# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Mar 18 06:28:03 2020
#   Inital geometry file: a 150 line input string
#   Ligand name: 7-(6-methoxypyridin-3-yl)-4-{[2-(propan-2-yloxy)ethyl]amino}-1-(2-propoxyethyl)pyrido[4,3-d]pyrimidin-2(1H)-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCOCCN1C(=O)N=C(NCCOC(C)C)c2cnc(cc12)c3ccc(OC)nc3
#
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
 0H3  0H3  7-(6-methoxypyridin-3-yl)-4-{[2-(propan-2-yloxy)ethyl]amino}-1-(2-propoxyethyl)pyrido[4,3-d]pyrimidin-2(1H)-one  ligand  63  32  .  2021-08-03  2021-08-03  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_0H3
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
 0H3  N3   N  NR6   0  -0.611   0.1315   1.8531  -1.6911
 0H3  C4   C  CH3   0  -0.686   7.2999  -3.0998   1.0944
 0H3  N2   N  N     0  -0.446  -0.6365  -1.7968   0.1570
 0H3  C7   C  CR6   0   0.249  -1.6506  -1.0121  -0.2346
 0H3  C6   C  CR16  0  -0.092   0.5883  -1.3796  -0.0684
 0H3  C9   C  CR66  0  -0.163   0.9075  -0.1765  -0.6926
 0H3  C13  C  CH2   0  -0.384  -0.9412   2.7762  -2.0392
 0H3  C20  C  CR16  0  -0.096  -4.1229  -1.0868  -0.6481
 0H3  C21  C  CR16  0  -0.379  -4.4858  -2.9345   1.3046
 0H3  C8   C  CR16  0  -0.429  -1.4497   0.2152  -0.8448
 0H3  N5   N  N     0  -0.460  -5.3579  -1.5154  -0.4080
 0H3  C18  C  CR6   0  -0.048  -3.0034  -1.5184   0.0471
 0H3  C16  C  CH2   0  -0.462   0.4659   5.3868   1.6642
 0H3  C19  C  CR16  0  -0.157  -3.2165  -2.4838   1.0424
 0H3  O1   O  O2    0  -0.498   5.3731  -2.2160  -0.1145
 0H3  C1   C  CH1   0   0.047   5.7881  -3.0938   0.9211
 0H3  C2   C  CH2   0  -0.178   5.5739  -0.8472   0.1404
 0H3  C3   C  CH3   0  -0.675   5.2590  -4.4715   0.5713
 0H3  C5   C  CH2   0  -0.296   4.6765  -0.0555  -0.7859
 0H3  C10  C  CR66  0   0.558  -0.1461   0.6585  -1.0924
 0H3  C11  C  CR6   0   0.585   1.4551   2.2577  -1.9189
 0H3  N4   N  N     0  -0.541   2.4715   1.4508  -1.5234
 0H3  C12  C  CR6   0   0.554   2.2547   0.3013  -0.9423
 0H3  O2   O  O     0  -0.490   1.6753   3.3136  -2.4854
 0H3  C14  C  CH2   0  -0.145  -1.4723   3.5292  -0.8330
 0H3  O3   O  O2    0  -0.475  -0.4086   4.1895  -0.2073
 0H3  C15  C  CH2   0  -0.118  -0.7620   4.7712   1.0248
 0H3  C17  C  CH3   0  -0.673   0.1387   5.9930   3.0222
 0H3  C22  C  CR6   0   0.539  -5.5390  -2.4057   0.5451
 0H3  O4   O  O2    0  -0.467  -6.7651  -2.8412   0.8182
 0H3  C23  C  CH3   0  -0.419  -7.8532  -2.3079   0.0743
 0H3  H8   H  HCH3  0   0.234   7.5840  -3.8108   1.8709
 0H3  H9   H  HCH3  0   0.225   7.7967  -3.3966   0.1682
 0H3  H7   H  HCH3  0   0.237   7.6856  -2.1238   1.3919
 0H3  H12  H  HCR6  0   0.257   1.3712  -2.0489   0.2724
 0H3  H15  H  HCH2  0   0.290  -0.5483   3.4743  -2.7715
 0H3  H16  H  HCH2  0   0.274  -1.7523   2.2359  -2.5271
 0H3  H27  H  HCR6  0   0.262  -4.0327  -0.3716  -1.4580
 0H3  H28  H  HCR6  0   0.278  -4.6747  -3.6688   2.0757
