# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version 1.18.1-3865-
#   - file written: Wed Jun 10 08:40:21 2020
#   Inital geometry file: a 163 line input string
#   Ligand name: benzyl N-{[(2S,3S)-3-(propylcarbamoyl)oxiran-2-yl]carbonyl}-L-isoleucyl-L-prolinate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCNC(=O)[C@H]1O[C@@H]1C(=O)N[C@@H]([C@@H](C)CC)C(=O)N2CCC[C@H]2C(=O)OCc3ccccc3
#
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
 73V  73V  'benzyl N-{[(2S,3S)-3-(propylcarbamoyl)oxiran-2-yl]carbonyl}-L-isoleucyl-L-prolinate'  ligand  69  34  .  2022-09-16  2023-02-02
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_73V
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
 73V  C19   C  CH3   0  -0.666   4.1555   6.7778  -1.5253
 73V  C18   C  CH2   0  -0.465   3.9932   5.2694  -1.6411
 73V  C17   C  CH2   0  -0.242   4.9120   4.5308  -0.6807
 73V  N3    N  NH1   0  -0.649   4.7629   3.0958  -0.8179
 73V  C10   C  CR6   0   0.079  -5.3983   1.5402   0.9926
 73V  C15   C  CR16  0  -0.292  -4.8270   2.7775   1.2740
 73V  C14   C  CR16  0  -0.242  -5.4416   3.9490   0.8530
 73V  C13   C  CR16  0  -0.260  -6.6345   3.8916   0.1442
 73V  C12   C  CR16  0  -0.242  -7.2105   2.6601  -0.1420
 73V  C11   C  CR16  0  -0.287  -6.5935   1.4911   0.2807
 73V  C9    C  CH2   0  -0.255  -4.7211   0.2755   1.4205
 73V  O1    O  O2    0  -0.442   5.4602  -0.1649   0.5427
 73V  C3    C  CH1   0  -0.147   4.0798  -0.0653   0.7691
 73V  C4    C  C     0   0.575   3.2555  -1.2138   0.2535
 73V  O4    O  O     0  -0.479   3.6628  -1.9383  -0.6380
 73V  C2    C  CH1   0  -0.146   4.7623   0.7903  -0.2117
 73V  C16   C  C     0   0.565   5.0237   2.2258   0.1615
 73V  O2    O  O     0  -0.489   5.4101   2.5310   1.2785
 73V  N1    N  NH1   0  -0.642   2.0611  -1.3248   0.8518
 73V  C5    C  CH1   0  -0.224   1.0696  -2.3017   0.4793
 73V  C6    C  C     0   0.589  -0.2464  -1.5852   0.1946
 73V  O5    O  O     0  -0.492  -0.4646  -0.4586   0.6223
 73V  C20   C  CH1   0  -0.220   0.9025  -3.4071   1.5480
 73V  C22   C  CH2   0  -0.436   0.3158  -2.8689   2.8555
 73V  C21   C  CH3   0  -0.671   2.2299  -4.1277   1.7571
 73V  C23   C  CH3   0  -0.670   0.1218  -3.9405   3.9210
 73V  N2    N  NR5   0  -0.483  -1.1688  -2.2504  -0.5171
 73V  C7    C  CR15  0  -0.155  -2.4436  -1.6112  -0.7894
 73V  C8    C  C     0   0.602  -3.1652  -1.2404   0.4892
 73V  O7    O  O2    0  -0.450  -3.8890  -0.1458   0.3243
 73V  O6    O  O     0  -0.443  -3.1408  -1.8963   1.4982
 73V  C26   C  CH2   0  -0.483  -3.2224  -2.6795  -1.5714
 73V  C25   C  CH2   0  -0.474  -2.1170  -3.4593  -2.2723
 73V  C24   C  CH2   0  -0.284  -1.0239  -3.5256  -1.2157
 73V  H191  H  HCH3  0   0.224   5.1775   7.0858  -1.7517
 73V  H192  H  HCH3  0   0.237   3.4936   7.2954  -2.2189
 73V  H193  H  HCH3  0   0.224   3.9194   7.1270  -0.5189
 73V  H181  H  HCH2  0   0.233   2.9574   4.9874  -1.4365
 73V  H182  H  HCH2  0   0.230   4.2091   4.9565  -2.6668
 73V  H171  H  HCH2  0   0.235   5.9519   4.8208  -0.8631
 73V  H172  H  HCH2  0   0.242   4.6780   4.8090   0.3475
 73V  HN3   H  HNH1  0   0.406   4.5086   2.7399  -1.7265
 73V  H15   H  HCR6  0   0.256  -3.8990   2.8272   1.8316
