data_SIO
# 
_chem_comp.id                                    SIO 
_chem_comp.name                                  "methyl 4,9-di-O-acetyl-5-(acetylamino)-3,5-dideoxy-D-glycero-alpha-D-galacto-non-2-ulopyranosidonic acid" 
_chem_comp.type                                  saccharide 
_chem_comp.pdbx_type                             ATOMS 
_chem_comp.formula                               "C16 H25 N O11" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         None 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-03-20 
_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                        407.370 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     SIO 
_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        3CL5 
_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 
SIO OA4  OA4  O 0 1 N N N 18.330 8.296  19.934 4.756  0.410  0.992  OA4  SIO 1  
SIO CA4  CA4  C 0 1 N N N 19.494 8.417  19.588 4.709  -0.383 0.082  CA4  SIO 2  
SIO CM4  CM4  C 0 1 N N N 20.592 8.711  20.553 5.961  -1.095 -0.363 CM4  SIO 3  
SIO O4   O4   O 0 1 N N N 19.796 8.269  18.181 3.541  -0.634 -0.530 O4   SIO 4  
SIO C4   C4   C 0 1 N N S 21.178 8.426  17.843 2.375  0.083  -0.045 C4   SIO 5  
SIO C5   C5   C 0 1 N N R 21.385 9.723  17.049 1.122  -0.771 -0.260 C5   SIO 6  
SIO N5   N5   N 0 1 N N N 21.358 10.775 18.063 1.223  -1.997 0.535  N5   SIO 7  
SIO C10  C10  C 0 1 N N N 20.247 11.471 18.268 1.878  -3.067 0.042  C10  SIO 8  
SIO O10  O10  O 0 1 N N N 19.243 11.289 17.594 2.384  -3.015 -1.059 O10  SIO 9  
SIO C11  C11  C 0 1 N N N 20.303 12.517 19.358 1.982  -4.329 0.859  C11  SIO 10 
SIO C3   C3   C 0 1 N N N 21.597 7.188  17.051 2.225  1.398  -0.817 C3   SIO 11 
SIO C2   C2   C 0 1 N N R 22.924 7.333  16.304 0.951  2.109  -0.354 C2   SIO 12 
SIO O2   O2   O 0 1 N N N 23.032 6.265  15.363 0.774  3.309  -1.110 O2   SIO 13 
SIO CM2  CM2  C 0 1 N N N 24.076 6.516  14.445 0.538  3.090  -2.502 CM2  SIO 14 
SIO C1   C1   C 0 1 N N N 24.078 7.265  17.284 1.068  2.449  1.109  C1   SIO 15 
SIO O1   O1   O 0 1 N N N 23.907 6.642  18.350 1.323  1.482  2.004  O1   SIO 16 
SIO O3   O3   O 0 1 N N N 25.168 7.823  16.998 0.932  3.592  1.477  O3   SIO 17 
SIO O6   O6   O 0 1 N N N 22.934 8.567  15.579 -0.173 1.250  -0.555 O6   SIO 18 
SIO C6   C6   C 0 1 N N R 22.761 9.737  16.377 -0.110 0.024  0.181  C6   SIO 19 
SIO C7   C7   C 0 1 N N R 22.970 10.890 15.422 -1.371 -0.798 -0.088 C7   SIO 20 
SIO O7   O7   O 0 1 N N N 21.838 11.008 14.565 -1.403 -1.185 -1.463 O7   SIO 21 
SIO C8   C8   C 0 1 N N R 24.207 10.640 14.583 -2.608 0.043  0.234  C8   SIO 22 
SIO O8   O8   O 0 1 N N N 25.255 10.246 15.474 -2.576 0.431  1.609  O8   SIO 23 
SIO C9   C9   C 0 1 N N N 24.617 11.893 13.828 -3.869 -0.779 -0.036 C9   SIO 24 
SIO O9   O9   O 0 1 N N N 24.803 12.927 14.796 -5.041 0.056  0.156  O9   SIO 25 
