data_B8L
# 
_chem_comp.id                                    B8L 
_chem_comp.name                                  "3-[(3-SEC-BUTYL-4-HYDROXYBENZOYL)AMINO]AZEPAN-4-YL 4-(2-HYDROXY-5-METHOXYBENZOYL)BENZOATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C32 H36 N2 O7" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "BALANOL ANALOG 8" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-12-03 
_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                        560.637 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     B8L 
_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        1REK 
_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 
B8L O1   O1   O 0 1 N N N 17.455 38.803 20.047 4.873  -1.259 3.255   O1   B8L 1  
B8L C1   C1   C 0 1 Y N N 16.077 39.182 19.831 3.568  -0.930 3.432   C1   B8L 2  
B8L C2   C2   C 0 1 Y N N 15.723 40.532 19.819 2.606  -1.411 2.552   C2   B8L 3  
B8L C3   C3   C 0 1 Y N N 14.396 40.900 19.569 1.282  -1.080 2.728   C3   B8L 4  
B8L C4   C4   C 0 1 Y N N 13.393 39.938 19.346 0.904  -0.263 3.797   C4   B8L 5  
B8L C5   C5   C 0 1 Y N N 13.782 38.580 19.375 1.873  0.214  4.683   C5   B8L 6  
B8L C6   C6   C 0 1 Y N N 15.113 38.193 19.617 3.196  -0.122 4.500   C6   B8L 7  
B8L C7   C7   C 0 1 N N N 12.038 40.323 19.311 -0.514 0.094  3.990   C7   B8L 8  
B8L O7   O7   O 0 1 N N N 11.668 41.502 19.366 -0.841 0.804  4.920   O7   B8L 9  
B8L N8   N8   N 0 1 N N N 11.177 39.314 19.106 -1.448 -0.366 3.134   N8   B8L 10 
B8L C8   C8   C 0 1 N N R 9.734  39.438 19.282 -2.856 -0.012 3.325   C8   B8L 11 
B8L C9   C9   C 0 1 N N R 8.954  39.142 17.968 -3.553 0.022  1.989   C9   B8L 12 
B8L C10  C10  C 0 1 N N N 7.532  38.556 18.087 -4.669 1.085  1.945   C10  B8L 13 
B8L C11  C11  C 0 1 N N N 6.660  39.315 19.075 -5.471 1.117  3.264   C11  B8L 14 
B8L C12  C12  C 0 1 N N N 6.809  38.752 20.487 -5.718 -0.277 3.784   C12  B8L 15 
B8L N13  N13  N 0 1 N N N 8.122  39.027 21.062 -4.704 -0.587 4.810   N13  B8L 16 
B8L O9   O9   O 0 1 N N N 8.929  40.405 17.287 -2.578 0.319  0.955   O9   B8L 17 
B8L C14  C14  C 0 1 N N N 9.387  38.583 20.496 -3.535 -1.064 4.222   C14  B8L 18 
B8L C15  C15  C 0 1 N N N 8.522  40.335 15.886 -2.724 -0.202 -0.277  C15  B8L 19 
B8L O15  O15  O 0 1 N N N 8.623  39.281 15.261 -3.672 -0.920 -0.524  O15  B8L 20 
B8L C16  C16  C 0 1 Y N N 7.783  41.368 15.310 -1.730 0.099  -1.330  C16  B8L 21 
B8L C17  C17  C 0 1 Y N N 7.852  41.635 13.932 -0.644 0.929  -1.048  C17  B8L 22 
B8L C18  C18  C 0 1 Y N N 7.114  42.680 13.362 0.284  1.206  -2.027  C18  B8L 23 
B8L C19  C19  C 0 1 Y N N 6.303  43.492 14.158 0.132  0.665  -3.306  C19  B8L 24 
