data_QEI
# 
_chem_comp.id                                    QEI 
_chem_comp.name                                  2-amino-5-({[(1S,4S,5R)-4,5-dihydroxycyclopent-2-en-1-yl]amino}methyl)-3,7-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                     2007-12-13 
_chem_comp.pdbx_modified_date                    2008-12-12 
_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                     QEI 
_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        3BLO 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBJ 
# 
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 
QEI C1   C1   C 0 1 N N S 20.658 21.127 19.044 -2.657 -0.148 0.313  C1   QEI 1  
QEI C2   C2   C 0 1 N N R 20.767 22.444 19.859 -3.638 -0.342 -0.865 C2   QEI 2  
QEI C3   C3   C 0 1 N N N 19.680 21.522 17.952 -2.747 1.323  0.650  C3   QEI 3  
QEI C4   C4   C 0 1 N N S 19.636 23.353 19.392 -4.614 0.839  -0.649 C4   QEI 4  
QEI C5   C5   C 0 1 N N N 19.177 22.743 18.094 -3.814 1.861  0.125  C5   QEI 5  
QEI C6   C6   C 0 1 N N N 20.202 18.509 19.521 -0.478 -0.893 1.062  C6   QEI 6  
QEI C9   C9   C 0 1 Y N N 18.040 18.015 20.877 1.992  -0.305 0.295  C9   QEI 7  
QEI C10  C10  C 0 1 Y N N 16.704 17.700 20.413 3.094  -1.084 -0.086 C10  QEI 8  
QEI C11  C11  C 0 1 N N N 18.283 18.081 22.320 2.116  1.101  0.304  C11  QEI 9  
QEI O1   O1   O 0 1 N N N 21.986 23.141 19.597 -4.319 -1.594 -0.766 O1   QEI 10 
QEI O2   O2   O 0 1 N N N 20.158 24.644 19.166 -5.747 0.415  0.110  O2   QEI 11 
QEI N1   N1   N 0 1 N N N 20.022 19.991 19.791 -1.290 -0.496 -0.096 N1   QEI 12 
QEI C7   C7   C 0 1 Y N N 18.776 18.177 19.637 0.914  -1.243 0.604  C7   QEI 13 
QEI C8   C8   C 0 1 Y N N 17.907 17.967 18.575 1.405  -2.477 0.400  C8   QEI 14 
QEI N2   N2   N 0 1 Y N N 16.693 17.688 19.056 2.713  -2.391 -0.008 N2   QEI 15 
QEI N3   N3   N 0 1 N N N 15.778 17.490 21.376 4.237  -0.473 -0.433 N3   QEI 16 
QEI C12  C12  C 0 1 N N N 16.041 17.566 22.691 4.340  0.836  -0.421 C12  QEI 17 
QEI N5   N5   N 0 1 N N N 14.949 17.926 23.415 5.531  1.412  -0.785 N5   QEI 18 
QEI N4   N4   N 0 1 N N N 17.278 17.857 23.159 3.301  1.642  -0.059 N4   QEI 19 
QEI O3   O3   O 0 1 N N N 19.382 18.338 22.748 1.179  1.810  0.629  O3   QEI 20 
QEI H1   H1   H 0 1 N N N 21.655 20.776 18.741 -2.964 -0.752 1.167  H1   QEI 21 
QEI H2   H2   H 0 1 N N N 20.724 22.195 20.930 -3.123 -0.253 -1.822 H2   QEI 22 
QEI H3   H3   H 0 1 N N N 19.417 20.869 17.133 -2.023 1.858  1.247  H3   QEI 23 
QEI H4   H4   H 0 1 N N N 18.816 23.441 20.120 -4.930 1.251  -1.607 H4   QEI 24 
QEI H5   H5   H 0 1 N N N 18.530 23.230 17.379 -4.089 2.899  0.231  H5   QEI 25 
QEI H6   H6   H 0 1 N N N 20.647 18.274 18.543 -0.431 -0.068 1.773  H6   QEI 26 
QEI H6A  H6A  H 0 1 N N N 20.902 17.960 20.167 -0.931 -1.761 1.543  H6A  QEI 27 
QEI HO1  HO1  H 0 1 N N N 22.068 23.296 18.663 -4.945 -1.760 -1.484 HO1  QEI 28 
QEI HO2  HO2  H 0 1 N N N 20.275 25.089 19.997 -6.393 1.115  0.277  HO2  QEI 29 
QEI HN1  HN1  H 0 1 N N N 20.345 20.107 20.730 -1.296 -1.221 -0.799 HN1  QEI 30 
