data_4S1 # _chem_comp.id 4S1 _chem_comp.name "(1R,2S,3R,5R)-3-{[5-(1,3-benzothiazol-2-yl)-2-(propylamino)pyrimidin-4-yl]amino}-5-(hydroxymethyl)cyclopentane-1,2-diol" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C20 H25 N5 O3 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2015-05-17 _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 415.509 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 4S1 _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 4ZTL _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 4S1 C01 C1 C 0 1 Y N N 29.984 8.305 -8.357 -0.664 0.399 0.189 C01 4S1 1 4S1 N02 N1 N 0 1 Y N N 29.393 7.658 -7.289 -1.987 0.313 0.241 N02 4S1 2 4S1 C03 C2 C 0 1 Y N N 29.640 6.358 -7.087 -2.740 1.403 0.188 C03 4S1 3 4S1 N04 N2 N 0 1 Y N N 30.441 5.594 -7.870 -2.214 2.616 0.083 N04 4S1 4 4S1 C05 C3 C 0 1 Y N N 31.048 6.197 -8.951 -0.904 2.789 0.025 C05 4S1 5 4S1 C06 C4 C 0 1 Y N N 30.816 7.582 -9.296 -0.068 1.672 0.076 C06 4S1 6 4S1 N07 N3 N 0 1 N N N 29.670 9.647 -8.493 0.117 -0.739 0.249 N07 4S1 7 4S1 N08 N4 N 0 1 N N N 29.009 5.760 -5.989 -4.114 1.272 0.245 N08 4S1 8 4S1 C09 C5 C 0 1 Y N N 31.534 8.251 -10.403 1.399 1.820 0.015 C09 4S1 9 4S1 C10 C6 C 0 1 N N R 28.873 10.506 -7.591 -0.515 -2.055 0.371 C10 4S1 10 4S1 C11 C7 C 0 1 N N S 29.658 10.905 -6.305 -0.882 -2.620 -1.024 C11 4S1 11 4S1 C12 C8 C 0 1 N N R 30.414 12.220 -6.718 -0.939 -4.147 -0.811 C12 4S1 12 4S1 C13 C9 C 0 1 N N R 29.589 12.882 -7.868 -0.065 -4.452 0.418 C13 4S1 13 4S1 C14 C10 C 0 1 N N N 28.469 11.858 -8.221 0.494 -3.101 0.909 C14 4S1 14 4S1 O15 O1 O 0 1 N N N 28.759 11.132 -5.195 -2.155 -2.125 -1.444 O15 4S1 15 4S1 O16 O2 O 0 1 N N N 30.728 13.122 -5.673 -2.287 -4.556 -0.567 O16 4S1 16 4S1 C17 C11 C 0 1 N N N 30.483 13.197 -9.119 1.084 -5.384 0.025 C17 4S1 17 4S1 O18 O3 O 0 1 N N N 29.731 13.911 -10.095 1.819 -5.753 1.193 O18 4S1 18 4S1 C19 C12 C 0 1 N N N 28.130 6.427 -4.990 -4.966 2.462 0.190 C19 4S1 19 4S1 C20 C13 C 0 1 N N N 27.447 5.441 -4.028 -6.435 2.041 0.271 C20 4S1 20 4S1 C21 C14 C 0 1 N N N 26.446 6.149 -3.108 -7.326 3.284 0.212 C21 4S1 21 4S1 S22 S1 S 0 1 Y N N 32.804 7.390 -11.279 2.249 3.353 -0.126 S22 4S1 22 4S1 C23 C15 C 0 1 Y N N 33.178 8.851 -12.145 3.796 2.511 -0.118 C23 4S1 23 4S1 C24 C16 C 0 1 Y N N 32.340 9.915 -11.718 3.552 1.137 -0.010 C24 4S1 24 4S1 N25 N5 N 0 1 Y N N 31.452 9.565 -10.711 2.241 0.842 0.062 N25 4S1 25 4S1 C26 C17 C 0 1 Y N N 34.150 9.043 -13.135 