data_M09
#

_chem_comp.id                                   M09
_chem_comp.name                                 "(3S,5R,7R,8S,9S,10R)-7-(hydroxymethyl)-3-(4-nitrophenyl)-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                              "C14 H18 N2 O8"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        "(1R)-3'-(4-nitrophenyl)-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                       342.301
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    M09
_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       2QRM
_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
M09  C10  C10  C   0  1  Y  N  N  36.678  24.502  31.192  -2.926   1.448  -0.555  C10  M09   1  
M09  C11  C11  C   0  1  Y  N  N  37.342  24.956  32.340  -4.285   1.204  -0.625  C11  M09   2  
M09  C12  C12  C   0  1  Y  N  N  36.609  25.456  33.424  -4.814   0.069  -0.040  C12  M09   3  
M09  N2   N2   N   1  1  N  N  N  37.218  25.898  34.535  -6.269  -0.191  -0.115  N2   M09   4  
M09  O9   O9   O   0  1  N  N  N  38.619  26.110  34.557  -7.000   0.594  -0.691  O9   M09   5  
M09  O8   O8   O  -1  1  N  N  N  36.458  26.160  35.710  -6.736  -1.191   0.401  O8   M09   6  
M09  C13  C13  C   0  1  Y  N  N  35.216  25.498  33.352  -3.985  -0.822   0.614  C13  M09   7  
M09  C14  C14  C   0  1  Y  N  N  34.557  25.044  32.209  -2.626  -0.578   0.684  C14  M09   8  
M09  C9   C9   C   0  1  Y  N  N  35.278  24.543  31.128  -2.096   0.554   0.094  C9   M09   9  
M09  C8   C8   C   0  1  N  N  S  34.584  24.112  29.989  -0.614   0.820   0.170  C8   M09  10  
M09  C7   C7   C   0  1  N  N  N  35.179  23.432  28.760   0.153  -0.054  -0.857  C7   M09  11  
M09  N1   N1   N   0  1  N  N  N  33.271  24.252  29.782  -0.068   0.373   1.473  N1   M09  12  
M09  O7   O7   O   0  1  N  N  N  32.850  23.743  28.511   1.244  -0.238   1.233  O7   M09  13  
M09  C1   C1   C   0  1  N  N  R  33.942  22.976  27.979   1.533  -0.179  -0.175  C1   M09  14  
M09  O5   O5   O   0  1  N  N  N  33.710  21.573  28.234   2.329   0.961  -0.477  O5   M09  15  
M09  C5   C5   C   0  1  N  N  R  32.516  21.051  27.585   3.621   0.952   0.136  C5   M09  16  
M09  C6   C6   C   0  1  N  N  N  32.373  19.583  28.001   4.381   2.221  -0.257  C6   M09  17  
M09  O6   O6   O   0  1  N  N  N  33.411  18.813  27.389   3.713   3.363   0.284  O6   M09  18  
M09  C4   C4   C   0  1  N  N  S  32.624  21.222  26.050   4.400  -0.277  -0.339  C4   M09  19  
M09  O4   O4   O   0  1  N  N  N  31.413  20.789  25.424   5.675  -0.313   0.306  O4   M09  20  
M09  C3   C3   C   0  1  N  N  S  32.912  22.673  25.656   3.612  -1.542   0.013  C3   M09  21  
M09  O3   O3   O   0  1  N  N  N  33.181  22.721  24.244   4.303  -2.690  -0.483  O3   M09  22  
M09  C2   C2   C   0  1  N  N  R  34.111  23.224  26.456   2.224  -1.460  -0.632  C2   M09  23  
M09  O2   O2   O   0  1  N  N  N  34.303  24.619  26.170   1.445  -2.590  -0.235  O2   M09  24  
M09  H10  H10  H   0  1  N  N  N  37.245  24.120  30.356  -2.512   2.335  -1.013  H10  M09  25  
M09  H11  H11  H   0  1  N  N  N  38.420  24.920  32.389  -4.933   1.901  -1.137  H11  M09  26  
M09  H13  H13  H   0  1  N  N  N  34.646  25.883  34.184  -4.398  -1.709   1.071  H13  M09  27  
M09  H14  H14  H   0  1  N  N  N  33.479  25.081  32.162  -1.978  -1.275   1.195  H14  M09  28  
M09  H8   H8   H   0  1  N  N  N  35.177  24.317  30.892  -0.405   1.878   0.009  H8   M09  29  
M09  H71  1H7  H   0  1  N  N  N  35.819  22.582  29.037  -0.318  -1.030  -0.970  H71  M09  30  
M09  H72  2H7  H   0  1  N  N  N  35.833  24.097  28.177   0.235   0.453  -1.819  H72  M09  31  
M09  HN1  HN1  H   0  1  N  N  N  33.048  25.226  29.820  -0.694  -0.280   1.923  HN1  M09  32  
M09  H5   H5   H   0  1  N  N  N  31.616  21.603  27.895   3.510   0.916   1.219  H5   M09  33  
M09  H61  1H6  H   0  1  N  N  N  31.393  19.203  27.676   5.396   2.173   0.136  H61  M09  34  
M09  H62  2H6  H   0  1  N  N  N  32.451  19.502  29.095   4.415   2.302  -1.344  H62  M09  35  
