data_GUM
# 
_chem_comp.id                                    GUM 
_chem_comp.name                                  4-METHYL-UMBELLIFERYL-N-ACETYL-CHITOBIOSE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C26 H34 N2 O13" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "4-METHYLUMBELLIFERYL CHITOBIOSE" 
_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                        582.554 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GUM 
_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        1BB7 
_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 
GUM O1   O1   O 0 1 Y N N 47.956 44.633 25.657 -2.116 0.393  4.447  O1   GUM 1  
GUM C2   C2   C 0 1 Y N N 47.227 40.711 25.388 0.917  -1.124 5.824  C2   GUM 2  
GUM O2   O2   O 0 1 N N N 49.859 45.753 24.988 -4.111 0.695  5.345  O2   GUM 3  
GUM C3   C3   C 0 1 Y N N 45.931 40.809 25.988 1.764  -0.989 4.763  C3   GUM 4  
GUM C4   C4   C 0 1 Y N N 45.202 41.911 26.485 1.327  -0.391 3.582  C4   GUM 5  
GUM C5   C5   C 0 1 Y N N 45.643 43.283 26.494 0.030  0.079  3.470  C5   GUM 6  
GUM C6   C6   C 0 1 Y N N 46.994 43.428 25.913 -0.845 -0.054 4.537  C6   GUM 7  
GUM C7   C7   C 0 1 Y N N 49.726 43.422 24.686 -2.594 -0.319 6.692  C7   GUM 8  
GUM C8   C8   C 0 1 Y N N 49.171 42.126 24.741 -1.330 -0.790 6.848  C8   GUM 9  
GUM C1   C1   C 0 1 Y N N 47.828 42.075 25.332 -0.399 -0.659 5.726  C1   GUM 10 
GUM C9   C9   C 0 1 Y N N 49.283 44.716 25.075 -2.975 0.276  5.472  C9   GUM 11 
GUM C10  C10  C 0 1 N N N 49.820 40.857 24.248 -0.898 -1.432 8.142  C10  GUM 12 
GUM O3   O3   O 0 1 N N N 43.933 41.766 27.001 2.182  -0.264 2.535  O3   GUM 13 
GUM C11  C11  C 0 1 N N S 43.085 42.647 27.560 1.422  0.252  1.441  C11  GUM 14 
GUM C12  C12  C 0 1 N N R 41.476 42.598 27.645 2.363  0.594  0.284  C12  GUM 15 
GUM C13  C13  C 0 1 N N R 40.752 43.997 27.996 1.543  1.178  -0.870 C13  GUM 16 
GUM C14  C14  C 0 1 N N S 41.601 44.571 29.209 0.415  0.199  -1.214 C14  GUM 17 
GUM C15  C15  C 0 1 N N R 43.052 44.788 28.723 -0.379 -0.114 0.054  C15  GUM 18 
GUM O4   O4   O 0 1 N N N 43.694 43.545 28.476 0.474  -0.725 1.020  O4   GUM 19 
GUM N1   N1   N 0 1 N N N 40.888 42.025 26.441 3.353  1.579  0.729  N1   GUM 20 
GUM C16  C16  C 0 1 N N N 44.020 45.584 29.599 -1.527 -1.067 -0.284 C16  GUM 21 
GUM O5   O5   O 0 1 N N N 43.661 46.017 30.911 -2.344 -1.260 0.872  O5   GUM 22 
GUM C17  C17  C 0 1 N N N 40.529 40.742 26.521 4.525  1.168  1.252  C17  GUM 23 
GUM O6   O6   O 0 1 N N N 40.646 39.934 27.364 4.761  -0.016 1.353  O6   GUM 24 
GUM C18  C18  C 0 1 N N N 39.851 40.721 25.138 5.542  2.181  1.710  C18  GUM 25 
