data_BE5
# 
_chem_comp.id                                    BE5 
_chem_comp.name                                  "(2R,3R,4R,5R)-2,5-BIS[(2,3-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                     BE5 
_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        1W5X 
_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 
BE5 C01  C01  C 0 1 Y N N 16.567 21.959 8.756  3.793  1.499  -1.953 C01  BE5 1  
BE5 C02  C02  C 0 1 Y N N 18.013 21.787 8.523  3.096  2.689  -1.853 C02  BE5 2  
BE5 C03  C03  C 0 1 Y N N 18.711 20.561 8.861  3.482  3.783  -2.604 C03  BE5 3  
BE5 C04  C04  C 0 1 Y N N 17.983 19.429 9.455  4.567  3.691  -3.456 C04  BE5 4  
BE5 C05  C05  C 0 1 Y N N 16.530 19.562 9.702  5.267  2.502  -3.558 C05  BE5 5  
BE5 C06  C06  C 0 1 Y N N 15.843 20.800 9.359  4.883  1.405  -2.800 C06  BE5 6  
BE5 C07  C07  C 0 1 Y N N 9.811  23.856 2.186  -3.803 1.491  1.944  C07  BE5 7  
BE5 C08  C08  C 0 1 Y N N 8.770  22.928 2.668  -4.892 1.397  2.792  C08  BE5 8  
BE5 C09  C09  C 0 1 Y N N 7.342  23.366 2.704  -5.283 2.497  3.541  C09  BE5 9  
BE5 C10  C10  C 0 1 Y N N 6.981  24.748 2.245  -4.589 3.689  3.431  C10  BE5 10 
BE5 C11  C11  C 0 1 Y N N 8.069  25.653 1.764  -3.505 3.782  2.578  C11  BE5 11 
BE5 C12  C12  C 0 1 Y N N 9.435  25.199 1.746  -3.112 2.684  1.835  C12  BE5 12 
BE5 C13  C13  C 0 1 N N N 11.290 23.491 2.127  -3.373 0.296  1.133  C13  BE5 13 
BE5 O14  O14  O 0 1 N N N 11.760 23.061 3.446  -2.238 0.643  0.337  O14  BE5 14 
BE5 C15  C15  C 0 1 N N R 11.936 24.080 4.576  -1.880 -0.525 -0.403 C15  BE5 15 
BE5 C16  C16  C 0 1 N N R 12.997 23.686 5.566  -0.373 -0.521 -0.664 C16  BE5 16 
BE5 C17  C17  C 0 1 N N R 14.282 23.465 4.915  0.375  -0.514 0.669  C17  BE5 17 
BE5 C18  C18  C 0 1 N N R 15.229 22.727 5.959  1.883  -0.511 0.408  C18  BE5 18 
BE5 C19  C19  C 0 1 N N N 15.186 21.217 5.792  2.620  -0.504 1.723  C19  BE5 19 
BE5 O20  O20  O 0 1 N N N 14.128 20.572 6.003  3.372  0.408  1.991  O20  BE5 20 
BE5 N21  N21  N 0 1 N N N 16.340 20.585 5.428  2.444  -1.512 2.600  N21  BE5 21 
BE5 O22  O22  O 0 1 N N N 14.886 23.062 7.373  2.234  0.653  -0.340 O22  BE5 22 
BE5 C23  C23  C 0 1 N N N 15.946 23.304 8.351  3.370  0.307  -1.134 C23  BE5 23 
BE5 O24  O24  O 0 1 N N N 14.843 24.745 4.519  0.024  -1.679 1.419  O24  BE5 24 
BE5 O25  O25  O 0 1 N N N 13.137 24.798 6.543  -0.015 -1.690 -1.405 O25  BE5 25 
BE5 C26  C26  C 0 1 N N N 10.697 24.217 5.367  -2.618 -0.532 -1.717 C26  BE5 26 
BE5 O27  O27  O 0 1 N N N 10.267 23.236 6.026  -3.375 0.374  -1.992 O27  BE5 27 
BE5 N28  N28  N 0 1 N N N 10.049 25.410 5.370  -2.435 -1.545 -2.587 N28  BE5 28 
BE5 C29  C29  C 0 1 N N S 8.831  25.605 6.129  -3.152 -1.552 -3.864 C29  BE5 29 
BE5 C30  C30  C 0 1 Y N N 9.143  26.303 7.414  -2.321 -0.873 -4.939 C30  BE5 30 
BE5 C31  C31  C 0 1 Y N N 8.009  27.145 7.803  -2.367 -1.613 -6.105 C31  BE5 31 
