data_AFH
# 
_chem_comp.id                                    AFH 
_chem_comp.name                                  
;ADENOSINE-5'-DIPHOSPHATE-2-DEOXY-2-FLUORO HEPTOSE
;
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C17 H26 F N5 O15 P2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "[(2R,3S,4R,5R)-5-(6-AMINO-9H-PURIN-9-YL)-3,4-DIHYDROXYTETRAHYDROFURAN-2-YL]METHYL (2S,3R,4S,5S,6R)-6-[(1S)-1,2-DIHYDROXYETHYL]-3-FLUORO-4,5-DIHYDROXYTETRAHYDRO-2H-PYRAN-2-YL DIHYDROGEN DIPHOSPHATE" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-07-24 
_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                        621.359 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AFH 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        ? 
_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 
AFH N9     N9     N 0 1 Y N N 47.797 11.774 5.569  6.100  0.394  0.098  N9     AFH 1  
AFH C8     C8     C 0 1 Y N N 48.721 10.976 4.961  5.578  1.301  0.970  C8     AFH 2  
AFH N7     N7     N 0 1 Y N N 49.790 10.855 5.727  6.487  2.171  1.304  N7     AFH 3  
AFH C5     C5     C 0 1 Y N N 49.598 11.549 6.830  7.648  1.875  0.673  C5     AFH 4  
AFH C6     C6     C 0 1 Y N N 50.342 11.831 8.027  8.930  2.449  0.641  C6     AFH 5  
AFH N6     N6     N 0 1 N N N 51.557 11.296 8.156  9.220  3.577  1.389  N6     AFH 6  
AFH N1     N1     N 0 1 Y N N 49.801 12.654 9.052  9.860  1.881  -0.120 N1     AFH 7  
AFH C2     C2     C 0 1 Y N N 48.545 13.219 8.938  9.593  0.805  -0.838 C2     AFH 8  
AFH N3     N3     N 0 1 Y N N 47.821 12.957 7.783  8.405  0.236  -0.844 N3     AFH 9  
AFH C4     C4     C 0 1 Y N N 48.289 12.156 6.733  7.413  0.734  -0.113 C4     AFH 10 
AFH C1D    C1*    C 0 1 N N R 46.434 12.187 5.059  5.391  -0.738 -0.504 C1D    AFH 11 
AFH C2D    C2*    C 0 1 N N R 46.513 12.858 3.686  5.598  -2.014 0.341  C2D    AFH 12 
AFH "O2'"  O2*    O 0 1 N N N 46.987 14.205 3.685  6.628  -2.831 -0.219 "O2'"  AFH 13 
AFH C3D    C3*    C 0 1 N N S 45.121 12.662 3.148  4.233  -2.737 0.268  C3D    AFH 14 
AFH C4D    C4*    C 0 1 N N R 44.755 11.349 3.708  3.365  -1.813 -0.615 C4D    AFH 15 
AFH O4D    O4*    O 0 1 N N N 45.568 11.081 4.867  3.965  -0.506 -0.483 O4D    AFH 16 
AFH O3D    O3*    O 0 1 N N N 44.180 13.653 3.596  4.377  -4.021 -0.342 O3D    AFH 17 
AFH C5D    C5*    C 0 1 N N N 44.891 10.349 2.571  1.922  -1.790 -0.109 C5D    AFH 18 
AFH O5D    O5*    O 0 1 N N N 43.707 10.448 1.697  1.129  -0.965 -0.966 O5D    AFH 19 
AFH PA     PA     P 0 1 N N S 42.592 9.373  1.484  -0.369 -0.987 -0.377 PA     AFH 20 
