# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri May  1 23:02:02 2020
#   Inital geometry file: a 136 line input string
#   Ligand name: (5S,7E,9E,11Z,14Z)-5-hydroxyicosa-7,9,11,14-tetraenoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCCC\C=C/C/C=C\C=C\C=C\C[C@@H](O)CCCC(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
 EAH  EAH  '(5S,7E,9E,11Z,14Z)-5-hydroxyicosa-7,9,11,14-tetraenoic acid'  ligand  55  23  .  2021-08-08  2023-02-16
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as GRAND
;

data_comp_EAH
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
 EAH  O1    O  O     0  -0.446    9.6844   0.4919   1.2538
 EAH  C1    C  C     0   0.550    9.5079   0.8517   0.1164
 EAH  O2    O  OH1   0  -0.598   10.4113   1.5480  -0.5687
 EAH  C2    C  CH2   0  -0.581    8.2731   0.5842  -0.6980
 EAH  C3    C  CH2   0  -0.416    7.2006  -0.1931   0.0474
 EAH  C4    C  CH2   0  -0.452    5.9843  -0.4387  -0.8365
 EAH  C5    C  CH1   0   0.040    4.8391  -1.1395  -0.1142
 EAH  O3    O  OH1   0  -0.666    5.2415  -2.3621   0.4708
 EAH  C6    C  CH2   0  -0.521    3.6367  -1.3370  -1.0445
 EAH  C7    C  C1    0  -0.204    2.4381  -1.8778  -0.3389
 EAH  C8    C  C1    0  -0.251    1.2307  -1.3002  -0.3567
 EAH  C9    C  C1    0  -0.245    0.0779  -1.8116   0.3519
 EAH  C10   C  C1    0  -0.270   -1.1414  -1.2449   0.3080
 EAH  C11   C  C1    0  -0.251   -2.2771  -1.7554   1.0457
 EAH  C12   C  C1    0  -0.207   -3.5262  -1.2693   1.0353
 EAH  C13   C  CH2   0  -0.579   -4.0552  -0.1264   0.2220
 EAH  C14   C  C1    0  -0.213   -5.0234  -0.6465  -0.8042
 EAH  C15   C  C1    0  -0.204   -6.3467  -0.4936  -0.8164
 EAH  C16   C  CH2   0  -0.489   -7.1929   0.2787   0.1458
 EAH  C17   C  CH2   0  -0.414   -8.0146   1.3573  -0.5613
 EAH  C18   C  CH2   0  -0.408   -8.8838   2.1694   0.3911
 EAH  C19   C  CH2   0  -0.420   -9.7476   3.2011  -0.3239
 EAH  C20   C  CH3   0  -0.662  -10.5890   4.0353   0.6328
 EAH  HO2   H  HOH1  0   0.478   11.1928   1.7042  -0.0180
 EAH  H2    H  HCH2  0   0.276    7.8805   1.5455  -1.0454
 EAH  H2A   H  HCH2  0   0.276    8.5737   0.0500  -1.6053
 EAH  H3    H  HCH2  0   0.231    7.6064  -1.1446   0.3947
 EAH  H3A   H  HCH2  0   0.227    6.8960   0.3613   0.9394
 EAH  H4    H  HCH2  0   0.227    5.6124   0.5169  -1.2194
 EAH  H4A   H  HCH2  0   0.222    6.2753  -1.0246  -1.7174
 EAH  H5    H  HCH1  0   0.225    4.5245  -0.5099   0.7251
 EAH  HO3   H  HOH1  0   0.441    5.5536  -2.9416  -0.2332
 EAH  H6    H  HCH2  0   0.243    3.3864  -0.3848  -1.5200
 EAH  H6A   H  HCH2  0   0.237    3.9373  -2.0165  -1.8534
 EAH  H7    H  H     0   0.242    2.5726  -2.7933   0.2312
 EAH  H8    H  H     0   0.240    1.0876  -0.3865  -0.9291
 EAH  H9    H  H     0   0.244    0.2251  -2.7037   0.9565
 EAH  H10   H  H     0   0.244   -1.2779  -0.3598  -0.3061
 EAH  H11   H  H     0   0.242   -2.0808  -2.6195   1.6742
 EAH  H12   H  H     0   0.246   -4.2647  -1.7699   1.6535
