# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue May 12 21:14:58 2020
#   Inital geometry file: a 144 line input string
#   Ligand name: (4R)-1-(1-benzofuran-3-ylcarbonyl)-N-ethyl-4-{[(3-ethyl-1-methyl-1H-pyrazol-5-yl)carbonyl]amino}-L-prolinamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCNC(=O)[C@@H]1C[C@H](CN1C(=O)c2coc3ccccc23)NC(=O)c4cc(CC)nn4C
#
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
 KV1  KV1  (4R)-1-(1-benzofuran-3-ylcarbonyl)-N-ethyl-4-{[(3-ethyl-1-methyl-1H-pyrazol-5-yl)carbonyl]amino}-L-prolinamide  ligand  59  32  .  2022-07-25  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_KV1
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
 KV1  C1    C  CH3   0  -0.701  -3.3627   6.1487  -0.2131
 KV1  N1    N  NH1   0  -0.633  -2.3547   3.9550   0.1345
 KV1  O1    O  O     0  -0.496  -1.8164   2.3193  -1.3202
 KV1  C2    C  CH2   0  -0.261  -2.9989   4.8161  -0.8388
 KV1  N2    N  NT    0  -0.481  -1.3230   0.6018   0.8418
 KV1  O2    O  O     0  -0.487  -3.5404   0.8518   1.0170
 KV1  C3    C  C     0   0.585  -1.8278   2.7695  -0.1837
 KV1  N3    N  NH1   0  -0.667   2.2256   0.7487   0.1849
 KV1  O3    O  O     0  -0.427  -2.5857  -3.5698   0.8865
 KV1  C4    C  CH1   0  -0.223  -1.1433   2.0382   0.9696
 KV1  N4    N  N     0  -0.289   6.5117  -0.5617  -0.6981
 KV1  C5    C  CH2   0  -0.498   0.3762   2.2133   0.8953
 KV1  N5    N  NR5   0  -0.321   5.3595  -0.2939  -1.2924
 KV1  C6    C  CH1   0  -0.084   0.8265   1.0431   0.0292
 KV1  C7    C  CH2   0  -0.273  -0.0973  -0.0914   0.4840
 KV1  C9    C  CR5   0  -0.165  -2.7871  -1.3423   0.7340
 KV1  C10   C  CR15  0   0.029  -1.9924  -2.3800   1.0930
 KV1  C11   C  CR56  0   0.355  -3.8130  -3.3183   0.3678
 KV1  C12   C  CR16  0  -0.332  -4.7476  -4.2674  -0.0066
 KV1  C13   C  CR16  0  -0.269  -5.9403  -3.7815  -0.5160
 KV1  C14   C  CR16  0  -0.256  -6.1712  -2.4058  -0.6401
 KV1  C15   C  CR16  0  -0.358  -5.2214  -1.4749  -0.2577
 KV1  C16   C  CR56  0   0.079  -4.0118  -1.9435   0.2578
 KV1  C17   C  C     0   0.517   2.9687   0.1830  -0.7836
 KV1  C18   C  CR5   0   0.330   4.3668  -0.0963  -0.3965
 KV1  C19   C  CR15  0  -0.557   4.9343  -0.2562   0.8539
 KV1  C20   C  CR5   0   0.282   6.2798  -0.5505   0.6072
 KV1  C21   C  CH2   0  -0.501   7.3646  -0.8337   1.5959
 KV1  C22   C  CH3   0  -0.660   8.0002  -2.2085   1.4088
 KV1  H1    H  HCH3  0   0.246  -3.8399   6.7876  -0.9545
 KV1  H1A   H  HCH3  0   0.235  -4.0609   6.0225   0.6154
 KV1  H1B   H  HCH3  0   0.235  -2.4792   6.6688   0.1591
 KV1  HN1   H  HNH1  0   0.402  -2.4045   4.2190   1.1054
 KV1  H2    H  HCH2  0   0.234  -3.8961   4.3305  -1.2317
 KV1  H2A   H  HCH2  0   0.237  -2.3257   4.9699  -1.6838
 KV1  HN3   H  HNH1  0   0.411   2.6522   0.9620   1.0729
 KV1  H4    H  HCH1  0   0.292  -1.5288   2.3943   1.9278
 KV1  H5    H  HCH2  0   0.283   0.6724   3.1827   0.4963
 KV1  H5A   H  HCH2  0   0.271   0.7966   2.1227   1.9002
 KV1  H6    H  HCH1  0   0.281   0.6338   1.2634  -1.0199
 KV1  H7    H  HCH2  0   0.250   0.3434  -0.6005   1.3463
