data_354 # _chem_comp.id 354 _chem_comp.name "N-[(S)-(4-{[(2-AMINO-4-HYDROXYQUINAZOLIN-6-YL)(DIHYDROXY)-LAMBDA~4~-SULFANYL]AMINO}PHENYL)(HYDROXY)METHYL]-L-GLUTAMIC ACID" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C20 H23 N5 O8 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2003-04-24 _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 493.490 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 354 _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details ? _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 1P4R _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 354 N2 N2 N 0 1 N N N 12.010 29.855 11.435 8.804 -3.049 0.592 N2 354 1 354 C2 C2 C 0 1 Y N N 12.518 29.699 12.740 7.847 -2.063 0.439 C2 354 2 354 N1 N1 N 0 1 Y N N 13.327 28.620 13.093 6.574 -2.401 0.507 N1 354 3 354 C8A C8A C 0 1 Y N N 13.843 28.488 14.442 5.617 -1.471 0.368 C8A 354 4 354 C4A C4A C 0 1 Y N N 13.515 29.504 15.456 6.001 -0.127 0.138 C4A 354 5 354 C5 C5 C 0 1 Y N N 14.014 29.388 16.772 5.018 0.857 -0.015 C5 354 6 354 C6 C6 C 0 1 Y N N 14.835 28.289 17.133 3.701 0.509 0.060 C6 354 7 354 C7 C7 C 0 1 Y N N 15.181 27.268 16.183 3.322 -0.811 0.286 C7 354 8 354 C8 C8 C 0 1 Y N N 14.672 27.380 14.814 4.255 -1.793 0.440 C8 354 9 354 S9 S9 S 0 1 N N N 15.397 28.226 18.762 2.429 1.781 -0.137 S9 354 10 354 O91 O91 O 0 1 N N N 14.900 29.507 19.591 3.355 2.527 -1.296 O91 354 11 354 O9 O9 O 0 1 N N N 14.743 26.916 19.301 1.262 2.948 -0.318 O9 354 12 354 N10 N10 N 0 1 N N N 17.052 27.876 18.907 1.272 0.553 -0.598 N10 354 13 354 C11 C11 C 0 1 Y N N 18.159 28.663 18.616 -0.096 0.789 -0.444 C11 354 14 354 C16 C16 C 0 1 Y N N 19.423 28.013 18.415 -0.765 1.617 -1.336 C16 354 15 354 C15 C15 C 0 1 Y N N 20.592 28.802 18.132 -2.118 1.848 -1.180 C15 354 16 354 C14 C14 C 0 1 Y N N 20.487 30.261 18.056 -2.807 1.255 -0.138 C14 354 17 354 C13 C13 C 0 1 Y N N 19.184 30.889 18.265 -2.144 0.430 0.752 C13 354 18 354 C12 C12 C 0 1 Y N N 18.047 30.097 18.538 -0.792 0.191 0.599 C12 354 19 354 C17 C17 C 0 1 N N S 21.722 31.070 17.768 -4.282 1.510 0.029 C17 354 20 354 O17 O17 O 0 1 N N N 22.853 30.674 18.136 -4.477 2.652 0.865 O17 354 21 354 N N N 0 1 N N N 21.528 32.254 17.086 -4.915 0.337 0.648 N 354 22 354 CA CA C 0 1 N N S 22.521 33.287 16.647 -6.205 0.147 -0.028 CA 354 23 354 CB CB C 0 1 N N N 23.306 32.689 15.441 -6.628 -1.319 0.081 CB 354 24 354 CG CG C 0 1 N N N 22.471 32.117 14.255 -5.636 -2.194 -0.687 CG 354 25 354 CD CD C 0 1 N N N 23.317 31.533 