# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Mar  8 14:11:45 2022
#   Inital geometry file: a 105 line input string
#   Ligand name: (3R,4S,5S)-4-(acetylamino)-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCC(CC)O[C@@H]1C=C(C[C@H](N)[C@@H]1NC(C)=O)C(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
 22N  22N  '(3R,4S,5S)-4-(acetylamino)-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylic acid'  ligand  43  20  .  2022-03-10  2022-03-10
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_22N
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
 22N  C1   C  C      0   0.389  -3.1531   1.5818   0.4772
 22N  O1A  O  O      0  -0.595  -2.8313   2.7585   0.7346
 22N  O1B  O  OC    -1  -0.598  -4.2804   1.0702   0.6332
 22N  C2   C  C      0  -0.094  -2.0754   0.6556  -0.0731
 22N  C3   C  CH2    0  -0.514  -2.4746  -0.7475  -0.4332
 22N  C4   C  CH1    0  -0.040  -1.3887  -1.5045  -1.1895
 22N  C5   C  CH1    0  -0.176  -0.0204  -1.2570  -0.5519
 22N  N5   N  NH1    0  -0.601   0.0086  -1.6537   0.8337
 22N  C10  C  C      0   0.521   0.7055  -2.6954   1.3100
 22N  O10  O  O      0  -0.516   1.4036  -3.4226   0.6134
 22N  C11  C  CH3    0  -0.780   0.5882  -2.9173   2.7989
 22N  C6   C  CH1    0   0.058   0.3136   0.2250  -0.7050
 22N  C7   C  C1     0  -0.290  -0.8157   1.0782  -0.1969
 22N  O7   O  O2     0  -0.504   1.5195   0.4937  -0.0282
 22N  C8   C  CH1    0   0.051   2.3330   1.5211  -0.5742
 22N  C9   C  CH2    0  -0.433   2.8972   2.3562   0.5697
 22N  C81  C  CH2    0  -0.413   3.4636   0.9336  -1.4170
 22N  C82  C  CH3    0  -0.686   3.0241   0.0932  -2.6078
 22N  C91  C  CH3    0  -0.670   1.8459   3.0805   1.3968
 22N  N4   N  NH2    0  -0.795  -1.6912  -2.9243  -1.2002
 22N  H2   H  HCH2   0   0.229  -2.7404  -1.3049   0.4726
 22N  H3   H  HCH2   0   0.245  -3.3877  -0.7282  -1.0340
 22N  H4   H  HCH1   0   0.207  -1.3296  -1.0802  -2.2052
 22N  H5   H  HCH1   0   0.263   0.7360  -1.8455  -1.0747
 22N  H6   H  HNH1   0   0.396  -0.5264  -1.1024   1.4858
 22N  H7   H  HCH3   0   0.245  -0.1141  -2.2456   3.2888
 22N  H8   H  HCH3   0   0.261   0.2741  -3.9431   2.9894
 22N  H9   H  HCH3   0   0.263   1.5670  -2.7868   3.2613
 22N  H10  H  HCH1   0   0.232   0.4370   0.4148  -1.7808
 22N  H11  H  H      0   0.244  -0.5808   2.1015   0.0755
 22N  H12  H  HCH1   0   0.199   1.7247   2.1793  -1.2137
 22N  H13  H  HCH2   0   0.217   3.5029   1.7126   1.2159
 22N  H14  H  HCH2   0   0.219   3.5860   3.0868   0.1374
 22N  H15  H  HCH2   0   0.216   4.0735   1.7680  -1.7749
 22N  H16  H  HCH2   0   0.215   4.1128   0.3381  -0.7670
 22N  H17  H  HCH3   0   0.226   2.5056  -0.8149  -2.2989
 22N  H18  H  HCH3   0   0.219   2.3604   0.6492  -3.2730
 22N  H19  H  HCH3   0   0.236   3.8890  -0.2183  -3.1948
 22N  H20  H  HCH3   0   0.215   1.2417   3.7439   0.7750
 22N  H21  H  HCH3   0   0.225   1.1706   2.3824   1.8909
 22N  H22  H  HCH3   0   0.230   2.3142   3.6922   2.1687
 22N  H23  H  HNH2   0   0.343  -2.6020  -3.0653  -1.6212
