data_BEE
# 
_chem_comp.id                                    BEE 
_chem_comp.name                                  N,N-[2,5-O-[DI-4-THIOPHEN-3-YL-BENZYL]-GLUCARYL]-DI-[VALYL-AMIDO-METHANE] 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C40 H50 N4 O8 S2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "INHIBITOR BEA409" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2000-01-31 
_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                        778.977 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     BEE 
_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        1EC1 
_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 
BEE C1   C1   C 0 1 Y N N 9.699  24.197 2.021  4.205  1.163  -0.444 C1   BEE 1   
BEE C2   C2   C 0 1 Y N N 8.875  25.328 1.778  4.574  2.174  -1.312 C2   BEE 2   
BEE C3   C3   C 0 1 Y N N 7.487  25.268 2.045  5.417  1.904  -2.372 C3   BEE 3   
BEE C4   C4   C 0 1 Y N N 6.924  24.070 2.561  5.896  0.609  -2.565 C4   BEE 4   
BEE C5   C5   C 0 1 Y N N 7.745  22.949 2.802  5.521  -0.405 -1.686 C5   BEE 5   
BEE C6   C6   C 0 1 Y N N 9.132  23.013 2.531  4.682  -0.123 -0.627 C6   BEE 6   
BEE C7   C7   C 0 1 Y N N 16.129 22.256 8.486  -4.184 -1.163 -0.474 C7   BEE 7   
BEE C8   C8   C 0 1 Y N N 15.288 21.382 9.256  -4.546 -2.180 -1.339 C8   BEE 8   
BEE C9   C9   C 0 1 Y N N 15.830 20.219 9.878  -5.379 -1.916 -2.408 C9   BEE 9   
BEE C10  C10  C 0 1 Y N N 17.207 19.941 9.723  -5.857 -0.623 -2.613 C10  BEE 10  
BEE C11  C11  C 0 1 Y N N 18.050 20.817 8.950  -5.489 0.397  -1.737 C11  BEE 11  
BEE C12  C12  C 0 1 Y N N 17.507 21.976 8.330  -4.660 0.121  -0.669 C12  BEE 12  
BEE C13  C13  C 0 1 N N N 15.536 23.468 7.828  -3.274 -1.457 0.691  C13  BEE 13  
BEE O14  O14  O 0 1 N N N 14.483 23.079 6.889  -1.914 -1.277 0.289  O14  BEE 14  
BEE C15  C15  C 0 1 N N R 14.975 22.631 5.602  -1.104 -1.569 1.430  C15  BEE 15  
BEE C16  C16  C 0 1 N N R 13.966 23.037 4.534  0.180  -0.739 1.370  C16  BEE 16  
BEE C17  C17  C 0 1 N N R 13.609 24.489 4.621  -0.175 0.749  1.364  C17  BEE 17  
BEE C18  C18  C 0 1 N N R 12.244 24.775 3.933  1.108  1.580  1.430  C18  BEE 18  
BEE C19  C19  C 0 1 N N N 11.113 24.739 4.947  0.759  3.046  1.424  C19  BEE 19  
BEE O20  O20  O 0 1 N N N 10.858 23.670 5.505  1.094  3.745  0.492  O20  BEE 20  
BEE N21  N21  N 0 1 N N N 10.445 25.870 5.186  0.074  3.579  2.455  N21  BEE 21  
BEE C22  C22  C 0 1 N N S 9.313  26.008 6.147  -0.266 5.005  2.449  C22  BEE 22  
BEE C23  C23  C 0 1 N N N 9.795  26.662 7.507  -1.564 5.216  1.668  C23  BEE 23  
BEE C24  C24  C 0 1 N N N 8.622  26.845 8.539  -1.378 4.730  0.229  C24  BEE 24  
BEE C25  C25  C 0 1 N N N 10.929 25.867 8.217  -2.693 4.426  2.331  C25  BEE 25  
BEE C26  C26  C 0 1 N N N 8.328  26.939 5.471  -0.449 5.483  3.866  C26  BEE 26  
