data_SXM # _chem_comp.id SXM _chem_comp.name "3-{[2-({N-[(2S)-2-hydroxy-3,3-dimethyl-4-(phosphonooxy)butanoyl]-beta-alanyl}amino)ethyl]sulfanyl}-3-oxopropanoic acid" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C14 H25 N2 O10 P S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "THIOMALONIC ACID S-{2-[3-(2-HYDROXY-3,3-DIMETHYL-4-PHOSPHONOOXY-BUTYRYLAMINO)-PROPIONYLAMINO]-ETHYL} ESTER" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2009-03-30 _chem_comp.pdbx_modified_date 2021-03-13 _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 444.394 _chem_comp.one_letter_code ? _chem_comp.three_letter_code SXM _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 2KG8 _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 SXM P24 P24 P 0 1 N N N 8.979 9.864 0.008 6.264 2.410 -0.347 P24 SXM 1 SXM O26 O26 O 0 1 N Y N 9.343 9.593 -1.396 4.964 2.938 -1.136 O26 SXM 2 SXM O23 O23 O 0 1 N Y N 9.906 10.667 0.843 6.865 3.601 0.554 O23 SXM 3 SXM O27 O27 O 0 1 N N N 7.565 10.513 0.077 5.852 1.175 0.600 O27 SXM 4 SXM C28 C28 C 0 1 N N N 7.365 11.791 -0.609 5.384 -0.075 0.090 C28 SXM 5 SXM C29 C29 C 0 1 N N N 5.988 12.393 -0.267 5.084 -1.021 1.255 C29 SXM 6 SXM C30 C30 C 0 1 N N N 4.943 11.422 -0.763 6.359 -1.248 2.069 C30 SXM 7 SXM C31 C31 C 0 1 N N N 5.841 12.563 1.239 4.010 -0.401 2.151 C31 SXM 8 SXM C32 C32 C 0 1 N N S 5.764 13.798 -0.980 4.583 -2.359 0.709 C32 SXM 9 SXM O33 O33 O 0 1 N N N 5.384 13.661 -2.360 5.630 -2.997 -0.025 O33 SXM 10 SXM C34 C34 C 0 1 N N N 6.982 14.720 -0.904 3.405 -2.121 -0.200 C34 SXM 11 SXM O35 O35 O 0 1 N N N 7.770 14.745 0.059 3.530 -2.244 -1.400 O35 SXM 12 SXM N36 N36 N 0 1 N N N 7.121 15.459 -1.956 2.211 -1.772 0.320 N36 SXM 13 SXM C37 C37 C 0 1 N N N 8.202 16.418 -2.187 1.041 -1.646 -0.552 C37 SXM 14 SXM C38 C38 C 0 1 N N N 8.236 16.942 -3.637 -0.176 -1.242 0.284 C38 SXM 15 SXM C39 C39 C 0 1 N N N 8.205 15.837 -4.700 -1.380 -1.112 -0.613 C39 SXM 16 SXM O40 O40 O 0 1 N N N 8.188 14.629 -4.403 -1.275 -1.321 -1.803 O40 SXM 17 SXM N41 N41 N 0 1 N N N 8.199 16.254 -5.943 -2.573 -0.762 -0.093 N41 SXM 18 SXM C42 C42 C 0 1 N N N 8.151 15.346 -7.070 -3.743 -0.636 -0.965 C42 SXM 19 SXM C43 C43 C 0 1 N N N 9.245 15.590 -8.081 -4.960 -0.232 -0.129 C43 SXM 20 SXM S1 S1 S 0 1 N N N 9.179 14.317 -9.247 -6.406 -0.075 -1.206 S1 SXM 21 SXM C1 C1 C 0 1 N N N 9.572 12.962 -8.200 -7.590 0.371 -0.052 C1 SXM 22 SXM O1 O1 O 0 1 N N N 10.225 13.055 -7.126 -7.285 0.485 1.116 O1 SXM 23 SXM C2 C2 C 0 1 N N N 9.071 11.613 -8.692 -9.010 0.622 -0.488 C2 SXM 24 SXM C3 C3 C 0 1 N N N 7.553 11.374 -8.651 -9.844 0.996 0.710 C3 SXM 25 SXM O3A O3A O 0 1 N N N 7.102 10.339 -9.203 -9.337 1.054 1.805 O3A SXM 26 SXM O3B O3B O 0 1 N N N 6.782 12.185 -8.063 -11.151 1.266 0.560 O3B SXM 27 SXM H28 H28 H 0 1 N N N 8.150 12.493 -0.293 4.475 0.086 -0.490 H28 SXM 28 SXM H28A H28A H 0 0 N N N 7.423 11.626 -1.695 6.149 -0.516 -0.548 H28A SXM 29 SXM H30 H30 H 0 1 N N N 3.940 11.815 -0.538 6.666 -0.310 2.533 H30 SXM 30 SXM H30A H30A H 0 0 N N N 5.050 11.292 -1.850 6.169 -1.991 2.843 H30A SXM 31 SXM H30B H30B H 0 0 N N N 5.077 10.452 -0.262 7.152 -1.603 1.411 H30B SXM 32 SXM H31 H31 H 0 1 N N N 6.628 13.236 1.610 4.412 0.486 2.640 H31 SXM 33 SXM H31A H31A H 0 0 N N N 4.854 12.993 1.465 3.147 -0.123 1.546 H31A SXM 34 SXM H31B H31B H 0 0 N N N 5.935 11.583 1.729 3.705 -1.125 2.907 H31B SXM 35 SXM H32 H32 H 0 1 N N N 4.940 14.258 -0.414 4.279 -2.999 1.538 H32 SXM 36 SXM HO33 HO33 H 0 0 N N N 5.262 14.522 -2.742 5.951 -2.483 -0.779 HO33 SXM 37 SXM HN36 HN36 H 0 0 N N N 6.430 15.367 -2.673 2.128 -1.605 1.272 HN36 SXM 38 SXM H37 H37 H 0 1 N N N 9.159 15.919 -1.976 1.232 -0.884 -1.308 H37 SXM 39 SXM H37A H37A H 0 0 N N N 8.056 17.274 -1.512 0.846 -2.601 -1.039 H37A SXM 40 SXM H38 H38 H 0 1 N N N 7.355 17.583 -3.787 -0.366 -2.003 1.040 H38 SXM 41 SXM H38A H38A H 0 0 N N N 9.166 17.515 -3.770 0.019 -0.287 0.771 H38A SXM 42 SXM HN41 HN41 H 0 0 N N N 8.229 17.238 -6.120 -2.657 -0.595 0.859 HN41 SXM 43 SXM H42 H42 H 0 1 N N N 8.258 14.320 -6.689 -3.553 0.126 -1.721 H42 SXM 44 SXM H42A H42A H 0 0 N N N 7.182 15.475 -7.574 -3.938 -1.591 -1.452 H42A SXM 45 SXM H43 H43 H 0 1 N N N 9.093 16.561 -8.574 -5.151 -0.993 0.627 H43 SXM 46 SXM H43A H43A H 0 0 N N N 10.225 15.594 -7.582 -4.765 0.723 0.358 H43A SXM 47 SXM H2 H2 H 0 1 N N N 9.384 11.517 -9.742 -9.030 1.435 -1.213 H2 SXM 48 SXM H2A H2A H 0 1 N N N 9.535 10.845 -8.055 -9.415 -0.282 -0.945 H2A SXM 49 SXM HO26 HO26 H 0 0 N Y N 10.130 9.061 -1.423 4.252 3.246 -0.559 HO26 SXM 50 SXM HO23 HO23 H 0 0 N Y N 10.734 10.209 0.928 7.135 4.379 0.047 HO23 SXM 51 SXM HO3B HO3B H 0 0 N N N 5.887 11.873 -8.125 -11.645 1.502 1.357 HO3B SXM 52 SXM O10 O10 O 0 1 N N N 10.197 9.042 0.051 7.285 1.964 -1.322 O10 SXM 53 # # 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 SXM P24 O27 SING N N 1 SXM P24 O23 SING N N 2 SXM O26 P24 SING N N 3 SXM O26 HO26 SING N N 4 SXM O23 HO23 SING N N 5 SXM C28 O27 SING N N 6 SXM C28 H28 SING N N 7 SXM C28 C29 SING N N 8 SXM C29 C31 SING N N 9 SXM C30 C29 SING N N 10 SXM C30 H30 SING N N 11 SXM C30 H30A SING N N 12 SXM C31 H31A SING N N 13 SXM C31 H31B SING N N 14 SXM C31 H31 