 73V  H14   H  HCR6  0   0.259  -4.9905   4.9063   1.0792
 73V  H13   H  HCR6  0   0.260  -7.1168   4.8049  -0.1794
 73V  H12   H  HCR6  0   0.259  -8.1414   2.6104  -0.6918
 73V  H11   H  HCR6  0   0.256  -7.0480   0.5321   0.0616
 73V  H91   H  HCH2  0   0.255  -5.4502  -0.5057   1.6448
 73V  H92   H  HCH2  0   0.256  -4.1065   0.4371   2.3077
 73V  H3    H  HCH1  0   0.290   3.7887   0.3690   1.7240
 73V  H2    H  HCH1  0   0.289   4.6454   0.5611  -1.2698
 73V  HN1   H  HNH1  0   0.404   1.8092  -0.6455   1.5531
 73V  H5    H  HCH1  0   0.287   1.4250  -2.7770  -0.4364
 73V  H20   H  HCH1  0   0.241   0.1926  -4.1332   1.1374
 73V  H221  H  HCH2  0   0.213   0.9620  -2.0811   3.2562
 73V  H222  H  HCH2  0   0.243  -0.6525  -2.4050   2.6558
 73V  H211  H  HCH3  0   0.222   2.9535  -3.4903   2.2683
 73V  H212  H  HCH3  0   0.243   2.0956  -5.0230   2.3629
 73V  H213  H  HCH3  0   0.236   2.6682  -4.4397   0.8087
 73V  H231  H  HCH3  0   0.225   1.0695  -4.3450   4.2760
 73V  H232  H  HCH3  0   0.233  -0.4021  -3.5321   4.7855
 73V  H233  H  HCH3  0   0.219  -0.4731  -4.7738   3.5411
 73V  H7    H  HCR5  0   0.286  -2.3017  -0.7182  -1.4046
 73V  H261  H  HCH2  0   0.273  -3.9428  -2.2321  -2.2533
 73V  H262  H  HCH2  0   0.255  -3.7642  -3.3362  -0.8872
 73V  H251  H  HCH2  0   0.250  -1.7617  -2.9134  -3.1481
 73V  H252  H  HCH2  0   0.264  -2.4355  -4.4488  -2.5958
 73V  H241  H  HCH2  0   0.264  -0.0321  -3.6318  -1.6541
 73V  H242  H  HCH2  0   0.253  -1.1863  -4.3642  -0.5341

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
 73V  C19  C18   single    1.522  0.020  1.522
 73V  C19  H191  single    0.970  0.020  1.090
 73V  C19  H192  single    0.970  0.020  1.090
 73V  C19  H193  single    0.970  0.020  1.090
 73V  C18  C17   single    1.521  0.020  1.521
 73V  C18  H181  single    0.970  0.020  1.090
 73V  C18  H182  single    0.970  0.020  1.090
 73V  C17  N3    single    1.449  0.020  1.449
 73V  C17  H171  single    0.970  0.020  1.090
 73V  C17  H172  single    0.970  0.020  1.090
 73V  N3   C16   single    1.336  0.020  1.336
 73V  N3   HN3   single    0.860  0.020  1.020
 73V  C10  C15   aromatic  1.392  0.020  1.392
 73V  C10  C11   aromatic  1.392  0.020  1.392
 73V  C10  C9    single    1.497  0.020  1.497
 73V  C15  C14   aromatic  1.388  0.020  1.388
 73V  C15  H15   single    0.930  0.020  1.080
 73V  C14  C13   aromatic  1.389  0.020  1.389
 73V  C14  H14   single    0.930  0.020  1.080
 73V  C13  C12   aromatic  1.389  0.020  1.389
 73V  C13  H13   single    0.930  0.020  1.080
 73V  C12  C11   aromatic  1.388  0.020  1.388
 73V  C12  H12   single    0.930  0.020  1.080
 73V  C11  H11   single    0.930  0.020  1.080
 73V  C9   O7    single    1.439  0.020  1.439
 73V  C9   H91   single    0.970  0.020  1.090
 73V  C9   H92   single    0.970  0.020  1.090
 73V  O1   C3    single    1.402  0.020  1.402
 73V  O1   C2    single    1.403  0.020  1.403
 73V  C3   C4    single    1.505  0.020  1.505
 73V  C3   C2    single    1.470  0.020  1.470
 73V  C3   H3    single    0.970  0.020  1.090
 73V  C4   O4    double    1.219  0.020  1.219
 73V  C4   N1    single    1.340  0.020  1.340
 73V  C2   C16   single    1.506  0.020  1.506
 73V  C2   H2    single    0.970  0.020  1.090
