# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon Apr  6 03:21:43 2020
#   Inital geometry file: a 112 line input string
#   Ligand name: 3-hydroxy-5-[5-(6-hydroxy-7-propyl-2H-indazol-3-yl)-1,3-thiazol-2-yl]pyridine-2-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCc1c(O)ccc2c([nH]nc12)c3sc(nc3)c4cnc(C(O)=O)c(O)c4
#
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
 57Y  57Y  '3-hydroxy-5-[5-(6-hydroxy-7-propyl-2H-indazol-3-yl)-1,3-thiazol-2-yl]pyridine-2-carboxylic acid'  ligand  43  28  .  2022-07-23  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_57Y
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
 57Y  C20  C  CR16   0  -0.336  -2.6629   1.5971   0.4525
 57Y  C21  C  CR16   0  -0.339  -3.7529   2.4072   0.5713
 57Y  C15  C  CR16   0  -0.289   4.1796  -1.3706   0.3276
 57Y  C18  C  CR16   0  -0.160   3.5683   0.8551  -0.2941
 57Y  C10  C  CR15   0  -0.002   0.0424  -2.1977   0.1614
 57Y  C19  C  CR56   0  -0.160  -2.8686   0.2799  -0.0060
 57Y  C14  C  CR6    0   0.032   3.1861  -0.4545   0.0139
 57Y  C4   C  CR6    0  -0.052  -5.3141   0.6784  -0.2032
 57Y  C5   C  CR56   0   0.226  -4.1807  -0.1672  -0.3171
 57Y  C22  C  CR6    0   0.287  -5.0671   1.9531   0.2487
 57Y  C16  C  CR6    0   0.362   5.5096  -0.9572   0.3254
 57Y  C8   C  CR5    0   0.458  -2.0563  -0.8332  -0.2462
 57Y  C9   C  CR5    0  -0.329  -0.6388  -1.0412  -0.1055
 57Y  CA   C  CR6    0  -0.144   5.7893   0.3855  -0.0064
 57Y  C12  C  CR5    0   0.023   1.7878  -0.8695   0.0038
 57Y  C    C  C      0   0.482   7.2244   0.8683  -0.0350
 57Y  C1   C  CH3    0  -0.667  -8.7653  -0.9841   0.3833
 57Y  C3   C  CH2    0  -0.531  -6.6856   0.1517  -0.5115
 57Y  C2   C  CH2    0  -0.412  -7.3794  -0.4503   0.7137
 57Y  N    N  N      0  -0.382   4.8253   1.2484  -0.3018
 57Y  N11  N  N      0  -0.388   1.3898  -2.0879   0.2155
 57Y  N7   N  NR15   0  -0.497  -2.8973  -1.7963  -0.6554
 57Y  N6   N  N      0  -0.298  -4.1722  -1.4435  -0.7108
 57Y  O    O  O     -1  -0.626   8.0861  -0.0134   0.2816
 57Y  O23  O  OH1    0  -0.630  -6.0360   2.8778   0.4300
 57Y  O17  O  OH1    0  -0.648   6.4772  -1.8083   0.6283
 57Y  OXT  O  OC     0  -0.539   7.4648   2.0305  -0.3493
 57Y  S13  S  S2     0   0.255   0.4939   0.2421  -0.2948
 57Y  H1   H  HCR6   0   0.253  -1.6800   1.9677   0.7126
 57Y  H2   H  HCR6   0   0.267  -3.6375   3.4252   0.9219
 57Y  H5   H  HCR5   0   0.283  -0.4225  -3.1571   0.3419
 57Y  H6   H  HCH3   0   0.221  -8.7145  -1.7742  -0.3677
 57Y  H7   H  HCH3   0   0.232  -9.2540  -1.3972   1.2658
 57Y  H8   H  HCH3   0   0.220  -9.4072  -0.1942  -0.0116
 57Y  H9   H  HCH2   0   0.233  -7.3239   0.9305  -0.9446
 57Y  H10  H  HCH2   0   0.255  -6.6063  -0.6113  -1.2892
 57Y  H11  H  HCH2   0   0.221  -7.4525   0.3056   1.5007
 57Y  H12  H  HCH2   0   0.229  -6.7561  -1.2531   1.1155
 57Y  H13  H  HNR5   0   0.428  -2.6370  -2.7281  -0.9442
 57Y  H14  H  HOH1   0   0.473  -6.8941   2.5421   0.1491
 57Y  H15  H  HOH1   0   0.464   7.3299  -1.2295   0.5451
 57Y  H3   H  HCR6   0   0.271   3.9307  -2.3946   0.5754
