# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue May  5 18:08:18 2020
#   Inital geometry file: a 112 line input string
#   Ligand name: 4-({(1R)-1-[(R)-hydroxy(phenoxy)phosphoryl]pentyl}amino)-4-oxobutanoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCC[C@H](NC(=O)CCC(O)=O)[P@](O)(=O)Oc1ccccc1
#
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
 HEP  HEP  '4-({(1R)-1-[(R)-hydroxy(phenoxy)phosphoryl]pentyl}amino)-4-oxobutanoic acid'  ligand  43  23  .  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_HEP
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
 HEP  C1    C  CH1    0  -0.335   0.9713  -0.1224  -0.1733
 HEP  C2    C  CH2    0  -0.420   2.3152   0.3258   0.3974
 HEP  C3    C  CH2    0  -0.424   2.5830  -0.0809   1.8413
 HEP  C4    C  CH2    0  -0.418   4.0149   0.2219   2.2656
 HEP  C5    C  CH3    0  -0.662   4.2952  -0.1608   3.7125
 HEP  C6    C  CR16   0  -0.338  -2.7911  -0.4157   2.8957
 HEP  C7    C  CR16   0  -0.250  -3.5743  -0.2060   4.0227
 HEP  C8    C  CR16   0  -0.275  -2.9872   0.0955   5.2451
 HEP  C9    C  CR16   0  -0.249  -1.6036   0.1834   5.3325
 HEP  C10   C  CR16   0  -0.337  -0.8129  -0.0200   4.2101
 HEP  C11   C  CR6    0   0.375  -1.4037  -0.3277   2.9882
 HEP  C12   C  C      0   0.571   0.2865  -0.4762  -2.5202
 HEP  C13   C  CH2    0  -0.580   0.1987  -0.7127  -5.0431
 HEP  C14   C  CH2    0  -0.580   0.1319   0.2266  -3.8517
 HEP  C15   C  C      0   0.417  -0.0174  -0.0372  -6.4093
 HEP  O1P   O  O      0  -0.784  -0.1978   1.9074   1.3132
 HEP  O2P   O  OP    -1  -0.767  -1.7238   0.4351  -0.1932
 HEP  O3P   O  O2     0  -0.651  -0.6182  -0.5752   1.9092
 HEP  O4    O  O      0  -0.512  -0.1125  -1.6171  -2.3260
 HEP  O5    O  O      0  -0.609  -0.4148   1.1445  -6.4194
 HEP  O6    O  OC    -1  -0.630   0.2121  -0.7485  -7.4098
 HEP  N1    N  NH1    0  -0.641   0.8993   0.2544  -1.5705
 HEP  P     P  P      0   1.274  -0.5142   0.5803   0.6847
 HEP  H1    H  HCH1   0   0.258   0.9043  -1.2116  -0.1273
 HEP  H21   H  HCH2   0   0.218   2.3999   1.4138   0.3094
 HEP  H22   H  HCH2   0   0.224   3.0982  -0.0975  -0.2402
 HEP  H31   H  HCH2   0   0.205   2.3847  -1.1503   1.9681
 HEP  H32   H  HCH2   0   0.226   1.8939   0.4427   2.5066
 HEP  H41   H  HCH2   0   0.211   4.2178   1.2880   2.1226
 HEP  H42   H  HCH2   0   0.210   4.7092  -0.3095   1.6076
 HEP  H51   H  HCH3   0   0.226   5.3287   0.0505   3.9897
 HEP  H52   H  HCH3   0   0.216   3.6504   0.3890   4.4007
 HEP  H53   H  HCH3   0   0.216   4.1203  -1.2254   3.8787
 HEP  H8    H  HCR6   0   0.252  -3.6020   0.2567   6.1209
 HEP  H9    H  HCR6   0   0.254  -1.1344   0.4199   6.2791
 HEP  H10   H  HCR6   0   0.255   0.2655   0.0468   4.2803
 HEP  H131  H  HCH2   0   0.224   1.1609  -1.2340  -5.0585
 HEP  H132  H  HCH2   0   0.232  -0.5533  -1.5001  -4.9355
 HEP  H141  H  HCH2   0   0.258  -0.8367   0.7362  -3.8343
 HEP  H142  H  HCH2   0   0.238   0.8791   1.0176  -3.9469
 HEP  HN1   H  HNH1   0   0.391   1.1568   1.2016  -1.7999
 HEP  H6    H  HCR6   0   0.260  -3.2506  -0.6599   1.9469
 HEP  H7    H  HCR6   0   0.254  -4.6515  -0.2784   3.9423

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
 HEP  C1   C2    single    1.527  0.020  1.527
 HEP  C1   N1    single    1.449  0.020  1.449
 HEP  C1   P     single    1.854  0.020  1.854