AFH O1A    O1A    O 0 1 N N N 41.925 9.591  0.259  -0.347 -0.571 1.043  O1A    AFH 21 
AFH O2A    O2A    O 0 1 N N N 41.583 9.363  2.545  -0.969 -2.476 -0.491 O2A    AFH 22 
AFH O3A    O3A    O 0 1 N N N 43.421 8.102  1.309  -1.291 0.029  -1.220 O3A    AFH 23 
AFH PB     PB     P 0 1 N N S 43.177 6.634  1.242  -2.569 0.368  -0.301 PB     AFH 24 
AFH O1B    O1B    O 0 1 N N N 43.747 6.041  -0.011 -3.018 -0.859 0.393  O1B    AFH 25 
AFH O2B    O2B    O 0 1 N N N 43.814 6.076  2.399  -2.166 1.484  0.788  O2B    AFH 26 
AFH O3B    O3B    O 0 1 N N N 41.571 6.529  1.425  -3.762 0.928  -1.226 O3B    AFH 27 
AFH "C1'"  "C1'"  C 0 1 N N S 40.951 5.508  0.964  -4.898 1.098  -0.377 "C1'"  AFH 28 
AFH "C2'"  "C2'"  C 0 1 N N R 40.003 4.861  1.984  -5.761 2.247  -0.905 "C2'"  AFH 29 
AFH "C3'"  "C3'"  C 0 1 N N S 39.308 3.655  1.298  -6.958 2.444  0.032  "C3'"  AFH 30 
AFH "C4'"  "C4'"  C 0 1 N N S 38.518 4.221  0.097  -7.683 1.102  0.188  "C4'"  AFH 31 
AFH "C5'"  "C5'"  C 0 1 N N R 39.479 4.900  -0.918 -6.676 0.039  0.632  "C5'"  AFH 32 
AFH "C6'"  "C6'"  C 0 1 N N S 38.782 5.532  -2.171 -7.398 -1.296 0.822  "C6'"  AFH 33 
AFH "C7'"  "C7'"  C 0 1 N N N 39.725 6.201  -3.211 -6.376 -2.386 1.153  "C7'"  AFH 34 
AFH F      F      F 0 1 N N N 40.740 4.432  3.110  -5.002 3.421  -0.948 F      AFH 35 
AFH "O3'"  "O3'"  O 0 1 N N N 38.424 3.020  2.218  -7.852 3.410  -0.524 "O3'"  AFH 36 
AFH "O4'"  "O4'"  O 0 1 N N N 37.837 3.197  -0.605 -8.714 1.225  1.170  "O4'"  AFH 37 
AFH "O5'"  "O5'"  O 0 1 N N N 40.256 5.976  -0.239 -5.660 -0.108 -0.358 "O5'"  AFH 38 
AFH "O6'"  "O6'"  O 0 1 N N N 37.826 6.498  -1.719 -8.089 -1.639 -0.381 "O6'"  AFH 39 
AFH "O7'"  "O7'"  O 0 1 N N N 41.123 6.168  -2.921 -7.060 -3.607 1.444  "O7'"  AFH 40 
AFH H8     H8     H 0 1 N N N 48.597 10.511 3.994  4.560  1.299  1.331  H8     AFH 41 
AFH HN61   1HN6   H 0 0 N N N 52.007 10.706 7.485  10.110 3.961  1.362  HN61   AFH 42 
AFH HN62   2HN6   H 0 0 N N N 51.945 11.581 9.033  8.532  3.984  1.938  HN62   AFH 43 
AFH H2     H2     H 0 1 N N N 48.140 13.843 9.721  10.378 0.375  -1.442 H2     AFH 44 
AFH H1D    H1*    H 0 1 N N N 46.054 12.871 5.833  5.734  -0.900 -1.526 H1D    AFH 45 
AFH H2D    H2*    H 0 1 N N N 47.284 12.410 3.041  5.838  -1.753 1.372  H2D    AFH 46 
AFH "HO2'" HO2*   H 0 0 N N N 47.092 14.505 4.580  6.668  -3.636 0.315  "HO2'" AFH 47 
AFH H3D    H3*    H 0 1 N N N 45.098 12.737 2.051  3.797  -2.834 1.262  H3D    AFH 48 
AFH H4D    H4*    H 0 1 N N N 43.721 11.295 4.079  3.397  -2.142 -1.654 H4D    AFH 49 
AFH HO3A   HO3*   H 0 0 N N N 43.973 13.503 4.511  4.926  -4.552 0.252  HO3A   AFH 50 
