data_HYF
# 
_chem_comp.id                                    HYF 
_chem_comp.name                                  4-HYDROXY-5-ISOBUTYRYL-6-METHYL-1,3,7-TRIS-(3-METHYL-BUT-2-ENYL)-6-(4-METHYL-PENT-3-ENYL)-BICYCLO[3.3.1]NON-3-ENE-2,9-DIONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C35 H52 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         HYPERFORIN 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2002-06-25 
_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                        536.785 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     HYF 
_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        1M13 
_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 
HYF C1   C1   C 0 1 N N N 9.507  71.984 -4.180 0.857  -0.902 -5.734 C1   HYF 1  
HYF C2   C2   C 0 1 N N N 13.665 77.912 -5.865 -4.791 -1.490 -1.744 C2   HYF 2  
HYF C3   C3   C 0 1 N N N 15.188 79.187 -4.255 -3.779 -1.542 0.661  C3   HYF 3  
HYF C4   C4   C 0 1 N N N 5.003  74.687 -1.250 4.955  1.681  0.427  C4   HYF 4  
HYF C5   C5   C 0 1 N N N 6.235  74.668 -0.333 3.436  1.744  0.598  C5   HYF 5  
HYF C6   C6   C 0 1 N N N 5.804  74.281 1.094  2.941  3.148  0.246  C6   HYF 6  
HYF C7   C7   C 0 1 N N N 7.002  76.062 -0.376 2.786  0.738  -0.316 C7   HYF 7  
HYF O8   O8   O 0 1 N N N 6.284  77.048 -0.188 3.313  0.443  -1.361 O8   HYF 8  
HYF C9   C9   C 0 1 N N N 13.315 77.859 -3.346 -2.551 -0.653 -1.253 C9   HYF 9  
HYF C10  C10  C 0 1 N N N 13.998 78.277 -4.434 -3.652 -1.201 -0.801 C10  HYF 10 
HYF C11  C11  C 0 1 N N N 12.081 76.966 -3.295 -1.385 -0.428 -0.324 C11  HYF 11 
HYF C12  C12  C 0 1 N N N 8.482  77.465 -3.142 2.069  -1.994 -1.135 C12  HYF 12 
HYF C13  C13  C 0 1 N N N 13.617 80.891 -0.163 0.682  0.340  6.308  C13  HYF 13 
HYF C14  C14  C 0 1 N N N 11.728 82.666 -0.425 -0.738 -1.784 5.779  C14  HYF 14 
HYF C15  C15  C 0 1 N N N 12.130 81.280 0.042  0.335  -0.801 5.388  C15  HYF 15 
HYF C16  C16  C 0 1 N N N 11.189 80.485 0.607  0.966  -0.940 4.249  C16  HYF 16 
HYF C17  C17  C 0 1 N N N 11.395 79.061 1.156  0.490  -1.955 3.242  C17  HYF 17 
HYF C18  C18  C 0 1 N N N 9.202  77.736 0.059  1.602  -0.647 1.394  C18  HYF 18 
HYF O19  O19  O 0 1 N N N 8.485  78.726 0.260  2.642  -0.734 2.002  O19  HYF 19 
HYF O20  O20  O 0 1 N N N 11.410 76.564 2.580  -1.643 -0.245 2.740  O20  HYF 20 
HYF O21  O21  O 0 1 N N N 8.940  73.713 -0.472 0.431  2.266  -0.485 O21  HYF 21 
HYF C22  C22  C 0 1 N N N 13.892 73.324 -0.313 -4.227 2.167  -1.576 C22  HYF 22 
HYF C23  C23  C 0 1 N N N 12.677 71.160 -1.027 -2.625 3.964  -0.568 C23  HYF 23 
