# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Oct  9 04:55:46 2022
#   Inital geometry file: a 228 line input string
#   Ligand name: (3R,5S,9R)-1-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]-3,5,9-trihydroxy-8,8-dimethyl-10,14,19-trioxo-2,4,6-trioxa-18-thia-11,15-diaza-3,5-diphosphatricosan-23-oic acid 3,5-dioxide (non-preferred name)
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)(CO[P@@](O)(=O)O[P@@](O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O[P](O)(O)=O)n2cnc3c(N)ncnc23)[C@@H](O)C(=O)NCCC(=O)NCCSC(=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
 GRA  GRA  "glutaryl-coenzyme A"  ligand  98  56  .  2022-11-17  2022-11-17
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_GRA
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
 GRA  O9A   O  OH1   0  -0.648  -82.5526  92.5342  -51.7402
 GRA  P3X   P  P     0   1.390  -83.5413  91.6964  -50.8063
 GRA  O7A   O  OH1   0  -0.694  -83.9265  90.4885  -51.7681
 GRA  O8A   O  O     0  -0.707  -84.6326  92.4424  -50.1590
 GRA  O3X   O  O2    0  -0.631  -82.6581  90.9512  -49.7006
 GRA  C3X   C  CR15  0  -0.049  -81.4917  90.1979  -49.9446
 GRA  C2X   C  CR15  0   0.002  -80.2132  91.0392  -50.1324
 GRA  O2X   O  OH1   0  -0.619  -80.2866  92.3067  -49.5576
 GRA  C4X   C  CR15  0  -0.039  -81.1737  89.3727  -48.7009
 GRA  O4X   O  O     0  -0.500  -79.7954  89.0917  -48.8146
 GRA  C1X   C  CR15  0   0.102  -79.1313  90.1398  -49.4747
 GRA  N9A   N  NR5   0  -0.489  -78.1888  89.5531  -50.3920
 GRA  C4A   C  CR56  0   0.412  -76.8261  89.6733  -50.3384
 GRA  N3A   N  N     0  -0.404  -76.1021  90.3975  -49.4917
 GRA  C2A   C  CR16  0   0.015  -74.8068  90.2668  -49.7221
 GRA  C8A   C  CR15  0   0.171  -78.4562  88.6801  -51.4098
 GRA  N7A   N  N     0  -0.524  -77.3872  88.2473  -52.0087
 GRA  C5A   C  CR56  0   0.104  -76.3467  88.8620  -51.3554
 GRA  C6A   C  CR6   0   0.285  -74.9474  88.8262  -51.5143
 GRA  N6A   N  NH2   0  -0.798  -74.3270  88.1062  -52.4519
 GRA  N1A   N  N     0  -0.357  -74.2064  89.5461  -50.6626
 GRA  C5X   C  CH2   0  -0.187  -81.9525  88.0848  -48.6444
 GRA  O5X   O  O2    0  -0.593  -81.6150  87.4155  -47.4266
 GRA  P1A   P  P     0   1.442  -82.1747  85.9861  -47.0282
 GRA  O1A   O  OH1   0  -0.649  -83.7578  86.0122  -47.2042
 GRA  O2A   O  O     0  -0.633  -81.6492  85.5306  -45.7364
 GRA  O3A   O  O2    0  -0.683  -81.7777  85.1177  -48.3310
 GRA  P2A   P  P     0   1.413  -82.3193  83.6363  -48.7442
 GRA  O4A   O  OH1   0  -0.661  -83.6005  83.9094  -49.6358
 GRA  O5A   O  O     0  -0.745  -82.4685  82.7509  -47.5792
 GRA  O6A   O  O2    0  -0.621  -81.3062  83.2584  -49.8899
 GRA  C13   C  CH2   0  -0.144  -79.8966  83.1052  -49.6696
 GRA  C12   C  CT    0  -0.148  -79.1904  83.0206  -51.0210
 GRA  C15   C  CH3   0  -0.655  -79.6604  81.7499  -51.7352
 GRA  C16   C  CH3   0  -0.684  -77.6919  82.9148  -50.7201
 GRA  C14   C  CH1   0  -0.011  -79.5144  84.2964  -51.8509
 GRA  O1    O  OH1   0  -0.655  -79.4655  85.4749  -51.0830
 GRA  C1    C  C     0   0.474  -78.6523  84.3809  -53.1167
 GRA  O2    O  O     0  -0.533  -78.7314  83.5251  -53.9901
 GRA  N1    N  NH1   0  -0.557  -77.8408  85.4387  -53.2106
 GRA  C2    C  CH2   0  -0.268  -76.9012  85.6175  -54.2891
 GRA  C3    C  CH2   0  -0.586  -75.5957  84.8713  -54.0208
 GRA  C4    C  C     0   0.553  -74.4766  85.3248  -54.9298
