data_339 # _chem_comp.id 339 _chem_comp.name "(S)-2-(3-((R)-1-(4-BROMOPHENYL)ETHYL)UREIDO)-N-((S)-1-((S)-5-GUANIDINO-1-OXO-1-(THIAZOL-2-YL)PENTAN-2-YLAMINO)-3-METHYL-1-OXOBUTAN-2-YL)-5-UREIDOPENTANAMIDE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C29 H45 Br N10 O5 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2005-05-25 _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 725.701 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 339 _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 1ZOM _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 339 CX CX C 0 1 N N N 11.517 51.160 25.099 -6.547 1.068 -1.754 CX 339 1 339 CY CY C 0 1 N N S 11.880 51.214 23.583 -5.954 0.781 -0.399 CY 339 2 339 CZ CZ C 0 1 Y N N 11.728 52.561 25.752 -7.754 0.362 -2.189 CZ 339 3 339 OX OX O 0 1 N N N 10.137 50.807 25.171 -6.025 1.884 -2.485 OX 339 4 339 N1 N1 N 0 1 N N N 13.339 51.557 23.459 -4.593 1.319 -0.337 N1 339 5 339 C2 C2 C 0 1 N N N 11.668 49.861 22.888 -6.813 1.439 0.683 C2 339 6 339 C3 C3 C 0 1 N N N 12.011 49.914 21.400 -6.283 1.045 2.064 C3 339 7 339 C4 C4 C 0 1 N N N 11.804 48.569 20.743 -7.142 1.704 3.146 C4 339 8 339 N5 N5 N 0 1 N N N 11.758 48.807 19.305 -6.634 1.326 4.471 N5 339 9 339 C6 C6 C 0 1 N N N 11.339 47.980 18.342 -7.497 1.987 5.459 C6 339 10 339 N7 N7 N 0 1 N N N 11.152 46.663 18.559 -8.787 1.287 5.529 N7 339 11 339 N8 N8 N 0 1 N N N 11.112 48.507 17.143 -6.849 1.953 6.777 N8 339 12 339 N9 N9 N 0 1 Y N N 12.747 52.844 26.510 -8.467 -0.561 -1.551 N9 339 13 339 C10 C10 C 0 1 Y N N 12.653 54.178 26.932 -9.526 -1.071 -2.115 C10 339 14 339 C11 C11 C 0 1 Y N N 11.519 54.817 26.431 -9.892 -0.663 -3.366 C11 339 15 339 S12 S12 S 0 1 Y N N 10.585 53.800 25.460 -8.657 0.505 -3.724 S12 339 16 339 N13 N13 N 0 1 N N N 15.855 53.384 21.696 -1.184 0.113 -0.951 N13 339 17 339 C14 C14 C 0 1 N N S 15.469 52.754 23.010 -2.175 1.187 -0.841 C14 339 18 339 C15 C15 C 0 1 N N N 13.911 52.698 23.046 -3.559 0.591 -0.801 C15 339 19 339 O16 O16 O 0 1 N N N 13.245 53.674 22.695 -3.741 -0.545 -1.187 O16 339 20 339 C17 C17 C 0 1 N N N 15.986 53.598 24.234 -2.055 2.117 -2.050 C17 339 21 339 C18 C18 C 0 1 N N N 17.179 52.867 24.842 -0.673 2.772 -2.054 C18 339 22 339 C19 C19 C 0 1 N N N 16.490 55.023 23.856 -2.241 1.309 -3.336 C19 339 23 339 N20 N20 N 0 1 N N N 16.220 55.114 19.534 2.374 -0.333 -0.081 N20 339 24 339 C21 C21 C 0 1 N N S 16.038 53.700 19.206 1.094 -0.793 -0.624 C21 339 25 339 C22 C22 C 0 1 N N N 15.577 52.906 20.440 0.075 0.311 -0.511 C22 339 26 339 O23 O23 O 0 1 N N N 14.959 51.858 20.242 0.387 1.377 -0.025 O23 339 27 339 C24 C24 C 0 1 N N N 17.344 53.137 18.653 0.614 -2.013 0.164 C24 339 28 339 C25 C25 C 0 1 N N N 17.595 53.624 17.232 1.586 -3.175 -0.052 C25 339 29 339 C26 C26 C 0 1 N N N 18.882 53.062 16.692 1.106 -4.395 0.737 C26 339 30 339 N27 N27 N 0 1 N N N 18.826 53.131 