data_BFN
# 
_chem_comp.id                                    BFN 
_chem_comp.name                                  "5-(acetylamino)-2,6-anhydro-3,5,9-trideoxy-3-fluoro-9-[(phenylcarbonyl)amino]-D-arabino-L-galacto-nononic acid" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C18 H23 F N2 O8" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "3-fluoro-5-N-acetyl-9-benzamido-2,9-dideoxy-neuraminic acid" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-11-07 
_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                        414.382 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     BFN 
_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        3B69 
_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 
BFN C11  C11  C 0 1 N N N 12.065 -19.643 -4.883 -4.102 4.380  0.686  C11  BFN 1  
BFN C10  C10  C 0 1 N N N 10.831 -19.327 -5.727 -3.958 3.002  0.093  C10  BFN 2  
BFN O10  O10  O 0 1 N N N 10.144 -20.240 -6.197 -4.549 2.717  -0.928 O10  BFN 3  
BFN N5   N5   N 0 1 N N N 10.574 -18.032 -5.880 -3.174 2.087  0.696  N5   BFN 4  
BFN C5   C5   C 0 1 N N R 9.437  -17.520 -6.662 -3.035 0.748  0.119  C5   BFN 5  
BFN C4   C4   C 0 1 N N R 9.855  -16.320 -7.513 -4.183 -0.141 0.606  C4   BFN 6  
BFN O4   O4   O 0 1 N N N 10.904 -16.723 -8.399 -5.426 0.383  0.136  O4   BFN 7  
BFN C3   C3   C 0 1 N N R 8.639  -15.838 -8.308 -3.983 -1.559 0.060  C3   BFN 8  
BFN F1   F1   F 0 1 N N N 8.256  -16.835 -9.196 -4.042 -1.533 -1.338 F1   BFN 9  
BFN C2   C2   C 0 1 N N R 7.494  -15.443 -7.365 -2.615 -2.081 0.505  C2   BFN 10 
BFN C1   C1   C 0 1 N N N 6.179  -15.153 -8.094 -2.386 -3.452 -0.078 C1   BFN 11 
BFN O1A  O1A  O 0 1 N N N 5.129  -15.190 -7.416 -3.167 -4.478 0.294  O1A  BFN 12 
BFN O1B  O1B  O 0 1 N N N 6.200  -14.903 -9.320 -1.500 -3.627 -0.881 O1B  BFN 13 
BFN O6   O6   O 0 1 N N N 7.177  -16.556 -6.513 -1.595 -1.192 0.045  O6   BFN 14 
BFN C6   C6   C 0 1 N N R 8.265  -17.124 -5.761 -1.703 0.137  0.562  C6   BFN 15 
BFN C7   C7   C 0 1 N N R 7.736  -18.390 -5.080 -0.548 0.987  0.028  C7   BFN 16 
BFN O7   O7   O 0 1 N N N 7.486  -19.417 -6.045 -0.671 1.120  -1.390 O7   BFN 17 
BFN C8   C8   C 0 1 N N R 6.444  -18.095 -4.319 0.782  0.310  0.363  C8   BFN 18 
BFN O8   O8   O 0 1 N N N 6.730  -17.246 -3.206 0.904  0.176  1.781  O8   BFN 19 
BFN C9   C9   C 0 1 N N N 5.846  -19.424 -3.852 1.936  1.160  -0.171 C9   BFN 20 
BFN N9   N9   N 0 1 N N N 5.231  -20.170 -4.750 3.202  0.455  0.045  N9   BFN 21 
BFN C12  C12  C 0 1 N N N 4.068  -20.751 -4.470 4.362  1.017  -0.349 C12  BFN 22 
BFN O12  O12  O 0 1 N N N 3.500  -20.668 -3.384 4.358  2.109  -0.883 O12  BFN 23 
BFN C13  C13  C 0 1 Y N N 3.461  -21.559 -5.619 5.640  0.306  -0.132 C13  BFN 24 
BFN C14  C14  C 0 1 Y N N 2.145  -22.007 -5.535 6.843  0.886  -0.539 C14  BFN 25 
BFN C15  C15  C 0 1 Y N N 1.556  -22.650 -6.616 8.031  0.216  -0.333 C15  BFN 26 
