data_H3S
# 
_chem_comp.id                                    H3S 
_chem_comp.name                                  "HEPARIN DISACCHARIDE III-S" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C12 H16 N O16 S2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    -3 
_chem_comp.pdbx_initial_date                     2004-08-03 
_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                        494.383 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     H3S 
_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        1U4M 
_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 
H3S C1  C1  C 0  1 N N S 18.805 7.800  34.808 -0.644 0.312  -0.331 C1  H3S 1  
H3S C2  C2  C 0  1 N N R 18.826 8.998  33.752 -0.880 1.404  -1.376 C2  H3S 2  
H3S O3  O3  O 0  1 N N N 18.597 8.289  36.147 0.609  0.535  0.320  O3  H3S 3  
H3S C4  C4  C 0  1 N N R 17.762 6.780  34.314 -1.774 0.357  0.704  C4  H3S 4  
H3S O5  O5  O 0  1 N N N 19.057 8.547  32.376 -2.116 1.169  -2.048 O5  H3S 5  
H3S C6  C6  C 0  1 N N N 19.889 10.059 34.142 0.262  1.389  -2.394 C6  H3S 6  
H3S C7  C7  C 0  1 N N R 17.264 8.909  36.402 1.544  -0.376 -0.261 C7  H3S 7  
H3S C8  C8  C 0  1 N N R 18.096 6.315  32.880 -3.116 0.274  -0.034 C8  H3S 8  
H3S O9  O9  O 0  1 N N N 17.748 5.675  35.230 -1.652 -0.747 1.602  O9  H3S 9  
H3S C10 C10 C 0  1 N N S 18.088 7.539  31.929 -3.166 1.368  -1.103 C10 H3S 10 
H3S O11 O11 O 0  1 N N N 21.226 9.567  33.941 0.108  2.485  -3.298 O11 H3S 11 
H3S C12 C12 C 0  1 N N R 16.733 8.584  37.851 2.962  -0.022 0.208  C12 H3S 12 
H3S O13 O13 O 0  1 N N N 17.366 10.387 36.287 1.231  -1.703 0.149  O13 H3S 13 
H3S N14 N14 N 0  1 N N N 17.113 5.344  32.421 -4.213 0.468  0.918  N14 H3S 14 
H3S O15 O15 O 0  1 N N N 16.757 8.119  31.881 -3.009 2.645  -0.481 O15 H3S 15 
H3S C17 C17 C 0  1 N N S 17.716 9.228  38.919 3.942  -0.881 -0.605 C17 H3S 16 
H3S O18 O18 O 0  1 N N N 15.431 9.210  38.018 3.222  1.364  -0.025 O18 H3S 17 
H3S C19 C19 C 0  1 N N N 18.063 11.117 37.234 2.143  -2.564 -0.336 C19 H3S 18 
H3S S20 S20 S 0  1 N N N 17.497 3.745  32.461 -5.639 -0.349 0.714  S20 H3S 19 
H3S C24 C24 C 0  1 N N N 18.259 10.614 38.497 3.382  -2.278 -0.691 C24 H3S 20 
H3S O25 O25 O 0  1 N N N 18.823 8.342  39.137 5.214  -0.909 0.044  O25 H3S 21 
H3S S26 S26 S 0  1 N N N 14.238 8.224  37.867 4.140  1.833  1.095  S26 H3S 22 
H3S C27 C27 C 0  1 N N N 18.575 12.445 36.844 1.717  -3.965 -0.486 C27 H3S 23 