 KV1  H7A   H  HCH2  0   0.273  -0.2639  -0.8274  -0.3023
 KV1  H10   H  HCR5  0   0.309  -1.0075  -2.4208   1.5305
 KV1  H12   H  HCR6  0   0.276  -4.5575  -5.3278   0.0918
 KV1  H13   H  HCR6  0   0.264  -6.7076  -4.4795  -0.8238
 KV1  H14   H  HCR6  0   0.260  -7.1157  -2.0652  -1.0433
 KV1  H15   H  HCR6  0   0.256  -5.4157  -0.4166  -0.3537
 KV1  H19   H  HCR5  0   0.274   4.4494  -0.1980   1.8154
 KV1  H21   H  HCH2  0   0.245   8.1366  -0.0633   1.5216
 KV1  H21A  H  HCH2  0   0.243   6.9485  -0.7514   2.6014
 KV1  H22   H  HCH3  0   0.225   7.2603  -3.0024   1.5151
 KV1  H22A  H  HCH3  0   0.226   8.4515  -2.3019   0.4211
 KV1  H22B  H  HCH3  0   0.231   8.7813  -2.3771   2.1502
 KV1  H23   H  HCH3  0   0.257   4.7835  -1.0847  -3.1531
 KV1  H23A  H  HCH3  0   0.257   4.8380   0.6837  -3.0743
 KV1  H23B  H  HCH3  0   0.262   6.3436  -0.2459  -3.0900
 KV1  C8    C  C     0   0.521  -2.5753   0.1090   0.8712
 KV1  C23   C  CH3   0  -0.511   5.3167  -0.2321  -2.7395
 KV1  O4    O  O     0  -0.478   2.5336  -0.0874  -1.8938

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
 KV1  C1   C2    single    1.516  0.020  1.516
 KV1  N1   C2    single    1.450  0.020  1.450
 KV1  N1   C3    single    1.336  0.020  1.336
 KV1  O1   C3    double    1.223  0.020  1.223
 KV1  N2   C4    single    1.453  0.020  1.453
 KV1  N2   C7    single    1.453  0.020  1.453
 KV1  N2   C8    single    1.346  0.020  1.346
 KV1  O2   C8    double    1.227  0.020  1.227
 KV1  C3   C4    single    1.528  0.020  1.528
 KV1  N3   C6    single    1.438  0.020  1.438
 KV1  N3   C17   single    1.345  0.020  1.345
 KV1  O3   C10   aromatic  1.345  0.020  1.345
 KV1  O3   C11   aromatic  1.356  0.020  1.356
 KV1  C4   C5    single    1.531  0.020  1.531
 KV1  N4   N5    aromatic  1.324  0.020  1.324
 KV1  N4   C20   aromatic  1.326  0.020  1.326
 KV1  O4   C17   double    1.223  0.020  1.223
 KV1  C5   C6    single    1.524  0.020  1.524
 KV1  N5   C18   aromatic  1.352  0.020  1.352
 KV1  N5   C23   single    1.449  0.020  1.449
 KV1  C6   C7    single    1.532  0.020  1.532
 KV1  C8   C9    single    1.473  0.020  1.473
 KV1  C9   C10   aromatic  1.355  0.020  1.355
 KV1  C9   C16   aromatic  1.445  0.020  1.445
 KV1  C11  C12   aromatic  1.384  0.020  1.384
 KV1  C11  C16   aromatic  1.393  0.020  1.393
 KV1  C12  C13   aromatic  1.385  0.020  1.385
 KV1  C13  C14   aromatic  1.400  0.020  1.400
 KV1  C14  C15   aromatic  1.384  0.020  1.384
 KV1  C15  C16   aromatic  1.396  0.020  1.396
 KV1  C17  C18   single    1.477  0.020  1.477
 KV1  C18  C19   aromatic  1.382  0.020  1.382
 KV1  C19  C20   aromatic  1.399  0.020  1.399
 KV1  C20  C21   single    1.495  0.020  1.495
 KV1  C21  C22   single    1.526  0.020  1.526
 KV1  C1   H1    single    0.970  0.020  1.090
 KV1  C1   H1A   single    0.970  0.020  1.090
 KV1  C1   H1B   single    0.970  0.020  1.090
 KV1  N1   HN1   single    0.860  0.020  1.020
 KV1  C2   H2    single    0.970  0.020  1.090
 KV1  C2   H2A   single    0.970  0.020  1.090
 KV1  N3   HN3   single    0.860  0.020  1.020