 57Y  H4   H  HCR6   0   0.253   2.8283   1.6088  -0.5473

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
 57Y  O23  C22  single    1.352  0.020  1.352
 57Y  C21  C22  aromatic  1.427  0.020  1.427
 57Y  C21  C20  aromatic  1.363  0.020  1.363
 57Y  C22  C4   aromatic  1.375  0.020  1.375
 57Y  C20  C19  aromatic  1.410  0.020  1.410
 57Y  C4   C3   single    1.501  0.020  1.501
 57Y  C4   C5   aromatic  1.419  0.020  1.419
 57Y  C2   C3   single    1.531  0.020  1.531
 57Y  C2   C1   single    1.521  0.020  1.521
 57Y  C19  C5   aromatic  1.421  0.020  1.421
 57Y  C19  C8   aromatic  1.399  0.020  1.399
 57Y  C10  N11  aromatic  1.353  0.020  1.353
 57Y  C10  C9   aromatic  1.369  0.020  1.369
 57Y  C5   N6   aromatic  1.336  0.020  1.336
 57Y  N11  C12  aromatic  1.299  0.020  1.299
 57Y  C9   C8   single    1.440  0.020  1.440
 57Y  C9   S13  aromatic  1.722  0.020  1.722
 57Y  C8   N7   aromatic  1.343  0.020  1.343
 57Y  C12  C14  single    1.459  0.020  1.459
 57Y  C12  S13  aromatic  1.732  0.020  1.732
 57Y  C15  C14  aromatic  1.387  0.020  1.387
 57Y  C15  C16  aromatic  1.393  0.020  1.393
 57Y  N6   N7   aromatic  1.324  0.020  1.324
 57Y  C14  C18  aromatic  1.399  0.020  1.399
 57Y  O17  C16  single    1.324  0.020  1.324
 57Y  C16  CA   aromatic  1.411  0.020  1.411
 57Y  C18  N    aromatic  1.317  0.020  1.317
 57Y  CA   N    aromatic  1.327  0.020  1.327
 57Y  CA   C    single    1.514  0.020  1.514
 57Y  C    O    deloc     1.273  0.020  1.273
 57Y  C    OXT  deloc     1.228  0.020  1.228
 57Y  C20  H1   single    0.930  0.020  1.080
 57Y  C21  H2   single    0.930  0.020  1.080
 57Y  C15  H3   single    0.930  0.020  1.080
 57Y  C18  H4   single    0.930  0.020  1.080
 57Y  C10  H5   single    0.930  0.020  1.080
 57Y  C1   H6   single    0.970  0.020  1.090
 57Y  C1   H7   single    0.970  0.020  1.090
 57Y  C1   H8   single    0.970  0.020  1.090
 57Y  C3   H9   single    0.970  0.020  1.090
 57Y  C3   H10  single    0.970  0.020  1.090
 57Y  C2   H11  single    0.970  0.020  1.090
 57Y  C2   H12  single    0.970  0.020  1.090
 57Y  N7   H13  single    0.860  0.020  1.020
 57Y  O23  H14  single    0.850  0.020  0.980
 57Y  O17  H15  single    0.850  0.020  0.980

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
 57Y  H1   C20  C19  122.05  3.000
 57Y  H1   C20  C21  120.11  3.000
 57Y  C19  C20  C21  117.83  3.000
 57Y  H2   C21  C22  118.06  3.000
 57Y  H2   C21  C20  120.11  3.000
 57Y  C22  C21  C20  121.83  3.000
 57Y  H3   C15  C16  120.05  3.000
 57Y  H3   C15  C14  120.77  3.000
 57Y  C16  C15  C14  119.18  3.000
 57Y  H4   C18  N    116.21  3.000
 57Y  H4   C18  C14  120.99  3.000
 57Y  N    C18  C14  122.80  3.000
 57Y  H5   C10  N11  119.58  3.000
 57Y  H5   C10  C9   124.63  3.000
 57Y  N11  C10  C9   115.78  3.000
 57Y  C8   C19  C5   104.38  3.000
 57Y  C8   C19  C20  135.61  3.000
 57Y  C5   C19  C20  120.00  3.000
 57Y  C12  C14  C18  121.80  3.000
 57Y  C18  C14  C15  118.18  3.000
 57Y  C12  C14  C15  120.02  3.000
