# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue May  5 16:12:36 2020
#   Inital geometry file: a 134 line input string
#   Ligand name: 4-{2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-[(3S)-piperidin-3-ylmethoxy]-1H-imidazo[4,5-c]pyridin-4-yl}-2-methylbut-3-yn-2-ol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCn1c(nc2c(ncc(OC[C@H]3CCCNC3)c12)C#CC(C)(C)O)c4nonc4N
#
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
 G93  G93  4-{2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-[(3S)-piperidin-3-ylmethoxy]-1H-imidazo[4,5-c]pyridin-4-yl}-2-methylbut-3-yn-2-ol  ligand  58  31  .  2021-08-10  2021-08-10  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_G93
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
 G93  C3    C  CSP   0   0.162  -2.8154  -2.2803   0.0031
 G93  N2    N  NR5   0  -0.545   0.2324   1.2439  -0.0228
 G93  N3    N  N     0  -0.503  -1.9075   0.5958  -0.0515
 G93  C2    C  CR6   0  -0.019  -1.4519  -1.8665   0.0366
 G93  N1    N  N     0  -0.406  -0.4978  -2.7770   0.0954
 G93  C1    C  CR56  0   0.100  -1.1134  -0.5045   0.0068
 G93  C17   C  CR5   0   0.351  -2.9634   3.3369  -0.3204
 G93  N5    N  N     0  -0.187  -3.0313   4.6342  -0.2363
 G93  O3    O  O     0  -0.213  -1.7666   5.0564   0.0313
 G93  N4    N  N     0  -0.119  -0.9153   4.0469   0.1218
 G93  C16   C  CR5   0   0.078  -1.5923   2.9638  -0.0901
 G93  C15   C  CR5   0   0.550  -1.0799   1.6106  -0.0588
 G93  C13   C  CH2   0  -0.341   1.4014   2.1203  -0.0485
 G93  C14   C  CH3   0  -0.664   1.8979   2.4639   1.3422
 G93  C4    C  CSP   0   0.049  -3.9757  -2.6044  -0.0236
 G93  C5    C  CT    0   0.006  -5.3941  -3.0043  -0.0523
 G93  C7    C  CH3   0  -0.671  -6.2714  -1.7525  -0.0835
 G93  C6    C  CH3   0  -0.655  -5.6485  -3.8737  -1.2808
 G93  O1    O  OH1   0  -0.654  -5.6892  -3.8043   1.0769
 G93  C12   C  CR56  0   0.309   0.2300  -0.1236   0.0369
 G93  C9    C  CR6   0   0.333   1.2365  -1.0946   0.1207
 G93  C8    C  CR16  0  -0.252   0.7887  -2.4108   0.1385
 G93  C10   C  CH2   0  -0.168   3.5427  -1.6770   0.2385
 G93  C11   C  CH1   0  -0.284   4.8740  -0.9669   0.3682
 G93  C18   C  CH2   0  -0.277   5.1622  -0.0469  -0.8163
 G93  N7    N  NH1   0  -0.596   6.4591   0.5809  -0.6499
 G93  C19   C  CH2   0  -0.292   7.5379  -0.3906  -0.6354
 G93  C20   C  CH2   0  -0.431   7.3599  -1.3313   0.5464
 G93  C21   C  CH2   0  -0.434   5.9925  -2.0043   0.4905
 G93  HN6   H  HNH2  0   0.405  -4.9230   2.8840  -0.5257
 G93  HN6A  H  HNH2  0   0.410  -3.8591   1.5464  -0.3992
 G93  H13   H  HCH2  0   0.288   2.1726   1.6239  -0.6304
 G93  H13A  H  HCH2  0   0.280   1.1269   3.0179  -0.5954
 G93  H14   H  HCH3  0   0.237   1.1247   2.9587   1.9291
 G93  H14A  H  HCH3  0   0.239   2.2264   1.5737   1.8775
 G93  H14B  H  HCH3  0   0.246   2.7472   3.1420   1.2652
 G93  H7    H  HCH3  0   0.238  -6.0600  -1.1444  -0.9627
 G93  H7A   H  HCH3  0   0.245  -7.3234  -2.0404  -0.1116
