data_GBH
#

_chem_comp.id                                   GBH
_chem_comp.name                                 "2-{4-[2-(beta-D-glucopyranosyloxy)ethyl]piperazin-1-yl}ethanesulfonic acid"
_chem_comp.type                                 D-saccharide
_chem_comp.pdbx_type                            ATOMS
_chem_comp.formula                              "C14 H28 N2 O9 S"
_chem_comp.mon_nstd_parent_comp_id              BGC
_chem_comp.pdbx_synonyms                        
;2-{4-[2-(beta-D-glucosyloxy)ethyl]piperazin-1-yl}ethanesulfonic acid;
2-{4-[2-(D-glucosyloxy)ethyl]piperazin-1-yl}ethanesulfonic acid;
2-{4-[2-(glucosyloxy)ethyl]piperazin-1-yl}ethanesulfonic acid
;

_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2011-10-20
_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                       400.445
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    GBH
_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       3VIM
_chem_comp.pdbx_subcomponent_list               ?
_chem_comp.pdbx_processing_site                 PDBJ
#   #
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  GBH  "2-{4-[2-(beta-D-glucosyloxy)ethyl]piperazin-1-yl}ethanesulfonic acid"  PDB  ?  
2  GBH  "2-{4-[2-(D-glucosyloxy)ethyl]piperazin-1-yl}ethanesulfonic acid"       PDB  ?  
3  GBH  "2-{4-[2-(glucosyloxy)ethyl]piperazin-1-yl}ethanesulfonic acid"         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
GBH  C1    C1    C  0  1  N  N  R  -26.967  82.656  14.672   3.309   0.024  -0.105  C1    GBH   1  
GBH  O1    O1    O  0  1  N  N  N  -27.035  83.152  13.353   2.146  -0.539   0.505  O1    GBH   2  
GBH  C2    C2    C  0  1  N  N  R  -28.403  82.606  15.182   3.525   1.445   0.422  C2    GBH   3  
GBH  O2    O2    O  0  1  N  N  N  -28.784  83.922  15.593   2.412   2.264   0.056  O2    GBH   4  
GBH  C3    C3    C  0  1  N  N  S  -28.633  81.591  16.300   4.806   2.019  -0.191  C3    GBH   5  
GBH  O3    O3    O  0  1  N  N  N  -30.058  81.458  16.435   5.055   3.317   0.352  O3    GBH   6  
GBH  C4    C4    C  0  1  N  N  S  -27.965  80.268  15.932   5.978   1.091   0.142  C4    GBH   7  
GBH  O4    O4    O  0  1  N  N  N  -28.199  79.323  16.976   7.166   1.578  -0.485  O4    GBH   8  
GBH  C5    C5    C  0  1  N  N  R  -26.478  80.554  15.731   5.668  -0.317  -0.373  C5    GBH   9  
GBH  O5    O5    O  0  1  N  N  N  -26.396  81.352  14.555   4.448  -0.779   0.211  O5    GBH  10  
GBH  C6    C6    C  0  1  N  N  N  -25.614  79.332  15.477   6.807  -1.263   0.008  C6    GBH  11  
GBH  O6    O6    O  0  1  N  N  N  -25.866  78.914  14.136   6.574  -2.548  -0.572  O6    GBH  12  
GBH  OAA   OAA   O  0  1  N  N  N  -26.097  78.504   4.618  -6.752   2.055   0.261  OAA   GBH  13  
GBH  OAB   OAB   O  0  1  N  N  N  -27.580  77.180   6.035  -8.131   0.271   0.824  OAB   GBH  14  
GBH  OAG   OAG   O  0  1  N  N  N  -25.321  76.439   5.567  -7.534   0.414  -1.418  OAG   GBH  15  
GBH  CAI   CAI   C  0  1  N  N  N  -25.836  83.714  12.840   1.788  -1.826  -0.002  CAI   GBH  16  
GBH  CAJ   CAJ   C  0  1  N  N  N  -24.995  82.637  12.184   0.536  -2.329   0.719  CAJ   GBH  17  
