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 2011-06-04 _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 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-]" AZT InChI InChI 1.03 "InChI=1S/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" AZT InChIKey InChI 1.03 GLWHPRRGGYLLRV-XLPZGREQSA-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" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site AZT "Create component" 1999-07-08 EBI AZT "Modify descriptor" 2011-06-04 RCSB #