data_C4M # _chem_comp.id C4M _chem_comp.name "N-[(2R,3S)-3-AMINO-2-HYDROXY-4-PHENYLBUTYL]-4-METHOXY-2,3,6-TRIMETHYLBENZENESULFONAMIDE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C20 H28 N2 O4 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "INHIBITOR OF THROMBIN" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2005-12-09 _chem_comp.pdbx_modified_date 2021-03-01 _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 392.512 _chem_comp.one_letter_code ? _chem_comp.three_letter_code C4M _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 2C93 _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 C4M C1 C1 C 0 1 N N N -1.833 20.049 47.224 4.326 4.011 -0.745 C1 C4M 1 C4M O2 O2 O 0 1 N N N -0.829 20.048 46.185 4.743 3.123 0.295 O2 C4M 2 C4M C3 C3 C 0 1 Y N N 0.337 19.453 46.592 4.099 1.944 0.086 C3 C4M 3 C4M C4 C4 C 0 1 Y N N 0.451 18.958 47.875 3.232 1.807 -0.989 C4 C4M 4 C4M C5 C5 C 0 1 Y N N 1.607 18.338 48.318 2.579 0.608 -1.200 C5 C4M 5 C4M C6 C6 C 0 1 N N N 1.588 17.843 49.751 1.638 0.458 -2.367 C6 C4M 6 C4M C7 C7 C 0 1 Y N N 2.695 18.184 47.468 2.789 -0.455 -0.340 C7 C4M 7 C4M C8 C8 C 0 1 Y N N 2.596 18.682 46.164 3.651 -0.320 0.732 C8 C4M 8 C4M C9 C9 C 0 1 N N N 3.755 18.547 45.191 3.877 -1.480 1.667 C9 C4M 9 C4M C10 C10 C 0 1 Y N N 1.422 19.306 45.726 4.312 0.875 0.943 C10 C4M 10 C4M C11 C11 C 0 1 N N N 1.334 19.828 44.309 5.252 1.021 2.112 C11 C4M 11 C4M S12 S12 S 0 1 N N N 4.177 17.378 48.028 1.955 -1.983 -0.611 S12 C4M 12 C4M O13 O13 O 0 1 N N N 3.865 16.831 49.314 2.760 -2.977 0.007 O13 C4M 13 C4M O14 O14 O 0 1 N N N 4.620 16.588 46.941 1.565 -1.973 -1.978 O14 C4M 14 C4M N15 N15 N 0 1 N N N 5.331 18.501 48.352 0.546 -1.939 0.259 N15 C4M 15 C4M C16 C16 C 0 1 N N N 5.146 19.470 49.437 -0.498 -0.971 -0.085 C16 C4M 16 C4M C17 C17 C 0 1 N N R 6.532 20.000 49.843 -1.808 -1.371 0.595 C17 C4M 17 C4M O18 O18 O 0 1 N N N 7.070 20.840 48.808 -1.658 -1.276 2.013 O18 C4M 18 C4M C19 C19 C 0 1 N N S 6.426 20.773 51.153 -2.927 -0.433 0.137 C19 C4M 19 C4M N20 N20 N 0 1 N N N 7.758 21.245 51.519 -3.082 -0.530 -1.320 N20 C4M 20 C4M C21 C21 C 0 1 N N N 5.515 21.995 50.995 -4.238 -0.833 0.817 C21 C4M 21 C4M C22 C22 C 0 1 Y N N 4.058 21.678 51.278 -5.312 0.164 0.463 C22 C4M 22 C4M C23 C23 C 0 1 Y N N 3.077 22.077 50.366 -5.513 1.275 1.260 C23 C4M 23 C4M C24 C24 C 0 1 Y N N 1.738 21.816 50.595 -6.495 2.192 0.933 C24 C4M 24 C4M C25 C25 C 0 1 Y N N 1.363 21.155 51.752 -7.282 1.991 -0.186 C25 C4M 25 C4M C26 C26 C 0 1 Y N N 2.329 20.750 52.661 -7.085 0.877 -0.979 C26 C4M 