data_MUS
# 
_chem_comp.id                                    MUS 
_chem_comp.name                                  "4-METHYL-2-OXO-2H-CHROMEN-7-YL 5-(ACETYLAMINO)-3,5-DIDEOXY-L-ERYTHRO-NON-2-ULOPYRANOSIDONIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H25 N O11" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "METHYLUMBELLIFERYL SIALIC ACID" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-01-19 
_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                        467.423 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     MUS 
_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        1S0J 
_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 
MUS O16  O16  O 0 1 N N N 7.045  -19.812 -2.436  -0.851 4.355  0.300  O16  MUS 1  
MUS C16  C16  C 0 1 N N N 6.066  -19.205 -3.270  0.469  3.837  0.478  C16  MUS 2  
MUS C15  C15  C 0 1 N N R 6.671  -18.018 -4.028  0.499  2.364  0.065  C15  MUS 3  
MUS O15  O15  O 0 1 N N N 7.020  -16.990 -3.124  0.236  2.257  -1.336 O15  MUS 4  
MUS C14  C14  C 0 1 N N R 7.933  -18.503 -4.728  1.878  1.776  0.371  C14  MUS 5  
MUS O14  O14  O 0 1 N N N 7.580  -19.726 -5.377  2.140  1.883  1.772  O14  MUS 6  
MUS C13  C13  C 0 1 N N R 8.441  -17.452 -5.717  1.907  0.303  -0.042 C13  MUS 7  
MUS O13  O13  O 0 1 N N N 7.292  -17.102 -6.467  0.837  -0.390 0.598  O13  MUS 8  
MUS C12  C12  C 0 1 N N R 9.564  -18.000 -6.621  3.245  -0.315 0.370  C12  MUS 9  
MUS N12  N12  N 0 1 N N N 10.738 -18.444 -5.867  4.341  0.416  -0.271 N12  MUS 10 
MUS C17  C17  C 0 1 N N N 10.954 -19.738 -5.669  5.569  0.414  0.285  C17  MUS 11 
MUS C18  C18  C 0 1 N N N 12.248 -20.106 -5.021  6.696  1.166  -0.374 C18  MUS 12 
MUS O17  O17  O 0 1 N N N 10.125 -20.629 -5.975  5.766  -0.194 1.316  O17  MUS 13 
MUS C11  C11  C 0 1 N N S 9.979  -16.925 -7.653  3.278  -1.782 -0.076 C11  MUS 14 
MUS O11  O11  O 0 1 N N N 10.233 -17.597 -8.874  4.456  -2.411 0.432  O11  MUS 15 
MUS C10  C10  C 0 1 N N N 8.854  -15.946 -7.945  2.035  -2.490 0.475  C10  MUS 16 
MUS C9   C9   C 0 1 N N S 7.474  -16.557 -7.740  0.788  -1.708 0.054  C9   MUS 17 
MUS C19  C19  C 0 1 N N N 6.405  -15.500 -7.976  0.732  -1.628 -1.450 C19  MUS 18 
MUS O19  O19  O 0 1 N N N 5.565  -15.222 -7.083  1.795  -1.183 -2.139 O19  MUS 19 
MUS O20  O20  O 0 1 N N N 6.395  -14.928 -9.062  -0.270 -1.963 -2.036 O20  MUS 20 
MUS O9   O9   O 0 1 N N N 7.250  -17.597 -8.693  -0.378 -2.378 0.536  O9   MUS 21 
MUS C7   C7   C 0 1 Y N N 6.003  -18.147 -8.849  -1.433 -1.563 0.280  C7   MUS 22 
MUS C6   C6   C 0 1 Y N N 5.517  -19.180 -8.038  -1.239 -0.388 -0.444 C6   MUS 23 
MUS C8   C8   C 0 1 Y N N 5.371  -17.840 -10.039 -2.695 -1.909 0.734  C8   MUS 24 
MUS C8A  C8A  C 0 1 Y N N 4.213  -18.494 -10.401 -3.773 -1.075 0.477  C8A  MUS 25 
MUS C4A  C4A  C 0 1 Y N N 3.683  -19.561 -9.555  -3.570 0.110  -0.254 C4A  MUS 26 
