data_6EK # _chem_comp.id 6EK _chem_comp.name "(2S,3S)-2-{[(2S)-3-(2-amino-1H-imidazol-5-yl)-2-{[(2S,4S)-5-(carbamoyloxy)-4-hydroxy-2-({[(2S,3S)-3-hydroxypiperidin-2-yl]carbonyl}amino)pentanoyl]amino}propanoyl]amino}-3-(2-chloro-1H-imidazol-5-yl)-3-hydroxypropanoic acid" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C24 H35 Cl N10 O10" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2016-03-23 _chem_comp.pdbx_modified_date 2016-04-22 _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 659.049 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 6EK _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 5IWA _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 6EK C10 C1 C 0 1 N N N 311.047 187.319 17.962 -2.817 -0.050 -1.094 C10 6EK 1 6EK C15 C2 C 0 1 Y N N 309.380 181.776 18.162 -5.646 0.668 1.658 C15 6EK 2 6EK C17 C3 C 0 1 N N N 312.110 183.765 18.037 -5.442 -0.333 -2.854 C17 6EK 3 6EK C20 C4 C 0 1 N N N 304.180 186.832 18.861 3.092 -3.800 -0.339 C20 6EK 4 6EK C21 C5 C 0 1 N N N 304.535 184.694 19.994 4.465 -5.752 -0.371 C21 6EK 5 6EK C22 C6 C 0 1 N N N 311.623 189.714 17.395 -1.779 2.178 -1.421 C22 6EK 6 6EK C24 C7 C 0 1 Y N N 315.136 189.106 18.510 1.124 4.273 -0.627 C24 6EK 7 6EK C01 C8 C 0 1 N N N 307.750 195.161 16.417 6.478 3.021 1.839 C01 6EK 8 6EK C02 C9 C 0 1 N N N 306.362 195.508 16.735 7.827 2.389 1.486 C02 6EK 9 6EK C03 C10 C 0 1 N N N 305.367 194.767 15.879 7.715 0.866 1.592 C03 6EK 10 6EK N01 N1 N 0 1 N N N 305.509 193.328 16.031 6.674 0.386 0.674 N01 6EK 11 6EK C04 C11 C 0 1 N N S 306.883 192.819 15.890 5.361 0.942 1.023 C04 6EK 12 6EK C05 C12 C 0 1 N N S 307.964 193.880 15.730 5.403 2.467 0.900 C05 6EK 13 6EK O01 O1 O 0 1 N N N 308.138 194.231 14.403 4.130 3.010 1.259 O01 6EK 14 6EK C06 C13 C 0 1 N N N 307.222 191.818 17.027 4.317 0.392 0.085 C06 6EK 15 6EK N02 N2 N 0 1 N N N 306.812 190.421 16.973 3.015 0.423 0.433 N02 6EK 16 6EK C07 C14 C 0 1 N N S 307.116 189.451 18.043 2.001 -0.112 -0.478 C07 6EK 17 6EK C08 C15 C 0 1 N N N 308.650 189.192 18.151 0.676 0.551 -0.200 C08 6EK 18 6EK N03 N3 N 0 1 N N N 309.417 188.696 17.008 -0.411 0.213 -0.922 N03 6EK 19 6EK C09 C16 C 0 1 N N S 310.841 188.430 17.031 -1.698 0.858 -0.652 C09 6EK 20 6EK N04 N4 N 0 1 N N N 310.836 185.910 17.565 -4.099 0.339 -0.948 N04 6EK 21 6EK C11 C17 C 0 1 N N S 311.098 184.814 18.596 -5.186 -0.541 -1.383 C11 6EK 22 6EK C12 C18 C 0 1 N N S 309.904 184.111 19.212 -6.455 -0.213 -0.594 C12 6EK 23 6EK O09 O2 O 0 1 N N N 310.213 183.417 20.382 -6.888 1.110 -0.915 O09 6EK 24 6EK N05 N5 N 0 1 Y N N 308.379 183.483 17.197 -6.377 -1.387 1.693 N05 6EK 25 6EK C14 C19 C 0 1 Y N N 308.028 182.354 16.567 -5.989 -1.036 2.939 C14 6EK 26 6EK N06 