13.138 -6.052 -3.639 -0.580 CD 354 26 354 OE1 OE1 O 0 1 N N N 24.246 30.771 13.346 -5.324 -4.594 -1.181 OE1 354 27 354 OE2 OE2 O 0 1 N N N 22.931 31.934 11.893 -7.040 -3.938 0.047 OE2 354 28 354 C C C 0 1 N N N 21.796 34.629 16.360 -7.247 1.020 0.624 C 354 29 354 O O O 0 1 N N N 22.387 35.885 16.358 -8.509 1.012 0.169 O 354 30 354 OT OT O 0 1 N N N 20.418 34.377 16.103 -6.945 1.727 1.556 OT 354 31 354 C4 C4 C 0 1 Y N N 12.621 30.664 15.015 7.382 0.175 0.070 C4 354 32 354 O4 O4 O 0 1 N N N 12.272 31.566 15.763 7.805 1.441 -0.148 O4 354 33 354 N3 N3 N 0 1 Y N N 12.187 30.700 13.734 8.249 -0.812 0.224 N3 354 34 354 HN21 1HN2 H 0 0 N N N 11.511 28.999 11.191 9.746 -2.823 0.542 HN21 354 35 354 HN22 2HN2 H 0 0 N N N 11.418 30.645 11.177 8.533 -3.967 0.753 HN22 354 36 354 H5 H5 H 0 1 N N N 13.762 30.158 17.520 5.300 1.885 -0.190 H5 354 37 354 H7 H7 H 0 1 N N N 15.818 26.424 16.495 2.273 -1.061 0.341 H7 354 38 354 H8 H8 H 0 1 N N N 14.916 26.620 14.053 3.947 -2.813 0.616 H8 354 39 354 H91 H91 H 0 1 N N N 15.210 29.472 20.489 4.161 2.002 -1.390 H91 354 40 354 HO9 HO9 H 0 1 N N N 15.053 26.881 20.199 0.777 2.990 0.518 HO9 354 41 354 H10 H10 H 0 1 N N N 17.189 27.017 18.374 1.580 -0.292 -0.962 H10 354 42 354 H16 H16 H 0 1 N N N 19.496 26.914 18.478 -0.228 2.081 -2.150 H16 354 43 354 H15 H15 H 0 1 N N N 21.558 28.294 17.975 -2.638 2.492 -1.873 H15 354 44 354 H13 H13 H 0 1 N N N 19.056 31.983 18.216 -2.685 -0.032 1.565 H13 354 45 354 H12 H12 H 0 1 N N N 17.075 30.597 18.690 -0.275 -0.454 1.294 H12 354 46 354 H17 H17 H 0 1 N N N 22.821 30.992 17.937 -4.732 1.693 -0.946 H17 354 47 354 H1 H1 H 0 1 N N N 23.633 31.185 17.954 -4.066 2.449 1.717 H1 354 48 354 HN HN H 0 1 N N N 20.838 32.766 17.635 -4.343 -0.460 0.410 HN 354 49 354 HA HA H 0 1 N N N 23.266 33.535 17.439 -6.108 0.420 -1.079 HA 354 50 354 HB1 1HB H 0 1 N N N 24.009 31.906 15.810 -6.638 -1.617 1.130 HB1 354 51 354 HB2 2HB H 0 1 N N N 24.025 33.449 15.054 -7.625 -1.443 -0.342 HB2 354 52 354 HG1 1HG H 0 1 N N N 21.773 32.890 13.857 -5.625 -1.897 -1.736 HG1 354 53 354 HG2 2HG H 0 1 N N N 21.731 31.368 14.621 -4.639 -2.071 -0.265 HG2 354 54 354 HE1 HE1 H 0 1 N N N 24.775 30.406 12.647 -5.591 -5.520 -1.112 HE1 354 55 354 HO HO H 0 1 N N N 21.943 36.706 16.182 -9.178 1.572 0.587 HO 354 56 354 HO4 HO4 H 0 1 N N N 11.717 32.286 15.489 7.881 1.549 -1.106 HO4 354 57 # 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 354 N2 C2 SING N N 1 354 N2 HN21 SING N N 2 354 N2 HN22 SING N N 3 354 C2 