data_5A8 # _chem_comp.id 5A8 _chem_comp.name "5'-azido-5'-deoxy-8-[(2-{[2-(1H-indol-3-yl)ethyl]amino}-2-oxoethyl)sulfanyl]adenosine" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C22 H24 N10 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 524.556 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 5A8 _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 5DHU _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 5A8 C2 C1 C 0 1 Y N N 13.950 -19.265 -45.576 6.335 3.246 -0.164 C2 5A8 1 5A8 C4 C2 C 0 1 Y N N 11.781 -18.789 -45.276 4.553 1.796 -0.091 C4 5A8 2 5A8 C5 C3 C 0 1 Y N N 11.732 -18.270 -46.520 3.681 2.873 -0.317 C5 5A8 3 5A8 C6 C4 C 0 1 Y N N 12.867 -18.253 -47.279 4.235 4.154 -0.473 C6 5A8 4 5A8 N9 N1 N 0 1 Y N N 10.612 -18.683 -44.751 3.760 0.676 0.012 N9 5A8 5 5A8 CBF C5 C 0 1 Y N N 10.026 -20.807 -48.073 -7.284 0.528 0.361 CBF 5A8 6 5A8 CBK C6 C 0 1 Y N N 11.343 -21.047 -48.325 -7.129 0.725 1.735 CBK 5A8 7 5A8 CBJ C7 C 0 1 Y N N 12.085 -21.764 -47.422 -8.094 0.285 2.596 CBJ 5A8 8 5A8 CBI C8 C 0 1 Y N N 11.508 -22.234 -46.274 -9.229 -0.355 2.117 CBI 5A8 9 5A8 CBH C9 C 0 1 Y N N 10.188 -21.996 -46.036 -9.402 -0.560 0.766 CBH 5A8 10 5A8 CBG C10 C 0 1 Y N N 9.465 -21.286 -46.938 -8.432 -0.121 -0.130 CBG 5A8 11 5A8 NBD N2 N 0 1 Y N N 8.226 -20.926 -46.929 -8.314 -0.174 -1.500 NBD 5A8 12 5A8 CBE C11 C 0 1 Y N N 7.971 -20.250 -48.015 -7.141 0.414 -1.889 CBE 5A8 13 5A8 CBC C12 C 0 1 Y N N 9.040 -20.159 -48.745 -6.470 0.854 -0.812 CBC 5A8 14 5A8 CBA C13 C 0 1 N N N 9.096 -19.418 -50.057 -5.138 1.557 -0.812 CBA 5A8 15 5A8 CAZ C14 C 0 1 N N N 8.244 -18.155 -50.019 -4.023 0.537 -0.575 CAZ 5A8 16 5A8 NAY N3 N 0 1 N N N 8.436 -17.515 -48.735 -2.727 1.220 -0.574 NAY 5A8 17 5A8 CAX C15 C 0 1 N N N 7.466 -17.116 -47.987 -1.594 0.517 -0.383 CAX 5A8 18 5A8 OBB O1 O 0 1 N N N 6.312 -17.188 -48.323 -1.646 -0.683 -0.210 OBB 5A8 19 5A8 CAW C16 C 0 1 N N N 7.890 -16.526 -46.649 -0.261 1.220 -0.382 CAW 5A8 20 5A8 SAA S1 S 0 1 N N N 8.241 -17.780 -45.373 1.058 0.013 -0.102 SAA 5A8 21 5A8 C8 C17 C 0 1 Y N N 9.853 -18.108 -45.623 2.462 1.077 -0.149 C8 5A8 22 5A8 N7 N4 N 0 1 Y N N 10.518 -17.853 -46.704 2.420 2.373 -0.342 N7 5A8 23 5A8 N6 N5 N 0 1 N N N 12.903 -17.768 -48.474 3.424 5.254 -0.703 N6 5A8 24 5A8 N1 N6 N 0 1 Y N N 13.946 -18.760 -46.774 5.554 4.288 -0.384 N1 5A8 25 5A8 N3 N7 N 0 1 Y N N 12.897 -19.285 -44.828 5.860 2.026 -0.023 N3 5A8 26 5A8 CAL C18 C 0 1 N N R 10.230 -19.145 -43.445 4.222 -0.695 0.248 CAL 5A8 27 5A8 OAM O2 O 0 1 N N N 9.094 -19.899 -43.698 3.454 -1.632 -0.538 OAM 5A8 28 5A8 CAP C19 C 0 1 N N R 9.763 -18.063 -42.490 3.931 -1.124 1.709 CAP 5A8 29 5A8 OAQ O3 O 0 1 N N N 10.590 -18.117 -41.387 4.991 -0.722 2.579 OAQ 5A8 30 5A8 CAO C20 C 0 1 N N S 8.400 -18.532 -42.049 3.870 -2.666 1.587 CAO 5A8 31 5A8 OAR O4 O 0 1 N N N 8.263 -18.418 -40.650 5.120 -3.247 1.965 OAR 5A8 32 5A8 CAN C21 C 0 1 N N R 8.430 -19.984 -42.481 3.588 -2.917 0.093 CAN 5A8 33 5A8 CAS C22 C 0 1 N N N 7.008 -20.453 -42.744 2.291 -3.712 -0.065 CAS 5A8 34 5A8 NAT N8 N 0 1 N N N 6.954 -21.915 -42.722 2.085 -4.033 -1.480 NAT 5A8 35 5A8 NAU N9 N 1 1 N N N 6.907 -22.560 -43.830 2.020 -5.106 -1.809 NAU 5A8 36 5A8 NAV N10 N -1 1 N N N 6.860 -23.207 -44.936 1.956 -6.179 -2.138 NAV 5A8 37 5A8 H1 H1 H 0 1 N N N 14.868 -19.684 -45.192 7.402 3.399 -0.104 H1 5A8 38 5A8 H2 H2 H 0 1 N N N 11.800 -20.675 -49.230 -6.249 1.222 2.115 H2 5A8 39 5A8 H3 H3 H 0 1 N N N 13.129 -21.959 -47.618 -7.974 0.438 3.659 H3 5A8 40 5A8 H4 H4 H 0 1 N N N 12.096 -22.791 -45.560 -9.983 -0.697 2.810 H4 5A8 41 5A8 H5 H5 H 0 1 N N N 9.721 -22.369 -45.137 -10.288 -1.060 0.403 H5 5A8 42 5A8 H6 H6 H 0 1 N N N 7.567 -21.132 -46.206 -8.965 -0.569 -2.101 H6 5A8 43 5A8 H7 H7 H 0 1 N N N 7.010 -19.828 -48.270 -6.803 0.508 -2.911 H7 5A8 44 5A8 H8 H8 H 0 1 N N N 8.725 -20.076 -50.856 -4.984 2.046 -1.774 H8 5A8 45 5A8 H9 H9 H 0 1 N N N 10.139 -19.140 -50.267 -5.121 2.304 -0.018 H9 5A8 46 5A8 H10 H10 H 0 1 N N N 8.554 -17.473 -50.824 -4.176 0.048 0.387 H10 5A8 47 5A8 H11 H11 H 0 1 N N N 7.184 -18.418 -50.149 -4.039 -0.210 -1.369 H11 5A8 48 5A8 H12 H12 H 0 1 N N N 9.372 -17.375 -48.411 -2.685 2.180 -0.712 H12 5A8 49 5A8 H13 H13 H 0 1 N N N 8.799 -15.927 -46.806 -0.108 1.709 -1.344 H13 5A8 50 5A8 H14 H14 H 0 1 N N N 7.081 -15.876 -46.284 -0.245 1.967 0.412 H14 5A8 51 5A8 H15 H15 H 0 1 N N N 13.825 -17.868 -48.847 3.819 6.135 -0.801 H15 5A8 52 5A8 H16 H16 H 0 1 N N N 12.254 -18.261 -49.053 2.463 5.143 -0.766 H16 5A8 53 5A8 H17 H17 H 0 1 N N N 11.029 -19.741 -42.981 5.285 -0.784 0.026 H17 5A8 54 5A8 H18 H18 H 0 1 N N N 9.723 -17.077 -42.976 2.976 -0.723 2.049 H18 5A8 55 5A8 H19 H19 H 0 1 N N N 10.329 -17.451 -40.762 4.854 -0.969 3.504 H19 5A8 56 5A8 H20 H20 H 0 1 N N N 7.611 -17.987 -42.587 3.063 -3.066 2.202 H20 5A8 57 5A8 H21 H21 H 0 1 N N N 7.400 -18.717 -40.390 5.138 -4.212 1.908 H21 5A8 58 5A8 H22 H22 H 0 1 N N N 8.937 -20.620 -41.740 4.418 -3.464 -0.354 H22 5A8 59 5A8 H23 H23 H 0 1 N N N 6.681 -20.091 -43.730 2.357 -4.635 0.511 H23 5A8 60 5A8 H24 H24 H 0 1 N N N 6.342 -20.052 -41.966 1.453 -3.116 0.298 H24 5A8 61 # 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 5A8 CBA CAZ SING N N 1 5A8 CBA CBC SING N N 2 5A8 CAZ NAY SING N N 3 5A8 CBC CBF SING Y N 4 5A8 CBC CBE DOUB Y N 5 5A8 NAY CAX SING N N 6 5A8 N6 C6 SING N N 7 5A8 CBK CBF DOUB Y N 8 5A8 CBK