data_N5A # _chem_comp.id N5A _chem_comp.name "5'-N-[(2-AMINO)ETHYL CARBOXAMIDO] ADENOSINE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C12 H17 N7 O4" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "(2S,3S,4R,5R)-N-(2-AMINOETHYL)-5-(6-AMINO-9H-PURIN-9-YL)-3,4-DIHYDROXYTETRAHYDROFURAN-2-CARBOXAMIDE" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2006-06-26 _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 323.308 _chem_comp.one_letter_code ? _chem_comp.three_letter_code N5A _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 ? _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 N5A N53 N53 N 0 1 N N N -144.568 -38.051 78.869 7.680 1.130 -0.467 N53 N5A 1 N5A C52 C52 C 0 1 N N N -143.903 -36.979 79.625 6.558 0.195 -0.316 C52 N5A 2 N5A C51 C51 C 0 1 N N N -142.755 -37.576 80.440 5.290 0.974 0.040 C51 N5A 3 N5A "N5'" N5* N 0 1 N N N -143.291 -38.619 81.327 4.170 0.041 0.192 "N5'" N5A 4 N5A "C5'" C5* C 0 1 N N N -143.590 -38.376 82.601 2.945 0.505 0.507 "C5'" N5A 5 N5A "O5'" O5* O 0 1 N N N -143.433 -37.282 83.130 2.768 1.694 0.665 "O5'" N5A 6 N5A "C4'" C4* C 0 1 N N S -144.143 -39.527 83.449 1.793 -0.455 0.662 "C4'" N5A 7 N5A "O4'" O4* O 0 1 N N N -143.126 -40.084 84.299 0.589 0.251 1.032 "O4'" N5A 8 N5A "C3'" C3* C 0 1 N N S -145.248 -39.058 84.394 1.434 -1.102 -0.699 "C3'" N5A 9 N5A "O3'" O3* O 0 1 N N N -146.495 -39.043 83.693 2.233 -2.261 -0.947 "O3'" N5A 10 N5A "C2'" C2* C 0 1 N N R -145.236 -40.249 85.348 -0.052 -1.489 -0.491 "C2'" N5A 11 N5A "O2'" O2* O 0 1 N N N -145.732 -41.408 84.671 -0.164 -2.868 -0.133 "O2'" N5A 12 N5A "C1'" C1* C 0 1 N N R -143.728 -40.379 85.573 -0.519 -0.591 0.671 "C1'" N5A 13 N5A N9 N9 N 0 1 Y N N -143.260 -39.356 86.536 -1.652 0.233 0.244 N9 N5A 14 N5A C8 C8 C 0 1 Y N N -142.778 -38.151 86.241 -1.587 1.504 -0.243 C8 N5A 15 N5A N7 N7 N 0 1 Y N N -142.415 -37.532 87.363 -2.783 1.935 -0.524 N7 N5A 16 N5A C5 C5 C 0 1 Y N N -142.669 -38.346 88.384 -3.689 0.970 -0.236 C5 N5A 17 N5A C4 C4 C 0 1 Y N N -143.210 -39.512 87.856 -2.974 -0.136 0.255 C4 N5A 18 N5A N3 N3 N 0 1 Y N N -143.536 -40.521 88.675 -3.641 -1.226 0.621 N3 N5A 19 N5A C2 C2 C 0 1 Y N N -143.345 -40.416 89.978 -4.952 -1.277 0.516 C2 N5A 20 N5A N1 N1 N 0 1 Y N N -142.836 -39.321 90.515 -5.666 -0.266 0.055 N1 N5A 21 N5A C6 C6 C 0 1 Y N N -142.489 -38.269 89.757 -5.087 0.867 -0.329 C6 N5A 22 N5A N6 N6 N 0 1 N N N -141.993 -37.170 90.321 -5.844 1.921 -0.811 N6 N5A 23 N5A H531 1H53 H 0 0 N N N -143.990 -38.867 78.870 7.853 1.526 0.444 H531 N5A 24 N5A H532 2H53 H 0 0 N N N -144.719 -37.751 77.927 8.490 0.576 -0.701 H532 N5A 25 N5A H521 1H52 H 0 0 N N N -144.626 -36.500 80.301 6.403 -0.342 -1.251 H521 N5A 26 N5A H522 2H52 H 0 0 N N N -143.507 -36.227 78.927 6.782 -0.516 0.479 H522 N5A 27 N5A H511 1H51 H 0 0 N N N -142.276 -36.788 81.040 5.444 1.511 0.976 H511 N5A 28 N5A H512 2H51 H 0 0 N N N -142.009 -38.015 79.761 5.065 1.685 -0.754 H512 N5A 29 N5A "HN5'" HN5* H 0 0 N N N -143.435 -39.539 80.962 4.311 -0.911 0.065 "HN5'" N5A 30 N5A "H4'" H4* H 0 1 N N N -144.522 -40.265 82.727 2.030 -1.221 1.401 "H4'" N5A 31 N5A "H3'" H3* H 0 1 N N N -145.118 -38.061 84.841 1.538 -0.380 -1.510 "H3'" N5A 32 N5A "HO3'" HO3* H 0 0 N N N -147.210 -39.040 84.318 3.141 -1.953 -1.067 "HO3'" N5A 33 N5A "H2'" H2* H 0 1 N N N -145.841 -40.139 86.260 -0.632 -1.281 -1.390 "H2'" N5A 34 N5A "HO2'" HO2* H 0 0 N N N -145.842 -41.213 83.748 0.141 -3.380 -0.894 "HO2'" N5A 35 N5A "H1'" H1* H 0 1 N N N -143.473 -41.376 85.961 -0.808 -1.207 1.523 "H1'" N5A 36 N5A H8 H8 H 0 1 N N N -142.694 -37.739 85.246 -0.677 2.071 -0.377 H8 N5A 37 N5A H2 H2 H 0 1 N N N -143.611 -41.244 90.619 -5.463 -2.179 0.818 H2 N5A 38 N5A HN61 1HN6 H 0 0 N N N -141.841 -37.043 91.301 -5.409 2.743 -1.089 HN61 N5A 39 N5A HN62 2HN6 H 0 0 N N N -141.796 -36.491 89.613 -6.808 1.838 -0.871 HN62 N5A 40 # # 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 N5A N53 C52 SING N N 1 N5A N53 H531 SING N N 2 N5A N53 H532 SING N N 3 N5A C52 C51 SING N N 4 N5A C52 H521 SING N N 5 N5A C52 H522 SING N N 6 N5A C51 "N5'" SING N N 7 N5A C51 H511 SING N N 8 N5A C51 H512 SING N N 9 N5A "N5'" "C5'" SING N N 10 N5A "N5'" "HN5'" SING N N 11 N5A "C5'" "O5'" DOUB N N 12 N5A "C5'" "C4'" SING N N 13 N5A "C4'" "O4'" SING N N 14 N5A "C4'" "C3'" SING N N 15 N5A "C4'" "H4'" SING N N 16 N5A "O4'" "C1'" SING N N 17 N5A "C3'" "O3'" SING N N 18 N5A "C3'" "C2'" SING N N 19 N5A "C3'" "H3'" SING N N 20 N5A "O3'" "HO3'" SING N N 21 N5A "C2'" "O2'" SING N N 22 N5A "C2'" "C1'" SING N N 23 N5A "C2'" "H2'" SING N N 24 N5A "O2'" "HO2'" SING N N 25 N5A "C1'" N9 SING N N 26 N5A "C1'" "H1'" SING N N 27 N5A N9 C8 SING Y N 28 N5A N9 C4 SING Y N 29 N5A C8 N7 DOUB Y N 30 N5A C8 H8 SING N N 31 N5A N7 C5 SING Y N 32 N5A C5 C4 DOUB Y N 33 N5A C5 C6 SING Y N 34 N5A C4 N3 SING Y N 35 N5A N3 C2 DOUB Y N 36 N5A C2 N1 SING Y N 37 N5A C2 H2 SING N N 38 N5A N1 C6 DOUB Y N 39 N5A C6 N6 SING N N 40 N5A N6 HN61 SING N N 41 N5A N6 HN62 SING N N 42 # # 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 N5A SMILES ACDLabs 10.04 "O=C(NCCN)C3OC(n2cnc1c(ncnc12)N)C(O)C3O" N5A SMILES_CANONICAL CACTVS 3.341 "NCCNC(=O)[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)ncnc23" N5A SMILES CACTVS 3.341 "NCCNC(=O)[CH]1O[CH]([CH](O)[CH]1O)n2cnc3c(N)ncnc23" N5A SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)C(=O)NCCN)O)O)N" N5A SMILES "OpenEye OEToolkits" 1.5.0 "c1nc(c2c(n1)n(cn2)C3C(C(C(O3)C(=O)NCCN)O)O)N" N5A InChI InChI 1.03 "InChI=1S/C12H17N7O4/c13-1-2-15-11(22)8-6(20)7(21)12(23-8)19-4-18-5-9(14)16-3-17-10(5)19/h3-4,6-8,12,20-21H,1-2,13H2,(H,15,22)(H2,14,16,17)/t6-,7+,8-,12+/m0/s1" N5A InChIKey InChI 1.03 XZUQLQNOMFGRFJ-FLNNQWSLSA-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 N5A "SYSTEMATIC NAME" ACDLabs 10.04 "(2S,3S,4R,5R)-N-(2-aminoethyl)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-carboxamide (non-preferred name)" N5A "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S,3S,4R,5R)-N-(2-aminoethyl)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolane-2-carboxamide" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site N5A "Create component" 2006-06-26 RCSB N5A "Modify descriptor" 2011-06-04 RCSB N5A "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id N5A _pdbx_chem_comp_synonyms.name "(2S,3S,4R,5R)-N-(2-AMINOETHYL)-5-(6-AMINO-9H-PURIN-9-YL)-3,4-DIHYDROXYTETRAHYDROFURAN-2-CARBOXAMIDE" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##