 22N  H24  H  HNH2   0   0.341  -1.0360  -3.4058  -1.8042

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
 22N  C81  C82  single  1.522  0.020  1.522
 22N  C81  C8   single  1.528  0.020  1.528
 22N  C9   C8   single  1.524  0.020  1.524
 22N  C9   C91  single  1.521  0.020  1.521
 22N  C8   O7   single  1.420  0.020  1.420
 22N  O7   C6   single  1.409  0.020  1.409
 22N  C6   C7   single  1.504  0.020  1.504
 22N  C6   C5   single  1.527  0.020  1.527
 22N  C7   C2   double  1.334  0.020  1.334
 22N  C5   C4   single  1.530  0.020  1.530
 22N  C5   N5   single  1.442  0.020  1.442
 22N  O1A  C1   deloc   1.247  0.020  1.247
 22N  C2   C1   single  1.524  0.020  1.524
 22N  C2   C3   single  1.503  0.020  1.503
 22N  C4   C3   single  1.525  0.020  1.525
 22N  C4   N4   single  1.452  0.020  1.452
 22N  C1   O1B  deloc   1.248  0.020  1.248
 22N  O10  C10  double  1.225  0.020  1.225
 22N  N5   C10  single  1.341  0.020  1.341
 22N  C10  C11  single  1.510  0.020  1.510
 22N  C3   H2   single  0.970  0.020  1.090
 22N  C3   H3   single  0.970  0.020  1.090
 22N  C4   H4   single  0.970  0.020  1.090
 22N  C5   H5   single  0.970  0.020  1.090
 22N  N5   H6   single  0.860  0.020  1.020
 22N  C11  H7   single  0.970  0.020  1.090
 22N  C11  H8   single  0.970  0.020  1.090
 22N  C11  H9   single  0.970  0.020  1.090
 22N  C6   H10  single  0.970  0.020  1.090
 22N  C7   H11  single  0.930  0.020  1.080
 22N  C8   H12  single  0.970  0.020  1.090
 22N  C9   H13  single  0.970  0.020  1.090
 22N  C9   H14  single  0.970  0.020  1.090
 22N  C81  H15  single  0.970  0.020  1.090
 22N  C81  H16  single  0.970  0.020  1.090
 22N  C82  H17  single  0.970  0.020  1.090
 22N  C82  H18  single  0.970  0.020  1.090
 22N  C82  H19  single  0.970  0.020  1.090
 22N  C91  H20  single  0.970  0.020  1.090
 22N  C91  H21  single  0.970  0.020  1.090
 22N  C91  H22  single  0.970  0.020  1.090
 22N  N4   H23  single  0.890  0.020  1.040
 22N  N4   H24  single  0.890  0.020  1.040

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
 22N  C2   C1   O1B  115.78  3.000
 22N  O1B  C1   O1A  126.47  3.000
 22N  C2   C1   O1A  117.76  3.000
 22N  C7   C2   C3   121.62  3.000
 22N  C3   C2   C1   117.79  3.000
 22N  C7   C2   C1   120.57  3.000
 22N  H3   C3   H2   105.10  3.000
 22N  H3   C3   C4   109.33  3.000
 22N  H2   C3   C4   109.28  3.000
 22N  H3   C3   C2   109.70  3.000
 22N  H2   C3   C2   109.95  3.000
 22N  C4   C3   C2   113.16  3.000
 22N  H4   C4   N4   112.38  3.000
 22N  H4   C4   C5   105.89  3.000
 22N  N4   C4   C5   110.35  3.000
 22N  H4   C4   C3   107.71  3.000
 22N  N4   C4   C3   109.93  3.000
 22N  C5   C4   C3   110.49  3.000
 22N  H5   C5   C6   108.89  3.000
 22N  H5   C5   N5   107.33  3.000
 22N  C6   C5   N5   111.04  3.000
 22N  H5   C5   C4   109.45  3.000
 22N  N5   C5   C4   111.97  3.000
 22N  C6   C5   C4   108.12  3.000
 22N  H6   N5   C10  118.11  3.000
 22N  H6   N5   C5   117.44  3.000
