data_3L2
#

_chem_comp.id                                   3L2
_chem_comp.name                                 "(4S,5R,10E,12Z,16R,16aS,17S,18R,19aR,23aR)-4-hydroxy-5,16a,21-trimethyl-4,5,6,7,16,16a,22,23-octahydro-3H,18H,19aH-spiro[16,18-methano[1,6,12]trioxacyclooctadecino[3,4-d]chromene-17,2'-oxirane]-3,9,14-trione"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C27 H34 O9"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        "Verrucarin A"
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2014-09-11
_chem_comp.pdbx_modified_date                   2021-03-01
_chem_comp.pdbx_ambiguous_flag                  N
_chem_comp.pdbx_release_status                  REL
_chem_comp.pdbx_replaced_by                     ?
_chem_comp.pdbx_replaces                        ?
_chem_comp.formula_weight                       502.553
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    3L2
_chem_comp.pdbx_model_coordinates_details       ?
_chem_comp.pdbx_model_coordinates_missing_flag  N
_chem_comp.pdbx_ideal_coordinates_details       Corina
_chem_comp.pdbx_ideal_coordinates_missing_flag  N
_chem_comp.pdbx_model_coordinates_db_code       4U50
_chem_comp.pdbx_subcomponent_list               ?
_chem_comp.pdbx_processing_site                 EBI
#   #
loop_
_chem_comp_atom.comp_id
_chem_comp_atom.atom_id
_chem_comp_atom.alt_atom_id
_chem_comp_atom.type_symbol
_chem_comp_atom.charge
_chem_comp_atom.pdbx_align
_chem_comp_atom.pdbx_aromatic_flag
_chem_comp_atom.pdbx_leaving_atom_flag
_chem_comp_atom.pdbx_stereo_config
_chem_comp_atom.model_Cartn_x
_chem_comp_atom.model_Cartn_y
_chem_comp_atom.model_Cartn_z
_chem_comp_atom.pdbx_model_Cartn_x_ideal
_chem_comp_atom.pdbx_model_Cartn_y_ideal
_chem_comp_atom.pdbx_model_Cartn_z_ideal
_chem_comp_atom.pdbx_component_atom_id
_chem_comp_atom.pdbx_component_comp_id
_chem_comp_atom.pdbx_ordinal
3L2  O    O1   O  0  1  N  N  N  29.183  9.314  66.648  -4.287   0.181  -0.079  O    3L2   1  
3L2  C1   C1   C  0  1  N  N  R  27.879  6.819  65.801  -2.657   3.065   0.201  C1   3L2   2  
3L2  O6   O2   O  0  1  N  N  N  26.952  3.736  64.728   0.261   3.206   1.535  O6   3L2   3  
3L2  C23  C2   C  0  1  N  N  N  27.214  4.810  64.310  -0.209   2.745   0.523  C23  3L2   4  
3L2  C24  C3   C  0  1  N  N  S  26.814  6.097  65.004  -1.260   3.517  -0.230  C24  3L2   5  
3L2  O7   O3   O  0  1  N  N  N  25.635  5.812  65.760  -1.090   3.310  -1.634  O7   3L2   6  
3L2  C    C4   C  0  1  N  N  N  28.510  5.891  66.838  -2.567   2.251   1.491  C    3L2   7  
3L2  O5   O4   O  0  1  N  N  N  27.797  5.006  63.110   0.198   1.547   0.077  O5   3L2   8  