B8L C20  C20  C 0 1 Y N N 6.237  43.230 15.529 -0.956 -0.160 -3.590  C20  B8L 25 
B8L C21  C21  C 0 1 Y N N 6.976  42.186 16.099 -1.882 -0.441 -2.609  C21  B8L 26 
B8L C22  C22  C 0 1 N N N 5.526  44.508 13.576 1.127  0.966  -4.359  C22  B8L 27 
B8L O22  O22  O 0 1 N N N 4.923  44.253 12.526 2.008  1.777  -4.149  O22  B8L 28 
B8L C23  C23  C 0 1 Y N N 5.357  45.772 14.156 1.049  0.284  -5.663  C23  B8L 29 
B8L C24  C24  C 0 1 Y N N 4.042  46.214 14.296 0.951  1.030  -6.842  C24  B8L 30 
B8L C26  C26  C 0 1 Y N N 3.741  47.519 14.716 0.879  0.383  -8.061  C26  B8L 31 
B8L O26  O26  O 0 1 N N N 2.356  47.951 14.837 0.783  1.107  -9.208  O26  B8L 32 
B8L C27  C27  C 0 1 Y N N 4.760  48.425 14.987 0.904  -1.005 -8.118  C27  B8L 33 
B8L C28  C28  C 0 1 Y N N 6.079  48.009 14.858 1.000  -1.750 -6.960  C28  B8L 34 
B8L C29  C29  C 0 1 Y N N 6.372  46.709 14.422 1.079  -1.116 -5.729  C29  B8L 35 
B8L O29  O29  O 0 1 N N N 7.750  46.322 14.231 1.174  -1.849 -4.591  O29  B8L 36 
B8L C66  C66  C 0 1 N N S 15.512 36.754 19.651 4.242  0.392  5.455   C66  B8L 37 
B8L C71  C71  C 0 1 N N N 15.179 36.026 18.334 3.928  -0.099 6.869   C71  B8L 38 
B8L C72  C72  C 0 1 N N N 14.901 36.055 20.860 4.243  1.922  5.435   C72  B8L 39 
B8L C81  C81  C 0 1 N N N 16.188 36.380 17.212 4.990  0.423  7.838   C81  B8L 40 
B8L C30  C30  C 0 1 N N N 1.289  47.060 15.044 0.727  0.169  -10.285 C30  B8L 41 
B8L HO1  HO1  H 0 1 N N N 17.696 37.884 20.055 5.257  -0.579 2.684   HO1  B8L 42 
B8L H2   H2   H 0 1 N N N 16.488 41.304 20.006 2.899  -2.043 1.726   H2   B8L 43 
B8L H3   H3   H 0 1 N N N 14.135 41.971 19.547 0.535  -1.451 2.041   H3   B8L 44 
B8L H5   H5   H 0 1 N N N 13.023 37.798 19.203 1.585  0.845  5.510   H5   B8L 45 
B8L HN8  HN8  H 0 1 N N N 11.623 38.444 18.813 -1.187 -0.933 2.391   HN8  B8L 46 
B8L H8   H8   H 0 1 N N N 9.408  40.483 19.493 -2.924 0.967  3.797   H8   B8L 47 
B8L H9   H9   H 0 1 N N N 9.478  38.315 17.433 -3.989 -0.957 1.794   H9   B8L 48 
B8L H101 1H10 H 0 0 N N N 7.041  38.494 17.087 -5.346 0.858  1.122   H101 B8L 49 
B8L H102 2H10 H 0 0 N N N 7.567  37.470 18.339 -4.220 2.064  1.778   H102 B8L 50 
B8L H111 1H11 H 0 0 N N N 6.865  40.410 19.046 -6.428 1.608  3.088   H111 B8L 51 
B8L H112 2H11 H 0 0 N N N 5.593  39.333 18.751 -4.912 1.683  4.009   H112 B8L 52 
B8L H121 1H12 H 0 0 N N N 5.994  39.119 21.153 -5.640 -0.991 2.965   H121 B8L 53 
B8L H122 2H12 H 0 0 N N N 6.581  37.660 20.510 -6.713 -0.331 4.226   H122 B8L 54 
B8L H13  H13  H 0 1 N N N 8.097  38.693 22.025 -5.077 -1.341 5.367   H13  B8L 55 
B8L H141 1H14 H 0 0 N N N 9.380  37.494 20.255 -3.776 -1.940 3.618   H141 B8L 56 
