data_3FD # _chem_comp.id 3FD _chem_comp.name "4-[[(2R,3S,4R,5R)-5-[6-amino-8-[(3,4-dichlorophenyl)methylamino]purin-9-yl]-3,4-dihydroxy-oxolan-2-yl]methoxymethyl]benzonitrile" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C25 H23 Cl2 N7 O4" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2009-01-28 _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 556.401 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 3FD _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 3FZL _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site PDBJ # 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 3FD C18 C18 C 0 1 Y N N 20.577 -2.695 3.907 -4.160 -1.656 1.977 C18 3FD 1 3FD C17 C17 C 0 1 Y N N 21.472 -3.424 4.681 -4.929 -2.776 1.722 C17 3FD 2 3FD C16 C16 C 0 1 Y N N 22.813 -3.451 4.343 -5.932 -2.724 0.771 C16 3FD 3 3FD CL20 CL20 CL 0 0 N N N 23.906 -4.347 5.307 -6.898 -4.130 0.450 CL20 3FD 4 3FD C15 C15 C 0 1 Y N N 23.274 -2.768 3.219 -6.165 -1.551 0.075 C15 3FD 5 3FD C14 C14 C 0 1 Y N N 22.380 -2.035 2.433 -5.394 -0.431 0.331 C14 3FD 6 3FD C13 C13 C 0 1 Y N N 21.035 -1.992 2.779 -4.392 -0.484 1.282 C13 3FD 7 3FD C12 C12 C 0 1 N N N 20.055 -1.196 1.932 -3.554 0.736 1.562 C12 3FD 8 3FD N11 N11 N 0 1 N N N 18.750 -1.868 1.944 -2.382 0.735 0.683 N11 3FD 9 3FD C6 C6 C 0 1 Y N N 18.445 -2.744 0.986 -1.462 1.762 0.757 C6 3FD 10 3FD N7 N7 N 0 1 Y N N 19.267 -3.148 -0.002 -1.537 2.783 1.574 N7 3FD 11 3FD C8 C8 C 0 1 Y N N 18.596 -3.994 -0.773 -0.468 3.596 1.379 C8 3FD 12 3FD C4 C4 C 0 1 Y N N 18.945 -4.702 -1.882 -0.031 4.802 1.950 C4 3FD 13 3FD N10 N10 N 0 1 N N N 20.174 -4.593 -2.386 -0.761 5.416 2.955 N10 3FD 14 3FD N1 N1 N 0 1 Y N N 18.038 -5.501 -2.469 1.100 5.340 1.504 N1 3FD 15 3FD C2 C2 C 0 1 Y N N 16.808 -5.615 -1.961 1.802 4.762 0.548 C2 3FD 16 3FD N3 N3 N 0 1 Y N N 16.459 -4.940 -0.871 1.430 3.631 -0.016 N3 3FD 17 3FD C9 C9 C 0 1 Y N N 17.337 -4.131 -0.265 0.314 3.020 0.364 C9 3FD 18 3FD N5 N5 N 0 1 Y N N 17.246 -3.363 0.815 -0.332 1.863 -0.006 N5 3FD 19 3FD C21 C21 C 0 1 N N R 16.012 -3.207 1.690 0.109 0.914 -1.032 C21 3FD 20 3FD O22 O22 O 0 1 N N N 15.702 -1.807 1.863 1.527 0.670 -0.915 O22 3FD 21 3FD C24 C24 C 0 1 N N R 16.313 -3.699 3.088 -0.072 1.524 -2.441 C24 3FD 22 3FD O26 O26 O 0 1 N N N 16.142 -5.116 3.145 -1.281 1.052 -3.039 O26 3FD 23 3FD C25 C25 C 0 1 N N S 15.269 -3.058 3.911 1.156 1.016 -3.229 C25 3FD 24 3FD O27 O27 O 0 1 N N N 14.111 -3.870 3.893 0.744 0.216 -4.339 O27 3FD 25 3FD C23 C23 C 0 1 N N R 14.979 -1.716 3.188 1.934 0.161 -2.204 C23 3FD 26 3FD C28 C28 C 0 1 N N N 15.554 -0.509 4.006 3.441 0.339 -2.396 C28 3FD 27 3FD O29 O29 O 0 1 N N N 16.995 -0.626 4.057 4.141 -0.492 -1.468 O29 3FD 28 3FD C30 C30 C 0 1 N N N 17.555 0.347 4.946 5.564 -0.401 -1.564 C30 3FD 29 3FD C31 C31 C 0 1 Y N N 18.868 0.182 5.416 6.195 -1.314 -0.544 C31 3FD 30 3FD C32 C32 C 0 1 Y N N 19.865 1.069 5.015 6.487 -2.624 -0.881 C32 3FD 31 3FD C33 C33 C 0 1 Y N N 21.169 0.901 5.464 7.066 -3.465 0.047 C33 3FD 32 3FD C34 C34 C 0 1 Y N N 21.490 -0.164 6.320 7.357 -2.992 1.328 C34 3FD 33 3FD C37 C37 C 0 1 N N N 22.851 -0.319 6.798 7.957 -3.859 2.296 C37 3FD 34 3FD N38 N38 N 0 1 N N N 23.939 -0.437 7.139 8.434 -4.547 3.065 N38 3FD 35 3FD C35 C35 C 0 1 Y N N 20.493 -1.059 6.729 7.060 -1.668 1.661 C35 3FD 36 3FD C36 C36 C 0 1 Y N N 19.179 -0.888 6.280 6.486 -0.837 0.721 C36 3FD 37 3FD CL21 CL21 CL 0 0 N N N 24.961 -2.834 2.799 -7.422 -1.484 -1.120 CL21 3FD 38 3FD H18 H18 H 0 1 N N N 19.530 -2.669 4.172 -3.380 -1.696 2.723 H18 3FD 39 3FD H17 H17 H 0 1 N N N 21.121 -3.969 5.545 -4.747 -3.691 2.265 H17 3FD 40 3FD H14 H14 H 0 1 N N N 22.733 -1.505 1.561 -5.575 0.485 -0.212 H14 3FD 41 3FD H12 H12 H 0 1 N N N 19.951 -0.182 2.345 -4.145 1.634 1.378 H12 3FD 42 3FD H12A H12A H 0 0 N N N 20.428 -1.131 0.899 -3.228 0.723 2.602 H12A 3FD 43 3FD HN11 HN11 H 0 0 N N N 18.705 -2.372 2.806 -2.252 0.013 0.048 HN11 3FD 44 3FD HN10 HN10 H 0 0 N N N 20.124 -4.566 -3.384 -1.584 5.013 3.272 HN10 3FD 45 3FD HN1A HN1A H 0 0 N N N 20.598 -3.752 -2.050 -0.449 6.249 3.341 HN1A 3FD 46 3FD H2 H2 H 0 1 N N N 16.089 -6.263 -2.441 2.715 5.233 0.215 H2 3FD 47 3FD H21 H21 H 0 1 N N N 15.194 -3.763 1.208 -0.446 -0.020 -0.947 H21 3FD 48 3FD H24 H24 H 0 1 N N N 17.338 -3.467 3.414 -0.072 2.612 -2.389 H24 3FD 49 3FD HO26 HO26 H 0 0 N N N 16.104 -5.467 2.263 -1.444 1.403 -3.925 HO26 3FD 50 3FD H25 H25 H 0 1 N N N 15.571 -2.913 4.959 1.765 1.855 -3.569 H25 3FD 51 3FD HO27 HO27 H 0 0 N N N 13.837 -4.052 4.784 0.200 0.689 -4.984 HO27 3FD 52 3FD H23 H23 H 0 1 N N N 13.897 -1.554 3.071 1.659 -0.890 -2.301 H23 3FD 53 3FD H28 H28 H 0 1 N N N 15.276 0.436 3.517 3.714 0.057 -3.413 H28 3FD 54 3FD H28A H28A H 0 0 N N N 15.142 -0.518 5.026 3.709 1.381 -2.224 H28A 3FD 55 3FD H30 H30 H 0 1 N N N 17.541 1.304 4.403 5.880 -0.698 -2.563 H30 3FD 56 3FD H30A H30A H 0 0 N N N 16.938 0.262 5.853 5.875 0.626 -1.374 H30A 3FD 57 3FD H32 H32 H 0 1 N N N 19.624 1.888 4.354 6.262 -2.989 -1.872 H32 3FD 58 3FD H33 H33 H 0 1 N N N 21.938 1.592 5.153 7.292 -4.488 -0.216 H33 3FD 59 3FD H35 H35 H 0 1 N N N 20.738 -1.878 7.389 7.282 -1.296 2.649 H35 3FD 60 3FD H36 H36 H 0 1 N N N 18.406 -1.573 6.594 6.260 0.188 0.976 H36 3FD 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 3FD C18 C17 DOUB Y N 1 3FD C18 C13 SING Y N 2 3FD C17 C16 SING Y N 3 3FD C16 CL20 SING N N 4 3FD C16 C15 DOUB Y N 5 3FD C15 C14 SING Y N 6 3FD C15 CL21 SING N N 7 3FD C14 C13 DOUB Y N 8 3FD C13 C12 SING N N 9 3FD C12 N11 SING N N 10 3FD N11 