data_1SY # _chem_comp.id 1SY _chem_comp.name cGAMP _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C20 H24 N10 O13 P2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ;2',3' cGAMP; c-GMP-AMP; c[G(2',5')pA(3',5')p] ; _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2013-05-24 _chem_comp.pdbx_modified_date 2020-05-26 _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 674.411 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 1SY _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 4KSY _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 1SY C2 C2 C 0 1 Y N N 52.285 8.645 -17.445 7.555 -0.917 0.622 C2 CGA 1 1SY N01 N01 N 0 1 N N N 49.671 10.964 -18.686 8.057 2.550 -0.093 N01 CGA 2 1SY C6 C6 C 0 1 Y N N 50.424 9.721 -18.417 7.450 1.313 0.032 C6 CGA 3 1SY N1 N1 N 0 1 Y N N 51.572 9.746 -17.722 8.127 0.268 0.498 N1 CGA 4 1SY N3 N3 N 0 1 Y N N 51.861 7.466 -17.865 6.300 -1.133 0.291 N3 CGA 5 1SY C4 C4 C 0 1 Y N N 50.707 7.322 -18.571 5.544 -0.148 -0.184 C4 CGA 6 1SY C5 C5 C 0 1 Y N N 49.932 8.463 -18.884 6.104 1.132 -0.329 C5 CGA 7 1SY N7 N7 N 0 1 Y N N 48.846 8.028 -19.599 5.135 1.938 -0.825 N7 CGA 8 1SY C8 C8 C 0 1 Y N N 48.904 6.680 -19.752 4.042 1.250 -0.990 C8 CGA 9 1SY N9 N9 N 0 1 Y N N 50.021 6.278 -19.141 4.244 -0.043 -0.608 N9 CGA 10 1SY "C1'" "C1'" C 0 1 N N R 50.682 5.019 -18.928 3.254 -1.122 -0.645 "C1'" CGA 11 1SY "C2'" "C2'" C 0 1 N N R 50.380 4.522 -17.603 2.577 -1.255 0.728 "C2'" CGA 12 1SY "O2'" "O2'" O 0 1 N N N 51.440 3.630 -17.229 3.124 -2.361 1.447 "O2'" CGA 13 1SY "C3'" "C3'" C 0 1 N N S 49.138 3.764 -17.764 1.093 -1.515 0.402 "C3'" CGA 14 1SY "C4'" "C4'" C 0 1 N N R 49.370 3.094 -19.052 0.956 -1.196 -1.096 "C4'" CGA 15 1SY C16 C16 C 0 1 N N N 48.077 2.813 -19.760 -0.034 -0.048 -1.296 C16 CGA 16 1SY O17 O17 O 0 1 N N N 47.351 4.005 -19.842 -0.998 -0.416 -2.283 O17 CGA 17 1SY P18 P18 P 0 1 N N N 45.831 3.976 -20.336 -2.326 0.434 -2.600 P18 CGA 18 1SY O19 O19 O 0 1 N N N 45.210 5.359 -20.429 -2.014 2.003 -2.414 O19 CGA 19 1SY O20 O20 O 0 1 N N N 44.941 3.030 -19.356 -3.507 -0.001 -1.594 O20 CGA 20 1SY C21 C21 C 0 1 N N R 45.238 3.102 -17.973 -3.266 -0.650 -0.354 C21 CGA 21 1SY C22 C22 C 0 1 N N R 45.225 1.757 -17.318 -3.912 -2.059 -0.330 C22 CGA 22 1SY O23 O23 O 0 1 N N N 44.203 0.940 -17.865 -5.124 -2.066 -1.082 O23 CGA 23 1SY C24 C24 C 0 1 N N R 44.873 2.031 -15.933 -4.203 -2.261 1.175 C24 CGA 24 1SY C25 C25 C 0 1 