B8L H142 2H14 H 0 0 N N N 10.206 38.575 21.252 -2.840 -1.360 5.007   H142 B8L 57 
B8L H17  H17  H 0 1 N N N 8.496  41.014 13.287 -0.527 1.348  -0.059  H17  B8L 58 
B8L H18  H18  H 0 1 N N N 7.172  42.865 12.276 1.126  1.845  -1.808  H18  B8L 59 
B8L H20  H20  H 0 1 N N N 5.593  43.855 16.169 -1.073 -0.579 -4.578  H20  B8L 60 
B8L H21  H21  H 0 1 N N N 6.921  42.005 17.185 -2.725 -1.080 -2.828  H21  B8L 61 
B8L H24  H24  H 0 1 N N N 3.220  45.514 14.069 0.931  2.109  -6.800  H24  B8L 62 
B8L H27  H27  H 0 1 N N N 4.525  49.456 15.299 0.847  -1.504 -9.074  H27  B8L 63 
B8L H28  H28  H 0 1 N N N 6.893  48.711 15.101 1.019  -2.828 -7.012  H28  B8L 64 
B8L H29  H29  H 0 1 N N N 8.435  46.954 14.410 2.117  -1.983 -4.423  H29  B8L 65 
B8L H66  H66  H 0 1 N N N 16.621 36.713 19.756 5.223  0.024  5.152   H66  B8L 66 
B8L H711 1H71 H 0 0 N N N 15.109 34.923 18.485 3.927  -1.188 6.883   H711 B8L 67 
B8L H712 2H71 H 0 0 N N N 14.129 36.224 18.014 2.947  0.268  7.172   H712 B8L 68 
B8L H721 1H72 H 0 0 N N N 15.198 34.980 20.885 3.262  2.290  5.737   H721 B8L 69 
B8L H722 2H72 H 0 0 N N N 15.155 36.577 21.811 4.999  2.294  6.125   H722 B8L 70 
B8L H723 3H72 H 0 0 N N N 13.793 36.177 20.892 4.467  2.272  4.427   H723 B8L 71 
B8L H811 1H81 H 0 0 N N N 15.947 35.853 16.259 4.766  0.073  8.846   H811 B8L 72 
B8L H812 2H81 H 0 0 N N N 16.257 37.482 17.060 5.970  0.055  7.536   H812 B8L 73 
B8L H813 3H81 H 0 0 N N N 17.237 36.181 17.531 4.990  1.513  7.824   H813 B8L 74 
B8L H301 1H30 H 0 0 N N N 0.228  47.390 15.136 0.649  0.706  -11.230 H301 B8L 75 
B8L H302 2H30 H 0 0 N N N 1.329  46.297 14.231 1.632  -0.438 -10.285 H302 B8L 76 
B8L H303 3H30 H 0 0 N N N 1.530  46.457 15.950 -0.143 -0.474 -10.160 H303 B8L 77 
# 
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 
B8L O1  C1   SING N N 1  
B8L O1  HO1  SING N N 2  
B8L C1  C2   DOUB Y N 3  
B8L C1  C6   SING Y N 4  
B8L C2  C3   SING Y N 5  
B8L C2  H2   SING N N 6  
B8L C3  C4   DOUB Y N 7  
B8L C3  H3   SING N N 8  
B8L C4  C5   SING Y N 9  
B8L C4  C7   SING N N 10 
B8L C5  C6   DOUB Y N 11 
B8L C5  H5   SING N N 12 
B8L C6  C66  SING N N 13 
B8L C7  O7   DOUB N N 14 
B8L C7  N8   SING N N 15 
B8L N8  C8   SING N N 16 
B8L N8  HN8  SING N N 17 
B8L C8  C9   SING N N 18 
B8L C8  C14  SING N N 19 
B8L C8  H8   SING N N 20 
B8L C9  C10  SING N N 21 
B8L C9  O9   SING N N 22 
B8L C9  H9   SING N N 23 
B8L C10 C11  SING N N 24 
B8L C10 H101 SING N N 25 
B8L C10 H102 SING N N 26 
B8L C11 C12  SING N N 27 
B8L C11 H111 SING N N 28 
B8L C11 H112 SING N N 29 
B8L C12 N13  SING N N 30 
B8L C12 H121 SING N N 31 
B8L C12 H122 SING N N 32 
B8L N13 C14  SING N N 33 
B8L N13 H13  SING N N 34 
B8L O9  C15  SING N N 35 