H3S O28 O28 O 0  1 N N N 17.757 3.342  33.804 -5.333 -1.760 0.885  O28 H3S 24 
H3S O29 O29 O 0  1 N N N 16.402 2.992  31.956 -6.547 0.148  1.737  O29 H3S 25 
H3S O30 O30 O -1 1 N N N 18.850 3.490  31.534 -6.100 -0.042 -0.631 O30 H3S 26 
H3S O31 O31 O 0  1 N N N 13.036 8.967  38.059 5.460  1.301  0.794  O31 H3S 27 
H3S O32 O32 O 0  1 N N N 14.209 7.648  36.548 4.111  3.287  1.068  O32 H3S 28 
H3S O33 O33 O -1 1 N N N 14.315 7.026  39.013 3.594  1.291  2.329  O33 H3S 29 
H3S O34 O34 O -1 1 N N N 18.221 12.931 35.793 0.581  -4.296 -0.175 O34 H3S 30 
H3S O35 O35 O 0  1 N N N 19.452 13.159 37.661 2.500  -4.799 -0.921 O35 H3S 31 
H3S H1  H1  H 0  1 N N N 19.789 7.280  34.872 -0.633 -0.664 -0.816 H1  H3S 32 
H3S H2  H2  H 0  1 N N N 17.810 9.456  33.784 -0.915 2.375  -0.884 H2  H3S 33 
H3S H4  H4  H 0  1 N N N 16.751 7.248  34.280 -1.722 1.291  1.263  H4  H3S 34 
H3S H61 1H6 H 0  1 N N N 19.740 10.420 35.187 0.240  0.453  -2.951 H61 H3S 35 
H3S H62 2H6 H 0  1 N N N 19.723 11.020 33.602 1.215  1.480  -1.872 H62 H3S 36 
H3S H7  H7  H 0  1 N N N 16.560 8.489  35.647 1.492  -0.308 -1.347 H7  H3S 37 
H3S H8  H8  H 0  1 N N N 19.104 5.838  32.880 -3.212 -0.703 -0.507 H8  H3S 38 
H3S HO9 HO9 H 0  1 N N N 17.105 5.046  34.925 -2.389 -0.684 2.225  HO9 H3S 39 
H3S H10 H10 H 0  1 N N N 18.378 7.197  30.908 -4.127 1.330  -1.615 H10 H3S 40 
H3S H11 H11 H 0  1 N N N 21.877 10.217 34.180 0.847  2.439  -3.921 H11 H3S 41 
H3S H12 H12 H 0  1 N N N 16.669 7.480  37.990 3.066  -0.245 1.269  H12 H3S 42 
H3S H14 H14 H 0  1 N N N 16.825 5.590  31.474 -4.104 1.074  1.667  H14 H3S 43 
H3S H15 H15 H 0  1 N N N 16.130 7.467  31.592 -3.051 3.306  -1.186 H15 H3S 44 
H3S H17 H17 H 0  1 N N N 17.124 9.378  39.852 4.049  -0.465 -1.607 H17 H3S 45 
H3S H24 H24 H 0  1 N N N 18.831 11.297 39.148 4.018  -3.072 -1.054 H24 H3S 46 
H3S H25 H25 H 0  1 N N N 19.411 8.727  39.776 5.788  -1.474 -0.490 H25 H3S 47 
# 
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 
H3S C1  C2  SING N N 1  
H3S C1  O3  SING N N 2  
H3S C1  C4  SING N N 3  
H3S C1  H1  SING N N 4  
H3S C2  O5  SING N N 5  
H3S C2  C6  SING N N 6  
H3S C2  H2  SING N N 7  
H3S O3  C7  SING N N 8  
H3S C4  C8  SING N N 9  
H3S C4  O9  SING N N 10 
H3S C4  H4  SING N N 11 
H3S O5  C10 SING N N 12 
H3S C6  O11 SING N N 13 
H3S C6  H61 SING N N 14 
H3S C6  H62 SING N N 15 
H3S C7  C12 SING N N 16 
H3S C7  O13 SING N N 17 
H3S C7  H7  SING N N 18 
