# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed May  6 18:49:24 2020
#   Inital geometry file: a 105 line input string
#   Ligand name: (2R,3S,4R)-2-[(S)-(1S)-cyclohex-2-en-1-yl(hydroxy)methyl]-3-hydroxy-4-(2-hydroxyethyl)-3-methyl-5-oxopyrrolidine-2-carbaldehyde
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@]1(O)[C@@H](CCO)C(=O)N[C@]1(C=O)[C@@H](O)[C@H]2CCCC=C2
#
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
 HYE  HYE  (2R,3S,4R)-2-[(S)-(1S)-cyclohex-2-en-1-yl(hydroxy)methyl]-3-hydroxy-4-(2-hydroxyethyl)-3-methyl-5-oxopyrrolidine-2-carbaldehyde  ligand  44  21  .  2021-08-11  2021-08-11  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_HYE
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
 HYE  C1    C  CH2   0  -0.140   4.2973   1.2989   0.7315
 HYE  C2    C  CH2   0  -0.484   3.6322   0.0243   0.2427
 HYE  C3    C  CH1   0  -0.402   2.1124   0.1530   0.2140
 HYE  C4    C  CT    0   0.229   1.3412  -1.1757   0.2437
 HYE  C6    C  CH3   0  -0.700   1.2361  -1.8048   1.6184
 HYE  O21   O  OH1   0  -0.675   5.6927   1.0901   0.7641
 HYE  C19   C  C     0   0.576   1.5714   0.8248  -1.0323
 HYE  O20   O  O     0  -0.470   2.0920   1.7234  -1.6655
 HYE  N18   N  NH1   0  -0.669   0.3886   0.2449  -1.3282
 HYE  C7    C  CT    0  -0.009  -0.0268  -0.8094  -0.4348
 HYE  C16   C  C1    0   0.192  -0.4833  -2.0314  -1.2201
 HYE  O17   O  O     0  -0.367  -1.0462  -2.9656  -0.7123
 HYE  C8    C  CH1   0   0.056  -1.1299  -0.3683   0.5593
 HYE  O15   O  OH1   0  -0.650  -0.6963   0.6979   1.3627
 HYE  C9    C  CH1   0  -0.296  -2.5089  -0.0679  -0.0737
 HYE  C14   C  CH2   0  -0.440  -3.5944  -0.2531   0.9920
 HYE  C13   C  CH2   0  -0.450  -4.9397   0.2902   0.5332
 HYE  C12   C  CH2   0  -0.474  -4.8520   1.7887   0.2759
 HYE  C11   C  C1    0  -0.220  -3.6237   2.1364  -0.5043
 HYE  C10   C  C1    0  -0.245  -2.5929   1.3114  -0.6783
 HYE  O5    O  OH1   0  -0.668   1.9307  -2.0820  -0.6752
 HYE  H1    H  HCH2  0   0.203   4.0310   2.1317   0.0713
 HYE  H1A   H  HCH2  0   0.190   3.9054   1.5416   1.7288
 HYE  H2    H  HCH2  0   0.243   4.0212  -0.2397  -0.7435
 HYE  H2A   H  HCH2  0   0.243   3.9134  -0.7853   0.9235
 HYE  H3    H  HCH1  0   0.291   1.7890   0.7533   1.0707
 HYE  H6    H  HCH3  0   0.251   0.8150  -1.1200   2.3513
 HYE  H6A   H  HCH3  0   0.251   0.6271  -2.7094   1.5946
 HYE  H6B   H  HCH3  0   0.249   2.2300  -2.0877   1.9739
 HYE  HO21  H  HOH1  0   0.454   6.1103   1.9060   1.0536
 HYE  HN18  H  HNH1  0   0.401  -0.1510   0.5414  -2.1280
 HYE  H16   H  H     0   0.218  -0.2716  -1.9993  -2.3036
 HYE  H8    H  HCH1  0   0.256  -1.2762  -1.2134   1.2375
 HYE  HO15  H  HOH1  0   0.457  -0.8040   1.5245   0.8781
 HYE  H9    H  HCH1  0   0.253  -2.6910  -0.8017  -0.8683
 HYE  H14   H  HCH2  0   0.238  -3.6760  -1.3135   1.2411
 HYE  H14A  H  HCH2  0   0.226  -3.2905   0.2651   1.9070
 HYE  H13   H  HCH2  0   0.221  -5.2443  -0.2209  -0.3852
 HYE  H13A  H  HCH2  0   0.236  -5.7082   0.0781   1.2791
 HYE  H12   H  HCH2  0   0.242  -5.7366   2.1417  -0.2609
 HYE  H12A  H  HCH2  0   0.238  -4.8479   2.3410   1.2227
 HYE  H11   H  H     0   0.242  -3.5897   3.1171  -0.9675
