data_USE
#

_chem_comp.id                                   USE
_chem_comp.name                                 Orientin
_chem_comp.type                                 non-polymer
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C21 H20 O11"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        "2-[3,4-bis(oxidanyl)phenyl]-8-[(2~{S},3~{R},4~{R},5~{S},6~{R})-6-(hydroxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]-5,7-bis(oxidanyl)chromen-4-one; 5281675; 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one"
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2021-03-12
_chem_comp.pdbx_modified_date                   2021-07-23
_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                       448.377
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    USE
_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       7NUH
_chem_comp.pdbx_subcomponent_list               ?
_chem_comp.pdbx_processing_site                 PDBE
#   #
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
USE  C4   C1   C  0  1  Y  N  N  25.890  15.746   5.181   3.773   2.559   0.153  C4   USE   1  
USE  C5   C2   C  0  1  Y  N  N  26.991  15.039   5.616   2.859   1.524   0.118  C5   USE   2  
USE  C6   C3   C  0  1  Y  N  N  27.675  15.435   6.767   3.308   0.200   0.117  C6   USE   3  
USE  C7   C4   C  0  1  N  N  N  28.820  14.666   7.259   2.336  -0.910   0.080  C7   USE   4  
USE  C8   C5   C  0  1  N  N  N  29.054  13.383   6.946   2.803  -2.188   0.085  C8   USE   5  
USE  C10  C6   C  0  1  Y  N  N  30.986  13.405   8.440   0.451  -2.933   0.008  C10  USE   6  
USE  C13  C7   C  0  1  Y  N  N  32.542  14.867  10.244  -2.231  -2.241  -0.058  C13  USE   7  
USE  C15  C8   C  0  1  Y  N  N  32.116  12.823   9.069  -0.526  -3.935  -0.030  C15  USE   8  
USE  C17  C9   C  0  1  N  N  R  31.324  17.886   8.851  -2.147   0.607  -1.422  C17  USE   9  
USE  C20  C10  C  0  1  N  N  R  29.490  18.271  11.045  -3.215   1.741   1.007  C20  USE  10  
USE  C21  C11  C  0  1  N  N  N  28.138  18.175  11.707  -4.340   1.823   2.041  C21  USE  11  
USE  C1   C12  C  0  1  Y  N  N  27.204  16.528   7.488   4.678  -0.070   0.151  C1   USE  12  
USE  C2   C13  C  0  1  Y  N  N  26.086  17.225   7.067   5.584   0.968   0.186  C2   USE  13  
USE  C3   C14  C  0  1  Y  N  N  25.434  16.838   5.918   5.139   2.282   0.187  C3   USE  14  
USE  C9   C15  C  0  1  N  N  N  30.160  12.658   7.494   1.885  -3.265   0.049  C9   USE  15  
USE  O1   O1   O  0  1  N  N  N  30.385  11.476   7.174   2.268  -4.424   0.052  O1   USE  16  
USE  C11  C16  C  0  1  Y  N  N  30.666  14.732   8.743   0.076  -1.578   0.012  C11  USE  17  
USE  O2   O2   O  0  1  N  N  N  29.580  15.333   8.165   1.026  -0.620   0.047  O2   USE  18  
USE  C12  C17  C  0  1  Y  N  N  31.448  15.457   9.645  -1.269  -1.244  -0.022  C12  USE  19  
USE  C14  C18  C  0  1  Y  N  N  32.885  13.543   9.958  -1.862  -3.582  -0.062  C14  USE  20  
USE  O3   O3   O  0  1  N  N  N  32.457  11.545   8.803  -0.165  -5.243  -0.034  O3   USE  21  
USE  O4   O4   O  0  1  N  N  N  33.298  15.582  11.120  -3.546  -1.905  -0.090  O4   USE  22  
USE  C16  C19  C  0  1  N  N  S  31.124  16.894   9.998  -1.685   0.205  -0.018  C16  USE  23  
USE  C18  C20  C  0  1  N  N  R  30.913  19.294   9.276  -2.624   2.062  -1.396  C18  USE  24  