 0H3  H14  H  HCR6  0   0.284  -2.3019   0.8233  -1.1031
 0H3  H22  H  HCH2  0   0.224   1.2364   4.6193   1.7750
 0H3  H21  H  HCH2  0   0.224   0.8765   6.1553   1.0041
 0H3  H26  H  HCR6  0   0.272  -2.3797  -2.8645   1.6119
 0H3  H1   H  HCH1  0   0.203   5.3285  -2.7666   1.8657
 0H3  H3   H  HCH2  0   0.213   5.3316  -0.6051   1.1839
 0H3  H2   H  HCH2  0   0.229   6.6117  -0.5415  -0.0349
 0H3  H5   H  HCH3  0   0.229   5.4930  -5.1764   1.3687
 0H3  H6   H  HCH3  0   0.234   4.1760  -4.4603   0.4420
 0H3  H4   H  HCH3  0   0.225   5.7124  -4.8442  -0.3490
 0H3  H11  H  HCH2  0   0.260   4.8017   1.0065  -0.5803
 0H3  H10  H  HCH2  0   0.249   4.9607  -0.2202  -1.8299
 0H3  H13  H  HNH1  0   0.405   3.1487  -1.3766  -0.2461
 0H3  H18  H  HCH2  0   0.221  -2.2448   4.2292  -1.1813
 0H3  H17  H  HCH2  0   0.206  -1.9675   2.8430  -0.1317
 0H3  H19  H  HCH2  0   0.192  -1.1900   4.0123   1.6970
 0H3  H20  H  HCH2  0   0.193  -1.5374   5.5391   0.8850
 0H3  H25  H  HCH3  0   0.235   1.0253   6.4243   3.4857
 0H3  H24  H  HCH3  0   0.222  -0.6061   6.7855   2.9340
 0H3  H23  H  HCH3  0   0.221  -0.2585   5.2406   3.7060
 0H3  H31  H  HCH3  0   0.232  -7.9436  -1.2295   0.2082
 0H3  H29  H  HCH3  0   0.233  -7.7592  -2.5223  -0.9905
 0H3  H30  H  HCH3  0   0.249  -8.7437  -2.7950   0.4624
 0H3  N1   N  NH1   0  -0.654   3.2973  -0.4335  -0.5660

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
 0H3  C17  C16  single    1.523  0.020  1.523
 0H3  C23  O4   single    1.422  0.020  1.422
 0H3  C15  C16  single    1.515  0.020  1.515
 0H3  C15  O3   single    1.408  0.020  1.408
 0H3  N5   C22  aromatic  1.317  0.020  1.317
 0H3  N5   C20  aromatic  1.329  0.020  1.329
 0H3  C14  O3   single    1.400  0.020  1.400
 0H3  C14  C13  single    1.518  0.020  1.518
 0H3  O4   C22  single    1.330  0.020  1.330
 0H3  C22  C21  aromatic  1.402  0.020  1.402
 0H3  C20  C18  aromatic  1.387  0.020  1.387
 0H3  C13  N3   single    1.457  0.020  1.457
 0H3  C21  C19  aromatic  1.372  0.020  1.372
 0H3  C18  C19  aromatic  1.403  0.020  1.403
 0H3  C18  C7   single    1.472  0.020  1.472
 0H3  C8   C7   aromatic  1.385  0.020  1.385
 0H3  C8   C10  aromatic  1.399  0.020  1.399
 0H3  N3   C10  single    1.365  0.020  1.365
 0H3  N3   C11  single    1.403  0.020  1.403
 0H3  O2   C11  double    1.218  0.020  1.218
 0H3  C7   N2   aromatic  1.341  0.020  1.341
 0H3  C10  C9   aromatic  1.403  0.020  1.403
 0H3  C11  N4   single    1.357  0.020  1.357
 0H3  N2   C6   aromatic  1.313  0.020  1.313
 0H3  C9   C6   aromatic  1.392  0.020  1.392
 0H3  C9   C12  single    1.451  0.020  1.451
 0H3  N4   C12  double    1.306  0.020  1.306
 0H3  C12  N1   single    1.330  0.020  1.330
 0H3  N1   C5   single    1.447  0.020  1.447
 0H3  C4   C1   single    1.522  0.020  1.522
 0H3  C5   C2   single    1.513  0.020  1.513
 0H3  C2   O1   single    1.407  0.020  1.407
 0H3  O1   C1   single    1.420  0.020  1.420