QEI H8   H8   H 0 1 N N N 18.170 18.021 17.529 0.856  -3.396 0.541  H8   QEI 31 
QEI HN2  HN2  H 0 1 N N N 15.888 17.497 18.495 3.280  -3.149 -0.217 HN2  QEI 32 
QEI HN5  HN5  H 0 1 N N N 15.201 17.967 24.382 6.280  0.853  -1.046 HN5  QEI 33 
QEI HN5A HN5A H 0 0 N N N 14.041 18.119 23.042 5.624  2.377  -0.783 HN5A QEI 34 
QEI HN4  HN4  H 0 1 N N N 17.436 17.904 24.145 3.413  2.605  -0.062 HN4  QEI 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 
QEI C1  C2   SING N N 1  
QEI C1  C3   SING N N 2  
QEI C1  N1   SING N N 3  
QEI C2  C4   SING N N 4  
QEI C2  O1   SING N N 5  
QEI C3  C5   DOUB N N 6  
QEI C4  C5   SING N N 7  
QEI C4  O2   SING N N 8  
QEI C6  N1   SING N N 9  
QEI C6  C7   SING N N 10 
QEI C9  C10  DOUB N N 11 
QEI C9  C11  SING N N 12 
QEI C9  C7   SING N N 13 
QEI C10 N2   SING N N 14 
QEI C10 N3   SING N N 15 
QEI C11 N4   SING N N 16 
QEI C11 O3   DOUB N N 17 
QEI C7  C8   DOUB Y N 18 
QEI C8  N2   SING N N 19 
QEI N3  C12  DOUB Y N 20 
QEI C12 N5   SING Y N 21 
QEI C12 N4   SING N N 22 
QEI C1  H1   SING N N 23 
QEI C2  H2   SING N N 24 
QEI C3  H3   SING N N 25 
QEI C4  H4   SING N N 26 
QEI C5  H5   SING N N 27 
QEI C6  H6   SING Y N 28 
QEI C6  H6A  SING Y N 29 
QEI O1  HO1  SING N N 30 
QEI O2  HO2  SING N N 31 
QEI N1  HN1  SING N N 32 
QEI C8  H8   SING N N 33 
QEI N2  HN2  SING N N 34 
QEI N5  HN5  SING N N 35 
QEI N5  HN5A SING N N 36 
QEI N4  HN4  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 
QEI SMILES           ACDLabs              10.04 O=C1c2c(cnc2N=C(N1)N)CNC3C=CC(O)C3O                                                                                                                          
QEI InChI            InChI                1.02b InChI=1/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/f/h15,17H,13H2 
QEI InChIKey         InChI                1.02b WYROLENTHWJFLR-GJWHZQJUDB                                                                                                                                    
QEI SMILES_CANONICAL CACTVS               3.341 NC1=Nc2[nH]cc(CN[C@H]3C=C[C@H](O)[C@@H]3O)c2C(=O)N1                                                                                                          
QEI SMILES           CACTVS               3.341 NC1=Nc2[nH]cc(CN[CH]3C=C[CH](O)[CH]3O)c2C(=O)N1                                                                                                              
QEI SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1c(c2c([nH]1)N=C(NC2=O)N)CN[C@H]3C=C[C@@H]([C@@H]3O)O                                                                                                       
QEI SMILES           "OpenEye OEToolkits" 1.5.0 c1c(c2c([nH]1)N=C(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 
QEI "SYSTEMATIC NAME" ACDLabs              10.04 2-amino-5-({[(1S,4S,5R)-4,5-dihydroxycyclopent-2-en-1-yl]amino}methyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one 
QEI "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 2-amino-5-[[[(1S,4S,5R)-4,5-dihydroxy-1-cyclopent-2-enyl]amino]methyl]-3,7-dihydropyrrolo[3,2-e]pyrimidin-4-one     
# 
