# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue May  5 20:05:00 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  45  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  -0.354   1.1562  -0.1684  -0.1207
 HEP  C2    C  CH2   0  -0.469   2.4721   0.3437   0.4668
 HEP  C3    C  CH2   0  -0.429   2.7427  -0.0514   1.9140
 HEP  C4    C  CH2   0  -0.421   4.1719   0.2805   2.3265
 HEP  C5    C  CH3   0  -0.663   4.4672  -0.0942   3.7720
 HEP  C6    C  CR16  0  -0.314  -2.5764  -1.0805   2.8629
 HEP  C7    C  CR16  0  -0.251  -3.5114  -0.9449   3.8803
 HEP  C8    C  CR16  0  -0.260  -3.2335  -0.1583   4.9905
 HEP  C9    C  CR16  0  -0.250  -2.0097   0.4916   5.0852
 HEP  C10   C  CR16  0  -0.311  -1.0666   0.3639   4.0747
 HEP  C11   C  CR6   0   0.353  -1.3583  -0.4265   2.9728
 HEP  C12   C  C     0   0.609   0.3424  -0.4281  -2.4308
 HEP  C13   C  CH2   0  -0.582  -0.5989  -0.2905  -4.7522
 HEP  C14   C  CH2   0  -0.581   0.6162  -0.0720  -3.8693
 HEP  C15   C  C     0   0.558  -0.3245   0.0167  -6.1979
 HEP  O1P   O  O     0  -0.690  -0.2570   1.8953   1.2172
 HEP  O2P   O  OH1   0  -0.754  -1.5818   0.2026  -0.1552
 HEP  O3P   O  O2    0  -0.630  -0.4138  -0.5922   1.9818
 HEP  O4    O  O     0  -0.529  -0.5047  -1.2616  -2.1038
 HEP  O5    O  O     0  -0.442   0.7302   0.3972  -6.6409
 HEP  O6    O  OH1   0  -0.595  -1.4006  -0.1841  -6.9500
 HEP  N1    N  NH1   0  -0.640   1.0961   0.2049  -1.5223
 HEP  P     P  P     0   1.381  -0.3126   0.4865   0.7665
 HEP  H1    H  HCH1  0   0.311   1.1254  -1.2599  -0.0453
 HEP  H21   H  HCH2  0   0.251   2.5153   1.4322   0.3662
 HEP  H22   H  HCH2  0   0.261   3.2685  -0.0613  -0.1643
 HEP  H31   H  HCH2  0   0.224   2.5649  -1.1229   2.0456
 HEP  H32   H  HCH2  0   0.225   2.0531   0.4653   2.5863
 HEP  H41   H  HCH2  0   0.218   4.3531   1.3492   2.1786
 HEP  H42   H  HCH2  0   0.218   4.8684  -0.2420   1.6644
 HEP  H51   H  HCH3  0   0.229   5.4992   0.1351   4.0387
 HEP  H52   H  HCH3  0   0.218   3.8195   0.4473   4.4636
 HEP  H53   H  HCH3  0   0.218   4.3116  -1.1611   3.9419
 HEP  H7    H  HCR6  0   0.264  -4.4618  -1.4564   3.8010
 HEP  H8    H  HCR6  0   0.261  -3.9666  -0.0538   5.7791
 HEP  H9    H  HCR6  0   0.264  -1.7849   1.1054   5.9479
 HEP  H10   H  HCR6  0   0.269  -0.1098   0.8644   4.1474
 HEP  H131  H  HCH2  0   0.293  -0.9497  -1.3223  -4.6826
 HEP  H132  H  HCH2  0   0.292  -1.4370   0.3304  -4.4238
 HEP  H141  H  HCH2  0   0.280   0.9655   0.9598  -3.9361
 HEP  H142  H  HCH2  0   0.298   1.4493  -0.6971  -4.2043
 HEP  HOP2  H  HOH1  0   0.492  -1.4254  -0.5177  -0.8114
 HEP  HO6   H  HOH1  0   0.481  -1.2008   0.0199  -7.8758
 HEP  HN1   H  HNH1  0   0.423   1.7370   0.9172  -1.8386
 HEP  H6    H  HCR6  0   0.271  -2.7875  -1.6957   1.9979

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    1.529  0.020  1.529
 HEP  C1   N1    single    1.452  0.020  1.452
 HEP  C1   P     single    1.837  0.020  1.837
 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    1.522  0.020  1.522
 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  1.387  0.020  1.387
 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  1.387  0.020  1.387
 HEP  C10  H10   single    0.930  0.020  1.080
 HEP  C11  O3P   single    1.379  0.020  1.379
 HEP  C12  C14   single    1.507  0.020  1.507
 HEP  C12  O4    double    1.233  0.020  1.233
 HEP  C12  N1    single    1.339  0.020  1.339
 HEP  C13  C14   single    1.518  0.020  1.518
 HEP  C13  C15   single    1.503  0.020  1.503
 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    double    1.206  0.020  1.206
 HEP  C15  O6    single    1.328  0.020  1.328
 HEP  O1P  P     double    1.480  0.020  1.480
 HEP  O2P  P     single    1.594  0.020  1.594
 HEP  O2P  HOP2  single    0.850  0.020  0.980
