# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr  6 02:29:37 2020
#   Inital geometry file: a 158 line input string
#   Ligand name: (5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCNC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCc2ccccc2
#
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
 15M  15M  (5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide  ligand  67  30  .  2021-08-03  2021-08-03  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_15M
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
 15M  C1    C  C     0   0.541   3.8165   2.0401  -1.1297
 15M  C2    C  CH2   0  -0.570   3.5443   0.6464  -1.6474
 15M  C3    C  CH2   0  -0.417   4.2390  -0.4264  -0.8108
 15M  C4    C  CH2   0  -0.501   3.8526  -1.8266  -1.2925
 15M  C5    C  C1    0  -0.220   4.3415  -2.9287  -0.3975
 15M  C6    C  C1    0  -0.220   3.6505  -3.4279   0.6270
 15M  C7    C  CH2   0  -0.496   2.2858  -2.9514   1.0368
 15M  C8    C  CH1   0  -0.250   1.1546  -3.5470   0.2036
 15M  C9    C  CH1   0   0.053   0.8599  -5.0318   0.3950
 15M  C10   C  CH2   0  -0.512  -0.4827  -5.2011  -0.3276
 15M  C11   C  CH1   0   0.088  -1.1726  -3.8141  -0.3159
 15M  C12   C  CH1   0  -0.327  -0.2096  -2.8851   0.4359
 15M  C13   C  C1    0  -0.175  -0.2465  -1.4619  -0.0124
 15M  C14   C  C1    0  -0.260  -0.5924  -0.4382   0.7602
 15M  C15   C  CH1   0   0.015  -0.6197   1.0112   0.3680
 15M  C16   C  CH2   0  -0.458  -2.0443   1.5592   0.4682
 15M  C17   C  CH2   0  -0.514  -2.1357   3.0671   0.2297
 15M  C18   C  CR6   0   0.141  -3.5388   3.5743   0.4097
 15M  C19   C  CR16  0  -0.318  -4.3844   3.7539  -0.6823
 15M  C20   C  CR16  0  -0.239  -5.6929   4.1880  -0.5094
 15M  C21   C  CR16  0  -0.275  -6.1782   4.4485   0.7651
 15M  C22   C  CR16  0  -0.240  -5.3448   4.2724   1.8631
 15M  C23   C  CR16  0  -0.309  -4.0384   3.8394   1.6843
 15M  C24   C  CH3   0  -0.705   1.4533   4.5757   0.2031
 15M  C25   C  CH2   0  -0.260   2.8096   4.1082  -0.2888
 15M  N     N  NH1   0  -0.653   2.7332   2.7473  -0.7803
 15M  O1    O  O     0  -0.517   4.9566   2.4819  -1.0273
 15M  O9    O  OH1   0  -0.678   0.7631  -5.2869   1.7813
 15M  O11   O  OH1   0  -0.676  -2.4355  -3.7802   0.3078
 15M  O15   O  OH1   0  -0.663  -0.0386   1.2720  -0.8905
 15M  H21A  H  HCH2  0   0.242   2.4712   0.4444  -1.6716
 15M  H22A  H  HCH2  0   0.257   3.8963   0.5935  -2.6817
 15M  H31   H  HCH2  0   0.234   5.3226  -0.2978  -0.8499
 15M  H32   H  HCH2  0   0.230   3.9483  -0.3125   0.2373
 15M  H41   H  HCH2  0   0.231   2.7639  -1.8726  -1.3802
 15M  H42   H  HCH2  0   0.240   4.2414  -1.9775  -2.3034
 15M  H5    H  H     0   0.233   5.3282  -3.3300  -0.6074
 15M  H6    H  H     0   0.232   4.0901  -4.2335   1.2069
 15M  H71   H  HCH2  0   0.241   2.1164  -3.1649   2.0936
 15M  H72   H  HCH2  0   0.245   2.2315  -1.8636   0.9412
 15M  H8    H  HCH1  0   0.240   1.4061  -3.4193  -0.8578
 15M  H9    H  HCH1  0   0.214   1.6404  -5.6577  -0.0564
