data_AKN
# 
_chem_comp.id                                    AKN 
_chem_comp.name                                  (2R)-4-AMINO-N-{(1R,2S,3S,4R,5S)-5-AMINO-2-[(3-AMINO-3-DEOXY-ALPHA-D-GLUCOPYRANOSYL)OXY]-4-[(6-AMINO-6-DEOXY-ALPHA-D-GLUCOPYRANOSYL)OXY]-3-HYDROXYCYCLOHEXYL}-2-HYDROXYBUTANAMIDE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H43 N5 O13" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         AMIKACIN 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-02-28 
_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                        585.603 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AKN 
_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        2G5Q 
_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 
AKN C1   C1   C 0 1 N N R 25.990 6.502  5.145  3.604  0.633  0.136  C1   AKN 1  
AKN O2   O2   O 0 1 N N N 27.145 7.221  4.718  2.986  -0.281 -0.771 O2   AKN 2  
AKN C3   C3   C 0 1 N N R 26.165 4.990  4.753  4.736  1.374  -0.580 C3   AKN 3  
AKN C4   C4   C 0 1 N N S 26.252 4.822  3.209  5.754  0.353  -1.097 C4   AKN 4  
AKN C5   C5   C 0 1 N N S 24.918 5.379  2.605  6.194  -0.535 0.072  C5   AKN 5  
AKN O6   O6   O 0 1 N N N 24.930 5.233  1.171  7.030  -1.588 -0.413 O6   AKN 6  
AKN C7   C7   C 0 1 N N R 24.771 6.906  3.006  4.953  -1.133 0.739  C7   AKN 7  
AKN O8   O8   O 0 1 N N N 24.769 7.041  4.500  4.129  -0.087 1.250  O8   AKN 8  
AKN C9   C9   C 0 1 N N N 23.476 7.529  2.486  5.385  -2.047 1.887  C9   AKN 9  
AKN N10  N10  N 0 1 N N N 23.024 8.686  3.314  4.206  -2.720 2.448  N10  AKN 10 
AKN C11  C11  C 0 1 N N R 29.838 10.191 6.369  -1.033 -1.578 -0.483 C11  AKN 11 
AKN N12  N12  N 0 1 N N N 30.300 11.370 7.033  -2.319 -1.957 0.108  N12  AKN 12 
AKN C13  C13  C 0 1 N N N 28.973 10.597 5.129  0.066  -2.496 0.056  C13  AKN 13 
AKN C14  C14  C 0 1 N N S 28.450 9.306  4.396  1.409  -2.101 -0.561 C14  AKN 14 
AKN N15  N15  N 0 1 N N N 27.626 9.696  3.213  2.464  -2.982 -0.043 N15  AKN 15 
AKN C16  C16  C 0 1 N N R 27.614 8.430  5.415  1.731  -0.650 -0.195 C16  AKN 16 
AKN C17  C17  C 0 1 N N S 28.520 8.076  6.643  0.633  0.268  -0.734 C17  AKN 17 
AKN O18  O18  O 0 1 N N N 27.770 7.313  7.572  0.933  1.622  -0.393 O18  AKN 18 
AKN C19  C19  C 0 1 N N S 28.998 9.376  7.345  -0.711 -0.128 -0.117 C19  AKN 19 
AKN O20  O20  O 0 1 N N N 29.826 9.036  8.464  -1.737 0.730  -0.621 O20  AKN 20 
AKN C21  C21  C 0 1 N N S 29.673 9.560  9.734  -2.635 0.980  0.462  C21  AKN 21 
AKN C22  C22  C 0 1 N N R 31.108 9.633  10.328 -3.872 1.713  -0.062 C22  AKN 22 
AKN O23  O23  O 0 1 N N N 31.888 10.488 9.553  -4.539 0.897  -1.026 O23  AKN 23 
AKN C24  C24  C 0 1 N N S 31.760 8.201  10.409 -3.435 3.027  -0.716 C24  AKN 24 
AKN N25  N25  N 0 1 N N N 33.139 8.266  10.990 -4.619 3.814  -1.087 N25  AKN 25 
AKN C26  C26  C 0 1 N N S 30.826 7.279  11.285 -2.586 3.816  0.287  C26  AKN 26 
