data_EPB
# 
_chem_comp.id                                    EPB 
_chem_comp.name                                  7,11-DIHYDROXY-8,8,10,12,16-PENTAMETHYL-3-[1-METHYL-2-(2-METHYL-THIAZOL-4-YL)VINYL]-4,17-DIOXABICYCLO[14.1.0]HEPTADECANE-5,9-DIONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C27 H41 N O6 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "EPOTHILONE B" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-08-07 
_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                        507.683 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     EPB 
_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        1Q5D 
_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 
EPB O16  O16  O 0 1 N N N 5.694  36.704 14.402 -1.221 -0.291 -0.924 O16  EPB 1  
EPB C51  C51  C 0 1 N N N 9.565  39.175 15.858 5.103  1.179  1.286  C51  EPB 2  
EPB O41  O41  O 0 1 N N N 8.617  38.517 18.283 4.232  -0.094 -0.706 O41  EPB 3  
EPB C5   C5   C 0 1 N N R 8.657  39.193 17.033 4.037  0.268  0.667  C5   EPB 4  
EPB C4   C4   C 0 1 N N S 7.493  38.152 17.473 3.182  0.841  -0.457 C4   EPB 5  
EPB C16  C16  C 0 1 N N N 5.308  37.812 14.463 -1.207 0.810  -0.439 C16  EPB 6  
EPB O1   O1   O 0 1 N N N 4.993  38.503 15.623 -0.285 1.717  -0.769 O1   EPB 7  
EPB C2   C2   C 0 1 N N S 5.066  37.859 17.026 0.955  1.391  -1.432 C2   EPB 8  
EPB C3   C3   C 0 1 N N N 6.186  38.614 17.846 1.741  0.357  -0.624 C3   EPB 9  
EPB C20  C20  C 0 1 N N N 3.608  38.125 17.581 0.702  0.871  -2.822 C20  EPB 10 
EPB C21  C21  C 0 1 N N N 2.579  37.257 16.873 1.861  0.493  -3.708 C21  EPB 11 
EPB C22  C22  C 0 1 N N N 3.338  39.013 18.581 -0.540 0.745  -3.267 C22  EPB 12 
EPB C23  C23  C 0 1 Y N N 2.090  39.443 19.213 -0.792 0.158  -4.599 C23  EPB 13 
EPB N26  N26  N 0 1 Y N N 0.943  39.527 18.443 0.195  -0.352 -5.320 N26  EPB 14 
EPB C25  C25  C 0 1 Y N N -0.112 39.962 19.179 -0.020 -0.879 -6.500 C25  EPB 15 
EPB C27  C27  C 0 1 N N N -1.435 40.093 18.531 0.969  -1.503 -7.449 C27  EPB 16 
EPB C24  C24  C 0 1 Y N N 1.922  39.839 20.486 -2.055 0.128  -5.133 C24  EPB 17 
EPB S1   S1   S 0 1 Y N N 0.296  40.296 20.766 -1.732 -0.670 -6.698 S1   EPB 18 
EPB C15  C15  C 0 1 N N N 5.105  38.646 13.172 -2.242 1.167  0.615  C15  EPB 19 
EPB C14  C14  C 0 1 N N S 3.764  39.507 13.111 -2.368 -0.010 1.578  C14  EPB 20 
EPB O14  O14  O 0 1 N N N 2.753  38.553 13.390 -3.104 -1.061 0.919  O14  EPB 21 
EPB C13  C13  C 0 1 N N N 3.529  40.391 11.764 -3.086 0.333  2.872  C13  EPB 22 
EPB C29  C29  C 0 1 N N N 3.415  39.410 10.545 -3.522 1.796  2.941  C29  EPB 23 