CBJ SING Y N 9 5A8 OBB CAX DOUB N N 10 5A8 CBF CBG SING Y N 11 5A8 CBE NBD SING Y N 12 5A8 CAX CAW SING N N 13 5A8 CBJ CBI DOUB Y N 14 5A8 C6 N1 DOUB Y N 15 5A8 C6 C5 SING Y N 16 5A8 CBG NBD SING Y N 17 5A8 CBG CBH DOUB Y N 18 5A8 N1 C2 SING Y N 19 5A8 N7 C5 SING Y N 20 5A8 N7 C8 DOUB Y N 21 5A8 CAW SAA SING N N 22 5A8 C5 C4 DOUB Y N 23 5A8 CBI CBH SING Y N 24 5A8 C8 SAA SING N N 25 5A8 C8 N9 SING Y N 26 5A8 C2 N3 DOUB Y N 27 5A8 C4 N3 SING Y N 28 5A8 C4 N9 SING Y N 29 5A8 NAV NAU DOUB N N 30 5A8 N9 CAL SING N N 31 5A8 NAU NAT DOUB N N 32 5A8 OAM CAL SING N N 33 5A8 OAM CAN SING N N 34 5A8 CAL CAP SING N N 35 5A8 CAS NAT SING N N 36 5A8 CAS CAN SING N N 37 5A8 CAP CAO SING N N 38 5A8 CAP OAQ SING N N 39 5A8 CAN CAO SING N N 40 5A8 CAO OAR SING N N 41 5A8 C2 H1 SING N N 42 5A8 CBK H2 SING N N 43 5A8 CBJ H3 SING N N 44 5A8 CBI H4 SING N N 45 5A8 CBH H5 SING N N 46 5A8 NBD H6 SING N N 47 5A8 CBE H7 SING N N 48 5A8 CBA H8 SING N N 49 5A8 CBA H9 SING N N 50 5A8 CAZ H10 SING N N 51 5A8 CAZ H11 SING N N 52 5A8 NAY H12 SING N N 53 5A8 CAW H13 SING N N 54 5A8 CAW H14 SING N N 55 5A8 N6 H15 SING N N 56 5A8 N6 H16 SING N N 57 5A8 CAL H17 SING N N 58 5A8 CAP H18 SING N N 59 5A8 OAQ H19 SING N N 60 5A8 CAO H20 SING N N 61 5A8 OAR H21 SING N N 62 5A8 CAN H22 SING N N 63 5A8 CAS H23 SING N N 64 5A8 CAS H24 SING N N 65 # 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 5A8 SMILES ACDLabs 12.01 "c5nc4n(C1C(C(O)C(O1)CN=[N+]=[N-])O)c(SCC(NCCc3c2c(cccc2)nc3)=O)nc4c(n5)N" 5A8 InChI InChI 1.03 "InChI=1S/C22H24N10O4S/c23-19-16-20(28-10-27-19)32(21-18(35)17(34)14(36-21)8-29-31-24)22(30-16)37-9-15(33)25-6-5-11-7-26-13-4-2-1-3-12(11)13/h1-4,7,10,14,17-18,21,26,34-35H,5-6,8-9H2,(H,25,33)(H2,23,27,28)/t14-,17-,18-,21-/m1/s1" 5A8 InChIKey InChI 1.03 NZVSVIHQZMZCNV-HAXDFEGKSA-N 5A8 SMILES_CANONICAL CACTVS 3.385 "Nc1ncnc2n([C@@H]3O[C@H](CN=[N+]=[N-])[C@@H](O)[C@H]3O)c(SCC(=O)NCCc4c[nH]c5ccccc45)nc12" 5A8 SMILES CACTVS 3.385 "Nc1ncnc2n([CH]3O[CH](CN=[N+]=[N-])[CH](O)[CH]3O)c(SCC(=O)NCCc4c[nH]c5ccccc45)nc12" 5A8 SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "c1ccc2c(c1)c(c[nH]2)CCNC(=O)CSc3nc4c(ncnc4n3[C@H]5[C@@H]([C@@H]([C@H](O5)CN=[N+]=[N-])O)O)N" 5A8 SMILES "OpenEye OEToolkits" 1.9.2 "c1ccc2c(c1)c(c[nH]2)CCNC(=O)CSc3nc4c(ncnc4n3C5C(C(C(O5)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 5A8 "SYSTEMATIC NAME" ACDLabs 12.01 "5'-azido-5'-deoxy-8-[(2-{[2-(1H-indol-3-yl)ethyl]amino}-2-oxoethyl)sulfanyl]adenosine" 5A8 "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-(1H-indol-3-yl)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 5A8 "Create component" 2015-08-31 EBI 5A8 "Initial release" 2016-09-14 RCSB #