 15M  H101  H  HCH2  0   0.237  -0.3105  -5.5261  -1.3554
 15M  H102  H  HCH2  0   0.242  -1.1045  -5.9664   0.1446
 15M  H11   H  HCH1  0   0.201  -1.2585  -3.4621  -1.3534
 15M  H12   H  HCH1  0   0.238  -0.4483  -2.9386   1.5045
 15M  H13   H  H     0   0.229   0.0716  -1.2866  -1.0389
 15M  H14   H  H     0   0.244  -0.8983  -0.6295   1.7863
 15M  H15   H  HCH1  0   0.237   0.0004   1.5597   1.0876
 15M  H161  H  HCH2  0   0.238  -2.6884   1.0278  -0.2417
 15M  H162  H  HCH2  0   0.241  -2.4334   1.3266   1.4636
 15M  H171  H  HCH2  0   0.242  -1.4673   3.5793   0.9276
 15M  H172  H  HCH2  0   0.242  -1.7811   3.3045  -0.7749
 15M  H19   H  HCR6  0   0.245  -4.0146   3.5545  -1.6815
 15M  H20   H  HCR6  0   0.252  -6.3322   4.3254  -1.3723
 15M  H21   H  HCR6  0   0.253  -7.1964   4.7888   0.9029
 15M  H22   H  HCR6  0   0.252  -5.7127   4.4756   2.8608
 15M  H23   H  HCR6  0   0.245  -3.3951   3.7091   2.5474
 15M  H241  H  HCH3  0   0.245   1.5120   5.6112   0.5350
 15M  H242  H  HCH3  0   0.233   0.6994   4.5192  -0.5827
 15M  H243  H  HCH3  0   0.231   1.1080   3.9754   1.0458
 15M  H251  H  HCH2  0   0.229   3.1702   4.7741  -1.0782
 15M  H252  H  HCH2  0   0.233   3.5369   4.1626   0.5236
 15M  HN    H  HNH1  0   0.415   1.8181   2.3384  -0.9160
 15M  HO9   H  HOH1  0   0.448   0.4966  -6.2034   1.8986
 15M  H1    H  HOH1  0   0.448  -3.0422  -4.3153  -0.2125
 15M  H2    H  HOH1  0   0.453  -0.5963   0.9013  -1.5836

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
 15M  C1   C2    single    1.511  0.020  1.511
 15M  C1   N     single    1.340  0.020  1.340
 15M  C1   O1    double    1.227  0.020  1.227
 15M  C2   C3    single    1.528  0.020  1.528
 15M  C2   H21A  single    0.970  0.020  1.090
 15M  C2   H22A  single    0.970  0.020  1.090
 15M  C3   C4    single    1.530  0.020  1.530
 15M  C3   H31   single    0.970  0.020  1.090
 15M  C3   H32   single    0.970  0.020  1.090
 15M  C4   C5    single    1.501  0.020  1.501
 15M  C4   H41   single    0.970  0.020  1.090
 15M  C4   H42   single    0.970  0.020  1.090
 15M  C5   C6    double    1.333  0.020  1.333
 15M  C5   H5    single    0.930  0.020  1.080
 15M  C6   C7    single    1.502  0.020  1.502
 15M  C6   H6    single    0.930  0.020  1.080
 15M  C7   C8    single    1.526  0.020  1.526
 15M  C7   H71   single    0.970  0.020  1.090
 15M  C7   H72   single    0.970  0.020  1.090
 15M  C8   C9    single    1.526  0.020  1.526
 15M  C8   C12   single    1.534  0.020  1.534
 15M  C8   H8    single    0.970  0.020  1.090
 15M  C9   C10   single    1.534  0.020  1.534
 15M  C9   O9    single    1.413  0.020  1.413
 15M  C9   H9    single    0.970  0.020  1.090
 15M  C10  C11   single    1.549  0.020  1.549
 15M  C10  H101  single    0.970  0.020  1.090
 15M  C10  H102  single    0.970  0.020  1.090
 15M  C11  C12   single    1.535  0.020  1.535
 15M  C11  O11   single    1.409  0.020  1.409
 15M  C11  H11   single    0.970  0.020  1.090
