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 2021-03-01 _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 Y N 11 QEI C9 C11 SING N N 12 QEI C9 C7 SING Y N 13 QEI C10 N2 SING Y 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 Y N 19 QEI N3 C12 DOUB N N 20 QEI C12 N5 SING N 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 N N 28 QEI C6 H6A SING N 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 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" QEI 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" QEI InChIKey InChI 1.03 WYROLENTHWJFLR-ACLDMZEESA-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 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" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site QEI "Create component" 2007-12-13 PDBJ QEI "Modify aromatic_flag" 2011-06-04 RCSB QEI "Modify descriptor" 2011-06-04 RCSB QEI "Modify synonyms" 2021-03-01 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id QEI _pdbx_chem_comp_synonyms.name queuine _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##