data_BE4
# 
_chem_comp.id                                    BE4 
_chem_comp.name                                  "(2R,3R,4R,5R)-2,5-BIS[(2,4-DIFLUOROBENZYL)OXY]-3,4-DIHYDROXY-N,N'-BIS[(1R,2S)-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                         "INHIBITOR BEA403" 
_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                     BE4 
_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        1W5W 
_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 
BE4 C01  C01  C 0 1 Y N N 16.582 21.931 8.804  3.935  1.384  -1.648 C01  BE4 1  
BE4 C02  C02  C 0 1 Y N N 18.015 21.693 8.545  3.231  2.573  -1.604 C02  BE4 2  
BE4 C03  C03  C 0 1 Y N N 18.665 20.446 8.896  3.674  3.667  -2.322 C03  BE4 3  
BE4 C04  C04  C 0 1 Y N N 17.900 19.360 9.530  4.825  3.574  -3.087 C04  BE4 4  
BE4 C05  C05  C 0 1 Y N N 16.457 19.559 9.806  5.531  2.384  -3.132 C05  BE4 5  
BE4 C06  C06  C 0 1 Y N N 15.810 20.822 9.449  5.088  1.290  -2.407 C06  BE4 6  
BE4 C07  C07  C 0 1 Y N N 9.888  23.785 2.239  -3.944 1.372  1.638  C07  BE4 7  
BE4 C08  C08  C 0 1 Y N N 8.784  22.896 2.660  -5.098 1.277  2.398  C08  BE4 8  
BE4 C09  C09  C 0 1 Y N N 7.380  23.402 2.625  -5.547 2.373  3.114  C09  BE4 9  
BE4 C10  C10  C 0 1 Y N N 7.121  24.802 2.163  -4.849 3.567  3.059  C10  BE4 10 
BE4 C11  C11  C 0 1 Y N N 8.269  25.660 1.750  -3.699 3.662  2.293  C11  BE4 11 
BE4 C12  C12  C 0 1 Y N N 9.604  25.145 1.796  -3.248 2.565  1.584  C12  BE4 12 
BE4 C13  C13  C 0 1 N N N 11.338 23.362 2.249  -3.451 0.176  0.865  C13  BE4 13 
BE4 O14  O14  O 0 1 N N N 11.842 23.015 3.562  -2.258 0.524  0.160  O14  BE4 14 
BE4 C15  C15  C 0 1 N N R 11.889 24.100 4.626  -1.842 -0.643 -0.549 C15  BE4 15 
BE4 C16  C16  C 0 1 N N R 12.946 23.869 5.674  -0.318 -0.639 -0.691 C16  BE4 16 
BE4 C17  C17  C 0 1 N N R 14.249 23.634 5.021  0.322  -0.631 0.697  C17  BE4 17 
BE4 C18  C18  C 0 1 N N R 15.192 22.853 6.019  1.845  -0.627 0.556  C18  BE4 18 
BE4 C19  C19  C 0 1 N N N 15.157 21.349 5.834  2.477  -0.619 1.924  C19  BE4 19 
BE4 O20  O20  O 0 1 N N N 14.105 20.710 6.055  3.205  0.294  2.251  O20  BE4 20 
BE4 N21  N21  N 0 1 N N N 16.303 20.706 5.445  2.233  -1.627 2.785  N21  BE4 21 
BE4 O22  O22  O 0 1 N N N 14.898 23.181 7.442  2.253  0.538  -0.163 O22  BE4 22 
BE4 C23  C23  C 0 1 N N N 16.016 23.296 8.378  3.449  0.192  -0.865 C23  BE4 23 
