data_J2A # _chem_comp.id J2A _chem_comp.name "(2S,5R,7R,8R,10R,12aR,14R,15R,15aS,16R)-7-(2-amino-6-oxo-3,6-dihydro-9H-purin-9-yl)-14-(6-amino-9H-purin-9-yl)-15,16-dihydroxy-2,10-disulfanyloctahydro-2H,10H,12H-5,8-methano-2lambda~5~,10lambda~5~-furo[3,2-l][1,3,6,9,11,2,10]pentaoxadiphosphacyclotetradecine-2,10-dione" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C20 H24 N10 O11 P2 S2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "nonhydrolyzable phosphorothioate analog of 2'3' cyclic GMP-AMP" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2018-08-03 _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 706.542 _chem_comp.one_letter_code ? _chem_comp.three_letter_code J2A _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 6EA8 _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 J2A C27 C1 C 0 1 N N S -16.490 16.413 -34.766 2.519 -0.905 0.407 C27 J2A 1 J2A C30 C2 C 0 1 N N R -15.566 18.336 -35.619 4.638 -0.062 -0.414 C30 J2A 2 J2A C32 C3 C 0 1 Y N N -14.891 19.799 -37.449 7.007 0.519 0.256 C32 J2A 3 J2A C34 C4 C 0 1 Y N N -16.113 21.089 -38.934 9.002 -0.600 0.482 C34 J2A 4 J2A C40 C5 C 0 1 Y N N -13.252 18.832 -36.377 5.559 2.182 0.276 C40 J2A 5 J2A C38 C6 C 0 1 Y N N -13.723 20.204 -38.017 7.641 1.707 0.655 C38 J2A 6 J2A C10 C7 C 0 1 Y N N -16.760 10.662 -33.219 -6.377 0.180 0.265 C10 J2A 7 J2A C15 C8 C 0 1 N N N -15.403 9.142 -34.686 -8.531 0.512 1.384 C15 J2A 8 J2A C02 C9 C 0 1 N N R -18.462 14.078 -31.810 -2.126 -0.702 0.809 C02 J2A 9 J2A C03 C10 C 0 1 N N R -17.322 13.169 -31.624 -3.095 0.306 0.146 C03 J2A 10 J2A C08 C11 C 0 1 N N R -17.967 11.844 -31.424 -4.127 -0.640 -0.516 C08 J2A 11 J2A C12 C12 C 0 1 N N N -16.503 11.100 -35.730 -7.825 1.981 -0.264 C12 J2A 12 J2A C17 C13 C 0 1 Y N N -15.979 9.547 -33.322 -7.294 -0.257 1.213 C17 J2A 13 J2A C19 C14 C 0 1 Y N N -16.598 9.775 -31.240 -5.623 -1.631 1.255 C19 J2A 14 J2A C21 C15 C 0 1 N N R -19.564 13.247 -32.447 -2.153 -1.842 -0.240 C21 J2A 15 J2A C22 C16 C 0 1 N N N -19.877 13.566 -33.905 -1.597 -3.125 0.348 C22 J2A 16 J2A C28 C17 C 0 1 N N R -15.719 16.891 -35.924 4.007 -0.770 0.795 C28 J2A 17 J2A C36 C18 C 0 1 Y N N -13.805 21.111 -39.116 9.012 1.658 0.961 C36 J2A 18 J2A C42 C19 C 0 1 N N R -15.984 17.284 -33.638 2.318 0.112 -0.724 C42 J2A 19 J2A C43 C20 C 0 1 N N N -15.104 16.471 -32.748 1.383 1.235 -0.271 C43 J2A 20 J2A N09 N1 N 0 1 Y N N -17.138 10.803 -31.934 -5.335 -0.694 0.306 N09 J2A 21 J2A N11 N2 N 0 1 N N N -17.049 11.480 -34.434 -6.663 1.307 -0.463 N11 J2A 22 J2A N13 N3 N 0 1 N N N -16.797 11.905 -36.899 -8.073 3.102 -1.010 N13 J2A 23 J2A N14 N4 N 0 1 N N N -15.681 9.928 -35.842 -8.722 1.600 0.621 N14 J2A 24 J2A N18 N5 N 0 1 Y N N -15.884 9.007 -32.103 -6.782 -1.369 1.789 N18 J2A 25 J2A N31 N6 N 0 1 Y N N -14.582 18.953 -36.437 5.696 0.849 0.024 N31 J2A 26 J2A N33 N7 N 0 1 Y N N -16.088 20.252 -37.920 7.719 -0.601 0.187 N33 J2A 27 J2A N35 N8 N 0 1 Y N N -15.003 21.508 -39.520 9.642 0.493 0.858 N35 J2A 28 J2A N37 N9 N 0 1 N N N -12.620 21.599 -39.793 9.690 2.797 1.359 N37 J2A 29 J2A N39 N10 N 0 1 Y N N -12.718 19.593 -37.345 6.701 2.684 0.646 N39 J2A 30 J2A O01 O1 O 0 1 N N N -18.907 14.518 -30.539 -0.819 -0.180 0.973 O01 J2A 31 J2A O04 O2 O 0 1 N N N -16.476 13.579 -30.523 -2.429 1.050 -0.869 O04 J2A 32 J2A O07 O3 O 0 1 N N N -14.422 13.994 -31.755 -1.080 2.416 0.774 O07 J2A 33 J2A O16 O4 O 0 1 N N N -14.726 8.177 -34.794 -9.370 0.170 2.203 O16 J2A 34 J2A O20 O5 O 0 1 N N N -19.199 11.872 -32.206 -3.542 -1.949 -0.602 O20 J2A 35 J2A O23 O6 O 0 1 N N N -18.783 13.962 -34.706 -0.193 -2.950 0.590 O23 J2A 36 J2A O26 O7 O 0 1 N N N -17.899 16.594 -34.899 2.269 -2.239 -0.032 O26 J2A 37 J2A O29 O8 O 0 1 N N N -16.417 16.722 -37.158 4.592 -2.062 0.963 O29 J2A 38 J2A O41 O9 O 0 1 N N N -15.231 18.356 -34.213 3.595 0.665 -1.060 O41 J2A 39 J2A O44 O10 O 0 1 N N N -15.941 15.894 -31.803 0.190 1.219 -1.055 O44 J2A 40 J2A O45 O11 O 0 1 N N N -20.190 15.852 -35.513 0.337 -1.796 -1.596 O45 J2A 41 J2A P05 P1 P 0 1 N N R -15.318 14.714 -30.861 -1.156 2.004 -0.649 P05 J2A 42 J2A P24 P2 P 0 1 N N S -18.811 15.391 -35.562 0.867 -2.768 -0.609 P24 J2A 43 J2A S06 S1 S 0 1 N N N -14.084 15.523 -29.303 -1.352 3.731 -1.865 S06 J2A 44 J2A S25 S2 S 0 1 N N N -18.404 15.232 -37.630 1.162 -4.638 -1.568 S25 J2A 45 J2A H1 H1 H 0 1 N N N -16.248 15.360 -34.557 1.887 -0.661 1.261 H1 J2A 46 J2A H2 H2 H 0 1 N N N -16.536 18.833 -35.768 5.049 -0.807 -1.097 H2 J2A 47 J2A H3 H3 H 0 1 N N N -17.066 21.444 -39.298 9.552 -1.527 0.416 H3 J2A 48 J2A H4 H4 H 0 1 N N N -12.702 18.227 -35.672 4.639 2.739 0.182 H4 J2A 49 J2A H5 H5 H 0 1 N N N -18.193 14.920 -32.464 -2.536 -1.053 1.755 H5 J2A 50 J2A H6 H6 H 0 1 N N N -16.729 13.140 -32.550 -3.570 0.939 0.879 H6 J2A 51 J2A H7 H7 H 0 1 N N N -18.189 11.687 -30.358 -4.362 -0.279 -1.512 H7 J2A 52 J2A H8 H8 H 0 1 N N N -16.715 9.596 -30.181 -4.987 -2.462 1.523 H8 J2A 53 J2A H9 H9 H 0 1 N N N -20.482 13.451 -31.877 -1.589 -1.530 -1.114 H9 J2A 54 J2A H10 H10 H 0 1 N N N -20.616 14.381 -33.919 -2.101 -3.364 1.283 H10 J2A 55 J2A H11 H11 H 0 1 N N N -20.316 12.665 -34.359 -1.732 -3.949 -0.358 H11 J2A 56 J2A H12 H12 H 0 1 