data_AO3
# 
_chem_comp.id                                    AO3 
_chem_comp.name                                  ALLOSAMIDIN 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C25 H42 N4 O14" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         
(3AR,4R,5R,6S,6AS)-2-(DIMETHYLAMINO)-3A,5,6,6A-TETRAHYDRO-4-HYDROXY-6-(HYDROXYMETHYL)-4H-CYCLOPENTOXAZOL-5-YL-2-(ACETYLAMINO)-4-O-[2-(ACETYLAMINO)-2-DEOXY-BETA-D-ALLOPYRANOSYL]-2-DEOXY-BETA-D-ALLOPYRANOSIDE 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-08-18 
_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                        622.619 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AO3 
_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        1X6N 
_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 
AO3 C1   C1   C 0 1 N N S -2.647  34.465 66.205 3.935  0.010  0.122  C1   AO3 1  
AO3 C2   C2   C 0 1 N N R -2.560  34.000 64.733 5.331  -0.590 -0.060 C2   AO3 2  
AO3 C3   C3   C 0 1 N N S -1.339  33.204 64.392 6.340  0.239  0.741  C3   AO3 3  
AO3 C4   C4   C 0 1 N N S -0.108  33.970 64.939 6.204  1.709  0.327  C4   AO3 4  
AO3 C5   C5   C 0 1 N N R -0.251  34.353 66.423 4.743  2.136  0.479  C5   AO3 5  
AO3 C6   C6   C 0 1 N N N 0.892   35.114 67.146 4.604  3.612  0.100  C6   AO3 6  
AO3 C7   C7   C 0 1 N N N -4.610  33.518 63.516 4.950  -2.975 -0.390 C7   AO3 7  
AO3 C8   C8   C 0 1 N N N -5.771  32.636 63.203 4.957  -4.396 0.110  C8   AO3 8  
AO3 N2   N2   N 0 1 N N N -3.699  33.155 64.417 5.336  -1.973 0.425  N2   AO3 9  
AO3 O3   O3   O 0 1 N N N -1.400  31.911 64.977 6.073  0.108  2.139  O3   AO3 10 
AO3 O4   O4   O 0 1 N N N 1.025   33.139 64.791 7.030  2.521  1.164  O4   AO3 11 
AO3 O5   O5   O 0 1 N N N -1.447  35.185 66.593 3.917  1.347  -0.375 O5   AO3 12 
AO3 O6   O6   O 0 1 N N N 0.565   35.372 68.519 3.267  4.046  0.358  O6   AO3 13 
AO3 O7   O7   O 0 1 N N N -4.494  34.572 62.912 4.598  -2.732 -1.525 O7   AO3 14 
AO3 C11  C11  C 0 1 N N R -6.405  36.009 69.550 -1.102 -0.254 -0.735 C11  AO3 15 
AO3 C12  C12  C 0 1 N N R -4.993  35.544 70.005 -0.291 1.039  -0.852 C12  AO3 16 
AO3 C13  C13  C 0 1 N N S -3.934  35.815 68.902 1.156  0.689  -1.216 C13  AO3 17 
AO3 C14  C14  C 0 1 N N S -4.492  35.087 67.594 1.687  -0.323 -0.194 C14  AO3 18 
AO3 C15  C15  C 0 1 N N R -5.909  35.580 67.271 0.727  -1.513 -0.126 C15  AO3 19 
AO3 C16  C16  C 0 1 N N N -6.659  35.007 66.051 1.266  -2.543 0.868  C16  AO3 20 
