data_BE6
# 
_chem_comp.id                                    BE6 
_chem_comp.name                                  "(2R,3R,4R,5R)-2,5-BIS[(2,5-DIFLUOROBENZYL)OXY]-3,4-DIHYDROXY-N,N'-BIS[(1S,2R)-2-HYDROXY-2,3-DIHYDRO-1H-INDEN-1-YL]HEXANEDIAMIDE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C38 H36 F4 N2 O8" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "HIV-1 INHIBITOR" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-08-10 
_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                        724.695 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     BE6 
_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        1W5Y 
_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 
BE6 C01  C01  C 0 1 Y N N 16.735 22.420 8.878  -4.113 -1.375 -1.129 C01  BE6 1  
BE6 C02  C02  C 0 1 Y N N 18.129 22.504 8.448  -3.410 -2.564 -1.176 C02  BE6 2  
BE6 C03  C03  C 0 1 Y N N 19.077 21.445 8.678  -3.945 -3.659 -1.832 C03  BE6 3  
BE6 C04  C04  C 0 1 Y N N 18.671 20.226 9.366  -5.184 -3.564 -2.441 C04  BE6 4  
BE6 C05  C05  C 0 1 Y N N 17.279 20.100 9.814  -5.887 -2.376 -2.395 C05  BE6 5  
BE6 C06  C06  C 0 1 Y N N 16.336 21.173 9.572  -5.355 -1.282 -1.735 C06  BE6 6  
BE6 C07  C07  C 0 1 Y N N 10.089 24.113 2.255  4.122  -1.362 1.119  C07  BE6 7  
BE6 C08  C08  C 0 1 Y N N 8.964  23.265 2.651  5.363  -1.267 1.724  C08  BE6 8  
BE6 C09  C09  C 0 1 Y N N 7.591  23.829 2.667  5.902  -2.364 2.375  C09  BE6 9  
BE6 C10  C10  C 0 1 Y N N 7.377  25.246 2.281  5.205  -3.557 2.411  C10  BE6 10 
BE6 C11  C11  C 0 1 Y N N 8.544  26.066 1.889  3.966  -3.654 1.800  C11  BE6 11 
BE6 C12  C12  C 0 1 Y N N 9.853  25.496 1.883  3.425  -2.555 1.154  C12  BE6 12 
BE6 C13  C13  C 0 1 N N N 11.526 23.625 2.223  3.534  -0.167 0.415  C13  BE6 13 
BE6 O14  O14  O 0 1 N N N 12.090 23.309 3.524  2.260  -0.515 -0.130 O14  BE6 14 
BE6 C15  C15  C 0 1 N N R 12.132 24.402 4.579  1.756  0.653  -0.781 C15  BE6 15 
BE6 C16  C16  C 0 1 N N R 13.162 24.129 5.664  0.227  0.648  -0.726 C16  BE6 16 
BE6 C17  C17  C 0 1 N N R 14.472 23.789 5.058  -0.230 0.640  0.733  C17  BE6 17 
BE6 C18  C18  C 0 1 N N R 15.360 23.057 6.141  -1.759 0.636  0.788  C18  BE6 18 
BE6 C19  C19  C 0 1 N N N 15.424 21.557 5.940  -2.210 0.628  2.226  C19  BE6 19 
BE6 O20  O20  O 0 1 N N N 14.415 20.867 6.160  -2.890 -0.284 2.644  O20  BE6 20 
BE6 N21  N21  N 0 1 N N N 16.595 20.959 5.545  -1.857 1.636  3.048  N21  BE6 21 