M09  HO6  HO6  H   0  1  N  N  N  33.186  18.642  26.482   4.141   4.205   0.074  HO6  M09  36  
M09  H4   H4   H   0  1  N  N  N  33.467  20.603  25.707   4.540  -0.224  -1.419  H4   M09  37  
M09  HO4  HO4  H   0  1  N  N  N  30.733  20.693  26.081   6.227   0.461   0.129  HO4  M09  38  
M09  H3   H3   H   0  1  N  N  N  32.039  23.300  25.888   3.507  -1.617   1.096  H3   M09  39  
M09  HO3  HO3  H   0  1  N  N  N  32.361  22.732  23.765   5.193  -2.800  -0.122  HO3  M09  40  
M09  H2   H2   H   0  1  N  N  N  35.013  22.680  26.140   2.327  -1.451  -1.717  H2   M09  41  
M09  HO2  HO2  H   0  1  N  N  N  34.345  25.107  26.984   1.828  -3.441  -0.489  HO2  M09  42  
#   #
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
M09  O3   C3   SING  N  N   1  
M09  O4   C4   SING  N  N   2  
M09  C3   C4   SING  N  N   3  
M09  C3   C2   SING  N  N   4  
M09  C4   C5   SING  N  N   5  
M09  O2   C2   SING  N  N   6  
M09  C2   C1   SING  N  N   7  
M09  O6   C6   SING  N  N   8  
M09  C5   C6   SING  N  N   9  
M09  C5   O5   SING  N  N  10  
M09  C1   O5   SING  N  N  11  
M09  C1   O7   SING  N  N  12  
M09  C1   C7   SING  N  N  13  
M09  O7   N1   SING  N  N  14  
M09  C7   C8   SING  N  N  15  
M09  N1   C8   SING  N  N  16  
M09  C8   C9   SING  N  N  17  
M09  C9   C10  DOUB  Y  N  18  
M09  C9   C14  SING  Y  N  19  
M09  C10  C11  SING  Y  N  20  
M09  C14  C13  DOUB  Y  N  21  
M09  C11  C12  DOUB  Y  N  22  
M09  C13  C12  SING  Y  N  23  
M09  C12  N2   SING  N  N  24  
M09  N2   O9   DOUB  N  N  25  
M09  N2   O8   SING  N  N  26  
M09  C10  H10  SING  N  N  27  
M09  C11  H11  SING  N  N  28  
M09  C13  H13  SING  N  N  29  
M09  C14  H14  SING  N  N  30  
M09  C8   H8   SING  N  N  31  
M09  C7   H71  SING  N  N  32  
M09  C7   H72  SING  N  N  33  
M09  N1   HN1  SING  N  N  34  
M09  C5   H5   SING  N  N  35  
M09  C6   H61  SING  N  N  36  
M09  C6   H62  SING  N  N  37  
M09  O6   HO6  SING  N  N  38  
M09  C4   H4   SING  N  N  39  
M09  O4   HO4  SING  N  N  40  
M09  C3   H3   SING  N  N  41  
M09  O3   HO3  SING  N  N  42  
M09  C2   H2   SING  N  N  43  
M09  O2   HO2  SING  N  N  44  
#   #
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
M09  SMILES            ACDLabs               10.04  "[O-][N+](=O)c1ccc(cc1)C3NOC2(OC(C(O)C(O)C2O)CO)C3"  
M09  SMILES_CANONICAL  CACTVS                3.341  "OC[C@H]1O[C@@]2(C[C@H](NO2)c3ccc(cc3)[N+]([O-])=O)[C@H](O)[C@@H](O)[C@@H]1O"  
M09  SMILES            CACTVS                3.341  "OC[CH]1O[C]2(C[CH](NO2)c3ccc(cc3)[N+]([O-])=O)[CH](O)[CH](O)[CH]1O"  
M09  SMILES_CANONICAL  "OpenEye OEToolkits"  1.5.0  "c1cc(ccc1C2C[C@]3([C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)ON2)[N+](=O)[O-]"  
M09  SMILES            "OpenEye OEToolkits"  1.5.0  "c1cc(ccc1C2CC3(C(C(C(C(O3)CO)O)O)O)ON2)[N+](=O)[O-]"  
M09  InChI             InChI                 1.03   "InChI=1S/C14H18N2O8/c17-6-10-11(18)12(19)13(20)14(23-10)5-9(15-24-14)7-1-3-8(4-2-7)16(21)22/h1-4,9-13,15,17-20H,5-6H2/t9-,10+,11+,12-,13+,14+/m0/s1"  
M09  InChIKey          InChI                 1.03   FYUHHVCQKVTVLN-GMDXDWKASA-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
M09  "SYSTEMATIC NAME"  ACDLabs               10.04  "(3S,5R,7R,8S,9S,10R)-7-(hydroxymethyl)-3-(4-nitrophenyl)-1,6-dioxa-2-azaspiro[4.5]decane-8,9,10-triol"  
M09  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.5.0  "(5R,6R,7S,8S,9R)-9-(hydroxymethyl)-3-(4-nitrophenyl)-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
M09  "Create component"      2007-09-04  EBI   
M09  "Modify aromatic_flag"  2011-06-04  RCSB  
M09  "Modify descriptor"     2011-06-04  RCSB  
M09  "Modify synonyms"       2021-03-13  RCSB  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     M09
_pdbx_chem_comp_synonyms.name        "(1R)-3'-(4-nitrophenyl)-spiro[1,5-anhydro-D-glucitol-1,5'-isoxazoline]"
_pdbx_chem_comp_synonyms.provenance  PDB
_pdbx_chem_comp_synonyms.type        ?
##