C6 SING N N 11 3FD C6 N7 DOUB Y N 12 3FD C6 N5 SING Y N 13 3FD N7 C8 SING Y N 14 3FD C8 C4 DOUB Y N 15 3FD C8 C9 SING Y N 16 3FD C4 N10 SING N N 17 3FD C4 N1 SING Y N 18 3FD N1 C2 DOUB Y N 19 3FD C2 N3 SING Y N 20 3FD N3 C9 DOUB Y N 21 3FD C9 N5 SING Y N 22 3FD N5 C21 SING N N 23 3FD C21 O22 SING N N 24 3FD C21 C24 SING N N 25 3FD O22 C23 SING N N 26 3FD C24 O26 SING N N 27 3FD C24 C25 SING N N 28 3FD C25 O27 SING N N 29 3FD C25 C23 SING N N 30 3FD C23 C28 SING N N 31 3FD C28 O29 SING N N 32 3FD O29 C30 SING N N 33 3FD C30 C31 SING N N 34 3FD C31 C32 DOUB Y N 35 3FD C31 C36 SING Y N 36 3FD C32 C33 SING Y N 37 3FD C33 C34 DOUB Y N 38 3FD C34 C37 SING N N 39 3FD C34 C35 SING Y N 40 3FD C37 N38 TRIP N N 41 3FD C35 C36 DOUB Y N 42 3FD C18 H18 SING N N 43 3FD C17 H17 SING N N 44 3FD C14 H14 SING N N 45 3FD C12 H12 SING N N 46 3FD C12 H12A SING N N 47 3FD N11 HN11 SING N N 48 3FD N10 HN10 SING N N 49 3FD N10 HN1A SING N N 50 3FD C2 H2 SING N N 51 3FD C21 H21 SING N N 52 3FD C24 H24 SING N N 53 3FD O26 HO26 SING N N 54 3FD C25 H25 SING N N 55 3FD O27 HO27 SING N N 56 3FD C23 H23 SING N N 57 3FD C28 H28 SING N N 58 3FD C28 H28A SING N N 59 3FD C30 H30 SING N N 60 3FD C30 H30A SING N N 61 3FD C32 H32 SING N N 62 3FD C33 H33 SING N N 63 3FD C35 H35 SING N N 64 3FD C36 H36 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 3FD SMILES ACDLabs 10.04 "Clc1ccc(cc1Cl)CNc3nc2c(ncnc2n3C4OC(C(O)C4O)COCc5ccc(C#N)cc5)N" 3FD SMILES_CANONICAL CACTVS 3.341 "Nc1ncnc2n([C@@H]3O[C@H](COCc4ccc(cc4)C#N)[C@@H](O)[C@H]3O)c(NCc5ccc(Cl)c(Cl)c5)nc12" 3FD SMILES CACTVS 3.341 "Nc1ncnc2n([CH]3O[CH](COCc4ccc(cc4)C#N)[CH](O)[CH]3O)c(NCc5ccc(Cl)c(Cl)c5)nc12" 3FD SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1cc(ccc1COC[C@@H]2[C@H]([C@H]([C@@H](O2)n3c4c(c(ncn4)N)nc3NCc5ccc(c(c5)Cl)Cl)O)O)C#N" 3FD SMILES "OpenEye OEToolkits" 1.5.0 "c1cc(ccc1COCC2C(C(C(O2)n3c4c(c(ncn4)N)nc3NCc5ccc(c(c5)Cl)Cl)O)O)C#N" 3FD InChI InChI 1.03 "InChI=1S/C25H23Cl2N7O4/c26-16-6-5-15(7-17(16)27)9-30-25-33-19-22(29)31-12-32-23(19)34(25)24-21(36)20(35)18(38-24)11-37-10-14-3-1-13(8-28)2-4-14/h1-7,12,18,20-21,24,35-36H,9-11H2,(H,30,33)(H2,29,31,32)/t18-,20-,21-,24-/m1/s1" 3FD InChIKey InChI 1.03 ZXGGCBQORXDVTE-UMCMBGNQSA-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 3FD "SYSTEMATIC NAME" ACDLabs 10.04 "5'-O-(4-cyanobenzyl)-8-[(3,4-dichlorobenzyl)amino]adenosine" 3FD "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "4-[[(2R,3S,4R,5R)-5-[6-amino-8-[(3,4-dichlorophenyl)methylamino]purin-9-yl]-3,4-dihydroxy-oxolan-2-yl]methoxymethyl]benzonitrile" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 3FD "Create component" 2009-01-28 PDBJ 3FD "Modify aromatic_flag" 2011-06-04 RCSB 3FD "Modify descriptor" 2011-06-04 RCSB #