 22N  C10  N5   C5   124.46  3.000
 22N  C11  C10  O10  121.18  3.000
 22N  C11  C10  N5   115.10  3.000
 22N  O10  C10  N5   123.72  3.000
 22N  H9   C11  H8   107.29  3.000
 22N  H9   C11  H7   108.34  3.000
 22N  H8   C11  H7   108.44  3.000
 22N  H9   C11  C10  109.32  3.000
 22N  H8   C11  C10  109.46  3.000
 22N  H7   C11  C10  113.79  3.000
 22N  H10  C6   O7   109.95  3.000
 22N  H10  C6   C7   108.47  3.000
 22N  O7   C6   C7   111.85  3.000
 22N  H10  C6   C5   106.88  3.000
 22N  C7   C6   C5   110.65  3.000
 22N  O7   C6   C5   108.92  3.000
 22N  H11  C7   C6   117.23  3.000
 22N  H11  C7   C2   118.68  3.000
 22N  C6   C7   C2   124.09  3.000
 22N  C8   O7   C6   116.35  3.000
 22N  H12  C8   C81  108.56  3.000
 22N  H12  C8   C9   108.23  3.000
 22N  C81  C8   C9   110.53  3.000
 22N  H12  C8   O7   109.84  3.000
 22N  C9   C8   O7   108.66  3.000
 22N  C81  C8   O7   110.98  3.000
 22N  H14  C9   H13  106.12  3.000
 22N  H14  C9   C91  109.41  3.000
 22N  H13  C9   C91  109.95  3.000
 22N  H14  C9   C8   107.62  3.000
 22N  H13  C9   C8   109.00  3.000
 22N  C91  C9   C8   114.40  3.000
 22N  H16  C81  H15  106.18  3.000
 22N  H16  C81  C82  109.59  3.000
 22N  H15  C81  C82  109.04  3.000
 22N  H16  C81  C8   108.69  3.000
 22N  H15  C81  C8   107.45  3.000
 22N  C82  C81  C8   115.48  3.000
 22N  H19  C82  H18  107.44  3.000
 22N  H19  C82  H17  106.96  3.000
 22N  H18  C82  H17  107.92  3.000
 22N  H19  C82  C81  110.47  3.000
 22N  H18  C82  C81  111.77  3.000
 22N  H17  C82  C81  112.05  3.000
 22N  H22  C91  H21  107.73  3.000
 22N  H22  C91  H20  107.45  3.000
 22N  H21  C91  H20  107.74  3.000
 22N  H22  C91  C9   110.80  3.000
 22N  H21  C91  C9   111.70  3.000
 22N  H20  C91  C9   111.23  3.000
 22N  H24  N4   H23  105.52  3.000
 22N  H24  N4   C4   109.54  3.000
 22N  H23  N4   C4   109.06  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
 22N  CONST_01  O10  C10  N5   C5     0.00   0.0  0
 22N  CONST_02  C11  C10  N5   C5   180.00   0.0  0
 22N  CONST_03  H6   N5   C10  O10  180.00   0.0  0
 22N  Var_01    C6   C7   C2   C3     0.41  30.0  1
 22N  Var_02    C7   C2   C3   C4   -11.44  30.0  1
 22N  Var_03    C7   C2   C1   O1A    3.84  30.0  2
 22N  Var_04    C81  C8   O7   C6   -99.37  30.0  1
 22N  Var_05    C82  C81  C8   O7    60.26  30.0  2
 22N  Var_06    C91  C9   C8   O7   -62.92  30.0  1
 22N  Var_07    H7   C11  C10  N5     4.56  30.0  3
 22N  Var_08    H17  C82  C81  C8   -65.31  30.0  3
 22N  Var_09    H20  C91  C9   C8   -58.08  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
 22N  chir_01  C4  C5  C3  N4  positiv
 22N  chir_02  C5  N5  C6  C4  positiv
 22N  chir_03  C6  O7  C7  C5  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
 22N  plan-1  C5   0.020
 22N  plan-1  N5   0.020
 22N  plan-1  C10  0.020
 22N  plan-1  O10  0.020
 22N  plan-1  C11  0.020
 22N  plan-1  H6   0.020
 22N  plan-2  C1   0.020
 22N  plan-2  O1A  0.020
 22N  plan-2  O1B  0.020
 22N  plan-2  C2   0.020