BE5 C32  C32  C 0 1 Y N N 10.361 26.247 8.258  -1.585 0.299  -4.896 C32  BE5 32 
BE5 C33  C33  C 0 1 Y N N 10.414 27.064 9.512  -0.898 0.730  -6.013 C33  BE5 33 
BE5 C34  C34  C 0 1 Y N N 9.256  27.900 9.874  -0.944 -0.010 -7.180 C34  BE5 34 
BE5 C35  C35  C 0 1 N N R 7.766  26.571 5.544  -3.346 -2.998 -4.367 C35  BE5 35 
BE5 O36  O36  O 0 1 N N N 8.483  27.646 4.889  -2.317 -3.853 -3.865 O36  BE5 36 
BE5 C37  C37  C 0 1 Y N N 8.044  27.954 9.034  -1.677 -1.180 -7.225 C37  BE5 37 
BE5 C38  C38  C 0 1 N N N 6.940  27.011 6.789  -3.229 -2.840 -5.898 C38  BE5 38 
BE5 C39  C39  C 0 1 N N S 16.442 19.156 5.250  3.161  -1.505 3.877  C39  BE5 39 
BE5 C40  C40  C 0 1 Y N N 16.360 18.758 3.782  2.315  -0.854 4.951  C40  BE5 40 
BE5 C41  C41  C 0 1 Y N N 17.305 17.688 3.510  2.379  -1.603 6.112  C41  BE5 41 
BE5 C42  C42  C 0 1 Y N N 15.512 19.292 2.705  1.547  0.295  4.915  C42  BE5 42 
BE5 C43  C43  C 0 1 Y N N 15.636 18.719 1.330  0.848  0.700  6.035  C43  BE5 43 
BE5 C44  C44  C 0 1 Y N N 16.601 17.640 1.096  0.914  -0.046 7.197  C44  BE5 44 
BE5 C45  C45  C 0 1 N N R 17.846 18.620 5.638  3.397  -2.950 4.366  C45  BE5 45 
BE5 O46  O46  O 0 1 N N N 18.812 19.662 5.343  2.394  -3.830 3.854  O46  BE5 46 
BE5 C47  C47  C 0 1 Y N N 17.449 17.103 2.162  1.678  -1.195 7.235  C47  BE5 47 
BE5 C48  C48  C 0 1 N N N 18.023 17.353 4.783  3.275  -2.805 5.898  C48  BE5 48 
BE5 F49  F49  F 0 1 N N N 6.315  22.450 3.184  -6.343 2.405  4.374  F49  BE5 49 
BE5 F50  F50  F 0 1 N N N 15.778 18.448 10.291 6.328  2.411  -4.390 F50  BE5 50 
BE5 F51  F51  F 0 1 N N N 14.351 20.974 9.593  5.565  0.243  -2.898 F51  BE5 51 
BE5 F52  F52  F 0 1 N N N 9.143  21.560 3.121  -5.567 0.232  2.898  F52  BE5 52 
BE5 H02  H02  H 0 1 N N N 18.583 22.619 8.076  2.248  2.763  -1.188 H02  BE5 53 
BE5 H03  H03  H 0 1 N N N 19.794 20.477 8.671  2.936  4.711  -2.525 H03  BE5 54 
BE5 H04  H04  H 0 1 N N N 18.512 18.496 9.712  4.867  4.546  -4.042 H04  BE5 55 
BE5 H10  H10  H 0 1 N N N 5.932  25.090 2.262  -4.895 4.547  4.011  H10  BE5 56 
BE5 H11  H11  H 0 1 N N N 7.824  26.673 1.421  -2.964 4.712  2.492  H11  BE5 57 
BE5 H12  H12  H 0 1 N N N 10.222 25.885 1.390  -2.265 2.758  1.170  H12  BE5 58 
BE5 H131 1H13 H 0 0 N N N 11.908 24.323 1.716  -4.191 -0.016 0.484  H131 BE5 59 
BE5 H132 2H13 H 0 0 N N N 11.499 22.728 1.342  -3.109 -0.521 1.804  H132 BE5 60 
BE5 H15  H15  H 0 1 N N N 12.198 25.070 4.136  -2.148 -1.413 0.168  H15  BE5 61 
BE5 H16  H16  H 0 1 N N N 12.684 22.758 6.099  -0.105 0.366  -1.236 H16  BE5 62 
BE5 H17  H17  H 0 1 N N N 14.142 22.822 4.015  0.102  0.376  1.234  H17  BE5 63 
BE5 H18  H18  H 0 1 N N N 16.275 23.063 5.771  2.156  -1.402 -0.156 H18  BE5 64 
BE5 H21  H21  H 0 1 N N N 17.174 21.152 5.274  1.842  -2.242 2.385  H21  BE5 65 
BE5 H231 1H23 H 0 0 N N N 16.708 24.030 7.982  4.190  0.005  -0.482 H231 BE5 66 
BE5 H232 2H23 H 0 0 N N N 15.588 23.889 9.230  3.112  -0.516 -1.799 H232 BE5 67 