3L2  C22  C5   C  0  1  N  N  N  27.930  3.845  62.264   0.875   0.687   1.026  C22  3L2   9  
3L2  C15  C6   C  0  1  N  N  R  28.445  4.215  60.865   2.172   0.120   0.457  C15  3L2  10  
3L2  C20  C7   C  0  1  N  N  R  28.919  2.851  60.295   2.330   0.513  -1.013  C20  3L2  11  
3L2  C19  C8   C  0  1  N  N  N  27.794  1.961  59.851   2.626   1.986  -1.122  C19  3L2  12  
3L2  C18  C9   C  0  1  N  N  N  26.530  2.341  59.766   3.063   2.705  -0.143  C18  3L2  13  
3L2  C21  C10  C  0  1  N  N  N  25.413  1.378  59.470   3.319   4.166  -0.406  C21  3L2  14  
3L2  C17  C11  C  0  1  N  N  N  26.139  3.774  59.965   3.339   2.188   1.233  C17  3L2  15  
3L2  C16  C12  C  0  1  N  N  N  27.315  4.738  59.943   3.365   0.659   1.243  C16  3L2  16  
3L2  O4   O5   O  0  1  N  N  N  29.838  2.943  59.182   3.381  -0.210  -1.651  O4   3L2  17  
3L2  C12  C13  C  0  1  N  N  R  30.894  3.897  59.344   3.363  -1.635  -1.504  C12  3L2  18  
3L2  C11  C14  C  0  1  N  N  N  31.631  3.716  60.687   1.926  -2.132  -1.803  C11  3L2  19  
3L2  C14  C15  C  0  1  N  N  S  29.690  5.213  60.935   2.147  -1.424   0.552  C14  3L2  20  
3L2  C25  C16  C  0  1  N  N  N  29.306  6.614  61.409   1.849  -1.952   1.957  C25  3L2  21  
3L2  C13  C17  C  0  1  N  N  S  30.253  5.278  59.536   3.495  -1.926   0.004  C13  3L2  22  
3L2  O8   O6   O  0  1  N  N  N  31.177  6.404  59.239   4.118  -3.098   0.495  O8   3L2  23  
3L2  C26  C18  C  0  1  N  N  N  29.950  6.255  58.491   4.800  -1.867   0.758  C26  3L2  24  
3L2  C10  C19  C  0  1  N  N  R  30.901  4.609  61.731   1.123  -1.895  -0.515  C10  3L2  25  
3L2  O3   O7   O  0  1  N  N  N  31.871  5.657  62.053   0.421  -3.092  -0.092  O3   3L2  26  
3L2  C9   C20  C  0  1  N  N  N  31.910  6.146  63.305  -0.914  -3.057  -0.279  C9   3L2  27  
3L2  O2   O8   O  0  1  N  N  N  31.357  5.612  64.248  -1.363  -2.137  -0.936  O2   3L2  28  
3L2  C8   C21  C  0  1  N  N  N  32.753  7.333  63.375  -1.827  -4.087   0.206  C8   3L2  29  
3L2  C7   C22  C  0  1  N  N  N  33.008  8.238  64.336  -3.134  -3.800   0.423  C7   3L2  30  
3L2  C6   C23  C  0  1  N  N  N  32.339  8.325  65.583  -3.618  -2.437   0.262  C6   3L2  31  
3L2  C5   C24  C  0  1  N  N  N  31.097  8.785  65.709  -4.932  -2.123   0.262  C5   3L2  32  
3L2  C4   C25  C  0  1  N  N  N  30.396  8.904  66.986  -5.290  -0.703   0.067  C4   3L2  33  
3L2  O1   O9   O  0  1  N  N  N  30.845  8.642  68.078  -6.451  -0.359   0.037  O1   3L2  34  
3L2  C3   C26  C  0  1  N  N  N  28.124  8.790  67.462  -4.583   1.559  -0.405  C3   3L2  35  
3L2  C2   C27  C  0  1  N  N  N  27.252  8.021  66.503  -3.306   2.240  -0.906  C2   3L2  36  