EPB C30  C30  C 0 1 N N N 2.179  41.100 11.839 -4.377 -0.524 2.916  C30  EPB 24 
EPB C12  C12  C 0 1 N N N 4.772  41.407 11.475 -2.283 -0.035 4.087  C12  EPB 25 
EPB O12  O12  O 0 1 N N N 5.451  41.318 10.403 -2.863 -0.681 4.951  O12  EPB 26 
EPB C11  C11  C 0 1 N N R 5.251  42.552 12.451 -0.848 0.317  4.347  C11  EPB 27 
EPB C28  C28  C 0 1 N N N 5.357  43.810 11.555 -0.325 1.397  3.411  C28  EPB 28 
EPB C10  C10  C 0 1 N N S 6.305  41.970 13.345 0.022  -0.939 4.275  C10  EPB 29 
EPB O10  O10  O 0 1 N N N 7.542  41.763 12.594 0.052  -1.440 2.940  O10  EPB 30 
EPB C9   C9   C 0 1 N N S 6.508  42.963 14.472 1.439  -0.645 4.765  C9   EPB 31 
EPB C91  C91  C 0 1 N N N 5.281  43.064 15.248 1.605  -1.230 6.177  C91  EPB 32 
EPB C8   C8   C 0 1 N N N 7.469  42.542 15.529 2.485  -1.277 3.846  C8   EPB 33 
EPB C7   C7   C 0 1 N N N 8.053  41.076 15.397 3.128  -0.204 2.964  C7   EPB 34 
EPB C6   C6   C 0 1 N N N 7.614  40.490 16.843 3.447  -0.796 1.589  C6   EPB 35 
EPB H511 1H51 H 0 0 N N N 9.596  39.705 14.877 5.693  0.611  2.005  H511 EPB 36 
EPB H512 2H51 H 0 0 N N N 10.565 39.388 16.300 5.756  1.561  0.501  H512 EPB 37 
EPB H513 3H51 H 0 0 N N N 9.597  38.097 15.571 4.618  2.013  1.793  H513 EPB 38 
EPB H4   H4   H 0 1 N N N 7.042  37.223 17.050 3.360  1.883  -0.743 H4   EPB 39 
EPB H3   H3   H 0 1 N N N 5.330  36.776 17.064 1.564  2.301  -1.511 H3   EPB 40 
EPB H31  1H3  H 0 1 N N N 6.018  38.531 18.945 1.742  -0.594 -1.158 H31  EPB 41 
EPB H32  2H3  H 0 1 N N N 6.095  39.720 17.744 1.278  0.229  0.352  H32  EPB 42 
EPB H211 1H21 H 0 0 N N N 1.551  37.444 17.264 2.796  0.754  -3.213 H211 EPB 43 
EPB H212 2H21 H 0 0 N N N 2.625  37.387 15.766 1.838  -0.579 -3.898 H212 EPB 44 
EPB H213 3H21 H 0 0 N N N 2.847  36.176 16.929 1.787  1.032  -4.652 H213 EPB 45 
EPB H22  H22  H 0 1 N N N 4.283  39.455 18.936 -1.369 1.072  -2.656 H22  EPB 46 
EPB H271 1H27 H 0 0 N N N -2.301 40.450 19.135 0.450  -1.837 -8.348 H271 EPB 47 
EPB H272 2H27 H 0 0 N N N -1.331 40.745 17.632 1.727  -0.768 -7.719 H272 EPB 48 
EPB H273 3H27 H 0 0 N N N -1.702 39.117 18.062 1.447  -2.356 -6.967 H273 EPB 49 
EPB H24  H24  H 0 1 N N N 2.833  39.800 21.106 -2.987 0.488  -4.721 H24  EPB 50 
EPB H151 1H15 H 0 0 N N N 5.988  39.304 13.001 -1.883 2.062  1.113  H151 EPB 51 
EPB H152 2H15 H 0 0 N N N 5.174  37.985 12.276 -3.191 1.354  0.120  H152 EPB 52 
EPB H14  H14  H 0 1 N N N 3.784  40.342 13.849 -1.371 -0.397 1.781  H14  EPB 53 
EPB H2   H2   H 0 1 N N N 1.954  39.065 13.353 -2.599 -1.305 0.131  H2   EPB 54 
EPB H291 1H29 H 0 0 N N N 3.254  40.015 9.622  -4.029 1.980  3.888  H291 EPB 55 
EPB H292 2H29 H 0 0 N N N 4.290  38.725 10.461 -2.645 2.440  2.867  H292 EPB 56 
