data_BST
# 
_chem_comp.id                                    BST 
_chem_comp.name                                  "6-(4-AMINO-4-HYDROXY-2-OXO-3,4-DIHYDRO-2H-PYRIMIDIN-1-YL)-3-[3-AMINO-5-(N-METHYL-GUANIDINO)-PENT ANOYLAMINO]-3,6-DIHYDRO-2H-PYRAN-2-CARBOXYLIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C17 H28 N8 O6" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "TETRAHEDRAL INTERMEDIATE OF BLASTICIDIN S" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-07-30 
_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                        440.454 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     BST 
_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        1WN6 
_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 
BST O4    O4    O 0 1 N N N 46.699 17.262 36.298 -0.025  -3.307 0.498  O4    BST 1  
BST N1    N1    N 0 1 N N N 43.455 14.725 38.711 4.741   0.297  0.586  N1    BST 2  
BST C2    C2    C 0 1 N N N 42.478 13.701 38.358 4.939   0.577  -0.710 C2    BST 3  
BST O2    O2    O 0 1 N N N 41.479 13.936 37.687 3.997   0.526  -1.476 O2    BST 4  
BST N3    N3    N 0 1 N N N 42.706 12.384 38.820 6.153   0.923  -1.184 N3    BST 5  
BST C4    C4    C 0 1 N N S 43.892 12.100 39.621 7.282   0.979  -0.241 C4    BST 6  
BST C5    C5    C 0 1 N N N 44.885 13.215 39.961 6.990   0.645  1.207  C5    BST 7  
BST C6    C6    C 0 1 N N N 44.623 14.435 39.501 5.751   0.326  1.534  C6    BST 8  
BST "C1'" "C1'" C 0 1 N N R 43.193 16.108 38.203 3.390   -0.065 1.020  "C1'" BST 9  
BST "C2'" "C2'" C 0 1 N N N 42.735 17.108 39.223 2.480   1.115  0.839  "C2'" BST 10 
BST "C3'" "C3'" C 0 1 N N N 43.190 18.381 39.319 1.251   0.991  0.421  "C3'" BST 11 
BST "C4'" "C4'" C 0 1 N N S 44.299 18.723 38.238 0.676   -0.363 0.092  "C4'" BST 12 
BST "C5'" "C5'" C 0 1 N N S 44.365 17.780 37.000 1.591   -1.449 0.665  "C5'" BST 13 
BST "O5'" "O5'" O 0 1 N N N 44.428 16.462 37.543 2.934   -1.178 0.254  "O5'" BST 14 
BST O3    O3    O 0 1 N N N 45.453 18.587 35.004 1.901   -3.426 -0.578 O3    BST 15 
BST "C6'" "C6'" C 0 1 N N N 45.632 17.791 36.140 1.167   -2.800 0.149  "C6'" BST 16 
BST N6    N6    N 0 1 N N N 44.142 20.103 37.756 -0.659  -0.484 0.683  N6    BST 17 
BST C7    C7    C 0 1 N N N 45.060 21.162 37.699 -1.735  -0.014 0.021  C7    BST 18 
BST O7    O7    O 0 1 N N N 46.223 21.007 38.099 -1.598  0.510  -1.064 O7    BST 19 
BST C8    C8    C 0 1 N N N 44.542 22.481 37.122 -3.108  -0.139 0.630  C8    BST 20 
BST C9    C9    C 0 1 N N S 45.345 23.745 37.538 -4.143  0.468  -0.319 C9    BST 21 
BST N9    N9    N 0 1 N N N 46.764 23.747 37.148 -4.194  -0.319 -1.558 N9    BST 22 
BST C10   C10   C 0 1 N N N 44.693 25.039 36.953 -5.519  0.454  0.351  C10   BST 23 
BST C11   C11   C 0 1 N N N 43.765 25.779 37.960 -6.530  1.174  -0.544 C11   BST 24 
BST N12   N12   N 0 1 N N N 43.025 26.915 37.394 -7.847  1.160  0.097  N12   BST 25 
BST C13   C13   C 0 1 N N N 43.732 28.198 37.287 -8.236  2.251  0.995  C13   BST 26 
BST C14   C14   C 0 1 N N N 41.678 26.758 36.952 -8.718  0.124  -0.144 C14   BST 27 