 KV1  C4   H4    single    0.970  0.020  1.090
 KV1  C5   H5    single    0.970  0.020  1.090
 KV1  C5   H5A   single    0.970  0.020  1.090
 KV1  C6   H6    single    0.970  0.020  1.090
 KV1  C7   H7    single    0.970  0.020  1.090
 KV1  C7   H7A   single    0.970  0.020  1.090
 KV1  C10  H10   single    0.930  0.020  1.080
 KV1  C12  H12   single    0.930  0.020  1.080
 KV1  C13  H13   single    0.930  0.020  1.080
 KV1  C14  H14   single    0.930  0.020  1.080
 KV1  C15  H15   single    0.930  0.020  1.080
 KV1  C19  H19   single    0.930  0.020  1.080
 KV1  C21  H21   single    0.970  0.020  1.090
 KV1  C21  H21A  single    0.970  0.020  1.090
 KV1  C22  H22   single    0.970  0.020  1.090
 KV1  C22  H22A  single    0.970  0.020  1.090
 KV1  C22  H22B  single    0.970  0.020  1.090
 KV1  C23  H23   single    0.970  0.020  1.090
 KV1  C23  H23A  single    0.970  0.020  1.090
 KV1  C23  H23B  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
 KV1  H1B   C1   H1A   108.33  3.000
 KV1  H1B   C1   H1    107.92  3.000
 KV1  H1A   C1   H1    107.73  3.000
 KV1  H1B   C1   C2    111.44  3.000
 KV1  H1A   C1   C2    111.43  3.000
 KV1  H1    C1   C2    109.86  3.000
 KV1  HN1   N1   C3    118.79  3.000
 KV1  HN1   N1   C2    117.98  3.000
 KV1  C3    N1   C2    122.84  3.000
 KV1  H2A   C2   H2    106.89  3.000
 KV1  H2A   C2   N1    109.23  3.000
 KV1  H2    C2   N1    109.99  3.000
 KV1  H2A   C2   C1    110.10  3.000
 KV1  H2    C2   C1    109.99  3.000
 KV1  N1    C2   C1    110.57  3.000
 KV1  C8    N2   C7    127.99  3.000
 KV1  C8    N2   C4    118.36  3.000
 KV1  C7    N2   C4    112.89  3.000
 KV1  C4    C3   O1    121.43  3.000
 KV1  C4    C3   N1    114.95  3.000
 KV1  O1    C3   N1    123.50  3.000
 KV1  HN3   N3   C17   119.30  3.000
 KV1  HN3   N3   C6    117.63  3.000
 KV1  C17   N3   C6    123.06  3.000
 KV1  C11   O3   C10   107.09  3.000
 KV1  H4    C4   C5    110.82  3.000
 KV1  H4    C4   C3    110.36  3.000
 KV1  C5    C4   C3    110.69  3.000
 KV1  H4    C4   N2    110.84  3.000
 KV1  C5    C4   N2    103.39  3.000
 KV1  C3    C4   N2    110.57  3.000
 KV1  C20   N4   N5    106.74  3.000
 KV1  H5A   C5   H5    107.82  3.000
 KV1  H5A   C5   C6    110.19  3.000
 KV1  H5    C5   C6    113.26  3.000
 KV1  H5A   C5   C4    109.12  3.000
 KV1  H5    C5   C4    112.92  3.000
 KV1  C6    C5   C4    103.47  3.000
 KV1  C23   N5   C18   129.34  3.000
 KV1  C23   N5   N4    118.86  3.000
 KV1  C18   N5   N4    111.79  3.000
 KV1  H6    C6   C7    109.21  3.000
 KV1  H6    C6   C5    109.86  3.000
 KV1  C7    C6   C5    102.81  3.000
 KV1  H6    C6   N3    108.52  3.000
 KV1  C7    C6   N3    113.76  3.000
 KV1  C5    C6   N3    112.53  3.000
 KV1  H7A   C7   H7    108.42  3.000
 KV1  H7A   C7   C6    112.21  3.000
 KV1  H7    C7   C6    109.61  3.000
 KV1  H7A   C7   N2    111.77  3.000
 KV1  H7    C7   N2    111.58  3.000
 KV1  C6    C7   N2    103.21  3.000
 KV1  C16   C9   C10   105.40  3.000
 KV1  C16   C9   C8    124.23  3.000
 KV1  C10   C9   C8    130.19  3.000
 KV1  H10   C10  C9    132.21  3.000
