data_GBJ
#

_chem_comp.id                                   GBJ
_chem_comp.name                                 "4-[(3R)-8,8-dimethyl-3,4-dihydro-2H,8H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C20 H20 O4"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        glabridin
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2013-10-24
_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                       324.370
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    GBJ
_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       4N86
_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
GBJ  C1   C1   C  0  1  N  N  N  -20.306  -0.716  -11.103   6.714   0.465   0.076  C1   GBJ   1  
GBJ  C2   C2   C  0  1  N  N  N  -21.407   0.097  -10.499   5.256   0.260  -0.340  C2   GBJ   2  
GBJ  C3   C3   C  0  1  N  N  N  -20.869   1.290   -9.796   4.527   1.576  -0.261  C3   GBJ   3  
GBJ  C4   C4   C  0  1  N  N  N  -20.454   1.109   -8.369   3.219   1.599  -0.012  C4   GBJ   4  
GBJ  C5   C5   C  0  1  Y  N  N  -21.330   0.094   -7.642   2.527   0.309   0.192  C5   GBJ   5  
GBJ  C6   C6   C  0  1  Y  N  N  -22.172  -0.752   -8.385   3.300  -0.827   0.460  C6   GBJ   6  
GBJ  C7   C7   C  0  1  Y  N  N  -23.004  -1.713   -7.690   2.679  -2.047   0.654  C7   GBJ   7  
GBJ  C8   C8   C  0  1  Y  N  N  -22.967  -1.803   -6.285   1.301  -2.135   0.582  C8   GBJ   8  
GBJ  C9   C9   C  0  1  Y  N  N  -22.104  -0.935   -5.530   0.528  -1.014   0.319  C9   GBJ   9  
GBJ  C10  C10  C  0  1  Y  N  N  -21.286   0.009   -6.190   1.133   0.214   0.124  C10  GBJ  10  
GBJ  O1   O1   O  0  1  N  N  N  -20.434   0.863   -5.462   0.412   1.337  -0.124  O1   GBJ  11  
GBJ  C11  C11  C  0  1  N  N  N  -20.830   1.057   -4.165  -0.941   1.182  -0.552  C11  GBJ  12  
GBJ  C12  C12  C  0  1  N  N  R  -20.959  -0.240   -3.450  -1.639   0.199   0.397  C12  GBJ  13  
GBJ  C13  C13  C  0  1  N  N  N  -22.079  -1.050   -4.014  -0.970  -1.169   0.248  C13  GBJ  14  
GBJ  C14  C14  C  0  1  Y  N  N  -21.172  -0.097   -1.957  -3.098   0.094   0.037  C14  GBJ  15  
GBJ  C15  C15  C  0  1  Y  N  N  -22.320   0.488   -1.432  -3.469  -0.342  -1.222  C15  GBJ  16  
GBJ  C16  C16  C  0  1  Y  N  N  -22.479   0.593   -0.057  -4.806  -0.440  -1.555  C16  GBJ  17  
GBJ  C17  C17  C  0  1  Y  N  N  -21.501   0.110    0.799  -5.781  -0.101  -0.626  C17  GBJ  18  
GBJ  C18  C18  C  0  1  Y  N  N  -20.358  -0.480    0.279  -5.411   0.336   0.636  C18  GBJ  19  
GBJ  C19  C19  C  0  1  Y  N  N  -20.194  -0.585   -1.095  -4.069   0.428   0.970  C19  GBJ  20  
GBJ  O2   O2   O  0  1  N  N  N  -19.056  -1.171   -1.601  -3.703   0.851   2.209  O2   GBJ  21  