BE6 O22  O22  O 0 1 N N N 14.853 23.343 7.502  -2.256 -0.528 0.127  O22  BE6 22 
BE6 C23  C23  C 0 1 N N N 15.824 23.621 8.553  -3.532 -0.183 -0.415 C23  BE6 23 
BE6 O24  O24  O 0 1 N N N 15.076 25.032 4.617  0.266  1.806  1.394  O24  BE6 24 
BE6 O25  O25  O 0 1 N N N 13.382 25.287 6.546  -0.276 1.817  -1.377 O25  BE6 25 
BE6 C26  C26  C 0 1 N N N 10.899 24.482 5.432  2.207  0.661  -2.219 C26  BE6 26 
BE6 O27  O27  O 0 1 N N N 10.505 23.443 6.010  2.892  -0.244 -2.644 O27  BE6 27 
BE6 N28  N28  N 0 1 N N N 10.262 25.700 5.536  1.849  1.674  -3.032 N28  BE6 28 
BE6 C29  C29  C 0 1 N N S 9.061  25.934 6.319  2.287  1.682  -4.430 C29  BE6 29 
BE6 C30  C30  C 0 1 Y N N 9.396  26.681 7.558  1.253  1.002  -5.310 C30  BE6 30 
BE6 C31  C31  C 0 1 Y N N 8.317  27.581 7.919  1.057  1.743  -6.461 C31  BE6 31 
BE6 C32  C32  C 0 1 Y N N 10.584 26.583 8.396  0.542  -0.170 -5.117 C32  BE6 32 
BE6 C33  C33  C 0 1 Y N N 10.672 27.412 9.617  -0.359 -0.601 -6.069 C33  BE6 33 
BE6 C34  C34  C 0 1 Y N N 9.575  28.305 9.957  -0.555 0.139  -7.220 C34  BE6 34 
BE6 C35  C35  C 0 1 N N R 7.943  26.837 5.718  2.373  3.128  -4.962 C35  BE6 35 
BE6 O36  O36  O 0 1 N N N 8.562  27.842 4.885  1.469  3.982  -4.258 O36  BE6 36 
BE6 C37  C37  C 0 1 Y N N 8.389  28.405 9.120  0.152  1.309  -7.414 C37  BE6 37 
BE6 C38  C38  C 0 1 N N N 7.228  27.513 6.914  1.943  2.970  -6.435 C38  BE6 38 
BE6 C39  C39  C 0 1 N N S 16.712 19.531 5.363  -2.295 1.629  4.446  C39  BE6 39 
BE6 C40  C40  C 0 1 Y N N 16.606 19.081 3.908  -1.246 0.978  5.322  C40  BE6 40 
BE6 C41  C41  C 0 1 Y N N 17.537 18.012 3.653  -1.071 1.727  6.473  C41  BE6 41 
BE6 C42  C42  C 0 1 Y N N 15.748 19.565 2.840  -0.501 -0.171 5.129  C42  BE6 42 
BE6 C43  C43  C 0 1 Y N N 15.846 18.948 1.498  0.413  -0.575 6.081  C43  BE6 43 
BE6 C44  C44  C 0 1 Y N N 16.797 17.871 1.277  0.587  0.170  7.231  C44  BE6 44 
BE6 C45  C45  C 0 1 N N R 18.076 18.951 5.777  -2.427 3.073  4.974  C45  BE6 45 
BE6 O46  O46  O 0 1 N N N 19.097 19.950 5.499  -1.552 3.954  4.267  O46  BE6 46 
BE6 C47  C47  C 0 1 Y N N 17.655 17.384 2.337  -0.153 1.319  7.426  C47  BE6 47 
BE6 C48  C48  C 0 1 N N N 18.299 17.709 4.912  -1.992 2.928  6.448  C48  BE6 48 
BE6 F49  F49  F 0 1 N N N 8.474  27.399 1.512  3.285  -4.820 1.835  F49  BE6 49 
BE6 F50  F50  F 0 1 N N N 20.278 21.561 8.282  -3.257 -4.821 -1.877 F50  BE6 50 
BE6 F51  F51  F 0 1 N N N 14.876 21.072 10.016 -6.043 -0.119 -1.689 F51  BE6 51 