 KV1  H10   C10  O3    115.57  3.000
 KV1  C9    C10  O3    112.20  3.000
 KV1  C16   C11  C12   123.99  3.000
 KV1  C16   C11  O3    110.02  3.000
 KV1  C12   C11  O3    125.99  3.000
 KV1  H12   C12  C13   121.92  3.000
 KV1  H12   C12  C11   121.94  3.000
 KV1  C13   C12  C11   116.14  3.000
 KV1  H13   C13  C14   119.45  3.000
 KV1  H13   C13  C12   119.28  3.000
 KV1  C14   C13  C12   121.28  3.000
 KV1  H14   C14  C15   119.37  3.000
 KV1  H14   C14  C13   119.09  3.000
 KV1  C15   C14  C13   121.54  3.000
 KV1  H15   C15  C16   121.17  3.000
 KV1  H15   C15  C14   120.73  3.000
 KV1  C16   C15  C14   118.10  3.000
 KV1  C15   C16  C11   118.95  3.000
 KV1  C15   C16  C9    135.76  3.000
 KV1  C11   C16  C9    105.28  3.000
 KV1  C18   C17  O4    122.19  3.000
 KV1  C18   C17  N3    114.43  3.000
 KV1  O4    C17  N3    123.37  3.000
 KV1  C19   C18  C17   130.34  3.000
 KV1  C19   C18  N5    106.33  3.000
 KV1  C17   C18  N5    123.30  3.000
 KV1  H19   C19  C20   126.94  3.000
 KV1  H19   C19  C18   127.99  3.000
 KV1  C20   C19  C18   105.05  3.000
 KV1  C21   C20  C19   128.39  3.000
 KV1  C21   C20  N4    121.51  3.000
 KV1  C19   C20  N4    110.09  3.000
 KV1  H21A  C21  H21   106.19  3.000
 KV1  H21A  C21  C22   109.86  3.000
 KV1  H21   C21  C22   109.41  3.000
 KV1  H21A  C21  C20   108.57  3.000
 KV1  H21   C21  C20   109.51  3.000
 KV1  C22   C21  C20   113.06  3.000
 KV1  H22B  C22  H22A  107.84  3.000
 KV1  H22B  C22  H22   107.89  3.000
 KV1  H22A  C22  H22   107.87  3.000
 KV1  H22B  C22  C21   110.75  3.000
 KV1  H22A  C22  C21   111.15  3.000
 KV1  H22   C22  C21   111.18  3.000
 KV1  C9    C8   O2    119.64  3.000
 KV1  C9    C8   N2    119.50  3.000
 KV1  O2    C8   N2    120.86  3.000
 KV1  H23B  C23  H23A  109.15  3.000
 KV1  H23B  C23  H23   109.34  3.000
 KV1  H23A  C23  H23   109.13  3.000
 KV1  H23B  C23  N5    107.10  3.000
 KV1  H23A  C23  N5    110.90  3.000
 KV1  H23   C23  N5    111.16  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
 KV1  CONST_01  C16  C9   C10  O3      0.00   0.0  0
 KV1  CONST_02  C13  C12  C11  O3    180.00   0.0  0
 KV1  CONST_03  C9   C16  C11  O3      0.00   0.0  0
 KV1  CONST_04  C15  C16  C11  O3    180.00   0.0  0
 KV1  CONST_05  C19  C18  N5   N4      0.00   0.0  0
 KV1  CONST_06  C18  C19  C20  N4      0.00   0.0  0
 KV1  CONST_07  C19  C20  N4   N5      0.00   0.0  0
 KV1  CONST_08  C20  C19  C18  N5      0.00   0.0  0
 KV1  CONST_09  C11  O3   C10  C9      0.00   0.0  0
 KV1  CONST_10  C12  C11  C16  C9    180.00   0.0  0
 KV1  CONST_11  C14  C15  C16  C9    180.00   0.0  0
 KV1  CONST_12  C12  C11  O3   C10   180.00   0.0  0
 KV1  CONST_13  C16  C11  O3   C10     0.00   0.0  0
 KV1  CONST_14  C11  C16  C9   C10     0.00   0.0  0
 KV1  CONST_15  C15  C16  C9   C10   180.00   0.0  0
 KV1  CONST_16  C14  C13  C12  C11     0.00   0.0  0
 KV1  CONST_17  C14  C15  C16  C11     0.00   0.0  0
 KV1  CONST_18  C15  C16  C11  C12     0.00   0.0  0
 KV1  CONST_19  C15  C14  C13  C12     0.00   0.0  0
 KV1  CONST_20  C16  C11  C12  C13     0.00   0.0  0