N N N -14.734 16.403 -35.957 4.121 -0.173 1.695 H12 J2A 57 J2A H13 H13 H 0 1 N N N -16.837 17.673 -33.063 1.901 -0.381 -1.602 H13 J2A 58 J2A H14 H14 H 0 1 N N N -14.589 15.692 -33.329 1.138 1.109 0.781 H14 J2A 59 J2A H15 H15 H 0 1 N N N -14.359 17.114 -32.256 1.886 2.199 -0.405 H15 J2A 60 J2A H16 H16 H 0 1 N N N -17.622 12.296 -34.358 -6.029 1.626 -1.125 H16 J2A 61 J2A H17 H17 H 0 1 N N N -16.427 11.645 -37.791 -7.424 3.401 -1.666 H17 J2A 62 J2A H18 H18 H 0 1 N N N -17.370 12.720 -36.814 -8.897 3.597 -0.883 H18 J2A 63 J2A H19 H19 H 0 1 N N N -12.888 22.218 -40.531 9.219 3.642 1.431 H19 J2A 64 J2A H20 H20 H 0 1 N N N -12.042 22.089 -39.141 10.636 2.750 1.567 H20 J2A 65 J2A H21 H21 H 0 1 N N N -18.228 15.040 -30.128 -0.198 -0.795 1.386 H21 J2A 66 J2A H22 H22 H 0 1 N N N -16.510 15.795 -37.345 5.543 -2.043 1.137 H22 J2A 67 J2A H23 H23 H 0 1 N N N -12.902 15.109 -29.652 -0.236 4.427 -1.585 H23 J2A 68 J2A H24 H24 H 0 1 N N N -19.533 15.603 -38.157 -0.072 -4.955 -1.999 H24 J2A 69 # # 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 J2A N37 C36 SING N N 1 J2A N35 C36 DOUB Y N 2 J2A N35 C34 SING Y N 3 J2A C36 C38 SING Y N 4 J2A C34 N33 DOUB Y N 5 J2A C38 C32 DOUB Y N 6 J2A C38 N39 SING Y N 7 J2A N33 C32 SING Y N 8 J2A S25 P24 SING N N 9 J2A C32 N31 SING Y N 10 J2A N39 C40 DOUB Y N 11 J2A O29 C28 SING N N 12 J2A N13 C12 SING N N 13 J2A N31 C40 SING Y N 14 J2A N31 C30 SING N N 15 J2A C28 C30 SING N N 16 J2A C28 C27 SING N N 17 J2A N14 C12 DOUB N N 18 J2A N14 C15 SING N N 19 J2A C12 N11 SING N N 20 J2A C30 O41 SING N N 21 J2A P24 O45 DOUB N N 22 J2A P24 O26 SING N N 23 J2A P24 O23 SING N N 24 J2A O26 C27 SING N N 25 J2A O16 C15 DOUB N N 26 J2A C27 C42 SING N N 27 J2A O23 C22 SING N N 28 J2A C15 C17 SING N N 29 J2A N11 C10 SING N N 30 J2A O41 C42 SING N N 31 J2A C22 C21 SING N N 32 J2A C42 C43 SING N N 33 J2A C17 C10 DOUB Y N 34 J2A C17 N18 SING Y N 35 J2A C10 N09 SING Y N 36 J2A C43 O44 SING N N 37 J2A C21 O20 SING N N 38 J2A C21 C02 SING N N 39 J2A O20 C08 SING N N 40 J2A N18 C19 DOUB Y N 41 J2A N09 C08 SING N N 42 J2A N09 C19 SING Y N 43 J2A C02 C03 SING N N 44 J2A C02 O01 SING N N 45 J2A O44 P05 SING N N 46 J2A O07 P05 DOUB N N 47 J2A C03 C08 SING N N 48 J2A C03 O04 SING N N 49 J2A P05 O04 SING N N 50 J2A P05 S06 SING N N 51 J2A C27 H1 SING N N 52 J2A C30 H2 SING N N 53 J2A C34 H3 SING N N 54 J2A C40 H4 SING N N 55 J2A C02 H5 SING N N 56 J2A C03 H6 SING N N 57 J2A C08 H7 SING N N 58 J2A C19 H8 SING N N 59 J2A C21 H9 SING N N 60 J2A C22 H10 SING N N 61 J2A C22 H11 SING N N 62 J2A C28 H12 SING N N 63 J2A C42 