 HYE  H10   H  H     0   0.239  -1.7765   1.6557  -1.3037
 HYE  HO5   H  HOH1  0   0.463   2.7323  -2.4500  -0.2867

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
 HYE  C1   C2    single  1.519  0.020  1.519
 HYE  C1   O21   single  1.411  0.020  1.411
 HYE  C2   C3    single  1.525  0.020  1.525
 HYE  C3   C4    single  1.537  0.020  1.537
 HYE  C3   C19   single  1.516  0.020  1.516
 HYE  C4   C6    single  1.515  0.020  1.515
 HYE  C4   C7    single  1.570  0.020  1.570
 HYE  C4   O5    single  1.419  0.020  1.419
 HYE  C19  O20   double  1.216  0.020  1.216
 HYE  C19  N18   single  1.350  0.020  1.350
 HYE  N18  C7    single  1.443  0.020  1.443
 HYE  C7   C16   single  1.523  0.020  1.523
 HYE  C7   C8    single  1.549  0.020  1.549
 HYE  C16  O17   double  1.203  0.020  1.203
 HYE  C8   O15   single  1.404  0.020  1.404
 HYE  C8   C9    single  1.547  0.020  1.547
 HYE  C9   C14   single  1.532  0.020  1.532
 HYE  C9   C10   single  1.508  0.020  1.508
 HYE  C14  C13   single  1.522  0.020  1.522
 HYE  C13  C12   single  1.523  0.020  1.523
 HYE  C12  C11   single  1.496  0.020  1.496
 HYE  C11  C10   double  1.332  0.020  1.332
 HYE  C1   H1    single  0.970  0.020  1.090
 HYE  C1   H1A   single  0.970  0.020  1.090
 HYE  C2   H2    single  0.970  0.020  1.090
 HYE  C2   H2A   single  0.970  0.020  1.090
 HYE  C3   H3    single  0.970  0.020  1.090
 HYE  C6   H6    single  0.970  0.020  1.090
 HYE  C6   H6A   single  0.970  0.020  1.090
 HYE  C6   H6B   single  0.970  0.020  1.090
 HYE  O21  HO21  single  0.850  0.020  0.980
 HYE  N18  HN18  single  0.860  0.020  1.020
 HYE  C16  H16   single  0.930  0.020  1.080
 HYE  C8   H8    single  0.970  0.020  1.090
 HYE  O15  HO15  single  0.850  0.020  0.980
 HYE  C9   H9    single  0.970  0.020  1.090
 HYE  C14  H14   single  0.970  0.020  1.090
 HYE  C14  H14A  single  0.970  0.020  1.090
 HYE  C13  H13   single  0.970  0.020  1.090
 HYE  C13  H13A  single  0.970  0.020  1.090
 HYE  C12  H12   single  0.970  0.020  1.090
 HYE  C12  H12A  single  0.970  0.020  1.090
 HYE  C11  H11   single  0.930  0.020  1.080
 HYE  C10  H10   single  0.930  0.020  1.080
 HYE  O5   HO5   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
 HYE  H1A   C1   H1   107.00  3.000
 HYE  H1A   C1   O21  111.37  3.000
 HYE  H1    C1   O21  111.51  3.000
 HYE  H1A   C1   C2   108.74  3.000
 HYE  H1    C1   C2   109.73  3.000
 HYE  O21   C1   C2   108.44  3.000
 HYE  H2A   C2   H2   106.93  3.000
 HYE  H2A   C2   C3   109.27  3.000
 HYE  H2    C2   C3   110.99  3.000
 HYE  H2A   C2   C1   107.94  3.000
 HYE  H2    C2   C1   109.72  3.000
 HYE  C3    C2   C1   111.82  3.000
 HYE  H3    C3   C19  107.15  3.000
 HYE  H3    C3   C4   108.10  3.000
 HYE  C19   C3   C4   102.71  3.000
 HYE  H3    C3   C2   109.01  3.000
 HYE  C19   C3   C2   114.11  3.000
 HYE  C4    C3   C2   115.26  3.000
 HYE  O5    C4   C7   103.36  3.000
 HYE  O5    C4   C6   110.56  3.000
 HYE  C7    C4   C6   115.36  3.000
 HYE  O5    C4   C3   109.35  3.000
 HYE  C7    C4   C3   103.13  3.000
 HYE  C6    C4   C3   114.29  3.000
 HYE  H6B   C6   H6A  107.47  3.000