AKN O27  O27  O 0 1 N N N 31.363 5.966  11.391 -2.044 4.975  -0.349 O27  AKN 27 
AKN C28  C28  C 0 1 N N R 29.398 7.249  10.651 -1.446 2.924  0.784  C28  AKN 28 
AKN O29  O29  O 0 1 N N N 28.842 8.646  10.533 -1.981 1.779  1.445  O29  AKN 29 
AKN C30  C30  C 0 1 N N N 28.448 6.400  11.476 -0.574 3.715  1.762  C30  AKN 30 
AKN O31  O31  O 0 1 N N N 27.436 7.166  12.154 0.549  2.920  2.149  O31  AKN 31 
AKN O32  O32  O 0 1 N N N 27.375 4.472  5.380  4.202  2.115  -1.678 O32  AKN 32 
AKN O33  O33  O 0 1 N N N 26.405 3.480  2.917  6.889  1.034  -1.636 O33  AKN 33 
AKN N34  N34  N 0 1 N N N 34.456 14.751 9.161  -7.549 -1.221 0.861  N34  AKN 34 
AKN C35  C35  C 0 1 N N N 31.156 12.306 6.513  -3.109 -2.853 -0.516 C35  AKN 35 
AKN O36  O36  O 0 1 N N N 31.655 12.237 5.400  -2.755 -3.346 -1.566 O36  AKN 36 
AKN C37  C37  C 0 1 N N R 31.414 13.433 7.527  -4.432 -3.242 0.092  C37  AKN 37 
AKN C38  C38  C 0 1 N N N 32.870 13.914 7.468  -5.361 -2.027 0.112  C38  AKN 38 
AKN C39  C39  C 0 1 N N N 33.218 15.032 8.457  -6.657 -2.388 0.841  C39  AKN 39 
AKN O40  O40  O 0 1 N N N 30.499 14.503 7.254  -5.026 -4.283 -0.687 O40  AKN 40 
AKN H1   H1   H 0 1 N N N 25.882 6.606  6.235  2.864  1.353  0.486  H1   AKN 41 
AKN H3   H3   H 0 1 N N N 25.289 4.426  5.107  5.224  2.055  0.117  H3   AKN 42 
AKN H4   H4   H 0 1 N N N 27.108 5.367  2.784  5.294  -0.262 -1.871 H4   AKN 43 
AKN H5   H5   H 0 1 N N N 24.062 4.814  3.003  6.746  0.063  0.797  H5   AKN 44 
AKN HO6  HO6  H 0 1 N N N 24.933 6.092  0.765  7.797  -1.168 -0.825 HO6  AKN 45 
AKN H7   H7   H 0 1 N N N 25.624 7.431  2.552  4.391  -1.712 0.006  H7   AKN 46 
AKN H91  1H9  H 0 1 N N N 22.692 6.759  2.530  6.086  -2.794 1.513  H91  AKN 47 
AKN H92  2H9  H 0 1 N N N 23.648 7.882  1.458  5.867  -1.453 2.663  H92  AKN 48 
AKN H101 1H10 H 0 0 N N N 23.701 9.420  3.259  4.537  -3.309 3.197  H101 AKN 49 
AKN H102 2H10 H 0 0 N N N 22.923 8.396  4.266  3.637  -2.003 2.872  H102 AKN 50 
AKN H11  H11  H 0 1 N N N 30.693 9.590  6.026  -1.088 -1.676 -1.567 H11  AKN 51 
AKN HN12 HN12 H 0 0 N N N 29.968 11.526 7.963  -2.602 -1.562 0.947  HN12 AKN 52 
AKN H131 1H13 H 0 0 N N N 29.590 11.184 4.433  0.121  -2.398 1.140  H131 AKN 53 
AKN H132 2H13 H 0 0 N N N 28.115 11.198 5.464  -0.163 -3.529 -0.204 H132 AKN 54 
AKN H14  H14  H 0 1 N N N 29.299 8.707  4.036  1.354  -2.198 -1.645 H14  AKN 55 
AKN H151 1H15 H 0 0 N N N 27.951 10.571 2.855  2.160  -3.929 -0.213 H151 AKN 56 
AKN H152 2H15 H 0 0 N N N 26.668 9.783  3.487  3.278  -2.831 -0.620 H152 AKN 57 
AKN H16  H16  H 0 1 N N N 26.737 8.980  5.786  1.787  -0.553 0.889  H16  AKN 58 
AKN H17  H17  H 0 1 N N N 29.391 7.505  6.290  0.577  0.170  -1.819 H17  AKN 59 
AKN HO18 HO18 H 0 0 N N N 27.602 6.450  7.212  1.720  1.870  -0.898 HO18 AKN 60 
AKN H19  H19  H 0 1 N N N 28.122 9.952  7.678  -0.655 -0.030 0.967  H19  AKN 61 
