data_FUG
# 
_chem_comp.id                                    FUG 
_chem_comp.name                                  FUMAGILLIN 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C26 H36 O7" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-03-28 
_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                        460.560 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     FUG 
_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        1BOA 
_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 
FUG C5   C5   C 0 1 N N N 18.042 27.771 21.034 -1.539 2.163  1.730  C5   FUG 1  
FUG C4   C4   C 0 1 N N R 16.591 28.245 20.979 -1.212 1.987  0.246  C4   FUG 2  
FUG C3   C3   C 0 1 N N S 16.191 28.765 19.592 -2.507 1.775  -0.541 C3   FUG 3  
FUG C2   C2   C 0 1 N N S 17.175 29.867 19.093 -3.219 0.524  -0.023 C2   FUG 4  
FUG C1   C1   C 0 1 N N R 18.609 29.346 19.055 -3.547 0.700  1.461  C1   FUG 5  
FUG C6   C6   C 0 1 N N N 18.969 28.837 20.457 -2.251 0.911  2.247  C6   FUG 6  
FUG O11  O11  O 0 1 N N N 18.630 28.288 18.199 -4.397 1.836  1.630  O11  FUG 7  
FUG C11  C11  C 0 1 N N N 19.668 30.350 18.603 -4.259 -0.552 1.978  C11  FUG 8  
FUG C21  C21  C 0 1 N N R 16.632 30.588 17.821 -4.515 0.312  -0.810 C21  FUG 9  
FUG C22  C22  C 0 1 N N R 16.741 32.017 17.450 -5.112 -1.096 -0.833 C22  FUG 10 
FUG C23  C23  C 0 1 N N N 16.989 32.497 16.046 -6.637 -1.224 -0.875 C23  FUG 11 
FUG C24  C24  C 0 1 N N N 18.405 32.237 15.589 -7.019 -2.681 -0.834 C24  FUG 12 
FUG C25  C25  C 0 1 N N N 19.563 32.895 15.628 -7.843 -3.117 0.088  C25  FUG 13 
FUG C2A  C2A  C 0 1 N N N 16.392 29.527 16.748 -5.482 1.498  -0.827 C2A  FUG 14 
FUG O2A  O2A  O 0 1 N N N 15.506 31.484 17.948 -4.461 -0.520 -1.970 O2A  FUG 15 
FUG C2B  C2B  C 0 1 N N N 20.904 32.300 15.260 -8.407 -2.160 1.107  C2B  FUG 16 
FUG C2C  C2C  C 0 1 N N N 19.755 34.245 16.311 -8.225 -4.574 0.129  C2C  FUG 17 
FUG O31  O31  O 0 1 N N N 14.846 29.247 19.555 -2.202 1.611  -1.927 O31  FUG 18 
FUG C31  C31  C 0 1 N N N 13.818 28.235 19.656 -2.222 2.915  -2.512 C31  FUG 19 
FUG O41  O41  O 0 1 N N N 16.416 29.373 21.881 -0.362 0.851  0.077  O41  FUG 20 
FUG C41  C41  C 0 1 N N N 15.413 29.590 22.757 0.909  1.297  0.170  C41  FUG 21 
FUG O4A  O4A  O 0 1 N N N 14.718 28.641 22.982 1.125  2.479  0.364  O4A  FUG 22 
FUG C42  C42  C 0 1 N N N 15.234 30.876 23.472 1.990  0.390  0.042  C42  FUG 23 
FUG C43  C43  C 0 1 N N N 14.860 31.022 24.760 3.269  0.839  0.136  C43  FUG 24 
FUG C44  C44  C 0 1 N N N 15.227 32.248 25.499 4.344  -0.063 0.008  C44  FUG 25 
FUG C45  C45  C 0 1 N N N 14.922 32.477 26.783 5.625  0.387  0.102  C45  FUG 26 
FUG C46  C46  C 0 1 N N N 15.300 33.699 27.490 6.700  -0.515 -0.025 C46  FUG 27 
FUG C47  C47  C 0 1 N N N 14.999 33.951 28.774 7.981  -0.065 0.069  C47  FUG 28 
FUG C48  C48  C 0 1 N N N 15.394 35.193 29.447 9.056  -0.968 -0.058 C48  FUG 29 
FUG C49  C49  C 0 1 N N N 15.091 35.473 30.738 10.335 -0.518 0.035  C49  FUG 30 
FUG C4A  C4A  C 0 1 N N N 15.764 36.656 31.344 11.416 -1.426 -0.093 C4A  FUG 31 
FUG O4B  O4B  O 0 1 N N N 15.296 37.020 32.420 12.686 -0.979 0.000  O4B  FUG 32 
FUG O4C  O4C  O 0 1 N N N 16.659 37.261 30.741 11.199 -2.607 -0.287 O4C  FUG 33 
