data_BUK # _chem_comp.id BUK _chem_comp.name "N~2~-({[(1R)-1-(4-BROMOPHENYL)ETHYL]AMINO}CARBONYL)ASPARAGINYL-N~1~-{4-{[AMINO(IMINO)METHYL]AMINO}-1-[2,3-DIHYDRO-1,3-THIAZOL-2-YL(HYDROXY)METHYL]BUTYL}VALINAMIDE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C27 H42 Br N9 O5 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "N-((R)-1-(4-BROMOPHENYL)ETHYL)UREA-ASN-VAL-ARG-ALPHA-KETOTHIAZOLE" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2005-06-09 _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 684.649 _chem_comp.one_letter_code ? _chem_comp.three_letter_code BUK _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 1ZPZ _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 BUK CX CX C 0 1 N N S -1.005 20.649 7.148 -6.619 -1.446 -1.070 CX BUK 1 BUK CY CY C 0 1 N N S -1.213 19.644 8.313 -5.806 -0.292 -0.480 CY BUK 2 BUK CZ CZ C 0 1 N N S -0.307 21.923 7.630 -7.989 -1.504 -0.391 CZ BUK 3 BUK OX OX O 0 1 N N N -0.209 19.984 6.157 -6.792 -1.238 -2.474 OX BUK 4 BUK N02 N02 N 0 1 N N N -2.067 20.295 9.322 -4.463 -0.291 -1.065 N02 BUK 5 BUK C06 C06 C 0 1 N N N -1.913 18.348 7.849 -6.500 1.035 -0.796 C06 BUK 6 BUK C07 C07 C 0 1 N N N -2.232 17.408 9.021 -5.757 2.177 -0.101 C07 BUK 7 BUK C08 C08 C 0 1 N N N -2.806 16.086 8.558 -6.451 3.504 -0.417 C08 BUK 8 BUK N09 N09 N 0 1 N N N -2.803 15.180 9.704 -5.739 4.598 0.248 N09 BUK 9 BUK C10 C10 C 0 1 N N N -3.104 13.879 9.722 -6.182 5.892 0.109 C10 BUK 10 BUK N11 N11 N 0 1 N N N -3.836 13.313 8.751 -5.514 6.919 0.733 N11 BUK 11 BUK NP2 NP2 N 0 1 N N N -2.644 13.153 10.732 -7.236 6.145 -0.615 NP2 BUK 12 BUK N13 N13 N 0 1 N N N -0.985 22.992 7.839 -8.770 -2.670 -0.857 N13 BUK 13 BUK C14 C14 C 0 1 N N N -0.133 24.006 8.277 -9.092 -3.594 0.112 C14 BUK 14 BUK C15 C15 C 0 1 N N N 1.191 23.589 8.366 -8.732 -3.453 1.377 C15 BUK 15 BUK S16 S16 S 0 1 N N N 1.397 21.958 7.912 -7.831 -1.910 1.396 S16 BUK 16 BUK N17 N17 N 0 1 N N N -2.651 20.856 12.790 -1.147 -1.344 0.002 N17 BUK 17 BUK C18 C18 C 0 1 N N S -2.814 21.386 11.400 -2.088 -0.980 -1.061 C18 BUK 18 BUK C19 C19 C 0 1 N N N -1.703 20.750 10.522 -3.498 -1.068 -0.536 C19 BUK 19 BUK O20 O20 O 0 1 N N N -0.536 20.676 10.936 -3.763 -1.839 0.362 O20 BUK 20 BUK C21 C21 C 0 1 N N N -2.710 22.945 11.349 -1.921 -1.941 -2.240 C21 BUK 21 BUK C22 C22 C 0 1 N N N -4.009 23.586 11.872 -2.856 -1.521 -3.376 C22 BUK 22 BUK C23 C23 C 0 1 N N N -1.530 23.489 12.185 -0.472 -1.900 -2.730 C23 BUK 23 BUK N24 N24 N 0 1 N N N -1.714 20.105 15.252 2.384 -0.630 0.802 N24 BUK 24 BUK C25 C25 C 0 1 N N S -2.544 19.123 14.586 1.085 -1.255 1.064 C25 BUK 25 BUK C26 C26 C 0 1 N N N -2.732 19.541 13.130 0.118 -0.881 -0.030 C26 BUK 26 BUK O27 O27 O 0 1 N N N -2.957 18.657 12.312 0.478 -0.162 -0.938 O27 BUK 27 BUK C28 C28 C 0 1 N N N -3.905 19.033 15.305 0.546 -0.767 2.410 C28 BUK 28 BUK C29 