BE6 F52  F52  F 0 1 N N N 9.156  22.122 2.965  6.044  -0.101 1.690  F52  BE6 52 
BE6 H02  H02  H 0 1 N N N 18.469 23.415 7.927  -2.443 -2.638 -0.701 H02  BE6 53 
BE6 H04  H04  H 0 1 N N N 19.396 19.414 9.547  -5.602 -4.419 -2.953 H04  BE6 54 
BE6 H05  H05  H 0 1 N N N 16.950 19.186 10.336 -6.854 -2.302 -2.871 H05  BE6 55 
BE6 H09  H09  H 0 1 N N N 6.735  23.199 2.964  6.868  -2.289 2.852  H09  BE6 56 
BE6 H10  H10  H 0 1 N N N 6.363  25.681 2.286  5.627  -4.414 2.915  H10  BE6 57 
BE6 H12  H12  H 0 1 N N N 10.710 26.125 1.587  2.459  -2.631 0.678  H12  BE6 58 
BE6 H131 1H13 H 0 0 N N N 12.172 24.361 1.690  4.200  0.145  -0.388 H131 BE6 59 
BE6 H132 2H13 H 0 0 N N N 11.622 22.751 1.537  3.414  0.650  1.126  H132 BE6 60 
BE6 H15  H15  H 0 1 N N N 12.332 25.389 4.101  2.135  1.542  -0.277 H15  BE6 61 
BE6 H16  H16  H 0 1 N N N 12.816 23.267 6.281  -0.151 -0.240 -1.230 H16  BE6 62 
BE6 H17  H17  H 0 1 N N N 14.317 23.116 4.183  0.153  -0.250 1.230  H17  BE6 63 
BE6 H18  H18  H 0 1 N N N 16.397 23.460 6.067  -2.143 1.527  0.292  H18  BE6 64 
BE6 H21  H21  H 0 1 N N N 17.412 21.545 5.374  -1.313 2.367  2.714  H21  BE6 65 
BE6 H231 1H23 H 0 0 N N N 16.431 24.522 8.302  -4.200 0.118  0.391  H231 BE6 66 
BE6 H232 2H23 H 0 0 N N N 15.315 23.992 9.473  -3.416 0.641  -1.118 H232 BE6 67 
BE6 H24  H24  H 0 1 N N N 15.915 24.814 4.229  -0.095 2.569  0.925  H24  BE6 68 
BE6 H25  H25  H 0 1 N N N 14.025 25.117 7.224  0.082  2.578  -0.901 H25  BE6 69 
BE6 H28  H28  H 0 1 N N N 10.661 26.490 5.029  1.301  2.398  -2.692 H28  BE6 70 
BE6 H29  H29  H 0 1 N N N 8.617  24.951 6.600  3.252  1.183  -4.526 H29  BE6 71 
BE6 H32  H32  H 0 1 N N N 11.406 25.900 8.123  0.695  -0.750 -4.218 H32  BE6 72 
BE6 H33  H33  H 0 1 N N N 11.563 27.354 10.265 -0.912 -1.516 -5.915 H33  BE6 73 
BE6 H34  H34  H 0 1 N N N 9.644  28.920 10.870 -1.261 -0.196 -7.965 H34  BE6 74 
BE6 H35  H35  H 0 1 N N N 7.223  26.226 5.125  3.393  3.506  -4.894 H35  BE6 75 
BE6 H36  H36  H 0 1 N N N 7.880  28.393 4.518  1.538  4.857  -4.663 H36  BE6 76 
BE6 H37  H37  H 0 1 N N N 7.565  29.087 9.387  -0.001 1.887  -8.313 H37  BE6 77 
BE6 H381 1H38 H 0 0 N N N 6.297  27.005 7.258  1.384  3.847  -6.762 H381 BE6 78 
BE6 H382 2H38 H 0 0 N N N 6.735  28.486 6.683  2.816  2.819  -7.070 H382 BE6 79 
BE6 H39  H39  H 0 1 N N N 15.913 19.027 5.954  -3.246 1.104  4.541  H39  BE6 80 