USE  C19  C21  C  0  1  N  N  S  29.535  19.290   9.918  -3.738   2.204  -0.355  C19  USE  25  
USE  O5   O5   O  0  1  N  N  N  29.791  16.970  10.515  -2.758   0.390   0.906  O5   USE  26  
USE  O6   O6   O  0  1  N  N  N  28.229  17.448  12.926  -3.823   1.502   3.334  O6   USE  27  
USE  O7   O7   O  0  1  N  N  N  29.237  20.579  10.447  -4.141   3.572  -0.271  O7   USE  28  
USE  O8   O8   O  0  1  N  N  N  30.927  20.167   8.148  -3.125   2.423  -2.685  O8   USE  29  
USE  O9   O9   O  0  1  N  N  N  32.698  17.871   8.451  -1.058   0.477  -2.338  O9   USE  30  
USE  O10  O10  O  0  1  N  N  N  25.216  15.396   4.046   3.341   3.848   0.149  O10  USE  31  
USE  O11  O11  O  0  1  N  N  N  24.333  17.500   5.484   6.036   3.302   0.221  O11  USE  32  
USE  H1   H1   H  0  1  N  N  N  27.326  14.174   5.063   1.801   1.737   0.093  H1   USE  33  
USE  H2   H2   H  0  1  N  N  N  28.388  12.882   6.260   3.865  -2.379   0.116  H2   USE  34  
USE  H3   H3   H  0  1  N  N  N  30.688  17.577   8.009  -2.966  -0.041  -1.734  H3   USE  35  
USE  H4   H4   H  0  1  N  N  N  30.238  18.548  11.802  -2.389   2.382   1.317  H4   USE  36  
USE  H5   H5   H  0  1  N  N  N  27.765  19.188  11.917  -4.748   2.834   2.054  H5   USE  37  
USE  H6   H6   H  0  1  N  N  N  27.440  17.661  11.030  -5.127   1.116   1.779  H6   USE  38  
USE  H7   H7   H  0  1  N  N  N  27.717  16.836   8.387   5.028  -1.092   0.151  H7   USE  39  
USE  H8   H8   H  0  1  N  N  N  25.726  18.069   7.637   6.644   0.758   0.212  H8   USE  40  
USE  H9   H9   H  0  1  N  N  N  33.744  13.088  10.429  -2.622  -4.349  -0.091  H9   USE  41  
USE  H10  H10  H  0  1  N  N  N  31.844  11.177   8.177  -0.084  -5.631   0.848  H10  USE  42  
USE  H11  H11  H  0  1  N  N  N  34.008  15.039  11.443  -3.903  -1.798  -0.983  H11  USE  43  
USE  H12  H12  H  0  1  N  N  N  31.816  17.191  10.799  -0.839   0.825   0.277  H12  USE  44  
USE  H13  H13  H  0  1  N  N  N  31.638  19.650  10.023  -1.792   2.714  -1.132  H13  USE  45  
USE  H14  H14  H  0  1  N  N  N  28.790  19.011   9.158  -4.590   1.590  -0.647  H14  USE  46  
USE  H15  H15  H  0  1  N  N  N  27.370  17.397  13.330  -4.482   1.534   4.040  H15  USE  47  
USE  H16  H16  H  0  1  N  N  N  28.375  20.567  10.846  -4.480   3.934  -1.101  H16  USE  48  
USE  H17  H17  H  0  1  N  N  N  30.670  21.040   8.420  -3.446   3.333  -2.741  H17  USE  49  
USE  H18  H18  H  0  1  N  N  N  32.942  16.991   8.189  -1.278   0.720  -3.248  H18  USE  50  
USE  H19  H19  H  0  1  N  N  N  24.492  15.996   3.909   3.188   4.215   1.030  H19  USE  51  
USE  H20  H20  H  0  1  N  N  N  24.138  18.215   6.078   6.273   3.588   1.113  H20  USE  52  
#   #
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
USE  O10  C4   SING  N  N   1  
USE  C4   C5   DOUB  Y  N   2  
USE  C4   C3   SING  Y  N   3  
USE  O11  C3   SING  N  N   4  
USE  C5   C6   SING  Y  N   5  
USE  C3   C2   DOUB  Y  N   6  
USE  C6   C7   SING  N  N   7  
USE  C6   C1   DOUB  Y  N   8  
USE  C8   C7   DOUB  N  N   9  
USE  C8   C9   SING  N  N  10  
USE  C2   C1   SING  Y  N  11  
USE  O1   C9   DOUB  N  N  12  
USE  C7   O2   SING  N  N  13  
USE  C9   C10  SING  N  N  14  
USE  O8   C18  SING  N  N  15  