GBJ  O3   O3   O  0  1  N  N  N  -21.665   0.217    2.164  -7.096  -0.197  -0.955  O3   GBJ  22  
GBJ  O4   O4   O  0  1  N  N  N  -22.255  -0.699   -9.781   4.650  -0.703   0.523  O4   GBJ  23  
GBJ  C20  C20  C  0  1  N  N  N  -22.208   0.622  -11.646   5.210  -0.255  -1.780  C20  GBJ  24  
GBJ  H1   H1   H  0  1  N  N  N  -19.676  -1.133  -10.303   6.750   0.842   1.098  H1   GBJ  25  
GBJ  H2   H2   H  0  1  N  N  N  -20.738  -1.536  -11.695   7.245  -0.485   0.020  H2   GBJ  26  
GBJ  H3   H3   H  0  1  N  N  N  -19.694  -0.076  -11.756   7.185   1.185  -0.593  H3   GBJ  27  
GBJ  H4   H4   H  0  1  N  N  N  -20.781   2.245  -10.292   5.066   2.501  -0.405  H4   GBJ  28  
GBJ  H6   H6   H  0  1  N  N  N  -19.631   1.635   -7.908   2.680   2.534   0.039  H6   GBJ  29  
GBJ  H8   H8   H  0  1  N  N  N  -23.656  -2.364   -8.253   3.268  -2.928   0.860  H8   GBJ  30  
GBJ  H9   H9   H  0  1  N  N  N  -23.587  -2.525   -5.774   0.820  -3.091   0.733  H9   GBJ  31  
GBJ  H10  H10  H  0  1  N  N  N  -20.084   1.680   -3.650  -1.449   2.146  -0.520  H10  GBJ  32  
GBJ  H11  H11  H  0  1  N  N  N  -21.803   1.570   -4.158  -0.962   0.789  -1.568  H11  GBJ  33  
GBJ  H12  H12  H  0  1  N  N  N  -20.026  -0.804   -3.600  -1.538   0.547   1.425  H12  GBJ  34  
GBJ  H13  H13  H  0  1  N  N  N  -23.033  -0.683   -3.607  -1.245  -1.603  -0.714  H13  GBJ  35  
GBJ  H14  H14  H  0  1  N  N  N  -21.941  -2.104   -3.733  -1.305  -1.827   1.050  H14  GBJ  36  
GBJ  H15  H15  H  0  1  N  N  N  -23.087   0.860   -2.094  -2.712  -0.605  -1.946  H15  GBJ  37  
GBJ  H16  H16  H  0  1  N  N  N  -23.368   1.053    0.348  -5.094  -0.780  -2.539  H16  GBJ  38  
GBJ  H17  H17  H  0  1  N  N  N  -19.595  -0.858    0.944  -6.168   0.600   1.360  H17  GBJ  39  
GBJ  H18  H18  H  0  1  N  N  N  -18.496  -1.448   -0.885  -3.587   1.808   2.280  H18  GBJ  40  
GBJ  H19  H19  H  0  1  N  N  N  -20.912  -0.159    2.604  -7.488  -1.059  -0.758  H19  GBJ  41  
GBJ  H20  H20  H  0  1  N  N  N  -23.039   1.233  -11.264   5.745  -1.203  -1.844  H20  GBJ  42  
GBJ  H21  H21  H  0  1  N  N  N  -21.565   1.240  -12.290   4.173  -0.403  -2.081  H21  GBJ  43  
GBJ  H22  H22  H  0  1  N  N  N  -22.609  -0.220  -12.229   5.680   0.472  -2.442  H22  GBJ  44  
#   #
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
GBJ  C20  C2   SING  N  N   1  
GBJ  C1   C2   SING  N  N   2  
GBJ  C2   C3   SING  N  N   3  
GBJ  C2   O4   SING  N  N   4  
GBJ  C3   C4   DOUB  N  N   5  
GBJ  O4   C6   SING  N  N   6  
GBJ  C6   C7   SING  Y  N   7  
GBJ  C6   C5   DOUB  Y  N   8  
GBJ  C4   C5   SING  N  N   9  
GBJ  C7   C8   DOUB  Y  N  10  
GBJ  C5   C10  SING  Y  N  11  
GBJ  C8   C9   SING  Y  N  12  
GBJ  C10  C9   DOUB  Y  N  13  