MUS C5   C5   C 0 1 Y N N 4.374  -19.928 -8.395  -2.289 0.442  -0.710 C5   MUS 27 
MUS O1   O1   O 0 1 Y N N 3.557  -18.113 -11.544 -5.010 -1.392 0.915  O1   MUS 28 
MUS C2   C2   C 0 1 Y N N 2.383  -18.732 -11.923 -6.064 -0.598 0.670  C2   MUS 29 
MUS O2   O2   O 0 1 N N N 1.845  -18.311 -12.971 -7.162 -0.924 1.084  O2   MUS 30 
MUS C3   C3   C 0 1 Y N N 1.808  -19.767 -11.176 -5.933 0.604  -0.056 C3   MUS 31 
MUS C4   C4   C 0 1 Y N N 2.421  -20.211 -10.001 -4.715 0.981  -0.525 C4   MUS 32 
MUS CM4  CM4  C 0 1 N N N 1.851  -21.292 -9.171  -4.548 2.261  -1.302 CM4  MUS 33 
MUS H16  H16  H 0 1 N N N 6.670  -20.548 -1.966  -0.826 5.283  0.571  H16  MUS 34 
MUS H161 1H16 H 0 0 N N N 5.156  -18.911 -2.696  0.756  3.926  1.525  H161 MUS 35 
MUS H162 2H16 H 0 0 N N N 5.595  -19.942 -3.961  1.167  4.402  -0.140 H162 MUS 36 
MUS H15  H15  H 0 1 N N N 5.931  -17.621 -4.761  -0.262 1.815  0.620  H15  MUS 37 
MUS H2   H2   H 0 1 N N N 7.395  -16.254 -3.594  0.930  2.754  -1.790 H2   MUS 38 
MUS H14  H14  H 0 1 N N N 8.768  -18.671 -4.009  2.638  2.324  -0.184 H14  MUS 39 
MUS H1   H1   H 0 1 N N N 8.368  -20.029 -5.814  1.446  1.385  2.225  H1   MUS 40 
MUS H13  H13  H 0 1 N N N 8.898  -16.576 -5.200  1.793  0.228  -1.123 H13  MUS 41 
MUS H12  H12  H 0 1 N N N 9.154  -18.896 -7.142  3.354  -0.261 1.453  H12  MUS 42 
MUS H4   H4   H 0 1 N N N 11.438 -17.823 -5.461  4.183  0.902  -1.095 H4   MUS 43 
MUS H181 1H18 H 0 0 N N N 12.355 -19.556 -4.057  7.605  1.049  0.217  H181 MUS 44 
MUS H182 2H18 H 0 0 N N N 12.430 -21.193 -4.855  6.860  0.770  -1.376 H182 MUS 45 
MUS H183 3H18 H 0 0 N N N 13.095 -19.668 -5.599  6.438  2.223  -0.438 H183 MUS 46 
MUS H11  H11  H 0 1 N N N 10.855 -16.370 -7.244  3.276  -1.833 -1.164 H11  MUS 47 
MUS H7   H7   H 0 1 N N N 10.488 -16.937 -9.508  4.436  -3.329 0.128  H7   MUS 48 
MUS H101 1H10 H 0 0 N N N 8.953  -15.517 -8.969  1.983  -3.502 0.074  H101 MUS 49 
MUS H102 2H10 H 0 0 N N N 8.971  -15.013 -7.346  2.090  -2.529 1.563  H102 MUS 50 
MUS H19  H19  H 0 1 N N N 4.898  -14.562 -7.230  1.759  -1.132 -3.104 H19  MUS 51 
MUS H6   H6   H 0 1 N N N 6.046  -19.409 -7.098  -0.250 -0.132 -0.796 H6   MUS 52 
MUS H8   H8   H 0 1 N N N 5.794  -17.068 -10.704 -2.839 -2.824 1.290  H8   MUS 53 
MUS H5   H5   H 0 1 N N N 4.029  -20.778 -7.783  -2.132 1.352  -1.270 H5   MUS 54 
MUS H3   H3   H 0 1 N N N 0.868  -20.235 -11.515 -6.799 1.224  -0.238 H3   MUS 55 
MUS HM41 1HM4 H 0 0 N N N 1.716  -20.916 -8.130  -4.687 2.062  -2.365 HM41 MUS 56 
MUS HM42 2HM4 H 0 0 N N N 0.905  -21.779 -9.505  -5.288 2.988  -0.969 HM42 MUS 57 
MUS HM43 3HM4 H 0 0 N N N 2.627  -22.077 -9.017  -3.547 2.659  -1.135 HM43 MUS 58 
# 
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 
MUS O16 C16  SING N N 1  
MUS O16 H16  SING N N 2  
MUS C16 C15  SING N N 3  
MUS C16 H161 SING N N 4  
MUS C16 H162 SING N N 5  
MUS C15 O15  SING N N 6  
