data_BC2
# 
_chem_comp.id                                    BC2 
_chem_comp.name                                  MACBECIN 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             ? 
_chem_comp.formula                               "C30 H42 N2 O8" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-01-16 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        558.663 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     BC2 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        2VLS 
_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 
BC2 O23  O23  O 0 1 N N N -26.408 34.456 -3.517  2.266  0.680  -0.902 O23  BC2 1  
BC2 C2   C2   C 0 1 N N N -25.853 33.583 -4.238  3.359  0.674  -0.331 C2   BC2 2  
BC2 C3   C3   C 0 1 N N N -25.366 32.409 -3.622  3.933  1.908  0.195  C3   BC2 3  
BC2 C4   C4   C 0 1 N N N -24.773 31.452 -4.447  5.122  1.900  0.776  C4   BC2 4  
BC2 C5   C5   C 0 1 N N N -24.601 31.662 -5.845  5.860  0.603  0.898  C5   BC2 5  
BC2 O24  O24  O 0 1 N N N -24.030 30.757 -6.545  6.949  0.645  1.421  O24  BC2 6  
BC2 C6   C6   C 0 1 N N N -25.058 32.862 -6.436  5.235  -0.646 0.582  C6   BC2 7  
BC2 N22  N22  N 0 1 N N N -25.512 32.166 -2.267  3.200  3.120  0.053  N22  BC2 8  
BC2 C21  C21  C 0 1 N N N -25.085 32.958 -1.223  1.963  3.086  -0.348 C21  BC2 9  
BC2 O37  O37  O 0 1 N N N -25.211 32.617 -0.036  1.650  2.767  -1.441 O37  BC2 10 
BC2 C20  C20  C 0 1 N N N -24.512 34.182 -1.379  0.832  3.569  0.459  C20  BC2 11 
BC2 C36  C36  C 0 1 N N N -24.936 35.406 -0.564  1.107  4.228  1.779  C36  BC2 12 
BC2 C19  C19  C 0 1 N N N -23.390 34.364 -2.040  -0.386 3.246  0.004  C19  BC2 13 
BC2 C18  C18  C 0 1 N N N -22.309 35.027 -2.231  -1.611 3.701  0.800  C18  BC2 14 
BC2 C17  C17  C 0 1 N N N -21.220 35.365 -2.845  -2.804 3.133  0.560  C17  BC2 15 
BC2 C16  C16  C 0 1 N N S -20.301 34.179 -2.844  -2.985 2.003  -0.534 C16  BC2 16 
BC2 C35  C35  C 0 1 N N N -19.372 34.274 -1.620  -3.598 2.630  -1.771 C35  BC2 17 
BC2 C1   C1   C 0 1 N N N -25.678 33.835 -5.611  3.943  -0.665 -0.015 C1   BC2 18 
BC2 C7   C7   C 0 1 N N R -26.149 35.148 -6.163  3.319  -1.932 -0.495 C7   BC2 19 
BC2 O38  O38  O 0 1 N N N -26.498 34.990 -7.550  2.679  -1.748 -1.641 O38  BC2 20 
BC2 C39  C39  C 0 1 N N N -27.869 34.581 -7.714  3.493  -1.941 -2.800 C39  BC2 21 
BC2 C8   C8   C 0 1 N N S -25.077 36.270 -6.109  2.461  -2.425 0.674  C8   BC2 22 
BC2 C25  C25  C 0 1 N N N -24.509 36.643 -4.730  1.791  -1.318 1.437  C25  BC2 23 
BC2 C9   C9   C 0 1 N N N -23.929 35.945 -7.064  1.490  -3.465 0.150  C9   BC2 24 
BC2 C10  C10  C 0 1 N N S -22.645 36.764 -7.026  0.207  -2.837 -0.413 C10  BC2 25 
BC2 O26  O26  O 0 1 N N N -22.862 38.124 -7.440  0.273  -1.592 -0.875 O26  BC2 26 
BC2 C27  C27  C 0 1 N N N -21.969 39.063 -6.804  -0.034 -1.472 -2.266 C27  BC2 27 