N1 DOUB Y N 4 354 C2 N3 SING Y N 5 354 N1 C8A SING Y N 6 354 C8A C4A DOUB Y N 7 354 C8A C8 SING Y N 8 354 C4A C5 SING Y N 9 354 C4A C4 SING Y N 10 354 C5 C6 DOUB Y N 11 354 C5 H5 SING N N 12 354 C6 C7 SING Y N 13 354 C6 S9 SING N N 14 354 C7 C8 DOUB Y N 15 354 C7 H7 SING N N 16 354 C8 H8 SING N N 17 354 S9 O91 SING N N 18 354 S9 O9 SING N N 19 354 S9 N10 SING N N 20 354 O91 H91 SING N N 21 354 O9 HO9 SING N N 22 354 N10 C11 SING N N 23 354 N10 H10 SING N N 24 354 C11 C16 DOUB Y N 25 354 C11 C12 SING Y N 26 354 C16 C15 SING Y N 27 354 C16 H16 SING N N 28 354 C15 C14 DOUB Y N 29 354 C15 H15 SING N N 30 354 C14 C13 SING Y N 31 354 C14 C17 SING N N 32 354 C13 C12 DOUB Y N 33 354 C13 H13 SING N N 34 354 C12 H12 SING N N 35 354 C17 O17 SING N N 36 354 C17 N SING N N 37 354 C17 H17 SING N N 38 354 O17 H1 SING N N 39 354 N CA SING N N 40 354 N HN SING N N 41 354 CA CB SING N N 42 354 CA C SING N N 43 354 CA HA SING N N 44 354 CB CG SING N N 45 354 CB HB1 SING N N 46 354 CB HB2 SING N N 47 354 CG CD SING N N 48 354 CG HG1 SING N N 49 354 CG HG2 SING N N 50 354 CD OE1 SING N N 51 354 CD OE2 DOUB N N 52 354 OE1 HE1 SING N N 53 354 C O SING N N 54 354 C OT DOUB N N 55 354 O HO SING N N 56 354 C4 O4 SING N N 57 354 C4 N3 DOUB Y N 58 354 O4 HO4 SING N N 59 # 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 354 SMILES ACDLabs 10.04 "O=C(O)C(NC(O)c1ccc(cc1)NS(O)(O)c3cc2c(nc(nc2O)N)cc3)CCC(=O)O" 354 SMILES_CANONICAL CACTVS 3.341 "Nc1nc(O)c2cc(ccc2n1)[S](O)(O)Nc3ccc(cc3)[C@H](O)N[C@@H](CCC(O)=O)C(O)=O" 354 SMILES CACTVS 3.341 "Nc1nc(O)c2cc(ccc2n1)[S](O)(O)Nc3ccc(cc3)[CH](O)N[CH](CCC(O)=O)C(O)=O" 354 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1cc(ccc1C(N[C@@H](CCC(=O)O)C(=O)O)O)NS(c2ccc3c(c2)c(nc(n3)N)O)(O)O" 354 SMILES "OpenEye OEToolkits" 1.5.0 "c1cc(ccc1C(NC(CCC(=O)O)C(=O)O)O)NS(c2ccc3c(c2)c(nc(n3)N)O)(O)O" 354 InChI InChI 1.03 "InChI=1S/C20H23N5O8S/c21-20-23-14-6-5-12(9-13(14)18(29)24-20)34(32,33)25-11-3-1-10(2-4-11)17(28)22-15(19(30)31)7-8-16(26)27/h1-6,9,15,17,22,25,28,32-33H,7-8H2,(H,26,27)(H,30,31)(H3,21,23,24,29)/t15-,17?/m0/s1" 354 InChIKey InChI 1.03 JWYUKMCUDBSRPA-MYJWUSKBSA-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 354 "SYSTEMATIC NAME" ACDLabs 10.04 "N-[(S)-(4-{[(2-amino-4-hydroxyquinazolin-6-yl)(dihydroxy)-lambda~4~-sulfanyl]amino}phenyl)(hydroxy)methyl]-L-glutamic acid" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 354 "Create component" 2003-04-24 RCSB 354 "Modify descriptor" 2011-06-04 RCSB #