AKN H21  H21  H 0 1 N N N 29.188 10.547 9.727  -2.937 0.032  0.908  H21  AKN 62 
AKN H22  H22  H 0 1 N N N 31.049 10.028 11.353 -4.548 1.926  0.767  H22  AKN 63 
AKN HO23 HO23 H 0 0 N N N 32.066 11.284 10.040 -4.796 0.082  -0.573 HO23 AKN 64 
AKN H24  H24  H 0 1 N N N 31.857 7.783  9.396  -2.844 2.813  -1.607 H24  AKN 65 
AKN H251 1H25 H 0 0 N N N 33.230 9.096  11.540 -5.143 3.257  -1.745 H251 AKN 66 
AKN H252 2H25 H 0 0 N N N 33.812 8.280  10.251 -5.186 3.893  -0.257 H252 AKN 67 
AKN H26  H26  H 0 1 N N N 30.762 7.690  12.303 -3.206 4.119  1.130  H26  AKN 68 
AKN HO27 HO27 H 0 0 N N N 31.483 5.601  10.522 -1.514 5.436  0.315  HO27 AKN 69 
AKN H28  H28  H 0 1 N N N 29.491 6.805  9.649  -0.840 2.604  -0.063 H28  AKN 70 
AKN H301 1H30 H 0 0 N N N 29.048 5.896  12.248 -0.224 4.628  1.280  H301 AKN 71 
AKN H302 2H30 H 0 0 N N N 27.946 5.692  10.800 -1.159 3.971  2.645  H302 AKN 72 
AKN HO31 HO31 H 0 0 N N N 27.711 7.335  13.047 1.028  3.421  2.823  HO31 AKN 73 
AKN HO32 HO32 H 0 0 N N N 28.050 4.359  4.721  3.634  2.802  -1.302 HO32 AKN 74 
AKN HO33 HO33 H 0 0 N N N 26.440 3.362  1.975  6.566  1.579  -2.367 HO33 AKN 75 
AKN H341 1H34 H 0 0 N N N 34.645 15.488 9.811  -7.817 -1.044 -0.096 H341 AKN 76 
AKN H342 2H34 H 0 0 N N N 35.207 14.686 8.503  -8.386 -1.504 1.348  H342 AKN 77 
AKN H37  H37  H 0 1 N N N 31.250 13.058 8.548  -4.274 -3.596 1.111  H37  AKN 78 
AKN H381 1H38 H 0 0 N N N 33.022 14.329 6.461  -5.591 -1.727 -0.910 H381 AKN 79 
AKN H382 2H38 H 0 0 N N N 33.517 13.053 7.694  -4.870 -1.203 0.631  H382 AKN 80 
AKN H391 1H39 H 0 0 N N N 33.345 15.968 7.892  -6.428 -2.687 1.864  H391 AKN 81 
AKN H392 2H39 H 0 0 N N N 32.404 15.122 9.192  -7.148 -3.212 0.323  H392 AKN 82 
AKN HO40 HO40 H 0 0 N N N 30.297 14.961 8.061  -5.149 -3.929 -1.579 HO40 AKN 83 
# 
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 
AKN C1  O2   SING N N 1  
AKN C1  C3   SING N N 2  
AKN C1  O8   SING N N 3  
AKN C1  H1   SING N N 4  
AKN O2  C16  SING N N 5  
AKN C3  C4   SING N N 6  
AKN C3  O32  SING N N 7  
AKN C3  H3   SING N N 8  
AKN C4  C5   SING N N 9  
AKN C4  O33  SING N N 10 
AKN C4  H4   SING N N 11 
AKN C5  O6   SING N N 12 
AKN C5  C7   SING N N 13 
AKN C5  H5   SING N N 14 
AKN O6  HO6  SING N N 15 
AKN C7  O8   SING N N 16 
AKN C7  C9   SING N N 17 
AKN C7  H7   SING N N 18 
AKN C9  N10  SING N N 19 
AKN C9  H91  SING N N 20 
AKN C9  H92  SING N N 21 
AKN N10 H101 SING N N 22 
AKN N10 H102 SING N N 23 
AKN C11 N12  SING N N 24 
AKN C11 C13  SING N N 25 
AKN C11 C19  SING N N 26 
AKN C11 H11  SING N N 27 
AKN N12 C35  SING N N 28 
AKN N12 HN12 SING N N 29 
AKN C13 C14  SING N N 30 
AKN C13 H131 SING N N 31 
AKN C13 H132 SING N N 32 
AKN C14 N15  SING N N 33 
AKN C14 C16  SING N N 34 
AKN C14 H14  SING N N 35 
AKN N15 H151 SING N N 36 
AKN N15 H152 SING N N 37 
AKN C16 C17  SING N N 38 
AKN C16 H16  SING N N 39 
AKN C17 O18  SING N N 40 
AKN C17 C19  SING N N 41 