 73V  C16  O2    double    1.221  0.020  1.221
 73V  N1   C5    single    1.441  0.020  1.441
 73V  N1   HN1   single    0.860  0.020  1.020
 73V  C5   C6    single    1.525  0.020  1.525
 73V  C5   C20   single    1.547  0.020  1.547
 73V  C5   H5    single    0.970  0.020  1.090
 73V  C6   O5    double    1.225  0.020  1.225
 73V  C6   N2    single    1.342  0.020  1.342
 73V  C20  C22   single    1.531  0.020  1.531
 73V  C20  C21   single    1.525  0.020  1.525
 73V  C20  H20   single    0.970  0.020  1.090
 73V  C22  C23   single    1.524  0.020  1.524
 73V  C22  H221  single    0.970  0.020  1.090
 73V  C22  H222  single    0.970  0.020  1.090
 73V  C21  H211  single    0.970  0.020  1.090
 73V  C21  H212  single    0.970  0.020  1.090
 73V  C21  H213  single    0.970  0.020  1.090
 73V  C23  H231  single    0.970  0.020  1.090
 73V  C23  H232  single    0.970  0.020  1.090
 73V  C23  H233  single    0.970  0.020  1.090
 73V  N2   C7    single    1.452  0.020  1.452
 73V  N2   C24   single    1.461  0.020  1.461
 73V  C7   C8    single    1.514  0.020  1.514
 73V  C7   C26   single    1.536  0.020  1.536
 73V  C7   H7    single    0.970  0.020  1.090
 73V  C8   O7    single    1.323  0.020  1.323
 73V  C8   O6    double    1.204  0.020  1.204
 73V  C26  C25   single    1.524  0.020  1.524
 73V  C26  H261  single    0.970  0.020  1.090
 73V  C26  H262  single    0.970  0.020  1.090
 73V  C25  C24   single    1.522  0.020  1.522
 73V  C25  H251  single    0.970  0.020  1.090
 73V  C25  H252  single    0.970  0.020  1.090
 73V  C24  H241  single    0.970  0.020  1.090
 73V  C24  H242  single    0.970  0.020  1.090

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
 73V  H193  C19  H192  107.68  3.000
 73V  H193  C19  H191  107.68  3.000
 73V  H192  C19  H191  107.63  3.000
 73V  H193  C19  C18   111.37  3.000
 73V  H192  C19  C18   110.96  3.000
 73V  H191  C19  C18   111.34  3.000
 73V  H182  C18  H181  106.79  3.000
 73V  H182  C18  C17   109.51  3.000
 73V  H181  C18  C17   109.21  3.000
 73V  H182  C18  C19   109.51  3.000
 73V  H181  C18  C19   110.05  3.000
 73V  C17   C18  C19   111.65  3.000
 73V  H172  C17  H171  107.06  3.000
 73V  H172  C17  N3    108.65  3.000
 73V  H171  C17  N3    110.14  3.000
 73V  H172  C17  C18   109.99  3.000
 73V  H171  C17  C18   109.88  3.000
 73V  N3    C17  C18   111.04  3.000
 73V  HN3   N3   C16   118.69  3.000
 73V  HN3   N3   C17   117.43  3.000
 73V  C16   N3   C17   123.74  3.000
 73V  C9    C10  C11   120.32  3.000
 73V  C9    C10  C15   120.51  3.000
 73V  C11   C10  C15   119.16  3.000
 73V  H15   C15  C14   119.77  3.000
 73V  H15   C15  C10   119.75  3.000
 73V  C14   C15  C10   120.48  3.000
 73V  H14   C14  C13   120.09  3.000
 73V  H14   C14  C15   119.90  3.000
 73V  C13   C14  C15   120.01  3.000
 73V  H13   C13  C12   120.11  3.000
 73V  H13   C13  C14   120.03  3.000
 73V  C12   C13  C14   119.86  3.000
 73V  H12   C12  C11   119.90  3.000
 73V  H12   C12  C13   120.13  3.000
 73V  C11   C12  C13   119.98  3.000
 73V  H11   C11  C12   119.83  3.000
 73V  H11   C11  C10   119.65  3.000
 73V  C12   C11  C10   120.52  3.000
 73V  H92   C9   H91   108.36  3.000
 73V  H92   C9   O7    109.69  3.000
