data_QUG
#

_chem_comp.id                                   QUG
_chem_comp.name                                 "2-amino-5-({[(1S,4S,5S)-4,5-dihydroxycyclopent-2-en-1-yl]amino}methyl)-1,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C12 H15 N5 O3"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        Queuine
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2019-06-06
_chem_comp.pdbx_modified_date                   2020-06-17
_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                       277.279
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    QUG
_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       6P78
_chem_comp.pdbx_subcomponent_list               ?
_chem_comp.pdbx_processing_site                 RCSB
#   #
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
QUG  N    N1   N  0  1  N  N  N   3.354  43.776  74.638  -3.166  -1.712   0.019  N    QUG   1  
QUG  C    C1   C  0  1  N  N  N   2.144  44.094  75.149  -4.200  -0.998  -0.370  C    QUG   2  
QUG  O    O1   O  0  1  N  N  N   6.475  40.855  71.094   3.070   0.373  -1.999  O    QUG   3  
QUG  C1   C2   C  0  1  N  N  N   3.657  42.542  74.208  -2.012  -1.128   0.380  C1   QUG   4  
QUG  C10  C3   C  0  1  N  N  N   6.013  37.494  70.380   3.959  -1.620   0.314  C10  QUG   5  
QUG  C11  C4   C  0  1  N  N  N   3.522  39.155  73.490   0.508   1.030   1.123  C11  QUG   6  
QUG  C2   C5   C  0  1  Y  N  N   2.609  41.509  74.359  -1.926   0.333   0.333  C2   QUG   7  
QUG  C3   C6   C  0  1  Y  N  N   1.309  41.908  74.928  -3.041   1.054  -0.085  C3   QUG   8  
QUG  C4   C7   C  0  1  Y  N  N   1.189  39.739  74.465  -1.423   2.524   0.388  C4   QUG   9  
QUG  C5   C8   C  0  1  Y  N  N   2.480  40.079  74.075  -0.888   1.315   0.633  C5   QUG  10  
QUG  C6   C9   C  0  1  N  N  S   7.045  38.600  70.366   4.734  -0.590  -0.474  C6   QUG  11  
QUG  C7   C10  C  0  1  N  N  S   6.671  39.507  71.532   3.719   0.547  -0.738  C7   QUG  12  
QUG  C8   C11  C  0  1  N  N  S   5.455  38.871  72.215   2.726   0.347   0.430  C8   QUG  13  
QUG  C9   C12  C  0  1  N  N  N   5.146  37.637  71.385   2.864  -1.109   0.807  C9   QUG  14  
QUG  N1   N2   N  0  1  N  N  N   1.123  43.200  75.301  -4.174   0.358  -0.434  N1   QUG  15  
QUG  N2   N3   N  0  1  Y  N  N   0.528  40.819  74.952  -2.716   2.370  -0.044  N2   QUG  16  
QUG  N3   N4   N  0  1  N  N  N   4.278  39.763  72.378   1.354   0.634  -0.011  N3   QUG  17  
QUG  N4   N5   N  0  1  N  N  N   1.933  45.384  75.527  -5.350  -1.649  -0.727  N4   QUG  18  
QUG  O1   O2   O  0  1  N  N  N   8.354  38.105  70.658   5.838  -0.104   0.292  O1   QUG  19  
QUG  O2   O3   O  0  1  N  N  N   4.782  42.280  73.742  -1.058  -1.798   0.741  O2   QUG  20  
QUG  H1   H1   H  0  1  N  N  N   6.243  41.399  71.837   3.671   0.390  -2.756  H1   QUG  21  
QUG  H2   H2   H  0  1  N  N  N   5.981  36.686  69.664   4.269  -2.646   0.448  H2   QUG  22  
QUG  H3   H3   H  0  1  N  N  N   3.018  38.251  73.117   0.920   1.926   1.588  H3   QUG  23  
QUG  H4   H4   H  0  1  N  N  N   4.230  38.879  74.285   0.479   0.222   1.855  H4   QUG  24  
QUG  H5   H5   H  0  1  N  N  N   0.769  38.747  74.390  -0.915   3.468   0.511  H5   QUG  25  
QUG  H6   H6   H  0  1  N  N  N   7.013  39.154  69.416   5.083  -1.015  -1.415  H6   QUG  26  
QUG  H7   H7   H  0  1  N  N  N   7.503  39.485  72.251   4.201   1.523  -0.679  H7   QUG  27  
QUG  H8   H8   H  0  1  N  N  N   5.772  38.534  73.213   2.994   0.987   1.271  H8   QUG  28  