BE4 O24  O24  O 0 1 N N N 14.800 24.891 4.570  -0.085 -1.796 1.417  O24  BE4 24 
BE4 O25  O25  O 0 1 N N N 13.115 25.036 6.579  0.096  -1.807 -1.401 O25  BE4 25 
BE4 C26  C26  C 0 1 N N N 10.668 24.246 5.469  -2.474 -0.651 -1.917 C26  BE4 26 
BE4 O27  O27  O 0 1 N N N 10.306 23.275 6.179  -3.207 0.254  -2.252 O27  BE4 27 
BE4 N28  N28  N 0 1 N N N 9.989  25.423 5.415  -2.223 -1.664 -2.770 N28  BE4 28 
BE4 C29  C29  C 0 1 N N S 8.780  25.671 6.174  -2.837 -1.672 -4.100 C29  BE4 29 
BE4 C30  C30  C 0 1 Y N N 9.086  26.410 7.432  -1.924 -0.992 -5.106 C30  BE4 30 
BE4 C31  C31  C 0 1 Y N N 7.952  27.273 7.778  -1.877 -1.733 -6.271 C31  BE4 31 
BE4 C32  C32  C 0 1 Y N N 10.293 26.374 8.290  -1.194 0.180  -5.005 C32  BE4 32 
BE4 C33  C33  C 0 1 Y N N 10.337 27.233 9.515  -0.421 0.611  -6.065 C33  BE4 33 
BE4 C34  C34  C 0 1 Y N N 9.182  28.089 9.833  -0.375 -0.129 -7.231 C34  BE4 34 
BE4 C35  C35  C 0 1 N N R 7.722  26.612 5.536  -2.990 -3.118 -4.616 C35  BE4 35 
BE4 O36  O36  O 0 1 N N N 8.433  27.651 4.838  -2.003 -3.973 -4.034 O36  BE4 36 
BE4 C37  C37  C 0 1 Y N N 7.980  28.123 8.979  -1.102 -1.299 -7.334 C37  BE4 37 
BE4 C38  C38  C 0 1 N N N 6.891  27.113 6.755  -2.753 -2.960 -6.133 C38  BE4 38 
BE4 C39  C39  C 0 1 N N S 16.411 19.278 5.244  2.847  -1.619 4.115  C39  BE4 39 
BE4 C40  C40  C 0 1 Y N N 16.313 18.890 3.770  1.919  -0.969 5.118  C40  BE4 40 
BE4 C41  C41  C 0 1 Y N N 17.253 17.823 3.481  1.892  -1.718 6.282  C41  BE4 41 
BE4 C42  C42  C 0 1 Y N N 15.453 19.430 2.705  1.155  0.180  5.022  C42  BE4 42 
BE4 C43  C43  C 0 1 Y N N 15.565 18.863 1.324  0.370  0.585  6.084  C43  BE4 43 
BE4 C44  C44  C 0 1 Y N N 16.530 17.786 1.074  0.345  -0.161 7.247  C44  BE4 44 
BE4 C45  C45  C 0 1 N N R 17.818 18.733 5.614  3.045  -3.064 4.622  C45  BE4 45 
BE4 O46  O46  O 0 1 N N N 18.787 19.773 5.321  2.086  -3.945 4.032  O46  BE4 46 
BE4 C47  C47  C 0 1 Y N N 17.385 17.246 2.130  1.104  -1.310 7.345  C47  BE4 47 
BE4 C48  C48  C 0 1 N N N 17.984 17.479 4.743  2.802  -2.919 6.139  C48  BE4 48 
BE4 F49  F49  F 0 1 N N N 5.771  25.318 2.117  -5.289 4.640  3.752  F49  BE4 49 
BE4 F50  F50  F 0 1 N N N 18.537 18.149 9.866  5.258  4.644  -3.789 F50  BE4 50 
BE4 F51  F51  F 0 1 N N N 14.425 21.004 9.714  5.776  0.129  -2.450 F51  BE4 51 
BE4 F52  F52  F 0 1 N N N 9.056  21.600 3.086  -5.778 0.111  2.451  F52  BE4 52 