BE6 H42  H42  H 0 1 N N N 15.032 20.383 3.027  -0.637 -0.755 4.231  H42  BE6 81 
BE6 H43  H43  H 0 1 N N N 15.204 19.302 0.674  0.991  -1.474 5.927  H43  BE6 82 
BE6 H44  H44  H 0 1 N N N 16.867 17.413 0.276  1.302  -0.144 7.977  H44  BE6 83 
BE6 H45  H45  H 0 1 N N N 18.076 18.681 6.859  -3.458 3.418  4.907  H45  BE6 84 
BE6 H46  H46  H 0 1 N N N 19.939 19.592 5.755  -1.680 4.836  4.641  H46  BE6 85 
BE6 H47  H47  H 0 1 N N N 18.374 16.567 2.158  -0.016 1.902  8.325  H47  BE6 86 
BE6 H481 1H48 H 0 0 N N N 18.015 16.749 5.403  -1.458 3.821  6.775  H481 BE6 87 
BE6 H482 2H48 H 0 0 N N N 19.371 17.446 4.750  -2.860 2.752  7.083  H482 BE6 88 
# 
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 
BE6 C01 C02  DOUB Y N 1  
BE6 C01 C06  SING Y N 2  
BE6 C01 C23  SING N N 3  
BE6 C02 C03  SING Y N 4  
BE6 C02 H02  SING N N 5  
BE6 C03 C04  DOUB Y N 6  
BE6 C03 F50  SING N N 7  
BE6 C04 C05  SING Y N 8  
BE6 C04 H04  SING N N 9  
BE6 C05 C06  DOUB Y N 10 
BE6 C05 H05  SING N N 11 
BE6 C06 F51  SING N N 12 
BE6 C07 C08  DOUB Y N 13 
BE6 C07 C12  SING Y N 14 
BE6 C07 C13  SING N N 15 
BE6 C08 C09  SING Y N 16 
BE6 C08 F52  SING N N 17 
BE6 C09 C10  DOUB Y N 18 
BE6 C09 H09  SING N N 19 
BE6 C10 C11  SING Y N 20 
BE6 C10 H10  SING N N 21 
BE6 C11 C12  DOUB Y N 22 
BE6 C11 F49  SING N N 23 
BE6 C12 H12  SING N N 24 
BE6 C13 O14  SING N N 25 
BE6 C13 H131 SING N N 26 
BE6 C13 H132 SING N N 27 
BE6 O14 C15  SING N N 28 
BE6 C15 C16  SING N N 29 
BE6 C15 C26  SING N N 30 
BE6 C15 H15  SING N N 31 
BE6 C16 C17  SING N N 32 
BE6 C16 O25  SING N N 33 
BE6 C16 H16  SING N N 34 
BE6 C17 C18  SING N N 35 
BE6 C17 O24  SING N N 36 
BE6 C17 H17  SING N N 37 
BE6 C18 C19  SING N N 38 
BE6 C18 O22  SING N N 39 
BE6 C18 H18  SING N N 40 
BE6 C19 O20  DOUB N N 41 
BE6 C19 N21  SING N N 42 
BE6 N21 C39  SING N N 43 
BE6 N21 H21  SING N N 44 
BE6 O22 C23  SING N N 45 
BE6 C23 H231 SING N N 46 
BE6 C23 H232 SING N N 47 
BE6 O24 H24  SING N N 48 
BE6 O25 H25  SING N N 49 
BE6 C26 O27  DOUB N N 50 
BE6 C26 N28  SING N N 51 
BE6 N28 C29  SING N N 52 
BE6 N28 H28  SING N N 53 
BE6 C29 C30  SING N N 54 
BE6 C29 C35  SING N N 55 
BE6 C29 H29  SING N N 56 
BE6 C30 C31  DOUB Y N 57 
BE6 C30 C32  SING Y N 58 
BE6 C31 C37  SING Y N 59 
BE6 C31 C38  SING N N 60 
BE6 C32 C33  DOUB Y N 61 
BE6 C32 H32  SING N N 62 
BE6 C33 C34  SING Y N 63 
BE6 C33 H33  SING N N 64 
BE6 C34 C37  DOUB Y N 65 
BE6 C34 H34  SING N N 66 
