data_AKN
#

_chem_comp.id                                   AKN
_chem_comp.name                                 
;(2S)-N-[(1R,2S,3S,4R,5S)-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]oxy-5-azanyl-2-[(2S,3R,4S,5S
,6R)-4-azanyl-6-(hydroxymethyl)-3,5-bis(oxidanyl)oxan-2-yl]oxy-3-oxidanyl-cyclohexyl]-4-azanyl-2-oxidanyl-butanamide
;

_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                   2020-06-17
_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       Corina
_chem_comp.pdbx_ideal_coordinates_missing_flag  N
_chem_comp.pdbx_model_coordinates_db_code       4P20
_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  25.987   6.448   5.168   3.606   0.410   0.388  C1   AKN   1  
AKN  C3   C2   C  0  1  N  N  R  26.160   4.927   4.776   4.838   1.068  -0.240  C3   AKN   2  
AKN  C4   C3   C  0  1  N  N  S  26.265   4.770   3.233   5.690  -0.007  -0.921  C4   AKN   3  
AKN  C5   C4   C  0  1  N  N  S  24.921   5.332   2.611   6.064  -1.076   0.110  C5   AKN   4  
AKN  C7   C5   C  0  1  N  N  R  24.776   6.873   3.008   4.786  -1.652   0.724  C7   AKN   5  
AKN  C9   C6   C  0  1  N  N  N  23.487   7.493   2.473   5.152  -2.678   1.798  C9   AKN   6  
AKN  O6   O1   O  0  1  N  N  N  24.950   5.191   1.170   6.799  -2.121  -0.531  O6   AKN   7  
AKN  O2   O2   O  0  1  N  N  N  27.149   7.172   4.719   2.811  -0.188  -0.638  O2   AKN   8  
AKN  O8   O3   O  0  1  N  N  N  24.754   6.999   4.523   4.025  -0.595   1.314  O8   AKN   9  
AKN  N10  N1   N  0  1  N  N  N  23.020   8.627   3.330   3.929  -3.316   2.303  N10  AKN  10  
AKN  C11  C7   C  0  1  N  N  R  29.721  10.353   6.178  -1.298  -1.195  -0.758  C11  AKN  11  
AKN  N12  N2   N  0  1  N  N  N  30.099  11.587   6.780  -2.624  -1.626  -0.309  N12  AKN  12  
AKN  C13  C8   C  0  1  N  N  N  28.799  10.656   4.955  -0.285  -2.312  -0.503  C13  AKN  13  
AKN  C14  C9   C  0  1  N  N  S  28.344   9.312   4.271   1.100  -1.862  -0.972  C14  AKN  14  
AKN  N15  N3   N  0  1  N  N  N  27.464   9.623   3.100   2.073  -2.935  -0.727  N15  AKN  15  
AKN  C16  C10  C  0  1  N  N  R  27.583   8.419   5.361   1.518  -0.609  -0.200  C16  AKN  16  
AKN  C17  C11  C  0  1  N  N  S  28.569   8.145   6.568   0.504   0.509  -0.456  C17  AKN  17  
AKN  O18  O4   O  0  1  N  N  N  27.906   7.365   7.549   0.894   1.679   0.266  O18  AKN  18  
AKN  C19  C12  C  0  1  N  N  S  28.999   9.488   7.213  -0.881   0.059   0.014  C19  AKN  19  
AKN  O20  O5   O  0  1  N  N  N  29.889   9.224   8.302  -1.827   1.102  -0.225  O20  AKN  20  
AKN  C21  C13  C  0  1  N  N  S  29.709   9.688   9.581  -2.348   1.698   0.965  C21  AKN  21  
AKN  C22  C14  C  0  1  N  N  R  31.124   9.766  10.218  -3.717   2.317   0.669  C22  AKN  22  
AKN  O23  O6   O  0  1  N  N  N  31.925  10.627   9.472  -4.595   1.311   0.159  O23  AKN  23  
AKN  C24  C15  C  0  1  N  N  S  31.787   8.330  10.339  -3.551   3.428  -0.373  C24  AKN  24  
AKN  N25  N4   N  0  1  N  N  N  33.139   8.429  10.967  -4.847   4.078  -0.607  N25  AKN  25  
AKN  C26  C16  C  0  1  N  N  S  30.823   7.400  11.198  -2.548   4.459   0.152  C26  AKN  26  
AKN  O27  O7   O  0  1  N  N  N  31.375   6.089  11.341  -2.331   5.463  -0.842  O27  AKN  27  
