data_FHA
# 
_chem_comp.id                                    FHA 
_chem_comp.name                                  "2'-deoxy-5'-O-[(S)-{(S)-fluoro[(S)-hydroxy(phosphonooxy)phosphoryl]methyl}(hydroxy)phosphoryl]adenosine" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C11 H17 F N5 O11 P3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2011-09-07 
_chem_comp.pdbx_modified_date                    2012-03-16 
_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                        507.199 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     FHA 
_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        3TFS 
_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 
FHA N1     N1     N 0 1 Y N N 9.641  8.331  8.249  -8.320 -1.980 -0.816 N1     FHA 1  
FHA C2     C2     C 0 1 Y N N 8.407  8.431  7.691  -7.896 -1.056 -1.659 C2     FHA 2  
FHA N3     N3     N 0 1 Y N N 7.183  8.233  8.233  -6.764 -0.407 -1.485 N3     FHA 3  
FHA C4     C4     C 0 1 Y N N 7.296  7.896  9.556  -5.991 -0.662 -0.434 C4     FHA 4  
FHA C5     C5     C 0 1 Y N N 8.514  7.757  10.264 -6.399 -1.637 0.492  C5     FHA 5  
FHA C6     C6     C 0 1 Y N N 9.704  7.989  9.577  -7.615 -2.303 0.263  C6     FHA 6  
FHA N6     N6     N 0 1 N N N 10.904 7.819  10.203 -8.067 -3.273 1.141  N6     FHA 7  
FHA N7     N7     N 0 1 Y N N 8.301  7.385  11.598 -5.445 -1.699 1.452  N7     FHA 8  
FHA C8     C8     C 0 1 Y N N 6.979  7.308  11.689 -4.501 -0.845 1.180  C8     FHA 9  
FHA N9     N9     N 0 1 Y N N 6.310  7.615  10.488 -4.792 -0.181 0.026  N9     FHA 10 
FHA PA     PA     P 0 1 N N N 4.975  5.445  15.030 1.764  1.242  0.524  PA     FHA 11 
FHA PB     PB     P 0 1 N N N 3.760  2.681  14.093 4.473  0.041  0.242  PB     FHA 12 
FHA PG     PG     P 0 1 N N N 3.869  1.241  16.509 6.920  -1.432 -0.552 PG     FHA 13 
FHA "C1'"  "C1'"  C 0 1 N N R 4.891  7.523  10.152 -3.973 0.856  -0.607 "C1'"  FHA 14 
FHA F1A    F1A    F 0 1 N N N 6.216  3.636  13.532 2.234  -1.144 -0.507 F1A    FHA 15 
FHA O1A    O1A    O 0 1 N N N 3.725  5.533  15.960 1.667  0.670  2.026  O1A    FHA 16 
FHA O1B    O1B    O 0 1 N N N 3.995  2.254  12.597 4.384  -0.485 1.622  O1B    FHA 17 
FHA O1G    O1G    O 0 1 N N N 5.151  0.571  17.082 7.400  -1.977 -1.988 O1G    FHA 18 
FHA "C2'"  "C2'"  C 0 1 N N N 4.521  6.111  9.652  -4.403 2.256  -0.114 "C2'"  FHA 19 
FHA O2A    O2A    O 0 1 N N N 6.186  5.973  15.712 2.366  2.594  0.550  O2A    FHA 20 
FHA O2B    O2B    O 0 1 N N N 2.489  3.318  14.423 5.128  1.512  0.269  O2B    FHA 21 
FHA O2G    O2G    O 0 1 N N N 2.729  0.215  16.833 7.779  -0.298 -0.142 O2G    FHA 22 
FHA "C3'"  "C3'"  C 0 1 N N S 4.177  5.440  11.012 -3.076 3.039  -0.007 "C3'"  FHA 23 
FHA "O3'"  "O3'"  O 0 1 N N N 3.353  4.333  10.878 -3.087 4.167  -0.886 "O3'"  FHA 24 
FHA C3A    C3A    C 0 1 N N S 5.252  3.721  14.503 2.803  0.133  -0.483 C3A    FHA 25 