 15M  C12  C13   single    1.493  0.020  1.493
 15M  C12  H12   single    0.970  0.020  1.090
 15M  C13  C14   double    1.328  0.020  1.328
 15M  C13  H13   single    0.930  0.020  1.080
 15M  C14  C15   single    1.502  0.020  1.502
 15M  C14  H14   single    0.930  0.020  1.080
 15M  C15  C16   single    1.530  0.020  1.530
 15M  C15  O15   single    1.411  0.020  1.411
 15M  C15  H15   single    0.970  0.020  1.090
 15M  C16  C17   single    1.529  0.020  1.529
 15M  C16  H161  single    0.970  0.020  1.090
 15M  C16  H162  single    0.970  0.020  1.090
 15M  C17  C18   single    1.503  0.020  1.503
 15M  C17  H171  single    0.970  0.020  1.090
 15M  C17  H172  single    0.970  0.020  1.090
 15M  C18  C19   aromatic  1.393  0.020  1.393
 15M  C18  C23   aromatic  1.394  0.020  1.394
 15M  C19  C20   aromatic  1.389  0.020  1.389
 15M  C19  H19   single    0.930  0.020  1.080
 15M  C20  C21   aromatic  1.388  0.020  1.388
 15M  C20  H20   single    0.930  0.020  1.080
 15M  C21  C22   aromatic  1.390  0.020  1.390
 15M  C21  H21   single    0.930  0.020  1.080
 15M  C22  C23   aromatic  1.388  0.020  1.388
 15M  C22  H22   single    0.930  0.020  1.080
 15M  C23  H23   single    0.930  0.020  1.080
 15M  C24  C25   single    1.517  0.020  1.517
 15M  C24  H241  single    0.970  0.020  1.090
 15M  C24  H242  single    0.970  0.020  1.090
 15M  C24  H243  single    0.970  0.020  1.090
 15M  C25  N     single    1.449  0.020  1.449
 15M  C25  H251  single    0.970  0.020  1.090
 15M  C25  H252  single    0.970  0.020  1.090
 15M  N    HN    single    0.860  0.020  1.020
 15M  O9   HO9   single    0.850  0.020  0.980
 15M  O11  H1    single    0.850  0.020  0.980
 15M  O15  H2    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
 15M  O1    C1   N     122.64  3.000
 15M  O1    C1   C2    121.87  3.000
 15M  N     C1   C2    115.49  3.000
 15M  H22A  C2   H21A  106.64  3.000
 15M  H22A  C2   C3    109.73  3.000
 15M  H21A  C2   C3    109.21  3.000
 15M  H22A  C2   C1    108.09  3.000
 15M  H21A  C2   C1    110.80  3.000
 15M  C3    C2   C1    112.22  3.000
 15M  H32   C3   H31   106.61  3.000
 15M  H32   C3   C4    109.26  3.000
 15M  H31   C3   C4    110.30  3.000
 15M  H32   C3   C2    109.32  3.000
 15M  H31   C3   C2    110.43  3.000
 15M  C4    C3   C2    110.82  3.000
 15M  H42   C4   H41   105.91  3.000
 15M  H42   C4   C5    109.51  3.000
 15M  H41   C4   C5    109.95  3.000
 15M  H42   C4   C3    109.12  3.000
 15M  H41   C4   C3    108.37  3.000
 15M  C5    C4   C3    113.69  3.000
 15M  H5    C5   C6    118.77  3.000
 15M  H5    C5   C4    116.87  3.000
 15M  C6    C5   C4    124.36  3.000
 15M  H6    C6   C7    117.22  3.000
 15M  H6    C6   C5    118.60  3.000
 15M  C7    C6   C5    124.18  3.000
 15M  H72   C7   H71   105.76  3.000
 15M  H72   C7   C8    107.69  3.000
 15M  H71   C7   C8    109.71  3.000
 15M  H72   C7   C6    109.68  3.000
 15M  H71   C7   C6    110.06  3.000