SIO CA9  CA9  C 0 1 N N N 25.181 14.257 14.371 -6.238 -0.519 -0.043 CA9  SIO 26 
SIO OA9  OA9  O 0 1 N N N 25.142 14.501 13.165 -6.304 -1.682 -0.366 OA9  SIO 27 
SIO CM9  CM9  C 0 1 N N N 25.587 15.252 15.436 -7.500 0.285  0.137  CM9  SIO 28 
SIO HM4  HM4  H 0 1 N N N 21.547 8.783  20.012 6.070  -2.023 0.199  HM4  SIO 29 
SIO HM4A HM4A H 0 0 N N N 20.387 9.664  21.063 5.892  -1.321 -1.427 HM4A SIO 30 
SIO HM4B HM4B H 0 0 N N N 20.653 7.903  21.296 6.826  -0.457 -0.182 HM4B SIO 31 
SIO H4   H4   H 0 1 N N N 21.805 8.510  18.743 2.494  0.296  1.018  H4   SIO 32 
SIO H5   H5   H 0 1 N N N 20.626 9.841  16.262 1.032  -1.027 -1.316 H5   SIO 33 
SIO HN5  HN5  H 0 1 N N N 22.177 10.970 18.603 0.818  -2.040 1.415  HN5  SIO 34 
SIO H11  H11  H 0 1 N N N 20.317 12.023 20.341 1.471  -4.188 1.812  H11  SIO 35 
SIO H11A H11A H 0 0 N N N 21.214 13.122 19.239 1.518  -5.153 0.317  H11A SIO 36 
SIO H11B H11B H 0 0 N N N 19.419 13.168 19.287 3.032  -4.559 1.041  H11B SIO 37 
SIO H3   H3   H 0 1 N N N 21.699 6.353  17.760 3.088  2.034  -0.624 H3   SIO 38 
SIO H3A  H3A  H 0 1 N N N 20.821 7.023  16.289 2.159  1.188  -1.884 H3A  SIO 39 
SIO HM2  HM2  H 0 1 N N N 23.663 6.581  13.428 -0.307 2.413  -2.625 HM2  SIO 40 
SIO HM2A HM2A H 0 0 N N N 24.569 7.465  14.702 0.315  4.041  -2.987 HM2A SIO 41 
SIO HM2B HM2B H 0 0 N N N 24.809 5.697  14.491 1.425  2.650  -2.956 HM2B SIO 42 
SIO HO1  HO1  H 0 1 N N N 24.705 6.670  18.865 1.390  1.749  2.932  HO1  SIO 43 
SIO H6   H6   H 0 1 N N N 23.472 9.811  17.213 -0.039 0.244  1.246  H6   SIO 44 
SIO H7   H7   H 0 1 N N N 23.098 11.819 15.997 -1.365 -1.689 0.540  H7   SIO 45 
SIO HO7  HO7  H 0 1 N N N 21.046 11.034 15.088 -1.410 -0.442 -2.081 HO7  SIO 46 
SIO H8   H8   H 0 1 N N N 24.003 9.857  13.838 -2.614 0.934  -0.394 H8   SIO 47 
SIO HO8  HO8  H 0 1 N N N 26.067 10.159 14.989 -2.568 -0.313 2.227  HO8  SIO 48 
SIO H9   H9   H 0 1 N N N 25.552 11.716 13.276 -3.850 -1.149 -1.061 H9   SIO 49 
SIO H9A  H9A  H 0 1 N N N 23.846 12.178 13.097 -3.907 -1.622 0.654  H9A  SIO 50 
SIO HM9  HM9  H 0 1 N N N 25.686 14.736 16.402 -7.243 1.304  0.427  HM9  SIO 51 
SIO HM9A HM9A H 0 0 N N N 26.551 15.707 15.164 -8.056 0.303  -0.800 HM9A SIO 52 
SIO HM9B HM9B H 0 0 N N N 24.820 16.036 15.516 -8.113 -0.170 0.915  HM9B SIO 53 
# 
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 
SIO CA4 OA4  DOUB N N 1  
SIO O4  CA4  SING N N 2  
SIO CA4 CM4  SING N N 3  
SIO CM4 HM4  SING N N 4  
SIO CM4 HM4A SING N N 5  
SIO CM4 HM4B SING N N 6  
SIO C4  O4   SING N N 7  
SIO C5  C4   SING N N 8  
SIO C3  C4   SING N N 9  
SIO C4  H4   SING N N 10 
SIO C6  C5   SING N N 11 
SIO C5  N5   SING N N 12 
SIO C5  H5   SING N N 13 
SIO N5  C10  SING N N 14 
SIO N5  HN5  SING N N 15 
SIO O10 C10  DOUB N N 16 
SIO C10 C11  SING N N 17 
SIO C11 H11  SING N N 18 
SIO C11 H11A SING N N 19 
SIO C11 H11B SING N N 20 
SIO C2  C3   SING N N 21 
SIO C3  H3   SING N N 22 
