data_F2A
# 
_chem_comp.id                                    F2A 
_chem_comp.name                                  "2'-deoxy-5'-O-[(S)-hydroxy{[(S)-hydroxy(phosphonooxy)phosphoryl]methyl}phosphoryl]adenosine" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C11 H18 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                     2008-02-04 
_chem_comp.pdbx_modified_date                    2008-10-14 
_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                        489.209 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     F2A 
_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        3C2L 
_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 
F2A PA     PA     P 0 1 N N S -3.842 -3.880  34.388 1.818  1.110  0.534  PA     F2A 1  
F2A O1A    O1A    O 0 1 N N N -5.063 -3.623  35.200 1.668  0.387  1.964  O1A    F2A 2  
F2A O2A    O2A    O 0 1 N N N -2.533 -3.360  34.853 2.405  2.455  0.720  O2A    F2A 3  
F2A C3A    C3A    C 0 1 N N N -3.673 -5.749  34.435 2.907  0.115  -0.538 C3A    F2A 4  
F2A "O5'"  "O5'"  O 0 1 N N N -4.067 -3.289  32.925 0.368  1.247  -0.153 "O5'"  F2A 5  
F2A PB     PB     P 0 1 N N S -4.768 -7.073  33.688 4.548  -0.041 0.240  PB     F2A 6  
F2A O1B    O1B    O 0 1 N N N -4.315 -7.232  32.281 4.410  -0.705 1.555  O1B    F2A 7  
F2A O2B    O2B    O 0 1 N N N -6.175 -6.676  33.970 5.187  1.423  0.442  O2B    F2A 8  
F2A O3B    O3B    O 0 1 N N N -4.465 -8.342  34.423 5.509  -0.919 -0.707 O3B    F2A 9  
F2A PG     PG     P 0 1 N N N -4.432 -8.357  35.915 7.039  -1.411 -0.600 PG     F2A 10 
F2A O1G    O1G    O 0 1 N N N -2.991 -8.444  36.260 7.870  -0.320 -0.044 O1G    F2A 11 
F2A O2G    O2G    O 0 1 N N N -5.375 -9.385  36.429 7.123  -2.696 0.366  O2G    F2A 12 
F2A O3G    O3G    O 0 1 N N N -4.946 -7.053  36.409 7.580  -1.804 -2.065 O3G    F2A 13 
F2A "C5'"  "C5'"  C 0 1 N N N -5.206 -3.642  32.146 -0.677 2.055  0.391  "C5'"  F2A 14 
F2A "C4'"  "C4'"  C 0 1 N N R -4.960 -3.338  30.687 -1.913 1.961  -0.505 "C4'"  F2A 15 
F2A "O4'"  "O4'"  O 0 1 N N N -4.223 -2.097  30.548 -2.493 0.640  -0.434 "O4'"  F2A 16 
F2A "C1'"  "C1'"  C 0 1 N N R -3.402 -2.161  29.388 -3.862 0.760  -0.855 "C1'"  F2A 17 
F2A N9     N9     N 0 1 Y N N -2.006 -1.932  29.776 -4.697 -0.187 -0.110 N9     F2A 18 
F2A C4     C4     C 0 1 Y N N -1.002 -1.476  28.952 -5.906 -0.695 -0.513 C4     F2A 19 
F2A N3     N3     N 0 1 Y N N -1.101 -1.135  27.658 -6.677 -0.543 -1.584 N3     F2A 20 
F2A C2     C2     C 0 1 Y N N 0.081  -0.754  27.181 -7.821 -1.188 -1.684 C2     F2A 21 
F2A N1     N1     N 0 1 Y N N 1.262  -0.680  27.803 -8.258 -2.005 -0.744 N1     F2A 22 