 GRA  O3    O  O     0  -0.488  -74.2797  86.5130  -55.1592
 GRA  N2    N  NH1   0  -0.667  -73.7025  84.3526  -55.4340
 GRA  C5    C  CH2   0  -0.251  -72.5165  84.6092  -56.2153
 GRA  C6    C  CH2   0  -0.566  -71.3087  84.9087  -55.3314
 GRA  S1    S  S2    0   0.020  -69.8332  85.2849  -56.3083
 GRA  C7    C  C     0   0.274  -69.2781  83.6637  -56.7860
 GRA  O4    O  O     0  -0.465  -69.7773  82.6521  -56.3692
 GRA  C8    C  CH2   0  -0.502  -68.1516  83.7188  -57.7836
 GRA  C9    C  CH2   0  -0.427  -67.3619  82.4199  -57.8926
 GRA  C10   C  CH2   0  -0.470  -66.2112  82.5281  -58.8808
 GRA  C11   C  C     0   0.504  -66.6430  82.6099  -60.3210
 GRA  O5    O  O     0  -0.498  -67.7529  82.3707  -60.7272
 GRA  O6    O  OH1   0  -0.506  -65.6319  82.9330  -61.1220
 GRA  HO9A  H  HOH1  0   0.530  -82.2362  93.3617  -51.3513
 GRA  HO7A  H  HOH1  0   0.519  -84.5231  90.7110  -52.4959
 GRA  H3X   H  HCR5  0   0.290  -81.6221  89.5332  -50.8066
 GRA  H2X   H  HCR5  0   0.287  -79.9907  91.2000  -51.1876
 GRA  HO2X  H  HOH1  0   0.454  -80.5138  92.2478  -48.6223
 GRA  H4X   H  HCR5  0   0.317  -81.3799  89.9716  -47.8017
 GRA  H1X   H  HCR5  0   0.311  -78.5366  90.7413  -48.7795
 GRA  H2A   H  HCR6  0   0.275  -74.1456  90.8215  -49.0647
 GRA  H8A   H  HCR5  0   0.262  -79.4642  88.3830  -51.6601
 GRA  HN6A  H  HNH2  0   0.367  -73.3305  88.2054  -52.5572
 GRA  HN6B  H  HNH2  0   0.383  -74.8226  87.6914  -53.2247
 GRA  H5X   H  HCH2  0   0.230  -83.0214  88.3087  -48.6703
 GRA  H5XA  H  HCH2  0   0.233  -81.7041  87.4628  -49.5087
 GRA  HO1A  H  HOH1  0   0.562  -84.2527  86.2353  -46.4027
 GRA  HO4A  H  HOH1  0   0.522  -84.4417  83.7548  -49.1836
 GRA  H13   H  HCH2  0   0.161  -79.5156  83.9322  -49.0667
 GRA  H13A  H  HCH2  0   0.309  -79.7188  82.1799  -49.1163
 GRA  H15   H  HCH3  0   0.246  -79.0649  81.5395  -52.6186
 GRA  H15A  H  HCH3  0   0.240  -79.5675  80.8948  -51.0628
 GRA  H15B  H  HCH3  0   0.269  -80.7032  81.8181  -52.0471
 GRA  H16   H  HCH3  0   0.213  -77.1158  82.7637  -51.6329
 GRA  H16A  H  HCH3  0   0.258  -77.2970  83.8000  -50.2161
 GRA  H16B  H  HCH3  0   0.237  -77.4935  82.0626  -50.0680
 GRA  H14   H  HCH1  0   0.265  -80.5484  84.2187  -52.2012
 GRA  HO1   H  HOH1  0   0.473  -78.6610  85.5027  -50.5523
 GRA  HN1   H  HNH1  0   0.382  -77.8425  86.1654  -52.5091
 GRA  H2    H  HCH2  0   0.276  -77.3414  85.2862  -55.2297
 GRA  H2B   H  HCH2  0   0.243  -76.7153  86.6863  -54.3777
 GRA  H3    H  HCH2  0   0.294  -75.2706  85.0810  -52.9962
 GRA  H3A   H  HCH2  0   0.241  -75.7588  83.7942  -54.0833
 GRA  HN2   H  HNH1  0   0.395  -73.8979  83.3978  -55.1791
 GRA  H5    H  HCH2  0   0.259  -72.3258  83.7299  -56.8275
 GRA  H5A   H  HCH2  0   0.296  -72.6985  85.4430  -56.8929
 GRA  H6    H  HCH2  0   0.323  -71.4886  85.7959  -54.7219
 GRA  H6A   H  HCH2  0   0.271  -71.0910  84.0798  -54.6583
 GRA  H8    H  HCH2  0   0.303  -68.6050  83.9815  -58.7448
 GRA  H8B   H  HCH2  0   0.253  -67.4887  84.5520  -57.5326
 GRA  H9    H  HCH2  0   0.276  -66.9463  82.1671  -56.9157
 GRA  H9A   H  HCH2  0   0.176  -68.0181  81.5962  -58.1739
 GRA  H10   H  HCH2  0   0.152  -65.5720  83.3832  -58.6467
 GRA  H10A  H  HCH2  0   0.301  -65.5648  81.6485  -58.7915
 GRA  HO6   H  HOH1  0   0.500  -65.9299  82.9384  -62.0439

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