N6 N 0 1 Y N N 308.635 181.300 17.151 -5.549 0.193 2.909 N06 6EK 27 6EK C16 C20 C 0 1 Y N N 309.228 183.155 18.198 -6.165 -0.302 0.883 C16 6EK 28 6EK CL CL1 CL 0 0 N N N 306.954 182.255 15.203 -6.057 -2.054 4.344 CL 6EK 29 6EK O02 O3 O 0 1 N N N 312.833 184.059 17.025 -4.784 0.468 -3.474 O02 6EK 30 6EK O03 O4 O 0 1 N N N 312.215 182.653 18.570 -6.402 -1.037 -3.474 O03 6EK 31 6EK O04 O5 O 0 1 N N N 309.220 189.408 19.252 0.588 1.388 0.673 O04 6EK 32 6EK O05 O6 O 0 1 N N N 311.406 187.562 19.105 -2.564 -1.129 -1.587 O05 6EK 33 6EK O06 O7 O 0 1 N N N 307.849 192.222 17.972 4.649 -0.079 -0.982 O06 6EK 34 6EK C18 C21 C 0 1 N N N 306.281 188.122 17.977 1.870 -1.622 -0.266 C18 6EK 35 6EK C19 C22 C 0 1 N N S 304.859 188.200 18.577 3.177 -2.308 -0.667 C19 6EK 36 6EK O07 O8 O 0 1 N N N 305.045 185.848 19.385 4.372 -4.430 -0.609 O07 6EK 37 6EK N07 N7 N 0 1 N N N 304.070 184.747 21.370 5.626 -6.397 -0.601 N07 6EK 38 6EK O08 O9 O 0 1 N N N 304.749 183.614 19.500 3.504 -6.362 0.051 O08 6EK 39 6EK O O10 O 0 1 N N N 304.880 188.983 19.706 3.392 -2.141 -2.070 O 6EK 40 6EK C23 C23 C 0 1 Y N N 313.166 189.554 17.603 -0.738 3.131 -0.893 C23 6EK 41 6EK N08 N8 N 0 1 Y N N 313.798 189.061 18.707 0.524 3.332 -1.405 N08 6EK 42 6EK C C24 C 0 1 Y N N 314.175 189.932 16.718 -0.861 3.940 0.173 C 6EK 43 6EK N09 N9 N 0 1 Y N N 315.369 189.639 17.287 0.284 4.629 0.315 N09 6EK 44 6EK N N10 N 0 1 N N N 316.152 188.657 19.457 2.407 4.767 -0.798 N 6EK 45 6EK H1 H1 H 0 1 N N N 309.991 181.188 18.831 -5.362 1.658 1.331 H1 6EK 46 6EK H2 H2 H 0 1 N N N 303.367 186.995 19.584 2.840 -3.927 0.714 H2 6EK 47 6EK H3 H3 H 0 1 N N N 303.761 186.454 17.917 2.321 -4.264 -0.955 H3 6EK 48 6EK H4 H4 H 0 1 N N N 311.468 190.441 16.584 -1.599 1.994 -2.480 H4 6EK 49 6EK H5 H5 H 0 1 N N N 311.199 190.111 18.329 -2.770 2.614 -1.291 H5 6EK 50 6EK H6 H6 H 0 1 N N N 308.312 195.132 17.362 6.221 2.778 2.871 H6 6EK 51 6EK H7 H7 H 0 1 N N N 308.155 195.957 15.774 6.542 4.103 1.725 H7 6EK 52 6EK H8 H8 H 0 1 N N N 306.225 196.588 16.579 8.102 2.664 0.468 H8 6EK 53 6EK H9 H9 H 0 1 N N N 306.171 195.262 17.790 8.589 2.747 2.178 H9 6EK 54 6EK H10 H10 H 0 1 N N N 305.532 195.034 14.825 8.670 0.412 1.327 H10 6EK 55 6EK H11 H11 H 0 1 N N N 304.349 195.060 16.177 7.453 0.591 2.613 H11 6EK 56 6EK H12 H12 H 0 1 N N N 305.178 193.078 16.941 6.912 0.595 -0.284 H12 6EK 57 6EK H14 H14 H 0 1 N N N 306.902 192.229 14.962 5.110 0.667 2.047 H14 6EK 58 6EK H15 H15 H 0 1 N N N 308.901 193.447 16.110 5.640 2.743 -0.127 H15 6EK 59 6EK H16 H16 H 0 1 N N N 308.817 194.892 14.336 4.084 3.974 1.205 H16 6EK 60 6EK H17 H17 H 0 1 N N N 306.301 190.105 16.174 2.750 0.800 1.287 H17 6EK 61 6EK H18 H18 H 0 1 N N N 306.830 