HYF C24  C24  C 0 1 N N N 12.653 72.424 -0.193 -3.201 2.571  -0.550 C24  HYF 24 
HYF C25  C25  C 0 1 N N N 11.557 72.637 0.594  -2.808 1.712  0.357  C25  HYF 25 
HYF C26  C26  C 0 1 N N N 11.132 73.748 1.596  -1.645 2.044  1.256  C26  HYF 26 
HYF C27  C27  C 0 1 N N S 8.644  76.287 -0.635 1.477  0.101  0.074  C27  HYF 27 
HYF C28  C28  C 0 1 N N N 9.382  74.958 -0.002 0.396  1.142  0.254  C28  HYF 28 
HYF C29  C29  C 0 1 N N N 10.418 74.983 0.974  -0.597 0.967  1.140  C29  HYF 29 
HYF C30  C30  C 0 1 N N N 10.916 76.432 1.458  -0.715 -0.161 1.960  C30  HYF 30 
HYF C31  C31  C 0 1 N N R 10.790 77.714 0.464  0.303  -1.277 1.883  C31  HYF 31 
HYF C32  C32  C 0 1 N N N 11.669 77.330 -0.883 -0.164 -2.280 0.818  C32  HYF 32 
HYF C33  C33  C 0 1 N N R 10.940 77.436 -2.301 -0.361 -1.549 -0.510 C33  HYF 33 
HYF C34  C34  C 0 1 N N R 9.390  76.527 -2.253 1.009  -0.900 -0.992 C34  HYF 34 
HYF C35  C35  C 0 1 N N N 9.603  75.247 -3.178 0.800  -0.209 -2.341 C35  HYF 35 
HYF C36  C36  C 0 1 N N N 8.464  74.313 -3.675 0.333  -1.237 -3.373 C36  HYF 36 
HYF C37  C37  C 0 1 N N N 9.034  73.193 -4.549 0.128  -0.557 -4.702 C37  HYF 37 
HYF C38  C38  C 0 1 N N N 9.559  71.492 -2.747 0.522  -0.371 -7.104 C38  HYF 38 
HYF C39  C39  C 0 1 N N N 10.021 71.040 -5.237 2.031  -1.829 -5.551 C39  HYF 39 
HYF H021 1H02 H 0 0 N N N 12.785 77.239 -5.997 -5.579 -2.022 -1.210 H021 HYF 40 
HYF H022 2H02 H 0 0 N N N 13.532 78.836 -6.473 -5.187 -0.552 -2.134 H022 HYF 41 
HYF H023 3H02 H 0 0 N N N 14.559 77.472 -6.364 -4.433 -2.104 -2.569 H023 HYF 42 
HYF H031 1H03 H 0 0 N N N 15.433 79.455 -3.201 -2.897 -1.186 1.194  H031 HYF 43 
HYF H032 2H03 H 0 0 N N N 16.082 78.747 -4.754 -4.669 -1.063 1.069  H032 HYF 44 
HYF H033 3H03 H 0 0 N N N 15.055 80.111 -4.863 -3.862 -2.622 0.776  H033 HYF 45 
HYF H041 1H04 H 0 0 N N N 5.315  74.967 -2.283 5.426  2.409  1.088  H041 HYF 46 
HYF H042 2H04 H 0 0 N N N 4.443  73.722 -1.225 5.308  0.681  0.678  H042 HYF 47 
HYF H043 3H04 H 0 0 N N N 4.195  75.349 -0.858 5.214  1.909  -0.606 H043 HYF 48 
HYF H051 1H05 H 0 0 N N N 6.957  73.901 -0.697 3.177  1.516  1.632  H051 HYF 49 
HYF H061 1H06 H 0 0 N N N 6.698  74.267 1.759  3.200  3.377  -0.787 H061 HYF 50 
HYF H062 2H06 H 0 0 N N N 4.996  74.943 1.485  1.859  3.193  0.368  H062 HYF 51 
HYF H063 3H06 H 0 0 N N N 5.244  73.316 1.119  3.412  3.876  0.907  H063 HYF 52 
HYF H091 1H09 H 0 0 N N N 13.794 78.272 -2.443 -2.478 -0.363 -2.291 H091 HYF 53 
HYF H111 1H11 H 0 0 N N N 11.663 76.833 -4.320 -1.738 -0.425 0.706  H111 HYF 54 