BEE O27  O27  O 0 1 N N N 8.755  27.979 4.911  -0.309 4.710  4.790  O27  BEE 27  
BEE N28  N28  N 0 1 N N N 7.006  26.555 5.529  -0.767 6.770  4.107  N28  BEE 28  
BEE C29  C29  C 0 1 N N N 6.029  27.413 4.902  -0.945 7.236  5.485  C29  BEE 29  
BEE O30  O30  O 0 1 N N N 11.983 23.776 2.875  1.928  1.281  0.298  O30  BEE 30  
BEE C31  C31  C 0 1 N N N 11.174 24.264 1.744  3.284  1.464  0.711  C31  BEE 31  
BEE O32  O32  O 0 1 N N N 14.730 25.209 4.068  -0.995 1.048  2.496  O32  BEE 32  
BEE O33  O33  O 0 1 N N N 14.492 22.689 3.206  0.989  -1.031 2.511  O33  BEE 33  
BEE C34  C34  C 0 1 N N N 15.186 21.177 5.498  -0.755 -3.035 1.436  C34  BEE 34  
BEE O35  O35  O 0 1 N N N 14.260 20.433 5.825  -1.082 -3.740 0.505  O35  BEE 35  
BEE N36  N36  N 0 1 N N N 16.378 20.755 5.039  -0.079 -3.562 2.476  N36  BEE 36  
BEE C37  C37  C 0 1 N N S 16.707 19.361 4.875  0.260  -4.987 2.482  C37  BEE 37  
BEE C38  C38  C 0 1 N N N 16.742 18.989 3.339  1.565  -5.204 1.713  C38  BEE 38  
BEE C39  C39  C 0 1 N N N 15.353 19.199 2.609  1.357  -4.838 0.242  C39  BEE 39  
BEE C40  C40  C 0 1 N N N 17.232 17.522 3.097  2.661  -4.318 2.309  C40  BEE 40  
BEE C41  C41  C 0 1 N N N 18.085 19.201 5.463  0.431  -5.457 3.904  C41  BEE 41  
BEE O42  O42  O 0 1 N N N 19.031 19.939 5.059  0.639  -4.653 4.787  O42  BEE 42  
BEE N43  N43  N 0 1 N N N 18.192 18.238 6.398  0.352  -6.771 4.193  N43  BEE 43  
BEE C44  C44  C 0 1 N N N 19.514 18.036 6.990  0.584  -7.235 5.563  C44  BEE 44  
BEE S45  S45  S 0 1 Y N N 2.832  24.222 2.669  8.545  0.355  -5.441 S45  BEE 45  
BEE C46  C46  C 0 1 Y N N 3.532  23.399 4.083  7.512  -1.101 -5.459 C46  BEE 46  
BEE C47  C47  C 0 1 Y N N 4.862  23.349 4.053  6.672  -0.869 -4.426 C47  BEE 47  
BEE C48  C48  C 0 1 Y N N 5.429  23.989 2.853  6.802  0.313  -3.702 C48  BEE 48  
BEE C49  C49  C 0 1 Y N N 4.478  24.483 2.053  7.787  1.191  -4.058 C49  BEE 49  
BEE S50  S50  S 0 1 Y N N 19.438 17.092 11.613 -8.480 -0.386 -5.514 S50  BEE 50  
BEE C51  C51  C 0 1 Y N N 19.034 18.661 10.897 -7.734 -1.214 -4.119 C51  BEE 51  
BEE C52  C52  C 0 1 Y N N 17.800 18.710 10.387 -6.752 -0.333 -3.759 C52  BEE 52  
BEE C53  C53  C 0 1 Y N N 17.080 17.433 10.550 -6.616 0.844  -4.489 C53  BEE 53  
BEE C54  C54  C 0 1 Y N N 17.814 16.511 11.169 -7.447 1.070  -5.531 C54  BEE 54  
BEE H2   H2   H 0 1 N N N 9.309  26.237 1.388  4.202  3.177  -1.162 H2   BEE 55  
BEE H3   H3   H 0 1 N N N 6.860  26.127 1.858  5.704  2.694  -3.050 H3   BEE 56  
BEE H5   H5   H 0 1 N N N 7.314  22.040 3.194  5.889  -1.410 -1.831 H5   BEE 57  
BEE H6   H6   H 0 1 N N N 9.757  22.152 2.716  4.391  -0.908 0.054  H6   BEE 58  
BEE H8   H8   H 0 1 N N N 14.237 21.608 9.365  -4.175 -3.181 -1.179 H8   BEE 59  
BEE H9   H9   H 0 1 N N N 15.199 19.562 10.458 -5.660 -2.710 -3.083 H9   BEE 60  
