data_4AM
# 
_chem_comp.id                                    4AM 
_chem_comp.name                                  "4-AMINO-2-DEOXY-2,3-DEHYDRO-N-NEURAMINIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C11 H18 N2 O7" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_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                        290.270 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     4AM 
_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        2QWD 
_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 
4AM C1   C1   C 0 1 N N N 23.547 19.823 64.794 -3.334 0.144  -1.192 C1   4AM 1  
4AM O1A  O1A  O 0 1 N N N 24.239 20.800 65.125 -4.435 -0.155 -0.775 O1A  4AM 2  
4AM O1B  O1B  O 0 1 N N N 22.320 19.788 65.025 -3.192 0.607  -2.449 O1B  4AM 3  
4AM C2   C2   C 0 1 N N N 24.187 18.807 64.073 -2.153 0.001  -0.322 C2   4AM 4  
4AM C3   C3   C 0 1 N N N 23.497 17.780 63.471 -2.365 -0.458 0.896  C3   4AM 5  
4AM C4   C4   C 0 1 N N S 24.187 16.694 62.639 -1.245 -0.671 1.882  C4   4AM 6  
4AM N4   N4   N 0 1 N N N 23.637 15.422 63.082 -1.600 -0.071 3.175  N4   4AM 7  
4AM C5   C5   C 0 1 N N R 25.700 16.750 62.831 0.016  0.004  1.325  C5   4AM 8  
4AM N5   N5   N 0 1 N N N 26.327 16.038 61.693 1.203  -0.517 2.007  N5   4AM 9  
4AM C10  C10  C 0 1 N N N 26.921 14.861 61.882 1.667  0.092  3.115  C10  4AM 10 
4AM O10  O10  O 0 1 N N N 27.019 14.329 62.995 1.102  1.073  3.549  O10  4AM 11 
4AM C11  C11  C 0 1 N N N 27.530 14.163 60.659 2.888  -0.445 3.816  C11  4AM 12 
4AM C6   C6   C 0 1 N N R 26.149 18.214 62.817 0.089  -0.319 -0.172 C6   4AM 13 
4AM O6   O6   O 0 1 N N N 25.578 18.842 63.941 -0.967 0.351  -0.849 O6   4AM 14 
4AM C7   C7   C 0 1 N N R 27.669 18.356 62.904 1.433  0.147  -0.734 C7   4AM 15 
4AM O7   O7   O 0 1 N N N 28.141 17.731 64.078 1.565  1.557  -0.544 O7   4AM 16 
4AM C8   C8   C 0 1 N N R 28.052 19.827 62.904 1.501  -0.174 -2.228 C8   4AM 17 
4AM O8   O8   O 0 1 N N N 27.735 20.200 61.632 1.369  -1.584 -2.418 O8   4AM 18 
4AM C9   C9   C 0 1 N N N 29.523 20.106 63.100 2.845  0.292  -2.790 C9   4AM 19 
4AM O9   O9   O 0 1 N N N 30.294 19.368 62.230 2.908  -0.007 -4.186 O9   4AM 20 
4AM HOB1 1HOB H 0 0 N N N 21.790 19.040 64.771 -3.967 0.701  -3.020 HOB1 4AM 21 
4AM H3   H3   H 0 1 N N N 22.410 17.826 63.652 -3.376 -0.690 1.197  H3   4AM 22 
4AM H4   H4   H 0 1 N N N 24.004 16.838 61.548 -1.064 -1.739 2.009  H4   4AM 23 
4AM HN41 1HN4 H 0 0 N N N 24.096 14.699 62.528 -2.430 -0.547 3.497  HN41 4AM 24 
4AM HN42 2HN4 H 0 0 N N N 22.619 15.383 63.032 -0.861 -0.311 3.818  HN42 4AM 25 
4AM H5   H5   H 0 1 N N N 25.994 16.280 63.798 -0.047 1.083  1.469  H5   4AM 26 
4AM H5N  NH5  H 0 1 N N N 26.350 16.375 60.730 1.655  -1.302 1.660  H5N  4AM 27 
4AM H111 1H11 H 0 0 N N N 28.027 13.177 60.817 3.110  0.173  4.685  H111 4AM 28 
4AM H112 2H11 H 0 0 N N N 26.749 14.057 59.870 2.701  -1.470 4.138  H112 4AM 29 
4AM H113 3H11 H 0 0 N N N 28.243 14.857 60.157 3.736  -0.429 3.132  H113 4AM 30 
4AM H6   H6   H 0 1 N N N 25.820 18.677 61.857 -0.011 -1.395 -0.315 H6   4AM 31 
4AM H7   H7   H 0 1 N N N 28.134 17.862 62.019 2.242  -0.366 -0.215 H7   4AM 32 
4AM H7O  OH7  H 0 1 N N N 29.085 17.819 64.132 0.832  1.973  -1.018 H7O  4AM 33 