 GRA  O9A  P3X   single    1.597  0.020  1.597
 GRA  P3X  O7A   single    1.591  0.020  1.591
 GRA  P3X  O8A   double    1.472  0.020  1.472
 GRA  P3X  O3X   single    1.599  0.020  1.599
 GRA  O3X  C3X   single    1.410  0.020  1.410
 GRA  C3X  C2X   single    1.542  0.020  1.542
 GRA  C3X  C4X   single    1.526  0.020  1.526
 GRA  C2X  O2X   single    1.394  0.020  1.394
 GRA  C2X  C1X   single    1.553  0.020  1.553
 GRA  C4X  O4X   single    1.411  0.020  1.411
 GRA  C4X  C5X   single    1.506  0.020  1.506
 GRA  O4X  C1X   single    1.405  0.020  1.405
 GRA  C1X  N9A   single    1.440  0.020  1.440
 GRA  N9A  C4A   aromatic  1.369  0.020  1.369
 GRA  N9A  C8A   aromatic  1.367  0.020  1.367
 GRA  C4A  N3A   aromatic  1.329  0.020  1.329
 GRA  C4A  C5A   aromatic  1.386  0.020  1.386
 GRA  N3A  C2A   aromatic  1.322  0.020  1.322
 GRA  C2A  N1A   aromatic  1.328  0.020  1.328
 GRA  C8A  N7A   aromatic  1.299  0.020  1.299
 GRA  N7A  C5A   aromatic  1.374  0.020  1.374
 GRA  C5A  C6A   aromatic  1.409  0.020  1.409
 GRA  C6A  N6A   single    1.335  0.020  1.335
 GRA  C6A  N1A   aromatic  1.339  0.020  1.339
 GRA  C5X  O5X   single    1.430  0.020  1.430
 GRA  O5X  P1A   single    1.586  0.020  1.586
 GRA  P1A  O1A   single    1.593  0.020  1.593
 GRA  P1A  O2A   double    1.467  0.020  1.467
 GRA  P1A  O3A   single    1.615  0.020  1.615
 GRA  O3A  P2A   single    1.631  0.020  1.631
 GRA  P2A  O4A   single    1.585  0.020  1.585
 GRA  P2A  O5A   double    1.471  0.020  1.471
 GRA  P2A  O6A   single    1.575  0.020  1.575
 GRA  O6A  C13   single    1.435  0.020  1.435
 GRA  C13  C12   single    1.527  0.020  1.527
 GRA  C12  C15   single    1.532  0.020  1.532
 GRA  C12  C16   single    1.532  0.020  1.532
 GRA  C12  C14   single    1.556  0.020  1.556
 GRA  C14  O1    single    1.407  0.020  1.407
 GRA  C14  C1    single    1.534  0.020  1.534
 GRA  C1   O2    double    1.225  0.020  1.225
 GRA  C1   N1    single    1.337  0.020  1.337
 GRA  N1   C2    single    1.441  0.020  1.441
 GRA  C2   C3    single    1.528  0.020  1.528
 GRA  C3   C4    single    1.511  0.020  1.511
 GRA  C4   O3    double    1.226  0.020  1.226
 GRA  C4   N2    single    1.341  0.020  1.341
 GRA  N2   C5    single    1.443  0.020  1.443
 GRA  C5   C6    single    1.526  0.020  1.526
 GRA  C6   S1    single    1.809  0.020  1.809
 GRA  S1   C7    single    1.779  0.020  1.779
 GRA  C7   O4    double    1.203  0.020  1.203
 GRA  C7   C8    single    1.506  0.020  1.506
 GRA  C8   C9    single    1.524  0.020  1.524
 GRA  C9   C10   single    1.521  0.020  1.521
 GRA  C10  C11   single    1.506  0.020  1.506
 GRA  C11  O5    double    1.206  0.020  1.206
 GRA  C11  O6    single    1.330  0.020  1.330
 GRA  O9A  HO9A  single    0.850  0.020  0.980
 GRA  O7A  HO7A  single    0.850  0.020  0.980
 GRA  C3X  H3X   single    0.970  0.020  1.090
 GRA  C2X  H2X   single    0.970  0.020  1.090
 GRA  O2X  HO2X  single    0.850  0.020  0.980
 GRA  C4X  H4X   single    0.970  0.020  1.090
 GRA  C1X  H1X   single    0.970  0.020  1.090
 GRA  C2A  H2A   single    0.930  0.020  1.080
 GRA  C8A  H8A   single    0.930  0.020  1.080
 GRA  N6A  HN6A  single    0.860  0.020  1.020
 GRA  N6A  HN6B  single    0.860  0.020  1.020
 GRA  C5X  H5X   single    0.970  0.020  1.090
 GRA  C5X  H5XA  single    0.970  0.020  1.090
 GRA  O1A  HO1A  single    0.850  0.020  0.980
