data_TFO
# 
_chem_comp.id                                    TFO 
_chem_comp.name                                  "[2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY]METHYLPHOSPHONIC ACID" 
_chem_comp.type                                  "DNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C9 H14 N5 O4 P" 
_chem_comp.mon_nstd_parent_comp_id               DA 
_chem_comp.pdbx_synonyms                         TENOFOVIR 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-04-21 
_chem_comp.pdbx_modified_date                    2009-01-07 
_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                        287.212 
_chem_comp.one_letter_code                       A 
_chem_comp.three_letter_code                     TFO 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   Y 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1T03 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
TFO P      P      P 0 1 N N N 30.290 141.781 -17.752 0.384  -2.532 3.272  P      TFO 1  
TFO OP2    O2P    O 0 1 N N N 31.450 141.506 -16.961 -0.482 -3.623 2.452  OP2    TFO 2  
TFO OP1    O1P    O 0 1 N N N 29.444 140.759 -18.471 1.779  -2.957 3.624  OP1    TFO 3  
TFO "C9'"  "C9'"  C 0 1 N N N 31.065 142.510 -18.997 0.280  -1.069 2.264  "C9'"  TFO 4  
TFO "O9'"  "O9'"  O 0 1 N N N 32.571 142.308 -18.915 1.010  -1.385 1.086  "O9'"  TFO 5  
TFO "C8'"  "C8'"  C 0 1 N N N 32.232 140.608 -20.832 1.840  -0.731 -1.038 "C8'"  TFO 6  
TFO "C7'"  "C7'"  C 0 1 N N R 33.021 141.996 -20.163 1.039  -0.291 0.180  "C7'"  TFO 7  
TFO "C6'"  "C6'"  C 0 1 N N N 34.499 141.773 -20.048 1.688  0.924  0.849  "C6'"  TFO 8  
TFO N9     N9     N 0 1 Y N N 35.634 141.815 -19.243 1.769  2.082  -0.040 N9     TFO 9  
TFO C4     C4     C 0 1 Y N N 36.761 141.501 -19.853 0.832  3.050  -0.179 C4     TFO 10 
TFO N3     N3     N 0 1 Y N N 36.703 141.138 -21.099 -0.349 3.159  0.448  N3     TFO 11 
TFO C2     C2     C 0 1 Y N N 37.868 140.927 -21.581 -1.002 4.268  0.035  C2     TFO 12 
TFO N1     N1     N 0 1 Y N N 39.021 141.087 -20.922 -0.611 5.196  -0.871 N1     TFO 13 
TFO C6     C6     C 0 1 Y N N 39.041 141.516 -19.637 0.593  5.021  -1.466 C6     TFO 14 
TFO N6     N6     N 0 1 N N N 40.271 141.746 -19.092 1.054  5.950  -2.415 N6     TFO 15 
TFO C5     C5     C 0 1 Y N N 37.781 141.720 -19.015 1.363  3.913  -1.124 C5     TFO 16 
TFO N7     N7     N 0 1 Y N N 37.323 142.143 -17.766 2.593  3.476  -1.545 N7     TFO 17 
TFO C8     C8     C 0 1 Y N N 35.973 142.161 -17.907 2.807  2.367  -0.868 C8     TFO 18 
TFO OP3    O3P    O 0 1 N Y N ?      ?       ?       -0.562 -2.179 4.534  OP3    TFO 19 
TFO HOP2   2HOP   H 0 0 N N N 31.982 142.149 -16.508 -0.548 -4.537 2.802  HOP2   TFO 20 
TFO "H9'1" "1H9'" H 0 0 N N N 30.662 142.173 -19.980 0.737  -0.217 2.777  "H9'1" TFO 21 
TFO "H9'2" "2H9'" H 0 0 N N N 30.802 143.591 -19.062 -0.761 -0.836 2.017  "H9'2" TFO 22 
TFO "H8'1" "1H8'" H 0 0 N N N 32.600 140.352 -21.853 1.430  -1.648 -1.473 "H8'1" TFO 23 
TFO "H8'2" "2H8'" H 0 0 N N N 32.315 139.732 -20.146 1.832  0.052  -1.803 "H8'2" TFO 24 
TFO "H8'3" "3H8'" H 0 0 N N N 31.124 140.737 -20.827 2.890  -0.904 -0.776 "H8'3" TFO 25 
TFO "H7'"  "H7'"  H 0 1 N N N 32.789 142.831 -20.864 0.009  -0.078 -0.126 "H7'"  TFO 26 
TFO "H6'1" "1H6'" H 0 0 N N N 34.553 140.712 -20.388 1.115  1.245  1.728  "H6'1" TFO 27 
