data_QI9
#

_chem_comp.id                                   QI9
_chem_comp.name                                 Quinine
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C20 H24 N2 O2"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        "(3alpha,8alpha,9R)-6'-methoxycinchonan-9-ol"
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2014-10-15
_chem_comp.pdbx_modified_date                   2020-06-17
_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                       324.417
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    QI9
_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       4WNV
_chem_comp.pdbx_subcomponent_list               ?
_chem_comp.pdbx_processing_site                 RCSB
#   #
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
QI9  O1   O1   O  0  1  N  N  N  3.463  25.980  -4.237   1.098  -1.711   1.818  O1   QI9   1  
QI9  C10  C1   C  0  1  N  N  R  4.565  25.148  -4.580   0.321  -0.683   1.199  C10  QI9   2  
QI9  C11  C2   C  0  1  N  N  S  5.714  26.002  -5.155   1.229   0.187   0.327  C11  QI9   3  
QI9  N1   N1   N  0  1  N  N  S  5.428  26.529  -6.506   2.148   0.949   1.184  N1   QI9   4  
QI9  C15  C3   C  0  1  N  N  N  4.630  27.762  -6.423   2.954   0.051   2.022  C15  QI9   5  
QI9  C14  C4   C  0  1  N  N  N  5.431  28.896  -5.784   3.812  -0.846   1.125  C14  QI9   6  
QI9  C16  C5   C  0  1  N  N  N  6.718  26.866  -7.130   3.006   1.833   0.383  C16  QI9   7  
QI9  C17  C6   C  0  1  N  N  R  7.587  27.768  -6.227   3.865   0.988  -0.561  C17  QI9   8  
QI9  C18  C7   C  0  1  N  N  N  8.796  27.055  -5.702   3.567   1.366  -1.989  C18  QI9   9  
QI9  C19  C8   C  0  1  N  N  N  9.089  25.781  -5.853   4.522   1.828  -2.757  C19  QI9  10  
QI9  C13  C9   C  0  1  N  N  S  6.661  28.289  -5.118   3.532  -0.494  -0.342  C13  QI9  11  
QI9  C12  C10  C  0  1  N  N  N  6.206  27.124  -4.234   2.038  -0.705  -0.618  C12  QI9  12  
QI9  C4   C11  C  0  1  Y  N  N  5.058  24.357  -3.378  -0.748  -1.309   0.341  C4   QI9  13  
QI9  C5   C12  C  0  1  Y  N  N  4.638  24.684  -2.114  -0.591  -2.565  -0.172  C5   QI9  14  
QI9  C6   C13  C  0  1  Y  N  N  5.137  23.994  -1.021  -1.593  -3.124  -0.962  C6   QI9  15  
QI9  N    N2   N  0  1  Y  N  N  6.024  23.015  -1.089  -2.700  -2.476  -1.233  N    QI9  16  
QI9  C7   C14  C  0  1  Y  N  N  6.463  22.657  -2.340  -2.917  -1.244  -0.762  C7   QI9  17  
QI9  C3   C15  C  0  1  Y  N  N  5.999  23.288  -3.521  -1.940  -0.618   0.052  C3   QI9  18  
QI9  C2   C16  C  0  1  Y  N  N  6.460  22.809  -4.772  -2.175   0.673   0.550  C2   QI9  19  
QI9  C8   C17  C  0  1  Y  N  N  7.391  21.591  -2.452  -4.107  -0.555  -1.057  C8   QI9  20  
QI9  C9   C18  C  0  1  Y  N  N  7.818  21.162  -3.676  -4.303   0.697  -0.565  C9   QI9  21  
