data_4UR # _chem_comp.id 4UR _chem_comp.name "3'2'-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-amino-9-[(2S,5R,7R,8R,10R,12aR,14R,15R,15aS,16R)-7-(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-14-yl]-1,9-dihydro-6H-purin-6-one" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2015-06-01 _chem_comp.pdbx_modified_date 2021-03-13 _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 4UR _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 5BQX _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 4UR C21 C1 C 0 1 N N R -23.322 20.818 -11.107 4.351 -2.433 -1.106 C21 4UR 1 4UR C22 C2 C 0 1 N N N -22.269 21.700 -11.802 3.133 -2.866 -1.924 C22 4UR 2 4UR C28 C3 C 0 1 N N S -19.191 22.699 -8.729 -1.033 -0.924 -0.527 C28 4UR 3 4UR N01 N1 N 0 1 N N N -11.891 21.849 -8.226 -8.197 -1.667 -1.237 N01 4UR 4 4UR C02 C4 C 0 1 N N N -13.079 21.126 -7.992 -7.510 -0.630 -0.659 C02 4UR 5 4UR N03 N2 N 0 1 N N N -14.251 21.811 -7.819 -6.243 -0.797 -0.351 N03 4UR 6 4UR C04 C5 C 0 1 Y N N -15.383 21.001 -7.580 -5.534 0.187 0.214 C04 4UR 7 4UR C05 C6 C 0 1 Y N N -15.375 19.588 -7.511 -6.145 1.417 0.484 C05 4UR 8 4UR N06 N3 N 0 1 Y N N -16.668 19.096 -7.253 -5.208 2.217 1.049 N06 4UR 9 4UR C07 C7 C 0 1 Y N N -17.447 20.192 -7.162 -4.085 1.567 1.139 C07 4UR 10 4UR N08 N4 N 0 1 Y N N -16.700 21.381 -7.342 -4.237 0.308 0.636 N08 4UR 11 4UR C09 C8 C 0 1 N N R -17.288 22.738 -7.317 -3.203 -0.725 0.560 C09 4UR 12 4UR O10 O1 O 0 1 N N N -18.462 22.834 -6.517 -2.187 -0.481 1.537 O10 4UR 13 4UR C11 C9 C 0 1 N N R -19.613 23.151 -7.349 -0.913 -0.865 1.002 C11 4UR 14 4UR C12 C10 C 0 1 N N N -20.876 22.433 -6.841 0.144 0.159 1.416 C12 4UR 15 4UR O13 O2 O 0 1 N N N -20.724 21.046 -6.789 1.132 -0.465 2.237 O13 4UR 16 4UR P14 P1 P 0 1 N N N -21.834 19.900 -6.436 2.504 0.259 2.677 P14 4UR 17 4UR O15 O3 O 0 1 N N N -21.112 18.542 -6.506 2.355 1.724 2.519 O15 4UR 18 4UR O16 O4 O 0 1 N N N -22.458 20.286 -5.141 2.822 -0.081 4.217 O16 4UR 19 4UR O17 O5 O 0 1 N N N -22.942 19.765 -7.677 3.711 -0.258 1.745 O17 4UR 20 4UR C18 C11 C 0 1 N N R -22.522 20.058 -8.956 3.516 -0.779 0.437 C18 4UR 21 4UR C19 C12 C 0 1 N N R -23.410 21.127 -9.618 3.931 -2.270 0.371 C19 4UR 22 4UR O20 O6 O 0 1 N N N -24.757 21.040 -9.190 5.044 -2.513 1.230 O20 4UR 23 4UR O23 O7 O 0 1 N N N -21.002 21.405 -11.283 1.962 -2.192 -1.456 O23 4UR 24 4UR P24 P2 P 0 