BE5 H24  H24  H 0 1 N N N 15.681 24.601 4.095  0.282  -2.443 0.885  H24  BE5 68 
BE5 H25  H25  H 0 1 N N N 13.807 24.549 7.168  -0.268 -2.451 -0.865 H25  BE5 69 
BE5 H28  H28  H 0 1 N N N 10.428 26.185 4.826  -1.830 -2.270 -2.367 H28  BE5 70 
BE5 H29  H29  H 0 1 N N N 8.362  24.617 6.344  -4.116 -1.053 -3.760 H29  BE5 71 
BE5 H32  H32  H 0 1 N N N 11.215 25.613 7.966  -1.549 0.878  -3.985 H32  BE5 72 
BE5 H33  H33  H 0 1 N N N 11.309 27.040 10.156 -0.325 1.644  -5.976 H33  BE5 73 
BE5 H34  H34  H 0 1 N N N 9.296  28.502 10.798 -0.407 0.324  -8.055 H34  BE5 74 
BE5 H35  H35  H 0 1 N N N 7.115  26.036 4.814  -4.331 -3.376 -4.091 H35  BE5 75 
BE5 H36  H36  H 0 1 N N N 7.831  28.237 4.531  -2.469 -4.728 -4.248 H36  BE5 76 
BE5 H37  H37  H 0 1 N N N 7.186  28.584 9.321  -1.712 -1.758 -8.136 H37  BE5 77 
BE5 H381 1H38 H 0 0 N N N 6.097  26.337 7.068  -2.750 -3.717 -6.334 H381 BE5 78 
BE5 H382 2H38 H 0 0 N N N 6.300  27.913 6.645  -4.215 -2.688 -6.339 H382 BE5 79 
BE5 H39  H39  H 0 1 N N N 15.651 18.634 5.838  4.111  -0.981 3.774  H39  BE5 80 
BE5 H42  H42  H 0 1 N N N 14.794 20.104 2.909  1.495  0.879  4.008  H42  BE5 81 
BE5 H43  H43  H 0 1 N N N 15.012 19.101 0.505  0.251  1.599  6.004  H43  BE5 82 
BE5 H44  H44  H 0 1 N N N 16.691 17.218 0.081  0.368  0.268  8.074  H44  BE5 83 
BE5 H45  H45  H 0 1 N N N 17.875 18.362 6.722  4.392  -3.295 4.088  H45  BE5 84 
BE5 H46  H46  H 0 1 N N N 19.671 19.334 5.581  2.596  -4.712 4.194  H46  BE5 85 
BE5 H47  H47  H 0 1 N N N 18.169 16.291 1.965  1.729  -1.778 8.143  H47  BE5 86 
BE5 H481 1H48 H 0 0 N N N 17.680 16.413 5.274  2.819  -3.697 6.328  H481 BE5 87 
BE5 H482 2H48 H 0 0 N N N 19.082 17.032 4.646  4.255  -2.629 6.341  H482 BE5 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 
BE5 C01 C02  DOUB Y N 1  
BE5 C01 C06  SING Y N 2  
BE5 C01 C23  SING N N 3  
BE5 C02 C03  SING Y N 4  
BE5 C02 H02  SING N N 5  
BE5 C03 C04  DOUB Y N 6  
BE5 C03 H03  SING N N 7  
BE5 C04 C05  SING Y N 8  
BE5 C04 H04  SING N N 9  
BE5 C05 C06  DOUB Y N 10 
BE5 C05 F50  SING N N 11 
BE5 C06 F51  SING N N 12 
BE5 C07 C08  DOUB Y N 13 
BE5 C07 C12  SING Y N 14 
BE5 C07 C13  SING N N 15 
BE5 C08 C09  SING Y N 16 
BE5 C08 F52  SING N N 17 
BE5 C09 C10  DOUB Y N 18 
BE5 C09 F49  SING N N 19 
BE5 C10 C11  SING Y N 20 
BE5 C10 H10  SING N N 21 
BE5 C11 C12  DOUB Y N 22 
BE5 C11 H11  SING N N 23 
BE5 C12 H12  SING N N 24 
BE5 C13 O14  SING N N 25 
BE5 C13 H131 SING N N 26 
BE5 C13 H132 SING N N 27 
BE5 O14 C15  SING N N 28 
BE5 C15 C16  SING N N 29 
BE5 C15 C26  SING N N 30 
BE5 C15 H15  SING N N 31 
BE5 C16 C17  SING N N 32 
BE5 C16 O25  SING N N 33 
BE5 C16 H16  SING N N 34 
BE5 C17 C18  SING N N 35 
BE5 C17 O24  SING N N 36 
BE5 C17 H17  SING N N 37 
BE5 C18 C19  SING N N 38 
BE5 C18 O22  SING N N 39 
BE5 C18 H18  SING N N 40 
BE5 C19 O20  DOUB N N 41 
BE5 C19 N21  SING N N 42 
BE5 N21 C39  SING N N 43 
BE5 N21 H21  SING N N 44 
