data_GEF
#

_chem_comp.id                                   GEF
_chem_comp.name                                 "4-[(3R,3aS,6R,6aS)-6-(3-methoxy-4-oxidanyl-phenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxy-phenol"
_chem_comp.type                                 non-polymer
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C20 H22 O6"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        "(-)-pinoresinol"
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2020-08-22
_chem_comp.pdbx_modified_date                   2021-06-04
_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                       358.385
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    GEF
_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       7CS5
_chem_comp.pdbx_subcomponent_list               ?
_chem_comp.pdbx_processing_site                 PDBJ
#   #
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
GEF  CAV  C1   C  0  1  N  N  N  -60.347  71.140   4.666  -6.187   0.993   1.803  CAV  GEF   1  
GEF  OAU  O1   O  0  1  N  N  N  -59.953  70.599   3.439  -6.198  -0.161   0.959  OAU  GEF   2  
GEF  CAQ  C2   C  0  1  Y  N  N  -59.254  71.200   2.443  -5.093  -0.379   0.197  CAQ  GEF   3  
GEF  CAP  C3   C  0  1  Y  N  N  -59.097  70.301   1.481  -4.022   0.498   0.260  CAP  GEF   4  
GEF  CAR  C4   C  0  1  Y  N  N  -58.727  72.507   2.336  -5.033  -1.486  -0.644  CAR  GEF   5  
GEF  OAZ  O2   O  0  1  N  N  N  -58.898  73.456   3.336  -6.079  -2.352  -0.706  OAZ  GEF   6  
GEF  CAS  C5   C  0  1  Y  N  N  -58.034  72.783   1.131  -3.905  -1.704  -1.418  CAS  GEF   7  
GEF  CAT  C6   C  0  1  Y  N  N  -57.854  71.831   0.108  -2.842  -0.822  -1.355  CAT  GEF   8  
GEF  CAO  C7   C  0  1  Y  N  N  -58.465  70.570   0.336  -2.899   0.275  -0.515  CAO  GEF   9  
GEF  CAN  C8   C  0  1  N  N  R  -58.516  69.320  -0.426  -1.735   1.230  -0.445  CAN  GEF  10  
GEF  OAM  O3   O  0  1  N  N  N  -57.440  68.308  -0.279  -1.175   1.414  -1.755  OAM  GEF  11  
GEF  CAL  C9   C  0  1  N  N  N  -56.517  68.864  -0.684   0.241   1.624  -1.581  CAL  GEF  12  
GEF  CAK  C10  C  0  1  N  N  S  -57.293  68.885  -1.988   0.633   0.623  -0.468  CAK  GEF  13  
GEF  CAJ  C11  C  0  1  N  N  S  -58.498  69.915  -1.835  -0.629   0.641   0.449  CAJ  GEF  14  
GEF  CAH  C12  C  0  1  N  N  N  -58.518  69.283  -3.211  -0.241   1.691   1.517  CAH  GEF  15  
GEF  OAI  O4   O  0  1  N  N  N  -57.480  68.345  -3.751   1.176   1.493   1.700  OAI  GEF  16  
GEF  CAG  C13  C  0  1  N  N  R  -57.734  67.479  -2.637   1.737   1.253   0.399  CAG  GEF  17  
GEF  CAD  C14  C  0  1  Y  N  N  -56.888  66.465  -3.026   2.903   0.305   0.511  CAD  GEF  18  
GEF  CAE  C15  C  0  1  Y  N  N  -57.453  65.227  -3.332   4.020   0.490  -0.282  CAE  GEF  19  
GEF  CAC  C16  C  0  1  Y  N  N  -55.547  66.635  -3.392   2.856  -0.743   1.411  CAC  GEF  20  
GEF  CAB  C17  C  0  1  Y  N  N  -54.788  65.589  -3.929   3.924  -1.615   1.517  CAB  GEF  21  