C29 C 0 1 N N N -3.771 18.593 16.778 0.439 0.736 2.394 C29 BUK 29 BUK O30 O30 O 0 1 N N N -2.668 18.342 17.286 0.695 1.351 1.380 O30 BUK 30 BUK N31 N31 N 0 1 N N N -4.884 18.484 17.494 0.060 1.397 3.505 N31 BUK 31 BUK C32 C32 C 0 1 N N N -0.379 20.057 15.312 3.510 -1.184 1.293 C32 BUK 32 BUK O33 O33 O 0 1 N N N 0.261 19.121 14.774 3.459 -2.252 1.873 O33 BUK 33 BUK N34 N34 N 0 1 N N N 0.212 21.077 15.980 4.692 -0.556 1.141 N34 BUK 34 BUK C35 C35 C 0 1 N N R 1.652 21.282 16.185 5.916 -1.159 1.674 C35 BUK 35 BUK C36 C36 C 0 1 Y N N 2.334 21.426 14.821 7.105 -0.654 0.898 C36 BUK 36 BUK C37 C37 C 0 1 Y N N 3.602 20.796 14.584 7.164 0.672 0.510 C37 BUK 37 BUK C38 C38 C 0 1 Y N N 4.247 20.932 13.325 8.256 1.137 -0.198 C38 BUK 38 BUK C39 C39 C 0 1 Y N N 3.639 21.699 12.281 9.286 0.274 -0.526 C39 BUK 39 BUK C40 C40 C 0 1 Y N N 2.385 22.327 12.499 9.224 -1.054 -0.142 C40 BUK 40 BUK C41 C41 C 0 1 Y N N 1.732 22.199 13.751 8.134 -1.517 0.570 C41 BUK 41 BUK BR BR BR 0 0 N N N 4.493 21.893 10.633 10.777 0.908 -1.501 BR BUK 42 BUK C43 C43 C 0 1 N N N 1.859 22.542 17.052 6.071 -0.779 3.149 C43 BUK 43 BUK HX HX H 0 1 N N N -1.976 20.957 6.733 -6.091 -2.384 -0.904 HX BUK 44 BUK HY HY H 0 1 N N N -0.226 19.370 8.715 -5.732 -0.415 0.600 HY BUK 45 BUK HZ HZ H 0 1 N N N -0.394 20.955 7.115 -8.540 -0.575 -0.539 HZ BUK 46 BUK HOX HOX H 0 1 N N N -0.731 19.837 5.377 -5.907 -1.208 -2.862 HOX BUK 47 BUK H02 H02 H 0 1 N N N -3.030 20.409 9.079 -4.269 0.268 -1.833 H02 BUK 48 BUK H061 1H06 H 0 0 N N N -1.230 17.820 7.167 -6.496 1.200 -1.873 H061 BUK 49 BUK H062 2H06 H 0 0 N N N -2.856 18.618 7.351 -7.529 1.001 -0.438 H062 BUK 50 BUK H071 1H07 H 0 0 N N N -2.985 17.900 9.654 -5.761 2.012 0.976 H071 BUK 51 BUK H072 2H07 H 0 0 N N N -1.302 17.211 9.574 -4.728 2.212 -0.459 H072 BUK 52 BUK H081 1H08 H 0 0 N N N -2.205 15.671 7.736 -6.446 3.669 -1.494 H081 BUK 53 BUK H082 2H08 H 0 0 N N N -3.833 16.227 8.190 -7.480 3.470 -0.059 H082 BUK 54 BUK H09 H09 H 0 1 N N N -2.544 15.583 10.582 -4.954 4.410 0.787 H09 BUK 55 BUK H111 1H11 H 0 0 N N N -4.205 13.801 7.960 -4.730 6.730 1.272 H111 BUK 56 BUK H112 2H11 H 0 0 N N N -3.962 12.337 8.926 -5.827 7.832 0.634 H112 BUK 57 BUK HP2 HP2 H 0 1 N N N -2.116 13.720 11.364 -7.549 7.058 -0.714 HP2 BUK 58 BUK H13 H13 H 0 1 N N N -1.431 23.275 6.990 -9.037 -2.778 -1.784 H13 BUK 59 BUK H14 H14 H 0 1 N N N -0.465 25.005 8.520 -9.662 -4.467 -0.171 H14 BUK 60 BUK H15 H15 H 0 1 N N N 2.000 24.228 8.687 -8.935 -4.116 2.205 H15 BUK 61 BUK H17 H17 H 0 1 N N N -2.470 21.515 13.520 -1.435 -1.918 0.729 H17 BUK 62 BUK H18 H18 H 0 1 N N N -3.816 21.124 11.028 -1.886 0.039 -1.391 H18 BUK 63 BUK H21 H21 H 0 1 N N N -2.541 23.209 10.295 -2.169 -2.953 -1.921 H21 BUK 64 BUK H221 1H22 H 0 0 N N N -4.858 22.922 11.655 -2.665 -2.142 -4.251 H221 BUK 65 BUK H222 2H22 H 0 0 N N N -4.165 24.555 11.376 -3.891 -1.646 -3.060 H222 BUK 66 BUK H223 3H22 H 0 0 N N N -3.931 23.739 12.959 -2.676 -0.475 -3.626 H223 BUK 67 BUK H231 1H23 H 0 0 N N N -1.292 22.777 12.989 -0.224 -0.888 -3.049 H231 BUK 68 BUK H232 2H23 H 0 0 N N N -1.808 24.459 12.624 0.194 -2.200 -1.921 H232 BUK 69 BUK H233 3H23 H 0 0 N N N -0.650 23.618 11.538 -0.353 -2.585 -3.570 H233 BUK 70 BUK H24 H24 H 0 1 N N N -2.172 20.874 15.699 2.433 0.183 0.275 H24 BUK 71 BUK H25 H25 H 0 1 N N N -2.065 18.133 14.617 1.202 -2.338 1.090 H25 BUK 72 BUK H281 1H28 H 0 0 N N N -4.509 18.276 14.783 -0.439 -1.199 2.586 H281 BUK 73 BUK H282 2H28 H 0 0 N N N -4.378 20.026 15.280 1.225 -1.074 3.206 H282 BUK 74 BUK H311 1H31 H 0 0 N N N -5.814 18.661 17.171 -0.144 0.905 4.316 H311 BUK 75 BUK H312 2H31 H 0 0 N N N -4.625 18.193 18.415 -0.008 2.365 3.495 H312 BUK 76 BUK H34 H34 H 0 1 N N N -0.397 21.764 16.376 4.733 0.295 0.678 H34 BUK 77 BUK H35 H35 H 0 1 N N N 2.099 20.423 16.707 5.857 -2.243 1.583 H35 BUK 78 BUK H37 H37 H 0 1 N N N 4.068 20.216 15.367 6.360 1.346 0.766 H37 BUK 79 BUK H38 H38 H 0 1 N N N 5.201 20.454 13.155 8.305 2.174 -0.497 H38 BUK 80 BUK H40 H40 H 0 1 N N N 1.927 22.904 11.709 10.028 -1.728 -0.398 H40 BUK 81 BUK H41 H41 H 0 1 N N N 0.779 22.681 13.909 8.085 -2.553 0.870 H41 BUK 82 BUK H431 1H43 H 0 0 N N N 1.018 23.234 16.899 6.130 0.305 3.240 H431 BUK 83 BUK H432 2H43 H 0 0 N N N 2.798 23.036 16.762 5.211 -1.145 3.710 H432 BUK 84 BUK H433 3H43 H 0 0 N N N 1.908 22.254 18.112 6.982 -1.228 3.546 H433 BUK 85 # # 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 BUK CX CY SING N N 1 BUK CX CZ SING N N 2 BUK CX OX SING N N 3 BUK CX HX SING N N 4 BUK CY N02 SING N N 5 BUK CY C06 SING N N 6 BUK CY HY SING N N 7 BUK CZ N13 SING N N 8 BUK CZ S16 SING N N 9 BUK CZ HZ SING N N 10 BUK OX HOX SING N N 11 BUK N02 C19 SING N N 12 BUK N02 H02 SING N N 13 BUK C06 C07 SING N N 14 BUK C06 H061 SING N N 15 BUK C06 H062 SING N N 16 BUK C07 C08 SING N N 17 BUK C07 H071 SING N N 18 BUK C07 H072 SING N N 19 BUK C08 N09 SING N N 20 BUK C08 H081 SING N N 21 BUK C08 H082 SING N N 22 BUK N09 C10 SING N N 23 BUK N09 H09 SING N N 24 BUK C10 N11 SING N N 25 BUK C10 NP2 DOUB N Z 26 BUK N11 H111 SING N N 27 BUK N11 H112 SING N N 28 BUK NP2 HP2 SING N N 29 BUK N13 C14 SING N N 30 BUK N13 H13 SING N N 31 BUK C14 C15 DOUB N N 32 BUK C14 H14 SING N N 33 BUK C15 S16 SING N N 34 BUK C15 H15 SING N N 35 BUK N17 C18 SING N N 36 BUK N17 C26 SING N N 37 BUK N17 H17 SING N N 38 BUK C18 C19 SING N N 39 BUK C18 C21 SING N N 40 BUK C18 H18 SING N N 41 BUK C19 O20 DOUB N N 42 BUK C21 C22 SING N N 43 BUK C21 C23 SING N N 44 BUK C21 H21 SING N N 45 BUK C22 H221 SING N N 46 BUK C22 H222 SING N N 47 BUK C22 H223 SING N N 48 BUK C23 H231 SING N N 49 BUK C23 H232 SING N N 50 BUK C23 H233 SING N N 51 BUK N24 C25 SING N N 52 BUK