 GRA  O4A  HO4A  single    0.850  0.020  0.980
 GRA  C13  H13   single    0.970  0.020  1.090
 GRA  C13  H13A  single    0.970  0.020  1.090
 GRA  C15  H15   single    0.970  0.020  1.090
 GRA  C15  H15A  single    0.970  0.020  1.090
 GRA  C15  H15B  single    0.970  0.020  1.090
 GRA  C16  H16   single    0.970  0.020  1.090
 GRA  C16  H16A  single    0.970  0.020  1.090
 GRA  C16  H16B  single    0.970  0.020  1.090
 GRA  C14  H14   single    0.970  0.020  1.090
 GRA  O1   HO1   single    0.850  0.020  0.980
 GRA  N1   HN1   single    0.860  0.020  1.020
 GRA  C2   H2    single    0.970  0.020  1.090
 GRA  C2   H2B   single    0.970  0.020  1.090
 GRA  C3   H3    single    0.970  0.020  1.090
 GRA  C3   H3A   single    0.970  0.020  1.090
 GRA  N2   HN2   single    0.860  0.020  1.020
 GRA  C5   H5    single    0.970  0.020  1.090
 GRA  C5   H5A   single    0.970  0.020  1.090
 GRA  C6   H6    single    0.970  0.020  1.090
 GRA  C6   H6A   single    0.970  0.020  1.090
 GRA  C8   H8    single    0.970  0.020  1.090
 GRA  C8   H8B   single    0.970  0.020  1.090
 GRA  C9   H9    single    0.970  0.020  1.090
 GRA  C9   H9A   single    0.970  0.020  1.090
 GRA  C10  H10   single    0.970  0.020  1.090
 GRA  C10  H10A  single    0.970  0.020  1.090
 GRA  O6   HO6   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
 GRA  HO9A  O9A  P3X   114.59  3.000
 GRA  O3X   P3X  O8A   109.97  3.000
 GRA  O3X   P3X  O7A   101.41  3.000
 GRA  O8A   P3X  O7A   118.10  3.000
 GRA  O3X   P3X  O9A   107.87  3.000
 GRA  O8A   P3X  O9A   116.75  3.000
 GRA  O7A   P3X  O9A   101.23  3.000
 GRA  HO7A  O7A  P3X   115.44  3.000
 GRA  C3X   O3X  P3X   125.89  3.000
 GRA  H3X   C3X  C4X   109.74  3.000
 GRA  H3X   C3X  C2X   109.50  3.000
 GRA  C4X   C3X  C2X   102.80  3.000
 GRA  H3X   C3X  O3X   111.20  3.000
 GRA  C4X   C3X  O3X   108.68  3.000
 GRA  C2X   C3X  O3X   114.55  3.000
 GRA  H2X   C2X  C1X   110.68  3.000
 GRA  H2X   C2X  O2X   106.00  3.000
 GRA  C1X   C2X  O2X   112.87  3.000
 GRA  H2X   C2X  C3X   111.56  3.000
 GRA  C1X   C2X  C3X   102.13  3.000
 GRA  O2X   C2X  C3X   113.73  3.000
 GRA  HO2X  O2X  C2X   110.91  3.000
 GRA  H4X   C4X  C5X   109.76  3.000
 GRA  H4X   C4X  O4X   110.94  3.000
 GRA  C5X   C4X  O4X   109.74  3.000
 GRA  H4X   C4X  C3X   109.44  3.000
 GRA  C5X   C4X  C3X   112.66  3.000
 GRA  O4X   C4X  C3X   104.21  3.000
 GRA  C1X   O4X  C4X   110.54  3.000
 GRA  H1X   C1X  N9A   105.83  3.000
 GRA  H1X   C1X  O4X   111.60  3.000
 GRA  N9A   C1X  O4X   107.74  3.000
 GRA  H1X   C1X  C2X   109.22  3.000
 GRA  N9A   C1X  C2X   114.96  3.000
 GRA  O4X   C1X  C2X   107.55  3.000
 GRA  C8A   N9A  C4A   106.25  3.000
 GRA  C8A   N9A  C1X   127.32  3.000
 GRA  C4A   N9A  C1X   126.21  3.000
 GRA  C5A   C4A  N3A   126.72  3.000
 GRA  C5A   C4A  N9A   105.31  3.000
 GRA  N3A   C4A  N9A   127.96  3.000
 GRA  C2A   N3A  C4A   111.65  3.000
 GRA  H2A   C2A  N1A   115.53  3.000
 GRA  H2A   C2A  N3A   116.17  3.000
 GRA  N1A   C2A  N3A   128.30  3.000
 GRA  H8A   C8A  N7A   124.69  3.000
 GRA  H8A   C8A  N9A   122.04  3.000
 GRA  N7A   C8A  N9A   113.26  3.000
 GRA  C5A   N7A  C8A   104.76  3.000
 GRA  C6A   C5A  N7A   133.41  3.000
 GRA  C6A   C5A  C4A   116.18  3.000
 GRA  N7A   C5A  C4A   110.41  3.000
 GRA  N1A   C6A  N6A   118.65  3.000
 GRA  N1A   C6A  C5A   117.66  3.000
 GRA  N6A   C6A  C5A   123.68  3.000