HYF H112 2H11 H 0 0 N N N 12.378 75.916 -3.065 -0.920 0.530  -0.552 H112 HYF 55 
HYF H121 1H12 H 0 0 N N N 8.944  77.613 -4.145 1.737  -2.727 -1.869 H121 HYF 56 
HYF H122 2H12 H 0 0 N N N 7.437  77.081 -3.218 3.008  -1.548 -1.465 H122 HYF 57 
HYF H123 3H12 H 0 0 N N N 8.265  78.434 -2.636 2.218  -2.484 -0.173 H123 HYF 58 
HYF H131 1H13 H 0 0 N N N 13.912 79.872 0.180  0.057  0.291  7.199  H131 HYF 59 
HYF H132 2H13 H 0 0 N N N 13.896 81.023 -1.234 1.731  0.269  6.595  H132 HYF 60 
HYF H133 3H13 H 0 0 N N N 14.275 81.654 0.313  0.509  1.286  5.794  H133 HYF 61 
HYF H141 1H14 H 0 0 N N N 10.658 82.945 -0.277 -0.786 -2.583 5.039  H141 HYF 62 
HYF H142 2H14 H 0 0 N N N 12.386 83.429 0.051  -0.504 -2.207 6.756  H142 HYF 63 
HYF H143 3H14 H 0 0 N N N 12.007 82.798 -1.496 -1.699 -1.272 5.825  H143 HYF 64 
HYF H161 1H16 H 0 0 N N N 10.222 81.015 0.620  1.829  -0.327 4.031  H161 HYF 65 
HYF H171 1H17 H 0 0 N N N 12.494 78.908 1.259  -0.459 -2.376 3.572  H171 HYF 66 
HYF H172 2H17 H 0 0 N N N 11.047 79.067 2.215  1.228  -2.752 3.152  H172 HYF 67 
HYF H211 1H21 H 0 0 N N N 9.365  72.946 -0.106 -0.295 2.902  -0.434 H211 HYF 68 
HYF H221 1H22 H 0 0 N N N 13.874 74.254 0.301  -4.426 3.006  -2.242 H221 HYF 69 
HYF H222 2H22 H 0 0 N N N 14.812 72.736 -0.087 -3.850 1.325  -2.156 H222 HYF 70 
HYF H223 3H22 H 0 0 N N N 14.075 73.577 -1.383 -5.150 1.876  -1.072 H223 HYF 71 
HYF H231 1H23 H 0 0 N N N 11.777 70.506 -0.939 -1.858 4.050  0.201  H231 HYF 72 
HYF H232 2H23 H 0 0 N N N 12.860 71.413 -2.097 -2.183 4.161  -1.545 H232 HYF 73 
HYF H233 3H23 H 0 0 N N N 13.597 70.572 -0.801 -3.417 4.687  -0.375 H233 HYF 74 
HYF H251 1H25 H 0 0 N N N 10.908 71.769 0.386  -3.319 0.766  0.462  H251 HYF 75 
HYF H261 1H26 H 0 0 N N N 10.499 73.310 2.403  -1.989 2.106  2.288  H261 HYF 76 
HYF H262 2H26 H 0 0 N N N 12.014 74.079 2.192  -1.217 3.001  0.957  H262 HYF 77 
HYF H321 1H32 H 0 0 N N N 12.599 77.943 -0.901 0.587  -3.059 0.696  H321 HYF 78 
HYF H322 2H32 H 0 0 N N N 12.094 76.306 -0.764 -1.107 -2.728 1.129  H322 HYF 79 
HYF H331 1H33 H 0 0 N N N 10.578 78.437 -2.631 -0.728 -2.252 -1.258 H331 HYF 80 
HYF H351 1H35 H 0 0 N N N 10.155 75.591 -4.083 0.046  0.570  -2.237 H351 HYF 81 
HYF H352 2H35 H 0 0 N N N 10.350 74.598 -2.664 1.739  0.234  -2.670 H352 HYF 82 
HYF H361 1H36 H 0 0 N N N 7.857  73.911 -2.829 1.087  -2.017 -3.477 H361 HYF 83 
HYF H362 2H36 H 0 0 N N N 7.660  74.881 -4.200 -0.606 -1.682 -3.044 H362 HYF 84 
HYF H371 1H37 H 0 0 N N N 9.119  73.271 -5.645 -0.620 0.214  -4.804 H371 HYF 85 
