# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Mar 22 16:55:52 2022
#   Inital geometry file: a 151 line input string
#   Ligand name: (1aS,11S,11aR,14Z,18R)-3,8,18-trihydroxy-11a-[(1R)-1-hydroxyethyl]-7-methoxy-11,11a-dihydro-4H-11,1a-hept[3]ene[1,5]diynonaphtho[2,3-h]oxireno[c]quinoline-4,9(10H)-dione
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: COc1ccc2C(=O)c3c(O)cc4c(N[C@H]5C#C\C=C/C#C[C@@H](O)[C@@]46O[C@@]56[C@@H](C)O)c3C(=O)c2c1O
#
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
 TNN  TNN  (1aS,11S,11aR,14Z,18R)-3,8,18-trihydroxy-11a-[(1R)-1-hydroxyethyl]-7-methoxy-11,11a-dihydro-4H-11,1a-hept[3]ene[1,5]diynonaphtho[2,3-h]oxireno[c]quinoline-4,9(10H)-dione  ligand  55  36  .  2022-09-15  2022-09-16
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_TNN
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
 TNN  CAB  C  CH3   0  -0.695   5.5351   0.3200  -2.4722
 TNN  CBF  C  CH1   0  -0.013   4.7769   0.9403  -1.3066
 TNN  OAG  O  OH1   0  -0.646   4.8251   2.3454  -1.3749
 TNN  CBJ  C  CT    0   0.232   3.3140   0.4404  -1.2196
 TNN  OAT  O  O2    0  -0.452   2.9496  -0.6291  -2.0596
 TNN  CBI  C  CT    0   0.178   2.9292  -0.8600  -0.6537
 TNN  CAY  C  CR6   0   0.144   1.5321  -1.0393  -0.1299
 TNN  CAQ  C  CR16  0  -0.411   1.1677  -2.1445   0.5895
 TNN  CAU  C  CR6   0   0.392  -0.1650  -2.3800   0.9681
 TNN  OAE  O  OH1   0  -0.623  -0.4004  -3.4859   1.6669
 TNN  CBC  C  CR66  0  -0.252  -1.1558  -1.4859   0.5781
 TNN  CAZ  C  CR6   0   0.392  -2.5376  -1.7655   0.9581
 TNN  OAC  O  O     0  -0.471  -2.8231  -2.7807   1.6016
 TNN  CBB  C  CR66  0  -0.034  -3.5764  -0.8146   0.5697
 TNN  CAP  C  CR16  0  -0.293  -4.8927  -1.0605   0.9033
 TNN  CAO  C  CR16  0  -0.371  -5.8924  -0.1605   0.5477
 TNN  CAW  C  CR6   0   0.343  -5.5820   0.9964  -0.1432
 TNN  OAS  O  O2    0  -0.448  -6.4575   1.9230  -0.5318
 TNN  CAA  C  CH3   0  -0.444  -7.8269   1.7304  -0.2193
 TNN  CAV  C  CR6   0   0.288  -4.2348   1.2651  -0.4963
 TNN  OAF  O  OH1   0  -0.607  -4.0114   2.3897  -1.1608
 TNN  CBD  C  CR66  0  -0.167  -3.2347   0.3561  -0.1386
 TNN  CBA  C  CR6   0   0.439  -1.8473   0.6286  -0.5228
 TNN  OAD  O  O     0  -0.516  -1.5945   1.6622  -1.1655
 TNN  CBE  C  CR66  0  -0.114  -0.8033  -0.3155  -0.1517
 TNN  CAX  C  CR6   0   0.298   0.5407  -0.0761  -0.4897
 TNN  NAR  N  NH1   0  -0.674   0.9496   1.0323  -1.1575
 TNN  CBH  C  CH1   0  -0.309   2.2823   1.5383  -0.9662
 TNN  CAL  C  CSP   0   0.132   2.5375   1.9222   0.4337
 TNN  CAJ  C  CSP   0   0.082   2.8039   1.9314   1.6108