 73V  H91   C9   O7    109.46  3.000
 73V  H92   C9   C10   111.22  3.000
 73V  H91   C9   C10   111.17  3.000
 73V  O7    C9   C10   106.92  3.000
 73V  C2    O1   C3     63.18  3.000
 73V  H3    C3   C2    118.51  3.000
 73V  H3    C3   C4    117.29  3.000
 73V  C2    C3   C4    118.03  3.000
 73V  H3    C3   O1    115.67  3.000
 73V  C2    C3   O1     58.43  3.000
 73V  C4    C3   O1    115.44  3.000
 73V  N1    C4   O4    125.10  3.000
 73V  N1    C4   C3    113.47  3.000
 73V  O4    C4   C3    121.42  3.000
 73V  H2    C2   C16   117.38  3.000
 73V  H2    C2   C3    118.44  3.000
 73V  C16   C2   C3    118.04  3.000
 73V  H2    C2   O1    115.64  3.000
 73V  C16   C2   O1    115.42  3.000
 73V  C3    C2   O1     58.38  3.000
 73V  O2    C16  C2    121.33  3.000
 73V  O2    C16  N3    124.74  3.000
 73V  C2    C16  N3    113.91  3.000
 73V  HN1   N1   C5    117.69  3.000
 73V  HN1   N1   C4    118.50  3.000
 73V  C5    N1   C4    123.63  3.000
 73V  H5    C5   C20   107.68  3.000
 73V  H5    C5   C6    109.21  3.000
 73V  C20   C5   C6    111.81  3.000
 73V  H5    C5   N1    106.74  3.000
 73V  C20   C5   N1    112.35  3.000
 73V  C6    C5   N1    108.87  3.000
 73V  N2    C6   O5    121.26  3.000
 73V  N2    C6   C5    117.34  3.000
 73V  O5    C6   C5    121.38  3.000
 73V  H20   C20  C21   107.60  3.000
 73V  H20   C20  C22   107.75  3.000
 73V  C21   C20  C22   112.49  3.000
 73V  H20   C20  C5    106.55  3.000
 73V  C21   C20  C5    109.78  3.000
 73V  C22   C20  C5    112.35  3.000
 73V  H222  C22  H221  106.54  3.000
 73V  H222  C22  C23   108.28  3.000
 73V  H221  C22  C23   108.98  3.000
 73V  H222  C22  C20   109.45  3.000
 73V  H221  C22  C20   109.84  3.000
 73V  C23   C22  C20   113.50  3.000
 73V  H213  C21  H212  107.34  3.000
 73V  H213  C21  H211  107.94  3.000
 73V  H212  C21  H211  107.54  3.000
 73V  H213  C21  C20   111.46  3.000
 73V  H212  C21  C20   110.94  3.000
 73V  H211  C21  C20   111.44  3.000
 73V  H233  C23  H232  107.44  3.000
 73V  H233  C23  H231  107.68  3.000
 73V  H232  C23  H231  107.37  3.000
 73V  H233  C23  C22   111.27  3.000
 73V  H232  C23  C22   110.63  3.000
 73V  H231  C23  C22   112.22  3.000
 73V  C24   N2   C7    112.44  3.000
 73V  C24   N2   C6    128.18  3.000
 73V  C7    N2   C6    119.01  3.000
 73V  H7    C7   C26   110.33  3.000
 73V  H7    C7   C8    109.69  3.000
 73V  C26   C7   C8    111.01  3.000
 73V  H7    C7   N2    110.55  3.000
 73V  C26   C7   N2    103.56  3.000
 73V  C8    C7   N2    111.58  3.000
 73V  O6    C8   O7    124.52  3.000
 73V  O6    C8   C7    124.38  3.000
 73V  O7    C8   C7    110.98  3.000
 73V  C8    O7   C9    117.62  3.000
 73V  H262  C26  H261  108.14  3.000
 73V  H262  C26  C25   109.90  3.000
 73V  H261  C26  C25   113.73  3.000
 73V  H262  C26  C7    110.53  3.000
 73V  H261  C26  C7    111.63  3.000
 73V  C25   C26  C7    102.85  3.000
 73V  H252  C25  H251  108.15  3.000
 73V  H252  C25  C24   112.14  3.000
 73V  H251  C25  C24   110.19  3.000
 73V  H252  C25  C26   112.93  3.000
 73V  H251  C25  C26   110.44  3.000
 73V  C24   C25  C26   102.94  3.000
 73V  H242  C24  H241  108.15  3.000
 73V  H242  C24  C25   111.09  3.000
 73V  H241  C24  C25   112.25  3.000