FUG H51  1H5  H 0 1 N N N 18.141 26.850 20.440 -0.617 2.314  2.290  H51  FUG 34 
FUG H52  2H5  H 0 1 N N N 18.320 27.578 22.081 -2.188 3.029  1.859  H52  FUG 35 
FUG H4   H4   H 0 1 N N N 15.975 27.374 21.248 -0.705 2.878  -0.123 H4   FUG 36 
FUG H3   H3   H 0 1 N N N 16.251 27.904 18.910 -3.156 2.642  -0.412 H3   FUG 37 
FUG H2   H2   H 0 1 N N N 17.230 30.688 19.823 -2.571 -0.343 -0.152 H2   FUG 38 
FUG H61  1H6  H 0 1 N N N 19.956 28.361 20.362 -1.603 0.045  2.118  H61  FUG 39 
FUG H62  2H6  H 0 1 N N N 18.942 29.701 21.138 -2.485 1.037  3.304  H62  FUG 40 
FUG HOB  HOB  H 0 1 N N N 18.635 28.605 17.303 -4.579 1.911  2.576  HOB  FUG 41 
FUG H111 1H11 H 0 0 N N N 20.668 29.914 18.740 -4.360 -0.491 3.062  H111 FUG 42 
FUG H112 2H11 H 0 0 N N N 19.583 31.268 19.203 -5.247 -0.621 1.524  H112 FUG 43 
FUG H113 3H11 H 0 0 N N N 19.515 30.591 17.541 -3.676 -1.435 1.717  H113 FUG 44 
FUG H22  H22  H 0 1 N N N 17.383 32.865 17.730 -4.586 -1.880 -0.290 H22  FUG 45 
FUG H231 1H23 H 0 0 N N N 16.824 33.584 16.028 -7.068 -0.711 -0.015 H231 FUG 46 
FUG H232 2H23 H 0 0 N N N 16.302 31.968 15.370 -7.014 -0.775 -1.793 H232 FUG 47 
FUG H24  H24  H 0 1 N N N 18.504 31.274 15.109 -6.615 -3.366 -1.564 H24  FUG 48 
FUG H2A1 1H2A H 0 0 N N N 15.447 29.003 16.956 -4.950 2.396  -1.141 H2A1 FUG 49 
FUG H2A2 2H2A H 0 0 N N N 17.221 28.805 16.755 -6.294 1.294  -1.525 H2A2 FUG 50 
FUG H2A3 3H2A H 0 0 N N N 16.334 30.009 15.761 -5.891 1.648  0.172  H2A3 FUG 51 
FUG H2B1 1H2B H 0 0 N N N 21.025 31.330 15.764 -8.971 -1.378 0.598  H2B1 FUG 52 
FUG H2B2 2H2B H 0 0 N N N 21.707 32.982 15.577 -9.067 -2.701 1.786  H2B2 FUG 53 
FUG H2B3 3H2B H 0 0 N N N 20.955 32.156 14.171 -7.592 -1.710 1.673  H2B3 FUG 54 
FUG H2C1 1H2C H 0 0 N N N 18.910 34.904 16.064 -7.722 -5.104 -0.680 H2C1 FUG 55 
FUG H2C2 2H2C H 0 0 N N N 20.692 34.703 15.961 -7.926 -5.001 1.085  H2C2 FUG 56 
FUG H2C3 3H2C H 0 0 N N N 19.801 34.102 17.401 -9.305 -4.669 0.010  H2C3 FUG 57 
FUG H311 1H31 H 0 0 N N N 14.133 27.337 19.104 -1.993 2.839  -3.575 H311 FUG 58 
FUG H312 2H31 H 0 0 N N N 12.881 28.620 19.227 -3.211 3.355  -2.383 H312 FUG 59 
FUG H313 3H31 H 0 0 N N N 13.658 27.978 20.714 -1.478 3.544  -2.023 H313 FUG 60 
FUG H42  H42  H 0 1 N N N 15.420 31.779 22.910 1.798  -0.659 -0.130 H42  FUG 61 
FUG H43  H43  H 0 1 N N N 14.293 30.244 25.250 3.461  1.888  0.308  H43  FUG 62 
FUG H44  H44  H 0 1 N N N 15.778 33.010 24.968 4.152  -1.112 -0.164 H44  FUG 63 
FUG H45  H45  H 0 1 N N N 14.370 31.722 27.322 5.817  1.435  0.274  H45  FUG 64 
FUG H46  H46  H 0 1 N N N 15.857 34.447 26.945 6.507  -1.564 -0.197 H46  FUG 65 
FUG H47  H47  H 0 1 N N N 14.445 33.211 29.333 8.173  0.984  0.241  H47  FUG 66 
FUG H48  H48  H 0 1 N N N 15.956 35.923 28.884 8.864  -2.016 -0.231 H48  FUG 67 
FUG H49  H49  H 0 1 N N N 14.395 34.868 31.300 10.527 0.530  0.207  H49  FUG 68 
FUG HOB4 4HOB H 0 0 N N N 15.726 37.820 32.699 13.262 -1.748 -0.114 HOB4 FUG 69 
# 
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 
FUG C5  C4   SING N N 1  
FUG C5  C6   SING N N 2  
FUG C5  H51  SING N N 3  
FUG C5  H52  SING N N 4  
FUG C4  C3   SING N N 5  
FUG C4  O41  SING N N 6  
FUG C4  H4   SING N N 7  