GBJ  C10  O1   SING  N  N  14  
GBJ  C9   C13  SING  N  N  15  
GBJ  O1   C11  SING  N  N  16  
GBJ  C11  C12  SING  N  N  17  
GBJ  C13  C12  SING  N  N  18  
GBJ  C12  C14  SING  N  N  19  
GBJ  C14  C15  SING  Y  N  20  
GBJ  C14  C19  DOUB  Y  N  21  
GBJ  O2   C19  SING  N  N  22  
GBJ  C15  C16  DOUB  Y  N  23  
GBJ  C19  C18  SING  Y  N  24  
GBJ  C16  C17  SING  Y  N  25  
GBJ  C18  C17  DOUB  Y  N  26  
GBJ  C17  O3   SING  N  N  27  
GBJ  C1   H1   SING  N  N  28  
GBJ  C1   H2   SING  N  N  29  
GBJ  C1   H3   SING  N  N  30  
GBJ  C3   H4   SING  N  N  31  
GBJ  C4   H6   SING  N  N  32  
GBJ  C7   H8   SING  N  N  33  
GBJ  C8   H9   SING  N  N  34  
GBJ  C11  H10  SING  N  N  35  
GBJ  C11  H11  SING  N  N  36  
GBJ  C12  H12  SING  N  N  37  
GBJ  C13  H13  SING  N  N  38  
GBJ  C13  H14  SING  N  N  39  
GBJ  C15  H15  SING  N  N  40  
GBJ  C16  H16  SING  N  N  41  
GBJ  C18  H17  SING  N  N  42  
GBJ  O2   H18  SING  N  N  43  
GBJ  O3   H19  SING  N  N  44  
GBJ  C20  H20  SING  N  N  45  
GBJ  C20  H21  SING  N  N  46  
GBJ  C20  H22  SING  N  N  47  
#   #
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
GBJ  SMILES            ACDLabs               12.01  "O4c2c1C=CC(Oc1ccc2CC(c3ccc(O)cc3O)C4)(C)C"  
GBJ  InChI             InChI                 1.03   "InChI=1S/C20H20O4/c1-20(2)8-7-16-18(24-20)6-3-12-9-13(11-23-19(12)16)15-5-4-14(21)10-17(15)22/h3-8,10,13,21-22H,9,11H2,1-2H3/t13-/m0/s1"  
GBJ  InChIKey          InChI                 1.03   LBQIJVLKGVZRIW-ZDUSSCGKSA-N  
GBJ  SMILES_CANONICAL  CACTVS                3.385  "CC1(C)Oc2ccc3C[C@@H](COc3c2C=C1)c4ccc(O)cc4O"  
GBJ  SMILES            CACTVS                3.385  "CC1(C)Oc2ccc3C[CH](COc3c2C=C1)c4ccc(O)cc4O"  
GBJ  SMILES_CANONICAL  "OpenEye OEToolkits"  1.7.6  "CC1(C=Cc2c(ccc3c2OC[C@H](C3)c4ccc(cc4O)O)O1)C"  
GBJ  SMILES            "OpenEye OEToolkits"  1.7.6  "CC1(C=Cc2c(ccc3c2OCC(C3)c4ccc(cc4O)O)O1)C"  
#   #
loop_
_pdbx_chem_comp_identifier.comp_id
_pdbx_chem_comp_identifier.type
_pdbx_chem_comp_identifier.program
_pdbx_chem_comp_identifier.program_version
_pdbx_chem_comp_identifier.identifier
GBJ  "SYSTEMATIC NAME"  ACDLabs               12.01  "4-[(3R)-8,8-dimethyl-3,4-dihydro-2H,8H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol"  
GBJ  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.7.6  "4-[(3R)-8,8-dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
GBJ  "Create component"  2013-10-24  PDBJ  
GBJ  "Initial release"   2014-02-19  RCSB  
GBJ  "Modify synonyms"   2021-03-01  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     GBJ
_pdbx_chem_comp_synonyms.name        glabridin
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