 GRA  HN6B  N6A  HN6A  116.56  3.000
 GRA  HN6B  N6A  C6A   122.15  3.000
 GRA  HN6A  N6A  C6A   118.70  3.000
 GRA  C6A   N1A  C2A   119.47  3.000
 GRA  H5XA  C5X  H5X   108.67  3.000
 GRA  H5XA  C5X  O5X   110.69  3.000
 GRA  H5X   C5X  O5X   110.31  3.000
 GRA  H5XA  C5X  C4X   109.83  3.000
 GRA  H5X   C5X  C4X   109.26  3.000
 GRA  O5X   C5X  C4X   108.06  3.000
 GRA  P1A   O5X  C5X   123.54  3.000
 GRA  O3A   P1A  O2A   117.08  3.000
 GRA  O3A   P1A  O1A    99.43  3.000
 GRA  O2A   P1A  O1A   117.28  3.000
 GRA  O3A   P1A  O5X   101.26  3.000
 GRA  O2A   P1A  O5X   112.00  3.000
 GRA  O1A   P1A  O5X   107.95  3.000
 GRA  HO1A  O1A  P1A   114.86  3.000
 GRA  P2A   O3A  P1A   127.68  3.000
 GRA  O6A   P2A  O5A   119.79  3.000
 GRA  O6A   P2A  O4A    98.75  3.000
 GRA  O5A   P2A  O4A   117.86  3.000
 GRA  O6A   P2A  O3A   100.87  3.000
 GRA  O5A   P2A  O3A   112.33  3.000
 GRA  O4A   P2A  O3A   104.74  3.000
 GRA  HO4A  O4A  P2A   114.36  3.000
 GRA  C13   O6A  P2A   123.07  3.000
 GRA  H13A  C13  H13   107.76  3.000
 GRA  H13A  C13  C12   109.02  3.000
 GRA  H13   C13  C12   111.66  3.000
 GRA  H13A  C13  O6A   109.15  3.000
 GRA  H13   C13  O6A   110.28  3.000
 GRA  C12   C13  O6A   108.92  3.000
 GRA  C14   C12  C16   111.41  3.000
 GRA  C14   C12  C15   111.57  3.000
 GRA  C16   C12  C15   109.54  3.000
 GRA  C14   C12  C13   109.29  3.000
 GRA  C16   C12  C13   106.40  3.000
 GRA  C15   C12  C13   108.46  3.000
 GRA  H15B  C15  H15A  107.84  3.000
 GRA  H15B  C15  H15   107.69  3.000
 GRA  H15A  C15  H15   107.62  3.000
 GRA  H15B  C15  C12   112.02  3.000
 GRA  H15A  C15  C12   109.66  3.000
 GRA  H15   C15  C12   111.83  3.000
 GRA  H16B  C16  H16A  106.94  3.000
 GRA  H16B  C16  H16   107.22  3.000
 GRA  H16A  C16  H16   107.92  3.000
 GRA  H16B  C16  C12   110.43  3.000
 GRA  H16A  C16  C12   112.84  3.000
 GRA  H16   C16  C12   111.23  3.000
 GRA  H14   C14  C1    105.71  3.000
 GRA  H14   C14  O1    105.48  3.000
 GRA  C1    C14  O1    112.62  3.000
 GRA  H14   C14  C12   108.01  3.000
 GRA  C1    C14  C12   111.61  3.000
 GRA  O1    C14  C12   112.85  3.000
 GRA  HO1   O1   C14   110.69  3.000
 GRA  N1    C1   O2    122.81  3.000
 GRA  N1    C1   C14   116.28  3.000
 GRA  O2    C1   C14   120.90  3.000
 GRA  HN1   N1   C2    115.56  3.000
 GRA  HN1   N1   C1    121.31  3.000
 GRA  C2    N1   C1    123.13  3.000
 GRA  H2B   C2   H2    107.29  3.000
 GRA  H2B   C2   C3    110.36  3.000
 GRA  H2    C2   C3    110.38  3.000
 GRA  H2B   C2   N1    107.10  3.000
 GRA  H2    C2   N1    110.16  3.000
 GRA  C3    C2   N1    111.41  3.000
 GRA  H3A   C3   H3    106.67  3.000
 GRA  H3A   C3   C4    111.86  3.000
 GRA  H3    C3   C4    106.59  3.000
 GRA  H3A   C3   C2    110.14  3.000
 GRA  H3    C3   C2    108.94  3.000
 GRA  C4    C3   C2    112.37  3.000
 GRA  N2    C4   O3    122.65  3.000
 GRA  N2    C4   C3    115.85  3.000
 GRA  O3    C4   C3    121.48  3.000
 GRA  HN2   N2   C5    117.70  3.000
 GRA  HN2   N2   C4    118.68  3.000
 GRA  C5    N2   C4    123.30  3.000
 GRA  H5A   C5   H5    107.32  3.000
 GRA  H5A   C5   C6    110.00  3.000
 GRA  H5    C5   C6    110.22  3.000
 GRA  H5A   C5   N2    109.60  3.000
 GRA  H5    C5   N2    107.75  3.000
 GRA  C6    C5   N2    111.82  3.000
 GRA  H6A   C6   H6    107.84  3.000
 GRA  H6A   C6   S1    109.19  3.000
 GRA  H6    C6   S1    105.48  3.000
