data_15U # _chem_comp.id 15U _chem_comp.name ;(2R,4R)-4-methyl-1-(N~2~-{[(3S)-3-methyl-1,2,3,4-tetrahydroquinolin-8-yl]sulfonyl}-L-arginyl)piperidine-2-carboxylic acid ; _chem_comp.type peptide-like _chem_comp.pdbx_type HETAIN _chem_comp.formula "C23 H36 N6 O5 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms S-argatroban _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2012-10-16 _chem_comp.pdbx_modified_date 2020-06-17 _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 508.634 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 15U _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 4HFP _chem_comp.pdbx_subcomponent_list "15Y ARG MCP" _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 15U S S S 0 1 N N N 2.627 13.756 0.106 0.930 -1.336 -2.070 S 15Y 1 15U O1 O1 O 0 1 N N N 1.796 12.587 0.188 1.964 -1.580 -1.126 O1 15Y 2 15U O2 O2 O 0 1 N N N 2.519 14.499 1.336 1.060 -1.622 -3.456 O2 15Y 3 15U C1 C1 C 0 1 N N N 2.859 12.535 -4.232 0.216 -2.450 2.069 C1 15Y 4 15U C2 C2 C 0 1 N N S 3.206 13.656 -5.211 -0.421 -3.814 2.359 C2 15Y 5 15U C3 C3 C 0 1 N N N 2.180 14.779 -5.095 -1.788 -3.852 1.672 C3 15Y 6 15U C4 C4 C 0 1 Y N N 2.018 15.182 -3.641 -1.655 -3.362 0.252 C4 15Y 7 15U C5 C5 C 0 1 Y N N 1.504 16.435 -3.308 -2.691 -3.627 -0.630 C5 15Y 8 15U C6 C6 C 0 1 Y N N 1.357 16.810 -1.970 -2.623 -3.197 -1.940 C6 15Y 9 15U C7 C7 C 0 1 Y N N 1.709 15.964 -0.914 -1.515 -2.494 -2.378 C7 15Y 10 15U C8 C8 C 0 1 Y N N 2.227 14.690 -1.137 -0.480 -2.230 -1.507 C8 15Y 11 15U C9 C9 C 0 1 Y N N 2.410 14.244 -2.548 -0.541 -2.666 -0.183 C9 15Y 12 15U C10 C10 C 0 1 N N N 3.304 13.130 -6.640 -0.596 -3.993 3.869 C10 15Y 13 15U N N N 0 1 N N N 2.910 13.024 -2.861 0.545 -2.380 0.643 N 15Y 14 15U N1 N1 N 0 1 N N N 4.146 13.289 -0.092 0.565 0.276 -1.958 N ARG 15 15U CA CA C 0 1 N N S 5.221 14.265 -0.031 0.347 0.888 -0.645 CA ARG 16 15U C C C 0 1 N N N 5.782 14.569 -1.402 -0.872 1.773 -0.700 C ARG 17 15U O O O 0 1 N N N 5.719 13.709 -2.264 -1.255 2.212 -1.763 O ARG 18 15U CB CB C 0 1 N N N 6.286 13.781 0.959 1.569 1.726 -0.263 CB ARG 19 15U CG CG C 0 1 N N N 7.159 12.658 0.411 2.800 0.822 -0.175 CG ARG 20 15U CD CD C 0 1 N N N 8.411 12.495 1.256 4.007 1.646 0.275 CD ARG 21 15U NE NE N 0 1 N N N 8.707 11.093 1.473 5.186 0.781 0.359 NE ARG 22 15U CZ CZ C 0 1 N N N 9.512 10.378 0.684 6.397 1.304 0.746 CZ ARG 23 15U NH1 NH1 N 0 1 N N N 9.637 9.072 0.924 6.502 2.640 1.054 NH1 ARG 24 15U NH2 NH2 N 0 1 N N N 10.149 10.912 -0.274 7.446 0.534 0.821 NH2 ARG 25 15U N2 N2 N 0 1 N N N 6.333 15.765 -1.651 -1.536 2.076 0.433 N MCP 26 15U C11 C11 C 0 1 N N R 6.421 16.796 -0.597 -2.800 2.823 0.383 C1 MCP 27 15U C21 C21 C 0 1 N N N 5.855 18.129 -1.110 -3.869 2.035 1.146 C2 MCP 28 15U C31 C31 C 0 1 N N R 6.396 18.520 -2.484 -3.368 1.742 2.562 C3 MCP 29 15U C41 C41 C 0 1 N N N 6.145 17.369 -3.452 -2.099 0.890 2.490 C4 MCP 30 15U C51 C51 C 0 1 N N N 6.918 16.153 -2.946 -1.013 1.660 1.742 C5 MCP 31 15U C61 C61 C 0 1 N N N 7.828 16.905 -0.060 -3.228 2.996 -1.052 C6 MCP 32 15U O11 O11 O 0 1 N N N 8.602 15.936 -0.216 -3.355 2.029 -1.765 O1 