BE4 H02  H02  H 0 1 N N N 18.611 22.490 8.069  2.333  2.647  -1.007 H02  BE4 53 
BE4 H03  H03  H 0 1 N N N 19.739 20.310 8.687  3.123  4.595  -2.287 H03  BE4 54 
BE4 H05  H05  H 0 1 N N N 15.871 18.754 10.281 6.428  2.310  -3.728 H05  BE4 55 
BE4 H09  H09  H 0 1 N N N 6.544  22.753 2.936  -6.444 2.299  3.711  H09  BE4 56 
BE4 H11  H11  H 0 1 N N N 8.089  26.693 1.408  -3.154 4.594  2.250  H11  BE4 57 
BE4 H12  H12  H 0 1 N N N 10.441 25.795 1.488  -2.351 2.640  0.987  H12  BE4 58 
BE4 H131 1H13 H 0 0 N N N 11.977 24.145 1.779  -4.215 -0.135 0.153  H131 BE4 59 
BE4 H132 2H13 H 0 0 N N N 11.507 22.525 1.531  -3.241 -0.640 1.554  H132 BE4 60 
BE4 H15  H15  H 0 1 N N N 12.093 25.076 4.127  -2.153 -1.532 -0.000 H15  BE4 61 
BE4 H16  H16  H 0 1 N N N 12.672 22.973 6.279  -0.007 0.249  -1.240 H16  BE4 62 
BE4 H17  H17  H 0 1 N N N 14.078 22.989 4.128  0.005  0.259  1.239  H17  BE4 63 
BE4 H18  H18  H 0 1 N N N 16.236 23.186 5.814  2.162  -1.518 0.014  H18  BE4 64 
BE4 H21  H21  H 0 1 N N N 17.136 21.273 5.286  1.651  -2.357 2.523  H21  BE4 65 
BE4 H231 1H23 H 0 0 N N N 16.819 23.948 7.962  4.215  -0.109 -0.150 H231 BE4 66 
BE4 H232 2H23 H 0 0 N N N 15.730 23.904 9.268  3.244  -0.632 -1.547 H232 BE4 67 
BE4 H24  H24  H 0 1 N N N 15.639 24.740 4.150  0.213  -2.560 0.905  H24  BE4 68 
BE4 H25  H25  H 0 1 N N N 13.782 24.890 7.240  -0.197 -2.569 -0.883 H25  BE4 69 
BE4 H28  H28  H 0 1 N N N 10.347 26.165 4.813  -1.636 -2.389 -2.502 H28  BE4 70 
BE4 H29  H29  H 0 1 N N N 8.300  24.697 6.428  -3.806 -1.173 -4.071 H29  BE4 71 
BE4 H32  H32  H 0 1 N N N 11.146 25.725 8.030  -1.230 0.759  -4.094 H32  BE4 72 
BE4 H33  H33  H 0 1 N N N 11.224 27.225 10.171 0.146  1.526  -5.983 H33  BE4 73 
BE4 H34  H34  H 0 1 N N N 9.217  28.723 10.735 0.228  0.205  -8.061 H34  BE4 74 
BE4 H35  H35  H 0 1 N N N 7.072  26.044 4.830  -3.993 -3.497 -4.418 H35  BE4 75 
BE4 H36  H36  H 0 1 N N N 7.786  28.227 4.448  -2.124 -4.848 -4.427 H36  BE4 76 
BE4 H37  H37  H 0 1 N N N 7.123  28.769 9.234  -1.065 -1.878 -8.245 H37  BE4 77 
BE4 H381 1H38 H 0 0 N N N 6.036  26.462 7.051  -2.240 -3.837 -6.529 H381 BE4 78 
BE4 H382 2H38 H 0 0 N N N 6.266  28.017 6.569  -3.700 -2.810 -6.650 H382 BE4 79 
BE4 H39  H39  H 0 1 N N N 15.627 18.747 5.833  3.802  -1.094 4.087  H39  BE4 80 
BE4 H42  H42  H 0 1 N N N 14.737 20.240 2.921  1.175  0.764  4.114  H42  BE4 81 