1 N N N -19.779 22.578 -11.317 0.753 -2.937 -0.702 P24 4UR 25 4UR O25 O8 O 0 1 N N N -20.304 23.647 -12.268 0.999 -2.931 0.759 O25 4UR 26 4UR O26 O9 O 0 1 N N N -18.429 22.016 -11.616 0.668 -4.466 -1.209 O26 4UR 27 4UR O27 O10 O 0 1 N N N -19.877 23.232 -9.797 -0.637 -2.201 -1.021 O27 4UR 28 4UR C29 C13 C 0 1 N N R -17.739 23.136 -8.715 -2.532 -0.691 -0.822 C29 4UR 29 4UR O30 O11 O 0 1 N N N -17.666 24.520 -8.993 -3.036 -1.749 -1.643 O30 4UR 30 4UR O31 O12 O 0 1 N N N -22.980 19.414 -11.206 4.801 -1.147 -1.541 O31 4UR 31 4UR C32 C14 C 0 1 N N R -22.760 18.872 -9.913 4.465 -0.130 -0.592 C32 4UR 32 4UR N33 N5 N 0 1 Y N N -21.557 17.917 -10.021 3.789 0.973 -1.270 N33 4UR 33 4UR C34 C15 C 0 1 Y N N -20.305 18.327 -10.486 3.106 0.899 -2.448 C34 4UR 34 4UR N35 N6 N 0 1 Y N N -19.386 17.321 -10.523 2.630 2.069 -2.761 N35 4UR 35 4UR C36 C16 C 0 1 Y N N -20.051 16.170 -10.066 2.975 2.966 -1.806 C36 4UR 36 4UR C37 C17 C 0 1 Y N N -19.612 14.808 -9.864 2.749 4.339 -1.613 C37 4UR 37 4UR N38 N7 N 0 1 N N N -18.303 14.353 -10.147 2.020 5.073 -2.532 N38 4UR 38 4UR N39 N8 N 0 1 Y N N -20.522 13.886 -9.388 3.251 4.917 -0.526 N39 4UR 39 4UR C40 C18 C 0 1 Y N N -21.813 14.332 -9.124 3.948 4.224 0.356 C40 4UR 40 4UR N41 N9 N 0 1 Y N N -22.317 15.585 -9.268 4.185 2.937 0.216 N41 4UR 41 4UR C42 C19 C 0 1 Y N N -21.411 16.524 -9.745 3.718 2.273 -0.836 C42 4UR 42 4UR C43 C20 C 0 1 N N N -14.140 18.859 -7.696 -7.509 1.582 0.148 C43 4UR 43 4UR O44 O13 O 0 1 N N N -13.911 17.661 -7.680 -8.083 2.636 0.366 O44 4UR 44 4UR N45 N10 N 0 1 N N N -12.979 19.713 -7.944 -8.159 0.546 -0.426 N45 4UR 45 4UR H211 H1 H 0 0 N N N -24.302 21.002 -11.571 5.147 -3.164 -1.188 H211 4UR 46 4UR H221 H2 H 0 0 N N N -22.502 22.760 -11.623 3.297 -2.614 -2.973 H221 4UR 47 4UR H222 H3 H 0 0 N N N -22.279 21.500 -12.884 3.004 -3.945 -1.836 H222 4UR 48 4UR H281 H4 H 0 0 N N N -19.224 21.600 -8.762 -0.444 -0.130 -0.991 H281 4UR 49 4UR H012 H5 H 0 0 N N N -11.913 22.848 -8.264 -9.132 -1.558 -1.474 H012 4UR 50 4UR H011 H6 H 0 0 N N N -11.027 21.363 -8.354 -7.749 -2.510 -1.409 H011 4UR 51 4UR H071 H7 H 0 0 N N N -18.510 20.166 -6.975 -3.169 1.965 1.550 H071 4UR 52 4UR H091 H8 H 0 0 N N N -16.532 23.457 -6.969 -3.644 -1.708 0.730 H091 4UR 53 4UR H111 H9 H 0 0 N N N -19.792 24.236 -7.356 -0.651 -1.850 1.394 H111 4UR 54 4UR H121 H10 H 0 0 N N N -21.106 22.800 -5.830 