data_16F
#

_chem_comp.id                                   16F
_chem_comp.name                                 "N-({(2Z)-2-[(3-hydroxyphenyl)methylidene]hydrazino}carbonothioyl)-beta-D-glucopyranosylamine"
_chem_comp.type                                 D-saccharide
_chem_comp.pdbx_type                            ATOMS
_chem_comp.formula                              "C14 H19 N3 O6 S"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        
;3-hydroxybenzaldehyde-4-(beta-D-glucopyranosyl) thiosemicarbazone;
N-({(2Z)-2-[(3-hydroxyphenyl)methylidene]hydrazino}carbonothioyl)-beta-D-glucosylamine;
N-({(2Z)-2-[(3-hydroxyphenyl)methylidene]hydrazino}carbonothioyl)-D-glucosylamine;
N-({(2Z)-2-[(3-hydroxyphenyl)methylidene]hydrazino}carbonothioyl)-glucosylamine
;

_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2010-04-30
_chem_comp.pdbx_modified_date                   2020-07-17
_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                       357.382
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    16F
_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       3MRV
_chem_comp.pdbx_subcomponent_list               ?
_chem_comp.pdbx_processing_site                 RCSB
#   #
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  16F  "3-hydroxybenzaldehyde-4-(beta-D-glucopyranosyl) thiosemicarbazone"                       PDB  ?  
2  16F  "N-({(2Z)-2-[(3-hydroxyphenyl)methylidene]hydrazino}carbonothioyl)-beta-D-glucosylamine"  PDB  ?  
3  16F  "N-({(2Z)-2-[(3-hydroxyphenyl)methylidene]hydrazino}carbonothioyl)-D-glucosylamine"       PDB  ?  
4  16F  "N-({(2Z)-2-[(3-hydroxyphenyl)methylidene]hydrazino}carbonothioyl)-glucosylamine"         PDB  ?  
#   #
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
16F  C1   C1   C  0  1  N  N  R  33.695  22.894  27.962  -2.017  -0.360  -0.261  C1   16F   1  
16F  N1   N1   N  0  1  N  N  N  34.780  23.367  28.893  -0.622  -0.671   0.062  N1   16F   2  
16F  S1   S1   S  0  1  N  N  N  32.896  24.570  30.392   0.001   0.743  -2.099  S1   16F   3  
16F  C2   C2   C  0  1  N  N  R  33.970  23.136  26.460  -2.905  -1.550   0.112  C2   16F   4  
16F  N2   N2   N  0  1  N  N  N  35.548  24.497  30.788   1.654  -0.494  -0.427  N2   16F   5  
16F  O2   O2   O  0  1  N  N  N  34.155  24.531  26.209  -2.529  -2.689  -0.665  O2   16F   6  
16F  C3   C3   C  0  1  N  N  S  32.813  22.573  25.598  -4.367  -1.195  -0.172  C3   16F   7  
16F  N3   N3   N  0  1  N  N  N  36.703  24.161  30.496   1.956  -1.273   0.698  N3   16F   8  
16F  O3   O3   O  0  1  N  N  N  33.106  22.676  24.203  -5.210  -2.273   0.242  O3   16F   9  
16F  C4   C4   C  0  1  N  N  S  32.534  21.106  25.945  -4.734   0.071   0.608  C4   16F  10  
16F  O4   O4   O  0  1  N  N  N  31.354  20.660  25.270  -6.075   0.453   0.295  O4   16F  11  
16F  C5   C5   C  0  1  N  N  R  32.362  20.933  27.467  -3.776   1.199   0.216  C5   16F  12  
16F  O5   O5   O  0  1  N  N  N  33.523  21.461  28.153  -2.431   0.791   0.477  O5   16F  13  
16F  C6   C6   C  0  1  N  N  N  32.222  19.462  27.848  -4.098   2.450   1.035  C6   16F  14  
16F  O6   O6   O  0  1  N  N  N  33.271  18.717  27.222  -3.283   3.535   0.588  O6   16F  15  