189.931 18.990 2.297 0.086 -1.508 H18 6EK 62 6EK H19 H19 H 0 1 N N N 308.925 188.529 16.153 -0.340 -0.456 -1.621 H19 6EK 63 6EK H20 H20 H 0 1 N N N 311.162 188.115 16.027 -1.790 1.053 0.416 H20 6EK 64 6EK H21 H21 H 0 1 N N N 310.529 185.680 16.642 -4.302 1.202 -0.554 H21 6EK 65 6EK H22 H22 H 0 1 N N N 311.619 185.307 19.430 -4.906 -1.579 -1.207 H22 6EK 66 6EK H23 H23 H 0 1 N N N 309.163 184.888 19.453 -7.239 -0.925 -0.853 H23 6EK 67 6EK H24 H24 H 0 1 N N N 310.627 184.007 21.001 -6.239 1.797 -0.710 H24 6EK 68 6EK H25 H25 H 0 1 N N N 308.068 184.405 16.968 -6.744 -2.243 1.424 H25 6EK 69 6EK H27 H27 H 0 1 N N N 312.871 182.142 18.110 -6.529 -0.869 -4.418 H27 6EK 70 6EK H28 H28 H 0 1 N N N 306.188 187.832 16.920 1.661 -1.824 0.785 H28 6EK 71 6EK H29 H29 H 0 1 N N N 306.837 187.345 18.522 1.055 -2.006 -0.879 H29 6EK 72 6EK H30 H30 H 0 1 N N N 304.234 188.700 17.822 4.006 -1.862 -0.117 H30 6EK 73 6EK H31 H31 H 0 1 N N N 303.934 183.901 21.885 6.394 -5.910 -0.938 H31 6EK 74 6EK H32 H32 H 0 1 N N N 303.886 185.630 21.802 5.693 -7.349 -0.429 H32 6EK 75 6EK H33 H33 H 0 1 N N N 304.006 189.031 20.075 2.692 -2.515 -2.622 H33 6EK 76 6EK H34 H34 H 0 1 N N N 313.345 188.721 19.531 0.912 2.887 -2.175 H34 6EK 77 6EK H35 H35 H 0 1 N N N 314.030 190.381 15.747 -1.733 4.025 0.805 H35 6EK 78 6EK H37 H37 H 0 1 N N N 317.061 188.802 19.066 2.960 4.439 -1.524 H37 6EK 79 6EK H38 H38 H 0 1 N N N 316.068 189.177 20.307 2.752 5.440 -0.191 H38 6EK 80 # 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 6EK O01 C05 SING N N 1 6EK CL C14 SING N N 2 6EK C05 C04 SING N N 3 6EK C05 C01 SING N N 4 6EK C03 N01 SING N N 5 6EK C03 C02 SING N N 6 6EK C04 N01 SING N N 7 6EK C04 C06 SING N N 8 6EK C01 C02 SING N N 9 6EK C14 N06 DOUB Y N 10 6EK C14 N05 SING Y N 11 6EK C N09 SING Y N 12 6EK C C23 DOUB Y N 13 6EK N02 C06 SING N N 14 6EK N02 C07 SING N N 15 6EK N03 C09 SING N N 16 6EK N03 C08 SING N N 17 6EK O02 C17 DOUB N N 18 6EK C06 O06 DOUB N N 19 6EK C09 C22 SING N N 20 6EK C09 C10 SING N N 21 6EK N06 C15 SING Y N 22 6EK N05 C16 SING Y N 23 6EK N09 C24 DOUB Y N 24 6EK C22 C23 SING N N 25 6EK N04 C10 SING N N 26 6EK N04 C11 SING N N 27 6EK C23 N08 SING Y N 28 6EK C10 O05 DOUB N N 29 6EK C18 C07 SING N N 30 6EK C18 C19 SING N N 31 6EK C17 O03 SING N N 32 6EK C17 C11 SING N N 33 6EK C07 C08 SING N N 34 6EK C08 O04 DOUB N N 35 6EK C15 C16 DOUB Y N 36 6EK C16 C12 SING N N 37 6EK C24 N08 SING Y N 38 6EK C24 N SING N N 39 6EK C19 C20 SING N N 40 6EK C19 O SING N N 41 6EK C11 C12 SING N N 42 6EK C20 O07 SING N N 43 6EK C12 O09 SING N N 44 6EK O07 C21 SING N N 45 6EK O08 C21 DOUB N N 46 6EK C21 N07 SING N N 47 6EK C15 H1 SING N N 48 6EK C20 H2 SING N N 49 6EK C20 H3 SING