MUS C15 C14  SING N N 7  
MUS C15 H15  SING N N 8  
MUS O15 H2   SING N N 9  
MUS C14 O14  SING N N 10 
MUS C14 C13  SING N N 11 
MUS C14 H14  SING N N 12 
MUS O14 H1   SING N N 13 
MUS C13 O13  SING N N 14 
MUS C13 C12  SING N N 15 
MUS C13 H13  SING N N 16 
MUS O13 C9   SING N N 17 
MUS C12 N12  SING N N 18 
MUS C12 C11  SING N N 19 
MUS C12 H12  SING N N 20 
MUS N12 C17  SING N N 21 
MUS N12 H4   SING N N 22 
MUS C17 C18  SING N N 23 
MUS C17 O17  DOUB N N 24 
MUS C18 H181 SING N N 25 
MUS C18 H182 SING N N 26 
MUS C18 H183 SING N N 27 
MUS C11 O11  SING N N 28 
MUS C11 C10  SING N N 29 
MUS C11 H11  SING N N 30 
MUS O11 H7   SING N N 31 
MUS C10 C9   SING N N 32 
MUS C10 H101 SING N N 33 
MUS C10 H102 SING N N 34 
MUS C9  C19  SING N N 35 
MUS C9  O9   SING N N 36 
MUS C19 O19  SING N N 37 
MUS C19 O20  DOUB N N 38 
MUS O19 H19  SING N N 39 
MUS O9  C7   SING N N 40 
MUS C7  C6   DOUB Y N 41 
MUS C7  C8   SING Y N 42 
MUS C6  C5   SING Y N 43 
MUS C6  H6   SING N N 44 
MUS C8  C8A  DOUB Y N 45 
MUS C8  H8   SING N N 46 
MUS C8A C4A  SING Y N 47 
MUS C8A O1   SING Y N 48 
MUS C4A C5   DOUB Y N 49 
MUS C4A C4   SING Y N 50 
MUS C5  H5   SING N N 51 
MUS O1  C2   SING Y N 52 
MUS C2  O2   DOUB N N 53 
MUS C2  C3   SING Y N 54 
MUS C3  C4   DOUB Y N 55 
MUS C3  H3   SING N N 56 
MUS C4  CM4  SING N N 57 
MUS CM4 HM41 SING N N 58 
MUS CM4 HM42 SING N N 59 
MUS CM4 HM43 SING N N 60 
# 
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 
MUS SMILES           ACDLabs              10.04 O=C3Oc2c(ccc(OC1(OC(C(O)C(O)CO)C(NC(=O)C)C(O)C1)C(=O)O)c2)C(=C3)C 
MUS InChI            InChI                1.02b 
InChI=1/C21H25NO11/c1-9-5-16(27)31-15-6-11(3-4-12(9)15)32-21(20(29)30)7-13(25)17(22-10(2)24)19(33-21)18(28)14(26)8-23/h3-6,13-14,17-19,23,25-26,28H,7-8H2,1-2H3,(H,22,24)(H,29,30)/t13-,14+,17+,18+,19+,21+/m0/s1/f/h22,29H 
MUS InChIKey         InChI                1.02b KKDWIUJBUSOPGC-YBLVEZJZDS 
MUS SMILES_CANONICAL CACTVS               3.341 CC(=O)N[C@@H]1[C@@H](O)C[C@](O[C@H]1[C@H](O)[C@H](O)CO)(Oc2ccc3C(=CC(=O)Oc3c2)C)C(O)=O 
MUS SMILES           CACTVS               3.341 CC(=O)N[CH]1[CH](O)C[C](O[CH]1[CH](O)[CH](O)CO)(Oc2ccc3C(=CC(=O)Oc3c2)C)C(O)=O 
MUS SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC1=CC(=O)Oc2c1ccc(c2)O[C@@]3(C[C@@H]([C@H]([C@@H](O3)[C@@H]([C@@H](CO)O)O)NC(=O)C)O)C(=O)O 
MUS SMILES           "OpenEye OEToolkits" 1.5.0 CC1=CC(=O)Oc2c1ccc(c2)OC3(CC(C(C(O3)C(C(CO)O)O)NC(=O)C)O)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 
MUS "SYSTEMATIC NAME" ACDLabs              10.04 "4-methyl-2-oxo-2H-chromen-7-yl 5-(acetylamino)-3,5-dideoxy-D-glycero-alpha-D-galacto-non-2-ulopyranosidonic acid"                 
MUS "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S,4S,5R,6R)-5-acetamido-4-hydroxy-2-(4-methyl-2-oxo-chromen-7-yl)oxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid" 
# 