BST N14   N14   N 0 1 N N N 40.871 27.939 37.042 -8.372  -0.846 -0.942 N14   BST 28 
BST N15   N15   N 0 1 N N N 41.129 25.678 36.491 -9.954  0.111  0.458  N15   BST 29 
BST N4    N4    N 0 1 N N N 44.687 11.065 38.875 7.843   2.336  -0.287 N4    BST 30 
BST O6    O6    O 0 1 N N N 43.362 11.525 40.798 8.287   0.076  -0.706 O6    BST 31 
BST HO4   HO4   H 0 1 N N N 47.485 17.269 35.765 -0.297  -4.175 0.167  HO4   BST 32 
BST HN3   HN3   H 0 1 N N N 42.032 11.657 38.581 6.279   1.128  -2.124 HN3   BST 33 
BST H5    H5    H 0 1 N N N 45.813 13.137 40.552 7.773   0.667  1.951  H5    BST 34 
BST H6    H6    H 0 1 N N N 45.369 15.201 39.773 5.520   0.085  2.561  H6    BST 35 
BST "H1'" "H1'" H 0 1 N N N 42.312 16.123 37.520 3.414   -0.341 2.074  "H1'" BST 36 
BST "H2'" "H2'" H 0 1 N N N 41.976 16.881 39.991 2.856   2.102  1.062  "H2'" BST 37 
BST "H3'" "H3'" H 0 1 N N N 42.749 19.008 40.112 0.637   1.871  0.308  "H3'" BST 38 
BST "H4'" "H4'" H 0 1 N N N 45.256 18.576 38.791 0.607   -0.477 -0.990 "H4'" BST 39 
BST "H5'" "H5'" H 0 1 N N N 43.507 18.102 36.365 1.532   -1.438 1.753  "H5'" BST 40 
BST HN6   HN6   H 0 1 N N N 43.228 20.376 37.395 -0.769  -0.903 1.551  HN6   BST 41 
BST H81   1H8   H 0 1 N N N 43.463 22.612 37.372 -3.133  0.390  1.582  H81   BST 42 
BST H82   2H8   H 0 1 N N N 44.479 22.415 36.011 -3.338  -1.192 0.793  H82   BST 43 
BST H9    H9    H 0 1 N N N 45.308 23.725 38.652 -3.863  1.496  -0.552 H9    BST 44 
BST HN91  1HN9  H 0 0 N N N 46.851 23.592 36.144 -3.249  -0.369 -1.909 HN91  BST 45 
BST HN92  2HN9  H 0 0 N N N 47.291 24.577 37.421 -4.456  -1.257 -1.295 HN92  BST 46 
BST H101  1H10  H 0 0 N N N 44.147 24.813 36.007 -5.460  0.963  1.313  H101  BST 47 
BST H102  2H10  H 0 0 N N N 45.474 25.729 36.556 -5.838  -0.577 0.504  H102  BST 48 
BST H111  1H11  H 0 0 N N N 44.346 26.103 38.855 -6.589  0.665  -1.507 H111  BST 49 
BST H112  2H11  H 0 0 N N N 43.061 25.059 38.438 -6.211  2.205  -0.697 H112  BST 50 
BST H131  1H13  H 0 0 N N N 44.678 28.052 36.715 -7.423  2.974  1.061  H131  BST 51 
BST H132  2H13  H 0 0 N N N 43.170 29.060 36.857 -9.127  2.741  0.605  H132  BST 52 
BST H133  3H13  H 0 0 N N N 44.135 28.482 38.287 -8.446  1.848  1.985  H133  BST 53 
BST H14   H14   H 0 1 N N N 41.312 28.857 36.978 -8.986  -1.577 -1.112 H14   BST 54 
BST H151  1H15  H 0 0 N N N 41.279 24.961 37.200 -10.211 0.833  1.053  H151  BST 55 
BST H152  2H15  H 0 0 N N N 40.166 25.566 36.175 -10.568 -0.620 0.289  H152  BST 56 
BST HN41  1HN4  H 0 0 N N N 44.906 11.341 37.918 8.030   2.539  -1.258 HN41  BST 57 
BST HN42  2HN4  H 0 0 N N N 45.516 10.867 39.435 7.108   2.963  0.004  HN42  BST 58 
BST HO6   HO6   H 0 1 N N N 44.134 11.340 41.320 8.460   0.303  -1.630 HO6   BST 59 
# 
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 
BST O4    "C6'" SING N N 1  
BST O4    HO4   SING N N 2  
BST N1    C2    SING N N 3  
BST N1    C6    SING N N 4  
BST N1    "C1'" SING N N 5  
BST C2    O2    DOUB N N 6  
BST C2    N3    SING N N 7  
BST N3    C4    SING N N 8  
BST N3    HN3   SING N N 9  