AO3 C17  C17  C 0 1 N N N -4.441  35.736 72.406 -1.889 2.717  -1.606 C17  AO3 21 
AO3 C18  C18  C 0 1 N N N -4.381  36.709 73.576 -2.482 3.589  -2.682 C18  AO3 22 
AO3 N12  N12  N 0 1 N N N -4.661  36.300 71.219 -0.868 1.886  -1.899 N12  AO3 23 
AO3 O13  O13  O 0 1 N N N -3.732  37.214 68.631 1.202  0.117  -2.525 O13  AO3 24 
AO3 O14  O14  O 0 1 N N N -3.661  35.364 66.430 2.982  -0.776 -0.595 O14  AO3 25 
AO3 O15  O15  O 0 1 N N N -6.783  35.333 68.377 -0.561 -1.070 0.301  O15  AO3 26 
AO3 O16  O16  O 0 1 N N N -7.983  35.601 65.903 0.431  -3.703 0.852  O16  AO3 27 
AO3 O17  O17  O 0 1 N N N -4.299  34.503 72.557 -2.329 2.763  -0.477 O17  AO3 28 
AO3 C21  C21  C 0 1 N N S -10.598 36.221 71.967 -5.554 -1.362 0.316  C21  AO3 29 
AO3 C22  C22  C 0 1 N N R -10.825 36.352 70.474 -4.598 -1.476 1.537  C22  AO3 30 
AO3 C23  C23  C 0 1 N N R -9.560  35.712 69.948 -3.212 -1.786 0.952  C23  AO3 31 
AO3 C24  C24  C 0 1 N N R -8.528  36.335 70.762 -3.188 -1.166 -0.452 C24  AO3 32 
AO3 C25  C25  C 0 1 N N S -9.082  36.097 72.173 -4.645 -0.907 -0.860 C25  AO3 33 
AO3 C26  C26  C 0 1 N N N -8.576  37.037 73.273 -4.982 -1.710 -2.118 C26  AO3 34 
AO3 C27  C27  C 0 1 N N N -12.138 34.684 71.267 -5.649 0.512  1.564  C27  AO3 35 
AO3 C28  C28  C 0 1 N N N -13.506 32.829 70.486 -5.119 2.581  2.782  C28  AO3 36 
AO3 C29  C29  C 0 1 N N N -13.468 33.372 72.843 -7.133 2.446  1.245  C29  AO3 37 
AO3 N22  N22  N 0 1 N N N -11.856 35.398 70.104 -4.626 -0.104 2.073  N22  AO3 38 
AO3 N27  N27  N 0 1 N N N -13.006 33.656 71.519 -5.960 1.818  1.857  N27  AO3 39 
AO3 O23  O23  O 0 1 N N N -9.659  35.919 68.533 -3.019 -3.199 0.870  O23  AO3 40 
AO3 O24  O24  O 0 1 N N N -7.297  35.680 70.560 -2.461 0.064  -0.429 O24  AO3 41 
AO3 O26  O26  O 0 1 N N N -8.346  38.402 72.627 -6.300 -1.375 -2.557 O26  AO3 42 
AO3 O27  O27  O 0 1 N N N -11.415 35.108 72.342 -6.381 -0.249 0.727  O27  AO3 43 
AO3 H2   H2   H 0 1 N N N -2.806  33.524 66.782 3.678  0.014  1.182  H2   AO3 44 
AO3 H6   H6   H 0 1 N N N -2.531  34.945 64.143 5.601  -0.573 -1.116 H6   AO3 45 
AO3 H3   H3   H 0 1 N N N -1.267  33.075 63.286 7.351  -0.109 0.528  H3   AO3 46 
AO3 H4   H4   H 0 1 N N N -0.010  34.919 64.362 6.512  1.825  -0.712 H4   AO3 47 
AO3 H5   H5   H 0 1 N N N -0.268  33.345 66.899 4.430  1.998  1.515  H5   AO3 48 
AO3 H61  1H6  H 0 1 N N N 1.863   34.575 67.052 5.300  4.206  0.691  H61  AO3 49 
