data_5AG # _chem_comp.id 5AG _chem_comp.name "5'-azido-5'-deoxy-8-[(2-{[2-(3-ethynylphenyl)ethyl]amino}-2-oxoethyl)sulfanyl]adenosine" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C22 H23 N9 O4 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2015-08-31 _chem_comp.pdbx_modified_date 2016-09-09 _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 509.541 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 5AG _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 5DHS _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site EBI # 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 5AG C2 C1 C 0 1 Y N N 13.838 -18.045 -45.125 6.171 3.108 -0.752 C2 5AG 1 5AG C4 C2 C 0 1 Y N N 11.598 -17.633 -44.739 4.377 1.718 -0.388 C4 5AG 2 5AG C5 C3 C 0 1 Y N N 11.470 -17.068 -45.984 3.514 2.819 -0.505 C5 5AG 3 5AG C6 C4 C 0 1 Y N N 12.551 -16.988 -46.813 4.078 4.079 -0.766 C6 5AG 4 5AG N9 N1 N 0 1 Y N N 10.408 -17.550 -44.172 3.575 0.626 -0.148 N9 5AG 5 5AG CAA C5 C 0 1 N N N 11.491 -21.883 -44.128 -9.905 -0.962 -2.375 CAA 5AG 6 5AG CAB C6 C 0 1 N N N 10.721 -21.417 -44.884 -9.309 -0.529 -1.461 CAB 5AG 7 5AG CAC C7 C 0 1 Y N N 9.761 -20.861 -45.787 -8.583 -0.002 -0.345 CAC 5AG 8 5AG CAD C8 C 0 1 Y N N 10.130 -20.113 -46.897 -7.347 0.614 -0.541 CAD 5AG 9 5AG CBJ C9 C 0 1 Y N N 8.428 -21.091 -45.515 -9.112 -0.097 0.943 CBJ 5AG 10 5AG CBI C10 C 0 1 Y N N 7.450 -20.579 -46.336 -8.408 0.414 2.014 CBI 5AG 11 5AG CBH C11 C 0 1 Y N N 7.812 -19.833 -47.438 -7.180 1.018 1.813 CBH 5AG 12 5AG CAE C12 C 0 1 Y N N 9.138 -19.608 -47.716 -6.655 1.125 0.538 CAE 5AG 13 5AG CAF C13 C 0 1 N N N 9.457 -18.790 -48.935 -5.316 1.785 0.329 CAF 5AG 14 5AG CAG C14 C 0 1 N N N 8.457 -17.642 -49.060 -4.210 0.732 0.419 CAG 5AG 15 5AG NAH N2 N 0 1 N N N 8.431 -16.917 -47.784 -2.908 1.373 0.215 NAH 5AG 16 5AG CAI C15 C 0 1 N N N 7.491 -16.053 -47.465 -1.781 0.636 0.253 CAI 5AG 17 5AG OBG O1 O 0 1 N N N 6.581 -15.726 -48.213 -1.843 -0.558 0.454 OBG 5AG 18 5AG CAJ C16 C 0 1 N N N 7.641 -15.448 -46.082 -0.442 1.295 0.043 CAJ 5AG 19 5AG SAK S1 S 0 1 N N N 7.976 -16.661 -44.766 0.867 0.050 0.150 SAK 5AG 20 5AG C8 C17 C 0 1 Y N N 9.603 -16.981 -45.039 2.280 1.067 -0.124 C8 5AG 21 5AG N7 N3 N 0 1 Y N N 10.223 -16.670 -46.145 2.249 2.360 -0.334 N7 5AG 22 5AG N6 N4 N 0 1 N N N 12.382 -16.435 -47.987 3.275 5.201 -0.896 N6 5AG 23 5AG N1 N5 N 0 1 Y N N 13.764 -17.478 -46.393 5.399 4.172 -0.875 N1 5AG 24 5AG N3 N6 N 0 1 Y N N 12.779 -18.112 -44.345 5.686 1.906 -0.517 N3 5AG 25 5AG CAV C18 C 0 1 N N R 10.007 -18.021 -42.881 4.025 -0.755 0.045 CAV 5AG 26 5AG OBF O2 O 0 1 N N N 8.754 -18.532 -43.247 3.123 -1.679 -0.600 OBF 5AG 27 5AG CAW C19 C 0 1 N N R 9.640 -16.916 -41.896 3.940 -1.152 1.541 CAW 5AG 28 5AG OAX O3 O 0 1 N N N 10.440 -17.046 -40.746 5.128 -0.772 2.238 OAX 5AG 29 5AG CAY C20 C 0 1 N N S 8.214 -17.247 -41.486 3.816 -2.693 1.461 CAY 5AG 30 5AG OAZ O4 O 0 1 N N N 8.075 -17.277 -40.074 5.090 -3.309 1.662 OAZ 5AG 31 5AG CBA C21 C 0 1 N N R 8.117 -18.654 -41.992 3.309 -2.957 0.030 CBA 5AG 32 5AG CBB C22 C 0 1 N N N 6.642 -18.959 -42.060 1.979 -3.712 0.079 CBB 5AG 33 5AG NBC N7 N 0 1 N N N 6.458 -20.260 -41.439 1.557 -4.048 -1.283 NBC 5AG 34 5AG NBD N8 N 1 1 N N N 6.683 -21.329 -42.141 1.413 -5.123 -1.577 NBD 5AG 35 5AG NBE N9 N -1 1 N N N 6.901 -22.397 -42.839 1.268 -6.198 -1.872 NBE 5AG 36 5AG H1 H1 H 0 1 N N N 14.781 -18.437 -44.774 7.240 3.227 -0.852 H1 5AG 37 5AG H2 H2 H 0 1 N N N 12.185 -22.303 -43.446 -10.437 -1.349 -3.194 H2 5AG 38 5AG H3 H3 H 0 1 N N N 11.172 -19.929 -47.116 -6.932 0.690 -1.535 H3 5AG 39 5AG H4 H4 H 0 1 N N N 8.150 -21.677 -44.651 -10.071 -0.568 1.101 H4 5AG 40 5AG H5 H5 H 0 1 N N N 6.408 -20.760 -46.119 -8.816 0.341 3.011 H5 5AG 41 5AG H6 H6 H 0 1 N N N 7.050 -19.424 -48.085 -6.632 1.416 2.655 H6 5AG 42 5AG H7 H7 H 0 1 N N N 9.396 -19.427 -49.829 -5.292 2.253 -0.655 H7 5AG 43 5AG H8 H8 H 0 1 N N N 10.474 -18.381 -48.845 -5.161 2.543 1.096 H8 5AG 44 5AG H9 H9 H 0 1 N N N 8.768 -16.963 -49.868 -4.234 0.263 1.403 H9 5AG 45 5AG H10 H10 H 0 1 N N N 7.457 -18.042 -49.282 -4.365 -0.026 -0.349 H10 5AG 46 5AG H11 H11 H 0 1 N N N 9.163 -17.088 -47.125 -2.858 2.328 0.054 H11 5AG 47 5AG H12 H12 H 0 1 N N N 8.474 -14.730 -46.109 -0.418 1.764 -0.941 H12 5AG 48 5AG H13 H13 H 0 1 N N N 6.709 -14.919 -45.834 -0.286 2.053 0.811 H13 5AG 49 5AG H14 H14 H 0 1 N N N 13.249 -16.438 -48.485 3.677 6.067 -1.069 H14 5AG 50 5AG H15 H15 H 0 1 N N N 11.699 -16.951 -48.503 2.312 5.121 -0.815 H15 5AG 51 5AG H16 H16 H 0 1 N N N 10.692 -18.762 -42.443 5.041 -0.882 -0.329 H16 5AG 52 5AG H17 H17 H 0 1 N N N 9.706 -15.922 -42.363 3.059 -0.715 2.010 H17 5AG 53 5AG H18 H18 H 0 1 N N N 10.218 -16.361 -40.126 5.123 -0.999 3.178 H18 5AG 54 5AG H19 H19 H 0 1 N N N 7.488 -16.583 -41.978 3.097 -3.057 2.195 H19 5AG 55 5AG H20 H20 H 0 1 N N N 8.133 -16.393 -39.731 5.070 -4.275 1.622 H20 5AG 56 5AG H21 H21 H 0 1 N N N 8.636 -19.355 -41.321 4.047 -3.538 -0.523 H21 5AG 57 5AG H22 H22 H 0 1 N N N 6.071 -18.194 -41.514 2.103 -4.627 0.658 H22 5AG 58 5AG H23 H23 H 0 1 N N N 6.308 -18.988 -43.108 1.223 -3.084 0.550 H23 5AG 59 # 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 5AG CAG CAF SING N N 1 5AG CAG NAH SING N N 2 5AG CAF CAE SING N N 3 5AG OBG CAI DOUB N N 4 5AG N6 C6 SING N N 5 5AG NAH CAI SING N N 6 5AG CAE CBH DOUB Y N 7 5AG CAE CAD SING Y N 8 5AG CAI CAJ SING N N 9 5AG