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                    2008-10-14 
_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 InChI            InChI                1.02b 
;InChI=1/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/f/h30,33-37H,29,31H2/b30-26-
;
BUK InChIKey         InChI                1.02b JOESWSPHHQIQBV-VTXIAJFZDK 
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 
# 
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 
# 