15.232 2.037 -5.507 0.530 N27 339 31 339 C28 C28 C 0 1 N N N 19.827 52.996 14.346 1.815 -6.693 1.131 C28 339 32 339 N29 N29 N 0 1 N N N 19.600 52.729 13.062 2.671 -7.716 0.941 N29 339 33 339 O30 O30 O 0 1 N N N 21.061 53.142 14.767 0.842 -6.839 1.845 O30 339 34 339 C31 C31 C 0 1 N N N 15.237 56.020 19.457 3.525 -0.895 -0.500 C31 339 35 339 O32 O32 O 0 1 N N N 14.076 55.682 19.086 3.501 -1.784 -1.329 O32 339 36 339 N33 N33 N 0 1 N N N 15.548 57.306 19.810 4.703 -0.472 0.000 N33 339 37 339 C34 C34 C 0 1 N N R 14.603 58.480 19.840 5.954 -1.083 -0.455 C34 339 38 339 C35 C35 C 0 1 Y N N 13.453 58.214 20.884 7.088 -0.108 -0.267 C35 339 39 339 C36 C36 C 0 1 Y N N 12.238 59.016 20.833 7.139 0.682 0.867 C36 339 40 339 C37 C37 C 0 1 Y N N 11.163 58.781 21.779 8.181 1.573 1.042 C37 339 41 339 C38 C38 C 0 1 Y N N 11.283 57.739 22.798 9.167 1.682 0.078 C38 339 42 339 C39 C39 C 0 1 Y N N 12.472 56.943 22.864 9.112 0.897 -1.059 C39 339 43 339 C40 C40 C 0 1 Y N N 13.541 57.162 21.939 8.072 0.002 -1.231 C40 339 44 339 BR41 BR41 BR 0 0 N N N 9.905 57.407 24.035 10.588 2.907 0.313 BR41 339 45 339 C42 C42 C 0 1 N N N 15.368 59.754 20.232 6.230 -2.348 0.360 C42 339 46 339 HY HY H 0 1 N N N 11.228 51.962 23.108 -5.927 -0.296 -0.235 HY 339 47 339 HN1 HN1 H 0 1 N N N 13.974 50.830 23.722 -4.437 2.200 0.037 HN1 339 48 339 H21A 1H2 H 0 0 N N N 10.604 49.596 22.981 -6.768 2.523 0.573 H21A 339 49 339 H22 2H2 H 0 1 N N N 12.316 49.115 23.370 -7.845 1.105 0.581 H22 339 50 339 H31 1H3 H 0 1 N N N 13.070 50.194 21.295 -6.328 -0.038 2.174 H31 339 51 339 H32 2H3 H 0 1 N N N 11.360 50.653 20.911 -5.251 1.379 2.166 H32 339 52 339 H41 1H4 H 0 1 N N N 10.874 48.098 21.094 -7.098 2.787 3.035 H41 339 53 339 H42 2H4 H 0 1 N N N 12.632 47.889 20.993 -8.174 1.370 3.044 H42 339 54 339 HN5 HN5 H 0 1 N N N 11.152 49.598 19.216 -6.789 0.333 4.569 HN5 339 55 339 H6 H6 H 0 1 N N N 11.239 47.017 18.864 -7.661 3.023 5.161 H6 339 56 339 HN71 1HN7 H 0 0 N N N 11.914 46.302 19.096 -8.586 0.338 5.806 HN71 339 57 339 HN72 2HN7 H 0 0 N N N 11.106 46.184 17.683 -9.304 1.707 6.286 HN72 339 58 339 HN81 1HN8 H 0 0 N N N 11.860 48.264 16.525 -6.024 2.529 6.709 HN81 339 59 339 HN82 2HN8 H 0 0 N N N 11.055 49.502 17.221 -7.474 2.416 7.419 HN82 339 60 339 H10 H10 H 0 1 N N N 13.378 54.657 27.573 -10.110 -1.817 -1.596 H10 339 61 339 H11 H11 H 0 1 N N N 11.267 55.846 26.641 -10.728 -0.982 -3.972 H11 339 62 339 H13 H13 H 0 1 N N N 16.368 54.241 21.745 -1.434 -0.739 -1.340 H13 339 63 339 H14 H14 H 0 1 N N N 15.921 51.754 23.087 -1.997 1.753 0.073 H14 339 64 339 H17 H17 H 0 1 N N N 15.131 53.709 24.918 -2.823 2.889 -1.991 H17 339 65 339 H181 1H18 H 0 0 N N N 16.847 51.903 25.254 -0.629 3.523 -2.842 H181 339 66 339 H182 2H18 H 0 0 N N N 17.614 53.480 25.646 -0.493 3.247 -1.089 H182 339 67 339 H183 3H18 H 0 0 N N N 17.937 52.691 24.064 0.089 2.013 -2.233 