BE5 O22 C23  SING N N 45 
BE5 C23 H231 SING N N 46 
BE5 C23 H232 SING N N 47 
BE5 O24 H24  SING N N 48 
BE5 O25 H25  SING N N 49 
BE5 C26 O27  DOUB N N 50 
BE5 C26 N28  SING N N 51 
BE5 N28 C29  SING N N 52 
BE5 N28 H28  SING N N 53 
BE5 C29 C30  SING N N 54 
BE5 C29 C35  SING N N 55 
BE5 C29 H29  SING N N 56 
BE5 C30 C31  DOUB Y N 57 
BE5 C30 C32  SING Y N 58 
BE5 C31 C37  SING Y N 59 
BE5 C31 C38  SING N N 60 
BE5 C32 C33  DOUB Y N 61 
BE5 C32 H32  SING N N 62 
BE5 C33 C34  SING Y N 63 
BE5 C33 H33  SING N N 64 
BE5 C34 C37  DOUB Y N 65 
BE5 C34 H34  SING N N 66 
BE5 C35 O36  SING N N 67 
BE5 C35 C38  SING N N 68 
BE5 C35 H35  SING N N 69 
BE5 O36 H36  SING N N 70 
BE5 C37 H37  SING N N 71 
BE5 C38 H381 SING N N 72 
BE5 C38 H382 SING N N 73 
BE5 C39 C40  SING N N 74 
BE5 C39 C45  SING N N 75 
BE5 C39 H39  SING N N 76 
BE5 C40 C41  DOUB Y N 77 
BE5 C40 C42  SING Y N 78 
BE5 C41 C47  SING Y N 79 
BE5 C41 C48  SING N N 80 
BE5 C42 C43  DOUB Y N 81 
BE5 C42 H42  SING N N 82 
BE5 C43 C44  SING Y N 83 
BE5 C43 H43  SING N N 84 
BE5 C44 C47  DOUB Y N 85 
BE5 C44 H44  SING N N 86 
BE5 C45 O46  SING N N 87 
BE5 C45 C48  SING N N 88 
BE5 C45 H45  SING N N 89 
BE5 O46 H46  SING N N 90 
BE5 C47 H47  SING N N 91 
BE5 C48 H481 SING N N 92 
BE5 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 
BE5 SMILES           ACDLabs              10.04 Fc1cccc(c1F)COC(C(=O)NC3c2ccccc2CC3O)C(O)C(O)C(OCc4cccc(F)c4F)C(=O)NC6c5ccccc5CC6O 
BE5 InChI            InChI                1.02b 
;InChI=1/C38H36F4N2O8/c39-25-13-5-9-21(29(25)41)17-51-35(37(49)43-31-23-11-3-1-7-19(23)15-27(31)45)33(47)34(48)36(52-18-22-10-6-14-26(40)30(22)42)38(50)44-32-24-12-4-2-8-20(24)16-28(32)46/h1-14,27-28,31-36,45-48H,15-18H2,(H,43,49)(H,44,50)/t27-,28-,31+,32+,33-,34-,35-,36-/m1/s1/f/h43-44H
;
BE5 InChIKey         InChI                1.02b FJIRQAXCBOCEQN-GBUFVUQVDS 
BE5 SMILES_CANONICAL CACTVS               3.341 O[C@@H]1Cc2ccccc2[C@@H]1NC(=O)[C@H](OCc3cccc(F)c3F)[C@H](O)[C@@H](O)[C@@H](OCc4cccc(F)c4F)C(=O)N[C@@H]5[C@H](O)Cc6ccccc56 
BE5 SMILES           CACTVS               3.341 O[CH]1Cc2ccccc2[CH]1NC(=O)[CH](OCc3cccc(F)c3F)[CH](O)[CH](O)[CH](OCc4cccc(F)c4F)C(=O)N[CH]5[CH](O)Cc6ccccc56 
BE5 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)OCc5cccc(c5F)F)O)O)OCc6cccc(c6F)F)O 
BE5 SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)CC(C2NC(=O)C(C(C(C(C(=O)NC3c4ccccc4CC3O)OCc5cccc(c5F)F)O)O)OCc6cccc(c6F)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 
BE5 "SYSTEMATIC NAME" ACDLabs              10.04 
;(2R,3R,4R,5R)-2,5-bis[(2,3-difluorobenzyl)oxy]-3,4-dihydroxy-N,N'-bis[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]hexanediamide (non-preferred name)
;
BE5 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2R,3R,4R,5R)-2,5-bis[(2,3-difluorophenyl)methoxy]-3,4-dihydroxy-N,N'-bis[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]hexanediamide"                  
# 