H3S C8  C10 SING N N 19 
H3S C8  N14 SING N N 20 
H3S C8  H8  SING N N 21 
H3S O9  HO9 SING N N 22 
H3S C10 O15 SING N N 23 
H3S C10 H10 SING N N 24 
H3S O11 H11 SING N N 25 
H3S C12 C17 SING N N 26 
H3S C12 O18 SING N N 27 
H3S C12 H12 SING N N 28 
H3S O13 C19 SING N N 29 
H3S N14 S20 SING N N 30 
H3S N14 H14 SING N N 31 
H3S O15 H15 SING N N 32 
H3S C17 C24 SING N N 33 
H3S C17 O25 SING N N 34 
H3S C17 H17 SING N N 35 
H3S O18 S26 SING N N 36 
H3S C19 C24 DOUB N N 37 
H3S C19 C27 SING N N 38 
H3S S20 O28 DOUB N N 39 
H3S S20 O29 DOUB N N 40 
H3S S20 O30 SING N N 41 
H3S C24 H24 SING N N 42 
H3S O25 H25 SING N N 43 
H3S S26 O31 DOUB N N 44 
H3S S26 O32 DOUB N N 45 
H3S S26 O33 SING N N 46 
H3S C27 O34 SING N N 47 
H3S C27 O35 DOUB N N 48 
# 
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 
H3S SMILES           ACDLabs              10.04 [O-]S(=O)(=O)OC2C(O)C=C(OC2OC1C(OC(O)C(NS([O-])(=O)=O)C1O)CO)C([O-])=O 
H3S InChI            InChI                1.02b 
InChI=1/C12H19NO16S2/c14-2-5-9(7(16)6(11(19)26-5)13-30(20,21)22)28-12-8(29-31(23,24)25)3(15)1-4(27-12)10(17)18/h1,3,5-9,11-16,19H,2H2,(H,17,18)(H,20,21,22)(H,23,24,25)/p-3/t3-,5+,6+,7+,8+,9+,11-,12-/m0/s1/fC12H16NO16S2/q-3 
H3S InChIKey         InChI                1.02b GSYQGRODWXMUOO-YLPGCDAFDV 
H3S SMILES_CANONICAL CACTVS               3.341 OC[C@H]1O[C@H](O)[C@H](N[S]([O-])(=O)=O)[C@@H](O)[C@@H]1O[C@@H]2OC(=C[C@H](O)[C@H]2O[S]([O-])(=O)=O)C([O-])=O 
H3S SMILES           CACTVS               3.341 OC[CH]1O[CH](O)[CH](N[S]([O-])(=O)=O)[CH](O)[CH]1O[CH]2OC(=C[CH](O)[CH]2O[S]([O-])(=O)=O)C([O-])=O 
H3S SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C1=C(O[C@H]([C@@H]([C@H]1O)OS(=O)(=O)[O-])O[C@@H]2[C@H](O[C@@H]([C@@H]([C@H]2O)NS(=O)(=O)[O-])O)CO)C(=O)[O-] 
H3S SMILES           "OpenEye OEToolkits" 1.5.0 C1=C(OC(C(C1O)OS(=O)(=O)[O-])OC2C(OC(C(C2O)NS(=O)(=O)[O-])O)CO)C(=O)[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 
H3S "SYSTEMATIC NAME" ACDLabs              10.04 "(2R,3R,4S)-2-{[(2R,3S,4R,5R,6S)-4,6-dihydroxy-2-(hydroxymethyl)-5-(sulfonatoamino)tetrahydro-2H-pyran-3-yl]oxy}-4-hydroxy-3-(sulfonatooxy)-3,4-dihydro-2H-pyran-6-carboxylate (non-preferred name)" 
H3S "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (4S,5R,6R)-6-[(2R,3S,4R,5R,6S)-4,6-dihydroxy-2-(hydroxymethyl)-5-(sulfonatoamino)oxan-3-yl]oxy-4-hydroxy-5-sulfonatooxy-5,6-dihydro-4H-pyran-2-carboxylate                                           
# 