 0H3  C1   C3   single    1.517  0.020  1.517
 0H3  C4   H8   single    0.970  0.020  1.090
 0H3  C4   H9   single    0.970  0.020  1.090
 0H3  C4   H7   single    0.970  0.020  1.090
 0H3  C6   H12  single    0.930  0.020  1.080
 0H3  C13  H15  single    0.970  0.020  1.090
 0H3  C13  H16  single    0.970  0.020  1.090
 0H3  C20  H27  single    0.930  0.020  1.080
 0H3  C21  H28  single    0.930  0.020  1.080
 0H3  C8   H14  single    0.930  0.020  1.080
 0H3  C16  H22  single    0.970  0.020  1.090
 0H3  C16  H21  single    0.970  0.020  1.090
 0H3  C19  H26  single    0.930  0.020  1.080
 0H3  C1   H1   single    0.970  0.020  1.090
 0H3  C2   H3   single    0.970  0.020  1.090
 0H3  C2   H2   single    0.970  0.020  1.090
 0H3  C3   H5   single    0.970  0.020  1.090
 0H3  C3   H6   single    0.970  0.020  1.090
 0H3  C3   H4   single    0.970  0.020  1.090
 0H3  C5   H11  single    0.970  0.020  1.090
 0H3  C5   H10  single    0.970  0.020  1.090
 0H3  N1   H13  single    0.860  0.020  1.020
 0H3  C14  H18  single    0.970  0.020  1.090
 0H3  C14  H17  single    0.970  0.020  1.090
 0H3  C15  H19  single    0.970  0.020  1.090
 0H3  C15  H20  single    0.970  0.020  1.090
 0H3  C17  H25  single    0.970  0.020  1.090
 0H3  C17  H24  single    0.970  0.020  1.090
 0H3  C17  H23  single    0.970  0.020  1.090
 0H3  C23  H31  single    0.970  0.020  1.090
 0H3  C23  H29  single    0.970  0.020  1.090
 0H3  C23  H30  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
 0H3  C11  N3   C10  121.04  3.000
 0H3  C11  N3   C13  118.24  3.000
 0H3  C10  N3   C13  120.63  3.000
 0H3  H7   C4   H9   108.27  3.000
 0H3  H7   C4   H8   107.28  3.000
 0H3  H9   C4   H8   107.96  3.000
 0H3  H7   C4   C1   112.26  3.000
 0H3  H9   C4   C1   110.88  3.000
 0H3  H8   C4   C1   110.03  3.000
 0H3  C6   N2   C7   117.99  3.000
 0H3  C18  C7   C8   121.50  3.000
 0H3  C8   C7   N2   122.52  3.000
 0H3  C18  C7   N2   115.97  3.000
 0H3  H12  C6   C9   120.56  3.000
 0H3  H12  C6   N2   115.03  3.000
 0H3  C9   C6   N2   124.41  3.000
 0H3  C12  C9   C10  116.90  3.000
 0H3  C12  C9   C6   125.06  3.000
 0H3  C10  C9   C6   118.03  3.000
 0H3  H16  C13  H15  106.64  3.000
 0H3  H16  C13  C14  109.96  3.000
 0H3  H15  C13  C14  110.11  3.000
 0H3  H16  C13  N3   109.91  3.000
 0H3  H15  C13  N3   107.58  3.000
 0H3  C14  C13  N3   112.45  3.000
 0H3  H27  C20  C18  120.84  3.000
 0H3  H27  C20  N5   115.15  3.000
 0H3  C18  C20  N5   124.00  3.000
 0H3  H28  C21  C22  120.74  3.000
 0H3  H28  C21  C19  121.39  3.000
 0H3  C22  C21  C19  117.86  3.000
 0H3  H14  C8   C10  121.02  3.000
 0H3  H14  C8   C7   119.38  3.000
 0H3  C10  C8   C7   119.59  3.000
 0H3  C22  N5   C20  118.47  3.000
 0H3  C19  C18  C20  116.57  3.000
 0H3  C19  C18  C7   120.81  3.000
 0H3  C20  C18  C7   122.61  3.000
 0H3  H21  C16  H22  106.86  3.000
 0H3  H21  C16  C17  109.84  3.000