AFH "H5'1" 1H5*   H 0 0 N N N 44.965 9.331  2.980  1.521  -2.804 -0.108 "H5'1" AFH 51 
AFH "H5'2" 2H5*   H 0 0 N N N 45.798 10.572 1.990  1.898  -1.389 0.904  "H5'2" AFH 52 
AFH HO2A   HO2A   H 0 0 N N N 42.013 9.361  3.392  -0.966 -2.708 -1.430 HO2A   AFH 53 
AFH HO2B   HO2B   H 0 0 N N N 44.739 5.953  2.223  -1.880 2.265  0.295  HO2B   AFH 54 
AFH "H1'"  "H1'"  H 0 1 N N N 41.658 4.699  0.727  -4.564 1.331  0.634  "H1'"  AFH 55 
AFH "H2'"  "H2'"  H 0 1 N N N 39.246 5.583  2.323  -6.118 2.006  -1.907 "H2'"  AFH 56 
AFH "H3'"  "H3'"  H 0 1 N N N 40.042 2.906  0.965  -6.609 2.786  1.006  "H3'"  AFH 57 
AFH "H4'"  "H4'"  H 0 1 N N N 37.799 4.944  0.509  -8.122 0.812  -0.767 "H4'"  AFH 58 
AFH "H5'"  "H5'"  H 0 1 N N N 40.121 4.085  -1.284 -6.222 0.343  1.575  "H5'"  AFH 59 
AFH "H6'"  "H6'"  H 0 1 N N N 38.321 4.690  -2.707 -8.114 -1.209 1.640  "H6'"  AFH 60 
AFH "H7'1" "1H7'" H 0 0 N N N 39.450 7.266  -3.215 -5.715 -2.535 0.299  "H7'1" AFH 61 
AFH "H7'2" "2H7'" H 0 0 N N N 39.579 5.676  -4.166 -5.789 -2.082 2.019  "H7'2" AFH 62 
AFH "HO3'" "HO3'" H 0 0 N N N 38.873 2.879  3.043  -7.355 4.236  -0.604 "HO3'" AFH 63 
AFH "HO4'" "HO4'" H 0 0 N N N 37.684 3.474  -1.501 -9.325 1.903  0.851  "HO4'" AFH 64 
AFH "HO6'" "HO6'" H 0 0 N N N 37.614 6.332  -0.808 -7.421 -1.706 -1.077 "HO6'" AFH 65 
AFH "HO7'" "HO7'" H 0 0 N N N 41.615 6.161  -3.733 -6.381 -4.265 1.646  "HO7'" AFH 66 
# 
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 
AFH N9    C8     SING Y N 1  
AFH N9    C4     SING Y N 2  
AFH N9    C1D    SING N N 3  
AFH C8    N7     DOUB Y N 4  
AFH C8    H8     SING N N 5  
AFH N7    C5     SING Y N 6  
AFH C5    C6     SING Y N 7  
AFH C5    C4     DOUB Y N 8  
AFH C6    N6     SING N N 9  
AFH C6    N1     DOUB Y N 10 
AFH N6    HN61   SING N N 11 
AFH N6    HN62   SING N N 12 
AFH N1    C2     SING Y N 13 
AFH C2    N3     DOUB Y N 14 
AFH C2    H2     SING N N 15 
AFH N3    C4     SING Y N 16 
AFH C1D   C2D    SING N N 17 
AFH C1D   O4D    SING N N 18 
AFH C1D   H1D    SING N N 19 
AFH C2D   "O2'"  SING N N 20 
AFH C2D   C3D    SING N N 21 
AFH C2D   H2D    SING N N 22 
AFH "O2'" "HO2'" SING N N 23 
AFH C3D   C4D    SING N N 24 
AFH C3D   O3D    SING N N 25 
AFH C3D   H3D    SING N N 26 
AFH C4D   O4D    SING N N 27 
AFH C4D   C5D    SING N N 28 
AFH C4D   H4D    SING N N 29 
AFH O3D   HO3A   SING N N 30 
AFH C5D   O5D    SING N N 31 
AFH C5D   "H5'1" SING N N 32 
AFH C5D   "H5'2" SING N N 33 
AFH O5D   PA     SING N N 34 
AFH PA    O1A    DOUB N N 35 
AFH PA    O2A    SING N N 36 
AFH PA    O3A    SING N N 37 
AFH O2A   HO2A   SING N N 38 
AFH O3A   PB     SING N N 39 