 GRA  H6A   C6   C5    111.50  3.000
 GRA  H6    C6   C5    110.64  3.000
 GRA  S1    C6   C5    111.93  3.000
 GRA  C7    S1   C6    102.12  3.000
 GRA  C8    C7   O4    124.82  3.000
 GRA  C8    C7   S1    112.21  3.000
 GRA  O4    C7   S1    122.96  3.000
 GRA  H8B   C8   H8    105.64  3.000
 GRA  H8B   C8   C9    110.58  3.000
 GRA  H8    C8   C9    110.87  3.000
 GRA  H8B   C8   C7    109.23  3.000
 GRA  H8    C8   C7    106.30  3.000
 GRA  C9    C8   C7    113.82  3.000
 GRA  H9A   C9   H9    106.57  3.000
 GRA  H9A   C9   C10   109.98  3.000
 GRA  H9    C9   C10   108.06  3.000
 GRA  H9A   C9   C8    110.52  3.000
 GRA  H9    C9   C8    109.31  3.000
 GRA  C10   C9   C8    112.21  3.000
 GRA  H10A  C10  H10   105.41  3.000
 GRA  H10A  C10  C11   106.91  3.000
 GRA  H10   C10  C11   109.27  3.000
 GRA  H10A  C10  C9    109.66  3.000
 GRA  H10   C10  C9    111.04  3.000
 GRA  C11   C10  C9    114.10  3.000
 GRA  O6    C11  O5    123.03  3.000
 GRA  O6    C11  C10   111.79  3.000
 GRA  O5    C11  C10   125.13  3.000
 GRA  HO6   O6   C11   109.91  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
 GRA  CONST_01  C2A   N3A  C4A  N9A   180.00   0.0  0
 GRA  CONST_02  N7A   C5A  C4A  N9A     0.00   0.0  0
 GRA  CONST_03  C6A   C5A  C4A  N9A   180.00   0.0  0
 GRA  CONST_04  C5A   N7A  C8A  N9A     0.00   0.0  0
 GRA  CONST_05  N7A   C8A  N9A  C4A     0.00   0.0  0
 GRA  CONST_06  N1A   C2A  N3A  C4A     0.00   0.0  0
 GRA  CONST_07  C8A   N7A  C5A  C4A     0.00   0.0  0
 GRA  CONST_08  N1A   C6A  C5A  C4A     0.00   0.0  0
 GRA  CONST_09  C8A   N9A  C4A  N3A   180.00   0.0  0
 GRA  CONST_10  N7A   C5A  C4A  N3A   180.00   0.0  0
 GRA  CONST_11  C6A   C5A  C4A  N3A     0.00   0.0  0
 GRA  CONST_12  C6A   N1A  C2A  N3A     0.00   0.0  0
 GRA  CONST_13  C5A   C4A  N3A  C2A     0.00   0.0  0
 GRA  CONST_14  C5A   C6A  N1A  C2A     0.00   0.0  0
 GRA  CONST_15  C5A   C4A  N9A  C8A     0.00   0.0  0
 GRA  CONST_16  C6A   C5A  N7A  C8A   180.00   0.0  0
 GRA  CONST_17  N1A   C6A  C5A  N7A   180.00   0.0  0
 GRA  CONST_18  N3A   C4A  N9A  C1X     0.00   0.0  0
 GRA  CONST_19  C5A   C4A  N9A  C1X   180.00   0.0  0
 GRA  CONST_20  N7A   C8A  N9A  C1X   180.00   0.0  0
 GRA  CONST_21  N6A   C6A  C5A  C4A   180.00   0.0  0
 GRA  CONST_22  N6A   C6A  N1A  C2A   180.00   0.0  0
 GRA  CONST_23  N6A   C6A  C5A  N7A     0.00   0.0  0
 GRA  CONST_24  H8A   C8A  N9A  C1X     0.00   0.0  0
 GRA  CONST_25  H8A   C8A  N9A  C4A   180.00   0.0  0
 GRA  CONST_26  H2A   C2A  N3A  C4A   180.00   0.0  0
 GRA  CONST_27  H8A   C8A  N7A  C5A   180.00   0.0  0
 GRA  CONST_28  H2A   C2A  N1A  C6A   180.00   0.0  0
 GRA  CONST_29  HN6A  N6A  C6A  C5A   180.00   0.0  0
 GRA  CONST_30  HN6B  N6A  C6A  C5A     0.00   0.0  0
 GRA  CONST_31  HN6A  N6A  C6A  N1A     0.00   0.0  0
 GRA  CONST_32  HN6B  N6A  C6A  N1A   180.00   0.0  0
 GRA  CONST_33  C2    N1   C1   C14   180.00   0.0  0
 GRA  CONST_34  C2    N1   C1   O2      0.00   0.0  0
 GRA  CONST_35  C5    N2   C4   C3    180.00   0.0  0
 GRA  CONST_36  C5    N2   C4   O3      0.00   0.0  0
 GRA  CONST_37  HN1   N1   C1   C14     0.00   0.0  0
 GRA  CONST_38  HN1   N1   C1   O2    180.00   0.0  0
 GRA  CONST_39  HN2   N2   C4   C3      0.00   0.0  0
 GRA  CONST_40  HN2   N2   C4   O3    180.00   0.0  0
 GRA  CONST_41  HO6   O6   C11  C10   180.00   0.0  0
 GRA  CONST_42  HO6   O6   C11  O5      0.00   0.0  0