 KV1  CONST_21  C16  C15  C14  C13     0.00   0.0  0
 KV1  CONST_22  C20  N4   N5   C18     0.00   0.0  0
 KV1  CONST_23  C8   C9   C10  O3    180.00   0.0  0
 KV1  CONST_24  C17  C18  N5   N4    180.00   0.0  0
 KV1  CONST_25  C21  C20  N4   N5    180.00   0.0  0
 KV1  CONST_26  C11  C16  C9   C8    180.00   0.0  0
 KV1  CONST_27  C15  C16  C9   C8      0.00   0.0  0
 KV1  CONST_28  C20  C19  C18  C17   180.00   0.0  0
 KV1  CONST_29  C21  C20  C19  C18   180.00   0.0  0
 KV1  CONST_30  C23  N5   C18  C19   180.00   0.0  0
 KV1  CONST_31  C23  N5   N4   C20   180.00   0.0  0
 KV1  CONST_32  C9   C8   N2   C4    180.00   0.0  0
 KV1  CONST_33  C9   C8   N2   C7      0.00   0.0  0
 KV1  CONST_34  H12  C12  C11  O3      0.00   0.0  0
 KV1  CONST_35  H19  C19  C20  N4    180.00   0.0  0
 KV1  CONST_36  H15  C15  C16  C9      0.00   0.0  0
 KV1  CONST_37  H10  C10  O3   C11   180.00   0.0  0
 KV1  CONST_38  H13  C13  C12  C11   180.00   0.0  0
 KV1  CONST_39  H14  C14  C13  C12   180.00   0.0  0
 KV1  CONST_40  C4   N2   C8   O2      0.00   0.0  0
 KV1  CONST_41  C7   N2   C8   O2    180.00   0.0  0
 KV1  CONST_42  C18  C17  N3   C6    180.00   0.0  0
 KV1  CONST_43  C4   C3   N1   C2    180.00   0.0  0
 KV1  CONST_44  C6   N3   C17  O4      0.00   0.0  0
 KV1  CONST_45  HN1  N1   C3   C4      0.00   0.0  0
 KV1  CONST_46  HN3  N3   C17  C18     0.00   0.0  0
 KV1  CONST_47  C2   N1   C3   O1      0.00   0.0  0
 KV1  Var_01    C6   C7   N2   C4    -14.27  30.0  1
 KV1  Var_02    C10  C9   C8   N2     29.77  30.0  2
 KV1  Var_03    N5   C18  C17  N3   -160.45  30.0  2
 KV1  Var_04    C22  C21  C20  N4    -58.83  30.0  2
 KV1  Var_05    H23  C23  N5   N4    108.92  30.0  2
 KV1  Var_06    H22  C22  C21  C20   -59.80  30.0  3
 KV1  Var_07    C3   N1   C2   C1   -173.96  30.0  1
 KV1  Var_08    H1   C1   C2   N1    179.68  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
 KV1  chir_01  C4  N2  C3  C5  positiv
 KV1  chir_02  C6  N3  C7  C5  negativ

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
 KV1  plan-1  N4   0.020
 KV1  plan-1  N5   0.020
 KV1  plan-1  C17  0.020
 KV1  plan-1  C18  0.020
 KV1  plan-1  C19  0.020
 KV1  plan-1  C20  0.020
 KV1  plan-1  C21  0.020
 KV1  plan-1  H19  0.020
 KV1  plan-1  C23  0.020
 KV1  plan-2  O3   0.020
 KV1  plan-2  C9   0.020
 KV1  plan-2  C10  0.020
 KV1  plan-2  C11  0.020
 KV1  plan-2  C12  0.020
 KV1  plan-2  C13  0.020
 KV1  plan-2  C14  0.020
 KV1  plan-2  C15  0.020
 KV1  plan-2  C16  0.020
 KV1  plan-2  H10  0.020
 KV1  plan-2  H12  0.020
 KV1  plan-2  H13  0.020
 KV1  plan-2  H14  0.020
 KV1  plan-2  H15  0.020
 KV1  plan-2  C8   0.020
 KV1  plan-3  N3   0.020
 KV1  plan-3  C6   0.020
 KV1  plan-3  C17  0.020
 KV1  plan-3  C18  0.020
 KV1  plan-3  HN3  0.020
 KV1  plan-3  O4   0.020
 KV1  plan-4  N2   0.020
 KV1  plan-4  O2   0.020
 KV1  plan-4  C4   0.020
 KV1  plan-4  C7   0.020
 KV1  plan-4  C9   0.020
 KV1  plan-4  C8   0.020
 KV1  plan-5  N1   0.020
 KV1  plan-5  O1   0.020
 KV1  plan-5  C2   0.020
 KV1  plan-5  C3   0.020
 KV1  plan-5  C4   0.020
 KV1  plan-5  HN1  0.020