0.625 0.572 0.530 H121 4UR 55 4UR H122 H11 H 0 0 N N N -21.711 22.670 -7.516 -0.337 0.971 1.965 H122 4UR 56 4UR H1 H12 H 0 1 N N N -22.314 19.598 -4.502 2.136 0.209 4.834 H1 4UR 57 4UR H181 H13 H 0 0 N N N -21.467 20.367 -8.994 2.484 -0.664 0.112 H181 4UR 58 4UR H191 H14 H 0 0 N N N -22.992 22.125 -9.421 3.103 -2.922 0.610 H191 4UR 59 4UR H201 H15 H 0 0 N N N -24.808 21.233 -8.261 5.407 -3.406 1.160 H201 4UR 60 4UR H2 H16 H 0 1 N N N -18.079 22.430 -12.396 1.470 -4.980 -1.043 H2 4UR 61 4UR H291 H17 H 0 0 N N N -17.175 22.555 -9.460 -2.684 0.273 -1.304 H291 4UR 62 4UR H301 H18 H 0 0 N N N -16.757 24.798 -8.985 -3.973 -1.662 -1.864 H301 4UR 63 4UR H321 H19 H 0 0 N N N -23.639 18.306 -9.572 5.364 0.221 -0.093 H321 4UR 64 4UR H341 H20 H 0 0 N N N -20.087 19.341 -10.787 2.980 0.001 -3.036 H341 4UR 65 4UR H381 H21 H 0 0 N N N -18.238 13.376 -9.946 1.658 4.641 -3.321 H381 4UR 66 4UR H382 H22 H 0 0 N N N -18.098 14.508 -11.113 1.870 6.021 -2.387 H382 4UR 67 4UR H401 H23 H 0 0 N N N -22.503 13.586 -8.758 4.338 4.733 1.225 H401 4UR 68 4UR H451 H24 H 0 0 N N N -12.086 19.286 -8.084 -9.094 0.637 -0.669 H451 4UR 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 4UR O25 P24 DOUB N N 1 4UR C22 O23 SING N N 2 4UR C22 C21 SING N N 3 4UR O26 P24 SING N N 4 4UR P24 O23 SING N N 5 4UR P24 O27 SING N N 6 4UR O31 C21 SING N N 7 4UR O31 C32 SING N N 8 4UR C21 C19 SING N N 9 4UR N35 C34 DOUB Y N 10 4UR N35 C36 SING Y N 11 4UR C34 N33 SING Y N 12 4UR N38 C37 SING N N 13 4UR C36 C37 DOUB Y N 14 4UR C36 C42 SING Y N 15 4UR N33 C32 SING N N 16 4UR N33 C42 SING Y N 17 4UR C32 C18 SING N N 18 4UR C37 N39 SING Y N 19 4UR O27 C28 SING N N 20 4UR C42 N41 DOUB Y N 21 4UR C19 O20 SING N N 22 4UR C19 C18 SING N N 23 4UR N39 C40 DOUB Y N 24 4UR N41 C40 SING Y N 25 4UR O30 C29 SING N N 26 4UR C18 O17 SING N N 27 4UR C28 C29 SING N N 28 4UR C28 C11 SING N N 29 4UR C29 C09 SING N N 30 4UR N01 C02 SING N N 31 4UR C02 N45 SING N N 32 4UR C02 N03 DOUB N N 33 4UR N45 C43 SING N N 34 4UR N03 C04 SING N N 35 4UR C43 O44 DOUB N N 36 4UR C43 C05 SING N N 37 4UR O17 P14 SING N N 38 4UR C04 C05 DOUB Y N 39 4UR C04 N08 SING Y N 40 4UR C05 N06 SING Y N 41 4UR C11 C12 SING N N 42 4UR C11 O10 SING N N 43 4UR N08 C09 SING N N 44 4UR N08 C07 SING Y N 45 4UR C09 O10 SING N N 46 4UR N06 C07 DOUB Y N 47 4UR C12 O13 SING N N 48 4UR O13 P14 SING N N 49 4UR O15 