 15M  C8    C7   C6    113.62  3.000
 15M  H8    C8   C12   107.45  3.000
 15M  H8    C8   C9    106.18  3.000
 15M  C12   C8   C9    103.25  3.000
 15M  H8    C8   C7    108.21  3.000
 15M  C12   C8   C7    114.09  3.000
 15M  C9    C8   C7    117.04  3.000
 15M  H9    C9   O9    110.44  3.000
 15M  H9    C9   C10   111.45  3.000
 15M  O9    C9   C10   112.47  3.000
 15M  H9    C9   C8    111.47  3.000
 15M  O9    C9   C8    108.18  3.000
 15M  C10   C9   C8    102.55  3.000
 15M  H102  C10  H101  106.74  3.000
 15M  H102  C10  C11   111.73  3.000
 15M  H101  C10  C11   110.12  3.000
 15M  H102  C10  C9    111.81  3.000
 15M  H101  C10  C9    109.77  3.000
 15M  C11   C10  C9    106.70  3.000
 15M  H11   C11  O11   109.89  3.000
 15M  H11   C11  C12   108.52  3.000
 15M  O11   C11  C12   109.32  3.000
 15M  H11   C11  C10   108.33  3.000
 15M  O11   C11  C10   115.09  3.000
 15M  C12   C11  C10   105.44  3.000
 15M  H12   C12  C13   109.51  3.000
 15M  H12   C12  C11   108.14  3.000
 15M  C13   C12  C11   114.49  3.000
 15M  H12   C12  C8    108.67  3.000
 15M  C13   C12  C8    112.82  3.000
 15M  C11   C12  C8    102.86  3.000
 15M  H13   C13  C14   120.02  3.000
 15M  H13   C13  C12   115.43  3.000
 15M  C14   C13  C12   124.51  3.000
 15M  H14   C14  C15   114.26  3.000
 15M  H14   C14  C13   119.11  3.000
 15M  C15   C14  C13   126.63  3.000
 15M  H15   C15  O15   105.07  3.000
 15M  H15   C15  C16   107.72  3.000
 15M  O15   C15  C16   112.08  3.000
 15M  H15   C15  C14   107.52  3.000
 15M  O15   C15  C14   113.83  3.000
 15M  C16   C15  C14   110.22  3.000
 15M  H162  C16  H161  106.10  3.000
 15M  H162  C16  C17   109.29  3.000
 15M  H161  C16  C17   109.99  3.000
 15M  H162  C16  C15   108.35  3.000
 15M  H161  C16  C15   109.34  3.000
 15M  C17   C16  C15   113.50  3.000
 15M  H172  C17  H171  106.67  3.000
 15M  H172  C17  C18   109.89  3.000
 15M  H171  C17  C18   109.64  3.000
 15M  H172  C17  C16   109.79  3.000
 15M  H171  C17  C16   109.00  3.000
 15M  C18   C17  C16   111.71  3.000
 15M  C23   C18  C19   118.33  3.000
 15M  C23   C18  C17   120.55  3.000
 15M  C19   C18  C17   121.09  3.000
 15M  H19   C19  C20   119.58  3.000
 15M  H19   C19  C18   119.46  3.000
 15M  C20   C19  C18   120.96  3.000
 15M  H20   C20  C21   120.09  3.000
 15M  H20   C20  C19   119.77  3.000
 15M  C21   C20  C19   120.13  3.000
 15M  H21   C21  C22   120.22  3.000
 15M  H21   C21  C20   120.31  3.000
 15M  C22   C21  C20   119.47  3.000
 15M  H22   C22  C23   119.81  3.000
 15M  H22   C22  C21   120.04  3.000
 15M  C23   C22  C21   120.15  3.000
 15M  H23   C23  C22   119.56  3.000
 15M  H23   C23  C18   119.48  3.000
 15M  C22   C23  C18   120.96  3.000
 15M  H243  C24  H242  108.03  3.000
 15M  H243  C24  H241  107.75  3.000
 15M  H242  C24  H241  107.83  3.000
 15M  H243  C24  C25   111.35  3.000
 15M  H242  C24  C25   111.63  3.000
 15M  H241  C24  C25   110.11  3.000
 15M  H252  C25  H251  106.68  3.000