AO3 H62  2H6  H 0 1 N N N 1.161   36.052 66.607 4.828  3.737  -0.960 H62  AO3 50 
AO3 H81  1H8  H 0 1 N N N -6.533  32.939 62.448 5.300  -4.417 1.144  H81  AO3 51 
AO3 H82  2H8  H 0 1 N N N -5.377  31.633 62.913 3.948  -4.805 0.054  H82  AO3 52 
AO3 H83  3H8  H 0 1 N N N -6.299  32.406 64.157 5.626  -4.995 -0.508 H83  AO3 53 
AO3 HN2  HN2  H 0 1 N N N -3.869  32.249 64.855 5.618  -2.167 1.333  HN2  AO3 54 
AO3 HO3  HO3  H 0 1 N N N -0.625  31.405 64.760 6.723  0.655  2.600  HO3  AO3 55 
AO3 HO4  HO4  H 0 1 N N N 1.779   33.608 65.126 6.908  3.436  0.874  HO4  AO3 56 
AO3 HO6  HO6  H 0 1 N N N 1.264   35.837 68.961 3.223  4.979  0.106  HO6  AO3 57 
AO3 H11  H11  H 0 1 N N N -6.400  37.105 69.349 -1.061 -0.794 -1.681 H11  AO3 58 
AO3 H12  H12  H 0 1 N N N -4.992  34.446 70.200 -0.310 1.570  0.099  H12  AO3 59 
AO3 H13  H13  H 0 1 N N N -2.940  35.433 69.233 1.768  1.590  -1.190 H13  AO3 60 
AO3 H14  H14  H 0 1 N N N -4.487  33.993 67.809 1.753  0.149  0.786  H14  AO3 61 
AO3 H15  H15  H 0 1 N N N -5.694  36.648 67.033 0.644  -1.969 -1.112 H15  AO3 62 
AO3 H161 1H16 H 0 0 N N N -6.058  35.114 65.117 2.281  -2.822 0.587  H161 AO3 63 
AO3 H162 2H16 H 0 0 N N N -6.715  33.894 66.094 1.271  -2.113 1.870  H162 AO3 64 
AO3 H181 1H18 H 0 0 N N N -4.196  36.237 74.569 -1.961 3.411  -3.623 H181 AO3 65 
AO3 H182 2H18 H 0 0 N N N -3.622  37.502 73.379 -3.539 3.350  -2.802 H182 AO3 66 
AO3 H183 3H18 H 0 0 N N N -5.306  37.329 73.609 -2.376 4.637  -2.400 H183 AO3 67 
AO3 H8   H8   H 0 1 N N N -4.574  37.316 71.239 -0.516 1.850  -2.802 H8   AO3 68 
AO3 H7   H7   H 0 1 N N N -3.084  37.379 67.956 0.860  0.786  -3.134 H7   AO3 69 
AO3 H16  H16  H 0 1 N N N -8.444  35.248 65.151 0.805  -4.325 1.491  H16  AO3 70 
AO3 H21  H21  H 0 1 N N N -10.893 37.076 72.618 -6.112 -2.274 0.102  H21  AO3 71 
AO3 H22  H22  H 0 1 N N N -11.070 37.385 70.135 -4.923 -2.220 2.264  H22  AO3 72 
AO3 H23  H23  H 0 1 N N N -9.345  34.621 70.035 -2.436 -1.338 1.572  H23  AO3 73 
AO3 H24  H24  H 0 1 N N N -8.326  37.408 70.540 -2.724 -1.858 -1.155 H24  AO3 74 
AO3 H25  H25  H 0 1 N N N -8.737  35.110 72.563 -4.792 0.156  -1.049 H25  AO3 75 
AO3 H261 1H26 H 0 0 N N N -9.253  37.080 74.157 -4.266 -1.472 -2.904 H261 AO3 76 
AO3 H262 2H26 H 0 0 N N N -7.675  36.646 73.802 -4.934 -2.775 -1.892 H262 AO3 77 
AO3 H281 1H28 H 0 0 N N N -14.213 31.991 70.691 -5.520 3.589  2.890  H281 AO3 78 
AO3 H282 2H28 H 0 0 N N N -13.973 33.488 69.718 -5.108 2.089  3.755  H282 AO3 79 
