data_M24 # _chem_comp.id M24 _chem_comp.name "5'-O-[(R)-[({3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]phenyl}carbonyl)oxy](hydroxy)phosphoryl]adenosine" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C25 H21 F N7 O9 P" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2009-07-29 _chem_comp.pdbx_modified_date 2011-06-04 _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 613.448 _chem_comp.one_letter_code ? _chem_comp.three_letter_code M24 _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 3IES _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 M24 P P P 0 1 N N N -29.949 11.676 -8.256 -0.760 -1.819 -0.535 P M24 1 M24 N1 N1 N 0 1 Y N N -30.571 6.598 -16.979 -10.173 3.124 0.372 N1 M24 2 M24 C2 C2 C 0 1 Y N N -30.885 7.881 -17.236 -9.857 2.305 1.359 C2 M24 3 M24 N3 N3 N 0 1 Y N N -30.968 8.808 -16.272 -8.845 1.467 1.285 N3 M24 4 M24 C4 C4 C 0 1 Y N N -30.760 8.478 -14.970 -8.089 1.412 0.193 C4 M24 5 M24 C5 C5 C 0 1 Y N N -30.432 7.189 -14.630 -8.384 2.263 -0.885 C5 M24 6 M24 C6 C6 C 0 1 Y N N -30.323 6.197 -15.714 -9.474 3.140 -0.759 C6 M24 7 M24 N6 N6 N 0 1 N N N -30.015 4.896 -15.433 -9.813 4.002 -1.788 N6 M24 8 M24 N7 N7 N 0 1 Y N N -30.280 7.135 -13.278 -7.474 2.008 -1.856 N7 M24 9 M24 C8 C8 C 0 1 Y N N -30.486 8.388 -12.820 -6.659 1.078 -1.452 C8 M24 10 M24 N9 N9 N 0 1 Y N N -30.791 9.184 -13.845 -6.997 0.677 -0.193 N9 M24 11 M24 "C1'" C1* C 0 1 N N R -31.076 10.627 -13.764 -6.318 -0.350 0.601 C1* M24 12 M24 O1P O1P O 0 1 N N N -28.500 12.111 -8.091 -0.370 -3.232 -0.329 O1P M24 13 M24 "C2'" C2* C 0 1 N N R -32.570 10.911 -13.836 -6.975 -1.729 0.371 C2* M24 14 M24 "O2'" O2* O 0 1 N N N -32.717 12.155 -14.504 -7.889 -2.031 1.428 O2* M24 15 M24 C24 C24 C 0 1 N N N -29.311 9.071 -8.726 1.616 -1.023 -0.222 C24 M24 16 M24 O25 O25 O 0 1 N N N -28.716 9.380 -9.744 1.905 -1.871 -1.042 O25 M24 17 M24 C26 C26 C 0 1 Y N N -29.349 7.675 -8.135 2.674 -0.175 0.366 C26 M24 18 M24 C27 C27 C 0 1 Y N N -29.830 7.537 -6.832 2.344 0.801 1.311 C27 M24 19 M24 C28 C28 C 0 1 Y N N -29.908 6.297 -6.221 3.332 1.593 1.860 C28 M24 20 M24 C29 C29 C 0 1 Y N N -29.478 5.174 -6.895 4.650 1.426 1.481 C29 M24 21 M24 O2P O2P O 0 1 N N N -30.029 10.078 -8.006 0.333 -0.856 0.152 O2P M24 22 M24 "C3'" C3* C 0 1 N N S -32.983 11.100 -12.398 -5.787 -2.717 0.384 C3* M24 23 M24 "O3'" O3* O 0 1 N N N -34.104 11.996 -12.311 -5.931 -3.660 1.449 O3* M24 24 M24 C30 C30 C 0 1 Y N N -29.016 5.303 -8.184 4.991 0.456 0.540 C30 M24 25 M24 C31 C31 C 0 1 Y N N -28.931 6.550 -8.814 4.003 -0.350 -0.014 C31 M24 26 M24 C32 C32 C 0 1 Y N N -28.577 4.072 -8.874 6.408 0.280 0.134 C32 M24 27 M24 N33 N33 N 0 1 Y N N -28.166 4.082 -10.137 6.863 -0.583 -0.738 N33 M24 28 M24 O34 O34 O 0 1 Y N N -27.838 2.819 -10.422 8.066 -0.477 -0.847 O34 M24 29 M24 C35 C35 C 0 1 Y N N -28.030 2.015 -9.378 8.516 0.491 -0.034 C35 M24 30 M24 N36 N36 N 0 1 Y N N -28.491 2.799 -8.374 7.464 0.985 0.592 N36 M24 31 M24 C37 C37 C 0 1 Y N N -27.807 0.573 -9.406 9.919 0.927 0.125 C37 M24 32 M24 C38 C38 C 0 1 Y N N -27.286 -0.049 -10.517 10.239 1.949 1.019 C38 M24 33 M24 C39 C39 C 0 1 Y N N -27.123 -1.429 -10.487 11.551 2.351 1.163 C39 M24 34 M24 O3P O3P O 0 1 N N N -31.003 12.106 -7.290 -0.834 -1.507 -2.113 O3P M24 35 M24 "C4'" C4* C 0 1 N N R -31.724 11.665 -11.751 -4.553 -1.818 0.621 C4* M24 36 M24 "O4'" O4* O 0 1 N N N -30.618 11.119 -12.505 -4.954 -0.512 0.154 O4* M24 37 M24 C40 C40 C 0 1 Y N N -27.514 -2.145 -9.360 12.550 1.742 0.423 C40 M24 38 M24 C41 C41 C 0 1 Y N N -28.077 -1.494 -8.269 12.243 0.728 -0.465 C41 M24 39 M24 C42 C42 C 0 1 Y N N -28.219 -0.124 -8.300 10.934 0.312 -0.616 C42 M24 40 M24 F43 F43 F 0 1 N N N -28.741 0.588 -7.292 10.634 -0.683 -1.480 F43 M24 41 M24 "C5'" C5* C 0 1 N N N -31.605 11.275 -10.286 -3.359 -2.329 -0.188 C5* M24 42 M24 "O5'" O5* O 0 1 N N N -30.370 11.818 -9.803 -2.201 -1.556 0.132 O5* M24 43 M24 H2 H2 H 0 1 N N N -31.077 8.175 -18.257 -10.452 2.324 2.260 H2 M24 44 M24 HN6 HN6 H 0 1 N N N -30.014 4.363 -16.279 -10.568 4.603 -1.688 HN6 M24 45 M24 HN6A HN6A H 0 0 N N N -29.110 4.852 -15.010 -9.296 4.005 -2.608 HN6A M24 46 M24 H8 H8 H 0 1 N N N -30.415 8.697 -11.787 -5.837 0.681 -2.028 H8 M24 47 M24 "H1'" H1* H 0 1 N N N -30.569 11.114 -14.610 -6.342 -0.088 1.659 H1* M24 48 M24 "H2'" H2* H 0 1 N N N -33.150 10.128 -14.346 -7.482 -1.755 -0.593 H2* M24 49 M24 "HO2'" HO2* H 0 0 N N N -33.639 12.372 -14.571 -8.330 -2.886 1.334 HO2* M24 50 M24 H27 H27 H 0 1 N N N -30.148 8.415 -6.289 1.315 0.936 1.610 H27 M24 51 M24 H28 H28 H 0 1 N N N -30.304 6.210 -5.220 3.073 2.347 2.589 H28 M24 52 M24 H29 H29 H 0 1 N N N -29.504 4.206 -6.417 5.418 2.050 1.915 H29 M24 53 M24 "H3'" H3* H 0 1 N N N -33.322 10.179 -11.901 -5.709 -3.233 -0.573 H3* M24 54 M24 "HO3'" HO3* H 0 0 N N N -34.353 12.105 -11.401 -6.724 -4.210 1.383 HO3* M24 55 M24 H31 H31 H 0 1 N N N -28.543 6.630 -9.819 4.264 -1.106 -0.740 H31 M24 56 M24 H38 H38 H 0 1 N N N -27.010 0.521 -11.392 9.461 2.426 1.596 H38 M24 57 M24 H39 H39 H 0 1 N N N -26.695 -1.943 -11.335 11.799 3.143 1.854 H39 M24 58 M24 HO3P HO3P H 0 0 N N N -30.613 12.654 -6.619 -1.084 -0.596 -2.322 HO3P M24 59 M24 "H4'" H4* H 0 1 N N N -31.743 12.765 -11.770 -4.306 -1.785 1.681 H4* M24 60 M24 H40 H40 H 0 1 N N N -27.379 -3.216 -9.333 13.576 2.061 0.541 H40 M24 61 M24 H41 H41 H 0 1 N N N -28.400 -2.056 -7.405 13.028 0.258 -1.039 H41 M24 62 M24 "H5'" H5* H 0 1 N N N -32.450 11.684 -9.713 -3.177 -3.376 0.055 H5* M24 63 M24 "H5'A" H5*A H 0 0 N N N -31.606 10.180 -10.182 -3.575 -2.236 -1.253 H5*A M24 64 # 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 M24 "O5'" P SING N N 1 M24 P O1P DOUB N N 2 M24 P O2P SING N N 3 M24 P O3P SING N N 4 M24 C2 N1 DOUB Y N 5 M24 N1 C6 SING Y N 6 M24 C2 N3 SING Y N 7 M24 C2 H2 SING N N 8 M24 N3 C4 DOUB Y N 9 M24 C4 C5 SING Y N 10 M24 C4 N9 SING Y N 11 M24 C6 C5 DOUB Y N 12 M24 C5 N7 SING Y N 13 M24 C6 N6 SING N N 14 M24 N6 HN6 SING N N 15 M24 