QI9  C1   C19  C  0  1  Y  N  N  7.345  21.767  -4.837  -3.344   1.310   0.247  C1   QI9  22  
QI9  O    O2   O  0  1  N  N  N  7.781  21.266  -6.036  -3.572   2.560   0.728  O    QI9  23  
QI9  C    C20  C  0  1  N  N  N  8.709  20.190  -6.008  -4.813   3.175   0.377  C    QI9  24  
QI9  H1   H1   H  0  1  N  N  N  2.761  25.446  -3.884   1.542  -2.299   1.192  H1   QI9  25  
QI9  H2   H2   H  0  1  N  N  N  4.255  24.433  -5.356  -0.144  -0.066   1.967  H2   QI9  26  
QI9  H3   H3   H  0  1  N  N  N  6.565  25.314  -5.266   0.619   0.877  -0.257  H3   QI9  27  
QI9  H5   H5   H  0  1  N  N  N  4.328  28.063  -7.437   3.601   0.642   2.670  H5   QI9  28  
QI9  H6   H6   H  0  1  N  N  N  3.734  27.569  -5.815   2.296  -0.568   2.631  H6   QI9  29  
QI9  H7   H7   H  0  1  N  N  N  5.742  29.615  -6.557   4.867  -0.681   1.345  H7   QI9  30  
QI9  H8   H8   H  0  1  N  N  N  4.815  29.410  -5.032   3.559  -1.891   1.304  H8   QI9  31  
QI9  H9   H9   H  0  1  N  N  N  7.267  25.935  -7.333   2.384   2.512  -0.201  H9   QI9  32  
QI9  H10  H10  H  0  1  N  N  N  6.526  27.392  -8.077   3.652   2.409   1.045  H10  QI9  33  
QI9  H11  H11  H  0  1  N  N  N  7.920  28.628  -6.826   4.920   1.162  -0.350  H11  QI9  34  
QI9  H12  H12  H  0  1  N  N  N  9.501  27.650  -5.140   2.566   1.255  -2.380  H12  QI9  35  
QI9  H13  H13  H  0  1  N  N  N  9.996  25.381  -5.425   5.523   1.939  -2.366  H13  QI9  36  
QI9  H14  H14  H  0  1  N  N  N  8.422  25.135  -6.405   4.309   2.099  -3.780  H14  QI9  37  
QI9  H15  H15  H  0  1  N  N  N  7.181  29.046  -4.513   4.139  -1.116  -0.999  H15  QI9  38  
QI9  H16  H16  H  0  1  N  N  N  5.389  27.452  -3.574   1.779  -1.750  -0.446  H16  QI9  39  
QI9  H17  H17  H  0  1  N  N  N  7.049  26.765  -3.624   1.816  -0.438  -1.652  H17  QI9  40  
QI9  H18  H18  H  0  1  N  N  N  3.920  25.478  -1.971   0.310  -3.124   0.034  H18  QI9  41  
QI9  H19  H19  H  0  1  N  N  N  4.776  24.276  -0.043  -1.454  -4.118  -1.361  H19  QI9  42  
QI9  H20  H20  H  0  1  N  N  N  6.110  23.271  -5.683  -1.435   1.159   1.168  H20  QI9  43  
QI9  H21  H21  H  0  1  N  N  N  7.765  21.113  -1.559  -4.863  -1.020  -1.673  H21  QI9  44  
QI9  H22  H22  H  0  1  N  N  N  8.526  20.349  -3.744  -5.219   1.221  -0.795  H22  QI9  45  
QI9  H23  H23  H  0  1  N  N  N  8.964  19.898  -7.037  -4.882   3.261  -0.707  H23  QI9  46  
QI9  H24  H24  H  0  1  N  N  N  9.621  20.506  -5.480  -5.638   2.564   0.746  H24  QI9  47  
QI9  H25  H25  H  0  1  N  N  N  8.261  19.333  -5.484  -4.867   4.167   0.825  H25  QI9  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
QI9  C16  N1   SING  N  N   1  
QI9  C16  C17  SING  N  N   2  
QI9  N1   C15  SING  N  N   3  
QI9  N1   C11  SING  N  N   4  
QI9  C15  C14  SING  N  N   5  
QI9  C17  C18  SING  N  N   6  
QI9  C17  C13  SING  N  N   7  
