data_GPQ
#

_chem_comp.id                                   GPQ
_chem_comp.name                                 "5-chloro-1-(beta-D-glucopyranosyl)pyrimidine-2,4(1H,3H)-dione"
_chem_comp.type                                 D-saccharide
_chem_comp.pdbx_type                            ATOMS
_chem_comp.formula                              "C10 H13 Cl N2 O7"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        
;5-chloro-1-(beta-D-glucosyl)pyrimidine-2,4(1H,3H)-dione; 5-chloro-1-(D-glucosyl)pyrimidine-2,4(1H,3H)-dione;
5-chloro-1-(glucosyl)pyrimidine-2,4(1H,3H)-dione
;

_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2011-08-10
_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                       308.672
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    GPQ
_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       3T3E
_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  GPQ  "5-chloro-1-(beta-D-glucosyl)pyrimidine-2,4(1H,3H)-dione"  PDB  ?  
2  GPQ  "5-chloro-1-(D-glucosyl)pyrimidine-2,4(1H,3H)-dione"       PDB  ?  
3  GPQ  "5-chloro-1-(glucosyl)pyrimidine-2,4(1H,3H)-dione"         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
GPQ  N1   N1      N   0  1  N  N  N  34.091  23.415  28.762   0.832   0.228   0.545  N1   GPQ   1  
GPQ  CL1  CL1     CL  0  1  N  N  N  37.941  23.947  29.641   3.550  -0.994  -2.062  CL1  GPQ   2  
GPQ  C2A  C2      C   0  1  N  N  N  33.418  24.141  29.751   1.575   0.621   1.595  C2A  GPQ   3  
GPQ  O2A  O2      O   0  1  N  N  N  32.199  24.199  29.753   1.025   1.059   2.587  O2A  GPQ   4  
GPQ  N3   N3      N   0  1  N  N  N  34.132  24.845  30.682   2.918   0.534   1.565  N3   GPQ   5  
GPQ  C4A  C4      C   0  1  N  N  N  35.529  24.818  30.656   3.543   0.050   0.473  C4A  GPQ   6  
GPQ  O4A  O4      O   0  1  N  N  N  36.090  25.483  31.509   4.758  -0.029   0.444  O4A  GPQ   7  
GPQ  C5A  C5      C   0  1  N  N  N  36.217  24.077  29.687   2.773  -0.367  -0.641  C5A  GPQ   8  
GPQ  C6A  C6      C   0  1  N  N  N  35.496  23.380  28.735   1.428  -0.270  -0.583  C6A  GPQ   9  
GPQ  C1   "C1'"   C   0  1  N  N  R  33.268  22.726  27.804  -0.628   0.327   0.611  C1   GPQ  10  
GPQ  C2   "C2'"   C   0  1  N  N  R  33.695  23.039  26.337  -1.118   1.343  -0.426  C2   GPQ  11  
GPQ  O2   "O2'"   O   0  1  N  N  N  33.820  24.452  26.169  -0.587   2.633  -0.117  O2   GPQ  12  
GPQ  C3   "C3'"   C   0  1  N  N  S  32.637  22.405  25.390  -2.648   1.397  -0.392  C3   GPQ  13  
GPQ  O3   "O3'"   O   0  1  N  N  N  33.068  22.343  24.041  -3.117   2.288  -1.406  O3   GPQ  14  
GPQ  C4   "C4'"   C   0  1  N  N  S  32.368  20.953  25.846  -3.204  -0.007  -0.647  C4   GPQ  15  
GPQ  O4   "O4'"   O   0  1  N  N  N  31.290  20.479  25.090  -4.629   0.017  -0.546  O4   GPQ  16  
GPQ  C5   "C5'"   C   0  1  N  N  R  32.065  20.799  27.369  -2.634  -0.971   0.398  C5   GPQ  17  
GPQ  O5   "O5'"   O   0  1  N  N  N  33.199  21.288  28.089  -1.206  -0.950   0.334  O5   GPQ  18  
GPQ  C6   "C6'"   C   0  1  N  N  N  32.050  19.352  27.805  -3.136  -2.387   0.113  C6   GPQ  19  
GPQ  O6   "O6'"   O   0  1  N  N  N  33.208  18.656  27.304  -2.700  -3.265   1.153  O6   GPQ  20  
GPQ  HN3  HN3     H   0  1  N  N  N  33.655  25.378  31.380   3.438   0.822   2.331  HN3  GPQ  21  
GPQ  H6   H6      H   0  1  N  N  N  36.010  22.811  27.974   0.824  -0.584  -1.423  H6   GPQ  22  
GPQ  H1   "H1'"   H   0  1  N  N  N  32.243  23.111  27.907  -0.926   0.653   1.607  H1   GPQ  23  
GPQ  H2   "H2'"   H   0  1  N  N  N  34.677  22.607  26.094  -0.785   1.040  -1.418  H2   GPQ  24  
GPQ  HO2  "HO2'"  H   0  1  N  Y  N  34.080  24.643  25.276  -0.857   3.327  -0.734  HO2  GPQ  25  
GPQ  H3   "H3'"   H   0  1  N  N  N  31.741  23.041  25.443  -2.979   1.750   0.585  H3   GPQ  26  