AKN  C28  C17  C  0  1  N  N  R  29.418   7.349  10.491  -1.225   3.757   0.468  C28  AKN  28  
AKN  O29  O8   O  0  1  N  N  N  28.854   8.757  10.339  -1.454   2.716   1.419  O29  AKN  29  
AKN  C30  C18  C  0  1  N  N  N  28.436   6.491  11.284  -0.236   4.770   1.049  C30  AKN  30  
AKN  O31  O9   O  0  1  N  N  N  27.506   7.243  12.099   1.031   4.140   1.246  O31  AKN  31  
AKN  O32  O10  O  0  1  N  N  N  27.361   4.419   5.406   4.423   2.033  -1.208  O32  AKN  32  
AKN  O33  O11  O  0  1  N  N  N  26.418   3.427   2.939   6.878   0.588  -1.448  O33  AKN  33  
AKN  N37  N5   N  0  1  N  N  N  34.428  14.890   9.205  -5.865  -5.062   2.172  N37  AKN  34  
AKN  C35  C19  C  0  1  N  N  N  31.356  12.187   6.427  -3.411  -2.350  -1.129  C35  AKN  35  
AKN  O36  O12  O  0  1  N  N  N  32.236  11.509   5.782  -3.021  -2.645  -2.239  O36  AKN  36  
AKN  C37  C20  C  0  1  N  N  S  31.579  13.663   6.874  -4.775  -2.794  -0.667  C37  AKN  37  
AKN  C38  C21  C  0  1  N  N  N  32.746  13.665   7.907  -4.626  -3.770   0.501  C38  AKN  38  
AKN  C39  C22  C  0  1  N  N  N  33.341  15.037   8.216  -6.009  -4.124   1.050  C39  AKN  39  
AKN  O40  O13  O  0  1  N  N  N  30.562  14.150   7.502  -5.456  -3.440  -1.745  O40  AKN  40  
AKN  H1   H1   H  0  1  N  N  N  25.892   6.517   6.262   3.018   1.163   0.911  H1   AKN  41  
AKN  H2   H2   H  0  1  N  N  N  25.279   4.372   5.131   5.423   1.560   0.537  H2   AKN  42  
AKN  H3   H3   H  0  1  N  N  N  27.109   5.370   2.862   5.122  -0.464  -1.731  H3   AKN  43  
AKN  H4   H4   H  0  1  N  N  N  24.073   4.777   3.038   6.675  -0.628   0.894  H4   AKN  44  
AKN  H5   H5   H  0  1  N  N  N  25.641   7.421   2.606   4.194  -2.135  -0.054  H5   AKN  45  
AKN  H6   H6   H  0  1  N  N  N  23.668   7.867   1.454   5.807  -3.436   1.368  H6   AKN  46  
AKN  H7   H7   H  0  1  N  N  N  22.704   6.721   2.447   5.665  -2.177   2.619  H7   AKN  47  
AKN  H8   H8   H  0  1  N  N  N  25.036   4.273   0.943   7.623  -1.827  -0.942  H8   AKN  48  
AKN  H9   H9   H  0  1  N  N  N  22.177   9.007   2.950   3.401  -3.733   1.550  H9   AKN  49  
AKN  H10  H10  H  0  1  N  N  N  22.848   8.295   4.257   4.144  -3.999   3.014  H10  AKN  50  
AKN  H12  H12  H  0  1  N  N  N  30.610   9.813   5.820  -1.331  -0.971  -1.825  H12  AKN  51  
AKN  H13  H13  H  0  1  N  N  N  29.496  12.032   7.442  -2.936  -1.390   0.578  H13  AKN  52  
AKN  H14  H14  H  0  1  N  N  N  29.352  11.266   4.225  -0.252  -2.536   0.563  H14  AKN  53  
AKN  H15  H15  H  0  1  N  N  N  27.911  11.208   5.297  -0.582  -3.205  -1.053  H15  AKN  54  
AKN  H16  H16  H  0  1  N  N  N  29.237   8.765   3.933   1.067  -1.638  -2.038  H16  AKN  55  
AKN  H17  H17  H  0  1  N  N  N  27.174   8.771   2.665   1.727  -3.821  -1.064  H17  AKN  56  
AKN  H18  H18  H  0  1  N  N  N  26.659  10.128   3.413   2.966  -2.715  -1.140  H18  AKN  57  
AKN  H20  H20  H  0  1  N  N  N  26.714   8.982   5.732   1.550  -0.833   0.866  H20  AKN  58  
AKN  H21  H21  H  0  1  N  N  N  29.460   7.626   6.186   0.472   0.733  -1.522  H21  AKN  59  
AKN  H22  H22  H  0  1  N  N  N  28.496   7.199   8.275   1.688   2.109  -0.082  H22  AKN  60  