F2A C6     C6     C 0 1 Y N N 1.329  -1.022  29.106 -7.555 -2.219 0.363  C6     F2A 23 
F2A N6     N6     N 0 1 N N N 2.507  -0.936  29.730 -8.022 -3.078 1.343  N6     F2A 24 
F2A C5     C5     C 0 1 Y N N 0.145  -1.448  29.731 -6.327 -1.554 0.516  C5     F2A 25 
F2A N7     N7     N 0 1 Y N N -0.127 -1.868  31.025 -5.371 -1.527 1.475  N7     F2A 26 
F2A C8     C8     C 0 1 Y N N -1.413 -2.138  31.004 -4.411 -0.729 1.108  C8     F2A 27 
F2A "C2'"  "C2'"  C 0 1 N N N -3.622 -3.539  28.760 -4.310 2.203  -0.553 "C2'"  F2A 28 
F2A "C3'"  "C3'"  C 0 1 N N S -4.087 -4.343  29.964 -3.042 2.884  0.022  "C3'"  F2A 29 
F2A "O3'"  "O3'"  O 0 1 N N N -4.868 -5.460  29.571 -2.901 4.212  -0.487 "O3'"  F2A 30 
F2A HO1A   HO1A   H 0 0 N N N -4.827 -3.568  36.119 1.288  -0.501 1.918  HO1A   F2A 31 
F2A H3A    H3A    H 0 1 N N N -2.701 -5.925  33.951 2.474  -0.876 -0.675 H3A    F2A 32 
F2A H3AA   H3AA   H 0 0 N N N -3.929 -5.907  35.493 3.008  0.604  -1.507 H3AA   F2A 33 
F2A HO2B   HO2B   H 0 0 N N N -6.299 -6.591  34.908 5.306  1.918  -0.380 HO2B   F2A 34 
F2A HO2G   HO2G   H 0 0 N N N -5.576 -10.005 35.738 6.601  -3.451 0.063  HO2G   F2A 35 
F2A HO3G   HO3G   H 0 0 N N N -5.056 -7.092  37.352 8.497  -2.110 -2.076 HO3G   F2A 36 
F2A "H5'"  "H5'"  H 0 1 N N N -5.404 -4.718  32.262 -0.926 1.702  1.392  "H5'"  F2A 37 
F2A "H5'A" "H5'A" H 0 0 N N N -6.071 -3.057  32.492 -0.345 3.092  0.443  "H5'A" F2A 38 
F2A "H4'"  "H4'"  H 0 1 N N N -5.972 -3.328  30.256 -1.660 2.214  -1.535 "H4'"  F2A 39 
F2A "H1'"  "H1'"  H 0 1 N N N -3.657 -1.388  28.648 -3.941 0.561  -1.924 "H1'"  F2A 40 
F2A H2     H2     H 0 1 N N N 0.087  -0.462  26.141 -8.424 -1.042 -2.569 H2     F2A 41 
F2A HN6    HN6    H 0 1 N N N 3.243  -0.915  29.053 -8.872 -3.531 1.226  HN6    F2A 42 
F2A HN6A   HN6A   H 0 0 N N N 2.534  -0.100  30.278 -7.500 -3.226 2.147  HN6A   F2A 43 
F2A H8     H8     H 0 1 N N N -1.956 -2.489  31.869 -3.520 -0.524 1.684  H8     F2A 44 
F2A "H2'"  "H2'"  H 0 1 N N N -4.374 -3.517  27.957 -4.627 2.704  -1.468 "H2'"  F2A 45 
F2A "H2'A" "H2'A" H 0 0 N N N -2.732 -3.952  28.263 -5.114 2.207  0.184  "H2'A" F2A 46 
F2A "H3'"  "H3'"  H 0 1 N N N -3.258 -4.751  30.561 -3.061 2.886  1.112  "H3'"  F2A 47 
F2A "HO3'" "HO3'" H 0 0 N N N -5.043 -5.413  28.638 -3.632 4.801  -0.256 "HO3'" F2A 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 
F2A "O5'" PA     SING N N 1  
F2A PA    C3A    SING N N 2  
F2A PA    O2A    DOUB N N 3  
F2A PA    O1A    SING N N 4  
F2A O1A   HO1A   SING N N 5  
F2A PB    C3A    SING N N 6  
F2A C3A   H3A    SING N N 7  
F2A C3A   H3AA   SING N N 8  