P14 DOUB N N 50 4UR P14 O16 SING N N 51 4UR C21 H211 SING N N 52 4UR C22 H221 SING N N 53 4UR C22 H222 SING N N 54 4UR C28 H281 SING N N 55 4UR N01 H012 SING N N 56 4UR N01 H011 SING N N 57 4UR C07 H071 SING N N 58 4UR C09 H091 SING N N 59 4UR C11 H111 SING N N 60 4UR C12 H121 SING N N 61 4UR C12 H122 SING N N 62 4UR O16 H1 SING N N 63 4UR C18 H181 SING N N 64 4UR C19 H191 SING N N 65 4UR O20 H201 SING N N 66 4UR O26 H2 SING N N 67 4UR C29 H291 SING N N 68 4UR O30 H301 SING N N 69 4UR C32 H321 SING N N 70 4UR C34 H341 SING N N 71 4UR N38 H381 SING N N 72 4UR N38 H382 SING N N 73 4UR C40 H401 SING N N 74 4UR N45 H451 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 4UR SMILES ACDLabs 12.01 "C45C(C(OP(OCC3C(C(C(n2c1N=C(N)NC(c1nc2)=O)O3)O)OP(OC4)(=O)O)(O)=O)C(O5)n6c7c(nc6)c(ncn7)N)O" 4UR InChI InChI 1.03 "InChI=1S/C20H24N10O13P2/c21-14-8-15(24-3-23-14)29(4-25-8)19-13-10(31)6(40-19)1-38-44(34,35)42-12-7(2-39-45(36,37)43-13)41-18(11(12)32)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" 4UR InChIKey InChI 1.03 FAFONCPHZLORMH-INFSMZHSSA-N 4UR SMILES_CANONICAL CACTVS 3.385 "NC1=Nc2n(cnc2C(=O)N1)[C@@H]3O[C@@H]4CO[P](O)(=O)O[C@@H]5[C@H](O)[C@@H](CO[P](O)(=O)O[C@H]4[C@H]3O)O[C@H]5n6cnc7c(N)ncnc67" 4UR SMILES CACTVS 3.385 "NC1=Nc2n(cnc2C(=O)N1)[CH]3O[CH]4CO[P](O)(=O)O[CH]5[CH](O)[CH](CO[P](O)(=O)O[CH]4[CH]3O)O[CH]5n6cnc7c(N)ncnc67" 4UR SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "c1nc(c2c(n1)n(cn2)[C@H]3[C@H]4[C@@H]([C@H](O3)COP(=O)(O[C@@H]5[C@@H](COP(=O)(O4)O)O[C@H]([C@@H]5O)n6cnc7c6N=C(NC7=O)N)O)O)N" 4UR SMILES "OpenEye OEToolkits" 1.9.2 "c1nc(c2c(n1)n(cn2)C3C4C(C(O3)COP(=O)(OC5C(COP(=O)(O4)O)OC(C5O)n6cnc7c6N=C(NC7=O)N)O)O)N" # _pdbx_chem_comp_identifier.comp_id 4UR _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-[(2S,5R,7R,8R,10R,12aR,14R,15R,15aS,16R)-7-(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-14-yl]-1,9-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 4UR "Create component" 2015-06-01 RCSB 4UR "Initial release" 2015-06-24 RCSB 4UR "Modify synonyms" 2021-03-13 RCSB # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 4UR _pdbx_chem_comp_synonyms.name "2-amino-9-[(2S,5R,7R,8R,10R,12aR,14R,15R,15aS,16R)-7-(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-14-yl]-1,9-dihydro-6H-purin-6-one" _pdbx_chem_comp_synonyms.provenance PDB _pdbx_chem_comp_synonyms.type ? ##