CBH CBI SING Y N 10 5AG CAD CAC DOUB Y N 11 5AG C6 N1 DOUB Y N 12 5AG C6 C5 SING Y N 13 5AG N1 C2 SING Y N 14 5AG CBI CBJ DOUB Y N 15 5AG N7 C5 SING Y N 16 5AG N7 C8 DOUB Y N 17 5AG CAJ SAK SING N N 18 5AG C5 C4 DOUB Y N 19 5AG CAC CBJ SING Y N 20 5AG CAC CAB SING N N 21 5AG C2 N3 DOUB Y N 22 5AG C8 SAK SING N N 23 5AG C8 N9 SING Y N 24 5AG CAB CAA TRIP N N 25 5AG C4 N3 SING Y N 26 5AG C4 N9 SING Y N 27 5AG N9 CAV SING N N 28 5AG OBF CAV SING N N 29 5AG OBF CBA SING N N 30 5AG CAV CAW SING N N 31 5AG NBE NBD DOUB N N 32 5AG NBD NBC DOUB N N 33 5AG CBB CBA SING N N 34 5AG CBB NBC SING N N 35 5AG CBA CAY SING N N 36 5AG CAW CAY SING N N 37 5AG CAW OAX SING N N 38 5AG CAY OAZ SING N N 39 5AG C2 H1 SING N N 40 5AG CAA H2 SING N N 41 5AG CAD H3 SING N N 42 5AG CBJ H4 SING N N 43 5AG CBI H5 SING N N 44 5AG CBH H6 SING N N 45 5AG CAF H7 SING N N 46 5AG CAF H8 SING N N 47 5AG CAG H9 SING N N 48 5AG CAG H10 SING N N 49 5AG NAH H11 SING N N 50 5AG CAJ H12 SING N N 51 5AG CAJ H13 SING N N 52 5AG N6 H14 SING N N 53 5AG N6 H15 SING N N 54 5AG CAV H16 SING N N 55 5AG CAW H17 SING N N 56 5AG OAX H18 SING N N 57 5AG CAY H19 SING N N 58 5AG OAZ H20 SING N N 59 5AG CBA H21 SING N N 60 5AG CBB H22 SING N N 61 5AG CBB H23 SING N N 62 # 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 5AG SMILES ACDLabs 12.01 "c4nc3n(C1C(C(O)C(O1)CN=[N+]=[N-])O)c(SCC(NCCc2cc(C#C)ccc2)=O)nc3c(n4)N" 5AG InChI InChI 1.03 "InChI=1S/C22H23N9O4S/c1-2-12-4-3-5-13(8-12)6-7-25-15(32)10-36-22-29-16-19(23)26-11-27-20(16)31(22)21-18(34)17(33)14(35-21)9-28-30-24/h1,3-5,8,11,14,17-18,21,33-34H,6-7,9-10H2,(H,25,32)(H2,23,26,27)/t14-,17-,18-,21-/m1/s1" 5AG InChIKey InChI 1.03 HEZMFPGXYOAFRQ-HAXDFEGKSA-N 5AG SMILES_CANONICAL CACTVS 3.385 "Nc1ncnc2n([C@@H]3O[C@H](CN=[N+]=[N-])[C@@H](O)[C@H]3O)c(SCC(=O)NCCc4cccc(c4)C#C)nc12" 5AG SMILES CACTVS 3.385 "Nc1ncnc2n([CH]3O[CH](CN=[N+]=[N-])[CH](O)[CH]3O)c(SCC(=O)NCCc4cccc(c4)C#C)nc12" 5AG SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "C#Cc1cccc(c1)CCNC(=O)CSc2nc3c(ncnc3n2[C@H]4[C@@H]([C@@H]([C@H](O4)CN=[N+]=[N-])O)O)N" 5AG SMILES "OpenEye OEToolkits" 1.9.2 "C#Cc1cccc(c1)CCNC(=O)CSc2nc3c(ncnc3n2C4C(C(C(O4)CN=[N+]=[N-])O)O)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 5AG "SYSTEMATIC NAME" ACDLabs 12.01 "5'-azido-5'-deoxy-8-[(2-{[2-(3-ethynylphenyl)ethyl]amino}-2-oxoethyl)sulfanyl]adenosine" 5AG "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "2-[6-azanyl-9-[(2R,3R,4S,5R)-5-(azidomethyl)-3,4-bis(oxidanyl)oxolan-2-yl]purin-8-yl]sulfanyl-N-[2-(3-ethynylphenyl)ethyl]ethanamide" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 5AG "Create component" 2015-08-31 EBI 5AG "Initial release" 2016-09-14 RCSB #