16F  C7   C7   C  0  1  N  N  N  34.533  24.106  29.992   0.370  -0.208  -0.724  C7   16F  16  
16F  O7   O7   O  0  1  N  N  N  40.890  26.938  33.846   7.864  -0.239   0.445  O7   16F  17  
16F  C8   C8   C  0  1  N  N  N  37.859  24.421  31.126   3.192  -1.449   1.052  C8   16F  18  
16F  C9   C9   C  0  1  Y  N  N  38.068  25.167  32.292   4.228  -0.498   0.610  C9   16F  19  
16F  C10  C10  C  0  1  Y  N  N  39.348  25.686  32.512   5.580  -0.824   0.739  C10  16F  20  
16F  C11  C11  C  0  1  Y  N  N  39.634  26.440  33.651   6.547   0.074   0.321  C11  16F  21  
16F  C12  C12  C  0  1  Y  N  N  38.628  26.684  34.588   6.173   1.295  -0.224  C12  16F  22  
16F  C13  C13  C  0  1  Y  N  N  37.345  26.171  34.375   4.835   1.620  -0.352  C13  16F  23  
16F  C14  C14  C  0  1  Y  N  N  37.065  25.415  33.233   3.862   0.731   0.055  C14  16F  24  
16F  H1   H1   H  0  1  N  N  N  32.801  23.482  28.216  -2.107  -0.160  -1.328  H1   16F  25  
16F  HN1  HN1  H  0  1  N  N  N  35.727  23.121  28.686  -0.413  -1.210   0.841  HN1  16F  26  
16F  H2   H2   H  0  1  N  N  N  34.893  22.607  26.182  -2.784  -1.777   1.172  H2   16F  27  
16F  HN2  HN2  H  0  1  N  N  N  35.371  25.050  31.602   2.368  -0.161  -0.993  HN2  16F  28  
16F  HO2  HO2  H  0  1  N  Y  N  34.323  24.667  25.284  -1.611  -2.967  -0.538  HO2  16F  29  
16F  H3   H3   H  0  1  N  N  N  31.921  23.177  25.822  -4.499  -1.017  -1.239  H3   16F  30  
16F  HO3  HO3  H  0  1  N  Y  N  32.381  22.324  23.700  -5.028  -3.109  -0.207  HO3  16F  31  
16F  H4   H4   H  0  1  N  N  N  33.391  20.500  25.616  -4.651  -0.123   1.678  H4   16F  32  
16F  HO4  HO4  H  0  1  N  Y  N  31.188  19.751  25.490  -6.737  -0.218   0.513  HO4  16F  33  
16F  H5   H5   H  0  1  N  N  N  31.450  21.474  27.760  -3.890   1.419  -0.845  H5   16F  34  
16F  H61  H6   H  0  1  N  N  N  32.294  19.355  28.940  -5.149   2.708   0.906  H61  16F  35  
16F  H62  H6A  H  0  1  N  N  N  31.247  19.084  27.509  -3.899   2.256   2.089  H62  16F  36  
16F  HO6  HO6  H  0  1  N  Y  N  33.191  17.799  27.455  -3.434   4.363   1.064  HO6  16F  37  
16F  HO7  HO7  H  0  1  N  N  N  40.915  27.423  34.662   8.234  -0.693  -0.324  HO7  16F  38  
16F  H8   H8   H  0  1  N  N  N  38.745  23.999  30.674   3.461  -2.293   1.670  H8   16F  39  
16F  H10  H10  H  0  1  N  N  N  40.128  25.500  31.788   5.869  -1.774   1.163  H10  16F  40  
16F  H12  H12  H  0  1  N  N  N  38.840  27.266  35.473   6.930   1.994  -0.548  H12  16F  41  
16F  H13  H13  H  0  1  N  N  N  36.565  26.360  35.098   4.550   2.572  -0.776  H13  16F  42  
16F  H14  H14  H  0  1  N  N  N  36.071  25.022  33.078   2.818   0.987  -0.050  H14  16F  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
16F  C2   C1   SING  N  N   1  
16F  C1   O5   SING  N  N   2  
16F  C1   N1   SING  N  N   3  
16F  C1   H1   SING  N  N   4  
16F  N1   C7   SING  N  N   5  
16F  N1   HN1  SING  N  N   6  
16F  C7   S1   DOUB  N  N   7  
16F  C3   C2   SING  N  N   8  
16F  O2   C2   SING  N  N   9  
16F  C2   H2   SING  N  N  10  
16F  C7   N2   SING  N  N  11  
16F  N3   N2   SING  N  N  12  
16F  N2   HN2  SING  N  N  13  
16F  O2   HO2  SING  N  N  14  
16F  O3   C3   SING  N  Z  15  