 GRA  Var_01    C3X   O3X  P3X  O9A   -48.31  30.0  3
 GRA  Var_02    C3X   O3X  P3X  O7A    57.57  30.0  3
 GRA  Var_03    C3X   O3X  P3X  O8A  -176.66  30.0  3
 GRA  Var_04    P1A   O5X  C5X  C4X  -176.92  30.0  3
 GRA  Var_05    O1A   P1A  O5X  C5X   -50.29  30.0  3
 GRA  Var_06    O2A   P1A  O5X  C5X   179.13  30.0  3
 GRA  Var_07    O3A   P1A  O5X  C5X    53.60  30.0  3
 GRA  Var_08    P2A   O3A  P1A  O5X  -165.99  30.0  3
 GRA  Var_09    O4A   P2A  O3A  P1A    90.52  30.0  3
 GRA  Var_10    O5A   P2A  O3A  P1A   -38.57  30.0  3
 GRA  Var_11    O6A   P2A  O3A  P1A  -167.32  30.0  3
 GRA  Var_12    P2A   O3A  P1A  O1A   -55.40  30.0  3
 GRA  Var_13    P2A   O3A  P1A  O2A    71.96  30.0  3
 GRA  Var_14    C13   O6A  P2A  O3A    63.20  30.0  3
 GRA  Var_15    C12   C13  O6A  P2A  -168.67  30.0  3
 GRA  Var_16    C13   O6A  P2A  O4A   170.16  30.0  3
 GRA  Var_17    C13   O6A  P2A  O5A   -60.57  30.0  3
 GRA  Var_18    C15   C12  C13  O6A   -64.44  30.0  3
 GRA  Var_19    C16   C12  C13  O6A   177.80  30.0  3
 GRA  Var_20    C14   C12  C13  O6A    57.40  30.0  3
 GRA  Var_21    C3    C2   N1   C1    -84.14  30.0  3
 GRA  Var_22    C4    C3   C2   N1   -164.82  30.0  3
 GRA  Var_23    O3    C4   C3   C2     43.95  30.0  3
 GRA  Var_24    N2    C4   C3   C2   -137.69  30.0  3
 GRA  Var_25    C6    C5   N2   C4     82.05  30.0  3
 GRA  Var_26    S1    C6   C5   N2   -178.10  30.0  3
 GRA  Var_27    C7    S1   C6   C5    -79.46  30.0  3
 GRA  Var_28    O4    C7   S1   C6     -6.66  30.0  3
 GRA  Var_29    C8    C7   S1   C6    171.91  30.0  3
 GRA  Var_30    C9    C8   C7   S1    161.88  30.0  3
 GRA  Var_31    C10   C9   C8   C7   -178.43  30.0  3
 GRA  Var_32    C9    C8   C7   O4    -19.58  30.0  3
 GRA  Var_33    C11   C10  C9   C8    -70.59  30.0  3
 GRA  Var_34    O5    C11  C10  C9    -13.25  30.0  3
 GRA  Var_35    O6    C11  C10  C9    169.18  30.0  3
 GRA  Var_36    H5X   C5X  O5X  P1A    63.70  30.0  1
 GRA  Var_37    H5XA  C5X  O5X  P1A   -56.62  30.0  1
 GRA  Var_38    H13   C13  O6A  P2A   -45.81  30.0  3
 GRA  Var_39    H13A  C13  O6A  P2A    72.39  30.0  3
 GRA  Var_40    H15   C15  C12  C13  -169.74  30.0  3
 GRA  Var_41    H15A  C15  C12  C13   -50.44  30.0  3
 GRA  Var_42    H15B  C15  C12  C13    69.27  30.0  3
 GRA  Var_43    H16   C16  C12  C13   175.13  30.0  3
 GRA  Var_44    H16A  C16  C12  C13   -63.42  30.0  3
 GRA  Var_45    H16B  C16  C12  C13    56.20  30.0  3
 GRA  Var_46    H13   C13  C12  C15   173.53  30.0  1
 GRA  Var_47    H13A  C13  C12  C15    54.58  30.0  1
 GRA  Var_48    H16   C16  C12  C15    58.08  30.0  3
 GRA  Var_49    H16A  C16  C12  C15   179.53  30.0  3
 GRA  Var_50    H16B  C16  C12  C15   -60.84  30.0  3
 GRA  Var_51    H13   C13  C12  C16    55.77  30.0  1
 GRA  Var_52    H13A  C13  C12  C16   -63.19  30.0  1
 GRA  Var_53    H15   C15  C12  C16   -53.99  30.0  3
 GRA  Var_54    H15A  C15  C12  C16    65.31  30.0  3
 GRA  Var_55    H15B  C15  C12  C16  -174.99  30.0  3
 GRA  Var_56    H13   C13  C12  C14   -64.64  30.0  1
 GRA  Var_57    H13A  C13  C12  C14   176.41  30.0  1
 GRA  Var_58    H15   C15  C12  C14    69.84  30.0  3
 GRA  Var_59    H15A  C15  C12  C14  -170.86  30.0  3
 GRA  Var_60    H15B  C15  C12  C14   -51.16  30.0  3
 GRA  Var_61    H16   C16  C12  C14   -65.84  30.0  3
 GRA  Var_62    H16A  C16  C12  C14    55.60  30.0  3