 G93  H7B   H  HCH3  0   0.241  -6.1066  -1.1316   0.7989
 G93  H6    H  HCH3  0   0.243  -5.0316  -4.7722  -1.2602
 G93  H6A   H  HCH3  0   0.243  -6.6974  -4.1715  -1.3158
 G93  H6B   H  HCH3  0   0.238  -5.4197  -3.3235  -2.1921
 G93  HO1   H  HOH1  0   0.452  -5.6232  -3.2574   1.8676
 G93  H8    H  HCR6  0   0.286   1.4981  -3.2268   0.1915
 G93  H10   H  HCH2  0   0.243   3.3893  -2.3432   1.0947
 G93  H10A  H  HCH2  0   0.230   3.5188  -2.2889  -0.6714
 G93  H11   H  HCH1  0   0.235   4.8601  -0.3606   1.2818
 G93  H18   H  HCH2  0   0.182   5.0957  -0.6438  -1.7439
 G93  H18A  H  HCH2  0   0.244   4.4082   0.7392  -0.8888
 G93  HN7   H  HNH1  0   0.352   6.6073   1.2444  -1.3985
 G93  H19   H  HCH2  0   0.185   7.5760  -0.9882  -1.5621
 G93  H19A  H  HCH2  0   0.231   8.4896   0.1396  -0.5600
 G93  H20   H  HCH2  0   0.231   8.1518  -2.0830   0.5470
 G93  H20A  H  HCH2  0   0.216   7.4521  -0.7630   1.4766
 G93  H21   H  HCH2  0   0.238   5.8377  -2.6306   1.3730
 G93  H21A  H  HCH2  0   0.215   5.9561  -2.6710  -0.3788
 G93  O2    O  O2    0  -0.467   2.5081  -0.6989   0.1886
 G93  N6    N  NH2   0  -0.850  -3.9891   2.5210  -0.6246

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
 G93  C3   C2    single    1.425  0.020  1.425
 G93  C3   C4    triple    1.205  0.020  1.205
 G93  N2   C15   aromatic  1.363  0.020  1.363
 G93  N2   C13   single    1.461  0.020  1.461
 G93  N2   C12   aromatic  1.369  0.020  1.369
 G93  N3   C1    aromatic  1.358  0.020  1.358
 G93  N3   C15   aromatic  1.310  0.020  1.310
 G93  C2   N1    aromatic  1.320  0.020  1.320
 G93  C2   C1    aromatic  1.404  0.020  1.404
 G93  O2   C9    single    1.333  0.020  1.333
 G93  O2   C10   single    1.425  0.020  1.425
 G93  N1   C8    aromatic  1.338  0.020  1.338
 G93  C1   C12   aromatic  1.397  0.020  1.397
 G93  N6   C17   single    1.345  0.020  1.345
 G93  C17  N5    aromatic  1.302  0.020  1.302
 G93  C17  C16   aromatic  1.439  0.020  1.439
 G93  N5   O3    aromatic  1.360  0.020  1.360
 G93  O3   N4    aromatic  1.324  0.020  1.324
 G93  N4   C16   aromatic  1.295  0.020  1.295
 G93  C16  C15   single    1.447  0.020  1.447
 G93  C13  C14   single    1.516  0.020  1.516
 G93  C4   C5    single    1.474  0.020  1.474
 G93  C5   C7    single    1.529  0.020  1.529
 G93  C5   C6    single    1.526  0.020  1.526
 G93  C5   O1    single    1.415  0.020  1.415
 G93  C12  C9    aromatic  1.401  0.020  1.401
 G93  C9   C8    aromatic  1.390  0.020  1.390
 G93  C10  C11   single    1.514  0.020  1.514
 G93  C11  C18   single    1.527  0.020  1.527
 G93  C11  C21   single    1.530  0.020  1.530
 G93  C18  N7    single    1.450  0.020  1.450
 G93  N7   C19   single    1.452  0.020  1.452
 G93  C19  C20   single    1.521  0.020  1.521
 G93  C20  C21   single    1.525  0.020  1.525
 G93  N6   HN6   single    0.890  0.020  1.040
 G93  N6   HN6A  single    0.890  0.020  1.040
 G93  C13  H13   single    0.970  0.020  1.090