BFN C16  C16  C 0 1 Y N N 2.282  -22.848 -7.786 8.033  -1.026 0.275  C16  BFN 27 
BFN C17  C17  C 0 1 Y N N 3.596  -22.404 -7.870 6.844  -1.607 0.680  C17  BFN 28 
BFN C18  C18  C 0 1 Y N N 4.186  -21.763 -6.785 5.649  -0.946 0.485  C18  BFN 29 
BFN H11  H11  H 0 1 N N N 12.947 -19.719 -5.536 -4.771 4.976  0.064  H11  BFN 30 
BFN H11A H11A H 0 0 N N N 12.222 -18.840 -4.148 -4.515 4.301  1.692  H11A BFN 31 
BFN H11B H11B H 0 0 N N N 11.915 -20.598 -4.358 -3.125 4.860  0.731  H11B BFN 32 
BFN HN5  HN5  H 0 1 N N N 11.184 -17.372 -5.442 -2.702 2.315  1.512  HN5  BFN 33 
BFN H5   H5   H 0 1 N N N 9.109  -18.336 -7.323 -3.061 0.815  -0.969 H5   BFN 34 
BFN H4   H4   H 0 1 N N N 10.220 -15.500 -6.878 -4.186 -0.168 1.696  H4   BFN 35 
BFN HO4  HO4  H 0 1 N N N 10.559 -16.812 -9.279 -6.198 -0.132 0.408  HO4  BFN 36 
BFN H3   H3   H 0 1 N N N 8.903  -14.938 -8.882 -4.766 -2.211 0.446  H3   BFN 37 
BFN H2   H2   H 0 1 N N N 7.849  -14.546 -6.836 -2.584 -2.138 1.593  H2   BFN 38 
BFN HO1A HO1A H 0 0 N N N 4.384  -15.002 -7.975 -2.982 -5.338 -0.107 HO1A BFN 39 
BFN H6   H6   H 0 1 N N N 8.628  -16.377 -5.040 -1.660 0.108  1.651  H6   BFN 40 
BFN H7   H7   H 0 1 N N N 8.505  -18.734 -4.373 -0.580 1.974  0.490  H7   BFN 41 
BFN HO7  HO7  H 0 1 N N N 7.431  -19.031 -6.911 -0.650 0.279  -1.867 HO7  BFN 42 
BFN H8   H8   H 0 1 N N N 5.720  -17.579 -4.967 0.814  -0.677 -0.098 H8   BFN 43 
BFN HO8  HO8  H 0 1 N N N 6.793  -17.770 -2.416 0.884  1.017  2.258  HO8  BFN 44 
BFN H9   H9   H 0 1 N N N 6.678  -20.025 -3.455 1.795  1.336  -1.237 H9   BFN 45 
BFN H9A  H9A  H 0 1 N N N 5.062  -19.144 -3.133 1.958  2.114  0.355  H9A  BFN 46 
BFN HN9  HN9  H 0 1 N N N 5.644  -20.300 -5.651 3.206  -0.417 0.470  HN9  BFN 47 
BFN H14  H14  H 0 1 N N N 1.581  -21.854 -4.627 6.843  1.855  -1.014 H14  BFN 48 
BFN H15  H15  H 0 1 N N N 0.535  -22.996 -6.548 8.963  0.664  -0.647 H15  BFN 49 
BFN H16  H16  H 0 1 N N N 1.825  -23.346 -8.628 8.966  -1.546 0.433  H16  BFN 50 
BFN H17  H17  H 0 1 N N N 4.160  -22.557 -8.778 6.852  -2.577 1.154  H17  BFN 51 
BFN H18  H18  H 0 1 N N N 5.209  -21.424 -6.850 4.722  -1.400 0.803  H18  BFN 52 
# 
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 
BFN C10 C11  SING N N 1  
BFN C11 H11  SING N N 2  
BFN C11 H11A SING N N 3  
BFN C11 H11B SING N N 4  
BFN O10 C10  DOUB N N 5  
BFN N5  C10  SING N N 6  
BFN C5  N5   SING N N 7  
BFN N5  HN5  SING N N 8  
BFN C4  C5   SING N N 9  
BFN C5  C6   SING N N 10 
BFN C5  H5   SING N N 11 
BFN O4  C4   SING N N 12 
BFN C3  C4   SING N N 13 
BFN C4  H4   SING N N 14 
BFN O4  HO4  SING N N 15 
BFN F1  C3   SING N N 16 
BFN C3  C2   SING N N 17 
BFN C3  H3   SING N N 18 
BFN C1  C2   SING N N 19 
BFN C2  O6   SING N N 20 
BFN C2  H2   SING N N 21 
BFN O1B C1   DOUB N N 22 
BFN C1  O1A  SING N N 23 
BFN O1A HO1A SING N N 24 