GUM O7   O7   O 0 1 N N N 40.904 45.827 29.256 -0.450 0.789  -2.186 O7   GUM 26 
GUM O8   O8   O 0 1 N N N 39.564 43.543 28.652 2.381  1.364  -2.013 O8   GUM 27 
GUM C19  C19  C 0 1 N N S 40.580 46.201 30.574 -0.507 -0.114 -3.292 C19  GUM 28 
GUM C20  C20  C 0 1 N N R 40.235 47.675 30.714 -1.563 0.366  -4.289 C20  GUM 29 
GUM C21  C21  C 0 1 N N R 39.442 48.031 31.963 -1.639 -0.625 -5.456 C21  GUM 30 
GUM C22  C22  C 0 1 N N S 38.147 47.240 32.098 -0.232 -0.810 -6.034 C22  GUM 31 
GUM C23  C23  C 0 1 N N R 38.229 45.732 31.826 0.722  -1.204 -4.905 C23  GUM 32 
GUM O9   O9   O 0 1 N N N 39.375 45.487 30.929 0.768  -0.167 -3.927 O9   GUM 33 
GUM N2   N2   N 0 1 N N N 41.534 48.375 30.785 -2.867 0.442  -3.625 N2   GUM 34 
GUM O10  O10  O 0 1 N N N 37.471 47.437 33.362 -0.254 -1.840 -7.025 O10  GUM 35 
GUM C24  C24  C 0 1 N N N 36.972 45.157 31.290 2.124  -1.423 -5.477 C24  GUM 36 
GUM O11  O11  O 0 1 N N N 36.025 45.942 30.590 3.017  -1.791 -4.424 O11  GUM 37 
GUM C25  C25  C 0 1 N N N 41.928 49.294 29.889 -3.250 1.584  -3.021 C25  GUM 38 
GUM O12  O12  O 0 1 N N N 41.486 49.307 28.731 -2.515 2.549  -3.027 O12  GUM 39 
GUM C26  C26  C 0 1 N N N 42.978 50.295 30.382 -4.591 1.662  -2.337 C26  GUM 40 
GUM O13  O13  O 0 1 N N N 39.083 49.425 31.960 -2.512 -0.113 -6.465 O13  GUM 41 
GUM H2   H2   H 0 1 N N N 47.675 39.766 25.036 1.261  -1.589 6.736  H2   GUM 42 
GUM H3   H3   H 0 1 N N N 45.390 39.852 26.086 2.780  -1.348 4.838  H3   GUM 43 
GUM H5   H5   H 0 1 N N N 45.030 44.109 26.891 -0.299 0.546  2.553  H5   GUM 44 
GUM H7   H7   H 0 1 N N N 50.733 43.424 24.237 -3.306 -0.400 7.500  H7   GUM 45 
GUM H101 1H10 H 0 0 N N N 49.381 39.832 24.291 -1.731 -1.432 8.844  H101 GUM 46 
GUM H102 2H10 H 0 0 N N N 50.090 41.037 23.181 -0.583 -2.458 7.951  H102 GUM 47 
GUM H103 3H10 H 0 0 N N N 50.811 40.795 24.754 -0.066 -0.869 8.566  H103 GUM 48 
GUM H11  H11  H 0 1 N N N 42.851 42.849 26.488 0.896  1.153  1.759  H11  GUM 49 
GUM H12  H12  H 0 1 N N N 41.283 41.932 28.518 2.873  -0.308 -0.050 H12  GUM 50 
GUM H13  H13  H 0 1 N N N 40.621 44.698 27.139 1.117  2.136  -0.570 H13  GUM 51 
GUM H14  H14  H 0 1 N N N 41.673 43.981 30.152 0.840  -0.720 -1.616 H14  GUM 52 
GUM H15  H15  H 0 1 N N N 42.866 45.414 27.819 -0.785 0.810  0.464  H15  GUM 53 
GUM HN1  HN1  H 0 1 N N N 40.730 42.512 25.559 3.164  2.527  0.648  HN1  GUM 54 
GUM H161 1H16 H 0 0 N N N 44.967 45.001 29.678 -2.128 -0.640 -1.086 H161 GUM 55 
GUM H162 2H16 H 0 0 N N N 44.346 46.479 29.020 -1.120 -2.026 -0.606 H162 GUM 56 
GUM HO5  HO5  H 0 1 N N N 44.262 46.511 31.455 -3.053 -1.865 0.615  HO5  GUM 57 