GBH  CAK   CAK   C  0  1  N  N  N  -26.016  82.533   9.906  -1.099  -1.723  -0.962  CAK   GBH  18  
GBH  CAL   CAL   C  0  1  N  N  N  -24.793  80.755  10.817  -1.675  -1.599   1.386  CAL   GBH  19  
GBH  CAM   CAM   C  0  1  N  N  N  -26.658  81.553   8.919  -2.227  -0.741  -1.290  CAM   GBH  20  
GBH  CAN   CAN   C  0  1  N  N  N  -25.380  79.761   9.825  -2.802  -0.617   1.058  CAN   GBH  21  
GBH  CAO   CAO   C  0  1  N  N  N  -26.477  79.504   7.684  -4.438  -0.011  -0.622  CAO   GBH  22  
GBH  CAP   CAP   C  0  1  N  N  N  -25.545  78.437   7.114  -5.625  -0.364   0.276  CAP   GBH  23  
GBH  NAX   NAX   N  0  1  N  N  N  -25.719  81.842  11.162  -0.600  -1.455   0.394  NAX   GBH  24  
GBH  NAY   NAY   N  0  1  N  N  N  -25.755  80.432   8.574  -3.302  -0.884  -0.298  NAY   GBH  25  
GBH  SAZ   SAZ   S  0  1  N  N  N  -26.180  77.624   5.800  -7.027   0.715  -0.124  SAZ   GBH  26  
GBH  H1    H1    H  0  1  N  N  N  -26.366  83.261  15.367   3.174   0.054  -1.186  H1    GBH  27  
GBH  H2    H2    H  0  1  N  N  N  -29.038  82.257  14.354   3.618   1.421   1.508  H2    GBH  28  
GBH  HO2   HO2   H  0  1  N  Y  N  -29.678  83.908  15.914   1.565   1.956   0.407  HO2   GBH  29  
GBH  H3    H3    H  0  1  N  N  N  -28.194  81.911  17.256   4.693   2.091  -1.272  H3    GBH  30  
GBH  HO3   HO3   H  0  1  N  Y  N  -30.254  80.833  17.123   4.349   3.956   0.184  HO3   GBH  31  
GBH  H4    H4    H  0  1  N  N  N  -28.375  79.837  15.007   6.123   1.060   1.222  H4    GBH  32  
GBH  HO4   HO4   H  0  1  N  Y  N  -27.786  78.497  16.754   7.421   2.469  -0.208  HO4   GBH  33  
GBH  H5    H5    H  0  1  N  N  N  -26.106  81.018  16.656   5.564  -0.291  -1.458  H5    GBH  34  
GBH  H61   H6    H  0  1  N  N  N  -24.551  79.583  15.605   7.751  -0.863  -0.362  H61   GBH  35  
GBH  H62   H6A   H  0  1  N  N  N  -25.873  78.528  16.182   6.853  -1.358   1.093  H62   GBH  36  
GBH  HO6   HO6   H  0  1  N  Y  N  -25.341  78.147  13.939   7.259  -3.201  -0.371  HO6   GBH  37  
GBH  HOAB  HOAB  H  0  0  N  N  N  -27.625  76.232   5.986  -8.957   0.765   0.726  HOAB  GBH  38  
GBH  HAI   HAI   H  0  1  N  N  N  -26.086  84.484  12.095   1.587  -1.752  -1.071  HAI   GBH  39  
GBH  HAIA  HAIA  H  0  0  N  N  N  -25.266  84.168  13.664   2.609  -2.524   0.166  HAIA  GBH  40  
GBH  HAJ   HAJ   H  0  1  N  N  N  -24.142  83.126  11.691   0.315  -3.346   0.397  HAJ   GBH  41  
GBH  HAJA  HAJA  H  0  0  N  N  N  -24.653  81.948  12.970   0.707  -2.317   1.795  HAJA  GBH  42  
GBH  HAK   HAK   H  0  1  N  N  N  -25.083  82.927   9.476  -1.479  -2.743  -1.015  HAK   GBH  43  
GBH  HAKA  HAKA  H  0  0  N  N  N  -26.711  83.363  10.101  -0.289  -1.598  -1.679  HAKA  GBH  44  
GBH  HAL   HAL   H  0  1  N  N  N  -24.539  80.212  11.740  -1.283  -1.383   2.381  HAL   GBH  45  
GBH  HALA  HALA  H  0  0  N  N  N  -23.892  81.199  10.368  -2.060  -2.618   1.360  HALA  GBH  46  
GBH  HAM   HAM   H  0  1  N  N  N  -27.569  81.140   9.378  -1.841   0.278  -1.263  HAM   GBH  47  
