data_GNA
# 
_chem_comp.id                                    GNA 
_chem_comp.name                                  "2,4-DEOXY-4-GUANIDINO-5-N-ACETYL-NEURAMINIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C12 H22 N4 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                        334.326 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GNA 
_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        ? 
_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 
GNA C1   C1   C 0 1 N N N 23.764 19.976 65.044 -2.676 0.382  0.161  C1   GNA 1  
GNA C2   C2   C 0 1 N N R 24.438 18.955 64.271 -2.153 -1.027 0.066  C2   GNA 2  
GNA C3   C3   C 0 1 N N N 23.833 17.784 63.820 -1.592 -1.268 -1.336 C3   GNA 3  
GNA C4   C4   C 0 1 N N S 24.488 16.914 62.761 -0.473 -0.255 -1.607 C4   GNA 4  
GNA C5   C5   C 0 1 N N R 26.046 17.044 62.841 0.551  -0.340 -0.470 C5   GNA 5  
GNA C6   C6   C 0 1 N N R 26.436 18.517 62.761 -0.171 -0.171 0.868  C6   GNA 6  
GNA C7   C7   C 0 1 N N R 27.927 18.766 63.014 0.848  -0.224 2.008  C7   GNA 7  
GNA C8   C8   C 0 1 N N R 28.272 20.254 62.734 0.127  -0.046 3.345  C8   GNA 8  
GNA C9   C9   C 0 1 N N N 29.758 20.576 62.928 1.146  -0.098 4.485  C9   GNA 9  
GNA C10  C10  C 0 1 N N N 27.287 15.165 61.916 2.666  0.496  -1.344 C10  GNA 10 
GNA C11  C11  C 0 1 N N N 27.918 14.556 60.686 3.690  1.589  -1.505 C11  GNA 11 
GNA N5   N5   N 0 1 N N N 26.694 16.341 61.760 1.547  0.721  -0.627 N5   GNA 12 
GNA N4   N4   N 0 1 N N N 24.078 15.548 62.959 0.178  -0.567 -2.881 N4   GNA 13 
GNA C12  C12  C 0 1 N N N 23.938 14.577 62.051 -0.280 0.001  -4.045 C12  GNA 14 
GNA N6   N6   N 0 1 N N N 24.079 14.823 60.758 -1.295 0.818  -4.016 N6   GNA 15 
GNA N7   N7   N 0 1 N N N 23.702 13.340 62.450 0.332  -0.290 -5.241 N7   GNA 16 
GNA O1A  O1A  O 0 1 N N N 24.332 21.075 65.161 -3.277 0.868  -0.767 O1A  GNA 17 
GNA O1B  O1B  O 0 1 N N N 22.630 19.787 65.513 -2.475 1.098  1.279  O1B  GNA 18 
GNA O6   O6   O 0 1 N N N 25.739 19.250 63.791 -1.126 -1.217 1.037  O6   GNA 19 
GNA O7   O7   O 0 1 N N N 28.140 18.457 64.360 1.515  -1.487 1.991  O7   GNA 20 
GNA O8   O8   O 0 1 N N N 27.927 20.510 61.419 -0.540 1.217  3.362  O8   GNA 21 
GNA O9   O9   O 0 1 N N N 30.532 19.656 62.214 0.472  0.067  5.734  O9   GNA 22 
GNA O10  O10  O 0 1 N N N 27.280 14.569 62.992 2.848  -0.586 -1.858 O10  GNA 23 
GNA H2   H2   H 0 1 N N N 24.305 18.406 65.233 -2.966 -1.728 0.256  H2   GNA 24 
GNA H31  1H3  H 0 1 N N N 23.618 17.143 64.707 -2.385 -1.141 -2.073 H31  GNA 25 
GNA H32  2H3  H 0 1 N N N 22.806 18.040 63.468 -1.191 -2.279 -1.400 H32  GNA 26 
GNA H4   H4   H 0 1 N N N 24.168 17.249 61.746 -0.892 0.750  -1.647 H4   GNA 27 
GNA H5   H5   H 0 1 N N N 26.375 16.596 63.807 1.045  -1.311 -0.497 H5   GNA 28 
GNA H6   H6   H 0 1 N N N 26.175 18.844 61.727 -0.681 0.791  0.883  H6   GNA 29 
GNA H7   H7   H 0 1 N N N 28.571 18.146 62.347 1.578  0.574  1.879  H7   GNA 30 
GNA H8   H8   H 0 1 N N N 27.711 20.888 63.459 -0.603 -0.844 3.474  H8   GNA 31 
GNA H91  1H9  H 0 1 N N N 29.999 21.630 62.656 1.655  -1.062 4.473  H91  GNA 32 
GNA H92  2H9  H 0 1 N N N 30.042 20.619 64.005 1.876  0.700  4.357  H92  GNA 33 
GNA H111 1H11 H 0 0 N N N 28.416 13.567 60.817 4.519  1.223  -2.112 H111 GNA 34 
GNA H112 2H11 H 0 0 N N N 27.159 14.487 59.871 3.232  2.447  -1.997 H112 GNA 35 
GNA H113 3H11 H 0 0 N N N 28.636 15.280 60.236 4.061  1.887  -0.525 H113 GNA 36 
GNA HN5  HN5  H 0 1 N N N 26.736 16.705 60.808 1.401  1.588  -0.215 HN5  GNA 37 
GNA HN4  HN4  H 0 1 N N N 23.181 15.600 63.442 0.934  -1.175 -2.903 HN4  GNA 38 
GNA HN6  HN6  H 0 1 N N N 24.297 14.823 61.754 -1.619 1.220  -4.837 HN6  GNA 39 