N N N 46.069 2.169 -15.026 -2.988 -2.905 1.844 C25 CGA 25 1SY O26 O26 O 0 1 N N N 46.821 3.329 -15.275 -1.793 -2.490 1.184 O26 CGA 26 1SY P27 P27 P 0 1 N N N 48.421 3.298 -15.237 -0.712 -3.505 0.558 P27 CGA 27 1SY O28 O28 O 0 1 N N N 49.055 2.793 -16.676 0.761 -2.875 0.671 O28 CGA 28 1SY O29 O29 O 0 1 N N N 48.935 4.647 -14.857 -0.754 -4.782 1.307 O29 CGA 29 1SY O30 O30 O 0 1 N N N 48.867 2.315 -14.223 -1.066 -3.783 -0.988 O30 CGA 30 1SY O31 O31 O 0 1 N N N 44.051 3.225 -15.940 -4.423 -0.955 1.724 O31 CGA 31 1SY C32 C32 C 0 1 N N R 44.157 3.838 -17.254 -3.994 0.060 0.807 C32 CGA 32 1SY N33 N33 N 0 1 Y N N 44.435 5.171 -17.082 -3.085 0.986 1.476 N33 CGA 33 1SY C34 C34 C 0 1 Y N N 45.479 5.722 -16.498 -2.342 0.724 2.589 C34 CGA 34 1SY N35 N35 N 0 1 Y N N 45.348 7.054 -16.528 -1.646 1.778 2.908 N35 CGA 35 1SY C36 C36 C 0 1 Y N N 43.590 6.164 -17.482 -2.820 2.267 1.099 C36 CGA 36 1SY C37 C37 C 0 1 Y N N 44.175 7.370 -17.126 -1.906 2.766 2.020 C37 CGA 37 1SY C38 C38 C 0 1 N N N 43.486 8.666 -17.444 -1.440 4.146 1.853 C38 CGA 38 1SY N39 N39 N 0 1 N N N 42.231 8.640 -18.103 -1.914 4.863 0.822 N39 CGA 39 1SY C40 C40 C 0 1 N N N 41.638 7.385 -18.456 -2.779 4.352 -0.028 C40 CGA 40 1SY N41 N41 N 0 1 N N N 40.375 7.354 -19.117 -3.233 5.135 -1.055 N41 CGA 41 1SY N42 N42 N 0 1 N N N 42.319 6.133 -18.156 -3.250 3.083 0.084 N42 CGA 42 1SY O43 O43 O 0 1 N N N 44.002 9.763 -17.139 -0.638 4.632 2.634 O43 CGA 43 1SY O44 O44 O 0 1 N N N 45.826 3.332 -21.655 -2.754 0.178 -3.994 O44 CGA 44 1SY "O4'" "O4'" O 0 1 N N N 50.154 4.044 -19.820 2.236 -0.816 -1.598 "O4'" CGA 45 1SY H1 H1 H 0 1 N N N 53.203 8.721 -16.881 8.141 -1.739 1.004 H1 CGA 46 1SY H2 H2 H 0 1 N N N 50.153 11.741 -18.281 8.987 2.662 0.160 H2 CGA 47 1SY H3 H3 H 0 1 N N N 49.593 11.099 -19.674 7.553 3.305 -0.434 H3 CGA 48 1SY H4 H4 H 0 1 N N N 48.188 6.056 -20.266 3.113 1.646 -1.371 H4 CGA 49 1SY H5 H5 H 0 1 N N N 51.769 5.124 -19.061 3.739 -2.060 -0.910 H5 CGA 50 1SY H6 H6 H 0 1 N N N 50.259 5.342 -16.879 2.686 -0.335 1.299 H6 CGA 51 1SY H7 H7 H 0 1 N N N 51.272 3.284 -16.360 4.070 -2.282 1.630 H7 CGA 52 1SY H8 H8 H 0 1 N N N 48.257 4.421 -17.798 0.461 -0.851 0.993 H8 CGA 53 1SY H9 H9 H 0 1 N N N 49.929 2.158 -18.903 0.601 -2.079 -1.628 H9 CGA 54 1SY H10 H10 H 0 1 N N N 47.500 2.065 -19.197 -0.541 0.165 -0.357 H10 CGA 55 1SY H11 H11 H 0 1 N N N 48.282 2.433 -20.772 0.504 0.842 -1.622 H11 CGA 56 1SY H12 H12 H 0 1 N N