 EAH  H13   H  HCH2  0   0.257   -4.5425   0.5935   0.8837
 EAH  H13A  H  HCH2  0   0.253   -3.2469   0.4085  -0.2805
 EAH  H14   H  H     0   0.237   -4.5723  -1.2399  -1.5942
 EAH  H15   H  H     0   0.232   -6.8934  -0.9631  -1.6306
 EAH  H16   H  HCH2  0   0.231   -7.8803  -0.4099   0.6503
 EAH  H16A  H  HCH2  0   0.230   -6.5863   0.7323   0.9332
 EAH  H17   H  HCH2  0   0.217   -7.3401   2.0286  -1.1021
 EAH  H17A  H  HCH2  0   0.213   -8.6487   0.8861  -1.3201
 EAH  H18   H  HCH2  0   0.209   -9.5272   1.4928   0.9640
 EAH  H18A  H  HCH2  0   0.209   -8.2443   2.6737   1.1242
 EAH  H19   H  HCH2  0   0.211   -9.1071   3.8608  -0.9175
 EAH  H19A  H  HCH2  0   0.211  -10.4019   2.6902  -1.0374
 EAH  H20   H  HCH3  0   0.216  -11.2476   3.4039   1.2319
 EAH  H20A  H  HCH3  0   0.216   -9.9581   4.5993   1.3219
 EAH  H20B  H  HCH3  0   0.226  -11.2149   4.7506   0.0977

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
 EAH  C1   O1    double  1.206  0.020  1.206
 EAH  C1   O2    single  1.331  0.020  1.331
 EAH  O2   HO2   single  0.850  0.020  0.980
 EAH  C2   C1    single  1.503  0.020  1.503
 EAH  C2   H2    single  0.970  0.020  1.090
 EAH  C2   H2A   single  0.970  0.020  1.090
 EAH  C3   C2    single  1.520  0.020  1.520
 EAH  C3   H3    single  0.970  0.020  1.090
 EAH  C3   H3A   single  0.970  0.020  1.090
 EAH  C4   C3    single  1.523  0.020  1.523
 EAH  C4   H4    single  0.970  0.020  1.090
 EAH  C4   H4A   single  0.970  0.020  1.090
 EAH  C5   C4    single  1.525  0.020  1.525
 EAH  C5   C6    single  1.533  0.020  1.533
 EAH  C5   H5    single  0.970  0.020  1.090
 EAH  O3   C5    single  1.414  0.020  1.414
 EAH  O3   HO3   single  0.850  0.020  0.980
 EAH  C6   H6    single  0.970  0.020  1.090
 EAH  C6   H6A   single  0.970  0.020  1.090
 EAH  C7   C6    single  1.492  0.020  1.492
 EAH  C7   H7    single  0.930  0.020  1.080
 EAH  C8   C7    double  1.339  0.020  1.339
 EAH  C8   H8    single  0.930  0.020  1.080
 EAH  C9   C8    single  1.447  0.020  1.447
 EAH  C9   H9    single  0.930  0.020  1.080
 EAH  C10  C9    double  1.345  0.020  1.345
 EAH  C10  H10   single  0.930  0.020  1.080
 EAH  C11  C10   single  1.447  0.020  1.447
 EAH  C11  H11   single  0.930  0.020  1.080
 EAH  C12  C11   double  1.340  0.020  1.340
 EAH  C12  H12   single  0.930  0.020  1.080
 EAH  C13  C12   single  1.499  0.020  1.499
 EAH  C13  H13   single  0.970  0.020  1.090
 EAH  C13  H13A  single  0.970  0.020  1.090
 EAH  C14  C13   single  1.504  0.020  1.504
 EAH  C14  H14   single  0.930  0.020  1.080
 EAH  C15  C14   double  1.332  0.020  1.332
 EAH  C15  H15   single  0.930  0.020  1.080
 EAH  C16  C15   single  1.496  0.020  1.496
 EAH  C16  C17   single  1.529  0.020  1.529
 EAH  C16  H16   single  0.970  0.020  1.090
 EAH  C16  H16A  single  0.970  0.020  1.090
 EAH  C17  C18   single  1.524  0.020  1.524
 EAH  C17  H17   single  0.970  0.020  1.090