3L2  H1   H1   H  0  1  N  N  N  28.663  7.174  65.116  -3.269   3.956   0.388  H1   3L2  37  
3L2  H2   H2   H  0  1  N  N  N  26.518  6.790  64.203  -1.142   4.580  -0.005  H2   3L2  38  
3L2  H3   H3   H  0  1  N  N  N  25.491  4.873  65.781  -0.230   3.594  -1.972  H3   3L2  39  
3L2  H4   H4   H  0  1  N  N  N  29.279  6.439  67.402  -1.967   1.358   1.316  H4   3L2  40  
3L2  H5   H5   H  0  1  N  N  N  27.734  5.533  67.530  -2.102   2.855   2.270  H5   3L2  41  
3L2  H6   H6   H  0  1  N  N  N  28.972  5.032  66.329  -3.569   1.959   1.807  H6   3L2  42  
3L2  H7   H7   H  0  1  N  N  N  26.947  3.362  62.165   1.096   1.239   1.939  H7   3L2  43  
3L2  H8   H8   H  0  1  N  N  N  28.638  3.144  62.730   0.195  -0.131   1.275  H8   3L2  44  
3L2  H9   H9   H  0  1  N  N  N  29.437  2.332  61.115   1.393   0.321  -1.543  H9   3L2  45  
3L2  H10  H10  H  0  1  N  N  N  28.033  0.942  59.583   2.465   2.467  -2.076  H10  3L2  46  
3L2  H11  H11  H  0  1  N  N  N  24.456  1.921  59.449   3.080   4.396  -1.444  H11  3L2  47  
3L2  H12  H12  H  0  1  N  N  N  25.587  0.904  58.493   2.694   4.768   0.253  H12  3L2  48  
3L2  H13  H13  H  0  1  N  N  N  25.379  0.605  60.252   4.369   4.390  -0.216  H13  3L2  49  
3L2  H14  H14  H  0  1  N  N  N  25.442  4.058  59.163   4.313   2.558   1.563  H14  3L2  50  
3L2  H15  H15  H  0  1  N  N  N  25.634  3.864  60.938   2.572   2.543   1.915  H15  3L2  51  
3L2  H16  H16  H  0  1  N  N  N  27.695  4.826  58.915   3.327   0.312   2.274  H16  3L2  52  
3L2  H17  H17  H  0  1  N  N  N  26.984  5.725  60.297   4.292   0.321   0.778  H17  3L2  53  
3L2  H18  H18  H  0  1  N  N  N  31.601  3.899  58.501   4.122  -2.147  -2.100  H18  3L2  54  
3L2  H19  H19  H  0  1  N  N  N  31.593  2.662  60.999   1.496  -1.564  -2.628  H19  3L2  55  
3L2  H20  H20  H  0  1  N  N  N  32.680  4.032  60.588   1.940  -3.194  -2.048  H20  3L2  56  
3L2  H21  H21  H  0  1  N  N  N  28.897  6.557  62.429   0.872  -1.592   2.280  H21  3L2  57  
3L2  H22  H22  H  0  1  N  N  N  30.197  7.259  61.407   1.848  -3.042   1.943  H22  3L2  58  
3L2  H23  H23  H  0  1  N  N  N  28.547  7.035  60.733   2.614  -1.598   2.648  H23  3L2  59  
3L2  H24  H24  H  0  1  N  N  N  29.131  6.974  58.637   5.711  -1.659   0.193  H24  3L2  60  
3L2  H25  H25  H  0  1  N  N  N  29.988  5.953  57.434   4.795  -1.497   1.784  H25  3L2  61  
3L2  H26  H26  H  0  1  N  N  N  30.569  4.033  62.607   0.389  -1.096  -0.686  H26  3L2  62  
3L2  H27  H27  H  0  1  N  N  N  33.288  7.527  62.457  -1.467  -5.088   0.396  H27  3L2  63  
3L2  H28  H28  H  0  1  N  N  N  33.788  8.959  64.142  -3.809  -4.593   0.716  H28  3L2  64  