 57Y  C3   C4   C22  123.85  3.000
 57Y  C3   C4   C5   120.28  3.000
 57Y  C22  C4   C5   115.81  3.000
 57Y  N6   C5   C4   126.75  3.000
 57Y  N6   C5   C19  111.06  3.000
 57Y  C4   C5   C19  122.19  3.000
 57Y  O23  C22  C4   123.34  3.000
 57Y  C4   C22  C21  122.32  3.000
 57Y  O23  C22  C21  114.33  3.000
 57Y  O17  C16  CA   121.37  3.000
 57Y  CA   C16  C15  118.17  3.000
 57Y  O17  C16  C15  120.45  3.000
 57Y  N7   C8   C9   122.88  3.000
 57Y  N7   C8   C19  105.04  3.000
 57Y  C9   C8   C19  132.07  3.000
 57Y  S13  C9   C8   121.96  3.000
 57Y  S13  C9   C10  108.89  3.000
 57Y  C8   C9   C10  129.15  3.000
 57Y  N    CA   C    118.48  3.000
 57Y  C    CA   C16  119.72  3.000
 57Y  N    CA   C16  121.80  3.000
 57Y  S13  C12  N11  113.65  3.000
 57Y  S13  C12  C14  122.33  3.000
 57Y  N11  C12  C14  124.01  3.000
 57Y  OXT  C    O    125.93  3.000
 57Y  OXT  C    CA   119.49  3.000
 57Y  O    C    CA   114.58  3.000
 57Y  H8   C1   H7   107.66  3.000
 57Y  H8   C1   H6   107.60  3.000
 57Y  H7   C1   H6   107.68  3.000
 57Y  H8   C1   C2   111.11  3.000
 57Y  H7   C1   C2   111.43  3.000
 57Y  H6   C1   C2   111.17  3.000
 57Y  H10  C3   H9   104.90  3.000
 57Y  H10  C3   C2   109.14  3.000
 57Y  H9   C3   C2   109.37  3.000
 57Y  H10  C3   C4   108.97  3.000
 57Y  H9   C3   C4   111.34  3.000
 57Y  C2   C3   C4   112.80  3.000
 57Y  H12  C2   H11  106.33  3.000
 57Y  H12  C2   C3   108.94  3.000
 57Y  H11  C2   C3   109.53  3.000
 57Y  H12  C2   C1   109.98  3.000
 57Y  H11  C2   C1   109.75  3.000
 57Y  C3   C2   C1   112.14  3.000
 57Y  CA   N    C18  119.86  3.000
 57Y  C12  N11  C10  112.01  3.000
 57Y  H13  N7   N6   118.83  3.000
 57Y  H13  N7   C8   126.00  3.000
 57Y  N6   N7   C8   115.13  3.000
 57Y  N7   N6   C5   104.39  3.000
 57Y  H14  O23  C22  111.17  3.000
 57Y  H15  O17  C16  102.98  3.000
 57Y  C12  S13  C9    89.67  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
 57Y  CONST_01  C4   C22  C21  C20     0.00   0.0  0
 57Y  CONST_02  C4   C5   C19  C20     0.00   0.0  0
 57Y  CONST_03  N6   C5   C19  C20   180.00   0.0  0
 57Y  CONST_04  C9   C8   C19  C20     0.00   0.0  0
 57Y  CONST_05  N7   C8   C19  C20   180.00   0.0  0
 57Y  CONST_06  C5   C4   C22  C21     0.00   0.0  0
 57Y  CONST_07  C5   C19  C20  C21     0.00   0.0  0
 57Y  CONST_08  C8   C19  C20  C21   180.00   0.0  0
 57Y  CONST_09  N11  C12  C14  C15     0.00   0.0  0
 57Y  CONST_10  S13  C12  C14  C15   180.00   0.0  0
 57Y  CONST_11  N    C18  C14  C15     0.00   0.0  0
 57Y  CONST_12  N    CA   C16  C15     0.00   0.0  0
 57Y  CONST_13  N11  C12  C14  C18   180.00   0.0  0
 57Y  CONST_14  S13  C12  C14  C18     0.00   0.0  0
 57Y  CONST_15  C16  C15  C14  C18     0.00   0.0  0
 57Y  CONST_16  C16  CA   N    C18     0.00   0.0  0
 57Y  CONST_17  C14  C12  N11  C10   180.00   0.0  0
 57Y  CONST_18  S13  C12  N11  C10     0.00   0.0  0
 57Y  CONST_21  C12  S13  C9   C10     0.00   0.0  0
 57Y  CONST_22  C22  C21  C20  C19     0.00   0.0  0
 57Y  CONST_23  C22  C4   C5   C19     0.00   0.0  0