 TNN  CAN  C  C1    0  -0.414   3.2040   1.7231   2.9549
 TNN  CAM  C  C1    0  -0.414   3.7918   0.5610   3.3098
 TNN  CAI  C  CSP   0   0.127   4.0075  -0.4391   2.3300
 TNN  CAK  C  CSP   0   0.040   4.0851  -1.1602   1.3649
 TNN  CBG  C  CH1   0  -0.173   4.0430  -1.6822  -0.0114
 TNN  OAH  O  OH1   0  -0.644   3.8230  -3.0544  -0.1552
 TNN  HAF  H  HCH3  0   0.252   6.5601   0.6898  -2.4690
 TNN  HAD  H  HCH3  0   0.243   5.5799  -0.7663  -2.4288
 TNN  HAE  H  HCH3  0   0.241   5.0754   0.5901  -3.4254
 TNN  HBF  H  HCH1  0   0.256   5.2795   0.6918  -0.3687
 TNN  HAG  H  HOH1  0   0.453   4.6676   2.6194  -2.2854
 TNN  HAQ  H  HCR6  0   0.291   1.8961  -2.8928   0.8634
 TNN  HBI  H  HOH1  0   0.483  -1.3735  -3.5219   1.8309
 TNN  HAP  H  HCR6  0   0.273  -5.1609  -1.9574   1.4432
 TNN  HAO  H  HCR6  0   0.301  -6.9140  -0.3841   0.8213
 TNN  HAA  H  HCH3  0   0.238  -8.2233   0.8262  -0.6868
 TNN  HAB  H  HCH3  0   0.238  -7.9894   1.6764   0.8593
 TNN  HAC  H  HCH3  0   0.268  -8.3549   2.5940  -0.6140
 TNN  HBJ  H  HOH1  0   0.488  -3.0418   2.4274  -1.3394
 TNN  HAR  H  HNH1  0   0.423   0.2344   1.7212  -1.3442
 TNN  HBH  H  HCH1  0   0.310   2.4033   2.3794  -1.6464
 TNN  HAN  H  H     0   0.293   3.0410   2.4970   3.6940
 TNN  HAM  H  H     0   0.296   4.0998   0.3926   4.3336
 TNN  HBG  H  HCH1  0   0.279   4.9938  -1.4135  -0.4841
 TNN  HAH  H  HOH1  0   0.473   4.5999  -3.5241   0.1678

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
 TNN  CAB  CBF  single    1.523  0.020  1.523
 TNN  CBF  OAG  single    1.408  0.020  1.408
 TNN  CBF  CBJ  single    1.548  0.020  1.548
 TNN  CBJ  OAT  single    1.408  0.020  1.408
 TNN  CBJ  CBI  single    1.469  0.020  1.469
 TNN  CBJ  CBH  single    1.528  0.020  1.528
 TNN  OAT  CBI  single    1.425  0.020  1.425
 TNN  CBI  CAY  single    1.503  0.020  1.503
 TNN  CBI  CBG  single    1.526  0.020  1.526
 TNN  CAY  CAQ  aromatic  1.368  0.020  1.368
 TNN  CAY  CAX  aromatic  1.428  0.020  1.428
 TNN  CAQ  CAU  aromatic  1.405  0.020  1.405
 TNN  CAU  OAE  single    1.329  0.020  1.329
 TNN  CAU  CBC  aromatic  1.390  0.020  1.390
 TNN  CBC  CAZ  single    1.460  0.020  1.460
 TNN  CBC  CBE  aromatic  1.424  0.020  1.424
 TNN  CAZ  OAC  double    1.235  0.020  1.235
 TNN  CAZ  CBB  single    1.461  0.020  1.461
 TNN  CBB  CAP  aromatic  1.380  0.020  1.380
 TNN  CBB  CBD  aromatic  1.410  0.020  1.410
 TNN  CAP  CAO  aromatic  1.391  0.020  1.391
 TNN  CAO  CAW  aromatic  1.383  0.020  1.383
 TNN  CAW  OAS  single    1.333  0.020  1.333
 TNN  CAW  CAV  aromatic  1.418  0.020  1.418