FHA O3B    O3B    O 0 1 N N N 3.938  1.367  14.941 5.390  -0.938 -0.648 O3B    FHA 26 
FHA O3G    O3G    O 0 1 N N N 3.581  2.620  16.915 7.035  -2.613 0.536  O3G    FHA 27 
FHA "C4'"  "C4'"  C 0 1 N N R 3.382  6.582  11.682 -2.001 2.021  -0.449 "C4'"  FHA 28 
FHA "O4'"  "O4'"  O 0 1 N N N 4.079  7.757  11.281 -2.594 0.728  -0.199 "O4'"  FHA 29 
FHA "C5'"  "C5'"  C 0 1 N N N 3.288  6.443  13.201 -0.729 2.193  0.384  "C5'"  FHA 30 
FHA "O5'"  "O5'"  O 0 1 N N N 4.591  6.406  13.754 0.289  1.324  -0.115 "O5'"  FHA 31 
FHA H2     H2     H 0 1 N N N 8.402  8.714  6.649  -8.500 -0.825 -2.524 H2     FHA 32 
FHA HN6    HN6    H 0 1 N N N 11.646 7.981  9.552  -8.908 -3.726 0.971  HN6    FHA 33 
FHA HN6A   HN6A   H 0 0 N N N 10.979 8.467  10.961 -7.543 -3.500 1.925  HN6A   FHA 34 
FHA H8     H8     H 0 1 N N N 6.464  7.036  12.599 -3.617 -0.686 1.781  H8     FHA 35 
FHA "H1'"  "H1'"  H 0 1 N N N 4.719  8.280  9.373  -4.055 0.793  -1.692 "H1'"  FHA 36 
FHA HO1A   HO1A   H 0 0 N N N 3.977  5.911  16.794 1.281  -0.215 2.085  HO1A   FHA 37 
FHA HO1G   HO1G   H 0 0 N N N 4.925  -0.265 17.472 8.314  -2.291 -2.005 HO1G   FHA 38 
FHA "H2'"  "H2'"  H 0 1 N N N 3.675  6.113  8.949  -5.068 2.728  -0.837 "H2'"  FHA 39 
FHA "H2'A" "H2'A" H 0 0 N N N 5.348  5.612  9.125  -4.885 2.186  0.861  "H2'A" FHA 40 
FHA HO2B   HO2B   H 0 0 N N N 1.956  3.387  13.640 5.217  1.919  -0.603 HO2B   FHA 41 
FHA "H3'"  "H3'"  H 0 1 N N N 5.063  5.068  11.548 -2.901 3.357  1.021  "H3'"  FHA 42 
FHA "HO3'" "HO3'" H 0 0 N N N 3.624  3.660  11.491 -3.783 4.810  -0.691 "HO3'" FHA 43 
FHA H3A    H3A    H 0 1 N N N 5.613  3.250  15.429 2.868  0.521  -1.499 H3A    FHA 44 
FHA HO3G   HO3G   H 0 0 N N N 2.722  2.659  17.320 6.497  -3.390 0.332  HO3G   FHA 45 
FHA "H4'"  "H4'"  H 0 1 N N N 2.327  6.588  11.370 -1.779 2.139  -1.509 "H4'"  FHA 46 
FHA "H5'"  "H5'"  H 0 1 N N N 2.739  7.302  13.614 -0.389 3.227  0.318  "H5'"  FHA 47 
FHA "H5'A" "H5'A" H 0 0 N N N 2.757  5.513  13.452 -0.940 1.946  1.425  "H5'A" FHA 48 
# 
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 
FHA C2    N1     DOUB Y N 1  
FHA N1    C6     SING Y N 2  
FHA C2    N3     SING Y N 3  
FHA C2    H2     SING N N 4  
FHA N3    C4     DOUB Y N 5  
FHA C4    C5     SING Y N 6  
FHA C4    N9     SING Y N 7  
FHA C6    C5     DOUB Y N 8  
FHA C5    N7     SING Y N 9  
FHA C6    N6     SING N N 10 
FHA N6    HN6    SING N N 11 
FHA N6    HN6A   SING N N 12 
FHA N7    C8     DOUB Y N 13 
FHA N9    C8     SING Y N 14 
FHA C8    H8     SING N N 15 
FHA "C1'" N9     SING N N 16 
FHA "O5'" PA     SING N N 17 
FHA C3A   PA     SING N N 18 
FHA PA    O2A    DOUB N N 19 
FHA PA    O1A    SING N N 20 
FHA O1B   PB     DOUB N N 21 
FHA PB    O2B    SING N N 22 
FHA PB    C3A    SING N N 23 
FHA PB    O3B    SING N N 24 
FHA O3B   PG     SING N N 25 
FHA PG    O2G    DOUB N N 26 
FHA PG    O3G    SING N N 27 
FHA PG    O1G    SING N N 28 