BEE H11  H11  H 0 1 N N N 19.101 20.592 8.841  -5.856 1.401  -1.892 H11  BEE 61  
BEE H12  H12  H 0 1 N N N 18.137 22.633 7.749  -4.375 0.910  0.010  H12  BEE 62  
BEE H131 1H13 H 0 0 N N N 16.327 23.997 7.276  -3.422 -2.487 1.017  H131 BEE 63  
BEE H132 2H13 H 0 0 N N N 15.106 24.123 8.600  -3.503 -0.779 1.512  H132 BEE 64  
BEE H15  H15  H 0 1 N N N 15.959 23.103 5.468  -1.654 -1.323 2.338  H15  BEE 65  
BEE H16  H16  H 0 1 N N N 13.033 22.480 4.707  0.729  -0.985 0.462  H16  BEE 66  
BEE H17  H17  H 0 1 N N N 13.448 24.824 5.656  -0.717 0.990  0.450  H17  BEE 67  
BEE H18  H18  H 0 1 N N N 12.293 25.779 3.485  1.650  1.339  2.345  H18  BEE 68  
BEE H21  H21  H 0 1 N N N 10.725 26.687 4.682  -0.194 3.020  3.201  H21  BEE 69  
BEE H22  H22  H 0 1 N N N 8.880  25.027 6.391  0.539  5.568  1.976  H22  BEE 70  
BEE H23  H23  H 0 1 N N N 10.185 27.643 7.199  -1.816 6.277  1.663  H23  BEE 71  
BEE H241 1H24 H 0 0 N N N 7.928  25.995 8.459  -2.303 4.881  -0.328 H241 BEE 72  
BEE H242 2H24 H 0 0 N N N 8.085  27.780 8.321  -0.573 5.294  -0.244 H242 BEE 73  
BEE H243 3H24 H 0 0 N N N 9.033  26.888 9.558  -1.125 3.670  0.233  H243 BEE 74  
BEE H251 1H25 H 0 0 N N N 10.532 24.908 8.580  -2.826 4.772  3.356  H251 BEE 75  
BEE H252 2H25 H 0 0 N N N 11.310 26.452 9.067  -3.618 4.577  1.774  H252 BEE 76  
BEE H253 3H25 H 0 0 N N N 11.747 25.679 7.506  -2.441 3.365  2.335  H253 BEE 77  
BEE H28  H28  H 0 1 N N N 6.733  25.711 5.990  -0.879 7.389  3.368  H28  BEE 78  
BEE H291 1H29 H 0 0 N N N 5.612  26.908 4.018  -1.198 8.296  5.480  H291 BEE 79  
BEE H292 2H29 H 0 0 N N N 6.510  28.353 4.595  -1.750 6.672  5.957  H292 BEE 80  
BEE H293 3H29 H 0 0 N N N 5.220  27.631 5.615  -0.020 7.085  6.041  H293 BEE 81  
BEE H311 1H31 H 0 0 N N N 11.436 25.319 1.574  3.430  2.495  1.032  H311 BEE 82  
BEE H312 2H31 H 0 0 N N N 11.392 23.640 0.865  3.506  0.790  1.538  H312 BEE 83  
BEE H32  H32  H 0 1 N N N 14.580 25.367 3.143  -0.479 0.822  3.282  H32  BEE 84  
BEE H33  H33  H 0 1 N N N 13.773 22.614 2.590  0.467  -0.799 3.291  H33  BEE 85  
BEE H36  H36  H 0 1 N N N 17.067 21.439 4.801  0.182  -2.998 3.221  H36  BEE 86  
BEE H37  H37  H 0 1 N N N 15.968 18.709 5.363  -0.540 -5.553 2.006  H37  BEE 87  
BEE H38  H38  H 0 1 N N N 17.466 19.691 2.900  1.863  -6.250 1.789  H38  BEE 88  
BEE H391 1H39 H 0 0 N N N 15.167 18.357 1.926  1.179  -3.767 0.156  H391 BEE 89  
BEE H392 2H39 H 0 0 N N N 15.378 20.138 2.036  2.247  -5.106 -0.328 H392 BEE 90  
BEE H393 3H39 H 0 0 N N N 14.548 19.248 3.358  0.498  -5.383 -0.149 H393 BEE 91  
BEE H401 1H40 H 0 0 N N N 16.493 16.817 3.506  2.809  -4.578 3.357  H401 BEE 92  
BEE H402 2H40 H 0 0 N N N 18.200 17.372 3.598  3.591  -4.472 1.761  H402 BEE 93  
BEE H403 3H40 H 0 0 N N N 17.347 17.347 2.017  2.364  -3.272 2.233  H403 BEE 94  