 0H3  H22  C16  C17  109.92  3.000
 0H3  H21  C16  C15  109.58  3.000
 0H3  H22  C16  C15  109.19  3.000
 0H3  C17  C16  C15  111.34  3.000
 0H3  H26  C19  C18  119.89  3.000
 0H3  H26  C19  C21  119.97  3.000
 0H3  C18  C19  C21  120.14  3.000
 0H3  C2   O1   C1   115.32  3.000
 0H3  H1   C1   C3   108.81  3.000
 0H3  H1   C1   O1   108.68  3.000
 0H3  C3   C1   O1   106.94  3.000
 0H3  H1   C1   C4   108.57  3.000
 0H3  C3   C1   C4   111.67  3.000
 0H3  O1   C1   C4   112.08  3.000
 0H3  H2   C2   H3   107.42  3.000
 0H3  H2   C2   C5   108.52  3.000
 0H3  H3   C2   C5   109.60  3.000
 0H3  H2   C2   O1   112.19  3.000
 0H3  H3   C2   O1   110.81  3.000
 0H3  C5   C2   O1   108.27  3.000
 0H3  H4   C3   H6   108.42  3.000
 0H3  H4   C3   H5   107.86  3.000
 0H3  H6   C3   H5   107.86  3.000
 0H3  H4   C3   C1   111.08  3.000
 0H3  H6   C3   C1   111.37  3.000
 0H3  H5   C3   C1   110.11  3.000
 0H3  H10  C5   H11  107.27  3.000
 0H3  H10  C5   N1   110.68  3.000
 0H3  H11  C5   N1   109.62  3.000
 0H3  H10  C5   C2   110.56  3.000
 0H3  H11  C5   C2   109.05  3.000
 0H3  N1   C5   C2   109.61  3.000
 0H3  C8   C10  C9   117.44  3.000
 0H3  C9   C10  N3   119.56  3.000
 0H3  C8   C10  N3   122.99  3.000
 0H3  O2   C11  N4   121.04  3.000
 0H3  N4   C11  N3   119.22  3.000
 0H3  O2   C11  N3   119.74  3.000
 0H3  C12  N4   C11  121.92  3.000
 0H3  N4   C12  N1   118.82  3.000
 0H3  N1   C12  C9   119.82  3.000
 0H3  N4   C12  C9   121.36  3.000
 0H3  H17  C14  H18  106.45  3.000
 0H3  H17  C14  O3   110.59  3.000
 0H3  H18  C14  O3   112.04  3.000
 0H3  H17  C14  C13  110.80  3.000
 0H3  H18  C14  C13  108.06  3.000
 0H3  O3   C14  C13  108.87  3.000
 0H3  C15  O3   C14  113.29  3.000
 0H3  H20  C15  H19  106.55  3.000
 0H3  H20  C15  O3   110.74  3.000
 0H3  H19  C15  O3   110.33  3.000
 0H3  H20  C15  C16  109.95  3.000
 0H3  H19  C15  C16  109.73  3.000
 0H3  O3   C15  C16  109.50  3.000
 0H3  H23  C17  H24  107.64  3.000
 0H3  H23  C17  H25  107.61  3.000
 0H3  H24  C17  H25  107.59  3.000
 0H3  H23  C17  C16  111.25  3.000
 0H3  H24  C17  C16  111.33  3.000
 0H3  H25  C17  C16  111.23  3.000
 0H3  O4   C22  N5   119.81  3.000
 0H3  O4   C22  C21  117.25  3.000
 0H3  N5   C22  C21  122.95  3.000
 0H3  C23  O4   C22  118.38  3.000
 0H3  H30  C23  H29  109.35  3.000
 0H3  H30  C23  H31  109.36  3.000
 0H3  H29  C23  H31  108.76  3.000
 0H3  H30  C23  O4   105.79  3.000
 0H3  H29  C23  O4   111.79  3.000
 0H3  H31  C23  O4   111.72  3.000
 0H3  H13  N1   C12  119.46  3.000
 0H3  H13  N1   C5   115.70  3.000
 0H3  C12  N1   C5   124.05  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
 0H3  CONST_03  C10  C8   C7   N2      0.00   0.0  0
 0H3  CONST_04  C10  C9   C6   N2      0.00   0.0  0
 0H3  CONST_05  N5   C20  C18  C7    180.00   0.0  0
 0H3  CONST_06  C21  C19  C18  C7    180.00   0.0  0
 0H3  CONST_07  C9   C10  C8   C7      0.00   0.0  0
 0H3  CONST_08  C9   C6   N2   C7      0.00   0.0  0