AKN  H23  H23  H  0  1  N  N  N  28.102  10.018   7.566  -0.848  -0.166   1.080  H23  AKN  61  
AKN  H24  H24  H  0  1  N  N  N  29.262  10.693   9.585  -2.453   0.935   1.737  H24  AKN  62  
AKN  H25  H25  H  0  1  N  N  N  31.008  10.158  11.239  -4.133   2.735   1.585  H25  AKN  63  
AKN  H26  H26  H  0  1  N  N  N  32.790  10.674   9.863  -4.742   0.573   0.766  H26  AKN  64  
AKN  H27  H27  H  0  1  N  N  N  31.877   7.901   9.330  -3.183   3.001  -1.306  H27  AKN  65  
AKN  H28  H28  H  0  1  N  N  N  33.543   7.517  11.036  -5.528   3.415  -0.947  H28  AKN  66  
AKN  H29  H29  H  0  1  N  N  N  33.726   9.011  10.405  -5.177   4.539   0.227  H29  AKN  67  
AKN  H31  H31  H  0  1  N  N  N  30.694   7.866  12.186  -2.941   4.922   1.057  H31  AKN  68  
AKN  H32  H32  H  0  1  N  N  N  30.785   5.551  11.856  -1.705   6.150  -0.576  H32  AKN  69  
AKN  H33  H33  H  0  1  N  N  N  29.550   6.908   9.492  -0.812   3.331  -0.446  H33  AKN  70  
AKN  H34  H34  H  0  1  N  N  N  27.857   5.884  10.572  -0.123   5.606   0.358  H34  AKN  71  
AKN  H35  H35  H  0  1  N  N  N  29.014   5.828  11.945  -0.611   5.137   2.005  H35  AKN  72  
AKN  H36  H36  H  0  1  N  N  N  26.931   6.643  12.559   1.709   4.725   1.613  H36  AKN  73  
AKN  H37  H37  H  0  1  N  N  N  27.291   4.518   6.348   3.874   2.742  -0.846  H37  AKN  74  
AKN  H38  H38  H  0  1  N  N  N  27.228   3.109   3.320   6.714   1.279  -2.104  H38  AKN  75  
AKN  H39  H39  H  0  1  N  N  N  34.818  15.788   9.408  -5.263  -4.681   2.886  H39  AKN  76  
AKN  H40  H40  H  0  1  N  N  N  34.063  14.488  10.045  -6.766  -5.311   2.553  H40  AKN  77  
AKN  H42  H42  H  0  1  N  N  N  31.874  14.261   5.999  -5.349  -1.925  -0.343  H42  AKN  78  
AKN  H43  H43  H  0  1  N  N  N  32.368  13.239   8.848  -4.129  -4.677   0.155  H43  AKN  79  
AKN  H44  H44  H  0  1  N  N  N  33.550  13.027   7.512  -4.029  -3.308   1.287  H44  AKN  80  
AKN  H45  H45  H  0  1  N  N  N  33.743  15.479   7.292  -6.605  -4.587   0.264  H45  AKN  81  
AKN  H46  H46  H  0  1  N  N  N  32.558  15.692   8.626  -6.505  -3.217   1.396  H46  AKN  82  
AKN  H47  H47  H  0  1  N  N  N  30.745  15.048   7.753  -5.001  -4.223  -2.084  H47  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  O6   C5   SING  N  N   1  
AKN  C9   C7   SING  N  N   2  
AKN  C9   N10  SING  N  N   3  
AKN  C5   C7   SING  N  N   4  
AKN  C5   C4   SING  N  N   5  
AKN  O33  C4   SING  N  N   6  
AKN  C7   O8   SING  N  N   7  
AKN  N15  C14  SING  N  N   8  
AKN  C4   C3   SING  N  N   9  
AKN  C14  C13  SING  N  N  10  
AKN  C14  C16  SING  N  N  11  
AKN  O8   C1   SING  N  N  12  
AKN  O2   C1   SING  N  N  13  
AKN  O2   C16  SING  N  N  14  
AKN  C3   C1   SING  N  N  15  
AKN  C3   O32  SING  N  N  16  
AKN  C13  C11  SING  N  N  17  
AKN  C16  C17  SING  N  N  18  
AKN  O36  C35  DOUB  N  N  19  
AKN  C11  N12  SING  N  N  20  
AKN  C11  C19  SING  N  N  21  
AKN  C35  N12  SING  N  N  22  
AKN  C35  C37  SING  N  N  23  
AKN  C17  C19  SING  N  N  24  
AKN  C17  O18  SING  N  N  25  
AKN  C37  O40  SING  N  N  26  
AKN  C37  C38  SING  N  N  27  
AKN  C19  O20  SING  N  N  28  