5.102 2.989 -0.203 C26 4S1 26 4S1 C27 C18 C 0 1 Y N N 34.310 10.316 -13.764 6.164 2.113 -0.182 C27 4S1 27 4S1 C28 C19 C 0 1 Y N N 33.465 11.407 -13.382 5.935 0.749 -0.075 C28 4S1 28 4S1 C29 C20 C 0 1 Y N N 32.498 11.207 -12.343 4.657 0.259 0.016 C29 4S1 29 4S1 H1 H1 H 0 1 N N N 31.721 5.614 -9.562 -0.487 3.782 -0.062 H1 4S1 30 4S1 H2 H2 H 0 1 N N N 30.556 10.106 -8.557 1.084 -0.667 0.210 H2 4S1 31 4S1 H3 H3 H 0 1 N N N 28.448 5.030 -6.380 -4.514 0.391 0.322 H3 4S1 32 4S1 H4 H4 H 0 1 N N N 27.959 9.973 -7.289 -1.396 -2.001 1.010 H4 4S1 33 4S1 H5 H5 H 0 1 N N N 30.393 10.122 -6.066 -0.114 -2.363 -1.753 H5 4S1 34 4S1 H6 H6 H 0 1 N N N 31.360 11.893 -7.173 -0.546 -4.661 -1.687 H6 4S1 35 4S1 H7 H7 H 0 1 N N N 29.133 13.814 -7.502 -0.668 -4.913 1.200 H7 4S1 36 4S1 H8 H8 H 0 1 N N N 27.507 12.194 -7.808 1.485 -2.924 0.491 H8 4S1 37 4S1 H9 H9 H 0 1 N N N 28.383 11.755 -9.313 0.527 -3.074 1.998 H9 4S1 38 4S1 H10 H10 H 0 1 N N N 29.260 11.373 -4.425 -2.435 -2.447 -2.312 H10 4S1 39 4S1 H11 H11 H 0 1 N N N 31.228 12.670 -5.003 -2.893 -4.371 -1.297 H11 4S1 40 4S1 H12 H12 H 0 1 N N N 30.842 12.253 -9.556 0.680 -6.279 -0.448 H12 4S1 41 4S1 H13 H13 H 0 1 N N N 31.343 13.807 -8.806 1.745 -4.871 -0.673 H13 4S1 42 4S1 H14 H14 H 0 1 N N N 30.282 14.096 -10.847 2.564 -6.344 1.019 H14 4S1 43 4S1 H15 H15 H 0 1 N N N 28.740 7.126 -4.399 -4.730 3.118 1.027 H15 4S1 44 4S1 H16 H16 H 0 1 N N N 27.351 6.986 -5.529 -4.791 2.991 -0.747 H16 4S1 45 4S1 H17 H17 H 0 1 N N N 26.914 4.680 -4.617 -6.672 1.385 -0.567 H17 4S1 46 4S1 H18 H18 H 0 1 N N N 28.216 4.954 -3.411 -6.611 1.512 1.207 H18 4S1 47 4S1 H19 H19 H 0 1 N N N 25.980 5.413 -2.437 -8.372 2.984 0.270 H19 4S1 48 4S1 H20 H20 H 0 1 N N N 26.971 6.909 -2.510 -7.089 3.940 1.050 H20 4S1 49 4S1 H21 H21 H 0 1 N N N 25.669 6.634 -3.717 -7.150 3.813 -0.725 H21 4S1 50 4S1 H22 H22 H 0 1 N N N 34.786 8.220 -13.426 5.281 4.051 -0.286 H22 4S1 51 4S1 H23 H23 H 0 1 N N N 35.065 10.455 -14.524 7.174 2.487 -0.253 H23 4S1 52 4S1 H24 H24 H 0 1 N N N 33.555 12.366 -13.870 6.772 0.066 -0.059 H24 4S1 53 4S1 H25 H25 H 0 1 N N N 31.880 12.033 -12.024 4.495 -0.805 0.098 H25 4S1 54 # 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 4S1 C27 C28 DOUB Y N 1 4S1 C27 C26 SING Y N 2 4S1 C28 C29 SING Y N 3 4S1 C26 C23 DOUB Y N 4 4S1 C29 C24 DOUB Y N 5 4S1 C23 C24 SING Y N 6 4S1 C23 S22 SING Y N 7 4S1 C24 N25 SING Y N 8 4S1 S22 C09 SING Y N 9 4S1 N25 C09 DOUB Y N 10 4S1 C09 C06 SING