SIO C3  H3A  SING N N 23 
SIO O2  C2   SING N N 24 
SIO O6  C2   SING N N 25 
SIO C2  C1   SING N N 26 
SIO CM2 O2   SING N N 27 
SIO CM2 HM2  SING N N 28 
SIO CM2 HM2A SING N N 29 
SIO CM2 HM2B SING N N 30 
SIO O3  C1   DOUB N N 31 
SIO C1  O1   SING N N 32 
SIO O1  HO1  SING N N 33 
SIO O6  C6   SING N N 34 
SIO C7  C6   SING N N 35 
SIO C6  H6   SING N N 36 
SIO O7  C7   SING N N 37 
SIO C8  C7   SING N N 38 
SIO C7  H7   SING N N 39 
SIO O7  HO7  SING N N 40 
SIO C9  C8   SING N N 41 
SIO C8  O8   SING N N 42 
SIO C8  H8   SING N N 43 
SIO O8  HO8  SING N N 44 
SIO C9  O9   SING N N 45 
SIO C9  H9   SING N N 46 
SIO C9  H9A  SING N N 47 
SIO CA9 O9   SING N N 48 
SIO OA9 CA9  DOUB N N 49 
SIO CA9 CM9  SING N N 50 
SIO CM9 HM9  SING N N 51 
SIO CM9 HM9A SING N N 52 
SIO CM9 HM9B 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 
SIO SMILES           ACDLabs              10.04 O=C(OCC(O)C(O)C1OC(OC)(C(=O)O)CC(OC(=O)C)C1NC(=O)C)C                                                                                                                                    
SIO InChI            InChI                1.02b InChI=1/C16H25NO11/c1-7(18)17-12-11(27-9(3)20)5-16(25-4,15(23)24)28-14(12)13(22)10(21)6-26-8(2)19/h10-14,21-22H,5-6H2,1-4H3,(H,17,18)(H,23,24)/t10-,11+,12-,13-,14-,16-/m1/s1/f/h17,23H 
SIO InChIKey         InChI                1.02b PJCATKAGSUTUJA-BQPUWJIGDA                                                                                                                                                               
SIO SMILES_CANONICAL CACTVS               3.341 CO[C@@]1(C[C@H](OC(C)=O)[C@@H](NC(C)=O)[C@@H](O1)[C@H](O)[C@H](O)COC(C)=O)C(O)=O                                                                                                        
SIO SMILES           CACTVS               3.341 CO[C]1(C[CH](OC(C)=O)[CH](NC(C)=O)[CH](O1)[CH](O)[CH](O)COC(C)=O)C(O)=O                                                                                                                 
SIO 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](COC(=O)C)O)O)(C(=O)O)OC)OC(=O)C                                                                                                         
SIO SMILES           "OpenEye OEToolkits" 1.5.0 CC(=O)NC1C(CC(OC1C(C(COC(=O)C)O)O)(C(=O)O)OC)OC(=O)C                                                                                                                                    
# 
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 
SIO "SYSTEMATIC NAME" ACDLabs              10.04 "methyl 4,9-di-O-acetyl-5-(acetylamino)-3,5-dideoxy-D-glycero-alpha-D-galacto-non-2-ulopyranosidonic acid"             
SIO "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2R,4S,5R,6R)-5-acetamido-4-acetyloxy-6-[(1R,2R)-3-acetyloxy-1,2-dihydroxy-propyl]-2-methoxy-oxane-2-carboxylic acid" 
# 