HYF H381 1H38 H 0 0 N N N 9.949  70.493 -2.442 1.234  -0.765 -7.830 H381 HYF 86 
HYF H382 2H38 H 0 0 N N N 10.121 72.255 -2.160 -0.485 -0.683 -7.379 H382 HYF 87 
HYF H383 3H38 H 0 0 N N N 8.526  71.578 -2.334 0.576  0.716  -7.096 H383 HYF 88 
HYF H391 1H39 H 0 0 N N N 10.411 70.041 -4.932 2.170  -2.033 -4.489 H391 HYF 89 
HYF H392 2H39 H 0 0 N N N 9.224  70.893 -6.003 1.842  -2.763 -6.079 H392 HYF 90 
HYF H393 3H39 H 0 0 N N N 10.804 71.563 -5.833 2.930  -1.360 -5.952 H393 HYF 91 
# 
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 
HYF C1  C37  DOUB N N 1  
HYF C1  C38  SING N N 2  
HYF C1  C39  SING N N 3  
HYF C2  C10  SING N N 4  
HYF C2  H021 SING N N 5  
HYF C2  H022 SING N N 6  
HYF C2  H023 SING N N 7  
HYF C3  C10  SING N N 8  
HYF C3  H031 SING N N 9  
HYF C3  H032 SING N N 10 
HYF C3  H033 SING N N 11 
HYF C4  C5   SING N N 12 
HYF C4  H041 SING N N 13 
HYF C4  H042 SING N N 14 
HYF C4  H043 SING N N 15 
HYF C5  C6   SING N N 16 
HYF C5  C7   SING N N 17 
HYF C5  H051 SING N N 18 
HYF C6  H061 SING N N 19 
HYF C6  H062 SING N N 20 
HYF C6  H063 SING N N 21 
HYF C7  O8   DOUB N N 22 
HYF C7  C27  SING N N 23 
HYF C9  C10  DOUB N N 24 
HYF C9  C11  SING N N 25 
HYF C9  H091 SING N N 26 
HYF C11 C33  SING N N 27 
HYF C11 H111 SING N N 28 
HYF C11 H112 SING N N 29 
HYF C12 C34  SING N N 30 
HYF C12 H121 SING N N 31 
HYF C12 H122 SING N N 32 
HYF C12 H123 SING N N 33 
HYF C13 C15  SING N N 34 
HYF C13 H131 SING N N 35 
HYF C13 H132 SING N N 36 
HYF C13 H133 SING N N 37 
HYF C14 C15  SING N N 38 
HYF C14 H141 SING N N 39 
HYF C14 H142 SING N N 40 
HYF C14 H143 SING N N 41 
HYF C15 C16  DOUB N N 42 
HYF C16 C17  SING N N 43 
HYF C16 H161 SING N N 44 
HYF C17 C31  SING N N 45 
HYF C17 H171 SING N N 46 
HYF C17 H172 SING N N 47 
HYF C18 O19  DOUB N N 48 
HYF C18 C27  SING N N 49 
HYF C18 C31  SING N N 50 
HYF O20 C30  DOUB N N 51 
HYF O21 C28  SING N N 52 
HYF O21 H211 SING N N 53 
HYF C22 C24  SING N N 54 
HYF C22 H221 SING N N 55 
HYF C22 H222 SING N N 56 
HYF C22 H223 SING N N 57 
HYF C23 C24  SING N N 58 
HYF C23 H231 SING N N 59 
HYF C23 H232 SING N N 60 
HYF C23 H233 SING N N 61 
HYF C24 C25  DOUB N N 62 
HYF C25 C26  SING N N 63 
HYF C25 H251 SING N N 64 
HYF C26 C29  SING N N 65 
HYF C26 H261 SING N N 66 
HYF C26 H262 SING N N 67 
HYF C27 C28  SING N N 68 
HYF C27 C34  SING N N 69 
HYF C28 C29  DOUB N N 70 
HYF C29 C30  SING N N 71 
HYF C30 C31  SING N N 72 
HYF C31 C32  SING N N 73 
HYF C32 C33  SING N N 74 
HYF C32 H321 SING N N 75 
HYF C32 H322 SING N N 76 
HYF C33 C34  SING N N 77 