MCP 33 15U O21 O21 O 0 1 N N N 8.178 17.951 0.530 -3.468 4.224 -1.537 O2 MCP 34 15U C71 C71 C 0 1 N N N 5.805 19.833 -2.986 -3.057 3.060 3.275 C7 MCP 35 15U H1 H1 H 0 1 N N N 1.845 12.166 -4.448 -0.487 -1.656 2.322 H1 15Y 36 15U H2 H2 H 0 1 N N N 3.581 11.714 -4.351 1.125 -2.335 2.659 H2 15Y 37 15U H3 H3 H 0 1 N N N 4.189 14.062 -4.929 0.212 -4.609 1.965 H3 15Y 38 15U H4 H4 H 0 1 N N N 2.522 15.647 -5.678 -2.165 -4.875 1.670 H4 15Y 39 15U H5 H5 H 0 1 N N N 1.213 14.431 -5.487 -2.484 -3.211 2.213 H5 15Y 40 15U H6 H6 H 0 1 N N N 1.217 17.121 -4.091 -3.558 -4.174 -0.290 H6 15Y 41 15U H7 H7 H 0 1 N N N 0.958 17.788 -1.744 -3.434 -3.408 -2.622 H7 15Y 42 15U H8 H8 H 0 1 N N N 1.576 16.307 0.101 -1.461 -2.155 -3.402 H8 15Y 43 15U H9 H9 H 0 1 N N N 4.051 12.324 -6.684 -1.074 -4.952 4.069 H9 15Y 44 15U H10 H10 H 0 1 N N N 2.325 12.740 -6.955 0.380 -3.965 4.353 H10 15Y 45 15U H11 H11 H 0 1 N N N 3.606 13.947 -7.311 -1.219 -3.188 4.260 H11 15Y 46 15U H12 H12 H 0 1 N N N 2.416 12.359 -2.301 0.952 -1.487 0.410 H12 15Y 47 15U H13 H13 H 0 1 N N N 4.200 12.856 -0.992 0.496 0.815 -2.762 H ARG 48 15U H14 H14 H 0 1 N N N 4.809 15.203 0.370 0.195 0.106 0.099 HA ARG 49 15U H15 H15 H 0 1 N N N 6.934 14.632 1.217 1.734 2.493 -1.020 HB2 ARG 50 15U H16 H16 H 0 1 N N N 5.780 13.418 1.865 1.396 2.200 0.703 HB3 ARG 51 15U H17 H17 H 0 1 N N N 6.589 11.717 0.424 2.615 0.025 0.545 HG2 ARG 52 15U H18 H18 H 0 1 N N N 7.449 12.897 -0.623 3.002 0.386 -1.154 HG3 ARG 53 15U H19 H19 H 0 1 N N N 9.259 12.967 0.738 4.192 2.443 -0.446 HD2 ARG 54 15U H20 H20 H 0 1 N N N 8.256 12.985 2.228 3.806 2.082 1.253 HD3 ARG 55 15U H21 H21 H 0 1 N N N 8.285 10.636 2.256 5.112 -0.162 0.142 HE ARG 56 15U H22 H22 H 0 1 N N N 9.134 8.652 1.680 5.721 3.213 0.998 HH11 ARG 57 15U H23 H23 H 0 1 N N N 10.233 8.513 0.348 7.356 3.009 1.327 HH12 ARG 58 15U H24 H24 H 0 1 N N N 9.967 11.893 -0.344 7.372 -0.409 0.604 HH21 ARG 59 15U H26 H26 H 0 1 N N N 5.779 16.475 0.236 -2.665 3.801 0.844 H1 MCP 60 15U H27 H27 H 0 1 N N N 6.117 18.920 -0.392 -4.786 2.622 1.199 H21 MCP 61 15U H28 H28 H 0 1 N N N 4.760 18.042 -1.176 -4.068 1.096 0.629 H22 MCP 62 15U H29 H29 H 0 1 N N N 7.484 18.653 -2.392 -4.137 1.203 3.115 H3 MCP 63 15U H30 H30 H 0 1 N N N 6.496 17.643 -4.458 -1.754 0.661 3.498 H41 MCP 64 15U H31 H31 H 0 1 N N N 5.070 17.139 -3.489 -2.318 -0.037 1.961 H42 MCP 65 15U H32 H32 H 0 1 N N N 6.826 15.324 -3.663 -0.141 1.020 1.602 H51 MCP 66 15U H33 H33 H 0 1 N N N 7.980 16.410 -2.817 -0.731 2.544 2.314 H52 MCP 67 15U H34 H34 H 0 1 N N N 9.081 17.868 0.814 -3.740 4.285 -2.463 HO2 MCP 68 15U H35 H35 H 0 1 N N N 6.011 20.631 -2.257 -3.960 3.667 3.327 H71 MCP 69 15U H36 H36 H 0 1 N N N 6.260 20.094 -3.953 -2.700 2.852 4.284 H72 MCP 70 15U H37 H37 H 0 1 N N N 4.718 19.722 -3.111 -2.288 3.600 2.721 H73 MCP 71 # # 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 15U C10 C2 SING N N 1 15U C2 C3 SING N N 2 15U C2 C1 SING N N 3 15U C3 C4 SING N N 4 15U C1 N SING N N 5 15U C4 C5 DOUB Y N 6 15U C4 C9 SING Y N 7 15U C41 C51 SING N N 8 15U C41 C31 SING N N 9 15U C5 C6 SING Y N 10 15U C71 