data_S13
#

_chem_comp.id                                   S13
_chem_comp.name                                 "(3S,5R,7R,8S,9S,10R)-7-(hydroxymethyl)-3-(4-methylphenyl)-1,6-dioxa-2-azaspiro[4.5]decane-8,9,10-triol"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C15 H21 N O6"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        "(1R)-3'-(4-methylphenyl)-spiro[1,5-anhydro-D-glucitol-1,5'-isoxazoline]"
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2007-09-04
_chem_comp.pdbx_modified_date                   2021-03-13
_chem_comp.pdbx_ambiguous_flag                  ?
_chem_comp.pdbx_release_status                  REL
_chem_comp.pdbx_replaced_by                     ?
_chem_comp.pdbx_replaces                        ?
_chem_comp.formula_weight                       311.330
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    S13
_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       2QRQ
_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
S13  C10   C10   C  0  1  Y  N  N  36.183  24.382  30.588   3.631   1.327   0.636  C10   S13   1  
S13  C11   C11   C  0  1  Y  N  N  36.872  24.834  31.718   4.983   1.052   0.712  C11   S13   2  
S13  C12   C12   C  0  1  Y  N  N  36.169  25.170  32.876   5.493  -0.083   0.109  C12   S13   3  
S13  C15   C15   C  0  1  N  N  N  36.919  25.670  34.118   6.968  -0.382   0.192  C15   S13   4  
S13  C13   C13   C  0  1  Y  N  N  34.784  25.040  32.914   4.650  -0.943  -0.570  C13   S13   5  
S13  C14   C14   C  0  1  Y  N  N  34.097  24.590  31.784   3.297  -0.668  -0.646  C14   S13   6  
S13  C9    C9    C  0  1  Y  N  N  34.793  24.251  30.621   2.788   0.467  -0.043  C9    S13   7  
S13  C8    C8    C  0  1  N  N  S  34.092  23.818  29.492   1.313   0.767  -0.126  C8    S13   8  
S13  C7    C7    C  0  1  N  N  N  34.673  23.114  28.265   0.517  -0.115   0.873  C7    S13   9  
S13  N1    N1    N  0  1  N  N  N  32.788  23.984  29.290   0.771   0.363  -1.444  N1    S13  10  
S13  O7    O7    O  0  1  N  N  N  32.357  23.460  28.026  -0.557  -0.225  -1.231  O7    S13  11  
S13  C1    C1    C  0  1  N  N  R  33.433  22.682  27.482  -0.858  -0.193   0.175  C1    S13  12  
S13  O5    O5    O  0  1  N  N  N  33.185  21.279  27.717  -1.632   0.956   0.497  O5    S13  13  
S13  C5    C5    C  0  1  N  N  R  31.999  20.772  27.042  -2.919   0.990  -0.127  C5    S13  14  
S13  C6    C6    C  0  1  N  N  N  31.859  19.310  27.469  -3.654   2.265   0.289  C6    S13  15  
S13  O6    O6    O  0  1  N  N  N  32.930  18.545  26.910  -2.957   3.405  -0.218  O6    S13  16  
S13  C4    C4    C  0  1  N  N  S  32.142  20.937  25.518  -3.728  -0.233   0.311  C4    S13  17  
S13  O4    O4    O  0  1  N  N  N  30.964  20.461  24.843  -4.997  -0.225  -0.347  O4    S13  18  
S13  C3    C3    C  0  1  N  N  S  32.409  22.407  25.153  -2.964  -1.506  -0.065  C3    S13  19  
S13  O3    O3    O  0  1  N  N  N  32.689  22.511  23.753  -3.684  -2.650   0.397  O3    S13  20  
S13  C2    C2    C  0  1  N  N  R  33.595  22.967  25.967  -1.581  -1.470   0.595  C2    S13  21  
S13  O2    O2    O  0  1  N  N  N  33.722  24.374  25.739  -0.823  -2.607   0.177  O2    S13  22  
S13  H10   H10   H  0  1  N  N  N  36.727  24.134  29.688   3.232   2.211   1.111  H10   S13  23  
S13  H11   H11   H  0  1  N  N  N  37.948  24.923  31.695   5.642   1.724   1.242  H11   S13  24  
S13  H151  1H15  H  0  0  N  N  N  37.986  25.790  33.879   7.167  -0.985   1.078  H151  S13  25  
S13  H152  2H15  H  0  0  N  N  N  36.503  26.639  34.432   7.278  -0.930  -0.698  H152  S13  26  
S13  H153  3H15  H  0  0  N  N  N  36.806  24.940  34.933   7.525   0.553   0.255  H153  S13  27  
S13  H13   H13   H  0  1  N  N  N  34.242  25.286  33.815   5.048  -1.829  -1.040  H13   S13  28  
S13  H14   H14   H  0  1  N  N  N  33.021  24.504  31.810   2.639  -1.340  -1.176  H14   S13  29  
S13  H8    H8    H  0  1  N  N  N  34.702  23.976  30.394   1.126   1.824   0.060  H8    S13  30  
S13  H71   1H7   H  0  1  N  N  N  35.291  22.250  28.550   0.966  -1.104   0.967  H71   S13  31  
S13  H72   2H7   H  0  1  N  N  N  35.343  23.761  27.680   0.437   0.370   1.846  H72   S13  32  
S13  HN1   HN1   H  0  1  N  N  N  32.586  24.963  29.313   1.386  -0.292  -1.903  HN1   S13  33  