H183 339 68 339 H191 1H19 H 0 0 N N N 15.758 55.506 23.192 -1.473 0.538 -3.394 H191 339 69 339 H192 2H19 H 0 0 N N N 17.458 54.944 23.340 -3.226 0.843 -3.333 H192 339 70 339 H193 3H19 H 0 0 N N N 16.609 55.625 24.769 -2.156 1.972 -4.197 H193 339 71 339 H20 H20 H 0 1 N N N 17.125 55.420 19.831 2.394 0.376 0.581 H20 339 72 339 H21 H21 H 0 1 N N N 15.254 53.606 18.441 1.221 -1.065 -1.672 H21 339 73 339 H241 1H24 H 0 0 N N N 17.273 52.039 18.639 0.573 -1.767 1.225 H241 339 74 339 H242 2H24 H 0 0 N N N 18.174 53.467 19.295 -0.379 -2.302 -0.181 H242 339 75 339 H251 1H25 H 0 0 N N N 17.667 54.722 17.243 1.628 -3.421 -1.113 H251 339 76 339 H252 2H25 H 0 0 N N N 16.764 53.298 16.589 2.579 -2.887 0.294 H252 339 77 339 H261 1H26 H 0 0 N N N 19.012 52.020 17.021 1.065 -4.148 1.798 H261 339 78 339 H262 2H26 H 0 0 N N N 19.734 53.650 17.064 0.114 -4.683 0.392 H262 339 79 339 H27 H27 H 0 1 N N N 17.922 53.301 14.841 2.814 -5.390 -0.039 H27 339 80 339 H291 1H29 H 0 0 N N N 18.693 52.610 12.659 3.448 -7.599 0.372 H291 339 81 339 H292 2H29 H 0 0 N N N 20.459 52.664 12.555 2.511 -8.569 1.374 H292 339 82 339 H33 H33 H 0 1 N N N 16.496 57.484 20.074 4.723 0.237 0.662 H33 339 83 339 H34 H34 H 0 1 N N N 14.163 58.612 18.840 5.869 -1.342 -1.511 H34 339 84 339 H36 H36 H 0 1 N N N 12.137 59.790 20.087 6.369 0.596 1.619 H36 339 85 339 H37 H37 H 0 1 N N N 10.266 59.381 21.730 8.224 2.186 1.930 H37 339 86 339 H39 H39 H 0 1 N N N 12.562 56.173 23.616 9.881 0.982 -1.812 H39 339 87 339 H40 H40 H 0 1 N N N 14.431 56.553 22.005 8.030 -0.612 -2.119 H40 339 88 339 H421 1H42 H 0 0 N N N 14.771 60.638 19.961 6.316 -2.089 1.415 H421 339 89 339 H422 2H42 H 0 0 N N N 16.329 59.783 19.698 5.411 -3.054 0.224 H422 339 90 339 H423 3H42 H 0 0 N N N 15.551 59.753 21.317 7.161 -2.803 0.021 H423 339 91 # 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 339 CX CY SING N N 1 339 CX CZ SING N N 2 339 CX OX DOUB N N 3 339 CY N1 SING N N 4 339 CY C2 SING N N 5 339 CY HY SING N N 6 339 CZ N9 DOUB Y N 7 339 CZ S12 SING Y N 8 339 N1 C15 SING N N 9 339 N1 HN1 SING N N 10 339 C2 C3 SING N N 11 339 C2 H21A SING N N 12 339 C2 H22 SING N N 13 339 C3 C4 SING N N 14 339 C3 H31 SING N N 15 339 C3 H32 SING N N 16 339 C4 N5 SING N N 17 339 C4 H41 SING N N 18 339 C4 H42 SING N N 19 339 N5 C6 SING N N 20 339 N5 HN5 SING N N 21 339 C6 N7 SING N N 22 339 C6 N8 SING N N 23 339 C6 H6 SING N N 24 339 N7 HN71 SING N N 25 339 N7 HN72 SING N N 26 339 N8 HN81 SING N N 27 339 N8 HN82 SING N N 28 339 N9 C10 SING Y N 29 339 C10 C11 DOUB Y N 30 339 C10 H10 SING N N 31 339 C11 S12 SING Y N 32 339 C11 H11 SING N N 33 339 N13 C14 SING N N 34 339 N13 C22 SING N N 35 339 N13 H13 SING N N 36 339 C14 C15 SING N N 37 339 C14 C17 SING N N 38 339 C14 H14 SING N N 39 339 C15 O16 DOUB N N 40 339 C17 C18 SING N N 41 339 C17 C19 SING N N 42 339 C17 H17 SING N N 43 339 C18 H181 