 HEP  C1   H1    single    0.970  0.020  1.090
 HEP  C2   C3    single    1.524  0.020  1.524
 HEP  C2   H21   single    0.970  0.020  1.090
 HEP  C2   H22   single    0.970  0.020  1.090
 HEP  C3   C4    single    1.524  0.020  1.524
 HEP  C3   H31   single    0.970  0.020  1.090
 HEP  C3   H32   single    0.970  0.020  1.090
 HEP  C4   C5    single    1.523  0.020  1.523
 HEP  C4   H41   single    0.970  0.020  1.090
 HEP  C4   H42   single    0.970  0.020  1.090
 HEP  C5   H51   single    0.970  0.020  1.090
 HEP  C5   H52   single    0.970  0.020  1.090
 HEP  C5   H53   single    0.970  0.020  1.090
 HEP  C6   C7    aromatic  1.388  0.020  1.388
 HEP  C6   C11   aromatic  1.393  0.020  1.393
 HEP  C6   H6    single    0.930  0.020  1.080
 HEP  C7   C8    aromatic  1.389  0.020  1.389
 HEP  C7   H7    single    0.930  0.020  1.080
 HEP  C8   C9    aromatic  1.389  0.020  1.389
 HEP  C8   H8    single    0.930  0.020  1.080
 HEP  C9   C10   aromatic  1.388  0.020  1.388
 HEP  C9   H9    single    0.930  0.020  1.080
 HEP  C10  C11   aromatic  1.392  0.020  1.392
 HEP  C10  H10   single    0.930  0.020  1.080
 HEP  C11  O3P   single    1.357  0.020  1.357
 HEP  C12  C14   single    1.514  0.020  1.514
 HEP  C12  O4    double    1.224  0.020  1.224
 HEP  C12  N1    single    1.346  0.020  1.346
 HEP  C13  C14   single    1.519  0.020  1.519
 HEP  C13  C15   single    1.539  0.020  1.539
 HEP  C13  H131  single    0.970  0.020  1.090
 HEP  C13  H132  single    0.970  0.020  1.090
 HEP  C14  H141  single    0.970  0.020  1.090
 HEP  C14  H142  single    0.970  0.020  1.090
 HEP  C15  O5    deloc     1.247  0.020  1.247
 HEP  C15  O6    deloc     1.249  0.020  1.249
 HEP  O1P  P     deloc     1.502  0.020  1.502
 HEP  O2P  P     deloc     1.502  0.020  1.502
 HEP  O3P  P     single    1.687  0.020  1.687
 HEP  N1   HN1   single    0.860  0.020  1.020

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
 HEP  H1    C1   P     108.02  3.000
 HEP  H1    C1   N1    107.27  3.000
 HEP  P     C1   N1    107.94  3.000
 HEP  H1    C1   C2    109.32  3.000
 HEP  P     C1   C2    114.89  3.000
 HEP  N1    C1   C2    109.13  3.000
 HEP  H22   C2   H21   106.38  3.000
 HEP  H22   C2   C3    108.84  3.000
 HEP  H21   C2   C3    109.13  3.000
 HEP  H22   C2   C1    107.35  3.000
 HEP  H21   C2   C1    109.25  3.000
 HEP  C3    C2   C1    115.50  3.000
 HEP  H32   C3   H31   106.47  3.000
 HEP  H32   C3   C4    109.15  3.000
 HEP  H31   C3   C4    109.39  3.000
 HEP  H32   C3   C2    109.79  3.000
 HEP  H31   C3   C2    109.79  3.000
 HEP  C4    C3   C2    112.09  3.000
 HEP  H42   C4   H41   106.07  3.000
 HEP  H42   C4   C5    109.42  3.000
 HEP  H41   C4   C5    109.56  3.000
 HEP  H42   C4   C3    109.41  3.000
 HEP  H41   C4   C3    109.35  3.000
 HEP  C5    C4   C3    112.81  3.000
 HEP  H53   C5   H52   107.49  3.000
 HEP  H53   C5   H51   107.58  3.000
 HEP  H52   C5   H51   107.57  3.000
 HEP  H53   C5   C4    111.12  3.000
 HEP  H52   C5   C4    111.33  3.000
 HEP  H51   C5   C4    111.55  3.000
 HEP  H6    C6   C11   119.69  3.000
 HEP  H6    C6   C7    120.42  3.000
 HEP  C11   C6   C7    119.89  3.000
 HEP  H7    C7   C8    120.02  3.000
 HEP  H7    C7   C6    119.40  3.000
 HEP  C8    C7   C6    120.58  3.000
 HEP  H8    C8   C9    120.36  3.000
 HEP  H8    C8   C7    120.30  3.000