GBH  HAMA  HAMA  H  0  0  N  N  N  -26.907  82.098   7.997  -2.619  -0.956  -2.284  HAMA  GBH  48  
GBH  HAN   HAN   H  0  1  N  N  N  -24.629  78.987   9.606  -3.613  -0.742   1.776  HAN   GBH  49  
GBH  HANA  HANA  H  0  0  N  N  N  -26.276  79.300  10.267  -2.423   0.403   1.111  HANA  GBH  50  
GBH  HAO   HAO   H  0  1  N  N  N  -26.911  80.077   6.851  -4.717  -0.151  -1.666  HAO   GBH  51  
GBH  HAOA  HAOA  H  0  0  N  N  N  -27.273  79.009   8.259  -4.154   1.029  -0.458  HAOA  GBH  52  
GBH  HAP   HAP   H  0  1  N  N  N  -24.616  78.931   6.794  -5.908  -1.403   0.112  HAP   GBH  53  
GBH  HAPA  HAPA  H  0  0  N  N  N  -25.343  77.701   7.906  -5.345  -0.223   1.320  HAPA  GBH  54  
#   #
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
GBH  C1   O1    SING  N  N   1  
GBH  C1   C2    SING  N  N   2  
GBH  C1   O5    SING  N  N   3  
GBH  O1   CAI   SING  N  N   4  
GBH  C2   O2    SING  N  N   5  
GBH  C2   C3    SING  N  N   6  
GBH  C3   O3    SING  N  N   7  
GBH  C3   C4    SING  N  N   8  
GBH  C4   O4    SING  N  N   9  
GBH  C4   C5    SING  N  N  10  
GBH  C5   O5    SING  N  N  11  
GBH  C5   C6    SING  N  N  12  
GBH  C6   O6    SING  N  N  13  
GBH  OAA  SAZ   DOUB  N  N  14  
GBH  OAB  SAZ   SING  N  N  15  
GBH  OAG  SAZ   DOUB  N  N  16  
GBH  CAI  CAJ   SING  N  N  17  
GBH  CAJ  NAX   SING  N  N  18  
GBH  CAK  CAM   SING  N  N  19  
GBH  CAK  NAX   SING  N  N  20  
GBH  CAL  CAN   SING  N  N  21  
GBH  CAL  NAX   SING  N  N  22  
GBH  CAM  NAY   SING  N  N  23  
GBH  CAN  NAY   SING  N  N  24  
GBH  CAO  CAP   SING  N  N  25  
GBH  CAO  NAY   SING  N  N  26  
GBH  CAP  SAZ   SING  N  N  27  
GBH  C1   H1    SING  N  N  28  
GBH  C2   H2    SING  N  N  29  
GBH  O2   HO2   SING  N  N  30  
GBH  C3   H3    SING  N  N  31  
GBH  O3   HO3   SING  N  N  32  
GBH  C4   H4    SING  N  N  33  
GBH  O4   HO4   SING  N  N  34  
GBH  C5   H5    SING  N  N  35  
GBH  C6   H61   SING  N  N  36  
GBH  C6   H62   SING  N  N  37  
GBH  O6   HO6   SING  N  N  38  
GBH  OAB  HOAB  SING  N  N  39  
GBH  CAI  HAI   SING  N  N  40  
GBH  CAI  HAIA  SING  N  N  41  
GBH  CAJ  HAJ   SING  N  N  42  
GBH  CAJ  HAJA  SING  N  N  43  
GBH  CAK  HAK   SING  N  N  44  
GBH  CAK  HAKA  SING  N  N  45  
GBH  CAL  HAL   SING  N  N  46  
GBH  CAL  HALA  SING  N  N  47  
GBH  CAM  HAM   SING  N  N  48  
GBH  CAM  HAMA  SING  N  N  49  
GBH  CAN  HAN   SING  N  N  50  
GBH  CAN  HANA  SING  N  N  51  
GBH  CAO  HAO   SING  N  N  52  
GBH  CAO  HAOA  SING  N  N  53  
GBH  CAP  HAP   SING  N  N  54  
GBH  CAP  HAPA  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
GBH  SMILES            ACDLabs               12.01  "O=S(=O)(O)CCN2CCN(CCOC1OC(C(O)C(O)C1O)CO)CC2"  
GBH  InChI             InChI                 1.03   "InChI=1S/C14H28N2O9S/c17-9-10-11(18)12(19)13(20)14(25-10)24-7-5-15-1-3-16(4-2-15)6-8-26(21,22)23/h10-14,17-20H,1-9H2,(H,21,22,23)/t10-,11-,12+,13-,14-/m1/s1"  
GBH  InChIKey          InChI                 1.03   RRNQQJMHWBFGHX-RKQHYHRCSA-N  
GBH  SMILES_CANONICAL  CACTVS                3.370  "OC[C@H]1O[C@@H](OCCN2CCN(CC2)CC[S](O)(=O)=O)[C@H](O)[C@@H](O)[C@@H]1O"  