SING N N 44 339 C18 H182 SING N N 45 339 C18 H183 SING N N 46 339 C19 H191 SING N N 47 339 C19 H192 SING N N 48 339 C19 H193 SING N N 49 339 N20 C21 SING N N 50 339 N20 C31 SING N N 51 339 N20 H20 SING N N 52 339 C21 C22 SING N N 53 339 C21 C24 SING N N 54 339 C21 H21 SING N N 55 339 C22 O23 DOUB N N 56 339 C24 C25 SING N N 57 339 C24 H241 SING N N 58 339 C24 H242 SING N N 59 339 C25 C26 SING N N 60 339 C25 H251 SING N N 61 339 C25 H252 SING N N 62 339 C26 N27 SING N N 63 339 C26 H261 SING N N 64 339 C26 H262 SING N N 65 339 N27 C28 SING N N 66 339 N27 H27 SING N N 67 339 C28 N29 SING N N 68 339 C28 O30 DOUB N N 69 339 N29 H291 SING N N 70 339 N29 H292 SING N N 71 339 C31 O32 DOUB N N 72 339 C31 N33 SING N N 73 339 N33 C34 SING N N 74 339 N33 H33 SING N N 75 339 C34 C35 SING N N 76 339 C34 C42 SING N N 77 339 C34 H34 SING N N 78 339 C35 C36 SING Y N 79 339 C35 C40 DOUB Y N 80 339 C36 C37 DOUB Y N 81 339 C36 H36 SING N N 82 339 C37 C38 SING Y N 83 339 C37 H37 SING N N 84 339 C38 C39 DOUB Y N 85 339 C38 BR41 SING N N 86 339 C39 C40 SING Y N 87 339 C39 H39 SING N N 88 339 C40 H40 SING N N 89 339 C42 H421 SING N N 90 339 C42 H422 SING N N 91 339 C42 H423 SING N N 92 # 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 339 SMILES ACDLabs 10.04 "O=C(c1nccs1)C(NC(=O)C(NC(=O)C(NC(=O)NC(c2ccc(Br)cc2)C)CCCNC(=O)N)C(C)C)CCCNC(N)N" 339 SMILES_CANONICAL CACTVS 3.341 "CC(C)[C@H](NC(=O)[C@H](CCCNC(N)=O)NC(=O)N[C@H](C)c1ccc(Br)cc1)C(=O)N[C@@H](CCCNC(N)N)C(=O)c2sccn2" 339 SMILES CACTVS 3.341 "CC(C)[CH](NC(=O)[CH](CCCNC(N)=O)NC(=O)N[CH](C)c1ccc(Br)cc1)C(=O)N[CH](CCCNC(N)N)C(=O)c2sccn2" 339 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CC(C)[C@@H](C(=O)N[C@@H](CCCNC(N)N)C(=O)c1nccs1)NC(=O)[C@H](CCCNC(=O)N)NC(=O)N[C@H](C)c2ccc(cc2)Br" 339 SMILES "OpenEye OEToolkits" 1.5.0 "CC(C)C(C(=O)NC(CCCNC(N)N)C(=O)c1nccs1)NC(=O)C(CCCNC(=O)N)NC(=O)NC(C)c2ccc(cc2)Br" 339 InChI InChI 1.03 ;InChI=1S/C29H45BrN10O5S/c1-16(2)22(25(43)38-20(6-4-12-35-27(31)32)23(41)26-34-14-15-46-26)40-24(42)21(7-5-13-36-28(33)44)39-29(45)37-17(3)18-8-10-19(30)11-9-18/h8-11,14-17,20-22,27,35H,4-7,12-13,31-32H2,1-3H3,(H,38,43)(H,40,42)(H3,33,36,44)(H2,37,39,45)/t17-,20+,21+,22+/m1/s1 ; 339 InChIKey InChI 1.03 HWZOXFNZLMNLSU-MNAPGUCWSA-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 339 "SYSTEMATIC NAME" ACDLabs 10.04 "2-[N~2~-{[(1R)-1-(4-bromophenyl)ethyl]carbamoyl}-N~5~-carbamoyl-L-ornithyl-L-valyl-N~5~-(diaminomethyl)-L-ornithyl]-1,3-thiazole" 339 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-5-(aminocarbonylamino)-2-[[(1R)-1-(4-bromophenyl)ethyl]carbamoylamino]-N-[(2S)-1-[[(2S)-5-(diaminomethylamino)-1-oxo-1-(1,3-thiazol-2-yl)pentan-2-yl]amino]-3-methyl-1-oxo-butan-2-yl]pentanamide" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 339 "Create component" 2005-05-25 RCSB 339 "Modify descriptor" 2011-06-04 RCSB #