S13  H5    H5    H  0  1  N  N  N  31.091  21.329  27.317  -2.797   0.978  -1.210  H5    S13  34  
S13  H61   1H6   H  0  1  N  N  N  30.898  18.913  27.109  -4.667   2.249  -0.114  H61   S13  35  
S13  H62   2H6   H  0  1  N  N  N  31.895  19.244  28.566  -3.698   2.321   1.377  H62   S13  36  
S13  HO6   HO6   H  0  1  N  N  N  32.753  18.375  25.992  -3.368   4.251   0.008  HO6   S13  37  
S13  H4    H4    H  0  1  N  N  N  33.001  20.334  25.188  -3.878  -0.203   1.390  H4    S13  38  
S13  HO4   HO4   H  0  1  N  N  N  30.259  20.356  25.471  -5.535   0.556  -0.156  HO4   S13  39  
S13  H3    H3    H  0  1  N  N  N  31.513  22.997  25.395  -2.851  -1.557  -1.148  H3    S13  40  
S13  HO3   HO3   H  0  1  N  N  N  31.873  22.534  23.267  -4.574  -2.732   0.026  HO3   S13  41  
S13  H2    H2    H  0  1  N  N  N  34.509  22.458  25.628  -1.694  -1.484   1.679  H2    S13  42  
S13  HO2   HO2   H  0  1  N  N  N  33.750  24.829  26.572  -1.227  -3.455   0.408  HO2   S13  43  
#   #
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
S13  O3   C3    SING  N  N   1  
S13  O4   C4    SING  N  N   2  
S13  C3   C4    SING  N  N   3  
S13  C3   C2    SING  N  N   4  
S13  C4   C5    SING  N  N   5  
S13  O2   C2    SING  N  N   6  
S13  C2   C1    SING  N  N   7  
S13  O6   C6    SING  N  N   8  
S13  C5   C6    SING  N  N   9  
S13  C5   O5    SING  N  N  10  
S13  C1   O5    SING  N  N  11  
S13  C1   O7    SING  N  N  12  
S13  C1   C7    SING  N  N  13  
S13  O7   N1    SING  N  N  14  
S13  C7   C8    SING  N  N  15  
S13  N1   C8    SING  N  N  16  
S13  C8   C9    SING  N  N  17  
S13  C10  C9    DOUB  Y  N  18  
S13  C10  C11   SING  Y  N  19  
S13  C9   C14   SING  Y  N  20  
S13  C11  C12   DOUB  Y  N  21  
S13  C14  C13   DOUB  Y  N  22  
S13  C12  C13   SING  Y  N  23  
S13  C12  C15   SING  N  N  24  
S13  C10  H10   SING  N  N  25  
S13  C11  H11   SING  N  N  26  
S13  C15  H151  SING  N  N  27  
S13  C15  H152  SING  N  N  28  
S13  C15  H153  SING  N  N  29  
S13  C13  H13   SING  N  N  30  
S13  C14  H14   SING  N  N  31  
S13  C8   H8    SING  N  N  32  
S13  C7   H71   SING  N  N  33  
S13  C7   H72   SING  N  N  34  
S13  N1   HN1   SING  N  N  35  
S13  C5   H5    SING  N  N  36  
S13  C6   H61   SING  N  N  37  
S13  C6   H62   SING  N  N  38  
S13  O6   HO6   SING  N  N  39  
S13  C4   H4    SING  N  N  40  
S13  O4   HO4   SING  N  N  41  
S13  C3   H3    SING  N  N  42  
S13  O3   HO3   SING  N  N  43  
S13  C2   H2    SING  N  N  44  
S13  O2   HO2   SING  N  N  45  
#   #
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
S13  SMILES            ACDLabs               10.04  "O1C(C(O)C(O)C(O)C13ONC(c2ccc(cc2)C)C3)CO"  
S13  SMILES_CANONICAL  CACTVS                3.341  "Cc1ccc(cc1)[C@@H]2C[C@]3(ON2)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O"  
S13  SMILES            CACTVS                3.341  "Cc1ccc(cc1)[CH]2C[C]3(ON2)O[CH](CO)[CH](O)[CH](O)[CH]3O"  
S13  SMILES_CANONICAL  "OpenEye OEToolkits"  1.5.0  "Cc1ccc(cc1)C2C[C@]3([C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)ON2"  
S13  SMILES            "OpenEye OEToolkits"  1.5.0  "Cc1ccc(cc1)C2CC3(C(C(C(C(O3)CO)O)O)O)ON2"  
S13  InChI             InChI                 1.03   "InChI=1S/C15H21NO6/c1-8-2-4-9(5-3-8)10-6-15(22-16-10)14(20)13(19)12(18)11(7-17)21-15/h2-5,10-14,16-20H,6-7H2,1H3/t10-,11+,12+,13-,14+,15+/m0/s1"  
S13  InChIKey          InChI                 1.03   HRCKGDOSPBFICB-MZHQWRCYSA-N  
#   #
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
S13  "SYSTEMATIC NAME"  ACDLabs               10.04  "(3S,5R,7R,8S,9S,10R)-7-(hydroxymethyl)-3-(4-methylphenyl)-1,6-dioxa-2-azaspiro[4.5]decane-8,9,10-triol"  
S13  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.5.0  "(5R,6R,7S,8S,9R)-9-(hydroxymethyl)-3-(4-methylphenyl)-1,10-dioxa-2-azaspiro[4.5]decane-6,7,8-triol"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
S13  "Create component"      2007-09-04  EBI   
S13  "Modify aromatic_flag"  2011-06-04  RCSB  
S13  "Modify descriptor"     2011-06-04  RCSB  
S13  "Modify synonyms"       2021-03-13  RCSB  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     S13
_pdbx_chem_comp_synonyms.name        "(1R)-3'-(4-methylphenyl)-spiro[1,5-anhydro-D-glucitol-1,5'-isoxazoline]"
_pdbx_chem_comp_synonyms.provenance  PDB
_pdbx_chem_comp_synonyms.type        ?
##