 HEP  C9    C8   C7    119.34  3.000
 HEP  H9    C9   C10   119.49  3.000
 HEP  H9    C9   C8    120.03  3.000
 HEP  C10   C9   C8    120.48  3.000
 HEP  H10   C10  C11   119.56  3.000
 HEP  H10   C10  C9    120.39  3.000
 HEP  C11   C10  C9    120.04  3.000
 HEP  O3P   C11  C10   119.51  3.000
 HEP  O3P   C11  C6    120.80  3.000
 HEP  C10   C11  C6    119.67  3.000
 HEP  N1    C12  O4    122.85  3.000
 HEP  N1    C12  C14   114.53  3.000
 HEP  O4    C12  C14   122.61  3.000
 HEP  H132  C13  H131  105.23  3.000
 HEP  H132  C13  C15   107.86  3.000
 HEP  H131  C13  C15   108.66  3.000
 HEP  H132  C13  C14   109.74  3.000
 HEP  H131  C13  C14   110.14  3.000
 HEP  C15   C13  C14   114.76  3.000
 HEP  H142  C14  H141  105.63  3.000
 HEP  H142  C14  C13   110.46  3.000
 HEP  H141  C14  C13   109.84  3.000
 HEP  H142  C14  C12   110.06  3.000
 HEP  H141  C14  C12   107.01  3.000
 HEP  C13   C14  C12   113.49  3.000
 HEP  O6    C15  O5    126.30  3.000
 HEP  O6    C15  C13   115.80  3.000
 HEP  O5    C15  C13   117.89  3.000
 HEP  P     O3P  C11   119.20  3.000
 HEP  HN1   N1   C12   117.77  3.000
 HEP  HN1   N1   C1    116.81  3.000
 HEP  C12   N1   C1    124.19  3.000
 HEP  O3P   P    O2P   107.97  3.000
 HEP  O3P   P    O1P   108.33  3.000
 HEP  O2P   P    O1P   119.98  3.000
 HEP  O3P   P    C1     97.23  3.000
 HEP  O2P   P    C1    109.77  3.000
 HEP  O1P   P    C1    111.09  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
 HEP  CONST_01  C9   C8   C7   C6     0.00   0.0  0
 HEP  CONST_02  C9   C10  C11  C6     0.00   0.0  0
 HEP  CONST_03  C10  C11  C6   C7     0.00   0.0  0
 HEP  CONST_04  C10  C9   C8   C7     0.00   0.0  0
 HEP  CONST_05  C11  C6   C7   C8     0.00   0.0  0
 HEP  CONST_06  C11  C10  C9   C8     0.00   0.0  0
 HEP  CONST_07  O3P  C11  C6   C7   180.00   0.0  0
 HEP  CONST_08  O3P  C11  C10  C9   180.00   0.0  0
 HEP  CONST_09  H8   C8   C7   C6   180.00   0.0  0
 HEP  CONST_10  H10  C10  C11  C6   180.00   0.0  0
 HEP  CONST_11  H9   C9   C8   C7   180.00   0.0  0
 HEP  CONST_12  H6   C6   C7   C8   180.00   0.0  0
 HEP  CONST_13  H7   C7   C8   C9   180.00   0.0  0
 HEP  CONST_14  C14  C12  N1   C1   180.00   0.0  0
 HEP  CONST_15  O4   C12  N1   C1     0.00   0.0  0
 HEP  CONST_16  HN1  N1   C12  C14    0.00   0.0  0
 HEP  Var_01    O1P  P    O3P  C11   50.67  30.0  3
 HEP  Var_02    C4   C3   C2   C1   171.57  30.0  3
 HEP  Var_03    C5   C4   C3   C2   179.22  30.0  3
 HEP  Var_04    C15  C13  C14  C12  177.42  30.0  1
 HEP  Var_05    O4   C12  C14  C13  -32.37  30.0  2
 HEP  Var_06    O5   C15  C13  C14  -10.24  30.0  3
 HEP  Var_07    H51  C5   C4   C3   179.14  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
 HEP  chir_01  C1  C2  N1  P  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
 HEP  plan-1  C6   0.020
 HEP  plan-1  C7   0.020
 HEP  plan-1  C8   0.020
 HEP  plan-1  C9   0.020
 HEP  plan-1  C10  0.020
 HEP  plan-1  C11  0.020
 HEP  plan-1  O3P  0.020
 HEP  plan-1  H8   0.020
 HEP  plan-1  H9   0.020
 HEP  plan-1  H10  0.020
 HEP  plan-1  H6   0.020
 HEP  plan-1  H7   0.020
 HEP  plan-2  C1   0.020
 HEP  plan-2  C12  0.020
 HEP  plan-2  C14  0.020
 HEP  plan-2  O4   0.020
 HEP  plan-2  N1   0.020
 HEP  plan-2  HN1  0.020
 HEP  plan-3  C13  0.020
 HEP  plan-3  C15  0.020
 HEP  plan-3  O5   0.020
 HEP  plan-3  O6   0.020