BFN O6  C6   SING N N 25 
BFN C6  C7   SING N N 26 
BFN C6  H6   SING N N 27 
BFN O7  C7   SING N N 28 
BFN C7  C8   SING N N 29 
BFN C7  H7   SING N N 30 
BFN O7  HO7  SING N N 31 
BFN C8  C9   SING N N 32 
BFN C8  O8   SING N N 33 
BFN C8  H8   SING N N 34 
BFN O8  HO8  SING N N 35 
BFN N9  C9   SING N N 36 
BFN C9  H9   SING N N 37 
BFN C9  H9A  SING N N 38 
BFN N9  C12  SING N N 39 
BFN N9  HN9  SING N N 40 
BFN C13 C12  SING N N 41 
BFN C12 O12  DOUB N N 42 
BFN C18 C13  DOUB Y N 43 
BFN C13 C14  SING N N 44 
BFN C15 C14  DOUB Y N 45 
BFN C14 H14  SING N N 46 
BFN C16 C15  SING Y N 47 
BFN C15 H15  SING N N 48 
BFN C17 C16  DOUB Y N 49 
BFN C16 H16  SING Y N 50 
BFN C17 C18  SING N N 51 
BFN C17 H17  SING Y N 52 
BFN C18 H18  SING N N 53 
# 
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 
BFN SMILES           ACDLabs              10.04 O=C(c1ccccc1)NCC(O)C(O)C2OC(C(=O)O)C(F)C(O)C2NC(=O)C                                                                                                                                                          
BFN InChI            InChI                1.02b InChI=1/C18H23FN2O8/c1-8(22)21-12-14(25)11(19)15(18(27)28)29-16(12)13(24)10(23)7-20-17(26)9-5-3-2-4-6-9/h2-6,10-16,23-25H,7H2,1H3,(H,20,26)(H,21,22)(H,27,28)/t10-,11-,12-,13-,14+,15+,16-/m1/s1/f/h20-21,27H 
BFN InChIKey         InChI                1.02b CECJHKNVIBPLPJ-KVIDTNPJDV                                                                                                                                                                                     
BFN SMILES_CANONICAL CACTVS               3.341 CC(=O)N[C@@H]1[C@@H](O)[C@@H](F)[C@H](O[C@H]1[C@H](O)[C@H](O)CNC(=O)c2ccccc2)C(O)=O                                                                                                                           
BFN SMILES           CACTVS               3.341 CC(=O)N[CH]1[CH](O)[CH](F)[CH](O[CH]1[CH](O)[CH](O)CNC(=O)c2ccccc2)C(O)=O                                                                                                                                     
BFN SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(=O)N[C@@H]1[C@H]([C@H]([C@H](O[C@H]1[C@@H]([C@@H](CNC(=O)c2ccccc2)O)O)C(=O)O)F)O                                                                                                                           
BFN SMILES           "OpenEye OEToolkits" 1.5.0 CC(=O)NC1C(C(C(OC1C(C(CNC(=O)c2ccccc2)O)O)C(=O)O)F)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 
BFN "SYSTEMATIC NAME" ACDLabs              10.04 "5-(acetylamino)-2,6-anhydro-3,5,9-trideoxy-3-fluoro-9-[(phenylcarbonyl)amino]-D-arabino-L-galacto-nononic acid"       
BFN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2R,3R,4R,5R,6R)-5-acetamido-6-[(1R,2R)-3-benzamido-1,2-dihydroxy-propyl]-3-fluoro-4-hydroxy-oxane-2-carboxylic acid" 
# 
