# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Mar 18 18:54:43 2022
#   Inital geometry file: a 109 line input string
#   Ligand name: (4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1c(C)c2COC(=O)c2c(O)c1C\C=C(C)\CCC(O)=O
#
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
 MOA  MOA  '(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoic acid'  ligand  42  23  .  2022-03-22  2022-03-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_MOA
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
 MOA  C1    C  CR5    0   0.569  -2.0728  -0.6877  -3.2851
 MOA  C2    C  C1     0  -0.326   0.2908   0.3125   1.5660
 MOA  C3    C  C      0   0.096  -0.4334   0.8641   2.5492
 MOA  C4    C  CH2    0  -0.474  -0.9931   0.0043   3.6502
 MOA  C5    C  CH2    0  -0.579  -0.2540   0.2041   4.9712
 MOA  C6    C  C      0   0.414  -0.7881  -0.6262   6.1531
 MOA  C7    C  CH3    0  -0.748   2.6699  -0.9981  -3.9370
 MOA  C8    C  CH3    0  -0.415   3.6311   1.3884  -1.7649
 MOA  C9    C  CH3    0  -0.728  -0.7049   2.3350   2.6772
 MOA  C10   C  CH2    0  -0.192  -0.3414  -1.3029  -4.6621
 MOA  C11   C  CR56   0   0.015   0.2293  -0.7364  -3.4037
 MOA  C12   C  CR6    0  -0.043   1.5490  -0.5802  -3.0325
 MOA  C13   C  CR6    0   0.276   1.7540  -0.0084  -1.7687
 MOA  C14   C  CR6    0  -0.101   0.7105   0.3754  -0.9112
 MOA  C15   C  CR6    0   0.293  -0.6112   0.1771  -1.3300
 MOA  C16   C  CR56   0  -0.200  -0.8266  -0.3726  -2.5900
 MOA  C17   C  CH2    0  -0.570   0.9870   1.0130   0.4307
 MOA  O1    O  O      0  -0.429  -3.2193  -0.5412  -2.9534
 MOA  O2    O  O      0  -0.463  -1.7541  -1.2217  -4.4807
 MOA  O3    O  O2     0  -0.488   3.0333   0.1675  -1.3442
 MOA  O4    O  OH1    0  -0.605  -1.6739   0.5104  -0.5888
 MOA  O5    O  OC    -1  -0.628  -0.0419  -0.6928   7.1522
 MOA  O6    O  O      0  -0.608  -1.9160  -1.1439   6.0368
 MOA  H21   H  H      0   0.246   0.4328  -0.7657   1.5892
 MOA  H41   H  HCH2   0   0.222  -2.0514   0.2395   3.7916
 MOA  H42   H  HCH2   0   0.226  -0.9405  -1.0472   3.3579
 MOA  H51   H  HCH2   0   0.221   0.8085  -0.0167   4.8319
 MOA  H52   H  HCH2   0   0.232  -0.2930   1.2588   5.2674
 MOA  H71   H  HCH3   0   0.249   2.4417  -1.9452  -4.4277
 MOA  H72   H  HCH3   0   0.254   2.8389  -0.2621  -4.7260
 MOA  H73   H  HCH3   0   0.259   3.6058  -1.1250  -3.3979
 MOA  H81   H  HCH3   0   0.247   4.6541   1.3879  -1.3952
 MOA  H82   H  HCH3   0   0.231   3.6486   1.4762  -2.8540
 MOA  H83   H  HCH3   0   0.229   3.1050   2.2538  -1.3537
 MOA  H91   H  HCH3   0   0.245  -0.4826   2.9012   1.7748
 MOA  H92   H  HCH3   0   0.242  -1.7510   2.5081   2.9364
 MOA  H93   H  HCH3   0   0.252  -0.1093   2.7669   3.4847
 MOA  H1O1  H  HCH2   0   0.272  -0.0603  -0.7327  -5.5504
 MOA  H102  H  HCH2   0   0.270  -0.0598  -2.3464  -4.8219
 MOA  H171  H  HCH2   0   0.281   2.0602   0.9928   0.6239
 MOA  H172  H  HCH2   0   0.274   0.7146   2.0712   0.3929
 MOA  HO41  H  HOH1   0   0.479  -1.4177   0.6113   0.3433

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
 MOA  C1   C16   single    1.461  0.020  1.461
 MOA  C1   O1    double    1.202  0.020  1.202
 MOA  C1   O2    single    1.348  0.020  1.348
 MOA  C2   C3    double    1.340  0.020  1.340
 MOA  C2   C17   single    1.505  0.020  1.505
 MOA  C2   H21   single    0.930  0.020  1.080
 MOA  C3   C4    single    1.505  0.020  1.505
