3.000
 J9P  H18  C11  C10  108.20  3.000
 J9P  C12  C11  C10  103.38  3.000
 J9P  O25  C11  C10  110.20  3.000
 J9P  H20  C12  H19  107.57  3.000
 J9P  H20  C12  C13  112.22  3.000
 J9P  H19  C12  C13  107.46  3.000
 J9P  H20  C12  C11  115.20  3.000
 J9P  H19  C12  C11  109.59  3.000
 J9P  C13  C12  C11  104.55  3.000
 J9P  O14  C13  C15  125.86  3.000
 J9P  O14  C13  C12  125.12  3.000
 J9P  C15  C13  C12  109.00  3.000
 J9P  H21  C15  C16  109.03  3.000
 J9P  H21  C15  C13  105.69  3.000
 J9P  C16  C15  C13  115.31  3.000
 J9P  H21  C15  C10  107.81  3.000
 J9P  C16  C15  C10  114.86  3.000
 J9P  C13  C15  C10  103.51  3.000
 J9P  H23  C16  H22  105.92  3.000
 J9P  H23  C16  C17  109.98  3.000
 J9P  H22  C16  C17  108.88  3.000
 J9P  H23  C16  C15  109.21  3.000
 J9P  H22  C16  C15  107.89  3.000
 J9P  C17  C16  C15  114.59  3.000
 J9P  H25  C17  H24  106.33  3.000
 J9P  H25  C17  C18  109.52  3.000
 J9P  H24  C17  C18  109.20  3.000
 J9P  H25  C17  C16  109.11  3.000
 J9P  H24  C17  C16  109.96  3.000
 J9P  C18  C17  C16  112.53  3.000
 J9P  H27  C18  H26  106.09  3.000
 J9P  H27  C18  C19  109.27  3.000
 J9P  H26  C18  C19  109.46  3.000
 J9P  H27  C18  C17  109.12  3.000
 J9P  H26  C18  C17  109.63  3.000
 J9P  C19  C18  C17  113.04  3.000
 J9P  H29  C19  H28  106.08  3.000
 J9P  H29  C19  C20  109.57  3.000
 J9P  H28  C19  C20  109.32  3.000
 J9P  H29  C19  C18  109.50  3.000
 J9P  H28  C19  C18  109.32  3.000
 J9P  C20  C19  C18  112.83  3.000
 J9P  H31  C20  H30  106.48  3.000
 J9P  H31  C20  C21  109.82  3.000
 J9P  H30  C20  C21  109.89  3.000
 J9P  H31  C20  C19  109.19  3.000
 J9P  H30  C20  C19  109.50  3.000
 J9P  C21  C20  C19  111.81  3.000
 J9P  H33  C21  H32  105.31  3.000
 J9P  H33  C21  C22  107.98  3.000
 J9P  H32  C21  C22  108.12  3.000
 J9P  H33  C21  C20  110.60  3.000
 J9P  H32  C21  C20  110.48  3.000
 J9P  C22  C21  C20  113.94  3.000
 J9P  O24  C22  O23  122.77  3.000
 J9P  O23  C22  C21  111.87  3.000
 J9P  O24  C22  C21  125.35  3.000
 J9P  H34  O23  C22  109.83  3.000
 J9P  H35  O25  C11  108.40  3.000
 J9P  H36  O26  C05  108.20  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
 J9P  CONST_01  H34  O23  C22  C21   180.00   0.0  0
 J9P  Var_01    C15  C13  C12  C11    10.14  30.0  1
 J9P  Var_02    C10  C09  C08  C07  -176.10   0.0  2
 J9P  Var_03    C18  C17  C16  C15  -178.10  30.0  3
 J9P  Var_04    C04  C03  C02  C01  -179.89  30.0  3
 J9P  Var_05    C05  C04  C03  C02   176.01  30.0  2
 J9P  Var_06    C09  C08  C07  C05   112.90  30.0  3
 J9P  Var_07    C19  C18  C17  C16  -179.15  30.0  3
 J9P  Var_08    C20  C19  C18  C17  -176.39  30.0  3
 J9P  Var_09    C21  C20  C19  C18  -179.88  30.0  3
 J9P  Var_10    C22  C21  C20  C19  -178.50  30.0  3
 J9P  Var_11    O24  C22  C21  C20    -0.70  30.0  3
 J9P  Var_12    H1   C01  C02  C03  -179.56  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
 J9P  chir_01  C05  C06  C04  C07  positiv
 J9P  chir_02  C10  C11  C09  C15  positiv
 J9P  chir_03  C11  O25  C10  C12  negativ
 J9P  chir_04  C15  C10  C13  C16  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
 J9P  plan-1  C12  0.020
 J9P  plan-1  C13  0.020
 J9P  plan-1  C15  0.020
 J9P  plan-1  O14  0.020
 J9P  plan-2  C21  0.020
 J9P  plan-2  C22  0.020
 J9P  plan-2  O23  0.020
 J9P  plan-2  O24  0.020
 J9P  plan-2  H34  0.020
 J9P  plan-3  C07  0.020
 J9P  plan-3  C08  0.020
 J9P  plan-3  C09  0.020
 J9P  plan-3  C10  0.020
 J9P  plan-3  H15  0.020
 J9P  plan-3  H16  0.020