SING N N 15 SXM C32 C29 SING N N 16 SXM C32 C34 SING N N 17 SXM C32 H32 SING N N 18 SXM O33 C32 SING N N 19 SXM C34 O35 DOUB N N 20 SXM N36 C34 SING N N 21 SXM C37 N36 SING N N 22 SXM C37 H37A SING N N 23 SXM C37 H37 SING N N 24 SXM C38 C37 SING N N 25 SXM C39 C38 SING N N 26 SXM C39 O40 DOUB N N 27 SXM N41 C39 SING N N 28 SXM C42 N41 SING N N 29 SXM C42 H42 SING N N 30 SXM C43 C42 SING N N 31 SXM C43 H43 SING N N 32 SXM S1 C43 SING N N 33 SXM S1 C1 SING N N 34 SXM C1 O1 DOUB N N 35 SXM C2 C1 SING N N 36 SXM C2 C3 SING N N 37 SXM C2 H2 SING N N 38 SXM C3 O3B SING N N 39 SXM O3A C3 DOUB N N 40 SXM O3B HO3B SING N N 41 SXM H28A C28 SING N N 42 SXM H30B C30 SING N N 43 SXM HO33 O33 SING N N 44 SXM HN36 N36 SING N N 45 SXM H38 C38 SING N N 46 SXM H38A C38 SING N N 47 SXM HN41 N41 SING N N 48 SXM H42A C42 SING N N 49 SXM H43A C43 SING N N 50 SXM H2A C2 SING N N 51 SXM P24 O10 DOUB N N 52 # # 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 SXM SMILES ACDLabs 10.04 "O=C(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(O)O)CC(=O)O" SXM SMILES_CANONICAL CACTVS 3.352 "CC(C)(CO[P](O)(O)=O)[C@H](O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O" SXM SMILES CACTVS 3.352 "CC(C)(CO[P](O)(O)=O)[CH](O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O" SXM SMILES_CANONICAL "OpenEye OEToolkits" 1.7.0 "CC(C)(COP(=O)(O)O)[C@@H](C(=O)NCCC(=O)NCCSC(=O)CC(=O)O)O" SXM SMILES "OpenEye OEToolkits" 1.7.0 "CC(C)(COP(=O)(O)O)C(C(=O)NCCC(=O)NCCSC(=O)CC(=O)O)O" SXM InChI InChI 1.03 "InChI=1S/C14H25N2O10PS/c1-14(2,8-26-27(23,24)25)12(21)13(22)16-4-3-9(17)15-5-6-28-11(20)7-10(18)19/h12,21H,3-8H2,1-2H3,(H,15,17)(H,16,22)(H,18,19)(H2,23,24,25)/t12-/m1/s1" SXM InChIKey InChI 1.03 RNFWAFOKCVKQGB-GFCCVEGCSA-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 SXM "SYSTEMATIC NAME" ACDLabs 10.04 "3-{[2-({N-[(2S)-2-hydroxy-3,3-dimethyl-4-(phosphonooxy)butanoyl]-beta-alanyl}amino)ethyl]sulfanyl}-3-oxopropanoic acid" SXM "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.6.1 "3-[2-[3-[[(2S)-2-hydroxy-3,3-dimethyl-4-phosphonooxy-butanoyl]amino]propanoylamino]ethylsulfanyl]-3-oxo-propanoic 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 SXM "Create component" 2009-03-30 RCSB SXM "Modify descriptor" 2011-06-04 RCSB SXM "Modify synonyms" 2021-03-13 RCSB # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id SXM _pdbx_chem_comp_synonyms.name "THIOMALONIC ACID S-{2-[3-(2-HYDROXY-3,3-DIMETHYL-4-PHOSPHONOOXY-BUTYRYLAMINO)-PROPIONYLAMINO]-ETHYL} ESTER" _pdbx_chem_comp_synonyms.provenance PDB _pdbx_chem_comp_synonyms.type ? ##