 GRA  Var_63    H16B  C16  C12  C14   175.23  30.0  3
 GRA  Var_64    H2    C2   N1   C1     38.70  30.0  3
 GRA  Var_65    H2B   C2   N1   C1    155.08  30.0  3
 GRA  Var_66    H3    C3   C2   N1    -46.94  30.0  3
 GRA  Var_67    H3A   C3   C2   N1     69.73  30.0  3
 GRA  Var_68    HN1   N1   C2   C3     95.01  30.0  1
 GRA  Var_69    H2    C2   C3   C4     72.45  30.0  2
 GRA  Var_70    H2B   C2   C3   C4    -45.97  30.0  2
 GRA  Var_71    H5    C5   N2   C4   -156.68  30.0  3
 GRA  Var_72    H5A   C5   N2   C4    -40.20  30.0  3
 GRA  Var_73    H3    C3   C4   O3    -75.31  30.0  1
 GRA  Var_74    H3A   C3   C4   O3    168.45  30.0  1
 GRA  Var_75    H3    C3   C4   N2    103.04  30.0  1
 GRA  Var_76    H3A   C3   C4   N2    -13.19  30.0  1
 GRA  Var_77    H6    C6   C5   N2    -60.76  30.0  3
 GRA  Var_78    H6A   C6   C5   N2     59.25  30.0  3
 GRA  Var_79    HN2   N2   C5   C6    -91.40  30.0  1
 GRA  Var_80    H5    C5   C6   S1     62.06  30.0  1
 GRA  Var_81    H5A   C5   C6   S1    -56.08  30.0  1
 GRA  Var_82    H8    C8   C7   S1    -75.79  30.0  3
 GRA  Var_83    H8B   C8   C7   S1     37.76  30.0  3
 GRA  Var_84    H6    C6   S1   C7    160.15  30.0  2
 GRA  Var_85    H6A   C6   S1   C7     44.49  30.0  2
 GRA  Var_86    H9    C9   C8   C7    -58.57  30.0  3
 GRA  Var_87    H9A   C9   C8   C7     58.42  30.0  3
 GRA  Var_88    H8    C8   C7   O4    102.75  30.0  3
 GRA  Var_89    H8B   C8   C7   O4   -143.70  30.0  3
 GRA  Var_90    H10   C10  C9   C8     53.43  30.0  3
 GRA  Var_91    H10A  C10  C9   C8    169.52  30.0  3
 GRA  Var_92    H8    C8   C9   C10    61.79  30.0  1
 GRA  Var_93    H8B   C8   C9   C10   -55.04  30.0  1
 GRA  Var_94    H9    C9   C10  C11   168.82  30.0  2
 GRA  Var_95    H9A   C9   C10  C11    52.86  30.0  2
 GRA  Var_96    H10   C10  C11  O5   -138.22  30.0  2
 GRA  Var_97    H10A  C10  C11  O5    108.16  30.0  2
 GRA  Var_98    H10   C10  C11  O6     44.21  30.0  2
 GRA  Var_99    H10A  C10  C11  O6    -69.41  30.0  2

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
 GRA  chir_01  C3X  O3X  C2X  C4X  negativ
 GRA  chir_02  C2X  O2X  C1X  C3X  negativ
 GRA  chir_03  C4X  O4X  C3X  C5X  negativ
 GRA  chir_04  C1X  O4X  N9A  C2X  negativ
 GRA  chir_07  C14  C12  O1   C1   negativ
 GRA  chir_08  P1A  O1A  O2A  O3A  both
 GRA  chir_09  P2A  O4A  O5A  O6A  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
 GRA  plan-1  S1    0.020
 GRA  plan-1  C7    0.020
 GRA  plan-1  O4    0.020
 GRA  plan-1  C8    0.020
 GRA  plan-2  C1X   0.020
 GRA  plan-2  N9A   0.020
 GRA  plan-2  C4A   0.020
 GRA  plan-2  N3A   0.020
 GRA  plan-2  C2A   0.020
 GRA  plan-2  C8A   0.020
 GRA  plan-2  N7A   0.020
 GRA  plan-2  C5A   0.020
 GRA  plan-2  C6A   0.020
 GRA  plan-2  N6A   0.020
 GRA  plan-2  N1A   0.020
 GRA  plan-2  H2A   0.020
 GRA  plan-2  H8A   0.020
 GRA  plan-3  C3    0.020
 GRA  plan-3  C4    0.020
 GRA  plan-3  O3    0.020
 GRA  plan-3  N2    0.020
 GRA  plan-3  C5    0.020
 GRA  plan-3  HN2   0.020
 GRA  plan-4  C6A   0.020
 GRA  plan-4  N6A   0.020
 GRA  plan-4  HN6A  0.020
 GRA  plan-4  HN6B  0.020
 GRA  plan-5  C14   0.020
 GRA  plan-5  C1    0.020
 GRA  plan-5  O2    0.020
 GRA  plan-5  N1    0.020
 GRA  plan-5  C2    0.020
 GRA  plan-5  HN1   0.020
 GRA  plan-6  C10   0.020
 GRA  plan-6  C11   0.020
 GRA  plan-6  O5    0.020
 GRA  plan-6  O6    0.020
 GRA  plan-6  HO6   0.020