GNA HN71 1HN7 H 0 0 N N N 23.595 12.599 61.757 0.008  0.110  -6.063 HN71 GNA 40 
GNA HN72 2HN7 H 0 0 N N N 22.878 13.344 63.051 1.087  -0.898 -5.263 HN72 GNA 41 
GNA HOB1 1HOB H 0 0 N N N 22.187 20.457 66.020 -2.811 2.003  1.340  HOB1 GNA 42 
GNA HO7  HO7  H 0 1 N N N 29.064 18.611 64.516 0.835  -2.165 2.107  HO7  GNA 43 
GNA HO8  HO8  H 0 1 N N N 28.138 21.420 61.247 0.139  1.894  3.245  HO8  GNA 44 
GNA HO9  HO9  H 0 1 N N N 31.453 19.855 62.334 1.149  0.028  6.424  HO9  GNA 45 
# 
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 
GNA C1  C2   SING N N 1  
GNA C1  O1A  DOUB N N 2  
GNA C1  O1B  SING N N 3  
GNA C2  C3   SING N N 4  
GNA C2  O6   SING N N 5  
GNA C2  H2   SING N N 6  
GNA C3  C4   SING N N 7  
GNA C3  H31  SING N N 8  
GNA C3  H32  SING N N 9  
GNA C4  C5   SING N N 10 
GNA C4  N4   SING N N 11 
GNA C4  H4   SING N N 12 
GNA C5  C6   SING N N 13 
GNA C5  N5   SING N N 14 
GNA C5  H5   SING N N 15 
GNA C6  C7   SING N N 16 
GNA C6  O6   SING N N 17 
GNA C6  H6   SING N N 18 
GNA C7  C8   SING N N 19 
GNA C7  O7   SING N N 20 
GNA C7  H7   SING N N 21 
GNA C8  C9   SING N N 22 
GNA C8  O8   SING N N 23 
GNA C8  H8   SING N N 24 
GNA C9  O9   SING N N 25 
GNA C9  H91  SING N N 26 
GNA C9  H92  SING N N 27 
GNA C10 C11  SING N N 28 
GNA C10 N5   SING N N 29 
GNA C10 O10  DOUB N N 30 
GNA C11 H111 SING N N 31 
GNA C11 H112 SING N N 32 
GNA C11 H113 SING N N 33 
GNA N5  HN5  SING N N 34 
GNA N4  C12  SING N N 35 
GNA N4  HN4  SING N N 36 
GNA C12 N6   DOUB N N 37 
GNA C12 N7   SING N N 38 
GNA N6  HN6  SING N N 39 
GNA N7  HN71 SING N N 40 
GNA N7  HN72 SING N N 41 
GNA O1B HOB1 SING N N 42 
GNA O7  HO7  SING N N 43 
GNA O8  HO8  SING N N 44 
GNA O9  HO9  SING N N 45 
# 
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 
GNA SMILES           ACDLabs              10.04 O=C(O)C1OC(C(O)C(O)CO)C(NC(=O)C)C(NC(=[N@H])N)C1                                                                                                                                                   
GNA InChI            InChI                1.02b InChI=1/C12H22N4O7/c1-4(18)15-8-5(16-12(13)14)2-7(11(21)22)23-10(8)9(20)6(19)3-17/h5-10,17,19-20H,2-3H2,1H3,(H,15,18)(H,21,22)(H4,13,14,16)/t5-,6+,7+,8+,9+,10+/m0/s1/f/h13,15-16,21H,14H2/b13-12- 
GNA InChIKey         InChI                1.02b DAAUVSVERFXBSX-IHTFOOFUDO                                                                                                                                                                          
GNA SMILES_CANONICAL CACTVS               3.341 CC(=O)N[C@@H]1[C@H](C[C@@H](O[C@H]1[C@H](O)[C@H](O)CO)C(O)=O)NC(N)=N                                                                                                                               
GNA SMILES           CACTVS               3.341 CC(=O)N[CH]1[CH](C[CH](O[CH]1[CH](O)[CH](O)CO)C(O)=O)NC(N)=N                                                                                                                                       
GNA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(=O)N[C@@H]1[C@H](CC(O[C@H]1[C@@H]([C@@H](CO)O)O)C(=O)O)NC(=N)N                                                                                                                                  
GNA SMILES           "OpenEye OEToolkits" 1.5.0 CC(=O)NC1C(CC(OC1C(C(CO)O)O)C(=O)O)NC(=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 
GNA "SYSTEMATIC NAME" ACDLabs              10.04 "5-(acetylamino)-2,6-anhydro-4-carbamimidamido-3,4,5-trideoxy-D-erythro-L-manno-nononic acid"        
GNA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(4S,5R,6R)-5-acetamido-4-carbamimidamido-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid" 
# 