AKN C17 H17  SING N N 42 
AKN O18 HO18 SING N N 43 
AKN C19 O20  SING N N 44 
AKN C19 H19  SING N N 45 
AKN O20 C21  SING N N 46 
AKN C21 C22  SING N N 47 
AKN C21 O29  SING N N 48 
AKN C21 H21  SING N N 49 
AKN C22 O23  SING N N 50 
AKN C22 C24  SING N N 51 
AKN C22 H22  SING N N 52 
AKN O23 HO23 SING N N 53 
AKN C24 N25  SING N N 54 
AKN C24 C26  SING N N 55 
AKN C24 H24  SING N N 56 
AKN N25 H251 SING N N 57 
AKN N25 H252 SING N N 58 
AKN C26 O27  SING N N 59 
AKN C26 C28  SING N N 60 
AKN C26 H26  SING N N 61 
AKN O27 HO27 SING N N 62 
AKN C28 O29  SING N N 63 
AKN C28 C30  SING N N 64 
AKN C28 H28  SING N N 65 
AKN C30 O31  SING N N 66 
AKN C30 H301 SING N N 67 
AKN C30 H302 SING N N 68 
AKN O31 HO31 SING N N 69 
AKN O32 HO32 SING N N 70 
AKN O33 HO33 SING N N 71 
AKN N34 C39  SING N N 72 
AKN N34 H341 SING N N 73 
AKN N34 H342 SING N N 74 
AKN C35 O36  DOUB N N 75 
AKN C35 C37  SING N N 76 
AKN C37 C38  SING N N 77 
AKN C37 O40  SING N N 78 
AKN C37 H37  SING N N 79 
AKN C38 C39  SING N N 80 
AKN C38 H381 SING N N 81 
AKN C38 H382 SING N N 82 
AKN C39 H391 SING N N 83 
AKN C39 H392 SING N N 84 
AKN O40 HO40 SING N N 85 
# 
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 
AKN SMILES           ACDLabs              10.04 O=C(NC3C(OC1OC(C(O)C(N)C1O)CO)C(O)C(OC2OC(CN)C(O)C(O)C2O)C(N)C3)C(O)CCN 
AKN InChI            InChI                1.02b 
InChI=1/C22H43N5O13/c23-2-1-8(29)20(36)27-7-3-6(25)18(39-22-16(34)15(33)13(31)9(4-24)37-22)17(35)19(7)40-21-14(32)11(26)12(30)10(5-28)38-21/h6-19,21-22,28-35H,1-5,23-26H2,(H,27,36)/t6-,7+,8+,9+,10+,11-,12+,13+,14+,15-,16+,17-,18+,19-,21+,22+/m0/s1/f/h27H 
AKN InChIKey         InChI                1.02b LKCWBDHBTVXHDL-WOWDYPDIDW 
AKN SMILES_CANONICAL CACTVS               3.341 NCC[C@@H](O)C(=O)N[C@@H]1C[C@H](N)[C@@H](O[C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O[C@H]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O 
AKN SMILES           CACTVS               3.341 NCC[CH](O)C(=O)N[CH]1C[CH](N)[CH](O[CH]2O[CH](CN)[CH](O)[CH](O)[CH]2O)[CH](O)[CH]1O[CH]3O[CH](CO)[CH](O)[CH](N)[CH]3O 
AKN SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1NC(=O)[C@@H](CCN)O)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)N)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)O)N 
AKN SMILES           "OpenEye OEToolkits" 1.5.0 C1C(C(C(C(C1NC(=O)C(CCN)O)OC2C(C(C(C(O2)CO)O)N)O)O)OC3C(C(C(C(O3)CN)O)O)O)N 
# 
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 
AKN "SYSTEMATIC NAME" ACDLabs              10.04 (2R)-4-amino-N-{(1R,2S,3S,4R,5S)-5-amino-2-[(3-amino-3-deoxy-alpha-D-glucopyranosyl)oxy]-4-[(6-amino-6-deoxy-alpha-D-glucopyranosyl)oxy]-3-hydroxycyclohexyl}-2-hydroxybutanamide 
AKN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 
(2R)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxy-oxan-2-yl]oxy-3-hydroxy-cyclohexyl]-2-hydroxy-butanamide 
# 