BE6 C35 O36  SING N N 67 
BE6 C35 C38  SING N N 68 
BE6 C35 H35  SING N N 69 
BE6 O36 H36  SING N N 70 
BE6 C37 H37  SING N N 71 
BE6 C38 H381 SING N N 72 
BE6 C38 H382 SING N N 73 
BE6 C39 C40  SING N N 74 
BE6 C39 C45  SING N N 75 
BE6 C39 H39  SING N N 76 
BE6 C40 C41  DOUB Y N 77 
BE6 C40 C42  SING Y N 78 
BE6 C41 C47  SING Y N 79 
BE6 C41 C48  SING N N 80 
BE6 C42 C43  DOUB Y N 81 
BE6 C42 H42  SING N N 82 
BE6 C43 C44  SING Y N 83 
BE6 C43 H43  SING N N 84 
BE6 C44 C47  DOUB Y N 85 
BE6 C44 H44  SING N N 86 
BE6 C45 O46  SING N N 87 
BE6 C45 C48  SING N N 88 
BE6 C45 H45  SING N N 89 
BE6 O46 H46  SING N N 90 
BE6 C47 H47  SING N N 91 
BE6 C48 H481 SING N N 92 
BE6 C48 H482 SING N N 93 
# 
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 
BE6 SMILES           ACDLabs              10.04 Fc1cc(c(F)cc1)COC(C(=O)NC3c2ccccc2CC3O)C(O)C(O)C(OCc4cc(F)ccc4F)C(=O)NC6c5ccccc5CC6O 
BE6 InChI            InChI                1.02b 
;InChI=1/C38H36F4N2O8/c39-23-9-11-27(41)21(13-23)17-51-35(37(49)43-31-25-7-3-1-5-19(25)15-29(31)45)33(47)34(48)36(52-18-22-14-24(40)10-12-28(22)42)38(50)44-32-26-8-4-2-6-20(26)16-30(32)46/h1-14,29-36,45-48H,15-18H2,(H,43,49)(H,44,50)/t29-,30-,31+,32+,33-,34-,35-,36-/m1/s1/f/h43-44H
;
BE6 InChIKey         InChI                1.02b MHRYDJWKKUNWJY-SBWOTXQCDB 
BE6 SMILES_CANONICAL CACTVS               3.341 O[C@@H]1Cc2ccccc2[C@@H]1NC(=O)[C@H](OCc3cc(F)ccc3F)[C@H](O)[C@@H](O)[C@@H](OCc4cc(F)ccc4F)C(=O)N[C@@H]5[C@H](O)Cc6ccccc56 
BE6 SMILES           CACTVS               3.341 O[CH]1Cc2ccccc2[CH]1NC(=O)[CH](OCc3cc(F)ccc3F)[CH](O)[CH](O)[CH](OCc4cc(F)ccc4F)C(=O)N[CH]5[CH](O)Cc6ccccc56 
BE6 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)C[C@H]([C@H]2NC(=O)[C@@H]([C@@H]([C@H]([C@H](C(=O)N[C@H]3c4ccccc4C[C@H]3O)OCc5cc(ccc5F)F)O)O)OCc6cc(ccc6F)F)O 
BE6 SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)CC(C2NC(=O)C(C(C(C(C(=O)NC3c4ccccc4CC3O)OCc5cc(ccc5F)F)O)O)OCc6cc(ccc6F)F)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 
BE6 "SYSTEMATIC NAME" ACDLabs              10.04 
;(2R,3R,4R,5R)-2,5-bis[(2,5-difluorobenzyl)oxy]-3,4-dihydroxy-N,N'-bis[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]hexanediamide (non-preferred name)
;
BE6 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2R,3R,4R,5R)-2,5-bis[(2,5-difluorophenyl)methoxy]-3,4-dihydroxy-N,N'-bis[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]hexanediamide"                  
# 