B8L C14 H141 SING N N 36 
B8L C14 H142 SING N N 37 
B8L C15 O15  DOUB N N 38 
B8L C15 C16  SING N N 39 
B8L C16 C17  SING Y N 40 
B8L C16 C21  DOUB Y N 41 
B8L C17 C18  DOUB Y N 42 
B8L C17 H17  SING N N 43 
B8L C18 C19  SING Y N 44 
B8L C18 H18  SING N N 45 
B8L C19 C20  DOUB Y N 46 
B8L C19 C22  SING N N 47 
B8L C20 C21  SING Y N 48 
B8L C20 H20  SING N N 49 
B8L C21 H21  SING N N 50 
B8L C22 O22  DOUB N N 51 
B8L C22 C23  SING N N 52 
B8L C23 C24  SING Y N 53 
B8L C23 C29  DOUB Y N 54 
B8L C24 C26  DOUB Y N 55 
B8L C24 H24  SING N N 56 
B8L C26 O26  SING N N 57 
B8L C26 C27  SING Y N 58 
B8L O26 C30  SING N N 59 
B8L C27 C28  DOUB Y N 60 
B8L C27 H27  SING N N 61 
B8L C28 C29  SING Y N 62 
B8L C28 H28  SING N N 63 
B8L C29 O29  SING N N 64 
B8L O29 H29  SING N N 65 
B8L C66 C71  SING N N 66 
B8L C66 C72  SING N N 67 
B8L C66 H66  SING N N 68 
B8L C71 C81  SING N N 69 
B8L C71 H711 SING N N 70 
B8L C71 H712 SING N N 71 
B8L C72 H721 SING N N 72 
B8L C72 H722 SING N N 73 
B8L C72 H723 SING N N 74 
B8L C81 H811 SING N N 75 
B8L C81 H812 SING N N 76 
B8L C81 H813 SING N N 77 
B8L C30 H301 SING N N 78 
B8L C30 H302 SING N N 79 
B8L C30 H303 SING N N 80 
# 
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 
B8L SMILES           ACDLabs              10.04 O=C(c1cc(OC)ccc1O)c2ccc(cc2)C(=O)OC4CCCNCC4NC(=O)c3ccc(O)c(c3)C(C)CC 
B8L InChI            InChI                1.02b 
InChI=1/C32H36N2O7/c1-4-19(2)24-16-22(11-13-27(24)35)31(38)34-26-18-33-15-5-6-29(26)41-32(39)21-9-7-20(8-10-21)30(37)25-17-23(40-3)12-14-28(25)36/h7-14,16-17,19,26,29,33,35-36H,4-6,15,18H2,1-3H3,(H,34,38)/t19-,26+,29+/m0/s1/f/h34H 
B8L InChIKey         InChI                1.02b XVLMXAUKCDSMMW-JSMOZKDMDS 
B8L SMILES_CANONICAL CACTVS               3.341 CC[C@H](C)c1cc(ccc1O)C(=O)N[C@@H]2CNCCC[C@H]2OC(=O)c3ccc(cc3)C(=O)c4cc(OC)ccc4O 
B8L SMILES           CACTVS               3.341 CC[CH](C)c1cc(ccc1O)C(=O)N[CH]2CNCCC[CH]2OC(=O)c3ccc(cc3)C(=O)c4cc(OC)ccc4O 
B8L SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC[C@H](C)c1cc(ccc1O)C(=O)N[C@@H]2CNCCC[C@H]2OC(=O)c3ccc(cc3)C(=O)c4cc(ccc4O)OC 
B8L SMILES           "OpenEye OEToolkits" 1.5.0 CCC(C)c1cc(ccc1O)C(=O)NC2CNCCCC2OC(=O)c3ccc(cc3)C(=O)c4cc(ccc4O)OC 
# 
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 
B8L "SYSTEMATIC NAME" ACDLabs              10.04 "(3R,4R)-3-[({4-hydroxy-3-[(1S)-1-methylpropyl]phenyl}carbonyl)amino]azepan-4-yl 4-[(2-hydroxy-5-methoxyphenyl)carbonyl]benzoate" 
B8L "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(3R,4R)-3-[[3-[(2S)-butan-2-yl]-4-hydroxy-phenyl]carbonylamino]azepan-4-yl] 4-(2-hydroxy-5-methoxy-phenyl)carbonylbenzoate"     
# 