16F  C3   C4   SING  N  N  16  
16F  C3   H3   SING  N  N  17  
16F  N3   C8   DOUB  N  N  18  
16F  O3   HO3  SING  N  N  19  
16F  O4   C4   SING  N  N  20  
16F  C4   C5   SING  N  N  21  
16F  C4   H4   SING  N  N  22  
16F  O4   HO4  SING  N  N  23  
16F  C5   C6   SING  N  N  24  
16F  C5   O5   SING  N  N  25  
16F  C5   H5   SING  N  N  26  
16F  O6   C6   SING  N  N  27  
16F  C6   H61  SING  N  N  28  
16F  C6   H62  SING  N  N  29  
16F  O6   HO6  SING  N  N  30  
16F  C11  O7   SING  N  N  31  
16F  O7   HO7  SING  N  N  32  
16F  C8   C9   SING  N  N  33  
16F  C8   H8   SING  N  N  34  
16F  C9   C10  DOUB  Y  N  35  
16F  C9   C14  SING  Y  N  36  
16F  C10  C11  SING  Y  N  37  
16F  C10  H10  SING  N  N  38  
16F  C11  C12  DOUB  Y  N  39  
16F  C13  C12  SING  Y  N  40  
16F  C12  H12  SING  N  N  41  
16F  C14  C13  DOUB  Y  N  42  
16F  C13  H13  SING  N  N  43  
16F  C14  H14  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
16F  SMILES            ACDLabs               12.01  "S=C(NC1OC(C(O)C(O)C1O)CO)N/N=C\c2cccc(O)c2"  
16F  SMILES_CANONICAL  CACTVS                3.370  "OC[C@H]1O[C@@H](NC(=S)N\N=C/c2cccc(O)c2)[C@H](O)[C@@H](O)[C@@H]1O"  
16F  SMILES            CACTVS                3.370  "OC[CH]1O[CH](NC(=S)NN=Cc2cccc(O)c2)[CH](O)[CH](O)[CH]1O"  
16F  SMILES_CANONICAL  "OpenEye OEToolkits"  1.7.0  "c1cc(cc(c1)O)/C=N\NC(=S)N[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O"  
16F  SMILES            "OpenEye OEToolkits"  1.7.0  "c1cc(cc(c1)O)C=NNC(=S)NC2C(C(C(C(O2)CO)O)O)O"  
16F  InChI             InChI                 1.03   "InChI=1S/C14H19N3O6S/c18-6-9-10(20)11(21)12(22)13(23-9)16-14(24)17-15-5-7-2-1-3-8(19)4-7/h1-5,9-13,18-22H,6H2,(H2,16,17,24)/b15-5-/t9-,10-,11+,12-,13-/m1/s1"  
16F  InChIKey          InChI                 1.03   FGOQDTKKNPWEBN-ARDSGTFASA-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
16F  "SYSTEMATIC NAME"  ACDLabs               12.01  "N-{[(2Z)-2-(3-hydroxybenzylidene)hydrazinyl]carbothioyl}-beta-D-glucopyranosylamine"  
16F  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.7.0  "1-[(Z)-(3-hydroxyphenyl)methylideneamino]-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]thiourea"  
#   #
loop_
_pdbx_chem_comp_feature.comp_id
_pdbx_chem_comp_feature.type
_pdbx_chem_comp_feature.value
_pdbx_chem_comp_feature.source
_pdbx_chem_comp_feature.support
16F  "CARBOHYDRATE ISOMER"                  D         PDB  ?  
16F  "CARBOHYDRATE RING"                    pyranose  PDB  ?  
16F  "CARBOHYDRATE ANOMER"                  beta      PDB  ?  
16F  "CARBOHYDRATE PRIMARY CARBONYL GROUP"  aldose    PDB  ?  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
16F  "Create component"          2010-04-30  RCSB  
16F  "Modify aromatic_flag"      2011-06-04  RCSB  
16F  "Modify descriptor"         2011-06-04  RCSB  
16F  "Other modification"        2020-07-03  RCSB  
16F  "Modify synonyms"           2020-07-17  RCSB  
16F  "Modify internal type"      2020-07-17  RCSB  
16F  "Modify linking type"       2020-07-17  RCSB  
16F  "Modify atom id"            2020-07-17  RCSB  
16F  "Modify component atom id"  2020-07-17  RCSB  
16F  "Modify leaving atom flag"  2020-07-17  RCSB  
##