 TNN  OAS  CAA  single    1.418  0.020  1.418
 TNN  CAV  OAF  single    1.325  0.020  1.325
 TNN  CAV  CBD  aromatic  1.398  0.020  1.398
 TNN  CBD  CBA  single    1.465  0.020  1.465
 TNN  CBA  OAD  double    1.243  0.020  1.243
 TNN  CBA  CBE  single    1.456  0.020  1.456
 TNN  CBE  CAX  aromatic  1.406  0.020  1.406
 TNN  CAX  NAR  single    1.357  0.020  1.357
 TNN  NAR  CBH  single    1.438  0.020  1.438
 TNN  CBH  CAL  single    1.474  0.020  1.474
 TNN  CAJ  CAN  single    1.418  0.020  1.418
 TNN  CAN  CAM  double    1.350  0.020  1.350
 TNN  CAM  CAI  single    1.417  0.020  1.417
 TNN  CAK  CBG  single    1.473  0.020  1.473
 TNN  CBG  OAH  single    1.397  0.020  1.397
 TNN  CAL  CAJ  triple    1.207  0.020  1.207
 TNN  CAB  HAF  single    0.970  0.020  1.090
 TNN  CAB  HAD  single    0.970  0.020  1.090
 TNN  CAB  HAE  single    0.970  0.020  1.090
 TNN  CBF  HBF  single    0.970  0.020  1.090
 TNN  OAG  HAG  single    0.850  0.020  0.980
 TNN  CAQ  HAQ  single    0.930  0.020  1.080
 TNN  OAE  HBI  single    0.850  0.020  0.980
 TNN  CAP  HAP  single    0.930  0.020  1.080
 TNN  CAO  HAO  single    0.930  0.020  1.080
 TNN  CAA  HAA  single    0.970  0.020  1.090
 TNN  CAA  HAB  single    0.970  0.020  1.090
 TNN  CAA  HAC  single    0.970  0.020  1.090
 TNN  OAF  HBJ  single    0.850  0.020  0.980
 TNN  NAR  HAR  single    0.890  0.020  1.040
 TNN  CBH  HBH  single    0.970  0.020  1.090
 TNN  CAN  HAN  single    0.930  0.020  1.080
 TNN  CAM  HAM  single    0.930  0.020  1.080
 TNN  CBG  HBG  single    0.970  0.020  1.090
 TNN  OAH  HAH  single    0.850  0.020  0.980
 TNN  CAI  CAK  triple    1.207  0.020  1.207

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
 TNN  HAE  CAB  HAD  107.40  3.000
 TNN  HAE  CAB  HAF  108.34  3.000
 TNN  HAD  CAB  HAF  107.46  3.000
 TNN  HAE  CAB  CBF  110.97  3.000
 TNN  HAD  CAB  CBF  113.37  3.000
 TNN  HAF  CAB  CBF  109.14  3.000
 TNN  HBF  CBF  CBJ  108.24  3.000
 TNN  HBF  CBF  OAG  104.65  3.000
 TNN  CBJ  CBF  OAG  110.94  3.000
 TNN  HBF  CBF  CAB  109.60  3.000
 TNN  CBJ  CBF  CAB  112.45  3.000
 TNN  OAG  CBF  CAB  110.63  3.000
 TNN  HAG  OAG  CBF  108.91  3.000
 TNN  CBH  CBJ  CBI  113.28  3.000
 TNN  CBH  CBJ  OAT  118.04  3.000
 TNN  CBI  CBJ  OAT   59.32  3.000
 TNN  CBH  CBJ  CBF  114.54  3.000
 TNN  CBI  CBJ  CBF  123.69  3.000
 TNN  OAT  CBJ  CBF  117.15  3.000
 TNN  CBI  OAT  CBJ   62.49  3.000
 TNN  CBG  CBI  CAY  117.87  3.000
 TNN  CBG  CBI  OAT  119.48  3.000
 TNN  CAY  CBI  OAT  112.12  3.000
 TNN  CBG  CBI  CBJ  116.60  3.000
 TNN  CAY  CBI  CBJ  118.90  3.000
