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                    2009-03-13 
_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                        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 N N 3  
3FD C16 CL20 SING Y N 4  
3FD C16 C15  DOUB N N 5  
3FD C15 C14  SING N N 6  
3FD C15 CL21 SING Y N 7  
3FD C14 C13  DOUB Y N 8  
3FD C13 C12  SING N N 9  
3FD C12 N11  SING Y N 10 
3FD N11 C6   SING N N 11 
3FD C6  N7   DOUB N N 12 
3FD C6  N5   SING N N 13 
3FD N7  C8   SING N N 14 
3FD C8  C4   DOUB N N 15 
3FD C8  C9   SING N 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 Y N 24 
3FD C21 C24  SING N N 25 
3FD O22 C23  SING N N 26 
3FD C24 O26  SING Y N 27 
3FD C24 C25  SING Y N 28 
3FD C25 O27  SING N N 29 
3FD C25 C23  SING Y N 30 
3FD C23 C28  SING Y 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 N N 35 
3FD C31 C36  SING N N 36 
3FD C32 C33  SING N N 37 
3FD C33 C34  DOUB N N 38 
3FD C34 C37  SING N N 39 
3FD C34 C35  SING N N 40 
3FD C37 N38  TRIP N N 41 
3FD C35 C36  DOUB N 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 Y N 54 
3FD C25 H25  SING Y N 55 
3FD O27 HO27 SING Y N 56 
3FD C23 H23  SING N N 57 
3FD C28 H28  SING Y N 58 
3FD C28 H28A SING N N 59 
3FD C30 H30  SING N N 60 
3FD C30 H30A SING Y N 61 
3FD C32 H32  SING N N 62 
3FD C33 H33  SING Y 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 InChI            InChI                1.02b 
InChI=1/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/f/h30H,29H2 
3FD InChIKey         InChI                1.02b ZXGGCBQORXDVTE-DPOHIZBKDH 
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 
# 
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 
# 