BC2 C11  C11  C 0 1 N N R -21.627 36.222 -8.021  -0.999 -2.987 0.530  C11  BC2 28 
BC2 O28  O28  O 0 1 N N N -22.275 36.196 -9.319  -1.074 -4.324 1.126  O28  BC2 29 
BC2 C40  C40  C 0 1 N N N -21.646 37.081 -10.308 -1.032 -4.327 2.555  C40  BC2 30 
BC2 C12  C12  C 0 1 N N S -20.979 34.859 -7.678  -2.294 -2.544 -0.095 C12  BC2 31 
BC2 C29  C29  C 0 1 N N N -19.856 34.532 -8.658  -3.330 -3.644 0.249  C29  BC2 32 
BC2 C13  C13  C 0 1 N N N -20.280 34.827 -6.339  -2.708 -1.239 0.280  C13  BC2 33 
BC2 C14  C14  C 0 1 N N N -20.414 33.847 -5.416  -3.407 -0.448 -0.511 C14  BC2 34 
BC2 C30  C30  C 0 1 N N N -21.286 32.629 -5.639  -3.824 -0.823 -1.816 C30  BC2 35 
BC2 C15  C15  C 0 1 N N R -19.554 34.018 -4.194  -3.828 0.971  0.069  C15  BC2 36 
BC2 O31  O31  O 0 1 N N N -18.707 32.855 -4.073  -5.279 1.220  -0.309 O31  BC2 37 
BC2 C32  C32  C 0 1 N N N -17.508 32.705 -4.822  -6.217 0.825  0.572  C32  BC2 38 
BC2 O33  O33  O 0 1 N N N -16.903 31.653 -4.587  -5.887 0.296  1.615  O33  BC2 39 
BC2 N34  N34  N 0 1 N N N -17.101 33.654 -5.651  -7.523 1.016  0.297  N34  BC2 40 
BC2 H4C1 1H4C H 0 0 N N N -24.434 30.524 -4.012  5.623  2.863  1.094  H4C1 BC2 41 
BC2 H22  H22  H 0 1 N N N -25.981 31.319 -2.017  3.690  3.943  0.228  H22  BC2 42 
BC2 H6C1 1H6C H 0 0 N N N -24.937 33.035 -7.495  5.664  -1.605 0.676  H6C1 BC2 43 
BC2 H361 1H36 H 0 0 N N N -25.038 35.125 0.495   1.229  5.301  1.630  H361 BC2 44 
BC2 H362 2H36 H 0 0 N N N -24.174 36.194 -0.663  0.272  4.048  2.456  H362 BC2 45 
BC2 H363 3H36 H 0 0 N N N -25.901 35.779 -0.938  2.019  3.814  2.208  H363 BC2 46 
BC2 H17  H17  H 0 1 N N N -21.010 36.331 -3.281  -3.656 3.428  1.149  H17  BC2 47 
BC2 H16  H16  H 0 1 N N N -20.886 33.252 -2.750  -1.993 1.592  -0.797 H16  BC2 48 
BC2 H351 1H35 H 0 0 N N N -18.324 34.297 -1.955  -2.939 3.412  -2.147 H351 BC2 49 
BC2 H352 2H35 H 0 0 N N N -19.597 35.193 -1.059  -3.731 1.866  -2.537 H352 BC2 50 
BC2 H353 3H35 H 0 0 N N N -19.530 33.400 -0.971  -4.566 3.062  -1.517 H353 BC2 51 
BC2 H15  H15  H 0 1 N N N -19.014 34.962 -4.358  -3.823 0.948  1.135  H15  BC2 52 
BC2 H7   H7   H 0 1 N N N -27.002 35.442 -5.534  4.133  -2.665 -0.592 H7   BC2 53 
BC2 H8   H8   H 0 1 N N N -25.634 37.167 -6.416  3.140  -3.043 1.389  H8   BC2 54 
BC2 H391 1H39 H 0 0 N N N -28.342 34.477 -6.726  2.895  -1.772 -3.696 H391 BC2 55 
BC2 H392 2H39 H 0 0 N N N -28.410 35.338 -8.301  4.325  -1.237 -2.780 H392 BC2 56 
BC2 H393 3H39 H 0 0 N N N -27.903 33.616 -8.240  3.878  -2.960 -2.807 H393 BC2 57 
BC2 H251 1H25 H 0 0 N N N -23.415 36.732 -4.796  1.137  -0.759 0.767  H251 BC2 58 
BC2 H252 2H25 H 0 0 N N N -24.936 37.603 -4.405  1.201  -1.742 2.250  H252 BC2 59 
BC2 H253 3H25 H 0 0 N N N -24.770 35.860 -4.002  2.547  -0.650 1.848  H253 BC2 60 
BC2 H9C1 1H9C H 0 0 N N N -23.635 34.908 -6.844  1.930  -4.093 -0.573 H9C1 BC2 61 