FHA "C2'" "C1'"  SING N N 29 
FHA "C1'" "O4'"  SING N N 30 
FHA "C1'" "H1'"  SING N N 31 
FHA F1A   C3A    SING N N 32 
FHA O1A   HO1A   SING N N 33 
FHA O1G   HO1G   SING N N 34 
FHA "C2'" "C3'"  SING N N 35 
FHA "C2'" "H2'"  SING N N 36 
FHA "C2'" "H2'A" SING N N 37 
FHA O2B   HO2B   SING N N 38 
FHA "O3'" "C3'"  SING N N 39 
FHA "C3'" "C4'"  SING N N 40 
FHA "C3'" "H3'"  SING N N 41 
FHA "O3'" "HO3'" SING N N 42 
FHA C3A   H3A    SING N N 43 
FHA O3G   HO3G   SING N N 44 
FHA "O4'" "C4'"  SING N N 45 
FHA "C4'" "C5'"  SING N N 46 
FHA "C4'" "H4'"  SING N N 47 
FHA "C5'" "O5'"  SING N N 48 
FHA "C5'" "H5'"  SING N N 49 
FHA "C5'" "H5'A" SING N N 50 
# 
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 
FHA SMILES           ACDLabs              12.01 "O=P(O)(O)OP(=O)(O)C(F)P(=O)(O)OCC3OC(n2cnc1c(ncnc12)N)CC3O"                                                                                                                                             
FHA InChI            InChI                1.03  "InChI=1S/C11H17FN5O11P3/c12-11(30(21,22)28-31(23,24)25)29(19,20)26-2-6-5(18)1-7(27-6)17-4-16-8-9(13)14-3-15-10(8)17/h3-7,11,18H,1-2H2,(H,19,20)(H,21,22)(H2,13,14,15)(H2,23,24,25)/t5-,6+,7+,11-/m0/s1" 
FHA InChIKey         InChI                1.03  HAJKJTDYTZCDDL-LLVCWYDASA-N                                                                                                                                                                              
FHA SMILES_CANONICAL CACTVS               3.370 "Nc1ncnc2n(cnc12)[C@H]3C[C@H](O)[C@@H](CO[P](O)(=O)[C@H](F)[P](O)(=O)O[P](O)(O)=O)O3"                                                                                                                    
FHA SMILES           CACTVS               3.370 "Nc1ncnc2n(cnc12)[CH]3C[CH](O)[CH](CO[P](O)(=O)[CH](F)[P](O)(=O)O[P](O)(O)=O)O3"                                                                                                                         
FHA SMILES_CANONICAL "OpenEye OEToolkits" 1.7.2 "c1nc(c2c(n1)n(cn2)[C@H]3C[C@@H]([C@H](O3)CO[P@](=O)([C@H](F)[P@](=O)(O)OP(=O)(O)O)O)O)N"                                                                                                                
FHA SMILES           "OpenEye OEToolkits" 1.7.2 "c1nc(c2c(n1)n(cn2)C3CC(C(O3)COP(=O)(C(F)P(=O)(O)OP(=O)(O)O)O)O)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 
FHA "SYSTEMATIC NAME" ACDLabs              12.01 "2'-deoxy-5'-O-[(S)-{(S)-fluoro[(S)-hydroxy(phosphonooxy)phosphoryl]methyl}(hydroxy)phosphoryl]adenosine"                                  
FHA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.2 "[(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-oxidanyl-oxolan-2-yl]methoxy-[(S)-fluoranyl-[oxidanyl(phosphonooxy)phosphoryl]methyl]phosphinic acid" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
FHA "Create component" 2011-09-07 RCSB 
# 