N 44.943 5.527 -21.325 -1.316 2.337 -2.994 H12 CGA 57 1SY H13 H13 H 0 1 N N N 46.207 3.594 -17.801 -2.201 -0.728 -0.133 H13 CGA 58 1SY H14 H14 H 0 1 N N N 46.214 1.280 -17.392 -3.221 -2.809 -0.697 H14 CGA 59 1SY H15 H15 H 0 1 N N N 44.211 0.092 -17.437 -5.571 -2.923 -1.101 H15 CGA 60 1SY H16 H16 H 0 1 N N N 44.265 1.194 -15.559 -5.088 -2.878 1.302 H16 CGA 61 1SY H17 H17 H 0 1 N N N 45.716 2.198 -13.984 -2.953 -2.594 2.891 H17 CGA 62 1SY H18 H18 H 0 1 N N N 46.719 1.293 -15.169 -3.077 -3.992 1.803 H18 CGA 63 1SY H19 H19 H 0 1 N N N 49.380 2.757 -13.557 -1.939 -4.175 -1.127 H19 CGA 64 1SY H20 H20 H 0 1 N N N 43.211 3.705 -17.799 -4.861 0.594 0.424 H20 CGA 65 1SY H21 H21 H 0 1 N N N 46.309 5.185 -16.064 -2.331 -0.214 3.125 H21 CGA 66 1SY H22 H22 H 0 1 N N N 39.903 8.209 -19.334 -3.879 4.780 -1.686 H22 CGA 67 1SY H23 H23 H 0 1 N N N 39.961 6.478 -19.363 -2.909 6.044 -1.153 H23 CGA 68 1SY H24 H24 H 0 1 N N N 41.907 5.260 -18.416 -3.887 2.747 -0.565 H24 CGA 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 1SY O44 P18 DOUB N N 1 1SY O19 P18 SING N N 2 1SY P18 O17 SING N N 3 1SY P18 O20 SING N N 4 1SY O17 C16 SING N N 5 1SY "O4'" "C4'" SING N N 6 1SY "O4'" "C1'" SING N N 7 1SY C16 "C4'" SING N N 8 1SY C8 N7 DOUB Y N 9 1SY C8 N9 SING Y N 10 1SY N7 C5 SING Y N 11 1SY O20 C21 SING N N 12 1SY N9 "C1'" SING N N 13 1SY N9 C4 SING Y N 14 1SY N41 C40 SING N N 15 1SY "C4'" "C3'" SING N N 16 1SY "C1'" "C2'" SING N N 17 1SY C5 C4 DOUB Y N 18 1SY C5 C6 SING Y N 19 1SY N01 C6 SING N N 20 1SY C4 N3 SING Y N 21 1SY C40 N42 SING N N 22 1SY C40 N39 DOUB N N 23 1SY C6 N1 DOUB Y N 24 1SY N42 C36 SING N N 25 1SY N39 C38 SING N N 26 1SY C21 C22 SING N N 27 1SY C21 C32 SING N N 28 1SY O23 C22 SING N N 29 1SY N3 C2 DOUB Y N 30 1SY "C3'" "C2'" SING N N 31 1SY "C3'" O28 SING N N 32 1SY N1 C2 SING Y N 33 1SY "C2'" "O2'" SING N N 34 1SY C36 C37 DOUB Y N 35 1SY C36 N33 SING Y N 36 1SY C38 O43 DOUB N N 37 1SY C38 C37 SING N N 38 1SY C22 C24 SING N N 39 1SY C32 N33 SING N N 40 1SY C32 O31 SING N N 41 1SY C37 N35 SING Y N 42 1SY N33 C34 SING Y N 43 1SY O28 P27 SING N N 44 1SY N35 C34 DOUB Y N 45 1SY O31 C24 SING N N 46 1SY C24 C25 SING N N 47 1SY O26 P27 SING N N 48 1SY O26 C25 SING N N 49 1SY P27 O29 DOUB N N 50 1SY P27 O30 SING N N 51 1SY C2 H1 SING N N 52 1SY N01 H2 SING N N 53 1SY N01 H3 SING N N 54 1SY C8 H4 SING N N 55 1SY "C1'" H5 SING N N 56 1SY "C2'" H6 SING N N 57 1SY "O2'" H7 SING