data_AZT
# 
_chem_comp.id                                    AZT 
_chem_comp.name                                  "3'-AZIDO-3'-DEOXYTHYMIDINE-5'-TRIPHOSPHATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C10 H16 N5 O13 P3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_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                        507.181 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AZT 
_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        8ICO 
_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 
AZT PA     PA   P 0  1 N N S 70.958 36.167 50.856 0.366  2.497  4.196  PA     AZT 1  
AZT O1A    O1A  O 0  1 N N N 71.518 34.801 50.998 1.525  3.320  4.679  O1A    AZT 2  
AZT O2A    O2A  O 0  1 N N N 69.643 36.464 51.463 -0.728 2.151  5.336  O2A    AZT 3  
AZT O3A    O3A  O 0  1 N N N 72.043 37.234 51.329 -0.515 3.207  3.043  O3A    AZT 4  
AZT PB     PB   P 0  1 N N R 73.603 37.554 50.960 -0.120 3.728  1.566  PB     AZT 5  
AZT O1B    O1B  O 0  1 N N N 73.660 38.893 50.347 0.408  2.682  0.629  O1B    AZT 6  
AZT O2B    O2B  O 0  1 N N N 74.303 36.421 50.282 0.885  4.966  1.837  O2B    AZT 7  
AZT O3B    O3B  O 0  1 N N N 74.183 37.675 52.419 -1.491 4.439  1.094  O3B    AZT 8  
AZT PG     PG   P 0  1 N N N 74.440 36.572 53.564 -2.962 3.845  0.784  PG     AZT 9  
AZT O1G    O1G  O 0  1 N N N 73.979 35.261 53.040 -3.005 2.823  -0.314 O1G    AZT 10 
AZT O2G    O2G  O 0  1 N N N 75.860 36.712 54.016 -3.860 5.165  0.536  O2G    AZT 11 
AZT O3G    O3G  O 0  1 N N N 73.399 37.142 54.631 -3.456 3.319  2.231  O3G    AZT 12 
AZT "O5'"  O5*  O 0  1 N N N 70.886 36.513 49.313 0.767  1.059  3.573  "O5'"  AZT 13 
AZT "C5'"  C5*  C 0  1 N N N 71.138 35.468 48.413 -0.243 0.193  3.084  "C5'"  AZT 14 
AZT "C4'"  C4*  C 0  1 N N S 71.009 35.972 47.002 0.408  -1.081 2.559  "C4'"  AZT 15 
AZT "O4'"  O4*  O 0  1 N N N 69.736 35.547 46.471 -0.632 -1.924 2.028  "O4'"  AZT 16 
AZT "C3'"  C3*  C 0  1 N N S 71.071 37.500 46.889 1.383  -0.814 1.420  "C3'"  AZT 17 
AZT "N3'"  N3*  N 0  1 N N N 71.951 38.072 45.986 2.406  -1.868 1.408  "N3'"  AZT 18 
AZT "N4'"  N4*  N 1  1 N N N 72.712 38.719 45.169 3.452  -1.609 2.026  "N4'"  AZT 19 
AZT "N5'"  N5*  N -1 1 N N N ?      ?      ?      4.417  -1.381 2.590  "N5'"  AZT 20 
AZT "C2'"  C2*  C 0  1 N N N 69.631 37.898 46.534 0.515  -0.950 0.191  "C2'"  AZT 21 
AZT "C1'"  C1*  C 0  1 N N R 69.083 36.653 45.873 -0.479 -2.020 0.606  "C1'"  AZT 22 
AZT N1     N1   N 0  1 N N N 67.594 36.477 46.081 -1.757 -1.862 -0.023 N1     AZT 23 
AZT C2     C2   C 0  1 N N N 66.516 36.471 45.174 -2.074 -2.536 -1.225 C2     AZT 24 
AZT O2     O2   O 0  1 N N N 66.711 36.047 43.986 -1.296 -3.293 -1.810 O2     AZT 25 
AZT N3     N3   N 0  1 N N N 65.280 36.885 45.625 -3.356 -2.288 -1.726 N3     AZT 26 
AZT C4     C4   C 0  1 N N N 65.108 37.319 46.905 -4.324 -1.465 -1.171 C4     AZT 27 
AZT O4     O4   O 0  1 N N N 63.884 37.725 47.331 -5.435 -1.293 -1.667 O4     AZT 28 
AZT C5     C5   C 0  1 N N N 66.186 37.350 47.818 -3.920 -0.789 0.090  C5     AZT 29 
AZT C5A    C5A  C 0  1 N N N 65.857 37.678 49.262 -4.910 0.117  0.750  C5A    AZT 30 
AZT C6     C6   C 0  1 N N N 67.433 36.935 47.392 -2.694 -1.024 0.573  C6     AZT 31 
AZT HOA2   2HOA H 0  0 N N N 69.284 37.339 51.372 -0.418 1.830  6.209  HOA2   AZT 32 
AZT HOB2   2HOB H 0  0 N N N 75.209 36.607 50.067 1.305  5.413  1.071  HOB2   AZT 33 
AZT HOG2   2HOG H 0  0 N N N 76.011 36.061 54.691 -4.791 5.058  0.246  HOG2   AZT 34 
AZT HOG3   3HOG H 0  0 N N N 73.550 36.491 55.306 -4.301 2.825  2.293  HOG3   AZT 35 
AZT "H5'1" 1H5* H 0  0 N N N 72.125 34.984 48.597 -0.935 -0.037 3.899  "H5'1" AZT 36 
AZT "H5'2" 2H5* H 0  0 N N N 70.487 34.583 48.604 -0.788 0.703  2.284  "H5'2" AZT 37 