HYF C33 H331 SING N N 78 
HYF C34 C35  SING N N 79 
HYF C35 C36  SING N N 80 
HYF C35 H351 SING N N 81 
HYF C35 H352 SING N N 82 
HYF C36 C37  SING N N 83 
HYF C36 H361 SING N N 84 
HYF C36 H362 SING N N 85 
HYF C37 H371 SING N N 86 
HYF C38 H381 SING N N 87 
HYF C38 H382 SING N N 88 
HYF C38 H383 SING N N 89 
HYF C39 H391 SING N N 90 
HYF C39 H392 SING N N 91 
HYF C39 H393 SING N N 92 
# 
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 
HYF SMILES           ACDLabs              10.04 O=C1C2(C(O)=C(C(=O)C1(CC(C\C=C(/C)C)C2(C)CC\C=C(/C)C)C\C=C(/C)C)C\C=C(/C)C)C(=O)C(C)C                                                                                                                  
HYF InChI            InChI                1.02b InChI=1/C35H52O4/c1-22(2)13-12-19-33(11)27(16-14-23(3)4)21-34(20-18-25(7)8)30(37)28(17-15-24(5)6)31(38)35(33,32(34)39)29(36)26(9)10/h13-15,18,26-27,38H,12,16-17,19-21H2,1-11H3/t27-,33-,34-,35+/m1/s1 
HYF InChIKey         InChI                1.02b IWBJJCOKGLUQIZ-OJCNYLSABM                                                                                                                                                                              
HYF SMILES_CANONICAL CACTVS               3.341 CC(C)C(=O)[C@@]12C(=C(CC=C(C)C)C(=O)[C@@](CC=C(C)C)(C[C@@H](CC=C(C)C)[C@@]1(C)CCC=C(C)C)C2=O)O                                                                                                         
HYF SMILES           CACTVS               3.341 CC(C)C(=O)[C]12C(=C(CC=C(C)C)C(=O)[C](CC=C(C)C)(C[CH](CC=C(C)C)[C]1(C)CCC=C(C)C)C2=O)O                                                                                                                 
HYF SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(C)C(=O)[C@]12C(=C(C(=O)[C@](C1=O)(C[C@H]([C@@]2(C)CCC=C(C)C)CC=C(C)C)CC=C(C)C)CC=C(C)C)O                                                                                                            
HYF SMILES           "OpenEye OEToolkits" 1.5.0 CC(C)C(=O)C12C(=C(C(=O)C(C1=O)(CC(C2(C)CCC=C(C)C)CC=C(C)C)CC=C(C)C)CC=C(C)C)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 
HYF "SYSTEMATIC NAME" ACDLabs              10.04 (1R,5S,6R,7R)-4-hydroxy-6-methyl-1,3,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)-5-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione 
HYF "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (1S,2R,3R,5R)-8-hydroxy-2-methyl-3,5,7-tris(3-methylbut-2-enyl)-2-(4-methylpent-3-enyl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-7-ene-6,9-dione       
# 