N6 HN6A SING N N 16 M24 N7 C8 DOUB Y N 17 M24 N9 C8 SING Y N 18 M24 C8 H8 SING N N 19 M24 N9 "C1'" SING N N 20 M24 "C2'" "C1'" SING N N 21 M24 "C1'" "O4'" SING N N 22 M24 "C1'" "H1'" SING N N 23 M24 "O2'" "C2'" SING N N 24 M24 "C2'" "C3'" SING N N 25 M24 "C2'" "H2'" SING N N 26 M24 "O2'" "HO2'" SING N N 27 M24 O25 C24 DOUB N N 28 M24 C24 C26 SING N N 29 M24 C24 O2P SING N N 30 M24 C31 C26 DOUB Y N 31 M24 C26 C27 SING Y N 32 M24 C27 C28 DOUB Y N 33 M24 C27 H27 SING N N 34 M24 C29 C28 SING Y N 35 M24 C28 H28 SING N N 36 M24 C30 C29 DOUB Y N 37 M24 C29 H29 SING N N 38 M24 "C3'" "O3'" SING N N 39 M24 "C3'" "C4'" SING N N 40 M24 "C3'" "H3'" SING N N 41 M24 "O3'" "HO3'" SING N N 42 M24 C32 C30 SING Y N 43 M24 C31 C30 SING Y N 44 M24 C31 H31 SING N N 45 M24 N33 C32 DOUB Y N 46 M24 C32 N36 SING Y N 47 M24 O34 N33 SING Y N 48 M24 O34 C35 SING Y N 49 M24 C37 C35 SING Y N 50 M24 C35 N36 DOUB Y N 51 M24 C38 C37 DOUB Y N 52 M24 C37 C42 SING Y N 53 M24 C38 C39 SING Y N 54 M24 C38 H38 SING N N 55 M24 C39 C40 DOUB Y N 56 M24 C39 H39 SING N N 57 M24 O3P HO3P SING N N 58 M24 "O4'" "C4'" SING N N 59 M24 "C4'" "C5'" SING N N 60 M24 "C4'" "H4'" SING N N 61 M24 C40 C41 SING Y N 62 M24 C40 H40 SING N N 63 M24 C42 C41 DOUB Y N 64 M24 C41 H41 SING N N 65 M24 C42 F43 SING N N 66 M24 "C5'" "O5'" SING N N 67 M24 "C5'" "H5'" SING N N 68 M24 "C5'" "H5'A" SING N N 69 # 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 M24 SMILES ACDLabs 11.02 "O=P(OCC3OC(n1c2ncnc(N)c2nc1)C(O)C3O)(O)OC(=O)c4cccc(c4)c5nc(on5)c6ccccc6F" M24 SMILES_CANONICAL CACTVS 3.352 "Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P](O)(=O)OC(=O)c4cccc(c4)c5noc(n5)c6ccccc6F)[C@@H](O)[C@H]3O" M24 SMILES CACTVS 3.352 "Nc1ncnc2n(cnc12)[CH]3O[CH](CO[P](O)(=O)OC(=O)c4cccc(c4)c5noc(n5)c6ccccc6F)[CH](O)[CH]3O" M24 SMILES_CANONICAL "OpenEye OEToolkits" 1.7.0 "c1ccc(c(c1)c2nc(no2)c3cccc(c3)C(=O)O[P@](=O)(O)OC[C@@H]4[C@H]([C@H]([C@@H](O4)n5cnc6c5ncnc6N)O)O)F" M24 SMILES "OpenEye OEToolkits" 1.7.0 "c1ccc(c(c1)c2nc(no2)c3cccc(c3)C(=O)OP(=O)(O)OCC4C(C(C(O4)n5cnc6c5ncnc6N)O)O)F" M24 InChI InChI 1.03 "InChI=1S/C25H21FN7O9P/c26-15-7-2-1-6-14(15)23-31-21(32-41-23)12-4-3-5-13(8-12)25(36)42-43(37,38)39-9-16-18(34)19(35)24(40-16)33-11-30-17-20(27)28-10-29-22(17)33/h1-8,10-11,16,18-19,24,34-35H,9H2,(H,37,38)(H2,27,28,29)/t16-,18-,19-,24-/m1/s1" M24 InChIKey InChI 1.03 XGTSAMZIYGBAIU-VEBYGKHWSA-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 M24 "SYSTEMATIC NAME" ACDLabs 11.02 "5'-O-[(R)-[({3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]phenyl}carbonyl)oxy](hydroxy)phosphoryl]adenosine" M24 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.6.1 "[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl] 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]benzoate" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site M24 "Create component" 2009-07-29 RCSB M24 "Modify aromatic_flag" 2011-06-04 RCSB M24 "Modify descriptor" 2011-06-04 RCSB #