 TNN  OAT  CBI  CBJ   58.19  3.000
 TNN  CAX  CAY  CAQ  119.49  3.000
 TNN  CAX  CAY  CBI  118.49  3.000
 TNN  CAQ  CAY  CBI  121.82  3.000
 TNN  HAQ  CAQ  CAU  117.08  3.000
 TNN  HAQ  CAQ  CAY  120.91  3.000
 TNN  CAU  CAQ  CAY  121.98  3.000
 TNN  CBC  CAU  OAE  123.80  3.000
 TNN  CBC  CAU  CAQ  119.50  3.000
 TNN  OAE  CAU  CAQ  116.68  3.000
 TNN  HBI  OAE  CAU  106.99  3.000
 TNN  CBE  CBC  CAZ  121.68  3.000
 TNN  CBE  CBC  CAU  119.74  3.000
 TNN  CAZ  CBC  CAU  118.57  3.000
 TNN  CBB  CAZ  OAC  120.60  3.000
 TNN  CBB  CAZ  CBC  118.63  3.000
 TNN  OAC  CAZ  CBC  120.77  3.000
 TNN  CBD  CBB  CAP  120.03  3.000
 TNN  CBD  CBB  CAZ  120.11  3.000
 TNN  CAP  CBB  CAZ  119.87  3.000
 TNN  HAP  CAP  CAO  119.09  3.000
 TNN  HAP  CAP  CBB  120.36  3.000
 TNN  CAO  CAP  CBB  120.55  3.000
 TNN  HAO  CAO  CAW  120.78  3.000
 TNN  HAO  CAO  CAP  118.72  3.000
 TNN  CAW  CAO  CAP  120.50  3.000
 TNN  CAV  CAW  OAS  114.82  3.000
 TNN  CAV  CAW  CAO  119.74  3.000
 TNN  OAS  CAW  CAO  125.44  3.000
 TNN  CAA  OAS  CAW  118.42  3.000
 TNN  HAC  CAA  HAB  109.01  3.000
 TNN  HAC  CAA  HAA  109.04  3.000
 TNN  HAB  CAA  HAA  109.13  3.000
 TNN  HAC  CAA  OAS  106.35  3.000
 TNN  HAB  CAA  OAS  111.60  3.000
 TNN  HAA  CAA  OAS  111.63  3.000
 TNN  CBD  CAV  OAF  124.02  3.000
 TNN  CBD  CAV  CAW  119.52  3.000
 TNN  OAF  CAV  CAW  116.47  3.000
 TNN  HBJ  OAF  CAV  106.79  3.000
 TNN  CBA  CBD  CAV  119.30  3.000
 TNN  CBA  CBD  CBB  121.03  3.000
 TNN  CAV  CBD  CBB  119.66  3.000
 TNN  CBE  CBA  OAD  121.68  3.000
 TNN  CBE  CBA  CBD  119.45  3.000
 TNN  OAD  CBA  CBD  118.87  3.000
 TNN  CAX  CBE  CBA  120.91  3.000
 TNN  CAX  CBE  CBC  119.98  3.000
 TNN  CBA  CBE  CBC  119.10  3.000
 TNN  NAR  CAX  CBE  123.04  3.000
 TNN  NAR  CAX  CAY  117.75  3.000
 TNN  CBE  CAX  CAY  119.21  3.000
 TNN  HAR  NAR  CBH  116.14  3.000
 TNN  HAR  NAR  CAX  115.76  3.000
 TNN  CBH  NAR  CAX  120.07  3.000
 TNN  HBH  CBH  CAL  111.90  3.000
 TNN  HBH  CBH  NAR  106.96  3.000
 TNN  CAL  CBH  NAR  112.23  3.000
 TNN  HBH  CBH  CBJ  112.12  3.000
 TNN  CAL  CBH  CBJ  103.17  3.000
 TNN  NAR  CBH  CBJ  110.54  3.000
 TNN  CAJ  CAL  CBH  180.00  3.000
 TNN  CAN  CAJ  CAL  180.00  3.000
 TNN  HAN  CAN  CAM  120.11  3.000
 TNN  HAN  CAN  CAJ  119.98  3.000
 TNN  CAM  CAN  CAJ  119.91  3.000
 TNN  HAM  CAM  CAI  120.07  3.000
 TNN  HAM  CAM  CAN  120.43  3.000
 TNN  CAI  CAM  CAN  119.49  3.000
 TNN  CAK  CAI  CAM  180.00  3.000
 TNN  CBG  CAK  CAI  180.00  3.000
 TNN  HBG  CBG  OAH  109.46  3.000
 TNN  HBG  CBG  CAK  106.95  3.000
 TNN  OAH  CBG  CAK  116.67  3.000