AKN  C38  C39  SING  N  N  29  
AKN  C39  N37  SING  N  N  30  
AKN  O20  C21  SING  N  N  31  
AKN  O23  C22  SING  N  N  32  
AKN  C21  C22  SING  N  N  33  
AKN  C21  O29  SING  N  N  34  
AKN  C22  C24  SING  N  N  35  
AKN  O29  C28  SING  N  N  36  
AKN  C24  N25  SING  N  N  37  
AKN  C24  C26  SING  N  N  38  
AKN  C28  C26  SING  N  N  39  
AKN  C28  C30  SING  N  N  40  
AKN  C26  O27  SING  N  N  41  
AKN  C30  O31  SING  N  N  42  
AKN  C1   H1   SING  N  N  43  
AKN  C3   H2   SING  N  N  44  
AKN  C4   H3   SING  N  N  45  
AKN  C5   H4   SING  N  N  46  
AKN  C7   H5   SING  N  N  47  
AKN  C9   H6   SING  N  N  48  
AKN  C9   H7   SING  N  N  49  
AKN  O6   H8   SING  N  N  50  
AKN  N10  H9   SING  N  N  51  
AKN  N10  H10  SING  N  N  52  
AKN  C11  H12  SING  N  N  53  
AKN  N12  H13  SING  N  N  54  
AKN  C13  H14  SING  N  N  55  
AKN  C13  H15  SING  N  N  56  
AKN  C14  H16  SING  N  N  57  
AKN  N15  H17  SING  N  N  58  
AKN  N15  H18  SING  N  N  59  
AKN  C16  H20  SING  N  N  60  
AKN  C17  H21  SING  N  N  61  
AKN  O18  H22  SING  N  N  62  
AKN  C19  H23  SING  N  N  63  
AKN  C21  H24  SING  N  N  64  
AKN  C22  H25  SING  N  N  65  
AKN  O23  H26  SING  N  N  66  
AKN  C24  H27  SING  N  N  67  
AKN  N25  H28  SING  N  N  68  
AKN  N25  H29  SING  N  N  69  
AKN  C26  H31  SING  N  N  70  
AKN  O27  H32  SING  N  N  71  
AKN  C28  H33  SING  N  N  72  
AKN  C30  H34  SING  N  N  73  
AKN  C30  H35  SING  N  N  74  
AKN  O31  H36  SING  N  N  75  
AKN  O32  H37  SING  N  N  76  
AKN  O33  H38  SING  N  N  77  
AKN  N37  H39  SING  N  N  78  
AKN  N37  H40  SING  N  N  79  
AKN  C37  H42  SING  N  N  80  
AKN  C38  H43  SING  N  N  81  
AKN  C38  H44  SING  N  N  82  
AKN  C39  H45  SING  N  N  83  
AKN  C39  H46  SING  N  N  84  
AKN  O40  H47  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               12.01  "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                 1.03   "InChI=1S/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"  
AKN  InChIKey          InChI                 1.03   LKCWBDHBTVXHDL-RMDFUYIESA-N  
AKN  SMILES_CANONICAL  CACTVS                3.385  "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                3.385  "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"  1.9.2  "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"  1.9.2  "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               12.01  "(2S)-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"  1.9.2  "(2S)-N-[(1R,2S,3S,4R,5S)-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]oxy-5-azanyl-2-[(2S,3R,4S,5S,6R)-4-azanyl-6-(hydroxymethyl)-3,5-bis(oxidanyl)oxan-2-yl]oxy-3-oxidanyl-cyclohexyl]-4-azanyl-2-oxidanyl-butanamide"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
AKN  "Create component"    2006-02-28  RCSB  
AKN  "Modify descriptor"   2011-06-04  RCSB  
AKN  "Other modification"  2014-03-13  RCSB  
AKN  "Modify descriptor"   2014-09-05  RCSB  
AKN  "Modify synonyms"     2020-06-05  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     AKN
_pdbx_chem_comp_synonyms.name        AMIKACIN
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