 G93  C13  H13A  single    0.970  0.020  1.090
 G93  C14  H14   single    0.970  0.020  1.090
 G93  C14  H14A  single    0.970  0.020  1.090
 G93  C14  H14B  single    0.970  0.020  1.090
 G93  C7   H7    single    0.970  0.020  1.090
 G93  C7   H7A   single    0.970  0.020  1.090
 G93  C7   H7B   single    0.970  0.020  1.090
 G93  C6   H6    single    0.970  0.020  1.090
 G93  C6   H6A   single    0.970  0.020  1.090
 G93  C6   H6B   single    0.970  0.020  1.090
 G93  O1   HO1   single    0.850  0.020  0.980
 G93  C8   H8    single    0.930  0.020  1.080
 G93  C10  H10   single    0.970  0.020  1.090
 G93  C10  H10A  single    0.970  0.020  1.090
 G93  C11  H11   single    0.970  0.020  1.090
 G93  C18  H18   single    0.970  0.020  1.090
 G93  C18  H18A  single    0.970  0.020  1.090
 G93  N7   HN7   single    0.890  0.020  1.040
 G93  C19  H19   single    0.970  0.020  1.090
 G93  C19  H19A  single    0.970  0.020  1.090
 G93  C20  H20   single    0.970  0.020  1.090
 G93  C20  H20A  single    0.970  0.020  1.090
 G93  C21  H21   single    0.970  0.020  1.090
 G93  C21  H21A  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
 G93  C4    C3   C2    180.00  3.000
 G93  C12   N2   C13   126.97  3.000
 G93  C12   N2   C15   105.56  3.000
 G93  C13   N2   C15   127.47  3.000
 G93  C15   N3   C1    104.98  3.000
 G93  C1    C2   N1    119.72  3.000
 G93  C1    C2   C3    120.79  3.000
 G93  N1    C2   C3    119.48  3.000
 G93  C8    N1   C2    120.49  3.000
 G93  C12   C1   C2    119.74  3.000
 G93  C12   C1   N3    110.02  3.000
 G93  C2    C1   N3    130.23  3.000
 G93  C16   C17  N5    107.32  3.000
 G93  C16   C17  N6    127.24  3.000
 G93  N5    C17  N6    125.39  3.000
 G93  O3    N5   C17   105.88  3.000
 G93  N4    O3   N5    112.01  3.000
 G93  C16   N4   O3    106.89  3.000
 G93  C15   C16  N4    126.41  3.000
 G93  C15   C16  C17   125.66  3.000
 G93  N4    C16  C17   107.91  3.000
 G93  C16   C15  N3    120.06  3.000
 G93  C16   C15  N2    126.37  3.000
 G93  N3    C15  N2    113.57  3.000
 G93  H13A  C13  H13   106.70  3.000
 G93  H13A  C13  C14   110.94  3.000
 G93  H13   C13  C14   111.25  3.000
 G93  H13A  C13  N2    107.59  3.000
 G93  H13   C13  N2    107.66  3.000
 G93  C14   C13  N2    112.44  3.000
 G93  H14B  C14  H14A  107.96  3.000
 G93  H14B  C14  H14   107.98  3.000
 G93  H14A  C14  H14   108.69  3.000
 G93  H14B  C14  C13   109.35  3.000
 G93  H14A  C14  C13   111.36  3.000
 G93  H14   C14  C13   111.38  3.000
 G93  C5    C4   C3    180.00  3.000
 G93  O1    C5   C6    106.59  3.000
 G93  O1    C5   C7    111.07  3.000
 G93  C6    C5   C7    110.75  3.000
 G93  O1    C5   C4    109.79  3.000
 G93  C6    C5   C4    109.31  3.000
 G93  C7    C5   C4    109.29  3.000
 G93  H7B   C7   H7A   108.45  3.000
 G93  H7B   C7   H7    107.79  3.000
 G93  H7A   C7   H7    108.28  3.000
 G93  H7B   C7   C5    111.26  3.000
 G93  H7A   C7   C5    109.74  3.000
 G93  H7    C7   C5    111.23  3.000