BEE H43  H43  H 0 1 N N N 17.405 17.687 6.675  0.141  -7.410 3.494  H43  BEE 95  
BEE H441 1H44 H 0 0 N N N 19.520 17.096 7.561  1.591  -6.957 5.875  H441 BEE 96  
BEE H442 2H44 H 0 0 N N N 19.747 18.875 7.662  -0.144 -6.774 6.231  H442 BEE 97  
BEE H443 3H44 H 0 0 N N N 20.270 17.985 6.192  0.478  -8.319 5.603  H443 BEE 98  
BEE H46  H46  H 0 1 N N N 2.939  22.983 4.884  7.552  -1.952 -6.122 H46  BEE 99  
BEE H47  H47  H 0 1 N N N 5.461  22.889 4.825  5.906  -1.586 -4.171 H47  BEE 100 
BEE H49  H49  H 0 1 N N N 4.690  24.991 1.124  8.040  2.144  -3.618 H49  BEE 101 
BEE H51  H51  H 0 1 N N N 19.718 19.496 10.875 -7.991 -2.164 -3.676 H51  BEE 102 
BEE H53  H53  H 0 1 N N N 16.070 17.265 10.206 -5.852 1.562  -4.232 H53  BEE 103 
BEE H54  H54  H 0 1 N N N 17.461 15.513 11.380 -7.481 1.917  -6.201 H54  BEE 104 
# 
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 
BEE C1  C2   DOUB Y N 1   
BEE C1  C6   SING Y N 2   
BEE C1  C31  SING N N 3   
BEE C2  C3   SING Y N 4   
BEE C2  H2   SING N N 5   
BEE C3  C4   DOUB Y N 6   
BEE C3  H3   SING N N 7   
BEE C4  C5   SING Y N 8   
BEE C4  C48  SING N N 9   
BEE C5  C6   DOUB Y N 10  
BEE C5  H5   SING N N 11  
BEE C6  H6   SING N N 12  
BEE C7  C8   DOUB Y N 13  
BEE C7  C12  SING Y N 14  
BEE C7  C13  SING N N 15  
BEE C8  C9   SING Y N 16  
BEE C8  H8   SING N N 17  
BEE C9  C10  DOUB Y N 18  
BEE C9  H9   SING N N 19  
BEE C10 C11  SING Y N 20  
BEE C10 C52  SING N N 21  
BEE C11 C12  DOUB Y N 22  
BEE C11 H11  SING N N 23  
BEE C12 H12  SING N N 24  
BEE C13 O14  SING N N 25  
BEE C13 H131 SING N N 26  
BEE C13 H132 SING N N 27  
BEE O14 C15  SING N N 28  
BEE C15 C16  SING N N 29  
BEE C15 C34  SING N N 30  
BEE C15 H15  SING N N 31  
BEE C16 C17  SING N N 32  
BEE C16 O33  SING N N 33  
BEE C16 H16  SING N N 34  
BEE C17 C18  SING N N 35  
BEE C17 O32  SING N N 36  
BEE C17 H17  SING N N 37  
BEE C18 C19  SING N N 38  
BEE C18 O30  SING N N 39  
BEE C18 H18  SING N N 40  
BEE C19 O20  DOUB N N 41  
BEE C19 N21  SING N N 42  
BEE N21 C22  SING N N 43  
BEE N21 H21  SING N N 44  
BEE C22 C23  SING N N 45  
BEE C22 C26  SING N N 46  
BEE C22 H22  SING N N 47  
BEE C23 C24  SING N N 48  
BEE C23 C25  SING N N 49  
BEE C23 H23  SING N N 50  
BEE C24 H241 SING N N 51  
BEE C24 H242 SING N N 52  
BEE C24 H243 SING N N 53  
BEE C25 H251 SING N N 54  
BEE C25 H252 SING N N 55  
BEE C25 H253 SING N N 56  
BEE C26 O27  DOUB N N 57  
BEE C26 N28  SING N N 58  
BEE N28 C29  SING N N 59  
BEE N28 H28  SING N N 60  
BEE C29 H291 SING N N 61  
BEE C29 H292 SING N N 62  
BEE C29 H293 SING N N 63  
BEE O30 C31  SING N N 64  
BEE C31 H311 SING N N 65  
BEE C31 H312 SING N N 66  
BEE O32 H32  SING N N 67  
BEE O33 H33  SING N N 68  
BEE C34 O35  DOUB N N 69  
BEE C34 N36  SING N N 70  
BEE N36 C37  SING N N 71  
