data_594 # _chem_comp.id 594 _chem_comp.name "9-[2-deoxy-2-fluoro-5-O-({5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoyl}sulfamoyl)-beta-D-arabinofuranosyl]-9H-purin-6-amine" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C20 H27 F N8 O7 S2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2015-02-04 _chem_comp.pdbx_modified_date 2015-08-28 _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 574.606 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 594 _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 4XTZ _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 594 CBI C1 C 0 1 N N S -2.212 -10.030 13.817 6.250 1.841 -0.311 CBI 594 1 594 NAU N1 N 0 1 N N N -0.993 -9.298 13.528 6.208 1.585 1.137 NAU 594 2 594 CBA C2 C 0 1 N N N -0.061 -9.509 14.454 7.459 1.433 1.591 CBA 594 3 594 OAC O1 O 0 1 N N N 1.030 -8.958 14.497 7.719 1.210 2.758 OAC 594 4 594 NAT N2 N 0 1 N N N -0.486 -10.392 15.346 8.398 1.550 0.642 NAT 594 5 594 CBF C3 C 0 1 N N R -1.888 -10.690 15.159 7.746 1.817 -0.649 CBF 594 6 594 CAO C4 C 0 1 N N N -2.646 -10.048 16.310 8.105 0.694 -1.641 CAO 594 7 594 SAY S1 S 0 1 N N N -3.436 -8.637 15.629 6.757 -0.529 -1.375 SAY 594 8 594 CBH C5 C 0 1 N N S -3.411 -9.095 13.932 5.464 0.737 -1.045 CBH 594 9 594 CAK C6 C 0 1 N N N -3.301 -7.896 12.999 4.364 0.167 -0.148 CAK 594 10 594 CAI C7 C 0 1 N N N -3.585 -8.352 11.572 3.525 -0.835 -0.945 CAI 594 11 594 CAH C8 C 0 1 N N N -3.901 -7.186 10.643 2.424 -1.405 -0.048 CAH 594 12 594 CAJ C9 C 0 1 N N N -4.189 -7.680 9.228 1.585 -2.407 -0.844 CAJ 594 13 594 CAZ C10 C 0 1 N N N -4.593 -6.512 8.360 0.501 -2.968 0.039 CAZ 594 14 594 OAB O2 O 0 1 N N N -5.695 -6.001 8.482 0.408 -2.603 1.192 OAB 594 15 594 NAV N3 N 0 1 N N N -3.687 -6.075 7.490 -0.365 -3.876 -0.452 NAV 594 16 594 SBK S2 S 0 1 N N N -4.083 -4.968 6.403 -1.557 -4.493 0.519 SBK 594 17 594 OAD O3 O 0 1 N N N -5.266 -5.380 5.700 -2.312 -5.384 -0.290 OAD 594 18 594 OAE O4 O 0 1 N N N -3.005 -4.791 5.471 -0.924 -4.889 1.729 OAE 594 19 594 OAW O5 O 0 1 N N N -4.360 -3.652 7.145 -2.487 -3.343 0.877 OAW 594 20 594 CAN C11 C 0 1 N N N -3.296 -2.876 7.695 -3.352 -2.943 -0.188 CAN 594 21 594 CBE C12 C 0 1 N N R -3.729 -1.416 7.738 -4.238 -1.787 0.282 CBE 594 22 594 OAX O6 O 0 1 N N N -4.872 -1.211 8.582 -3.449 -0.590 0.462 OAX 594 23 594 CAL C13 C 0 1 N N R -2.654 -0.478 8.260 -5.267 -1.420 -0.810 CAL 594 24 594 OAL O7 O 0 1 N N N -1.784 -0.073 7.202 -6.531 -2.024 -0.530 OAL 594 25 594 CAM C14 C 0 1 N N S -3.475 0.685 8.780 -5.372 0.119 -0.725 CAM 594 26 594 F8Q F1 F 0 1 N N N -2.814 1.435 9.718 -4.976 0.705 -1.933 F8Q 594 27 594 CBG C15 C 0 1 N N R -4.759 0.033 9.290 -4.394 0.500 0.408 CBG 594 28 594 N9 N4 N 0 1 Y N N -4.787 -0.234 10.756 -3.707 1.755 0.089 N9 594 29 594 C8 C16 C 0 1 Y N N -3.752 -0.334 11.608 -2.516 1.879 -0.562 C8 594 30 594 N7 N5 N 0 1 Y N N -4.216 -0.596 12.851 -2.201 3.137 -0.676 N7 594 31 594 C5 C17 C 0 