 HEP  O3P  P     single    1.628  0.020  1.628
 HEP  O6   HO6   single    0.850  0.020  0.980
 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     107.45  3.000
 HEP  H1    C1   N1    108.77  3.000
 HEP  P     C1   N1    109.98  3.000
 HEP  H1    C1   C2    109.37  3.000
 HEP  P     C1   C2    112.53  3.000
 HEP  N1    C1   C2    108.69  3.000
 HEP  H22   C2   H21   106.65  3.000
 HEP  H22   C2   C3    108.81  3.000
 HEP  H21   C2   C3    109.77  3.000
 HEP  H22   C2   C1    106.31  3.000
 HEP  H21   C2   C1    109.38  3.000
 HEP  C3    C2   C1    115.51  3.000
 HEP  H32   C3   H31   106.65  3.000
 HEP  H32   C3   C4    108.80  3.000
 HEP  H31   C3   C4    109.46  3.000
 HEP  H32   C3   C2    110.45  3.000
 HEP  H31   C3   C2    109.83  3.000
 HEP  C4    C3   C2    111.53  3.000
 HEP  H42   C4   H41   106.23  3.000
 HEP  H42   C4   C5    109.49  3.000
 HEP  H41   C4   C5    109.68  3.000
 HEP  H42   C4   C3    109.22  3.000
 HEP  H41   C4   C3    109.36  3.000
 HEP  C5    C4   C3    112.66  3.000
 HEP  H53   C5   H52   107.56  3.000
 HEP  H53   C5   H51   107.60  3.000
 HEP  H52   C5   H51   107.60  3.000
 HEP  H53   C5   C4    111.15  3.000
 HEP  H52   C5   C4    111.38  3.000
 HEP  H51   C5   C4    111.36  3.000
 HEP  H6    C6   C11   120.18  3.000
 HEP  H6    C6   C7    120.65  3.000
 HEP  C11   C6   C7    119.17  3.000
 HEP  H7    C7   C8    120.14  3.000
 HEP  H7    C7   C6    119.44  3.000
 HEP  C8    C7   C6    120.42  3.000
 HEP  H8    C8   C9    120.15  3.000
 HEP  H8    C8   C7    120.12  3.000
 HEP  C9    C8   C7    119.73  3.000
 HEP  H9    C9   C10   119.43  3.000
 HEP  H9    C9   C8    120.17  3.000
 HEP  C10   C9   C8    120.40  3.000
 HEP  H10   C10  C11   120.19  3.000
 HEP  H10   C10  C9    120.61  3.000
 HEP  C11   C10  C9    119.20  3.000
 HEP  O3P   C11  C10   119.69  3.000
 HEP  O3P   C11  C6    119.21  3.000
 HEP  C10   C11  C6    121.09  3.000
 HEP  N1    C12  O4    121.75  3.000
 HEP  N1    C12  C14   115.70  3.000
 HEP  O4    C12  C14   122.54  3.000
 HEP  H132  C13  H131  105.73  3.000
 HEP  H132  C13  C15   108.22  3.000
 HEP  H131  C13  C15   108.24  3.000
 HEP  H132  C13  C14   110.93  3.000
 HEP  H131  C13  C14   110.87  3.000
 HEP  C15   C13  C14   112.58  3.000
 HEP  H142  C14  H141  106.12  3.000
 HEP  H142  C14  C13   110.44  3.000
 HEP  H141  C14  C13   110.90  3.000
 HEP  H142  C14  C12   107.19  3.000
 HEP  H141  C14  C12   109.87  3.000
 HEP  C13   C14  C12   112.08  3.000
 HEP  O6    C15  O5    123.26  3.000
 HEP  O6    C15  C13   111.46  3.000
 HEP  O5    C15  C13   125.28  3.000
 HEP  HOP2  O2P  P     112.85  3.000
 HEP  P     O3P  C11   119.96  3.000
 HEP  HO6   O6   C15   110.01  3.000
 HEP  HN1   N1   C12   118.58  3.000
 HEP  HN1   N1   C1    117.25  3.000
 HEP  C12   N1   C1    123.83  3.000
 HEP  O3P   P    O2P   105.31  3.000
 HEP  O3P   P    O1P   113.93  3.000
 HEP  O2P   P    O1P   112.05  3.000
 HEP  O3P   P    C1    100.02  3.000
 HEP  O2P   P    C1    107.09  3.000
 HEP  O1P   P    C1    117.16  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  CONST_17  HO6  O6   C15  C13   180.00   0.0  0
 HEP  Var_01    O1P  P    O3P  C11    49.90  30.0  3
 HEP  Var_02    C4   C3   C2   C1    169.57  30.0  3
 HEP  Var_03    C5   C4   C3   C2    179.57  30.0  3
 HEP  Var_04    C15  C13  C14  C12  -178.05  30.0  1
 HEP  Var_05    O4   C12  C14  C13    27.11  30.0  2
 HEP  Var_06    O5   C15  C13  C14    -0.06  30.0  3
 HEP  Var_07    H51  C5   C4   C3    178.95  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
 HEP  chir_02  P   O1P  O2P  O3P  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
 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  H7   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-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
 HEP  plan-3  HO6  0.020