N N 11 4S1 O18 C17 SING N N 12 4S1 C06 C05 DOUB Y N 13 4S1 C06 C01 SING Y N 14 4S1 C17 C13 SING N N 15 4S1 C05 N04 SING Y N 16 4S1 N07 C01 SING N N 17 4S1 N07 C10 SING N N 18 4S1 C01 N02 DOUB Y N 19 4S1 C14 C13 SING N N 20 4S1 C14 C10 SING N N 21 4S1 N04 C03 DOUB Y N 22 4S1 C13 C12 SING N N 23 4S1 C10 C11 SING N N 24 4S1 N02 C03 SING Y N 25 4S1 C03 N08 SING N N 26 4S1 C12 C11 SING N N 27 4S1 C12 O16 SING N N 28 4S1 C11 O15 SING N N 29 4S1 N08 C19 SING N N 30 4S1 C19 C20 SING N N 31 4S1 C20 C21 SING N N 32 4S1 C05 H1 SING N N 33 4S1 N07 H2 SING N N 34 4S1 N08 H3 SING N N 35 4S1 C10 H4 SING N N 36 4S1 C11 H5 SING N N 37 4S1 C12 H6 SING N N 38 4S1 C13 H7 SING N N 39 4S1 C14 H8 SING N N 40 4S1 C14 H9 SING N N 41 4S1 O15 H10 SING N N 42 4S1 O16 H11 SING N N 43 4S1 C17 H12 SING N N 44 4S1 C17 H13 SING N N 45 4S1 O18 H14 SING N N 46 4S1 C19 H15 SING N N 47 4S1 C19 H16 SING N N 48 4S1 C20 H17 SING N N 49 4S1 C20 H18 SING N N 50 4S1 C21 H19 SING N N 51 4S1 C21 H20 SING N N 52 4S1 C21 H21 SING N N 53 4S1 C26 H22 SING N N 54 4S1 C27 H23 SING N N 55 4S1 C28 H24 SING N N 56 4S1 C29 H25 SING N N 57 # 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 4S1 SMILES ACDLabs 12.01 "c1(nc(NCCC)ncc1c2sc3c(n2)cccc3)NC4C(O)C(O)C(C4)CO" 4S1 InChI InChI 1.03 "InChI=1S/C20H25N5O3S/c1-2-7-21-20-22-9-12(19-24-13-5-3-4-6-15(13)29-19)18(25-20)23-14-8-11(10-26)16(27)17(14)28/h3-6,9,11,14,16-17,26-28H,2,7-8,10H2,1H3,(H2,21,22,23,25)/t11-,14-,16-,17+/m1/s1" 4S1 InChIKey InChI 1.03 HIFONLZQROGEJE-PREXVCJDSA-N 4S1 SMILES_CANONICAL CACTVS 3.385 "CCCNc1ncc(c(N[C@@H]2C[C@H](CO)[C@@H](O)[C@H]2O)n1)c3sc4ccccc4n3" 4S1 SMILES CACTVS 3.385 "CCCNc1ncc(c(N[CH]2C[CH](CO)[CH](O)[CH]2O)n1)c3sc4ccccc4n3" 4S1 SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "CCCNc1ncc(c(n1)N[C@@H]2C[C@@H]([C@H]([C@H]2O)O)CO)c3nc4ccccc4s3" 4S1 SMILES "OpenEye OEToolkits" 1.9.2 "CCCNc1ncc(c(n1)NC2CC(C(C2O)O)CO)c3nc4ccccc4s3" # 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 4S1 "SYSTEMATIC NAME" ACDLabs 12.01 "(1R,2S,3R,5R)-3-{[5-(1,3-benzothiazol-2-yl)-2-(propylamino)pyrimidin-4-yl]amino}-5-(hydroxymethyl)cyclopentane-1,2-diol" 4S1 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "(1R,2S,3R,5R)-3-[[5-(1,3-benzothiazol-2-yl)-2-(propylamino)pyrimidin-4-yl]amino]-5-(hydroxymethyl)cyclopentane-1,2-diol" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 4S1 "Create component" 2015-05-17 RCSB 4S1 "Initial release" 2015-09-02 RCSB #