BC2 H9C2 2H9C H 0 0 N N N -24.348 36.169 -8.056  1.176  -4.169 1.051  H9C2 BC2 62 
BC2 H10  H10  H 0 1 N N N -22.294 36.708 -5.985  -0.131 -3.469 -1.302 H10  BC2 63 
BC2 H11  H11  H 0 1 N N N -20.760 36.898 -7.996  -0.798 -2.264 1.438  H11  BC2 64 
BC2 H271 1H27 H 0 0 N N N -21.742 38.720 -5.784  -1.077 -1.740 -2.432 H271 BC2 65 
BC2 H272 2H27 H 0 0 N N N -21.037 39.132 -7.383  0.133  -0.444 -2.587 H272 BC2 66 
BC2 H273 3H27 H 0 0 N N N -22.448 40.052 -6.760  0.609  -2.141 -2.839 H273 BC2 67 
BC2 H12  H12  H 0 1 N N N -21.826 34.158 -7.702  -2.059 -2.636 -1.219 H12  BC2 68 
BC2 H401 1H40 H 0 0 N N N -21.489 38.075 -9.864  -0.122 -3.832 2.893  H401 BC2 69 
BC2 H402 2H40 H 0 0 N N N -20.677 36.659 -10.614 -1.900 -3.795 2.944  H402 BC2 70 
BC2 H403 3H40 H 0 0 N N N -22.301 37.172 -11.187 -1.043 -5.355 2.917  H403 BC2 71 
BC2 H291 1H29 H 0 0 N N N -20.268 34.453 -9.675  -3.414 -3.737 1.332  H291 BC2 72 
BC2 H292 2H29 H 0 0 N N N -19.100 35.331 -8.629  -4.299 -3.373 -0.169 H292 BC2 73 
BC2 H293 3H29 H 0 0 N N N -19.391 33.576 -8.376  -3.004 -4.594 -0.173 H293 BC2 74 
BC2 H13  H13  H 0 1 N N N -19.623 35.650 -6.100  -2.395 -0.865 1.258  H13  BC2 75 
BC2 H301 1H30 H 0 0 N N N -21.497 32.520 -6.713  -3.478 -1.834 -2.031 H301 BC2 76 
BC2 H302 2H30 H 0 0 N N N -20.763 31.732 -5.276  -4.912 -0.792 -1.873 H302 BC2 77 
BC2 H303 3H30 H 0 0 N N N -22.231 32.750 -5.090  -3.403 -0.132 -2.545 H303 BC2 78 
BC2 H341 1H34 H 0 0 N N N -17.757 34.408 -5.649  -7.786 1.438  -0.536 H341 BC2 79 
BC2 H342 2H34 H 0 0 N N N -16.263 33.621 -6.196  -8.199 0.731  0.932  H342 BC2 80 
BC2 H18  H18  H 0 1 N N N -22.304 35.695 -1.382  -1.534 4.485  1.549  H18  BC2 81 
BC2 H19  H19  H 0 1 N N N -23.368 33.575 -2.777  -0.531 2.745  -0.899 H19  BC2 82 
# 
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 
BC2 O23 C2   DOUB N N 1  
BC2 C2  C3   SING N N 2  
BC2 C3  C4   DOUB N N 3  
BC2 C4  C5   SING N N 4  
BC2 C5  O24  DOUB N N 5  
BC2 C5  C6   SING N N 6  
BC2 C3  N22  SING N N 7  
BC2 N22 C21  SING N N 8  
BC2 C21 O37  DOUB N N 9  
BC2 C21 C20  SING N N 10 
BC2 C20 C36  SING N N 11 
BC2 C20 C19  DOUB N N 12 
BC2 C19 C18  SING N N 13 
BC2 C18 C17  DOUB N N 14 
BC2 C17 C16  SING N N 15 
BC2 C16 C35  SING N N 16 
BC2 C2  C1   SING N E 17 
BC2 C6  C1   DOUB N N 18 
BC2 C1  C7   SING N N 19 
BC2 C7  O38  SING N N 20 
BC2 O38 C39  SING N N 21 
BC2 C7  C8   SING N N 22 
BC2 C8  C25  SING N E 23 
BC2 C8  C9   SING N N 24 
BC2 C9  C10  SING N N 25 
BC2 C10 O26  SING N N 26 
BC2 O26 C27  SING N N 27 
BC2 C10 C11  SING N N 28 
BC2 C11 O28  SING N N 29 
BC2 O28 C40  SING N N 30 
BC2 C11 C12  SING N N 31 
BC2 C12 C29  SING N N 32 
BC2 C12 C13  SING N N 33 
BC2 C13 C14  DOUB N N 34 
BC2 C14 C30  SING N N 35 
BC2 C16 C15  SING N N 36 
BC2 C14 C15  SING N N 37 