USE  O2   C11  SING  N  N  16  
USE  C10  C11  DOUB  Y  N  17  
USE  C10  C15  SING  Y  N  18  
USE  O9   C17  SING  N  N  19  
USE  C11  C12  SING  Y  N  20  
USE  O3   C15  SING  N  N  21  
USE  C17  C18  SING  N  N  22  
USE  C17  C16  SING  N  N  23  
USE  C15  C14  DOUB  Y  N  24  
USE  C18  C19  SING  N  N  25  
USE  C12  C16  SING  N  N  26  
USE  C12  C13  DOUB  Y  N  27  
USE  C19  O7   SING  N  N  28  
USE  C19  C20  SING  N  N  29  
USE  C14  C13  SING  Y  N  30  
USE  C16  O5   SING  N  N  31  
USE  C13  O4   SING  N  N  32  
USE  O5   C20  SING  N  N  33  
USE  C20  C21  SING  N  N  34  
USE  C21  O6   SING  N  N  35  
USE  C5   H1   SING  N  N  36  
USE  C8   H2   SING  N  N  37  
USE  C17  H3   SING  N  N  38  
USE  C20  H4   SING  N  N  39  
USE  C21  H5   SING  N  N  40  
USE  C21  H6   SING  N  N  41  
USE  C1   H7   SING  N  N  42  
USE  C2   H8   SING  N  N  43  
USE  C14  H9   SING  N  N  44  
USE  O3   H10  SING  N  N  45  
USE  O4   H11  SING  N  N  46  
USE  C16  H12  SING  N  N  47  
USE  C18  H13  SING  N  N  48  
USE  C19  H14  SING  N  N  49  
USE  O6   H15  SING  N  N  50  
USE  O7   H16  SING  N  N  51  
USE  O8   H17  SING  N  N  52  
USE  O9   H18  SING  N  N  53  
USE  O10  H19  SING  N  N  54  
USE  O11  H20  SING  N  N  55  
#   #
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
USE  InChI             InChI                 1.03   "InChI=1S/C21H20O11/c22-6-14-17(28)18(29)19(30)21(32-14)16-11(26)4-10(25)15-12(27)5-13(31-20(15)16)7-1-2-8(23)9(24)3-7/h1-5,14,17-19,21-26,28-30H,6H2/t14-,17-,18+,19-,21+/m1/s1"  
USE  InChIKey          InChI                 1.03   PLAPMLGJVGLZOV-VPRICQMDSA-N  
USE  SMILES_CANONICAL  CACTVS                3.385  "OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)c2c(O)cc(O)c3C(=O)C=C(Oc23)c4ccc(O)c(O)c4"  
USE  SMILES            CACTVS                3.385  "OC[CH]1O[CH]([CH](O)[CH](O)[CH]1O)c2c(O)cc(O)c3C(=O)C=C(Oc23)c4ccc(O)c(O)c4"  
USE  SMILES_CANONICAL  "OpenEye OEToolkits"  2.0.7  "c1cc(c(cc1C2=CC(=O)c3c(cc(c(c3O2)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O)O"  
USE  SMILES            "OpenEye OEToolkits"  2.0.7  "c1cc(c(cc1C2=CC(=O)c3c(cc(c(c3O2)C4C(C(C(C(O4)CO)O)O)O)O)O)O)O"  
#
_pdbx_chem_comp_identifier.comp_id          USE
_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       "2-[3,4-bis(oxidanyl)phenyl]-8-[(2~{S},3~{R},4~{R},5~{S},6~{R})-6-(hydroxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]-5,7-bis(oxidanyl)chromen-4-one"
#   #
loop_
_pdbx_chem_comp_synonyms.ordinal
_pdbx_chem_comp_synonyms.comp_id
_pdbx_chem_comp_synonyms.name
_pdbx_chem_comp_synonyms.provenance
_pdbx_chem_comp_synonyms.type
1  USE  "2-[3,4-bis(oxidanyl)phenyl]-8-[(2~{S},3~{R},4~{R},5~{S},6~{R})-6-(hydroxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]-5,7-bis(oxidanyl)chromen-4-one"  PDB      ?  
2  USE  5281675                                                                                                                                           PUBCHEM  ?  
3  USE  "2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one"                             PUBCHEM  ?  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
USE  "Create component"    2021-03-12  PDBE  
USE  "Other modification"  2021-04-02  PDBE  
USE  "Initial release"     2021-07-28  RCSB  
##