BE4 H43  H43  H 0 1 N N N 14.932 19.249 0.507  -0.223 1.484  6.005  H43  BE4 82 
BE4 H44  H44  H 0 1 N N N 16.613 17.370 0.056  -0.268 0.153  8.078  H44  BE4 83 
BE4 H45  H45  H 0 1 N N N 17.856 18.462 6.695  4.059  -3.409 4.422  H45  BE4 84 
BE4 H46  H46  H 0 1 N N N 19.647 19.440 5.547  2.262  -4.827 4.387  H46  BE4 85 
BE4 H47  H47  H 0 1 N N N 18.104 16.435 1.923  1.084  -1.893 8.254  H47  BE4 86 
BE4 H481 1H48 H 0 0 N N N 17.646 16.534 5.228  2.315  -3.811 6.531  H481 BE4 87 
BE4 H482 2H48 H 0 0 N N N 19.042 17.162 4.590  3.745  -2.742 6.657  H482 BE4 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 
BE4 C01 C02  DOUB Y N 1  
BE4 C01 C06  SING Y N 2  
BE4 C01 C23  SING N N 3  
BE4 C02 C03  SING Y N 4  
BE4 C02 H02  SING N N 5  
BE4 C03 C04  DOUB Y N 6  
BE4 C03 H03  SING N N 7  
BE4 C04 C05  SING Y N 8  
BE4 C04 F50  SING N N 9  
BE4 C05 C06  DOUB Y N 10 
BE4 C05 H05  SING N N 11 
BE4 C06 F51  SING N N 12 
BE4 C07 C08  DOUB Y N 13 
BE4 C07 C12  SING Y N 14 
BE4 C07 C13  SING N N 15 
BE4 C08 C09  SING Y N 16 
BE4 C08 F52  SING N N 17 
BE4 C09 C10  DOUB Y N 18 
BE4 C09 H09  SING N N 19 
BE4 C10 C11  SING Y N 20 
BE4 C10 F49  SING N N 21 
BE4 C11 C12  DOUB Y N 22 
BE4 C11 H11  SING N N 23 
BE4 C12 H12  SING N N 24 
BE4 C13 O14  SING N N 25 
BE4 C13 H131 SING N N 26 
BE4 C13 H132 SING N N 27 
BE4 O14 C15  SING N N 28 
BE4 C15 C16  SING N N 29 
BE4 C15 C26  SING N N 30 
BE4 C15 H15  SING N N 31 
BE4 C16 C17  SING N N 32 
BE4 C16 O25  SING N N 33 
BE4 C16 H16  SING N N 34 
BE4 C17 C18  SING N N 35 
BE4 C17 O24  SING N N 36 
BE4 C17 H17  SING N N 37 
BE4 C18 C19  SING N N 38 
BE4 C18 O22  SING N N 39 
BE4 C18 H18  SING N N 40 
BE4 C19 O20  DOUB N N 41 
BE4 C19 N21  SING N N 42 
BE4 N21 C39  SING N N 43 
BE4 N21 H21  SING N N 44 
BE4 O22 C23  SING N N 45 
BE4 C23 H231 SING N N 46 
BE4 C23 H232 SING N N 47 
BE4 O24 H24  SING N N 48 
BE4 O25 H25  SING N N 49 
BE4 C26 O27  DOUB N N 50 
BE4 C26 N28  SING N N 51 
BE4 N28 C29  SING N N 52 
BE4 N28 H28  SING N N 53 
BE4 C29 C30  SING N N 54 
BE4 C29 C35  SING N N 55 
BE4 C29 H29  SING N N 56 
BE4 C30 C31  DOUB Y N 57 
BE4 C30 C32  SING Y N 58 
BE4 C31 C37  SING Y N 59 
BE4 C31 C38  SING N N 60 
BE4 C32 C33  DOUB Y N 61 
BE4 C32 H32  SING N N 62 
BE4 C33 C34  SING Y N 63 
BE4 C33 H33  SING N N 64 
BE4 C34 C37  DOUB Y N 65 
BE4 C34 H34  SING N N 66 