H13 SING N N 64 J2A C43 H14 SING N N 65 J2A C43 H15 SING N N 66 J2A N11 H16 SING N N 67 J2A N13 H17 SING N N 68 J2A N13 H18 SING N N 69 J2A N37 H19 SING N N 70 J2A N37 H20 SING N N 71 J2A O01 H21 SING N N 72 J2A O29 H22 SING N N 73 J2A S06 H23 SING N N 74 J2A S25 H24 SING N N 75 # # 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 J2A SMILES ACDLabs 12.01 "C54C(COP(OC1C(O)C(OC1n3c2c(C(N=C(N2)N)=O)nc3)COP(O4)(=O)S)(=O)S)OC(C5O)n6c7c(nc6)c(ncn7)N" J2A InChI InChI 1.03 "InChI=1S/C20H24N10O11P2S2/c21-14-8-15(24-3-23-14)29(4-25-8)18-11(32)12-7(39-18)2-37-43(35,45)41-13-10(31)6(1-36-42(34,44)40-12)38-19(13)30-5-26-9-16(30)27-20(22)28-17(9)33/h3-7,10-13,18-19,31-32H,1-2H2,(H,34,44)(H,35,45)(H2,21,23,24)(H3,22,27,28,33)/t6-,7-,10-,11-,12-,13-,18-,19-,42+,43-/m1/s1" J2A InChIKey InChI 1.03 NVOTUSOAWRDABP-JRZJYRHUSA-N J2A SMILES_CANONICAL CACTVS 3.385 "NC1=NC(=O)c2ncn([C@@H]3O[C@@H]4CO[P@@](S)(=O)O[C@H]5[C@@H](O)[C@@H](O[C@@H]5CO[P@](S)(=O)O[C@@H]3[C@@H]4O)n6cnc7c(N)ncnc67)c2N1" J2A SMILES CACTVS 3.385 "NC1=NC(=O)c2ncn([CH]3O[CH]4CO[P](S)(=O)O[CH]5[CH](O)[CH](O[CH]5CO[P](S)(=O)O[CH]3[CH]4O)n6cnc7c(N)ncnc67)c2N1" J2A SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@H]4[C@H](O3)CO[P@](=O)(O[C@@H]5[C@@H]([C@@H](CO[P@@](=O)(O4)S)O[C@H]5n6cnc7c6NC(=NC7=O)N)O)S)O)N" J2A SMILES "OpenEye OEToolkits" 2.0.6 "c1nc(c2c(n1)n(cn2)C3C(C4C(O3)COP(=O)(OC5C(C(COP(=O)(O4)S)OC5n6cnc7c6NC(=NC7=O)N)O)S)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 J2A "SYSTEMATIC NAME" ACDLabs 12.01 "(2S,5R,7R,8R,10R,12aR,14R,15R,15aS,16R)-7-(2-amino-6-oxo-3,6-dihydro-9H-purin-9-yl)-14-(6-amino-9H-purin-9-yl)-15,16-dihydroxy-2,10-disulfanyloctahydro-2H,10H,12H-5,8-methano-2lambda~5~,10lambda~5~-furo[3,2-l][1,3,6,9,11,2,10]pentaoxadiphosphacyclotetradecine-2,10-dione" J2A "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.6 "9-[(1~{R},3~{R},6~{R},8~{R},9~{R},10~{S},12~{S},15~{R},17~{R},18~{R})-8-(6-aminopurin-9-yl)-9,18-bis(oxidanyl)-3,12-bis(oxidanylidene)-3,12-bis(sulfanyl)-2,4,7,11,13,16-hexaoxa-3$l^{5},12$l^{5}-diphosphatricyclo[13.2.1.0^{6,10}]octadecan-17-yl]-2-azanyl-3~{H}-purin-6-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 J2A "Create component" 2018-08-03 RCSB J2A "Modify synonyms" 2018-08-31 RCSB J2A "Modify synonyms" 2018-09-04 RCSB J2A "Initial release" 2019-02-06 RCSB J2A "Modify synonyms" 2021-03-01 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id J2A _pdbx_chem_comp_synonyms.name "nonhydrolyzable phosphorothioate analog of 2'3' cyclic GMP-AMP" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##