EPB H293 3H29 H 0 0 N N N 2.628  38.633 10.691 -4.202 2.013  2.117  H293 EPB 57 
EPB H301 1H30 H 0 0 N N N 2.018  41.705 10.916 -4.926 -0.308 3.833  H301 EPB 58 
EPB H302 2H30 H 0 0 N N N 1.341  40.387 12.024 -5.001 -0.287 2.055  H302 EPB 59 
EPB H303 3H30 H 0 0 N N N 2.078  41.712 12.765 -4.112 -1.581 2.892  H303 EPB 60 
EPB H11  H11  H 0 1 N N N 4.613  42.961 13.269 -0.782 0.701  5.380  H11  EPB 61 
EPB H281 1H28 H 0 0 N N N 5.695  44.618 12.244 -0.918 2.303  3.534  H281 EPB 62 
EPB H282 2H28 H 0 0 N N N 6.006  43.675 10.658 0.716  1.610  3.648  H282 EPB 63 
EPB H283 3H28 H 0 0 N N N 4.422  44.050 10.997 -0.400 1.051  2.380  H283 EPB 64 
EPB H1   H1   H 0 1 N N N 5.999  40.976 13.748 -0.418 -1.705 4.925  H1   EPB 65 
EPB H10  H10  H 0 1 N N N 8.209  41.394 13.160 0.500  -0.774 2.402  H10  EPB 66 
EPB H9   H9   H 0 1 N N N 6.858  43.880 13.944 1.613  0.429  4.821  H9   EPB 67 
EPB H911 1H91 H 0 0 N N N 5.430  43.794 16.077 2.614  -1.031 6.537  H911 EPB 68 
EPB H912 2H91 H 0 0 N N N 4.399  43.317 14.614 0.882  -0.767 6.849  H912 EPB 69 
EPB H913 3H91 H 0 0 N N N 4.930  42.071 15.616 1.435  -2.306 6.147  H913 EPB 70 
EPB H81  1H8  H 0 1 N N N 8.305  43.277 15.593 3.272  -1.719 4.472  H81  EPB 71 
EPB H82  2H8  H 0 1 N N N 7.006  42.674 16.534 2.062  -2.064 3.235  H82  EPB 72 
EPB H71  1H7  H 0 1 N N N 7.718  40.492 14.507 2.441  0.631  2.849  H71  EPB 73 
EPB H72  2H7  H 0 1 N N N 9.136  40.999 15.143 4.046  0.135  3.445  H72  EPB 74 
EPB H61  1H6  H 0 1 N N N 6.531  40.241 16.940 4.169  -1.608 1.710  H61  EPB 75 
EPB H62  2H6  H 0 1 N N N 7.629  41.231 17.675 2.536  -1.202 1.150  H62  EPB 76 
# 
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 
EPB O16 C16  DOUB N N 1  
EPB C51 C5   SING N N 2  
EPB C51 H511 SING N N 3  
EPB C51 H512 SING N N 4  
EPB C51 H513 SING N N 5  
EPB O41 C5   SING N N 6  
EPB O41 C4   SING N N 7  
EPB C5  C4   SING N N 8  
EPB C5  C6   SING N N 9  
EPB C4  C3   SING N N 10 
EPB C4  H4   SING N N 11 
EPB C16 O1   SING N N 12 
EPB C16 C15  SING N N 13 
EPB O1  C2   SING N N 14 
EPB C2  C3   SING N N 15 
EPB C2  C20  SING N N 16 
EPB C2  H3   SING N N 17 
EPB C3  H31  SING N N 18 
EPB C3  H32  SING N N 19 
EPB C20 C21  SING N N 20 
EPB C20 C22  DOUB N E 21 
EPB C21 H211 SING N N 22 
EPB C21 H212 SING N N 23 
EPB C21 H213 SING N N 24 
EPB C22 C23  SING N N 25 
EPB C22 H22  SING N N 26 
EPB C23 N26  SING Y N 27 
EPB C23 C24  DOUB Y N 28 
EPB N26 C25  DOUB Y N 29 
EPB C25 C27  SING N N 30 
EPB C25 S1   SING Y N 31 
EPB C27 H271 SING N N 32 
EPB C27 H272 SING N N 33 
EPB C27 H273 SING N N 34 
EPB C24 S1   SING Y N 35 