GBH  SMILES            CACTVS                3.370  "OC[CH]1O[CH](OCCN2CCN(CC2)CC[S](O)(=O)=O)[CH](O)[CH](O)[CH]1O"  
GBH  SMILES_CANONICAL  "OpenEye OEToolkits"  1.7.2  "C1CN(CCN1CCO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)CCS(=O)(=O)O"  
GBH  SMILES            "OpenEye OEToolkits"  1.7.2  "C1CN(CCN1CCOC2C(C(C(C(O2)CO)O)O)O)CCS(=O)(=O)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
GBH  "SYSTEMATIC NAME"  ACDLabs               12.01  "2-{4-[2-(beta-D-glucopyranosyloxy)ethyl]piperazin-1-yl}ethanesulfonic acid"  
GBH  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.7.2  "2-[4-[2-[(2R,3R,4S,5S,6R)-6-(hydroxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]oxyethyl]piperazin-1-yl]ethanesulfonic acid"  
#
_pdbx_chem_comp_related.comp_id            GBH
_pdbx_chem_comp_related.related_comp_id    BGC
_pdbx_chem_comp_related.relationship_type  "Carbohydrate core"
_pdbx_chem_comp_related.details            ?
#   #
loop_
_pdbx_chem_comp_atom_related.ordinal
_pdbx_chem_comp_atom_related.comp_id
_pdbx_chem_comp_atom_related.atom_id
_pdbx_chem_comp_atom_related.related_comp_id
_pdbx_chem_comp_atom_related.related_atom_id
_pdbx_chem_comp_atom_related.related_type
 1  GBH  C1   BGC  C1   "Carbohydrate core"  
 2  GBH  C2   BGC  C2   "Carbohydrate core"  
 3  GBH  C3   BGC  C3   "Carbohydrate core"  
 4  GBH  C4   BGC  C4   "Carbohydrate core"  
 5  GBH  C5   BGC  C5   "Carbohydrate core"  
 6  GBH  C6   BGC  C6   "Carbohydrate core"  
 7  GBH  O1   BGC  O1   "Carbohydrate core"  
 8  GBH  O2   BGC  O2   "Carbohydrate core"  
 9  GBH  O3   BGC  O3   "Carbohydrate core"  
10  GBH  O4   BGC  O4   "Carbohydrate core"  
11  GBH  O5   BGC  O5   "Carbohydrate core"  
12  GBH  O6   BGC  O6   "Carbohydrate core"  
13  GBH  H1   BGC  H1   "Carbohydrate core"  
14  GBH  H2   BGC  H2   "Carbohydrate core"  
15  GBH  H3   BGC  H3   "Carbohydrate core"  
16  GBH  H4   BGC  H4   "Carbohydrate core"  
17  GBH  H5   BGC  H5   "Carbohydrate core"  
18  GBH  H61  BGC  H61  "Carbohydrate core"  
19  GBH  H62  BGC  H62  "Carbohydrate core"  
20  GBH  HO2  BGC  HO2  "Carbohydrate core"  
21  GBH  HO3  BGC  HO3  "Carbohydrate core"  
22  GBH  HO4  BGC  HO4  "Carbohydrate core"  
23  GBH  HO6  BGC  HO6  "Carbohydrate core"  
#   #
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
GBH  "CARBOHYDRATE ISOMER"                  D         PDB  ?  
GBH  "CARBOHYDRATE RING"                    pyranose  PDB  ?  
GBH  "CARBOHYDRATE ANOMER"                  beta      PDB  ?  
GBH  "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
GBH  "Create component"          2011-10-20  PDBJ  
GBH  "Other modification"        2020-07-03  RCSB  
GBH  "Modify parent residue"     2020-07-17  RCSB  
GBH  "Modify synonyms"           2020-07-17  RCSB  
GBH  "Modify internal type"      2020-07-17  RCSB  
GBH  "Modify linking type"       2020-07-17  RCSB  
GBH  "Modify atom id"            2020-07-17  RCSB  
GBH  "Modify component atom id"  2020-07-17  RCSB  
GBH  "Modify leaving atom flag"  2020-07-17  RCSB  
##