 0H3  CONST_09  C18  C7   N2   C6    180.00   0.0  0
 0H3  CONST_10  C8   C7   N2   C6      0.00   0.0  0
 0H3  CONST_11  C8   C10  C9   C6      0.00   0.0  0
 0H3  CONST_12  C21  C22  N5   C20     0.00   0.0  0
 0H3  CONST_13  C21  C19  C18  C20     0.00   0.0  0
 0H3  CONST_16  C19  C21  C22  N5      0.00   0.0  0
 0H3  CONST_17  C19  C18  C20  N5      0.00   0.0  0
 0H3  CONST_18  C22  N5   C20  C18     0.00   0.0  0
 0H3  CONST_19  C22  C21  C19  C18     0.00   0.0  0
 0H3  CONST_20  C10  C8   C7   C18   180.00   0.0  0
 0H3  CONST_21  C12  N4   C11  N3      0.00   0.0  0
 0H3  CONST_22  C11  N4   C12  C9      0.00   0.0  0
 0H3  CONST_23  N4   C11  N3   C10     0.00   0.0  0
 0H3  CONST_24  O4   C22  N5   C20   180.00   0.0  0
 0H3  CONST_25  O4   C22  C21  C19   180.00   0.0  0
 0H3  CONST_26  N4   C11  N3   C13   180.00   0.0  0
 0H3  CONST_27  C11  N4   C12  N1    180.00   0.0  0
 0H3  CONST_28  O2   C11  N3   C10   180.00   0.0  0
 0H3  CONST_29  O2   C11  N4   C12   180.00   0.0  0
 0H3  CONST_30  H14  C8   C10  N3      0.00   0.0  0
 0H3  CONST_31  H27  C20  C18  C7      0.00   0.0  0
 0H3  CONST_32  H26  C19  C18  C7      0.00   0.0  0
 0H3  CONST_33  H12  C6   N2   C7    180.00   0.0  0
 0H3  CONST_34  H28  C21  C22  N5    180.00   0.0  0
 0H3  CONST_35  C5   N1   C12  C9    180.00   0.0  0
 0H3  CONST_36  O2   C11  N3   C13     0.00   0.0  0
 0H3  CONST_37  N4   C12  N1   C5      0.00   0.0  0
 0H3  CONST_38  H13  N1   C12  C9      0.00   0.0  0
 0H3  Var_01    C14  C13  N3   C10    76.91  30.0  2
 0H3  Var_02    O3   C14  C13  N3     55.86  30.0  2
 0H3  Var_03    C12  N1   C5   C2    161.30  30.0  1
 0H3  Var_04    H31  C23  O4   C22   -60.84  30.0  3
 0H3  Var_05    N1   C5   C2   O1     58.46  30.0  1
 0H3  Var_06    C5   C2   O1   C1   -160.53  30.0  1
 0H3  Var_07    C3   C1   O1   C2    169.72  30.0  3
 0H3  Var_08    C17  C16  C15  O3   -178.30  30.0  3
 0H3  Var_09    H5   C3   C1   C4     60.76  30.0  3
 0H3  Var_10    H8   C4   C1   O1   -177.91  30.0  3
 0H3  Var_11    H19  C15  O3   C14    55.71  30.0  2
 0H3  Var_12    H25  C17  C16  C15   179.31  30.0  3

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
 0H3  plan-1  C7   0.020
 0H3  plan-1  C20  0.020
 0H3  plan-1  C21  0.020
 0H3  plan-1  N5   0.020
 0H3  plan-1  C18  0.020
 0H3  plan-1  C19  0.020
 0H3  plan-1  C22  0.020
 0H3  plan-1  O4   0.020
 0H3  plan-1  H27  0.020
 0H3  plan-1  H28  0.020
 0H3  plan-1  H26  0.020
 0H3  plan-2  N3   0.020
 0H3  plan-2  N2   0.020
 0H3  plan-2  C7   0.020
 0H3  plan-2  C6   0.020
 0H3  plan-2  C9   0.020
 0H3  plan-2  C13  0.020
 0H3  plan-2  C8   0.020
 0H3  plan-2  C18  0.020
 0H3  plan-2  C5   0.020
 0H3  plan-2  C10  0.020
 0H3  plan-2  C11  0.020
 0H3  plan-2  N4   0.020
 0H3  plan-2  C12  0.020
 0H3  plan-2  O2   0.020
 0H3  plan-2  H12  0.020
 0H3  plan-2  H14  0.020
 0H3  plan-2  H13  0.020
 0H3  plan-2  N1   0.020