EPB C24 H24  SING N N 36 
EPB C15 C14  SING N N 37 
EPB C15 H151 SING N N 38 
EPB C15 H152 SING N N 39 
EPB C14 O14  SING N N 40 
EPB C14 C13  SING N N 41 
EPB C14 H14  SING N N 42 
EPB O14 H2   SING N N 43 
EPB C13 C29  SING N N 44 
EPB C13 C30  SING N N 45 
EPB C13 C12  SING N N 46 
EPB C29 H291 SING N N 47 
EPB C29 H292 SING N N 48 
EPB C29 H293 SING N N 49 
EPB C30 H301 SING N N 50 
EPB C30 H302 SING N N 51 
EPB C30 H303 SING N N 52 
EPB C12 O12  DOUB N N 53 
EPB C12 C11  SING N N 54 
EPB C11 C28  SING N N 55 
EPB C11 C10  SING N N 56 
EPB C11 H11  SING N N 57 
EPB C28 H281 SING N N 58 
EPB C28 H282 SING N N 59 
EPB C28 H283 SING N N 60 
EPB C10 O10  SING N N 61 
EPB C10 C9   SING N N 62 
EPB C10 H1   SING N N 63 
EPB O10 H10  SING N N 64 
EPB C9  C91  SING N N 65 
EPB C9  C8   SING N N 66 
EPB C9  H9   SING N N 67 
EPB C91 H911 SING N N 68 
EPB C91 H912 SING N N 69 
EPB C91 H913 SING N N 70 
EPB C8  C7   SING N N 71 
EPB C8  H81  SING N N 72 
EPB C8  H82  SING N N 73 
EPB C7  C6   SING N N 74 
EPB C7  H71  SING N N 75 
EPB C7  H72  SING N N 76 
EPB C6  H61  SING N N 77 
EPB C6  H62  SING N N 78 
# 
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 
EPB SMILES           ACDLabs              10.04 O=C1C(C)C(O)C(C)CCCC3(OC3CC(OC(=O)CC(O)C1(C)C)/C(=C/c2nc(sc2)C)C)C 
EPB InChI            InChI                1.02b 
InChI=1/C27H41NO6S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)33-23(30)13-21(29)26(5,6)25(32)17(3)24(15)31/h11,14-15,17,20-22,24,29,31H,8-10,12-13H2,1-7H3/b16-11+/t15-,17+,20-,21-,22-,24-,27+/m0/s1 
EPB InChIKey         InChI                1.02b QXRSDHAAWVKZLJ-PVYNADRNBK 
EPB SMILES_CANONICAL CACTVS               3.341 C[C@H]1CCC[C@@]2(C)O[C@H]2C[C@H](OC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@H]1O)\C(C)=C\c3csc(C)n3 
EPB SMILES           CACTVS               3.341 C[CH]1CCC[C]2(C)O[CH]2C[CH](OC(=O)C[CH](O)C(C)(C)C(=O)[CH](C)[CH]1O)C(C)=Cc3csc(C)n3 
EPB SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1nc(cs1)\C=C(/C)\[C@@H]2C[C@H]3[C@](O3)(CCC[C@@H]([C@@H]([C@H](C(=O)C([C@H](CC(=O)O2)O)(C)C)C)O)C)C 
EPB SMILES           "OpenEye OEToolkits" 1.5.0 Cc1nc(cs1)C=C(C)C2CC3C(O3)(CCCC(C(C(C(=O)C(C(CC(=O)O2)O)(C)C)C)O)C)C 
# 
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 
EPB "SYSTEMATIC NAME" ACDLabs              10.04 (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione 
EPB "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (1R,5S,6S,7R,10S,14S,16S)-6,10-dihydroxy-1,5,7,9,9-pentamethyl-14-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-13,17-dioxabicyclo[14.1.0]heptadecane-8,12-dione    
# 