GUM H181 1H18 H 0 0 N N N 39.551 39.649 25.204 6.419  1.664  2.099  H181 GUM 58 
GUM H182 2H18 H 0 0 N N N 39.057 41.476 24.930 5.835  2.808  0.868  H182 GUM 59 
GUM H183 3H18 H 0 0 N N N 40.449 41.045 24.254 5.109  2.803  2.493  H183 GUM 60 
GUM HO8  HO8  H 0 1 N N N 39.137 44.366 28.858 3.075  1.985  -1.752 HO8  GUM 61 
GUM H19  H19  H 0 1 N N N 41.466 45.977 31.212 -0.776 -1.107 -2.934 H19  GUM 62 
GUM H20  H20  H 0 1 N N N 39.587 47.964 29.854 -1.288 1.351  -4.666 H20  GUM 63 
GUM H21  H21  H 0 1 N N N 40.114 47.780 32.816 -2.017 -1.583 -5.098 H21  GUM 64 
GUM H22  H22  H 0 1 N N N 37.551 47.687 31.268 0.102  0.122  -6.486 H22  GUM 65 
GUM H23  H23  H 0 1 N N N 38.382 45.206 32.797 0.373  -2.126 -4.439 H23  GUM 66 
GUM HN2  HN2  H 0 1 N N N 42.221 48.208 31.519 -3.454 -0.329 -3.620 HN2  GUM 67 
GUM HOA  HOA  H 0 1 N N N 36.663 46.943 33.446 0.648  -1.924 -7.361 HOA  GUM 68 
GUM H241 1H24 H 0 0 N N N 37.244 44.293 30.639 2.092  -2.219 -6.221 H241 GUM 69 
GUM H242 2H24 H 0 0 N N N 36.441 44.656 32.133 2.474  -0.503 -5.945 H242 GUM 70 
GUM HOB  HOB  H 0 1 N N N 35.219 45.573 30.246 3.887  -1.919 -4.826 HOB  GUM 71 
GUM H261 1H26 H 0 0 N N N 43.305 51.058 29.637 -4.723 2.656  -1.910 H261 GUM 72 
GUM H262 2H26 H 0 0 N N N 42.617 50.798 31.309 -5.381 1.471  -3.064 H262 GUM 73 
GUM H263 3H26 H 0 0 N N N 43.864 49.750 30.782 -4.638 0.916  -1.544 H263 GUM 74 
GUM HOD  HOD  H 0 1 N N N 38.587 49.647 32.739 -2.530 -0.766 -7.177 HOD  GUM 75 
# 
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 
GUM O1  C6   SING Y N 1  
GUM O1  C9   SING Y N 2  
GUM C2  C3   DOUB Y N 3  
GUM C2  C1   SING Y N 4  
GUM C2  H2   SING N N 5  
GUM O2  C9   DOUB N N 6  
GUM C3  C4   SING Y N 7  
GUM C3  H3   SING N N 8  
GUM C4  C5   DOUB Y N 9  
GUM C4  O3   SING N N 10 
GUM C5  C6   SING Y N 11 
GUM C5  H5   SING N N 12 
GUM C6  C1   DOUB Y N 13 
GUM C7  C8   DOUB Y N 14 
GUM C7  C9   SING Y N 15 
GUM C7  H7   SING N N 16 
GUM C8  C1   SING Y N 17 
GUM C8  C10  SING N N 18 
GUM C10 H101 SING N N 19 
GUM C10 H102 SING N N 20 
GUM C10 H103 SING N N 21 
GUM O3  C11  SING N N 22 
GUM C11 C12  SING N N 23 
GUM C11 O4   SING N N 24 
GUM C11 H11  SING N N 25 
GUM C12 C13  SING N N 26 
GUM C12 N1   SING N N 27 
GUM C12 H12  SING N N 28 
GUM C13 C14  SING N N 29 
GUM C13 O8   SING N N 30 
GUM C13 H13  SING N N 31 
GUM C14 C15  SING N N 32 
GUM C14 O7   SING N N 33 
GUM C14 H14  SING N N 34 
GUM C15 O4   SING N N 35 
GUM C15 C16  SING N N 36 
GUM C15 H15  SING N N 37 
GUM N1  C17  SING N N 38 
GUM N1  HN1  SING N N 39 
GUM C16 O5   SING N N 40 
GUM C16 H161 SING N N 41 