 73V  H242  C24  N2    110.90  3.000
 73V  H241  C24  N2    111.57  3.000
 73V  C25   C24  N2    102.87  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
 73V  CONST_01  C13   C14  C15  C10     0.00   0.0  0
 73V  CONST_02  C13   C12  C11  C10     0.00   0.0  0
 73V  CONST_03  C12   C11  C10  C15     0.00   0.0  0
 73V  CONST_04  C12   C13  C14  C15     0.00   0.0  0
 73V  CONST_05  C11   C10  C15  C14     0.00   0.0  0
 73V  CONST_06  C11   C12  C13  C14     0.00   0.0  0
 73V  CONST_07  C9    C10  C15  C14   180.00   0.0  0
 73V  CONST_08  C9    C10  C11  C12   180.00   0.0  0
 73V  CONST_09  H14   C14  C15  C10   180.00   0.0  0
 73V  CONST_10  H12   C12  C11  C10   180.00   0.0  0
 73V  CONST_11  H11   C11  C10  C15   180.00   0.0  0
 73V  CONST_12  H13   C13  C14  C15   180.00   0.0  0
 73V  CONST_13  H15   C15  C14  C13   180.00   0.0  0
 73V  CONST_14  C7    N2   C6   C5    180.00   0.0  0
 73V  CONST_15  C24   N2   C6   C5      0.00   0.0  0
 73V  CONST_16  C7    N2   C6   O5      0.00   0.0  0
 73V  CONST_17  C24   N2   C6   O5    180.00   0.0  0
 73V  CONST_18  C2    C16  N3   C17   180.00   0.0  0
 73V  CONST_19  C5    N1   C4   C3    180.00   0.0  0
 73V  CONST_20  HN1   N1   C4   C3      0.00   0.0  0
 73V  CONST_21  HN3   N3   C16  C2      0.00   0.0  0
 73V  CONST_22  O2    C16  N3   C17     0.00   0.0  0
 73V  CONST_23  C5    N1   C4   O4      0.00   0.0  0
 73V  Var_01    C26   C25  C24  N2    -33.92  30.0  1
 73V  Var_02    C25   C24  N2   C7     16.24  30.0  1
 73V  Var_03    C24   C25  C26  C7     39.12  30.0  1
 73V  Var_04    C16   C2   C3   O1   -104.08  30.0  1
 73V  Var_05    O1    C2   C16  N3    157.14  30.0  1
 73V  Var_06    O7    C9   C10  C15   -92.02  30.0  2
 73V  Var_07    O4    C4   C3   O1    -22.25  30.0  3
 73V  Var_08    C7    C8   O7   C9    175.10  30.0  1
 73V  Var_09    N3    C17  C18  C19  -179.04  30.0  3
 73V  Var_10    C16   N3   C17  C18  -154.08  30.0  3
 73V  Var_11    H191  C19  C18  C17    60.05  30.0  3
 73V  Var_12    H231  C23  C22  C20    66.66  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
 73V  chir_03  C5   N1  C6   C20  positiv
 73V  chir_04  C20  C5  C22  C21  positiv
 73V  chir_05  C7   N2  C26  C8   negativ
 73V  chir_06  C3   O1  C4   C2   both
 73V  chir_07  C2   O1  C3   C16  both

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
 73V  plan-1  C7   0.020
 73V  plan-1  C8   0.020
 73V  plan-1  O7   0.020
 73V  plan-1  O6   0.020
 73V  plan-2  C3   0.020
 73V  plan-2  C4   0.020
 73V  plan-2  O4   0.020
 73V  plan-2  N1   0.020
 73V  plan-2  C5   0.020
 73V  plan-2  HN1  0.020
 73V  plan-3  C10  0.020
 73V  plan-3  C15  0.020
 73V  plan-3  C14  0.020
 73V  plan-3  C13  0.020
 73V  plan-3  C12  0.020
 73V  plan-3  C11  0.020
 73V  plan-3  C9   0.020
 73V  plan-3  H15  0.020
 73V  plan-3  H14  0.020
 73V  plan-3  H13  0.020
 73V  plan-3  H12  0.020
 73V  plan-3  H11  0.020
 73V  plan-4  C5   0.020
 73V  plan-4  C6   0.020
 73V  plan-4  O5   0.020
 73V  plan-4  N2   0.020
 73V  plan-4  C7   0.020
 73V  plan-4  C24  0.020
 73V  plan-5  C17  0.020
 73V  plan-5  N3   0.020
 73V  plan-5  C2   0.020
 73V  plan-5  C16  0.020
 73V  plan-5  O2   0.020
 73V  plan-5  HN3  0.020