3L2  H29  H29  H  0  1  N  N  N  32.862  8.003  66.472  -2.914  -1.616   0.163  H29  3L2  65  
3L2  H30  H30  H  0  1  N  N  N  30.575  9.089  64.814  -5.690  -2.866   0.402  H30  3L2  66  
3L2  H31  H31  H  0  1  N  N  N  27.557  9.606  67.934  -5.333   1.580  -1.204  H31  3L2  67  
3L2  H32  H32  H  0  1  N  N  N  28.526  8.125  68.241  -4.985   2.080   0.460  H32  3L2  68  
3L2  H33  H33  H  0  1  N  N  N  26.918  8.722  65.724  -3.565   2.893  -1.741  H33  3L2  69  
3L2  H34  H34  H  0  1  N  N  N  26.380  7.657  67.067  -2.610   1.474  -1.253  H34  3L2  70  
#   #
loop_
_chem_comp_bond.comp_id
_chem_comp_bond.atom_id_1
_chem_comp_bond.atom_id_2
_chem_comp_bond.value_order
_chem_comp_bond.pdbx_aromatic_flag
_chem_comp_bond.pdbx_stereo_config
_chem_comp_bond.pdbx_ordinal
3L2  C26  O8   SING  N  N   1  
3L2  C26  C13  SING  N  N   2  
3L2  O4   C12  SING  N  N   3  
3L2  O4   C20  SING  N  N   4  
3L2  O8   C13  SING  N  N   5  
3L2  C12  C13  SING  N  N   6  
3L2  C12  C11  SING  N  N   7  
3L2  C21  C18  SING  N  N   8  
3L2  C13  C14  SING  N  N   9  
3L2  C18  C19  DOUB  N  N  10  
3L2  C18  C17  SING  N  N  11  
3L2  C19  C20  SING  N  N  12  
3L2  C16  C17  SING  N  N  13  
3L2  C16  C15  SING  N  N  14  
3L2  C20  C15  SING  N  N  15  
3L2  C11  C10  SING  N  N  16  
3L2  C15  C14  SING  N  N  17  
3L2  C15  C22  SING  N  N  18  
3L2  C14  C25  SING  N  N  19  
3L2  C14  C10  SING  N  N  20  
3L2  C10  O3   SING  N  N  21  
3L2  O3   C9   SING  N  N  22  
3L2  C22  O5   SING  N  N  23  
3L2  O5   C23  SING  N  N  24  
3L2  C9   C8   SING  N  N  25  
3L2  C9   O2   DOUB  N  N  26  
3L2  C8   C7   DOUB  N  Z  27  
3L2  C23  O6   DOUB  N  N  28  
3L2  C23  C24  SING  N  N  29  
3L2  C7   C6   SING  N  N  30  
3L2  C24  O7   SING  N  N  31  
3L2  C24  C1   SING  N  N  32  
3L2  C6   C5   DOUB  N  E  33  
3L2  C5   C4   SING  N  N  34  
3L2  C1   C2   SING  N  N  35  
3L2  C1   C    SING  N  N  36  
3L2  C2   C3   SING  N  N  37  
3L2  O    C4   SING  N  N  38  
3L2  O    C3   SING  N  N  39  
3L2  C4   O1   DOUB  N  N  40  
3L2  C1   H1   SING  N  N  41  
3L2  C24  H2   SING  N  N  42  
3L2  O7   H3   SING  N  N  43  
3L2  C    H4   SING  N  N  44  
3L2  C    H5   SING  N  N  45  
3L2  C    H6   SING  N  N  46  
3L2  C22  H7   SING  N  N  47  
3L2  C22  H8   SING  N  N  48  
3L2  C20  H9   SING  N  N  49  
3L2  C19  H10  SING  N  N  50  
3L2  C21  H11  SING  N  N  51  
3L2  C21  H12  SING  N  N  52  
3L2  C21  H13  SING  N  N  53  
3L2  C17  H14  SING  N  N  54  
3L2  C17  H15  SING  N  N  55  
3L2  C16  H16  SING  N  N  56  
3L2  C16  H17  SING  N  N  57  