 57Y  CONST_24  N7   N6   C5   C19     0.00   0.0  0
 57Y  CONST_26  N6   N7   C8   C19     0.00   0.0  0
 57Y  CONST_27  C9   S13  C12  C14   180.00   0.0  0
 57Y  CONST_28  CA   C16  C15  C14     0.00   0.0  0
 57Y  CONST_29  CA   N    C18  C14     0.00   0.0  0
 57Y  CONST_30  C8   C19  C5   C4    180.00   0.0  0
 57Y  CONST_31  N7   N6   C5   C4    180.00   0.0  0
 57Y  CONST_32  C9   C8   C19  C5    180.00   0.0  0
 57Y  CONST_33  N7   C8   C19  C5      0.00   0.0  0
 57Y  CONST_34  C8   N7   N6   C5      0.00   0.0  0
 57Y  CONST_35  N6   C5   C4   C22   180.00   0.0  0
 57Y  CONST_36  C12  C14  C15  C16   180.00   0.0  0
 57Y  CONST_37  N6   C5   C19  C8      0.00   0.0  0
 57Y  CONST_38  N11  C10  C9   C8    180.00   0.0  0
 57Y  CONST_39  C12  S13  C9   C8    180.00   0.0  0
 57Y  CONST_40  C12  N11  C10  C9      0.00   0.0  0
 57Y  CONST_41  N6   N7   C8   C9    180.00   0.0  0
 57Y  CONST_42  N11  C12  S13  C9      0.00   0.0  0
 57Y  CONST_43  N    C18  C14  C12   180.00   0.0  0
 57Y  CONST_44  S13  C9   C10  N11     0.00   0.0  0
 57Y  CONST_46  O23  C22  C21  C20   180.00   0.0  0
 57Y  CONST_47  C3   C4   C22  C21   180.00   0.0  0
 57Y  CONST_48  C    CA   C16  C15   180.00   0.0  0
 57Y  CONST_49  C    CA   N    C18   180.00   0.0  0
 57Y  CONST_50  C3   C4   C5   C19   180.00   0.0  0
 57Y  CONST_51  O17  C16  C15  C14   180.00   0.0  0
 57Y  CONST_52  O23  C22  C4   C5    180.00   0.0  0
 57Y  CONST_53  N6   C5   C4   C3      0.00   0.0  0
 57Y  CONST_54  O17  C16  CA   N     180.00   0.0  0
 57Y  CONST_55  H4   C18  C14  C15   180.00   0.0  0
 57Y  CONST_56  H3   C15  C14  C18   180.00   0.0  0
 57Y  CONST_57  H2   C21  C20  C19   180.00   0.0  0
 57Y  CONST_58  H13  N7   C8   C19   180.00   0.0  0
 57Y  CONST_59  H1   C20  C19  C5    180.00   0.0  0
 57Y  CONST_60  H5   C10  C9   C8      0.00   0.0  0
 57Y  Var_01    C2   C3   C4   C5     89.75  30.0  2
 57Y  Var_02    O    C    CA   C16    -1.32  30.0  2
 57Y  Var_03    C1   C2   C3   C4   -179.78  30.0  3
 57Y  Var_04    H6   C1   C2   C3     60.66  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
 57Y  plan-1  C10  0.020
 57Y  plan-1  C14  0.020
 57Y  plan-1  C8   0.020
 57Y  plan-1  C9   0.020
 57Y  plan-1  C12  0.020
 57Y  plan-1  N11  0.020
 57Y  plan-1  S13  0.020
 57Y  plan-1  H5   0.020
 57Y  plan-2  C15  0.020
 57Y  plan-2  C18  0.020
 57Y  plan-2  C14  0.020
 57Y  plan-2  C16  0.020
 57Y  plan-2  CA   0.020
 57Y  plan-2  C12  0.020
 57Y  plan-2  C    0.020
 57Y  plan-2  N    0.020
 57Y  plan-2  O17  0.020
 57Y  plan-2  H3   0.020
 57Y  plan-2  H4   0.020
 57Y  plan-3  C20  0.020
 57Y  plan-3  C21  0.020
 57Y  plan-3  C19  0.020
 57Y  plan-3  C4   0.020
 57Y  plan-3  C5   0.020
 57Y  plan-3  C22  0.020
 57Y  plan-3  C8   0.020
 57Y  plan-3  C9   0.020
 57Y  plan-3  C3   0.020
 57Y  plan-3  N7   0.020
 57Y  plan-3  N6   0.020
 57Y  plan-3  O23  0.020
 57Y  plan-3  H1   0.020
 57Y  plan-3  H2   0.020
 57Y  plan-3  H13  0.020
 57Y  plan-4  CA   0.020
 57Y  plan-4  C    0.020
 57Y  plan-4  O    0.020
 57Y  plan-4  OXT  0.020