GEF  CAA  C18  C  0  1  Y  N  N  -55.362  64.324  -4.196   5.044  -1.439   0.721  CAA  GEF  22  
GEF  OAY  O5   O  0  1  N  N  N  -54.737  63.227  -4.732   6.095  -2.297   0.825  OAY  GEF  23  
GEF  CAF  C19  C  0  1  Y  N  N  -56.714  64.143  -3.909   5.094  -0.380  -0.180  CAF  GEF  24  
GEF  OAW  O6   O  0  1  N  N  N  -57.242  62.889  -4.176   6.194  -0.200  -0.959  OAW  GEF  25  
GEF  CAX  C20  C  0  1  N  N  N  -58.634  62.843  -3.825   6.175   0.908  -1.861  CAX  GEF  26  
GEF  H1   H1   H  0  1  N  N  N  -60.900  70.382   5.241  -5.356   0.921   2.505  H1   GEF  27  
GEF  H2   H2   H  0  1  N  N  N  -59.457  71.452   5.232  -6.070   1.888   1.192  H2   GEF  28  
GEF  H3   H3   H  0  1  N  N  N  -60.994  72.012   4.491  -7.125   1.048   2.354  H3   GEF  29  
GEF  H4   H4   H  0  1  N  N  N  -59.497  69.309   1.630  -4.064   1.356   0.915  H4   GEF  30  
GEF  H5   H5   H  0  1  N  N  N  -58.474  74.267   3.080  -6.738  -2.126  -1.377  H5   GEF  31  
GEF  H6   H6   H  0  1  N  N  N  -57.624  73.772   0.990  -3.855  -2.562  -2.072  H6   GEF  32  
GEF  H7   H7   H  0  1  N  N  N  -57.290  72.046  -0.788  -1.963  -0.993  -1.959  H7   GEF  33  
GEF  H8   H8   H  0  1  N  N  N  -59.490  68.835  -0.265  -2.066   2.188  -0.045  H8   GEF  34  
GEF  H9   H9   H  0  1  N  N  N  -56.325  69.849  -0.234   0.777   1.400  -2.503  H9   GEF  35  
GEF  H10  H10  H  0  1  N  N  N  -55.585  68.280  -0.700   0.440   2.647  -1.262  H10  GEF  36  
GEF  H11  H11  H  0  1  N  N  N  -56.620  69.340  -2.730   0.881  -0.369  -0.847  H11  GEF  37  
GEF  H12  H12  H  0  1  N  N  N  -58.145  70.957  -1.849  -0.883  -0.336   0.861  H12  GEF  38  
GEF  H13  H13  H  0  1  N  N  N  -59.467  68.729  -3.263  -0.442   2.699   1.154  H13  GEF  39  
GEF  H14  H14  H  0  1  N  N  N  -58.546  70.125  -3.918  -0.776   1.506   2.449  H14  GEF  40  
GEF  H15  H15  H  0  1  N  N  N  -58.786  67.221  -2.446   2.063   2.194  -0.043  H15  GEF  41  
GEF  H16  H16  H  0  1  N  N  N  -58.502  65.077  -3.123   4.056   1.312  -0.981  H16  GEF  42  
GEF  H17  H17  H  0  1  N  N  N  -55.085  67.602  -3.256   1.983  -0.882   2.032  H17  GEF  43  
GEF  H18  H18  H  0  1  N  N  N  -53.742  65.751  -4.144   3.884  -2.434   2.221  H18  GEF  44  
GEF  H19  H19  H  0  1  N  N  N  -55.358  62.511  -4.803   6.039  -3.060   0.234  H19  GEF  45  
GEF  H20  H20  H  0  1  N  N  N  -59.035  61.842  -4.043   7.110   0.937  -2.421  H20  GEF  46  
GEF  H21  H21  H  0  1  N  N  N  -58.749  63.058  -2.752   5.340   0.799  -2.554  H21  GEF  47  
GEF  H22  H22  H  0  1  N  N  N  -59.185  63.594  -4.410   6.060   1.834  -1.297  H22  GEF  48  
#   #
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
GEF  CAV  OAU  SING  N  N   1  
GEF  OAU  CAQ  SING  N  N   2  
GEF  CAQ  CAP  DOUB  Y  N   3  
GEF  CAQ  CAR  SING  Y  N   4  
GEF  CAP  CAO  SING  Y  N   5  
GEF  CAR  OAZ  SING  N  N   6  
GEF  CAR  CAS  DOUB  Y  N   7  