 G93  H6B   C6   H6A   108.25  3.000
 G93  H6B   C6   H6    108.26  3.000
 G93  H6A   C6   H6    108.65  3.000
 G93  H6B   C6   C5    110.53  3.000
 G93  H6A   C6   C5    109.97  3.000
 G93  H6    C6   C5    111.10  3.000
 G93  HO1   O1   C5    108.64  3.000
 G93  C9    C12  C1    120.22  3.000
 G93  C9    C12  N2    133.92  3.000
 G93  C1    C12  N2    105.86  3.000
 G93  C8    C9   C12   115.18  3.000
 G93  C8    C9   O2    125.97  3.000
 G93  C12   C9   O2    118.85  3.000
 G93  H8    C8   C9    120.21  3.000
 G93  H8    C8   N1    115.16  3.000
 G93  C9    C8   N1    124.63  3.000
 G93  H10A  C10  H10   107.82  3.000
 G93  H10A  C10  C11   110.59  3.000
 G93  H10   C10  C11   109.95  3.000
 G93  H10A  C10  O2    109.77  3.000
 G93  H10   C10  O2    110.07  3.000
 G93  C11   C10  O2    108.64  3.000
 G93  H11   C11  C21   108.51  3.000
 G93  H11   C11  C18   108.39  3.000
 G93  C21   C11  C18   109.42  3.000
 G93  H11   C11  C10   108.63  3.000
 G93  C21   C11  C10   109.36  3.000
 G93  C18   C11  C10   112.45  3.000
 G93  H18A  C18  H18   106.96  3.000
 G93  H18A  C18  N7    108.27  3.000
 G93  H18   C18  N7    112.58  3.000
 G93  H18A  C18  C11   110.79  3.000
 G93  H18   C18  C11   108.32  3.000
 G93  N7    C18  C11   109.90  3.000
 G93  HN7   N7   C19   109.73  3.000
 G93  HN7   N7   C18   109.27  3.000
 G93  C19   N7   C18   112.08  3.000
 G93  H19A  C19  H19   106.91  3.000
 G93  H19A  C19  C20   110.41  3.000
 G93  H19   C19  C20   108.76  3.000
 G93  H19A  C19  N7    108.87  3.000
 G93  H19   C19  N7    112.31  3.000
 G93  C20   C19  N7    109.55  3.000
 G93  H20A  C20  H20   107.22  3.000
 G93  H20A  C20  C21   109.63  3.000
 G93  H20   C20  C21   110.28  3.000
 G93  H20A  C20  C19   109.24  3.000
 G93  H20   C20  C19   109.96  3.000
 G93  C21   C20  C19   110.45  3.000
 G93  H21A  C21  H21   106.68  3.000
 G93  H21A  C21  C20   109.10  3.000
 G93  H21   C21  C20   110.50  3.000
 G93  H21A  C21  C11   108.94  3.000
 G93  H21   C21  C11   110.46  3.000
 G93  C20   C21  C11   111.04  3.000
 G93  C10   O2   C9    119.38  3.000
 G93  HN6A  N6   HN6   116.48  3.000
 G93  HN6A  N6   C17   115.92  3.000
 G93  HN6   N6   C17   117.80  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
 G93  CONST_01  C1   N3   C15  N2      0.00   0.0  0
 G93  CONST_02  C17  C16  C15  N2    180.00   0.0  0
 G93  CONST_03  N4   C16  C15  N2      0.00   0.0  0
 G93  CONST_04  N3   C1   C12  N2      0.00   0.0  0
 G93  CONST_05  C2   C1   C12  N2    180.00   0.0  0
 G93  CONST_06  C8   C9   C12  N2    180.00   0.0  0
 G93  CONST_07  N1   C2   C1   N3    180.00   0.0  0
 G93  CONST_08  C9   C12  C1   N3    180.00   0.0  0
 G93  CONST_09  C12  N2   C15  N3      0.00   0.0  0
 G93  CONST_10  C17  C16  C15  N3      0.00   0.0  0
 G93  CONST_11  N4   C16  C15  N3    180.00   0.0  0
 G93  CONST_12  C9   C8   N1   C2      0.00   0.0  0
 G93  CONST_13  C15  N3   C1   C2    180.00   0.0  0
 G93  CONST_14  C9   C12  C1   C2      0.00   0.0  0