 15M  H252  C25  N     109.54  3.000
 15M  H251  C25  N     110.14  3.000
 15M  H252  C25  C24   109.82  3.000
 15M  H251  C25  C24   109.95  3.000
 15M  N     C25  C24   110.63  3.000
 15M  HN    N    C25   118.23  3.000
 15M  HN    N    C1    118.88  3.000
 15M  C25   N    C1    122.79  3.000
 15M  HO9   O9   C9    108.11  3.000
 15M  H1    O11  C11   108.21  3.000
 15M  H2    O15  C15   109.40  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
 15M  CONST_01  C21   C20  C19  C18     0.00   0.0  0
 15M  CONST_02  C21   C22  C23  C18     0.00   0.0  0
 15M  CONST_03  C22   C23  C18  C19     0.00   0.0  0
 15M  CONST_04  C22   C21  C20  C19     0.00   0.0  0
 15M  CONST_05  C23   C18  C19  C20     0.00   0.0  0
 15M  CONST_06  C23   C22  C21  C20     0.00   0.0  0
 15M  CONST_07  C20   C19  C18  C17   180.00   0.0  0
 15M  CONST_08  C22   C23  C18  C17   180.00   0.0  0
 15M  CONST_09  H20   C20  C19  C18   180.00   0.0  0
 15M  CONST_10  H22   C22  C23  C18   180.00   0.0  0
 15M  CONST_11  H23   C23  C18  C19   180.00   0.0  0
 15M  CONST_12  H21   C21  C20  C19   180.00   0.0  0
 15M  CONST_13  H19   C19  C20  C21   180.00   0.0  0
 15M  CONST_14  C25   N    C1   C2    180.00   0.0  0
 15M  CONST_15  O1    C1   N    C25     0.00   0.0  0
 15M  CONST_16  HN    N    C1   C2      0.00   0.0  0
 15M  Var_01    C19   C18  C17  C16   -96.84  30.0  2
 15M  Var_02    C15   C14  C13  C12   178.69   0.0  2
 15M  Var_03    C8    C7   C6   C5     81.34  30.0  3
 15M  Var_04    C18   C17  C16  C15  -176.95  30.0  3
 15M  Var_05    C7    C6   C5   C4     -0.40   0.0  2
 15M  Var_06    C4    C3   C2   C1    175.45  30.0  3
 15M  Var_07    C24   C25  N    C1   -172.13  30.0  2
 15M  Var_08    C5    C4   C3   C2   -171.79  30.0  3
 15M  Var_09    N     C1   C2   C3   -121.20  30.0  2
 15M  Var_10    C6    C5   C4   C3     90.38  30.0  3
 15M  Var_11    H241  C24  C25  N    -177.85  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
 15M  chir_01  C8   C7   C9   C12  negativ
 15M  chir_02  C9   O9   C8   C10  positiv
 15M  chir_03  C11  O11  C12  C10  negativ
 15M  chir_04  C12  C8   C11  C13  positiv
 15M  chir_05  C15  O15  C16  C14  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
 15M  plan-1  C17  0.020
 15M  plan-1  C18  0.020
 15M  plan-1  C19  0.020
 15M  plan-1  C20  0.020
 15M  plan-1  C21  0.020
 15M  plan-1  C22  0.020
 15M  plan-1  C23  0.020
 15M  plan-1  H19  0.020
 15M  plan-1  H20  0.020
 15M  plan-1  H21  0.020
 15M  plan-1  H22  0.020
 15M  plan-1  H23  0.020
 15M  plan-2  C1   0.020
 15M  plan-2  C2   0.020
 15M  plan-2  C25  0.020
 15M  plan-2  N    0.020
 15M  plan-2  O1   0.020
 15M  plan-2  HN   0.020
 15M  plan-3  C4   0.020
 15M  plan-3  C5   0.020
 15M  plan-3  C6   0.020
 15M  plan-3  C7   0.020
 15M  plan-3  H5   0.020
 15M  plan-3  H6   0.020
 15M  plan-4  C12  0.020
 15M  plan-4  C13  0.020
 15M  plan-4  C14  0.020
 15M  plan-4  C15  0.020
 15M  plan-4  H13  0.020
 15M  plan-4  H14  0.020