AO3 H283 3H28 H 0 0 N N N -12.633 32.409 69.933 -4.103 2.634  2.391  H283 AO3 80 
AO3 H291 1H29 H 0 0 N N N -14.175 32.534 73.048 -7.218 3.475  1.594  H291 AO3 81 
AO3 H292 2H29 H 0 0 N N N -12.574 33.233 73.495 -7.024 2.438  0.160  H292 AO3 82 
AO3 H293 3H29 H 0 0 N N N -13.914 34.306 73.257 -8.029 1.893  1.524  H293 AO3 83 
AO3 H1   H1   H 0 1 N N N -8.864  35.516 68.202 -3.069 -3.541 1.773  H1   AO3 84 
AO3 H26  H26  H 0 1 N N N -8.032  38.984 73.308 -6.473 -1.902 -3.349 H26  AO3 85 
# 
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 
AO3 C1  C2   SING N N 1  
AO3 C1  O5   SING N N 2  
AO3 C1  O14  SING N N 3  
AO3 C1  H2   SING N N 4  
AO3 C2  C3   SING N N 5  
AO3 C2  N2   SING N N 6  
AO3 C2  H6   SING N N 7  
AO3 C3  C4   SING N N 8  
AO3 C3  O3   SING N N 9  
AO3 C3  H3   SING N N 10 
AO3 C4  C5   SING N N 11 
AO3 C4  O4   SING N N 12 
AO3 C4  H4   SING N N 13 
AO3 C5  C6   SING N N 14 
AO3 C5  O5   SING N N 15 
AO3 C5  H5   SING N N 16 
AO3 C6  O6   SING N N 17 
AO3 C6  H61  SING N N 18 
AO3 C6  H62  SING N N 19 
AO3 C7  C8   SING N N 20 
AO3 C7  N2   SING N N 21 
AO3 C7  O7   DOUB N N 22 
AO3 C8  H81  SING N N 23 
AO3 C8  H82  SING N N 24 
AO3 C8  H83  SING N N 25 
AO3 N2  HN2  SING N N 26 
AO3 O3  HO3  SING N N 27 
AO3 O4  HO4  SING N N 28 
AO3 O6  HO6  SING N N 29 
AO3 C11 C12  SING N N 30 
AO3 C11 O15  SING N N 31 
AO3 C11 O24  SING N N 32 
AO3 C11 H11  SING N N 33 
AO3 C12 C13  SING N N 34 
AO3 C12 N12  SING N N 35 
AO3 C12 H12  SING N N 36 
AO3 C13 C14  SING N N 37 
AO3 C13 O13  SING N N 38 
AO3 C13 H13  SING N N 39 
AO3 C14 C15  SING N N 40 
AO3 C14 O14  SING N N 41 
AO3 C14 H14  SING N N 42 
AO3 C15 C16  SING N N 43 
AO3 C15 O15  SING N N 44 
AO3 C15 H15  SING N N 45 
AO3 C16 O16  SING N N 46 
AO3 C16 H161 SING N N 47 
AO3 C16 H162 SING N N 48 
AO3 C17 C18  SING N N 49 
AO3 C17 N12  SING N N 50 
AO3 C17 O17  DOUB N N 51 
AO3 C18 H181 SING N N 52 
AO3 C18 H182 SING N N 53 
AO3 C18 H183 SING N N 54 
AO3 N12 H8   SING N N 55 
AO3 O13 H7   SING N N 56 
AO3 O16 H16  SING N N 57 
AO3 C21 C22  SING N N 58 
AO3 C21 C25  SING N N 59 
AO3 C21 O27  SING N N 60 
AO3 C21 H21  SING N N 61 
AO3 C22 C23  SING N N 62 
AO3 C22 N22  SING N N 63 
AO3 C22 H22  SING N N 64 
AO3 C23 C24  SING N N 65 
AO3 C23 O23  SING N N 66 
AO3 C23 H23  SING N N 67 
AO3 C24 C25  SING N N 68 
AO3 C24 O24  SING N N 69 
AO3 C24 H24  SING N N 70 
AO3 C25 C26  SING N N 71 