26 C4M C27 C27 C 0 1 Y N N 3.678 21.013 52.434 -6.100 -0.037 -0.655 C27 C4M 27 C4M H1C1 1H1C H 0 0 N N N -2.461 19.151 47.128 4.596 3.589 -1.713 H1C1 C4M 28 C4M H1C2 2H1C H 0 0 N N N -2.460 20.947 47.127 3.246 4.146 -0.696 H1C2 C4M 29 C4M H1C3 3H1C H 0 0 N N N -1.343 20.049 48.209 4.819 4.975 -0.618 H1C3 C4M 30 C4M H4 H4 H 0 1 N N N -0.384 19.057 48.552 3.069 2.637 -1.661 H4 C4M 31 C4M H6C1 1H6C H 0 0 N N N 0.685 18.217 50.256 2.162 -0.014 -3.198 H6C1 C4M 32 C4M H6C2 2H6C H 0 0 N N N 2.482 18.210 50.277 0.791 -0.161 -2.073 H6C2 C4M 33 C4M H6C3 3H6C H 0 0 N N N 1.583 16.743 49.759 1.281 1.441 -2.674 H6C3 C4M 34 C4M H9C1 1H9C H 0 0 N N N 4.307 17.620 45.405 4.635 -2.142 1.248 H9C1 C4M 35 C4M H9C2 2H9C H 0 0 N N N 4.429 19.409 45.302 4.215 -1.107 2.634 H9C2 C4M 36 C4M H9C3 3H9C H 0 0 N N N 3.368 18.514 44.162 2.945 -2.030 1.795 H9C3 C4M 37 C4M H111 1H11 H 0 0 N N N 0.416 19.450 43.836 6.257 0.730 1.808 H111 C4M 38 C4M H112 2H11 H 0 0 N N N 2.209 19.486 43.737 5.259 2.059 2.445 H112 C4M 39 C4M H113 3H11 H 0 0 N N N 1.313 20.928 44.323 4.919 0.380 2.928 H113 C4M 40 C4M H15 H15 H 0 1 N N N 6.157 17.987 48.582 0.413 -2.555 0.996 H15 C4M 41 C4M H161 1H16 H 0 0 N N N 4.654 18.991 50.296 -0.200 0.021 0.255 H161 C4M 42 C4M H162 2H16 H 0 0 N N N 4.512 20.301 49.094 -0.638 -0.957 -1.166 H162 C4M 43 C4M H17 H17 H 0 1 N N N 7.212 19.148 49.985 -2.060 -2.396 0.324 H17 C4M 44 C4M H18 H18 H 0 1 N N N 7.189 21.721 49.144 -1.436 -0.356 2.209 H18 C4M 45 C4M H19 H19 H 0 1 N N N 6.007 20.109 51.923 -2.675 0.593 0.408 H19 C4M 46 C4M H201 1H20 H 0 0 N N N 7.683 22.125 51.987 -3.314 -1.491 -1.524 H201 C4M 47 C4M H202 2H20 H 0 0 N N N 8.312 21.353 50.694 -3.892 0.021 -1.563 H202 C4M 48 C4M H211 1H21 H 0 0 N N N 5.587 22.333 49.951 -4.536 -1.824 0.477 H211 C4M 49 C4M H212 2H21 H 0 0 N N N 5.846 22.769 51.703 -4.097 -0.846 1.898 H212 C4M 50 C4M H23 H23 H 0 1 N N N 3.370 22.598 49.467 -4.898 1.432 2.134 H23 C4M 51 C4M H24 H24 H 0 1 N N N 0.992 22.125 49.878 -6.649 3.063 1.552 H24 C4M 52 C4M H25 H25 H 0 1 N N N 0.320 20.955 51.947 -8.052 2.705 -0.440 H25 C4M 53 C4M H26 H26 H 0 1 N N N 2.032 20.224 53.556 -7.700 0.720 -1.853 H26 C4M 54 C4M H27 H27 H 0 1 N N N 4.422 20.702 53.152 -5.945 -0.908 -1.275 H27 C4M 55 # # 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 C4M C1 O2 SING N N 1 C4M C1 H1C1 SING N N 2 C4M C1 H1C2 SING N N 3 C4M C1 H1C3 SING N N 4 C4M O2 C3 SING N N 5 C4M C3 C4 DOUB Y N 6 C4M C3 C10 SING Y N 7 C4M C4 C5 SING Y N 8 C4M C4 H4 SING N N 9 C4M C5 C6 SING N N 10 C4M C5 C7 DOUB Y N 11 