1 Y N N -5.561 -0.669 12.767 -3.168 3.897 -0.108 C5 594 32 594 C4 C18 C 0 1 Y N N -5.908 -0.446 11.448 -4.149 3.020 0.384 C4 594 33 594 N3 N6 N 0 1 Y N N -7.212 -0.464 11.084 -5.220 3.522 0.990 N3 594 34 594 C2 C19 C 0 1 Y N N -8.160 -0.704 11.997 -5.364 4.824 1.126 C2 594 35 594 N1 N7 N 0 1 Y N N -7.852 -0.922 13.282 -4.472 5.687 0.677 N1 594 36 594 C6 C20 C 0 1 Y N N -6.565 -0.913 13.694 -3.365 5.277 0.065 C6 594 37 594 N6 N8 N 0 1 N N N -6.262 -1.138 14.995 -2.436 6.190 -0.403 N6 594 38 594 H1 H1 H 0 1 N N N -2.404 -10.800 13.055 5.827 2.820 -0.539 H1 594 39 594 H2 H2 H 0 1 N N N -0.869 -8.707 12.731 5.403 1.534 1.676 H2 594 40 594 H3 H3 H 0 1 N N N 0.088 -10.799 16.056 9.355 1.471 0.784 H3 594 41 594 H4 H4 H 0 1 N N N -2.079 -11.773 15.118 8.061 2.786 -1.038 H4 594 42 594 H5 H5 H 0 1 N N N -3.392 -10.747 16.715 8.093 1.065 -2.666 H5 594 43 594 H6 H6 H 0 1 N N N -1.951 -9.750 17.109 9.076 0.262 -1.401 H6 594 44 594 H7 H7 H 0 1 N N N -4.340 -9.647 13.729 5.047 1.115 -1.978 H7 594 45 594 H8 H8 H 0 1 N N N -2.286 -7.475 13.057 4.815 -0.336 0.706 H8 594 46 594 H9 H9 H 0 1 N N N -4.033 -7.130 13.294 3.725 0.978 0.203 H9 594 47 594 H10 H10 H 0 1 N N N -4.445 -9.037 11.584 3.073 -0.332 -1.799 H10 594 48 594 H11 H11 H 0 1 N N N -2.701 -8.881 11.187 4.163 -1.645 -1.296 H11 594 49 594 H12 H12 H 0 1 N N N -3.040 -6.502 10.617 2.876 -1.908 0.807 H12 594 50 594 H13 H13 H 0 1 N N N -4.783 -6.651 11.024 1.786 -0.594 0.303 H13 594 51 594 H14 H14 H 0 1 N N N -5.006 -8.416 9.256 1.133 -1.904 -1.699 H14 594 52 594 H15 H15 H 0 1 N N N -3.285 -8.150 8.813 2.224 -3.217 -1.195 H15 594 53 594 H16 H16 H 0 1 N N N -2.756 -6.439 7.515 -0.291 -4.168 -1.374 H16 594 54 594 H17 H17 H 0 1 N N N -3.071 -3.226 8.713 -2.754 -2.620 -1.040 H17 594 55 594 H18 H18 H 0 1 N N N -2.400 -2.978 7.066 -3.980 -3.784 -0.482 H18 594 56 594 H19 H19 H 0 1 N N N -3.980 -1.107 6.712 -4.746 -2.051 1.209 H19 594 57 594 H20 H20 H 0 1 N N N -2.099 -0.953 9.083 -4.906 -1.724 -1.793 H20 594 58 594 H21 H21 H 0 1 N N N -1.119 0.512 7.545 -7.215 -1.827 -1.185 H21 594 59 594 H22 H22 H 0 1 N N N -3.742 1.318 7.921 -6.388 0.419 -0.470 H22 594 60 594 H23 H23 H 0 1 N N N -5.606 0.685 9.030 -4.926 0.588 1.355 H23 594 61 594 H24 H24 H 0 1 N N N -2.711 -0.222 11.341 -1.921 1.056 -0.927 H24 594 62 594 H25 H25 H 0 1 N N N -9.196 -0.722 11.691 -6.247 5.199 1.623 H25 594 63 594 H26 H26 H 0 1 N N N -7.104 -1.292 15.512 -1.637 5.879 -0.858 H26 594 64 594 H27 H27 H 0 1 N N N -5.675 -1.945 15.066 -2.583 7.140 -0.277 H27 594 65 # 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 594 OAE SBK DOUB N N 1 594 OAD SBK DOUB N N 2 594 SBK OAW SING N N 3 594 SBK NAV SING N N 4 594 OAW CAN SING N N 5 594 OAL CAL SING N N 6 594 NAV CAZ SING N N 7 594 CAN CBE SING N N 8 594 CBE CAL SING N N 9 594 CBE OAX SING N N 10 594 CAL CAM SING N N 11 594 CAZ OAB DOUB N N 12 594 CAZ CAJ SING N N 13 594 OAX CBG SING N N 14 594 CAM CBG SING