 EAH  C17  H17A  single  0.970  0.020  1.090
 EAH  C18  H18   single  0.970  0.020  1.090
 EAH  C18  H18A  single  0.970  0.020  1.090
 EAH  C19  C18   single  1.524  0.020  1.524
 EAH  C19  C20   single  1.523  0.020  1.523
 EAH  C19  H19   single  0.970  0.020  1.090
 EAH  C19  H19A  single  0.970  0.020  1.090
 EAH  C20  H20   single  0.970  0.020  1.090
 EAH  C20  H20A  single  0.970  0.020  1.090
 EAH  C20  H20B  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
 EAH  C2    C1   O2    111.83  3.000
 EAH  C2    C1   O1    125.33  3.000
 EAH  O2    C1   O1    122.84  3.000
 EAH  HO2   O2   C1    109.84  3.000
 EAH  H2A   C2   H2    105.30  3.000
 EAH  H2A   C2   C3    110.52  3.000
 EAH  H2    C2   C3    110.58  3.000
 EAH  C3    C2   C1    113.89  3.000
 EAH  H2A   C2   C1    108.08  3.000
 EAH  H2    C2   C1    108.07  3.000
 EAH  H3A   C3   H3    106.62  3.000
 EAH  H3A   C3   C4    109.42  3.000
 EAH  H3    C3   C4    109.93  3.000
 EAH  C4    C3   C2    111.18  3.000
 EAH  H3A   C3   C2    109.72  3.000
 EAH  H3    C3   C2    109.86  3.000
 EAH  H4A   C4   H4    105.98  3.000
 EAH  H4A   C4   C5    109.52  3.000
 EAH  H4    C4   C5    108.17  3.000
 EAH  C5    C4   C3    113.52  3.000
 EAH  H4A   C4   C3    109.89  3.000
 EAH  H4    C4   C3    109.48  3.000
 EAH  H5    C5   C6    108.29  3.000
 EAH  H5    C5   O3    105.17  3.000
 EAH  C6    C5   O3    111.28  3.000
 EAH  O3    C5   C4    112.32  3.000
 EAH  H5    C5   C4    108.34  3.000
 EAH  C6    C5   C4    111.16  3.000
 EAH  HO3   O3   C5    108.05  3.000
 EAH  H6A   C6   H6    106.32  3.000
 EAH  H6A   C6   C7    110.11  3.000
 EAH  H6    C6   C7    109.72  3.000
 EAH  C7    C6   C5    112.94  3.000
 EAH  H6A   C6   C5    108.18  3.000
 EAH  H6    C6   C5    109.34  3.000
 EAH  H7    C7   C8    118.82  3.000
 EAH  C8    C7   C6    124.18  3.000
 EAH  H7    C7   C6    117.00  3.000
 EAH  H8    C8   C9    116.74  3.000
 EAH  C9    C8   C7    124.04  3.000
 EAH  H8    C8   C7    119.22  3.000
 EAH  H9    C9   C10   119.10  3.000
 EAH  C10   C9   C8    123.87  3.000
 EAH  H9    C9   C8    117.03  3.000
 EAH  H10   C10  C11   118.50  3.000
 EAH  C11   C10  C9    123.09  3.000
 EAH  H10   C10  C9    118.41  3.000
 EAH  H11   C11  C12   117.48  3.000
 EAH  C12   C11  C10   126.83  3.000
 EAH  H11   C11  C10   115.69  3.000
 EAH  H12   C12  C13   114.86  3.000
 EAH  C13   C12  C11   127.56  3.000
 EAH  H12   C12  C11   117.54  3.000
 EAH  H13A  C13  H13   106.62  3.000
 EAH  H13A  C13  C14   109.39  3.000
 EAH  H13   C13  C14   110.73  3.000
 EAH  C14   C13  C12   109.50  3.000
 EAH  H13A  C13  C12   111.22  3.000
 EAH  H13   C13  C12   109.34  3.000
 EAH  H14   C14  C15   117.94  3.000
 EAH  C15   C14  C13   127.32  3.000
 EAH  H14   C14  C13   114.70  3.000
 EAH  H15   C15  C16   114.84  3.000
 EAH  C16   C15  C14   127.97  3.000
 EAH  H15   C15  C14   117.18  3.000
 EAH  H16A  C16  H16   106.11  3.000