C4M C6 H6C1 SING N N 12 C4M C6 H6C2 SING N N 13 C4M C6 H6C3 SING N N 14 C4M C7 C8 SING Y N 15 C4M C7 S12 SING N N 16 C4M C8 C9 SING N N 17 C4M C8 C10 DOUB Y N 18 C4M C9 H9C1 SING N N 19 C4M C9 H9C2 SING N N 20 C4M C9 H9C3 SING N N 21 C4M C10 C11 SING N N 22 C4M C11 H111 SING N N 23 C4M C11 H112 SING N N 24 C4M C11 H113 SING N N 25 C4M S12 O13 DOUB N N 26 C4M S12 O14 DOUB N N 27 C4M S12 N15 SING N N 28 C4M N15 C16 SING N N 29 C4M N15 H15 SING N N 30 C4M C16 C17 SING N N 31 C4M C16 H161 SING N N 32 C4M C16 H162 SING N N 33 C4M C17 O18 SING N N 34 C4M C17 C19 SING N N 35 C4M C17 H17 SING N N 36 C4M O18 H18 SING N N 37 C4M C19 N20 SING N N 38 C4M C19 C21 SING N N 39 C4M C19 H19 SING N N 40 C4M N20 H201 SING N N 41 C4M N20 H202 SING N N 42 C4M C21 C22 SING N N 43 C4M C21 H211 SING N N 44 C4M C21 H212 SING N N 45 C4M C22 C23 SING Y N 46 C4M C22 C27 DOUB Y N 47 C4M C23 C24 DOUB Y N 48 C4M C23 H23 SING N N 49 C4M C24 C25 SING Y N 50 C4M C24 H24 SING N N 51 C4M C25 C26 DOUB Y N 52 C4M C25 H25 SING N N 53 C4M C26 C27 SING Y N 54 C4M C26 H26 SING N N 55 C4M C27 H27 SING N N 56 # # 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 C4M SMILES ACDLabs 10.04 "O=S(=O)(c1c(cc(OC)c(c1C)C)C)NCC(O)C(N)Cc2ccccc2" C4M SMILES_CANONICAL CACTVS 3.341 "COc1cc(C)c(c(C)c1C)[S](=O)(=O)NC[C@@H](O)[C@@H](N)Cc2ccccc2" C4M SMILES CACTVS 3.341 "COc1cc(C)c(c(C)c1C)[S](=O)(=O)NC[CH](O)[CH](N)Cc2ccccc2" C4M SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "Cc1cc(c(c(c1S(=O)(=O)NC[C@H]([C@H](Cc2ccccc2)N)O)C)C)OC" C4M SMILES "OpenEye OEToolkits" 1.5.0 "Cc1cc(c(c(c1S(=O)(=O)NCC(C(Cc2ccccc2)N)O)C)C)OC" C4M InChI InChI 1.03 "InChI=1S/C20H28N2O4S/c1-13-10-19(26-4)14(2)15(3)20(13)27(24,25)22-12-18(23)17(21)11-16-8-6-5-7-9-16/h5-10,17-18,22-23H,11-12,21H2,1-4H3/t17-,18+/m0/s1" C4M InChIKey InChI 1.03 HORGTFOBJRCVMO-ZWKOTPCHSA-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 C4M "SYSTEMATIC NAME" ACDLabs 10.04 "N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-4-methoxy-2,3,6-trimethylbenzenesulfonamide" C4M "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "N-[(2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl]-4-methoxy-2,3,6-trimethyl-benzenesulfonamide" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site C4M "Create component" 2005-12-09 EBI C4M "Modify descriptor" 2011-06-04 RCSB C4M "Modify synonyms" 2021-03-01 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id C4M _pdbx_chem_comp_synonyms.name "INHIBITOR OF THROMBIN" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##