data_AMZ # _chem_comp.id AMZ _chem_comp.name "AMINOIMIDAZOLE 4-CARBOXAMIDE RIBONUCLEOTIDE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C9 H15 N4 O8 P" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms AICAR _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2002-08-15 _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 AC4 _chem_comp.formula_weight 338.211 _chem_comp.one_letter_code ? _chem_comp.three_letter_code AMZ _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details ? _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 1M9N _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 AMZ O5 O5 O 0 1 N N N 34.123 -12.017 36.924 0.528 -0.654 6.083 O5 AMZ 1 AMZ C6 C6 C 0 1 N N N 35.061 -11.981 36.121 1.264 0.009 5.377 C6 AMZ 2 AMZ N2 N2 N 0 1 N N N 35.895 -12.995 36.101 2.334 0.630 5.913 N2 AMZ 3 AMZ C3A C3A C 0 1 Y N N 35.247 -10.783 35.183 0.988 0.132 3.943 C3A AMZ 4 AMZ C7A C7A C 0 1 Y N N 34.380 -9.660 35.166 -0.065 -0.451 3.255 C7A AMZ 5 AMZ N3 N3 N 0 1 N N N 33.234 -9.447 35.988 -1.055 -1.254 3.785 N3 AMZ 6 AMZ N1 N1 N 0 1 Y N N 36.252 -10.632 34.246 1.721 0.836 3.038 N1 AMZ 7 AMZ C5 C5 C 0 1 Y N N 35.894 -9.420 33.736 1.177 0.718 1.864 C5 AMZ 8 AMZ N N N 0 1 Y N N 34.763 -8.739 34.233 0.066 -0.068 1.953 N AMZ 9 AMZ C1 C1 C 0 1 N N R 34.064 -7.458 33.830 -0.820 -0.439 0.848 C1 AMZ 10 AMZ C2 C2 C 0 1 N N R 35.084 -6.342 34.025 -1.934 0.616 0.675 C2 AMZ 11 AMZ C3 C3 C 0 1 N N S 35.521 -6.234 32.572 -2.128 0.707 -0.856 C3 AMZ 12 AMZ O2 O2 O 0 1 N N N 35.946 -4.885 32.358 -3.461 0.335 -1.215 O2 AMZ 13 AMZ O1 O1 O 0 1 N N N 34.471 -5.194 34.609 -3.141 0.188 1.308 O1 AMZ 14 AMZ O O O 0 1 N N N 33.460 -7.562 32.554 -0.098 -0.426 -0.402 O AMZ 15 AMZ C C C 0 1 N N R 34.239 -6.605 31.802 -1.111 -0.307 -1.424 C AMZ 16 AMZ C4 C4 C 0 1 N N N 34.629 -7.206 30.441 -0.498 0.220 -2.723 C4 AMZ 17 AMZ O3 O3 O 0 1 N N N 35.487 -8.369 30.535 0.489 -0.699 -3.191 O3 AMZ 18 AMZ P P P 0 1 N N N 36.202 -8.897 29.164 1.090 -0.084 -4.552 P AMZ 19 AMZ OP1 OP1 O 0 1 N N N 37.103 -7.636 28.718 2.216 -1.075 -5.138 OP1 AMZ 20 AMZ O4 O4 O 0 1 N N N 37.137 -10.179 29.385 -0.091 0.082 -5.633 O4 AMZ 21 AMZ OP2 OP2 O 0 1 N N N 34.995 -9.279 28.198 1.694 1.237 -4.272 OP2 AMZ 22 AMZ H11 H11 H 0 1 N N N 35.771 -13.792 36.725 2.517 0.548 6.862 H11 AMZ 23 AMZ H12 H12 H 0 1 N N N 36.669 -12.965 35.438 2.922 1.155 5.349 H12 AMZ 24 AMZ H9 H9 H 0 1 N N N 32.610 -8.639 35.975 -1.053 -1.465 4.732 H9 AMZ 25 AMZ H10 H10 H 0 1 N N N 33.556 -9.539 36.951 -1.752 -1.606 3.210 H10 AMZ 26 AMZ H13 H13 H 0 1 N N N 36.513 -8.994 32.928 1.547 1.173 0.957 H13 AMZ 27 AMZ H2 H2 H 0 1 N N N 33.179 -7.222 34.467 -1.255 -1.423 1.026 H2 AMZ 28 AMZ H3 H3 H 0 1 N N N 35.934 -6.492 34.730 -1.613 1.577 1.077 H3 AMZ 29 AMZ H4 H4 H 0 1 N N N 36.369 -6.885 32.256 -1.904 1.712 -1.212 