FUG C3  C2   SING N N 8  
FUG C3  O31  SING N N 9  
FUG C3  H3   SING N N 10 
FUG C2  C1   SING N N 11 
FUG C2  C21  SING N N 12 
FUG C2  H2   SING N N 13 
FUG C1  C6   SING N N 14 
FUG C1  O11  SING N N 15 
FUG C1  C11  SING N N 16 
FUG C6  H61  SING N N 17 
FUG C6  H62  SING N N 18 
FUG O11 HOB  SING N N 19 
FUG C11 H111 SING N N 20 
FUG C11 H112 SING N N 21 
FUG C11 H113 SING N N 22 
FUG C21 C22  SING N N 23 
FUG C21 C2A  SING N N 24 
FUG C21 O2A  SING N N 25 
FUG C22 C23  SING N N 26 
FUG C22 O2A  SING N N 27 
FUG C22 H22  SING N N 28 
FUG C23 C24  SING N N 29 
FUG C23 H231 SING N N 30 
FUG C23 H232 SING N N 31 
FUG C24 C25  DOUB N N 32 
FUG C24 H24  SING N N 33 
FUG C25 C2B  SING N N 34 
FUG C25 C2C  SING N N 35 
FUG C2A H2A1 SING N N 36 
FUG C2A H2A2 SING N N 37 
FUG C2A H2A3 SING N N 38 
FUG C2B H2B1 SING N N 39 
FUG C2B H2B2 SING N N 40 
FUG C2B H2B3 SING N N 41 
FUG C2C H2C1 SING N N 42 
FUG C2C H2C2 SING N N 43 
FUG C2C H2C3 SING N N 44 
FUG O31 C31  SING N N 45 
FUG C31 H311 SING N N 46 
FUG C31 H312 SING N N 47 
FUG C31 H313 SING N N 48 
FUG O41 C41  SING N N 49 
FUG C41 O4A  DOUB N N 50 
FUG C41 C42  SING N N 51 
FUG C42 C43  DOUB N E 52 
FUG C42 H42  SING N N 53 
FUG C43 C44  SING N N 54 
FUG C43 H43  SING N N 55 
FUG C44 C45  DOUB N E 56 
FUG C44 H44  SING N N 57 
FUG C45 C46  SING N N 58 
FUG C45 H45  SING N N 59 
FUG C46 C47  DOUB N E 60 
FUG C46 H46  SING N N 61 
FUG C47 C48  SING N N 62 
FUG C47 H47  SING N N 63 
FUG C48 C49  DOUB N E 64 
FUG C48 H48  SING N N 65 
FUG C49 C4A  SING N N 66 
FUG C49 H49  SING N N 67 
FUG C4A O4B  SING N N 68 
FUG C4A O4C  DOUB N N 69 
FUG O4B HOB4 SING N N 70 
# 
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 
FUG SMILES           ACDLabs              10.04 O=C(O)\C=C\C=C\C=C\C=C\C(=O)OC2CCC(O)(C(C1(OC1C/C=C(/C)C)C)C2OC)C 
FUG InChI            InChI                1.02b 
InChI=1/C26H36O7/c1-18(2)14-15-20-26(4,33-20)24-23(31-5)19(16-17-25(24,3)30)32-22(29)13-11-9-7-6-8-10-12-21(27)28/h6-14,19-20,23-24,30H,15-17H2,1-5H3,(H,27,28)/b8-6+,9-7+,12-10+,13-11+/t19-,20-,23-,24+,25-,26+/m1/s1/f/h27H 
FUG InChIKey         InChI                1.02b XXVWUXWNPOXVQB-SXVZXKHTDV 
FUG SMILES_CANONICAL CACTVS               3.341 CO[C@@H]1[C@@H](CC[C@@](C)(O)[C@H]1[C@@]2(C)O[C@@H]2CC=C(C)C)OC(=O)\C=C\C=C\C=C\C=C\C(O)=O 
FUG SMILES           CACTVS               3.341 CO[CH]1[CH](CC[C](C)(O)[CH]1[C]2(C)O[CH]2CC=C(C)C)OC(=O)C=CC=CC=CC=CC(O)=O 
FUG SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(=CC[C@@H]1[C@@](O1)(C)[C@H]2[C@@H]([C@@H](CC[C@@]2(C)O)OC(=O)C=C\C=C\C=C\C=C\C(=O)O)OC)C 
FUG SMILES           "OpenEye OEToolkits" 1.5.0 CC(=CCC1C(O1)(C)C2C(C(CCC2(C)O)OC(=O)C=CC=CC=CC=CC(=O)O)OC)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 
FUG "SYSTEMATIC NAME" ACDLabs              10.04 "(2E,4E,6E,8E)-10-({(1R,2S,3S,4R)-4-hydroxy-2-methoxy-4-methyl-3-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]cyclohexyl}oxy)-10-oxodeca-2,4,6,8-tetraenoic acid" 
FUG "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2E,4E,6E)-10-[(1R,2S,3S,4R)-4-hydroxy-2-methoxy-4-methyl-3-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]cyclohexyl]oxy-10-oxo-deca-2,4,6,8-tetraenoic acid"        
# 