3L2  C12  H18  SING  N  N  58  
3L2  C11  H19  SING  N  N  59  
3L2  C11  H20  SING  N  N  60  
3L2  C25  H21  SING  N  N  61  
3L2  C25  H22  SING  N  N  62  
3L2  C25  H23  SING  N  N  63  
3L2  C26  H24  SING  N  N  64  
3L2  C26  H25  SING  N  N  65  
3L2  C10  H26  SING  N  N  66  
3L2  C8   H27  SING  N  N  67  
3L2  C7   H28  SING  N  N  68  
3L2  C6   H29  SING  N  N  69  
3L2  C5   H30  SING  N  N  70  
3L2  C3   H31  SING  N  N  71  
3L2  C3   H32  SING  N  N  72  
3L2  C2   H33  SING  N  N  73  
3L2  C2   H34  SING  N  N  74  
#   #
loop_
_pdbx_chem_comp_descriptor.comp_id
_pdbx_chem_comp_descriptor.type
_pdbx_chem_comp_descriptor.program
_pdbx_chem_comp_descriptor.program_version
_pdbx_chem_comp_descriptor.descriptor
3L2  SMILES            ACDLabs               12.01  "O=C1OC5CC4OC2C=C(C)CCC2(COC(=O)C(O)C(C)CCOC(=O)C=CC=C1)C5(C)C34OC3"  
3L2  InChI             InChI                 1.03   "InChI=1S/C27H34O9/c1-16-8-10-26-14-33-24(31)23(30)17(2)9-11-32-21(28)6-4-5-7-22(29)36-18-13-20(35-19(26)12-16)27(15-34-27)25(18,26)3/h4-7,12,17-20,23,30H,8-11,13-15H2,1-3H3/b6-4+,7-5-/t17-,18-,19-,20-,23+,25-,26-,27+/m1/s1"  
3L2  InChIKey          InChI                 1.03   NLUGUZJQJYVUHS-IDXDZYHTSA-N  
3L2  SMILES_CANONICAL  CACTVS                3.385  "C[C@@H]1CCOC(=O)\C=C\C=C/C(=O)O[C@@H]2C[C@H]3O[C@@H]4C=C(C)CC[C@]4(COC(=O)[C@H]1O)[C@]2(C)[C@]35CO5"  
3L2  SMILES            CACTVS                3.385  "C[CH]1CCOC(=O)C=CC=CC(=O)O[CH]2C[CH]3O[CH]4C=C(C)CC[C]4(COC(=O)[CH]1O)[C]2(C)[C]35CO5"  
3L2  SMILES_CANONICAL  "OpenEye OEToolkits"  1.9.2  "C[C@@H]1CCOC(=O)/C=C/C=C\C(=O)O[C@@H]2C[C@@H]3[C@]4([C@]2([C@]5(CCC(=C[C@H]5O3)C)COC(=O)[C@H]1O)C)CO4"  
3L2  SMILES            "OpenEye OEToolkits"  1.9.2  "CC1CCOC(=O)C=CC=CC(=O)OC2CC3C4(C2(C5(CCC(=CC5O3)C)COC(=O)C1O)C)CO4"  
#
_pdbx_chem_comp_identifier.comp_id          3L2
_pdbx_chem_comp_identifier.type             "SYSTEMATIC NAME"
_pdbx_chem_comp_identifier.program          ACDLabs
_pdbx_chem_comp_identifier.program_version  12.01
_pdbx_chem_comp_identifier.identifier       "(4S,5R,10E,12Z,16R,16aS,17S,18R,19aR,23aR)-4-hydroxy-5,16a,21-trimethyl-4,5,6,7,16,16a,22,23-octahydro-3H,18H,19aH-spiro[16,18-methano[1,6,12]trioxacyclooctadecino[3,4-d]chromene-17,2'-oxirane]-3,9,14-trione"
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
3L2  "Create component"  2014-09-11  EBI   
3L2  "Initial release"   2014-10-22  RCSB  
3L2  "Modify synonyms"   2021-03-01  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     3L2
_pdbx_chem_comp_synonyms.name        "Verrucarin A"
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