F2A "C5'" "O5'"  SING N N 9  
F2A O1B   PB     DOUB N N 10 
F2A PB    O2B    SING N N 11 
F2A PB    O3B    SING N N 12 
F2A O2B   HO2B   SING N N 13 
F2A O3B   PG     SING N N 14 
F2A PG    O1G    DOUB N N 15 
F2A PG    O3G    SING N N 16 
F2A PG    O2G    SING N N 17 
F2A O2G   HO2G   SING N N 18 
F2A O3G   HO3G   SING N N 19 
F2A "C4'" "C5'"  SING N N 20 
F2A "C5'" "H5'"  SING N N 21 
F2A "C5'" "H5'A" SING N N 22 
F2A "C3'" "C4'"  SING N N 23 
F2A "O4'" "C4'"  SING N N 24 
F2A "C4'" "H4'"  SING N N 25 
F2A "C1'" "O4'"  SING N N 26 
F2A "C2'" "C1'"  SING N N 27 
F2A "C1'" N9     SING Y N 28 
F2A "C1'" "H1'"  SING Y N 29 
F2A C4    N9     SING Y N 30 
F2A N9    C8     SING Y N 31 
F2A N3    C4     DOUB Y N 32 
F2A C4    C5     SING Y N 33 
F2A C2    N3     SING N N 34 
F2A C2    N1     DOUB Y N 35 
F2A C2    H2     SING N N 36 
F2A N1    C6     SING Y N 37 
F2A C6    N6     SING N N 38 
F2A C6    C5     DOUB N N 39 
F2A N6    HN6    SING Y N 40 
F2A N6    HN6A   SING Y N 41 
F2A C5    N7     SING N N 42 
F2A C8    N7     DOUB N N 43 
F2A C8    H8     SING N N 44 
F2A "C2'" "C3'"  SING N N 45 
F2A "C2'" "H2'"  SING N N 46 
F2A "C2'" "H2'A" SING N N 47 
F2A "O3'" "C3'"  SING N N 48 
F2A "C3'" "H3'"  SING N N 49 
F2A "O3'" "HO3'" 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 
F2A SMILES           ACDLabs              10.04 O=P(O)(O)OP(=O)(O)CP(=O)(O)OCC3OC(n2cnc1c(ncnc12)N)CC3O 
F2A InChI            InChI                1.02b 
InChI=1/C11H18N5O11P3/c12-10-9-11(14-3-13-10)16(4-15-9)8-1-6(17)7(26-8)2-25-28(18,19)5-29(20,21)27-30(22,23)24/h3-4,6-8,17H,1-2,5H2,(H,18,19)(H,20,21)(H2,12,13,14)(H2,22,23,24)/t6-,7+,8+/m0/s1/f/h18,20,22-23H,12H2 
F2A InChIKey         InChI                1.02b XETARULVTCYJAN-DAPWCNBDDJ 
F2A SMILES_CANONICAL CACTVS               3.341 Nc1ncnc2n(cnc12)[C@H]3C[C@H](O)[C@@H](CO[P@](O)(=O)C[P@@](O)(=O)O[P](O)(O)=O)O3 
F2A SMILES           CACTVS               3.341 Nc1ncnc2n(cnc12)[CH]3C[CH](O)[CH](CO[P](O)(=O)C[P](O)(=O)O[P](O)(O)=O)O3 
F2A SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)[C@H]3C[C@@H]([C@H](O3)CO[P@](=O)(C[P@](=O)(O)OP(=O)(O)O)O)O)N 
F2A SMILES           "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)C3CC(C(O3)COP(=O)(CP(=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 
F2A "SYSTEMATIC NAME" ACDLabs              10.04 "2'-deoxy-5'-O-[(S)-hydroxy{[(S)-hydroxy(phosphonooxy)phosphoryl]methyl}phosphoryl]adenosine"                              
F2A "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-oxolan-2-yl]methoxy-[(hydroxy-phosphonooxy-phosphoryl)methyl]phosphinic acid" 
# 