QI9  O    C    SING  N  N   8  
QI9  O    C1   SING  N  N   9  
QI9  C19  C18  DOUB  N  N  10  
QI9  C14  C13  SING  N  N  11  
QI9  C11  C10  SING  N  N  12  
QI9  C11  C12  SING  N  N  13  
QI9  C13  C12  SING  N  N  14  
QI9  C1   C2   DOUB  Y  N  15  
QI9  C1   C9   SING  Y  N  16  
QI9  C2   C3   SING  Y  N  17  
QI9  C10  O1   SING  N  N  18  
QI9  C10  C4   SING  N  N  19  
QI9  C9   C8   DOUB  Y  N  20  
QI9  C3   C4   DOUB  Y  N  21  
QI9  C3   C7   SING  Y  N  22  
QI9  C4   C5   SING  Y  N  23  
QI9  C8   C7   SING  Y  N  24  
QI9  C7   N    DOUB  Y  N  25  
QI9  C5   C6   DOUB  Y  N  26  
QI9  N    C6   SING  Y  N  27  
QI9  O1   H1   SING  N  N  28  
QI9  C10  H2   SING  N  N  29  
QI9  C11  H3   SING  N  N  30  
QI9  C15  H5   SING  N  N  31  
QI9  C15  H6   SING  N  N  32  
QI9  C14  H7   SING  N  N  33  
QI9  C14  H8   SING  N  N  34  
QI9  C16  H9   SING  N  N  35  
QI9  C16  H10  SING  N  N  36  
QI9  C17  H11  SING  N  N  37  
QI9  C18  H12  SING  N  N  38  
QI9  C19  H13  SING  N  N  39  
QI9  C19  H14  SING  N  N  40  
QI9  C13  H15  SING  N  N  41  
QI9  C12  H16  SING  N  N  42  
QI9  C12  H17  SING  N  N  43  
QI9  C5   H18  SING  N  N  44  
QI9  C6   H19  SING  N  N  45  
QI9  C2   H20  SING  N  N  46  
QI9  C8   H21  SING  N  N  47  
QI9  C9   H22  SING  N  N  48  
QI9  C    H23  SING  N  N  49  
QI9  C    H24  SING  N  N  50  
QI9  C    H25  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
QI9  SMILES            ACDLabs               12.01  "O(c4cc1c(nccc1C(O)C2N3CCC(C2)C(/C=C)C3)cc4)C"  
QI9  InChI             InChI                 1.03   "InChI=1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19-,20+/m0/s1"  
QI9  InChIKey          InChI                 1.03   LOUPRKONTZGTKE-WZBLMQSHSA-N  
QI9  SMILES_CANONICAL  CACTVS                3.385  "COc1ccc2nccc([C@@H](O)[C@@H]3C[C@@H]4CC[N@]3C[C@@H]4C=C)c2c1"  
QI9  SMILES            CACTVS                3.385  "COc1ccc2nccc([CH](O)[CH]3C[CH]4CC[N]3C[CH]4C=C)c2c1"  
QI9  SMILES_CANONICAL  "OpenEye OEToolkits"  1.9.2  "COc1ccc2c(c1)c(ccn2)[C@H]([C@@H]3C[C@@H]4CC[N@]3C[C@@H]4C=C)O"  
QI9  SMILES            "OpenEye OEToolkits"  1.9.2  "COc1ccc2c(c1)c(ccn2)C(C3CC4CCN3CC4C=C)O"  
#   #
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
QI9  "SYSTEMATIC NAME"  ACDLabs               12.01  "(3alpha,8alpha,9R)-6'-methoxycinchonan-9-ol"  
QI9  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.9.2  "(R)-[(1S,2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
QI9  "Create component"  2014-10-15  RCSB  
QI9  "Initial release"   2015-01-14  RCSB  
QI9  "Modify synonyms"   2020-06-05  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     QI9
_pdbx_chem_comp_synonyms.name        "(3alpha,8alpha,9R)-6'-methoxycinchonan-9-ol"
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