BE4 C35 O36  SING N N 67 
BE4 C35 C38  SING N N 68 
BE4 C35 H35  SING N N 69 
BE4 O36 H36  SING N N 70 
BE4 C37 H37  SING N N 71 
BE4 C38 H381 SING N N 72 
BE4 C38 H382 SING N N 73 
BE4 C39 C40  SING N N 74 
BE4 C39 C45  SING N N 75 
BE4 C39 H39  SING N N 76 
BE4 C40 C41  DOUB Y N 77 
BE4 C40 C42  SING Y N 78 
BE4 C41 C47  SING Y N 79 
BE4 C41 C48  SING N N 80 
BE4 C42 C43  DOUB Y N 81 
BE4 C42 H42  SING N N 82 
BE4 C43 C44  SING Y N 83 
BE4 C43 H43  SING N N 84 
BE4 C44 C47  DOUB Y N 85 
BE4 C44 H44  SING N N 86 
BE4 C45 O46  SING N N 87 
BE4 C45 C48  SING N N 88 
BE4 C45 H45  SING N N 89 
BE4 O46 H46  SING N N 90 
BE4 C47 H47  SING N N 91 
BE4 C48 H481 SING N N 92 
BE4 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 
BE4 SMILES           ACDLabs              10.04 Fc1ccc(c(F)c1)COC(C(=O)NC3c2ccccc2CC3O)C(O)C(O)C(OCc4ccc(F)cc4F)C(=O)NC6c5ccccc5CC6O 
BE4 InChI            InChI                1.02b 
;InChI=1/C38H36F4N2O8/c39-23-11-9-21(27(41)15-23)17-51-35(37(49)43-31-25-7-3-1-5-19(25)13-29(31)45)33(47)34(48)36(52-18-22-10-12-24(40)16-28(22)42)38(50)44-32-26-8-4-2-6-20(26)14-30(32)46/h1-12,15-16,29-36,45-48H,13-14,17-18H2,(H,43,49)(H,44,50)/t29-,30-,31+,32+,33-,34-,35-,36-/m1/s1/f/h43-44H
;
BE4 InChIKey         InChI                1.02b YVNITSOLRPDTNX-SBWOTXQCDV 
BE4 SMILES_CANONICAL CACTVS               3.341 O[C@@H]1Cc2ccccc2[C@@H]1NC(=O)[C@H](OCc3ccc(F)cc3F)[C@H](O)[C@@H](O)[C@@H](OCc4ccc(F)cc4F)C(=O)N[C@@H]5[C@H](O)Cc6ccccc56 
BE4 SMILES           CACTVS               3.341 O[CH]1Cc2ccccc2[CH]1NC(=O)[CH](OCc3ccc(F)cc3F)[CH](O)[CH](O)[CH](OCc4ccc(F)cc4F)C(=O)N[CH]5[CH](O)Cc6ccccc56 
BE4 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)OCc5ccc(cc5F)F)O)O)OCc6ccc(cc6F)F)O 
BE4 SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)CC(C2NC(=O)C(C(C(C(C(=O)NC3c4ccccc4CC3O)OCc5ccc(cc5F)F)O)O)OCc6ccc(cc6F)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 
BE4 "SYSTEMATIC NAME" ACDLabs              10.04 
;(2R,3R,4R,5R)-2,5-bis[(2,4-difluorobenzyl)oxy]-3,4-dihydroxy-N,N'-bis[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]hexanediamide (non-preferred name)
;
BE4 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2R,3R,4R,5R)-2,5-bis[(2,4-difluorophenyl)methoxy]-3,4-dihydroxy-N,N'-bis[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]hexanediamide"                  
# 