C31 SING N N 11 15U C51 N2 SING N N 12 15U N C9 SING N N 13 15U C9 C8 DOUB Y N 14 15U C31 C21 SING N N 15 15U O C DOUB N N 16 15U C6 C7 DOUB Y N 17 15U N2 C SING N N 18 15U N2 C11 SING N N 19 15U C CA SING N N 20 15U C8 C7 SING Y N 21 15U C8 S SING N N 22 15U C21 C11 SING N N 23 15U C11 C61 SING N N 24 15U NH2 CZ DOUB N N 25 15U O11 C61 DOUB N N 26 15U N1 CA SING N N 27 15U N1 S SING N N 28 15U C61 O21 SING N N 29 15U CA CB SING N N 30 15U S O1 DOUB N N 31 15U S O2 DOUB N N 32 15U CG CB SING N N 33 15U CG CD SING N N 34 15U CZ NH1 SING N N 35 15U CZ NE SING N N 36 15U CD NE SING N N 37 15U C1 H1 SING N N 38 15U C1 H2 SING N N 39 15U C2 H3 SING N N 40 15U C3 H4 SING N N 41 15U C3 H5 SING N N 42 15U C5 H6 SING N N 43 15U C6 H7 SING N N 44 15U C7 H8 SING N N 45 15U C10 H9 SING N N 46 15U C10 H10 SING N N 47 15U C10 H11 SING N N 48 15U N H12 SING N N 49 15U N1 H13 SING N N 50 15U CA H14 SING N N 51 15U CB H15 SING N N 52 15U CB H16 SING N N 53 15U CG H17 SING N N 54 15U CG H18 SING N N 55 15U CD H19 SING N N 56 15U CD H20 SING N N 57 15U NE H21 SING N N 58 15U NH1 H22 SING N N 59 15U NH1 H23 SING N N 60 15U NH2 H24 SING N N 61 15U C11 H26 SING N N 62 15U C21 H27 SING N N 63 15U C21 H28 SING N N 64 15U C31 H29 SING N N 65 15U C41 H30 SING N N 66 15U C41 H31 SING N N 67 15U C51 H32 SING N N 68 15U C51 H33 SING N N 69 15U O21 H34 SING N N 70 15U C71 H35 SING N N 71 15U C71 H36 SING N N 72 15U C71 H37 SING N N 73 # # 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 15U SMILES ACDLabs 12.01 "O=C(N1C(C(=O)O)CC(C)CC1)C(NS(=O)(=O)c3cccc2c3NCC(C)C2)CCCNC(=[N@H])N" 15U InChI InChI 1.03 "InChI=1S/C23H36N6O5S/c1-14-8-10-29(18(12-14)22(31)32)21(30)17(6-4-9-26-23(24)25)28-35(33,34)19-7-3-5-16-11-15(2)13-27-20(16)19/h3,5,7,14-15,17-18,27-28H,4,6,8-13H2,1-2H3,(H,31,32)(H4,24,25,26)/t14-,15+,17+,18-/m1/s1" 15U InChIKey InChI 1.03 KXNPVXPOPUZYGB-MXSMSXNCSA-N 15U SMILES_CANONICAL CACTVS 3.370 "C[C@@H]1CCN([C@H](C1)C(O)=O)C(=O)[C@H](CCCNC(N)=N)N[S](=O)(=O)c2cccc3C[C@H](C)CNc23" 15U SMILES CACTVS 3.370 "C[CH]1CCN([CH](C1)C(O)=O)C(=O)[CH](CCCNC(N)=N)N[S](=O)(=O)c2cccc3C[CH](C)CNc23" 15U SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "[H]/N=C(\N)/NCCC[C@@H](C(=O)N1CC[C@H](C[C@@H]1C(=O)O)C)NS(=O)(=O)c2cccc3c2NC[C@H](C3)C" 15U SMILES "OpenEye OEToolkits" 1.7.6 "CC1CCN(C(C1)C(=O)O)C(=O)C(CCCNC(=N)N)NS(=O)(=O)c2cccc3c2NCC(C3)C" # # 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 15U "SYSTEMATIC NAME" ACDLabs 12.01 "(2R,4R)-4-methyl-1-(N~2~-{[(3S)-3-methyl-1,2,3,4-tetrahydroquinolin-8-yl]sulfonyl}-L-arginyl)piperidine-2-carboxylic acid" 15U "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "(2R,4R)-1-[(2S)-5-carbamimidamido-2-[[(3S)-3-methyl-1,2,3,4-tetrahydroquinolin-8-yl]sulfonylamino]pentanoyl]-4-methyl-piperidine-2-carboxylic 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 15U "Create component" 2012-10-16 RCSB 15U "Initial release" 2013-03-13 RCSB 15U "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 15U _pdbx_chem_comp_synonyms.name S-argatroban _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##