TFO "H6'2" "2H6'" H 0 0 N N N 34.848 142.410 -20.893 2.707  0.694  1.183  "H6'2" TFO 28 
TFO H2     H2     H 0 1 N N N 37.879 140.586 -22.629 -1.970 4.439  0.493  H2     TFO 29 
TFO HN61   1HN6   H 0 0 N N N 40.286 142.069 -18.124 1.133  5.675  -3.376 HN61   TFO 30 
TFO HN62   2HN6   H 0 0 N N N 40.790 142.397 -19.679 1.388  6.843  -2.108 HN62   TFO 31 
TFO H8     H8     H 0 1 N N N 35.279 142.410 -17.086 3.687  1.743  -0.944 H8     TFO 32 
TFO HOP3   3HOP   H 0 0 N N N -0.770 0.182   -0.525  -0.644 -2.829 5.264  HOP3   TFO 33 
# 
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 
TFO P     OP2    SING N N 1  
TFO P     OP1    DOUB N N 2  
TFO P     "C9'"  SING N N 3  
TFO P     OP3    SING N N 4  
TFO OP2   HOP2   SING N N 5  
TFO "C9'" "O9'"  SING N N 6  
TFO "C9'" "H9'1" SING N N 7  
TFO "C9'" "H9'2" SING N N 8  
TFO "O9'" "C7'"  SING N N 9  
TFO "C8'" "C7'"  SING N N 10 
TFO "C8'" "H8'1" SING N N 11 
TFO "C8'" "H8'2" SING N N 12 
TFO "C8'" "H8'3" SING N N 13 
TFO "C7'" "C6'"  SING N N 14 
TFO "C7'" "H7'"  SING N N 15 
TFO "C6'" N9     SING N N 16 
TFO "C6'" "H6'1" SING N N 17 
TFO "C6'" "H6'2" SING N N 18 
TFO N9    C4     SING Y N 19 
TFO N9    C8     SING Y N 20 
TFO C4    N3     SING Y N 21 
TFO C4    C5     DOUB Y N 22 
TFO N3    C2     DOUB Y N 23 
TFO C2    N1     SING Y N 24 
TFO C2    H2     SING N N 25 
TFO N1    C6     DOUB Y N 26 
TFO C6    N6     SING N N 27 
TFO C6    C5     SING Y N 28 
TFO N6    HN61   SING N N 29 
TFO N6    HN62   SING N N 30 
TFO C5    N7     SING Y N 31 
TFO N7    C8     DOUB Y N 32 
TFO C8    H8     SING N N 33 
TFO OP3   HOP3   SING N N 34 
# 
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 
TFO SMILES           ACDLabs              10.04 "O=P(O)(O)COC(C)Cn1c2ncnc(c2nc1)N"                                                                                                               
TFO InChI            InChI                1.02b "InChI=1/C9H14N5O4P/c1-6(18-5-19(15,16)17)2-14-4-13-7-8(10)11-3-12-9(7)14/h3-4,6H,2,5H2,1H3,(H2,10,11,12)(H2,15,16,17)/t6-/m1/s1/f/h15-16H,10H2" 
TFO InChIKey         InChI                1.02b SGOIRFVFHAKUTI-DIXDEQOFDQ                                                                                                                        
TFO SMILES_CANONICAL CACTVS               3.341 "C[C@H](Cn1cnc2c(N)ncnc12)OC[P](O)(O)=O"                                                                                                         
TFO SMILES           CACTVS               3.341 "C[CH](Cn1cnc2c(N)ncnc12)OC[P](O)(O)=O"                                                                                                          
TFO SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C[C@H](Cn1cnc2c1ncnc2N)OCP(=O)(O)O"                                                                                                             
TFO SMILES           "OpenEye OEToolkits" 1.5.0 "CC(Cn1cnc2c1ncnc2N)OCP(=O)(O)O"                                                                                                                 
# 
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 
TFO "SYSTEMATIC NAME" ACDLabs              10.04 "{[(1R)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy]methyl}phosphonic acid" 
TFO "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethylphosphonic acid"        
# 