N24 C32 SING N N 53 BUK N24 H24 SING N N 54 BUK C25 C26 SING N N 55 BUK C25 C28 SING N N 56 BUK C25 H25 SING N N 57 BUK C26 O27 DOUB N N 58 BUK C28 C29 SING N N 59 BUK C28 H281 SING N N 60 BUK C28 H282 SING N N 61 BUK C29 O30 DOUB N N 62 BUK C29 N31 SING N N 63 BUK N31 H311 SING N N 64 BUK N31 H312 SING N N 65 BUK C32 O33 DOUB N N 66 BUK C32 N34 SING N N 67 BUK N34 C35 SING N N 68 BUK N34 H34 SING N N 69 BUK C35 C36 SING N N 70 BUK C35 C43 SING N N 71 BUK C35 H35 SING N N 72 BUK C36 C37 SING Y N 73 BUK C36 C41 DOUB Y N 74 BUK C37 C38 DOUB Y N 75 BUK C37 H37 SING N N 76 BUK C38 C39 SING Y N 77 BUK C38 H38 SING N N 78 BUK C39 C40 DOUB Y N 79 BUK C39 BR SING N N 80 BUK C40 C41 SING Y N 81 BUK C40 H40 SING N N 82 BUK C41 H41 SING N N 83 BUK C43 H431 SING N N 84 BUK C43 H432 SING N N 85 BUK C43 H433 SING N N 86 # # 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 BUK SMILES ACDLabs 10.04 "Brc1ccc(cc1)C(NC(=O)NC(C(=O)NC(C(=O)NC(C(O)C2SC=CN2)CCCNC(=[N@H])N)C(C)C)CC(=O)N)C" BUK SMILES_CANONICAL CACTVS 3.341 "CC(C)[C@H](NC(=O)[C@H](CC(N)=O)NC(=O)N[C@H](C)c1ccc(Br)cc1)C(=O)N[C@@H](CCCNC(N)=N)[C@H](O)[C@H]2NC=CS2" BUK SMILES CACTVS 3.341 "CC(C)[CH](NC(=O)[CH](CC(N)=O)NC(=O)N[CH](C)c1ccc(Br)cc1)C(=O)N[CH](CCCNC(N)=N)[CH](O)[CH]2NC=CS2" BUK SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "[H]/N=C(/N)\NCCC[C@@H]([C@@H](C1NC=CS1)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(=O)N)NC(=O)N[C@H](C)c2ccc(cc2)Br" BUK SMILES "OpenEye OEToolkits" 1.5.0 "[H]N=C(N)NCCCC(C(C1NC=CS1)O)NC(=O)C(C(C)C)NC(=O)C(CC(=O)N)NC(=O)NC(C)c2ccc(cc2)Br" BUK InChI InChI 1.03 "InChI=1S/C27H42BrN9O5S/c1-14(2)21(24(41)35-18(5-4-10-33-26(30)31)22(39)25-32-11-12-43-25)37-23(40)19(13-20(29)38)36-27(42)34-15(3)16-6-8-17(28)9-7-16/h6-9,11-12,14-15,18-19,21-22,25,32,39H,4-5,10,13H2,1-3H3,(H2,29,38)(H,35,41)(H,37,40)(H4,30,31,33)(H2,34,36,42)/t15-,18+,19+,21+,22+,25+/m1/s1" BUK InChIKey InChI 1.03 JOESWSPHHQIQBV-JJYDKGGZSA-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 BUK "SYSTEMATIC NAME" ACDLabs 10.04 "N~2~-{[(1R)-1-(4-bromophenyl)ethyl]carbamoyl}-L-asparaginyl-N-{(1S)-4-carbamimidamido-1-[(S)-(2S)-2,3-dihydro-1,3-thiazol-2-yl(hydroxy)methyl]butyl}-L-valinamide" BUK "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-[[(1R)-1-(4-bromophenyl)ethyl]carbamoylamino]-N-[(2S)-1-[[(1S,2S)-5-carbamimidamido-1-(2,3-dihydro-1,3-thiazol-2-yl)-1-hydroxy-pentan-2-yl]amino]-3-methyl-1-oxo-butan-2-yl]butanediamide" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site BUK "Create component" 2005-06-09 RCSB BUK "Modify descriptor" 2011-06-04 RCSB BUK "Modify synonyms" 2021-03-01 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id BUK _pdbx_chem_comp_synonyms.name "N-((R)-1-(4-BROMOPHENYL)ETHYL)UREA-ASN-VAL-ARG-ALPHA-KETOTHIAZOLE" _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##