GPQ  HO3  "HO3'"  H   0  1  N  Y  N  32.387  21.949  23.508  -4.080   2.371  -1.442  HO3  GPQ  27  
GPQ  H4   "H4'"   H   0  1  N  N  N  33.286  20.370  25.683  -2.915  -0.338  -1.645  H4   GPQ  28  
GPQ  HO4  "HO4'"  H   0  1  N  Y  N  31.094  19.585  25.343  -5.057   0.612  -1.177  HO4  GPQ  29  
GPQ  H5   "H5'"   H   0  1  N  N  N  31.106  21.306  27.549  -2.958  -0.662   1.391  H5   GPQ  30  
GPQ  H61  "H6'"   H   0  1  N  N  N  32.052  19.308  28.904  -4.226  -2.385   0.073  H61  GPQ  31  
GPQ  H62  "H6'A"  H   0  1  N  N  N  31.143  18.868  27.413  -2.738  -2.730  -0.842  H62  GPQ  32  
GPQ  HO6  "HO6'"  H   0  1  N  Y  N  33.181  17.750  27.588  -2.983  -4.182   1.038  HO6  GPQ  33  
#   #
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
GPQ  N1   C2A  SING  N  N   1  
GPQ  N1   C6A  SING  N  N   2  
GPQ  N1   C1   SING  N  N   3  
GPQ  CL1  C5A  SING  N  N   4  
GPQ  C2A  O2A  DOUB  N  N   5  
GPQ  C2A  N3   SING  N  N   6  
GPQ  N3   C4A  SING  N  N   7  
GPQ  C4A  O4A  DOUB  N  N   8  
GPQ  C4A  C5A  SING  N  N   9  
GPQ  C5A  C6A  DOUB  N  N  10  
GPQ  C1   C2   SING  N  N  11  
GPQ  C1   O5   SING  N  N  12  
GPQ  C2   O2   SING  N  N  13  
GPQ  C2   C3   SING  N  N  14  
GPQ  C3   O3   SING  N  N  15  
GPQ  C3   C4   SING  N  N  16  
GPQ  C4   O4   SING  N  N  17  
GPQ  C4   C5   SING  N  N  18  
GPQ  C5   O5   SING  N  N  19  
GPQ  C5   C6   SING  N  N  20  
GPQ  C6   O6   SING  N  N  21  
GPQ  N3   HN3  SING  N  N  22  
GPQ  C6A  H6   SING  N  N  23  
GPQ  C1   H1   SING  N  N  24  
GPQ  C2   H2   SING  N  N  25  
GPQ  O2   HO2  SING  N  N  26  
GPQ  C3   H3   SING  N  N  27  
GPQ  O3   HO3  SING  N  N  28  
GPQ  C4   H4   SING  N  N  29  
GPQ  O4   HO4  SING  N  N  30  
GPQ  C5   H5   SING  N  N  31  
GPQ  C6   H61  SING  N  N  32  
GPQ  C6   H62  SING  N  N  33  
GPQ  O6   HO6  SING  N  N  34  
#   #
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
GPQ  SMILES            ACDLabs               12.01  "ClC1=CN(C(=O)NC1=O)C2OC(C(O)C(O)C2O)CO"  
GPQ  InChI             InChI                 1.03   "InChI=1S/C10H13ClN2O7/c11-3-1-13(10(19)12-8(3)18)9-7(17)6(16)5(15)4(2-14)20-9/h1,4-7,9,14-17H,2H2,(H,12,18,19)/t4-,5-,6+,7-,9-/m1/s1"  
GPQ  InChIKey          InChI                 1.03   NONSBAHWXCNSII-XSEHCYKFSA-N  
GPQ  SMILES_CANONICAL  CACTVS                3.370  "OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)N2C=C(Cl)C(=O)NC2=O"  
GPQ  SMILES            CACTVS                3.370  "OC[CH]1O[CH]([CH](O)[CH](O)[CH]1O)N2C=C(Cl)C(=O)NC2=O"  
GPQ  SMILES_CANONICAL  "OpenEye OEToolkits"  1.7.2  "C1=C(C(=O)NC(=O)N1[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)Cl"  
GPQ  SMILES            "OpenEye OEToolkits"  1.7.2  "C1=C(C(=O)NC(=O)N1C2C(C(C(C(O2)CO)O)O)O)Cl"  
#   #
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
GPQ  "SYSTEMATIC NAME"  ACDLabs               12.01  "5-chloro-1-(beta-D-glucopyranosyl)pyrimidine-2,4(1H,3H)-dione"  
GPQ  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.7.2  "5-chloranyl-1-[(2R,3R,4S,5S,6R)-6-(hydroxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]pyrimidine-2,4-dione"  
#   #
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
GPQ  "CARBOHYDRATE ISOMER"                  D         PDB  ?  
GPQ  "CARBOHYDRATE RING"                    pyranose  PDB  ?  
GPQ  "CARBOHYDRATE ANOMER"                  beta      PDB  ?  
GPQ  "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
GPQ  "Create component"          2011-08-10  RCSB  
GPQ  "Other modification"        2020-07-03  RCSB  
GPQ  "Modify synonyms"           2020-07-17  RCSB  
GPQ  "Modify internal type"      2020-07-17  RCSB  
GPQ  "Modify linking type"       2020-07-17  RCSB  
GPQ  "Modify atom id"            2020-07-17  RCSB  
GPQ  "Modify component atom id"  2020-07-17  RCSB  
GPQ  "Modify leaving atom flag"  2020-07-17  RCSB  
##