AFH PB    O1B    DOUB N N 40 
AFH PB    O2B    SING N N 41 
AFH PB    O3B    SING N N 42 
AFH O2B   HO2B   SING N N 43 
AFH O3B   "C1'"  SING N N 44 
AFH "C1'" "C2'"  SING N N 45 
AFH "C1'" "O5'"  SING N N 46 
AFH "C1'" "H1'"  SING N N 47 
AFH "C2'" "C3'"  SING N N 48 
AFH "C2'" F      SING N N 49 
AFH "C2'" "H2'"  SING N N 50 
AFH "C3'" "C4'"  SING N N 51 
AFH "C3'" "O3'"  SING N N 52 
AFH "C3'" "H3'"  SING N N 53 
AFH "C4'" "C5'"  SING N N 54 
AFH "C4'" "O4'"  SING N N 55 
AFH "C4'" "H4'"  SING N N 56 
AFH "C5'" "C6'"  SING N N 57 
AFH "C5'" "O5'"  SING N N 58 
AFH "C5'" "H5'"  SING N N 59 
AFH "C6'" "C7'"  SING N N 60 
AFH "C6'" "O6'"  SING N N 61 
AFH "C6'" "H6'"  SING N N 62 
AFH "C7'" "O7'"  SING N N 63 
AFH "C7'" "H7'1" SING N N 64 
AFH "C7'" "H7'2" SING N N 65 
AFH "O3'" "HO3'" SING N N 66 
AFH "O4'" "HO4'" SING N N 67 
AFH "O6'" "HO6'" SING N N 68 
AFH "O7'" "HO7'" 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 
AFH SMILES           ACDLabs              10.04 O=P(OC1OC(C(O)C(O)C1F)C(O)CO)(O)OP(=O)(O)OCC4OC(n2c3ncnc(N)c3nc2)C(O)C4O 
AFH InChI            InChI                1.02b 
;InChI=1/C17H26FN5O15P2/c18-7-10(27)11(28)13(5(25)1-24)36-17(7)37-40(32,33)38-39(30,31)34-2-6-9(26)12(29)16(35-6)23-4-22-8-14(19)20-3-21-15(8)23/h3-7,9-13,16-17,24-29H,1-2H2,(H,30,31)(H,32,33)(H2,19,20,21)/t5-,6+,7+,9+,10+,11-,12+,13+,16+,17-/m0/s1/f/h30,32H,19H2
;
AFH InChIKey         InChI                1.02b SUPCMUQXGKOKIM-ZPKQYDAMDF 
AFH SMILES_CANONICAL CACTVS               3.341 Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P@@](O)(=O)O[P@](O)(=O)O[C@@H]4O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O)[C@H]4F)[C@@H](O)[C@H]3O 
AFH SMILES           CACTVS               3.341 Nc1ncnc2n(cnc12)[CH]3O[CH](CO[P](O)(=O)O[P](O)(=O)O[CH]4O[CH]([CH](O)CO)[CH](O)[CH](O)[CH]4F)[CH](O)[CH]3O 
AFH SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO[P@](=O)(O)O[P@@](=O)(O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)[C@H](CO)O)O)O)F)O)O)N 
AFH SMILES           "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COP(=O)(O)OP(=O)(O)OC4C(C(C(C(O4)C(CO)O)O)O)F)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 
AFH "SYSTEMATIC NAME" ACDLabs              10.04 
"[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl (2S,3R,4S,5S,6R)-6-[(1S)-1,2-dihydroxyethyl]-3-fluoro-4,5-dihydroxytetrahydro-2H-pyran-2-yl dihydrogen diphosphate (non-preferred name)" 
AFH "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methyl [[(2S,3R,4S,5S,6R)-6-[(1S)-1,2-dihydroxyethyl]-3-fluoro-4,5-dihydroxy-oxan-2-yl]oxy-hydroxy-phosphoryl] hydrogen phosphate" 
# 