BST C4    C5    SING N N 10 
BST C4    N4    SING N N 11 
BST C4    O6    SING N N 12 
BST C5    C6    DOUB N N 13 
BST C5    H5    SING N N 14 
BST C6    H6    SING N N 15 
BST "C1'" "C2'" SING N N 16 
BST "C1'" "O5'" SING N N 17 
BST "C1'" "H1'" SING N N 18 
BST "C2'" "C3'" DOUB N N 19 
BST "C2'" "H2'" SING N N 20 
BST "C3'" "C4'" SING N N 21 
BST "C3'" "H3'" SING N N 22 
BST "C4'" "C5'" SING N N 23 
BST "C4'" N6    SING N N 24 
BST "C4'" "H4'" SING N N 25 
BST "C5'" "O5'" SING N N 26 
BST "C5'" "C6'" SING N N 27 
BST "C5'" "H5'" SING N N 28 
BST O3    "C6'" DOUB N N 29 
BST N6    C7    SING N N 30 
BST N6    HN6   SING N N 31 
BST C7    O7    DOUB N N 32 
BST C7    C8    SING N N 33 
BST C8    C9    SING N N 34 
BST C8    H81   SING N N 35 
BST C8    H82   SING N N 36 
BST C9    N9    SING N N 37 
BST C9    C10   SING N N 38 
BST C9    H9    SING N N 39 
BST N9    HN91  SING N N 40 
BST N9    HN92  SING N N 41 
BST C10   C11   SING N N 42 
BST C10   H101  SING N N 43 
BST C10   H102  SING N N 44 
BST C11   N12   SING N N 45 
BST C11   H111  SING N N 46 
BST C11   H112  SING N N 47 
BST N12   C13   SING N N 48 
BST N12   C14   SING N N 49 
BST C13   H131  SING N N 50 
BST C13   H132  SING N N 51 
BST C13   H133  SING N N 52 
BST C14   N14   DOUB N N 53 
BST C14   N15   SING N N 54 
BST N14   H14   SING N N 55 
BST N15   H151  SING N N 56 
BST N15   H152  SING N N 57 
BST N4    HN41  SING N N 58 
BST N4    HN42  SING N N 59 
BST O6    HO6   SING N N 60 
# 
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 
BST SMILES           ACDLabs              10.04 O=C1NC(O)(N)C=CN1C2OC(C(=O)O)C(C=C2)NC(=O)CC(N)CCN(C(=[N@H])N)C 
BST InChI            InChI                1.02b 
InChI=1/C17H28N8O6/c1-24(15(19)20)6-4-9(18)8-11(26)22-10-2-3-12(31-13(10)14(27)28)25-7-5-17(21,30)23-16(25)29/h2-3,5,7,9-10,12-13,30H,4,6,8,18,21H2,1H3,(H3,19,20)(H,22,26)(H,23,29)(H,27,28)/t9-,10-,12+,13-,17-/m0/s1/f/h19,22-23,27H,20H2/b19-15- 
BST InChIKey         InChI                1.02b MVFPGTZTOAHVBP-AENNWJLBDX 
BST SMILES_CANONICAL CACTVS               3.341 CN(CC[C@H](N)CC(=O)N[C@H]1C=C[C@@H](O[C@@H]1C(O)=O)N2C=C[C@@](N)(O)NC2=O)C(N)=N 
BST SMILES           CACTVS               3.341 CN(CC[CH](N)CC(=O)N[CH]1C=C[CH](O[CH]1C(O)=O)N2C=C[C](N)(O)NC2=O)C(N)=N 
BST SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CN(CC[C@@H](CC(=O)N[C@H]1C=C[C@@H](O[C@@H]1C(=O)O)N2C=C[C@@](NC2=O)(N)O)N)C(=N)N 
BST SMILES           "OpenEye OEToolkits" 1.5.0 CN(CCC(CC(=O)NC1C=CC(OC1C(=O)O)N2C=CC(NC2=O)(N)O)N)C(=N)N 
# 
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 
BST "SYSTEMATIC NAME" ACDLabs              10.04 (4S)-4-amino-1-[4-({(3S)-3-amino-5-[carbamimidoyl(methyl)amino]pentanoyl}amino)-2,3,4-trideoxy-beta-D-erythro-hex-2-enopyranuronosyl]-4-hydroxy-3,4-dihydropyrimidin-2(1H)-one 
BST "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S,3S,6R)-3-[[(3S)-3-amino-5-(carbamimidoyl-methyl-amino)pentanoyl]amino]-6-[(4S)-4-amino-4-hydroxy-2-oxo-3H-pyrimidin-1-yl]-3,6-dihydro-2H-pyran-2-carboxylic acid"         
# 