N N 50 6EK C22 H4 SING N N 51 6EK C22 H5 SING N N 52 6EK C01 H6 SING N N 53 6EK C01 H7 SING N N 54 6EK C02 H8 SING N N 55 6EK C02 H9 SING N N 56 6EK C03 H10 SING N N 57 6EK C03 H11 SING N N 58 6EK N01 H12 SING N N 59 6EK C04 H14 SING N N 60 6EK C05 H15 SING N N 61 6EK O01 H16 SING N N 62 6EK N02 H17 SING N N 63 6EK C07 H18 SING N N 64 6EK N03 H19 SING N N 65 6EK C09 H20 SING N N 66 6EK N04 H21 SING N N 67 6EK C11 H22 SING N N 68 6EK C12 H23 SING N N 69 6EK O09 H24 SING N N 70 6EK N05 H25 SING N N 71 6EK O03 H27 SING N N 72 6EK C18 H28 SING N N 73 6EK C18 H29 SING N N 74 6EK C19 H30 SING N N 75 6EK N07 H31 SING N N 76 6EK N07 H32 SING N N 77 6EK O H33 SING N N 78 6EK N08 H34 SING N N 79 6EK C H35 SING N N 80 6EK N H37 SING N N 81 6EK N H38 SING N N 82 # 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 6EK SMILES ACDLabs 12.01 "C(=O)(C(Cc1nc(N)nc1)NC(C(NC(C2NCCCC2O)=O)CC(COC(N)=O)O)=O)NC(C(O)=O)C(O)c3cnc(n3)Cl" 6EK InChI InChI 1.03 ;InChI=1S/C24H35ClN10O10/c25-22-29-7-13(34-22)17(38)16(21(42)43)35-19(40)11(4-9-6-30-23(26)31-9)32-18(39)12(5-10(36)8-45-24(27)44)33-20(41)15-14(37)2-1-3-28-15/h6-7,10-12,14-17,28,36-38H,1-5,8H2,(H2,27,44)(H,29,34)(H,32,39)(H,33,41)(H,35,40)(H,42,43)(H3,26,30,31)/t10-,11-,12-,14-,15-,16-,17+/m0/s1 ; 6EK InChIKey InChI 1.03 UFNFLYFKIYFJJJ-PLHJXKGHSA-N 6EK SMILES_CANONICAL CACTVS 3.385 "NC(=O)OC[C@@H](O)C[C@H](NC(=O)[C@H]1NCCC[C@@H]1O)C(=O)N[C@@H](Cc2[nH]c(N)nc2)C(=O)N[C@@H]([C@H](O)c3[nH]c(Cl)nc3)C(O)=O" 6EK SMILES CACTVS 3.385 "NC(=O)OC[CH](O)C[CH](NC(=O)[CH]1NCCC[CH]1O)C(=O)N[CH](Cc2[nH]c(N)nc2)C(=O)N[CH]([CH](O)c3[nH]c(Cl)nc3)C(O)=O" 6EK SMILES_CANONICAL "OpenEye OEToolkits" 2.0.4 "c1c([nH]c(n1)N)C[C@@H](C(=O)N[C@@H]([C@@H](c2cnc([nH]2)Cl)O)C(=O)O)NC(=O)[C@H](C[C@@H](COC(=O)N)O)NC(=O)[C@@H]3[C@H](CCCN3)O" 6EK SMILES "OpenEye OEToolkits" 2.0.4 "c1c([nH]c(n1)N)CC(C(=O)NC(C(c2cnc([nH]2)Cl)O)C(=O)O)NC(=O)C(CC(COC(=O)N)O)NC(=O)C3C(CCCN3)O" # 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 6EK "SYSTEMATIC NAME" ACDLabs 12.01 "(2S,3S)-2-{[(2S)-3-(2-amino-1H-imidazol-5-yl)-2-{[(2S,4S)-5-(carbamoyloxy)-4-hydroxy-2-({[(2S,3S)-3-hydroxypiperidin-2-yl]carbonyl}amino)pentanoyl]amino}propanoyl]amino}-3-(2-chloro-1H-imidazol-5-yl)-3-hydroxypropanoic acid (non-preferred name)" 6EK "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.4 ;(2~{S},3~{S})-2-[[(2~{S})-2-[[(2~{S},4~{S})-5-aminocarbonyloxy-4-oxidanyl-2-[[(2~{S},3~{S})-3-oxidanylpiperidin-2-yl]carbonylamino]pentanoyl]amino]-3-(2-azanyl-1~{H}-imidazol-5-yl)propanoyl]amino]-3-(2-chloranyl-1~{H}-imidazol-5-yl)-3-oxidanyl-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 6EK "Create component" 2016-03-23 EBI 6EK "Initial release" 2016-04-27 RCSB #