N N 15 594 CAM F8Q SING N N 16 594 CAJ CAH SING N N 17 594 CBG N9 SING N N 18 594 CAH CAI SING N N 19 594 N9 C4 SING Y N 20 594 N9 C8 SING Y N 21 594 N3 C4 DOUB Y N 22 594 N3 C2 SING Y N 23 594 C4 C5 SING Y N 24 594 CAI CAK SING N N 25 594 C8 N7 DOUB Y N 26 594 C2 N1 DOUB Y N 27 594 C5 N7 SING Y N 28 594 C5 C6 DOUB Y N 29 594 CAK CBH SING N N 30 594 N1 C6 SING Y N 31 594 NAU CBI SING N N 32 594 NAU CBA SING N N 33 594 C6 N6 SING N N 34 594 CBI CBH SING N N 35 594 CBI CBF SING N N 36 594 CBH SAY SING N N 37 594 CBA OAC DOUB N N 38 594 CBA NAT SING N N 39 594 CBF NAT SING N N 40 594 CBF CAO SING N N 41 594 SAY CAO SING N N 42 594 CBI H1 SING N N 43 594 NAU H2 SING N N 44 594 NAT H3 SING N N 45 594 CBF H4 SING N N 46 594 CAO H5 SING N N 47 594 CAO H6 SING N N 48 594 CBH H7 SING N N 49 594 CAK H8 SING N N 50 594 CAK H9 SING N N 51 594 CAI H10 SING N N 52 594 CAI H11 SING N N 53 594 CAH H12 SING N N 54 594 CAH H13 SING N N 55 594 CAJ H14 SING N N 56 594 CAJ H15 SING N N 57 594 NAV H16 SING N N 58 594 CAN H17 SING N N 59 594 CAN H18 SING N N 60 594 CBE H19 SING N N 61 594 CAL H20 SING N N 62 594 OAL H21 SING N N 63 594 CAM H22 SING N N 64 594 CBG H23 SING N N 65 594 C8 H24 SING N N 66 594 C2 H25 SING N N 67 594 N6 H26 SING N N 68 594 N6 H27 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 594 SMILES ACDLabs 12.01 "O=C1NC2C(SCC2N1)CCCCC(=O)NS(=O)(=O)OCC5OC(n3c4ncnc(N)c4nc3)C(F)C5O" 594 InChI InChI 1.03 "InChI=1S/C20H27FN8O7S2/c21-13-16(31)10(36-19(13)29-8-25-15-17(22)23-7-24-18(15)29)5-35-38(33,34)28-12(30)4-2-1-3-11-14-9(6-37-11)26-20(32)27-14/h7-11,13-14,16,19,31H,1-6H2,(H,28,30)(H2,22,23,24)(H2,26,27,32)/t9-,10+,11-,13-,14-,16+,19+/m0/s1" 594 InChIKey InChI 1.03 XTTQQKAKULCXCM-ROPJLRCXSA-N 594 SMILES_CANONICAL CACTVS 3.385 "Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[S](=O)(=O)NC(=O)CCCC[C@@H]4SC[C@@H]5NC(=O)N[C@H]45)[C@@H](O)[C@@H]3F" 594 SMILES CACTVS 3.385 "Nc1ncnc2n(cnc12)[CH]3O[CH](CO[S](=O)(=O)NC(=O)CCCC[CH]4SC[CH]5NC(=O)N[CH]45)[CH](O)[CH]3F" 594 SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "c1nc(c2c(n1)n(cn2)[C@H]3[C@H]([C@@H]([C@H](O3)COS(=O)(=O)NC(=O)CCCC[C@H]4[C@@H]5[C@H](CS4)NC(=O)N5)O)F)N" 594 SMILES "OpenEye OEToolkits" 1.9.2 "c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COS(=O)(=O)NC(=O)CCCCC4C5C(CS4)NC(=O)N5)O)F)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 594 "SYSTEMATIC NAME" ACDLabs 12.01 "9-[2-deoxy-2-fluoro-5-O-({5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoyl}sulfamoyl)-beta-D-arabinofuranosyl]-9H-purin-6-amine" 594 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "[(2R,3R,4S,5R)-5-(6-aminopurin-9-yl)-4-fluoranyl-3-oxidanyl-oxolan-2-yl]methyl N-[5-[(3aS,4S,6aR)-2-oxidanylidene-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoyl]sulfamate" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 594 "Create component" 2015-02-04 RCSB 594 "Initial release" 2015-09-02 RCSB #