 MOA  C3   C9    single    1.501  0.020  1.501
 MOA  C4   C5    single    1.527  0.020  1.527
 MOA  C4   H41   single    0.970  0.020  1.090
 MOA  C4   H42   single    0.970  0.020  1.090
 MOA  C5   C6    single    1.540  0.020  1.540
 MOA  C5   H51   single    0.970  0.020  1.090
 MOA  C5   H52   single    0.970  0.020  1.090
 MOA  C6   O5    deloc     1.249  0.020  1.249
 MOA  C6   O6    deloc     1.246  0.020  1.246
 MOA  C7   C12   single    1.500  0.020  1.500
 MOA  C7   H71   single    0.970  0.020  1.090
 MOA  C7   H72   single    0.970  0.020  1.090
 MOA  C7   H73   single    0.970  0.020  1.090
 MOA  C8   O3    single    1.423  0.020  1.423
 MOA  C8   H81   single    0.970  0.020  1.090
 MOA  C8   H82   single    0.970  0.020  1.090
 MOA  C8   H83   single    0.970  0.020  1.090
 MOA  C9   H91   single    0.970  0.020  1.090
 MOA  C9   H92   single    0.970  0.020  1.090
 MOA  C9   H93   single    0.970  0.020  1.090
 MOA  C10  C11   single    1.493  0.020  1.493
 MOA  C10  O2    single    1.427  0.020  1.427
 MOA  C10  H1O1  single    0.970  0.020  1.090
 MOA  C10  H102  single    0.970  0.020  1.090
 MOA  C11  C12   aromatic  1.380  0.020  1.380
 MOA  C11  C16   aromatic  1.382  0.020  1.382
 MOA  C12  C13   aromatic  1.402  0.020  1.402
 MOA  C13  C14   aromatic  1.404  0.020  1.404
 MOA  C13  O3    single    1.359  0.020  1.359
 MOA  C14  C15   aromatic  1.401  0.020  1.401
 MOA  C14  C17   single    1.511  0.020  1.511
 MOA  C15  C16   aromatic  1.391  0.020  1.391
 MOA  C15  O4    single    1.338  0.020  1.338
 MOA  C17  H171  single    0.970  0.020  1.090
 MOA  C17  H172  single    0.970  0.020  1.090
 MOA  O4   HO41  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
 MOA  O2    C1   O1    121.23  3.000
 MOA  O2    C1   C16   107.80  3.000
 MOA  O1    C1   C16   130.97  3.000
 MOA  H21   C2   C17   114.66  3.000
 MOA  H21   C2   C3    117.58  3.000
 MOA  C17   C2   C3    127.73  3.000
 MOA  C9    C3   C4    115.48  3.000
 MOA  C9    C3   C2    124.31  3.000
 MOA  C4    C3   C2    120.17  3.000
 MOA  H42   C4   H41   106.75  3.000
 MOA  H42   C4   C5    109.52  3.000
 MOA  H41   C4   C5    109.18  3.000
 MOA  H42   C4   C3    109.65  3.000
 MOA  H41   C4   C3    109.36  3.000
 MOA  C5    C4   C3    112.22  3.000
 MOA  H52   C5   H51   105.26  3.000
 MOA  H52   C5   C6    107.40  3.000
 MOA  H51   C5   C6    109.01  3.000
 MOA  H52   C5   C4    110.03  3.000
 MOA  H51   C5   C4    109.48  3.000
 MOA  C6    C5   C4    115.19  3.000
 MOA  O6    C6   O5    126.39  3.000
 MOA  O6    C6   C5    117.78  3.000
 MOA  O5    C6   C5    115.82  3.000
 MOA  H73   C7   H72   107.67  3.000
 MOA  H73   C7   H71   107.56  3.000
 MOA  H72   C7   H71   107.01  3.000
 MOA  H73   C7   C12   112.14  3.000
 MOA  H72   C7   C12   111.32  3.000
 MOA  H71   C7   C12   110.91  3.000
 MOA  H83   C8   H82   108.60  3.000
 MOA  H83   C8   H81   108.98  3.000
 MOA  H82   C8   H81   108.89  3.000
 MOA  H83   C8   O3    111.46  3.000
 MOA  H82   C8   O3    111.73  3.000
 MOA  H81   C8   O3    107.11  3.000
 MOA  H93   C9   H92   106.52  3.000
 MOA  H93   C9   H91   107.21  3.000
 MOA  H92   C9   H91   108.07  3.000
 MOA  H93   C9   C3    110.60  3.000
 MOA  H92   C9   C3    110.42  3.000
 MOA  H91   C9   C3    113.71  3.000
 MOA  H102  C10  H1O1  108.26  3.000
 MOA  H102  C10  O2    109.15  3.000
 MOA  H1O1  C10  O2    109.18  3.000
 MOA  H102  C10  C11   112.77  3.000