 HYE  H6B   C6   H6   107.21  3.000
 HYE  H6A   C6   H6   108.70  3.000
 HYE  H6B   C6   C4   109.84  3.000
 HYE  H6A   C6   C4   111.30  3.000
 HYE  H6    C6   C4   112.13  3.000
 HYE  HO21  O21  C1   108.12  3.000
 HYE  N18   C19  O20  125.32  3.000
 HYE  N18   C19  C3   107.61  3.000
 HYE  O20   C19  C3   127.07  3.000
 HYE  HN18  N18  C7   123.46  3.000
 HYE  HN18  N18  C19  121.05  3.000
 HYE  C7    N18  C19  115.49  3.000
 HYE  C8    C7   C16  110.25  3.000
 HYE  C8    C7   N18  113.22  3.000
 HYE  C16   C7   N18  110.70  3.000
 HYE  C8    C7   C4   114.17  3.000
 HYE  C16   C7   C4   107.27  3.000
 HYE  N18   C7   C4   100.79  3.000
 HYE  H16   C16  O17  121.76  3.000
 HYE  H16   C16  C7   115.16  3.000
 HYE  O17   C16  C7   123.08  3.000
 HYE  H8    C8   C9   106.54  3.000
 HYE  H8    C8   O15  105.87  3.000
 HYE  C9    C8   O15  111.23  3.000
 HYE  H8    C8   C7   105.85  3.000
 HYE  C9    C8   C7   115.31  3.000
 HYE  O15   C8   C7   111.32  3.000
 HYE  HO15  O15  C8   109.20  3.000
 HYE  H9    C9   C10  108.19  3.000
 HYE  H9    C9   C14  107.78  3.000
 HYE  C10   C9   C14  110.48  3.000
 HYE  H9    C9   C8   108.33  3.000
 HYE  C10   C9   C8   113.04  3.000
 HYE  C14   C9   C8   108.87  3.000
 HYE  H14A  C14  H14  106.84  3.000
 HYE  H14A  C14  C13  109.18  3.000
 HYE  H14   C14  C13  110.44  3.000
 HYE  H14A  C14  C9   109.11  3.000
 HYE  H14   C14  C9   109.20  3.000
 HYE  C13   C14  C9   111.93  3.000
 HYE  H13A  C13  H13  106.67  3.000
 HYE  H13A  C13  C12  110.31  3.000
 HYE  H13   C13  C12  109.50  3.000
 HYE  H13A  C13  C14  110.30  3.000
 HYE  H13   C13  C14  109.41  3.000
 HYE  C12   C13  C14  110.57  3.000
 HYE  H12A  C12  H12  105.34  3.000
 HYE  H12A  C12  C11  109.28  3.000
 HYE  H12   C12  C11  109.46  3.000
 HYE  H12A  C12  C13  110.49  3.000
 HYE  H12   C12  C13  110.74  3.000
 HYE  C11   C12  C13  111.35  3.000
 HYE  H11   C11  C10  118.68  3.000
 HYE  H11   C11  C12  117.28  3.000
 HYE  C10   C11  C12  124.04  3.000
 HYE  H10   C10  C11  117.48  3.000
 HYE  H10   C10  C9   118.65  3.000
 HYE  C11   C10  C9   123.86  3.000
 HYE  HO5   O5   C4   109.17  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
 HYE  CONST_01  C7    N18  C19  C3     0.00   0.0  0
 HYE  CONST_02  C7    N18  C19  O20  180.00   0.0  0
 HYE  CONST_03  HN18  N18  C19  C3   180.00   0.0  0
 HYE  Var_01    C12   C13  C14  C9   -61.96  30.0  1
 HYE  Var_02    C12   C11  C10  C9    -2.06  30.0  1
 HYE  Var_03    C11   C12  C13  C14   45.29  30.0  1
 HYE  Var_04    C10   C11  C12  C13  -14.68  30.0  1
 HYE  Var_05    O21   C1   C2   C3   178.44  30.0  1

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
 HYE  chir_01  C3  C2   C4   C19  positiv
 HYE  chir_02  C4  C3   C6   C7   negativ
 HYE  chir_03  C7  N18  C16  C4   negativ
 HYE  chir_04  C8  O15  C7   C9   positiv
 HYE  chir_05  C9  C10  C14  C8   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
 HYE  plan-1  C3    0.020
 HYE  plan-1  C19   0.020
 HYE  plan-1  O20   0.020
 HYE  plan-1  N18   0.020
 HYE  plan-1  C7    0.020
 HYE  plan-1  HN18  0.020
 HYE  plan-2  C7    0.020
 HYE  plan-2  C16   0.020
 HYE  plan-2  O17   0.020
 HYE  plan-2  H16   0.020