4AM H8   H8   H 0 1 N N N 27.541 20.357 63.741 0.692  0.339  -2.747 H8   4AM 34 
4AM H8O  OH8  H 0 1 N N N 27.974 21.119 61.632 2.102  -2.000 -1.944 H8O  4AM 35 
4AM H91  1H9  H 0 1 N N N 29.746 21.195 63.020 2.946  1.368  -2.645 H91  4AM 36 
4AM H92  2H9  H 0 1 N N N 29.832 19.943 64.158 3.654  -0.221 -2.271 H92  4AM 37 
4AM HO9  HO9  H 0 1 N N N 31.219 19.543 62.353 3.769  0.302  -4.500 HO9  4AM 38 
# 
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 
4AM C1  O1A  DOUB N N 1  
4AM C1  O1B  SING N N 2  
4AM C1  C2   SING N N 3  
4AM O1B HOB1 SING N N 4  
4AM C2  C3   DOUB N N 5  
4AM C2  O6   SING N N 6  
4AM C3  C4   SING N N 7  
4AM C3  H3   SING N N 8  
4AM C4  N4   SING N N 9  
4AM C4  C5   SING N N 10 
4AM C4  H4   SING N N 11 
4AM N4  HN41 SING N N 12 
4AM N4  HN42 SING N N 13 
4AM C5  N5   SING N N 14 
4AM C5  C6   SING N N 15 
4AM C5  H5   SING N N 16 
4AM N5  C10  SING N N 17 
4AM N5  H5N  SING N N 18 
4AM C10 O10  DOUB N N 19 
4AM C10 C11  SING N N 20 
4AM C11 H111 SING N N 21 
4AM C11 H112 SING N N 22 
4AM C11 H113 SING N N 23 
4AM C6  O6   SING N N 24 
4AM C6  C7   SING N N 25 
4AM C6  H6   SING N N 26 
4AM C7  O7   SING N N 27 
4AM C7  C8   SING N N 28 
4AM C7  H7   SING N N 29 
4AM O7  H7O  SING N N 30 
4AM C8  O8   SING N N 31 
4AM C8  C9   SING N N 32 
4AM C8  H8   SING N N 33 
4AM O8  H8O  SING N N 34 
4AM C9  O9   SING N N 35 
4AM C9  H91  SING N N 36 
4AM C9  H92  SING N N 37 
4AM O9  HO9  SING N N 38 
# 
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 
4AM SMILES           ACDLabs              10.04 O=C(O)C=1OC(C(O)C(O)CO)C(NC(=O)C)C(C=1)N                                                                                                                      
4AM InChI            InChI                1.02b InChI=1/C11H18N2O7/c1-4(15)13-8-5(12)2-7(11(18)19)20-10(8)9(17)6(16)3-14/h2,5-6,8-10,14,16-17H,3,12H2,1H3,(H,13,15)(H,18,19)/t5-,6+,8+,9+,10+/m0/s1/f/h13,18H 
4AM InChIKey         InChI                1.02b NKENBBIXEGPQLS-UNPWIPMKDO                                                                                                                                     
4AM SMILES_CANONICAL CACTVS               3.341 CC(=O)N[C@@H]1[C@@H](N)C=C(O[C@H]1[C@H](O)[C@H](O)CO)C(O)=O                                                                                                   
4AM SMILES           CACTVS               3.341 CC(=O)N[CH]1[CH](N)C=C(O[CH]1[CH](O)[CH](O)CO)C(O)=O                                                                                                          
4AM SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(=O)N[C@@H]1[C@H](C=C(O[C@H]1[C@@H]([C@@H](CO)O)O)C(=O)O)N                                                                                                  
4AM SMILES           "OpenEye OEToolkits" 1.5.0 CC(=O)NC1C(C=C(OC1C(C(CO)O)O)C(=O)O)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 
4AM "SYSTEMATIC NAME" ACDLabs              10.04 "5-(acetylamino)-4-amino-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid"                 
4AM "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(4S,5R,6R)-5-acetamido-4-amino-6-[(1R,2R)-1,2,3-trihydroxypropyl]-5,6-dihydro-4H-pyran-2-carboxylic acid" 
# 