AO3 C25 H25  SING N N 72 
AO3 C26 O26  SING N N 73 
AO3 C26 H261 SING N N 74 
AO3 C26 H262 SING N N 75 
AO3 C27 N22  DOUB N N 76 
AO3 C27 N27  SING N N 77 
AO3 C27 O27  SING N N 78 
AO3 C28 N27  SING N N 79 
AO3 C28 H281 SING N N 80 
AO3 C28 H282 SING N N 81 
AO3 C28 H283 SING N N 82 
AO3 C29 N27  SING N N 83 
AO3 C29 H291 SING N N 84 
AO3 C29 H292 SING N N 85 
AO3 C29 H293 SING N N 86 
AO3 O23 H1   SING N N 87 
AO3 O26 H26  SING N N 88 
# 
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 
AO3 SMILES           ACDLabs              10.04 O=C(NC4C(O)C(O)C(OC4OC3C(OC(OC1C(O)C2N=C(OC2C1CO)N(C)C)C(NC(=O)C)C3O)CO)CO)C 
AO3 InChI            InChI                1.02b 
;InChI=1/C25H42N4O14/c1-8(33)26-14-17(36)16(35)11(6-31)39-23(14)42-22-12(7-32)40-24(15(19(22)38)27-9(2)34)41-21-10(5-30)20-13(18(21)37)28-25(43-20)29(3)4/h10-24,30-32,35-38H,5-7H2,1-4H3,(H,26,33)(H,27,34)/t10-,11+,12+,13+,14+,15+,16+,17-,18+,19-,20-,21+,22+,23-,24-/m0/s1/f/h26-27H
;
AO3 InChIKey         InChI                1.02b MDWNFWDBQGOKNZ-YMPPTUKHDL 
AO3 SMILES_CANONICAL CACTVS               3.341 CN(C)C1=N[C@@H]2[C@@H](O)[C@H](O[C@@H]3O[C@H](CO)[C@@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@@H](O)[C@H]4NC(C)=O)[C@@H](O)[C@H]3NC(C)=O)[C@@H](CO)[C@@H]2O1 
AO3 SMILES           CACTVS               3.341 CN(C)C1=N[CH]2[CH](O)[CH](O[CH]3O[CH](CO)[CH](O[CH]4O[CH](CO)[CH](O)[CH](O)[CH]4NC(C)=O)[CH](O)[CH]3NC(C)=O)[CH](CO)[CH]2O1 
AO3 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(=O)N[C@@H]1[C@@H]([C@@H]([C@H](O[C@H]1O[C@@H]2[C@H](O[C@H]([C@@H]([C@@H]2O)NC(=O)C)O[C@@H]3[C@H]([C@H]4[C@@H]([C@H]3O)N=C(O4)N(C)C)CO)CO)CO)O)O 
AO3 SMILES           "OpenEye OEToolkits" 1.5.0 CC(=O)NC1C(C(C(OC1OC2C(OC(C(C2O)NC(=O)C)OC3C(C4C(C3O)N=C(O4)N(C)C)CO)CO)CO)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 
AO3 "SYSTEMATIC NAME" ACDLabs              10.04 
"(3aR,4R,5R,6S,6aS)-2-(dimethylamino)-4-hydroxy-6-(hydroxymethyl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]oxazol-5-yl 2-(acetylamino)-4-O-[2-(acetylamino)-2-deoxy-beta-D-allopyranosyl]-2-deoxy-beta-D-allopyranoside" 
AO3 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 
;N-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4S,5R,6R)-6-[[(3aR,4R,5R,6S,6aS)-2-dimethylamino-4-hydroxy-6-(hydroxymethyl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]oxazol-5-yl]oxy]-5-acetamido-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanamide
;
# 