 MOA  H1O1  C10  C11   112.89  3.000
 MOA  O2    C10  C11   104.46  3.000
 MOA  C16   C11  C12   122.87  3.000
 MOA  C16   C11  C10   107.70  3.000
 MOA  C12   C11  C10   129.43  3.000
 MOA  C13   C12  C11   115.37  3.000
 MOA  C13   C12  C7    123.22  3.000
 MOA  C11   C12  C7    121.41  3.000
 MOA  O3    C13  C14   118.25  3.000
 MOA  O3    C13  C12   118.16  3.000
 MOA  C14   C13  C12   123.59  3.000
 MOA  C17   C14  C15   119.86  3.000
 MOA  C17   C14  C13   121.45  3.000
 MOA  C15   C14  C13   118.69  3.000
 MOA  O4    C15  C16   118.50  3.000
 MOA  O4    C15  C14   123.27  3.000
 MOA  C16   C15  C14   118.21  3.000
 MOA  C15   C16  C11   121.26  3.000
 MOA  C15   C16  C1    130.38  3.000
 MOA  C11   C16  C1    108.35  3.000
 MOA  H172  C17  H171  105.61  3.000
 MOA  H172  C17  C14   109.40  3.000
 MOA  H171  C17  C14   109.23  3.000
 MOA  H172  C17  C2    111.19  3.000
 MOA  H171  C17  C2    108.24  3.000
 MOA  C14   C17  C2    112.89  3.000
 MOA  C10   O2   C1    111.69  3.000
 MOA  C13   O3   C8    114.46  3.000
 MOA  HO41  O4   C15   110.36  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
 MOA  CONST_01  C14  C13  C12  C11     0.00   0.0  0
 MOA  CONST_02  C14  C15  C16  C11     0.00   0.0  0
 MOA  CONST_03  C15  C16  C11  C12     0.00   0.0  0
 MOA  CONST_04  C15  C14  C13  C12     0.00   0.0  0
 MOA  CONST_05  C16  C11  C12  C13     0.00   0.0  0
 MOA  CONST_06  C16  C15  C14  C13     0.00   0.0  0
 MOA  CONST_07  O4   C15  C16  C1      0.00   0.0  0
 MOA  CONST_08  C10  C11  C12  C7      0.00   0.0  0
 MOA  CONST_09  C16  C11  C12  C7    180.00   0.0  0
 MOA  CONST_10  C14  C13  C12  C7    180.00   0.0  0
 MOA  CONST_11  O3   C13  C12  C11   180.00   0.0  0
 MOA  CONST_12  O4   C15  C16  C11   180.00   0.0  0
 MOA  CONST_13  C17  C14  C13  C12   180.00   0.0  0
 MOA  CONST_14  O4   C15  C14  C13   180.00   0.0  0
 MOA  CONST_15  O3   C13  C14  C15   180.00   0.0  0
 MOA  CONST_16  C17  C14  C15  C16   180.00   0.0  0
 MOA  Var_01    C11  C10  O2   C1     -0.16  30.0  1
 MOA  Var_02    C16  C1   O2   C10     0.18  30.0  1
 MOA  Var_03    O2   C1   C16  C11    -0.12  30.0  1
 MOA  Var_04    O2   C10  C11  C12   179.45  30.0  1
 MOA  Var_05    C13  C14  C17  C2   -127.13  30.0  2
 MOA  Var_06    C12  C13  O3   C8     86.38  30.0  2
 MOA  Var_07    H71  C7   C12  C11   -40.59  30.0  2
 MOA  Var_08    C14  C17  C2   C3   -132.09  30.0  3
 MOA  Var_09    H81  C8   O3   C13  -177.88  30.0  3
 MOA  Var_10    C17  C2   C3   C4   -176.49   0.0  2
 MOA  Var_11    C5   C4   C3   C2    107.23  30.0  3
 MOA  Var_12    C6   C5   C4   C3    178.96  30.0  3
 MOA  Var_13    O5   C6   C5   C4    165.63  30.0  3
 MOA  Var_14    H91  C9   C3   C2     14.76  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
 MOA  plan-1  C5   0.020
 MOA  plan-1  C6   0.020
 MOA  plan-1  O5   0.020
 MOA  plan-1  O6   0.020
 MOA  plan-2  C1   0.020
 MOA  plan-2  C7   0.020
 MOA  plan-2  C10  0.020
 MOA  plan-2  C11  0.020
 MOA  plan-2  C12  0.020
 MOA  plan-2  C13  0.020
 MOA  plan-2  C14  0.020
 MOA  plan-2  C15  0.020
 MOA  plan-2  C16  0.020
 MOA  plan-2  C17  0.020
 MOA  plan-2  O3   0.020
 MOA  plan-2  O4   0.020
 MOA  plan-3  C1   0.020
 MOA  plan-3  C16  0.020
 MOA  plan-3  O1   0.020
 MOA  plan-3  O2   0.020
 MOA  plan-4  C2   0.020
 MOA  plan-4  C3   0.020
 MOA  plan-4  C4   0.020
 MOA  plan-4  C9   0.020
 MOA  plan-4  C17  0.020
 MOA  plan-4  H21  0.020