GEF  CAS  CAT  SING  Y  N   8  
GEF  CAT  CAO  DOUB  Y  N   9  
GEF  CAO  CAN  SING  N  N  10  
GEF  CAN  OAM  SING  N  N  11  
GEF  CAN  CAJ  SING  N  N  12  
GEF  OAM  CAL  SING  N  N  13  
GEF  CAL  CAK  SING  N  N  14  
GEF  CAK  CAJ  SING  N  N  15  
GEF  CAK  CAG  SING  N  N  16  
GEF  CAJ  CAH  SING  N  N  17  
GEF  CAH  OAI  SING  N  N  18  
GEF  OAI  CAG  SING  N  N  19  
GEF  CAG  CAD  SING  N  N  20  
GEF  CAD  CAE  DOUB  Y  N  21  
GEF  CAD  CAC  SING  Y  N  22  
GEF  CAE  CAF  SING  Y  N  23  
GEF  CAC  CAB  DOUB  Y  N  24  
GEF  CAB  CAA  SING  Y  N  25  
GEF  CAA  OAY  SING  N  N  26  
GEF  CAA  CAF  DOUB  Y  N  27  
GEF  CAF  OAW  SING  N  N  28  
GEF  OAW  CAX  SING  N  N  29  
GEF  CAV  H1   SING  N  N  30  
GEF  CAV  H2   SING  N  N  31  
GEF  CAV  H3   SING  N  N  32  
GEF  CAP  H4   SING  N  N  33  
GEF  OAZ  H5   SING  N  N  34  
GEF  CAS  H6   SING  N  N  35  
GEF  CAT  H7   SING  N  N  36  
GEF  CAN  H8   SING  N  N  37  
GEF  CAL  H9   SING  N  N  38  
GEF  CAL  H10  SING  N  N  39  
GEF  CAK  H11  SING  N  N  40  
GEF  CAJ  H12  SING  N  N  41  
GEF  CAH  H13  SING  N  N  42  
GEF  CAH  H14  SING  N  N  43  
GEF  CAG  H15  SING  N  N  44  
GEF  CAE  H16  SING  N  N  45  
GEF  CAC  H17  SING  N  N  46  
GEF  CAB  H18  SING  N  N  47  
GEF  OAY  H19  SING  N  N  48  
GEF  CAX  H20  SING  N  N  49  
GEF  CAX  H21  SING  N  N  50  
GEF  CAX  H22  SING  N  N  51  
#   #
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
GEF  InChI             InChI                 1.03   "InChI=1S/C20H22O6/c1-23-17-7-11(3-5-15(17)21)19-13-9-26-20(14(13)10-25-19)12-4-6-16(22)18(8-12)24-2/h3-8,13-14,19-22H,9-10H2,1-2H3/t13-,14-,19+,20+/m1/s1"  
GEF  InChIKey          InChI                 1.03   HGXBRUKMWQGOIE-NSMLZSOPSA-N  
GEF  SMILES_CANONICAL  CACTVS                3.385  "COc1cc(ccc1O)[C@@H]2OC[C@@H]3[C@H]2CO[C@H]3c4ccc(O)c(OC)c4"  
GEF  SMILES            CACTVS                3.385  "COc1cc(ccc1O)[CH]2OC[CH]3[CH]2CO[CH]3c4ccc(O)c(OC)c4"  
GEF  SMILES_CANONICAL  "OpenEye OEToolkits"  2.0.7  "COc1cc(ccc1O)[C@H]2[C@@H]3CO[C@H]([C@@H]3CO2)c4ccc(c(c4)OC)O"  
GEF  SMILES            "OpenEye OEToolkits"  2.0.7  "COc1cc(ccc1O)C2C3COC(C3CO2)c4ccc(c(c4)OC)O"  
#
_pdbx_chem_comp_identifier.comp_id          GEF
_pdbx_chem_comp_identifier.type             "SYSTEMATIC NAME"
_pdbx_chem_comp_identifier.program          "OpenEye OEToolkits"
_pdbx_chem_comp_identifier.program_version  2.0.7
_pdbx_chem_comp_identifier.identifier       "4-[(3~{R},3~{a}~{S},6~{R},6~{a}~{S})-6-(3-methoxy-4-oxidanyl-phenyl)-1,3,3~{a},4,6,6~{a}-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxy-phenol"
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     GEF
_pdbx_chem_comp_synonyms.name        "(-)-pinoresinol"
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
GEF  "Create component"  2020-08-22  PDBJ  
GEF  "Modify synonyms"   2021-03-01  PDBE  
GEF  "Initial release"   2021-06-09  RCSB  
##