H4 AMZ 30 AMZ H5 H5 H 0 1 N N N 36.218 -4.817 31.450 -4.049 1.002 -0.835 H5 AMZ 31 AMZ H1 H1 H 0 1 N N N 35.106 -4.498 34.730 -3.812 0.858 1.113 H1 AMZ 32 AMZ H6 H6 H 0 1 N N N 33.622 -5.688 31.649 -1.592 -1.270 -1.597 H6 AMZ 33 AMZ H7 H7 H 0 1 N N N 33.718 -7.438 29.840 -1.279 0.328 -3.476 H7 AMZ 34 AMZ H8 H8 H 0 1 N N N 35.092 -6.429 29.788 -0.034 1.188 -2.538 H8 AMZ 35 AMZ H15 H15 H 0 1 N N N 37.518 -7.943 27.920 2.549 -0.671 -5.951 H15 AMZ 36 AMZ H14 H14 H 0 1 N N N 37.552 -10.486 28.587 -0.456 -0.799 -5.786 H14 AMZ 37 # # 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 AMZ O5 C6 DOUB N N 1 AMZ C6 N2 SING N N 2 AMZ C6 C3A SING N N 3 AMZ N2 H11 SING N N 4 AMZ N2 H12 SING N N 5 AMZ C3A C7A DOUB Y N 6 AMZ C3A N1 SING Y N 7 AMZ C7A N3 SING N N 8 AMZ C7A N SING Y N 9 AMZ N3 H9 SING N N 10 AMZ N3 H10 SING N N 11 AMZ N1 C5 DOUB Y N 12 AMZ C5 N SING Y N 13 AMZ C5 H13 SING N N 14 AMZ N C1 SING N N 15 AMZ C1 C2 SING N N 16 AMZ C1 O SING N N 17 AMZ C1 H2 SING N N 18 AMZ C2 C3 SING N N 19 AMZ C2 O1 SING N N 20 AMZ C2 H3 SING N N 21 AMZ C3 O2 SING N N 22 AMZ C3 C SING N N 23 AMZ C3 H4 SING N N 24 AMZ O2 H5 SING N N 25 AMZ O1 H1 SING N N 26 AMZ O C SING N N 27 AMZ C C4 SING N N 28 AMZ C H6 SING N N 29 AMZ C4 O3 SING N N 30 AMZ C4 H7 SING N N 31 AMZ C4 H8 SING N N 32 AMZ O3 P SING N N 33 AMZ P OP1 SING N N 34 AMZ P O4 SING N N 35 AMZ P OP2 DOUB N N 36 AMZ OP1 H15 SING N N 37 AMZ O4 H14 SING N N 38 # # 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 AMZ SMILES ACDLabs 10.04 "O=C(c1ncn(c1N)C2OC(C(O)C2O)COP(=O)(O)O)N" AMZ SMILES_CANONICAL CACTVS 3.341 "NC(=O)c1ncn([C@@H]2O[C@H](CO[P](O)(O)=O)[C@@H](O)[C@H]2O)c1N" AMZ SMILES CACTVS 3.341 "NC(=O)c1ncn([CH]2O[CH](CO[P](O)(O)=O)[CH](O)[CH]2O)c1N" AMZ SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1nc(c(n1[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O)N)C(=O)N" AMZ SMILES "OpenEye OEToolkits" 1.5.0 "c1nc(c(n1C2C(C(C(O2)COP(=O)(O)O)O)O)N)C(=O)N" AMZ InChI InChI 1.03 "InChI=1S/C9H15N4O8P/c10-7-4(8(11)16)12-2-13(7)9-6(15)5(14)3(21-9)1-20-22(17,18)19/h2-3,5-6,9,14-15H,1,10H2,(H2,11,16)(H2,17,18,19)/t3-,5-,6-,9-/m1/s1" AMZ InChIKey InChI 1.03 NOTGFIUVDGNKRI-UUOKFMHZSA-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 AMZ "SYSTEMATIC NAME" ACDLabs 10.04 "5-amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-1H-imidazole-4-carboxamide" AMZ "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-5-(5-amino-4-aminocarbonyl-imidazol-1-yl)-3,4-dihydroxy-oxolan-2-yl]methyl dihydrogen phosphate" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site AMZ "Create component" 2002-08-15 RCSB AMZ "Modify descriptor" 2011-06-04 RCSB AMZ "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id AMZ _pdbx_chem_comp_synonyms.name AICAR _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##