 EAH  H16A  C16  C17   109.80  3.000
 EAH  H16   C16  C17   108.60  3.000
 EAH  H16A  C16  C15   111.33  3.000
 EAH  H16   C16  C15   109.06  3.000
 EAH  C17   C16  C15   111.75  3.000
 EAH  H17A  C17  H17   106.16  3.000
 EAH  H17A  C17  C18   109.39  3.000
 EAH  H17   C17  C18   109.48  3.000
 EAH  H17A  C17  C16   109.14  3.000
 EAH  H17   C17  C16   109.26  3.000
 EAH  C18   C17  C16   113.17  3.000
 EAH  H18A  C18  H18   106.09  3.000
 EAH  H18A  C18  C19   109.46  3.000
 EAH  H18   C18  C19   109.30  3.000
 EAH  C19   C18  C17   113.01  3.000
 EAH  H18A  C18  C17   109.30  3.000
 EAH  H18   C18  C17   109.43  3.000
 EAH  H19A  C19  H19   106.12  3.000
 EAH  H19A  C19  C20   109.57  3.000
 EAH  H19   C19  C20   109.50  3.000
 EAH  H19A  C19  C18   109.19  3.000
 EAH  H19   C19  C18   109.32  3.000
 EAH  C20   C19  C18   112.92  3.000
 EAH  H20B  C20  H20A  107.61  3.000
 EAH  H20B  C20  H20   107.60  3.000
 EAH  H20A  C20  H20   107.53  3.000
 EAH  H20B  C20  C19   111.60  3.000
 EAH  H20A  C20  C19   111.12  3.000
 EAH  H20   C20  C19   111.18  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
 EAH  CONST_01  HO2  O2   C1   O1      0.00   0.0  0
 EAH  Var_01    C9   C8   C7   C6   -178.61   0.0  2
 EAH  Var_02    C11  C10  C9   C8   -178.69   0.0  2
 EAH  Var_03    C13  C12  C11  C10     2.72   0.0  2
 EAH  Var_04    C16  C15  C14  C13     2.95   0.0  2
 EAH  Var_05    C3   C2   C1   O1      0.76  30.0  2
 EAH  Var_06    C4   C3   C2   C1   -179.56  30.0  1
 EAH  Var_07    C5   C4   C3   C2   -176.40  30.0  1
 EAH  Var_08    C8   C7   C6   C5    125.37  30.0  2
 EAH  Var_09    C10  C9   C8   C7   -178.47  30.0  1
 EAH  Var_10    C12  C11  C10  C9   -178.50  30.0  1
 EAH  Var_11    C14  C13  C12  C11   111.71  30.0  1
 EAH  Var_12    C15  C14  C13  C12   108.72  30.0  1
 EAH  Var_13    C17  C16  C15  C14   122.27  30.0  2
 EAH  Var_14    C18  C17  C16  C15  -179.69  30.0  3
 EAH  Var_15    C19  C18  C17  C16  -177.42  30.0  3
 EAH  Var_16    C20  C19  C18  C17  -178.54  30.0  2
 EAH  Var_17    H20  C20  C19  C18   -58.57  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
 EAH  chir_01  C5  C4  C6  O3  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
 EAH  plan-1  O1   0.020
 EAH  plan-1  C1   0.020
 EAH  plan-1  O2   0.020
 EAH  plan-1  C2   0.020
 EAH  plan-1  HO2  0.020
 EAH  plan-2  C6   0.020
 EAH  plan-2  C7   0.020
 EAH  plan-2  C8   0.020
 EAH  plan-2  C9   0.020
 EAH  plan-2  H7   0.020
 EAH  plan-2  H8   0.020
 EAH  plan-3  C8   0.020
 EAH  plan-3  C9   0.020
 EAH  plan-3  C10  0.020
 EAH  plan-3  C11  0.020
 EAH  plan-3  H9   0.020
 EAH  plan-3  H10  0.020
 EAH  plan-4  C10  0.020
 EAH  plan-4  C11  0.020
 EAH  plan-4  C12  0.020
 EAH  plan-4  C13  0.020
 EAH  plan-4  H11  0.020
 EAH  plan-4  H12  0.020
 EAH  plan-5  C13  0.020
 EAH  plan-5  C14  0.020
 EAH  plan-5  C15  0.020
 EAH  plan-5  C16  0.020
 EAH  plan-5  H14  0.020
 EAH  plan-5  H15  0.020