 TNN  HBG  CBG  CBI  108.65  3.000
 TNN  OAH  CBG  CBI  111.77  3.000
 TNN  CAK  CBG  CBI  102.90  3.000
 TNN  HAH  OAH  CBG  108.50  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
 TNN  CONST_01  CBC  CAU  CAQ  CAY     0.00   0.0  0
 TNN  CONST_02  CBC  CBE  CAX  CAY     0.00   0.0  0
 TNN  CONST_03  CBE  CAX  CAY  CAQ     0.00   0.0  0
 TNN  CONST_04  CBE  CBC  CAU  CAQ     0.00   0.0  0
 TNN  CONST_05  CAX  CAY  CAQ  CAU     0.00   0.0  0
 TNN  CONST_06  CAX  CBE  CBC  CAU     0.00   0.0  0
 TNN  CONST_07  CAW  CAO  CAP  CBB     0.00   0.0  0
 TNN  CONST_08  CAW  CAV  CBD  CBB     0.00   0.0  0
 TNN  CONST_09  CAV  CBD  CBB  CAP     0.00   0.0  0
 TNN  CONST_10  CAV  CAW  CAO  CAP     0.00   0.0  0
 TNN  CONST_11  CBD  CBB  CAP  CAO     0.00   0.0  0
 TNN  CONST_12  CBD  CAV  CAW  CAO     0.00   0.0  0
 TNN  CONST_13  OAE  CAU  CAQ  CAY   180.00   0.0  0
 TNN  CONST_14  CAZ  CBC  CAU  OAE     0.00   0.0  0
 TNN  CONST_15  CBE  CBC  CAU  OAE   180.00   0.0  0
 TNN  CONST_16  OAF  CAV  CBD  CBB   180.00   0.0  0
 TNN  CONST_17  OAS  CAW  CAO  CAP   180.00   0.0  0
 TNN  CONST_18  OAF  CAV  CAW  CAO   180.00   0.0  0
 TNN  CONST_19  CBD  CAV  CAW  OAS   180.00   0.0  0
 TNN  CONST_20  CBA  CBD  CAV  OAF     0.00   0.0  0
 TNN  CONST_21  HAQ  CAQ  CAY  CBI     0.00   0.0  0
 TNN  CONST_22  HAP  CAP  CBB  CAZ     0.00   0.0  0
 TNN  CONST_23  HAO  CAO  CAP  CBB   180.00   0.0  0
 TNN  Var_01    CAY  CBI  OAT  CBJ   111.21  30.0  3
 TNN  Var_02    CAQ  CAY  CBI  OAT   125.31  30.0  2
 TNN  Var_03    CAU  CAQ  CAY  CBI  -173.62  30.0  1
 TNN  Var_04    CBE  CAX  CAY  CBI   172.03  30.0  1
 TNN  Var_05    CBH  NAR  CAX  CAY   -28.55  30.0  1
 TNN  Var_06    CAZ  CBC  CAU  CAQ   178.70  30.0  1
 TNN  Var_07    CBB  CAZ  CBC  CAU   178.91  30.0  2
 TNN  Var_08    CAP  CBB  CAZ  CBC   179.32  30.0  2
 TNN  Var_09    CBD  CBA  CBE  CBC     0.02  30.0  2
 TNN  Var_10    CAO  CAP  CBB  CAZ   179.61  30.0  1
 TNN  Var_11    CAV  CBD  CBB  CAZ  -179.49  30.0  1
 TNN  Var_12    CBE  CBA  CBD  CBB    -0.83  30.0  2
 TNN  Var_13    HAA  CAA  OAS  CAW   -61.68  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
 TNN  chir_01  CBF  CAB  OAG  CBJ  negativ
 TNN  chir_04  CBH  CBJ  NAR  CAL  negativ
 TNN  chir_05  CBG  OAH  CBI  CAK  negativ
 TNN  chir_06  CBJ  OAT  CBI  CBH  both

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
 TNN  plan-1  CBC  0.020
 TNN  plan-1  CAZ  0.020
 TNN  plan-1  OAC  0.020
 TNN  plan-1  CBB  0.020
 TNN  plan-2  CBD  0.020
 TNN  plan-2  CBA  0.020
 TNN  plan-2  OAD  0.020
 TNN  plan-2  CBE  0.020