GUM C16 H162 SING N N 42 
GUM O5  HO5  SING N N 43 
GUM C17 O6   DOUB N N 44 
GUM C17 C18  SING N N 45 
GUM C18 H181 SING N N 46 
GUM C18 H182 SING N N 47 
GUM C18 H183 SING N N 48 
GUM O7  C19  SING N N 49 
GUM O8  HO8  SING N N 50 
GUM C19 C20  SING N N 51 
GUM C19 O9   SING N N 52 
GUM C19 H19  SING N N 53 
GUM C20 C21  SING N N 54 
GUM C20 N2   SING N N 55 
GUM C20 H20  SING N N 56 
GUM C21 C22  SING N N 57 
GUM C21 O13  SING N N 58 
GUM C21 H21  SING N N 59 
GUM C22 C23  SING N N 60 
GUM C22 O10  SING N N 61 
GUM C22 H22  SING N N 62 
GUM C23 O9   SING N N 63 
GUM C23 C24  SING N N 64 
GUM C23 H23  SING N N 65 
GUM N2  C25  SING N N 66 
GUM N2  HN2  SING N N 67 
GUM O10 HOA  SING N N 68 
GUM C24 O11  SING N N 69 
GUM C24 H241 SING N N 70 
GUM C24 H242 SING N N 71 
GUM O11 HOB  SING N N 72 
GUM C25 O12  DOUB N N 73 
GUM C25 C26  SING N N 74 
GUM C26 H261 SING N N 75 
GUM C26 H262 SING N N 76 
GUM C26 H263 SING N N 77 
GUM O13 HOD  SING N N 78 
# 
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 
GUM SMILES           ACDLabs              10.04 O=C(NC4C(O)C(O)C(OC4OC3C(OC(Oc1cc2OC(=O)C=C(c2cc1)C)C(NC(=O)C)C3O)CO)CO)C 
GUM InChI            InChI                1.02b 
;InChI=1/C26H34N2O13/c1-10-6-18(33)38-15-7-13(4-5-14(10)15)37-25-20(28-12(3)32)23(36)24(17(9-30)40-25)41-26-19(27-11(2)31)22(35)21(34)16(8-29)39-26/h4-7,16-17,19-26,29-30,34-36H,8-9H2,1-3H3,(H,27,31)(H,28,32)/t16-,17-,19-,20-,21-,22-,23-,24-,25-,26+/m1/s1/f/h27-28H
;
GUM InChIKey         InChI                1.02b UPSFMJHZUCSEHU-FDLQYEGVDO 
GUM SMILES_CANONICAL CACTVS               3.341 CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]2[C@H](O)[C@@H](NC(C)=O)[C@@H](O[C@@H]2CO)Oc3ccc4C(=CC(=O)Oc4c3)C 
GUM SMILES           CACTVS               3.341 CC(=O)N[CH]1[CH](O)[CH](O)[CH](CO)O[CH]1O[CH]2[CH](O)[CH](NC(C)=O)[CH](O[CH]2CO)Oc3ccc4C(=CC(=O)Oc4c3)C 
GUM SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC1=CC(=O)Oc2c1ccc(c2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)NC(=O)C)O)NC(=O)C 
GUM SMILES           "OpenEye OEToolkits" 1.5.0 CC1=CC(=O)Oc2c1ccc(c2)OC3C(C(C(C(O3)CO)OC4C(C(C(C(O4)CO)O)O)NC(=O)C)O)NC(=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 
GUM "SYSTEMATIC NAME" ACDLabs              10.04 "4-methyl-2-oxo-2H-chromen-7-yl 2-(acetylamino)-4-O-[2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl]-2-deoxy-beta-D-glucopyranoside"                                                  
GUM "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 N-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)-2-(4-methyl-2-oxo-chromen-7-yl)oxy-oxan-3-yl]ethanamide 
# 