BEE N36 H36  SING N N 72  
BEE C37 C38  SING N N 73  
BEE C37 C41  SING N N 74  
BEE C37 H37  SING N N 75  
BEE C38 C39  SING N N 76  
BEE C38 C40  SING N N 77  
BEE C38 H38  SING N N 78  
BEE C39 H391 SING N N 79  
BEE C39 H392 SING N N 80  
BEE C39 H393 SING N N 81  
BEE C40 H401 SING N N 82  
BEE C40 H402 SING N N 83  
BEE C40 H403 SING N N 84  
BEE C41 O42  DOUB N N 85  
BEE C41 N43  SING N N 86  
BEE N43 C44  SING N N 87  
BEE N43 H43  SING N N 88  
BEE C44 H441 SING N N 89  
BEE C44 H442 SING N N 90  
BEE C44 H443 SING N N 91  
BEE S45 C46  SING Y N 92  
BEE S45 C49  SING Y N 93  
BEE C46 C47  DOUB Y N 94  
BEE C46 H46  SING N N 95  
BEE C47 C48  SING Y N 96  
BEE C47 H47  SING N N 97  
BEE C48 C49  DOUB Y N 98  
BEE C49 H49  SING N N 99  
BEE S50 C51  SING Y N 100 
BEE S50 C54  SING Y N 101 
BEE C51 C52  DOUB Y N 102 
BEE C51 H51  SING N N 103 
BEE C52 C53  SING Y N 104 
BEE C53 C54  DOUB Y N 105 
BEE C53 H53  SING N N 106 
BEE C54 H54  SING N N 107 
# 
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 
BEE SMILES           ACDLabs              10.04 O=C(NC)C(NC(=O)C(OCc2ccc(c1ccsc1)cc2)C(O)C(O)C(OCc4ccc(c3ccsc3)cc4)C(=O)NC(C(=O)NC)C(C)C)C(C)C 
BEE InChI            InChI                1.02b 
;InChI=1/C40H50N4O8S2/c1-23(2)31(37(47)41-5)43-39(49)35(51-19-25-7-11-27(12-8-25)29-15-17-53-21-29)33(45)34(46)36(40(50)44-32(24(3)4)38(48)42-6)52-20-26-9-13-28(14-10-26)30-16-18-54-22-30/h7-18,21-24,31-36,45-46H,19-20H2,1-6H3,(H,41,47)(H,42,48)(H,43,49)(H,44,50)/t31-,32-,33+,34+,35+,36+/m0/s1/f/h41-44H
;
BEE InChIKey         InChI                1.02b AJZAPEZJWWQJHC-MTKKIVFADM 
BEE SMILES_CANONICAL CACTVS               3.341 CNC(=O)[C@@H](NC(=O)[C@H](OCc1ccc(cc1)c2cscc2)[C@H](O)[C@@H](O)[C@@H](OCc3ccc(cc3)c4cscc4)C(=O)N[C@@H](C(C)C)C(=O)NC)C(C)C 
BEE SMILES           CACTVS               3.341 CNC(=O)[CH](NC(=O)[CH](OCc1ccc(cc1)c2cscc2)[CH](O)[CH](O)[CH](OCc3ccc(cc3)c4cscc4)C(=O)N[CH](C(C)C)C(=O)NC)C(C)C 
BEE SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(C)[C@@H](C(=O)NC)NC(=O)[C@@H]([C@@H]([C@H]([C@H](C(=O)N[C@@H](C(C)C)C(=O)NC)OCc1ccc(cc1)c2ccsc2)O)O)OCc3ccc(cc3)c4ccsc4 
BEE SMILES           "OpenEye OEToolkits" 1.5.0 CC(C)C(C(=O)NC)NC(=O)C(C(C(C(C(=O)NC(C(C)C)C(=O)NC)OCc1ccc(cc1)c2ccsc2)O)O)OCc3ccc(cc3)c4ccsc4 
# 
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 
BEE "SYSTEMATIC NAME" ACDLabs              10.04 
;(2R,3R,4R,5R)-3,4-dihydroxy-N,N'-bis[(1S)-2-methyl-1-(methylcarbamoyl)propyl]-2,5-bis[(4-thiophen-3-ylbenzyl)oxy]hexanediamide (non-preferred name)
;
BEE "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2R,3R,4R,5R)-3,4-dihydroxy-N,N'-bis[(2S)-3-methyl-1-methylamino-1-oxo-butan-2-yl]-2,5-bis[(4-thiophen-3-ylphenyl)methoxy]hexanediamide"             
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