N N 58 1SY "C3'" H8 SING N N 59 1SY "C4'" H9 SING N N 60 1SY C16 H10 SING N N 61 1SY C16 H11 SING N N 62 1SY O19 H12 SING N N 63 1SY C21 H13 SING N N 64 1SY C22 H14 SING N N 65 1SY O23 H15 SING N N 66 1SY C24 H16 SING N N 67 1SY C25 H17 SING N N 68 1SY C25 H18 SING N N 69 1SY O30 H19 SING N N 70 1SY C32 H20 SING N N 71 1SY C34 H21 SING N N 72 1SY N41 H22 SING N N 73 1SY N41 H23 SING N N 74 1SY N42 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 1SY SMILES ACDLabs 12.01 "O=C7N=C(N)Nc1c7ncn1C5OC6COP(=O)(O)OC4C(OC(n2c3ncnc(N)c3nc2)C4O)COP(=O)(OC5C6O)O" 1SY InChI InChI 1.03 "InChI=1S/C20H24N10O13P2/c21-14-8-15(24-3-23-14)29(4-25-8)18-11(32)12-7(41-18)2-39-45(36,37)43-13-10(31)6(1-38-44(34,35)42-12)40-19(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,34,35)(H,36,37)(H2,21,23,24)(H3,22,27,28,33)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1" 1SY InChIKey InChI 1.03 XRILCFTWUCUKJR-INFSMZHSSA-N 1SY SMILES_CANONICAL CACTVS 3.370 "NC1=NC(=O)c2ncn([C@@H]3O[C@@H]4CO[P](O)(=O)O[C@H]5[C@@H](O)[C@@H](O[C@@H]5CO[P](O)(=O)O[C@@H]3[C@@H]4O)n6cnc7c(N)ncnc67)c2N1" 1SY SMILES CACTVS 3.370 "NC1=NC(=O)c2ncn([CH]3O[CH]4CO[P](O)(=O)O[CH]5[CH](O)[CH](O[CH]5CO[P](O)(=O)O[CH]3[CH]4O)n6cnc7c(N)ncnc67)c2N1" 1SY SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@H]4[C@H](O3)COP(=O)(O[C@@H]5[C@@H]([C@@H](COP(=O)(O4)O)O[C@H]5n6cnc7c6NC(=NC7=O)N)O)O)O)N" 1SY SMILES "OpenEye OEToolkits" 1.7.6 "c1nc(c2c(n1)n(cn2)C3C(C4C(O3)COP(=O)(OC5C(C(COP(=O)(O4)O)OC5n6cnc7c6NC(=NC7=O)N)O)O)O)N" # _pdbx_chem_comp_identifier.comp_id 1SY _pdbx_chem_comp_identifier.type "SYSTEMATIC NAME" _pdbx_chem_comp_identifier.program ACDLabs _pdbx_chem_comp_identifier.program_version 12.01 _pdbx_chem_comp_identifier.identifier "2-amino-9-[(2R,5R,7R,8R,10S,12aR,14R,15R,15aS,16R)-14-(6-amino-9H-purin-9-yl)-2,10,15,16-tetrahydroxy-2,10-dioxidooctahydro-12H-5,8-methanofuro[3,2-l][1,3,6,9,11,2,10]pentaoxadiphosphacyclotetradecin-7-yl]-3,9-dihydro-6H-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 1SY "Create component" 2013-05-24 RCSB 1SY "Initial release" 2013-06-12 RCSB 1SY "Modify synonyms" 2015-07-29 RCSB 1SY "Modify synonyms" 2020-05-26 PDBE # loop_ _pdbx_chem_comp_synonyms.ordinal _pdbx_chem_comp_synonyms.comp_id _pdbx_chem_comp_synonyms.name _pdbx_chem_comp_synonyms.provenance _pdbx_chem_comp_synonyms.type 1 1SY ;2',3' cGAMP ; ? ? 2 1SY c-GMP-AMP ? ? 3 1SY "c[G(2',5')pA(3',5')p]" ? ? #