AZT "H4'"  H4*  H 0  1 N N N 71.872 35.552 46.434 0.878  -1.606 3.397  "H4'"  AZT 38 
AZT "H3'"  H3*  H 0  1 N N N 71.478 37.885 47.852 1.883  0.156  1.490  "H3'"  AZT 39 
AZT "H2'1" 1H2* H 0  0 N N N 69.027 38.271 47.393 -0.002 -0.000 0.004  "H2'1" AZT 40 
AZT "H2'2" 2H2* H 0  0 N N N 69.543 38.825 45.921 1.058  -1.218 -0.720 "H2'2" AZT 41 
AZT "H1'"  H1*  H 0  1 N N N 69.259 36.734 44.775 -0.111 -3.025 0.371  "H1'"  AZT 42 
AZT HN3    HN3  H 0  1 N N N 64.475 36.869 44.998 -3.604 -2.764 -2.590 HN3    AZT 43 
AZT H51    1H5  H 0  1 N N N 66.707 37.702 49.982 -5.490 0.642  -0.007 H51    AZT 44 
AZT H52    2H5  H 0  1 N N N 65.304 38.645 49.306 -4.387 0.843  1.372  H52    AZT 45 
AZT H53    3H5  H 0  1 N N N 65.075 36.975 49.633 -5.581 -0.467 1.379  H53    AZT 46 
AZT H6     H6   H 0  1 N N N 68.287 36.968 48.088 -2.359 -0.551 1.492  H6     AZT 47 
# 
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 
AZT PA    O1A    DOUB N N 1  
AZT PA    O2A    SING N N 2  
AZT PA    O3A    SING N N 3  
AZT PA    "O5'"  SING N N 4  
AZT O2A   HOA2   SING N N 5  
AZT O3A   PB     SING N N 6  
AZT PB    O1B    DOUB N N 7  
AZT PB    O2B    SING N N 8  
AZT PB    O3B    SING N N 9  
AZT O2B   HOB2   SING N N 10 
AZT O3B   PG     SING N N 11 
AZT PG    O1G    DOUB N N 12 
AZT PG    O2G    SING N N 13 
AZT PG    O3G    SING N N 14 
AZT O2G   HOG2   SING N N 15 
AZT O3G   HOG3   SING N N 16 
AZT "O5'" "C5'"  SING N N 17 
AZT "C5'" "C4'"  SING N N 18 
AZT "C5'" "H5'1" SING N N 19 
AZT "C5'" "H5'2" SING N N 20 
AZT "C4'" "O4'"  SING N N 21 
AZT "C4'" "C3'"  SING N N 22 
AZT "C4'" "H4'"  SING N N 23 
AZT "O4'" "C1'"  SING N N 24 
AZT "C3'" "N3'"  SING N N 25 
AZT "C3'" "C2'"  SING N N 26 
AZT "C3'" "H3'"  SING N N 27 
AZT "N3'" "N4'"  DOUB N N 28 
AZT "N4'" "N5'"  DOUB N N 29 
AZT "C2'" "C1'"  SING N N 30 
AZT "C2'" "H2'1" SING N N 31 
AZT "C2'" "H2'2" SING N N 32 
AZT "C1'" N1     SING N N 33 
AZT "C1'" "H1'"  SING N N 34 
AZT N1    C2     SING N N 35 
AZT N1    C6     SING N N 36 
AZT C2    O2     DOUB N N 37 
AZT C2    N3     SING N N 38 
AZT N3    C4     SING N N 39 
AZT N3    HN3    SING N N 40 
AZT C4    O4     DOUB N N 41 
AZT C4    C5     SING N N 42 
AZT C5    C5A    SING N N 43 
AZT C5    C6     DOUB N N 44 
AZT C5A   H51    SING N N 45 
AZT C5A   H52    SING N N 46 
AZT C5A   H53    SING N N 47 
AZT C6    H6     SING N N 48 
# 
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 
AZT SMILES           ACDLabs              10.04 O=P(O)(O)OP(=O)(O)OP(=O)(O)OCC2OC(N1C(=O)NC(=O)C(=C1)C)CC2\N=[N+]=[N-] 
AZT InChI            InChI                1.02b 
InChI=1/C10H16N5O13P3/c1-5-3-15(10(17)12-9(5)16)8-2-6(13-14-11)7(26-8)4-25-30(21,22)28-31(23,24)27-29(18,19)20/h3,6-8H,2,4H2,1H3,(H,21,22)(H,23,24)(H,12,16,17)(H2,18,19,20)/t6-,7+,8+/m0/s1/f/h12,18-19,21,23H 
AZT InChIKey         InChI                1.02b GLWHPRRGGYLLRV-PYUVYISODT 
AZT SMILES_CANONICAL CACTVS               3.341 CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](CO[P@@](O)(=O)O[P@@](O)(=O)O[P](O)(O)=O)O2)C(=O)NC1=O 
AZT SMILES           CACTVS               3.341 CC1=CN([CH]2C[CH](N=[N+]=[N-])[CH](CO[P](O)(=O)O[P](O)(=O)O[P](O)(O)=O)O2)C(=O)NC1=O 
AZT SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO[P@](=O)(O)O[P@](=O)(O)OP(=O)(O)O)N=[N+]=[N-] 
AZT SMILES           "OpenEye OEToolkits" 1.5.0 CC1=CN(C(=O)NC1=O)C2CC(C(O2)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)N=[N+]=[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 
AZT "SYSTEMATIC NAME" ACDLabs              10.04 
;3'-azido-3'-deoxythymidine 5'-(tetrahydrogen triphosphate)
;
AZT "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)oxolan-2-yl]methyl (hydroxy-phosphonooxy-phosphoryl) hydrogen phosphate" 
# 