 G93  CONST_15  C12  C1   C2   N1      0.00   0.0  0
 G93  CONST_16  C12  C9   C8   N1      0.00   0.0  0
 G93  CONST_17  C16  C15  N3   C1    180.00   0.0  0
 G93  CONST_18  C8   N1   C2   C1      0.00   0.0  0
 G93  CONST_19  C15  N2   C12  C1      0.00   0.0  0
 G93  CONST_20  C8   C9   C12  C1      0.00   0.0  0
 G93  CONST_21  N4   O3   N5   C17     0.00   0.0  0
 G93  CONST_22  O3   N4   C16  C17     0.00   0.0  0
 G93  CONST_23  N4   C16  C17  N5      0.00   0.0  0
 G93  CONST_24  C15  C16  C17  N5    180.00   0.0  0
 G93  CONST_25  C16  N4   O3   N5      0.00   0.0  0
 G93  CONST_26  C16  C17  N5   O3      0.00   0.0  0
 G93  CONST_27  C15  C16  N4   O3    180.00   0.0  0
 G93  CONST_28  C12  N2   C15  C16   180.00   0.0  0
 G93  CONST_29  C9   C12  N2   C15   180.00   0.0  0
 G93  CONST_30  C12  C1   N3   C15     0.00   0.0  0
 G93  CONST_31  C8   N1   C2   C3    180.00   0.0  0
 G93  CONST_32  N3   C1   C2   C3      0.00   0.0  0
 G93  CONST_33  C12  C1   C2   C3    180.00   0.0  0
 G93  CONST_34  O2   C9   C12  N2      0.00   0.0  0
 G93  CONST_35  C13  N2   C15  N3    180.00   0.0  0
 G93  CONST_36  C1   C12  C9   O2    180.00   0.0  0
 G93  CONST_37  N1   C8   C9   O2    180.00   0.0  0
 G93  CONST_38  C13  N2   C12  C1    180.00   0.0  0
 G93  CONST_39  O3   N5   C17  N6    180.00   0.0  0
 G93  CONST_40  N4   C16  C17  N6    180.00   0.0  0
 G93  CONST_41  C15  C16  C17  N6      0.00   0.0  0
 G93  CONST_42  C13  N2   C15  C16     0.00   0.0  0
 G93  CONST_43  C9   C12  N2   C13     0.00   0.0  0
 G93  CONST_44  H8   C8   N1   C2    180.00   0.0  0
 G93  Var_01    C19  N7   C18  C11    62.77  30.0  1
 G93  Var_02    C19  C20  C21  C11   -53.41  30.0  1
 G93  Var_03    C20  C19  N7   C18   -62.07  30.0  1
 G93  Var_04    C21  C20  C19  N7     56.42  30.0  1
 G93  Var_05    C14  C13  N2   C15    93.62  30.0  2
 G93  Var_06    C11  C10  O2   C9   -177.71  30.0  3
 G93  Var_07    H14  C14  C13  N2    -58.94  30.0  3
 G93  Var_08    C7   C5   C4   C3    134.81  30.0  3
 G93  Var_09    H7   C7   C5   C4     59.84  30.0  3
 G93  Var_10    H6   C6   C5   C4     60.00  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
 G93  chir_01  C11  C10  C18  C21  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
 G93  plan-1  C17   0.020
 G93  plan-1  N5    0.020
 G93  plan-1  O3    0.020
 G93  plan-1  N4    0.020
 G93  plan-1  C16   0.020
 G93  plan-1  C15   0.020
 G93  plan-1  N6    0.020
 G93  plan-2  C3    0.020
 G93  plan-2  N2    0.020
 G93  plan-2  N3    0.020
 G93  plan-2  C2    0.020
 G93  plan-2  N1    0.020
 G93  plan-2  C1    0.020
 G93  plan-2  C16   0.020
 G93  plan-2  C15   0.020
 G93  plan-2  C13   0.020
 G93  plan-2  C4    0.020
 G93  plan-2  C12   0.020
 G93  plan-2  C9    0.020
 G93  plan-2  C8    0.020
 G93  plan-2  H8    0.020
 G93  plan-2  O2    0.020
 G93  plan-3  C17   0.020
 G93  plan-3  HN6   0.020
 G93  plan-3  HN6A  0.020
 G93  plan-3  N6    0.020