BC2 C15 O31  SING N N 38 
BC2 O31 C32  SING N N 39 
BC2 C32 O33  DOUB N N 40 
BC2 C32 N34  SING N N 41 
BC2 C4  H4C1 SING N N 42 
BC2 N22 H22  SING N N 43 
BC2 C6  H6C1 SING N N 44 
BC2 C36 H361 SING N N 45 
BC2 C36 H362 SING N N 46 
BC2 C36 H363 SING N N 47 
BC2 C17 H17  SING N N 48 
BC2 C16 H16  SING N N 49 
BC2 C35 H351 SING N N 50 
BC2 C35 H352 SING N N 51 
BC2 C35 H353 SING N N 52 
BC2 C15 H15  SING N N 53 
BC2 C7  H7   SING N N 54 
BC2 C8  H8   SING N N 55 
BC2 C39 H391 SING N N 56 
BC2 C39 H392 SING N N 57 
BC2 C39 H393 SING N N 58 
BC2 C25 H251 SING N N 59 
BC2 C25 H252 SING N N 60 
BC2 C25 H253 SING N N 61 
BC2 C9  H9C1 SING N N 62 
BC2 C9  H9C2 SING N N 63 
BC2 C10 H10  SING N N 64 
BC2 C11 H11  SING N N 65 
BC2 C27 H271 SING N N 66 
BC2 C27 H272 SING N N 67 
BC2 C27 H273 SING N N 68 
BC2 C12 H12  SING N N 69 
BC2 C40 H401 SING N E 70 
BC2 C40 H402 SING N N 71 
BC2 C40 H403 SING N N 72 
BC2 C29 H291 SING N N 73 
BC2 C29 H292 SING N N 74 
BC2 C29 H293 SING N N 75 
BC2 C13 H13  SING N N 76 
BC2 C30 H301 SING N N 77 
BC2 C30 H302 SING N N 78 
BC2 C30 H303 SING N N 79 
BC2 N34 H341 SING N N 80 
BC2 N34 H342 SING N N 81 
BC2 C18 H18  SING N N 82 
BC2 C19 H19  SING N N 83 
# 
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 
BC2 SMILES           ACDLabs              10.04 O=C1C=C2C(=O)C(=C1)NC(=O)C(=CC=CC(C(OC(=O)N)C(=CC(C)C(OC)C(OC)CC(C)C2OC)C)C)C 
BC2 InChI            InChI                1.02b 
;InChI=1/C30H42N2O8/c1-16-10-9-11-17(2)29(35)32-23-15-21(33)14-22(25(23)34)27(38-7)20(5)13-24(37-6)28(39-8)19(4)12-18(3)26(16)40-30(31)36/h9-12,14-16,19-20,24,26-28H,13H2,1-8H3,(H2,31,36)(H,32,35)/b10-9?,17-11+,18-12+/t16-,19-,20-,24-,26+,27+,28+/m0/s1/f/h32H,31H2
;
BC2 InChIKey         InChI                1.02b PLTGBUPHJAKFMA-MUINZKSKDE 
BC2 SMILES_CANONICAL CACTVS               3.341 CO[C@H]1C[C@H](C)[C@@H](OC)C2=CC(=O)C=C(NC(=O)\C(=C\C=C/[C@H](C)[C@@H](OC(N)=O)C(=C/[C@H](C)[C@H]1OC)/C)C)C2=O 
BC2 SMILES           CACTVS               3.341 CO[CH]1C[CH](C)[CH](OC)C2=CC(=O)C=C(NC(=O)C(=CC=C[CH](C)[CH](OC(N)=O)C(=C[CH](C)[CH]1OC)C)C)C2=O 
BC2 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@H]1C[C@@H]([C@@H]([C@H](\C=C(\[C@@H]([C@H](C=CC=C(C(=O)NC2=CC(=O)C=C([C@@H]1OC)C2=O)C)C)OC(=O)N)/C)C)OC)OC 
BC2 SMILES           "OpenEye OEToolkits" 1.5.0 CC1CC(C(C(C=C(C(C(C=CC=C(C(=O)NC2=CC(=O)C=C(C1OC)C2=O)C)C)OC(=O)N)C)C)OC)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 
BC2 "SYSTEMATIC NAME" ACDLabs              10.04 "(4E,6Z,8S,9R,10E,12S,13R,14S,16S,17R)-13,14,17-trimethoxy-4,8,10,12,16-pentamethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate" 
BC2 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(8S,9R,10E,12S,13R,14S,16S,17R)-13,14,17-trimethoxy-4,8,10,12,16-pentamethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl] carbamate"     
# 