QUG  H9   H9   H  0  1  N  N  N   4.328  36.960  71.583   2.149  -1.657   1.403  H9   QUG  29  
QUG  H10  H10  H  0  1  N  N  N   0.247  43.494  75.683  -4.963   0.841  -0.728  H10  QUG  30  
QUG  H11  H11  H  0  1  N  N  N  -0.415  40.805  75.284  -3.311   3.097  -0.285  H11  QUG  31  
QUG  H12  H12  H  0  1  N  N  N   4.565  40.692  72.610   1.345   1.339  -0.732  H12  QUG  32  
QUG  H14  H14  H  0  1  N  N  N   2.661  46.061  75.423  -5.391  -2.618  -0.690  H14  QUG  33  
QUG  H15  H15  H  0  1  N  N  N   1.050  45.655  75.909  -6.124  -1.142  -1.017  H15  QUG  34  
QUG  H16  H16  H  0  1  N  N  N   8.976  38.823  70.641   6.482  -0.785   0.530  H16  QUG  35  
#   #
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
QUG  C6   C10  SING  N  N   1  
QUG  C6   O1   SING  N  N   2  
QUG  C6   C7   SING  N  N   3  
QUG  C10  C9   DOUB  N  N   4  
QUG  O    C7   SING  N  N   5  
QUG  C9   C8   SING  N  N   6  
QUG  C7   C8   SING  N  N   7  
QUG  C8   N3   SING  N  N   8  
QUG  N3   C11  SING  N  N   9  
QUG  C11  C5   SING  N  N  10  
QUG  O2   C1   DOUB  N  N  11  
QUG  C5   C2   SING  Y  N  12  
QUG  C5   C4   DOUB  Y  N  13  
QUG  C1   C2   SING  N  N  14  
QUG  C1   N    SING  N  N  15  
QUG  C2   C3   DOUB  Y  N  16  
QUG  C4   N2   SING  Y  N  17  
QUG  N    C    DOUB  N  N  18  
QUG  C3   N2   SING  Y  N  19  
QUG  C3   N1   SING  N  N  20  
QUG  C    N1   SING  N  N  21  
QUG  C    N4   SING  N  N  22  
QUG  O    H1   SING  N  N  23  
QUG  C10  H2   SING  N  N  24  
QUG  C11  H3   SING  N  N  25  
QUG  C11  H4   SING  N  N  26  
QUG  C4   H5   SING  N  N  27  
QUG  C6   H6   SING  N  N  28  
QUG  C7   H7   SING  N  N  29  
QUG  C8   H8   SING  N  N  30  
QUG  C9   H9   SING  N  N  31  
QUG  N1   H10  SING  N  N  32  
QUG  N2   H11  SING  N  N  33  
QUG  N3   H12  SING  N  N  34  
QUG  N4   H14  SING  N  N  35  
QUG  N4   H15  SING  N  N  36  
QUG  O1   H16  SING  N  N  37  
#   #
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
QUG  SMILES            ACDLabs               12.01  "N1=C(Nc3c(C1=O)c(CNC2C(O)C(C=C2)O)cn3)N"  
QUG  InChI             InChI                 1.03   "InChI=1S/C12H15N5O3/c13-12-16-10-8(11(20)17-12)5(4-15-10)3-14-6-1-2-7(18)9(6)19/h1-2,4,6-7,9,14,18-19H,3H2,(H4,13,15,16,17,20)/t6-,7-,9-/m0/s1"  
QUG  InChIKey          InChI                 1.03   WYROLENTHWJFLR-ZKWXMUAHSA-N  
QUG  SMILES_CANONICAL  CACTVS                3.385  "NC1=NC(=O)c2c(CN[C@H]3C=C[C@H](O)[C@H]3O)c[nH]c2N1"  
QUG  SMILES            CACTVS                3.385  "NC1=NC(=O)c2c(CN[CH]3C=C[CH](O)[CH]3O)c[nH]c2N1"  
QUG  SMILES_CANONICAL  "OpenEye OEToolkits"  2.0.7  "c1c(c2c([nH]1)NC(=NC2=O)N)CN[C@H]3C=C[C@@H]([C@H]3O)O"  
QUG  SMILES            "OpenEye OEToolkits"  2.0.7  "c1c(c2c([nH]1)NC(=NC2=O)N)CNC3C=CC(C3O)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
QUG  "SYSTEMATIC NAME"  ACDLabs               12.01  "2-amino-5-({[(1S,4S,5S)-4,5-dihydroxycyclopent-2-en-1-yl]amino}methyl)-1,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one"  
QUG  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  2.0.7  "2-azanyl-5-[[[(1~{S},4~{S},5~{S})-4,5-bis(oxidanyl)cyclopent-2-en-1-yl]amino]methyl]-1,7-dihydropyrrolo[2,3-d]pyrimidin-4-one"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
QUG  "Create component"  2019-06-06  RCSB  
QUG  "Initial release"   2019-09-18  RCSB  
QUG  "Modify synonyms"   2020-06-05  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     QUG
_pdbx_chem_comp_synonyms.name        Queuine
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
