data_SIS
#

_chem_comp.id                                   SIS
_chem_comp.name                                 "(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy}-2-hydroxycyclohexyl 3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranoside"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C19 H37 N5 O7"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        Sisomicin
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2012-06-12
_chem_comp.pdbx_modified_date                   2021-03-01
_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                       447.526
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    SIS
_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       4F8U
_chem_comp.pdbx_subcomponent_list               ?
_chem_comp.pdbx_processing_site                 PDBJ
#   #
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
SIS  C11  C11  C  0  1  N  N  S  -30.990  -0.347   -5.662  -3.067   0.772   0.444  C11  SIS   1  
SIS  C12  C12  C  0  1  N  N  R  -35.486   2.257   -7.134   0.717  -2.942   0.515  C12  SIS   2  
SIS  C13  C13  C  0  1  N  N  R  -34.928   1.674  -10.490   2.530  -0.250  -1.177  C13  SIS   3  
SIS  C21  C21  C  0  1  N  N  R  -31.021  -1.789   -5.032  -3.724   1.864   1.299  C21  SIS   4  
SIS  C22  C22  C  0  1  N  N  N  -34.788   2.947   -5.880  -0.733  -3.426   0.470  C22  SIS   5  
SIS  C23  C23  C  0  1  N  N  R  -36.252   1.346  -11.217   4.045  -0.031  -1.172  C23  SIS   6  
SIS  C31  C31  C  0  1  N  N  N  -30.981  -1.698   -3.454  -4.428   2.848   0.358  C31  SIS   7  
SIS  C32  C32  C  0  1  N  N  S  -33.952   1.863   -5.087  -1.624  -2.441   1.229  C32  SIS   8  
SIS  C33  C33  C  0  1  N  N  R  -36.368  -0.236  -11.328   4.448   0.669   0.130  C33  SIS   9  
SIS  C41  C41  C  0  1  N  N  N  -29.990  -0.590   -2.958  -5.232   2.082  -0.657  C41  SIS  10  
SIS  C42  C42  C  0  1  N  N  R  -32.877   1.231   -6.027  -1.526  -1.060   0.578  C42  SIS  11  
SIS  C43  C43  C  0  1  N  N  R  -35.122  -0.797  -12.179   3.669   1.983   0.252  C43  SIS  12  
SIS  C51  C51  C  0  1  N  N  N  -29.492   0.332   -3.808  -5.031   0.814  -0.900  C51  SIS  13  
SIS  C52  C52  C  0  1  N  N  S  -33.583   0.583   -7.299  -0.076  -0.576   0.623  C52  SIS  14  
SIS  C53  C53  C  0  1  N  N  N  -33.784  -0.396  -11.457   2.169   1.686   0.192  C53  SIS  15  
SIS  C61  C61  C  0  1  N  N  N  -28.512   1.437   -3.355  -5.885   0.142  -1.944  C61  SIS  16  
SIS  C62  C62  C  0  1  N  N  S  -34.401   1.684   -8.074   0.815  -1.561  -0.136  C62  SIS  17  
SIS  C83  C83  C  0  1  N  N  N  -35.075  -2.337  -12.381   4.005   2.654   1.585  C83  SIS  18  
SIS  C93  C93  C  0  1  N  N  N  -38.786  -0.885  -11.119   6.658  -0.213   0.573  C93  SIS  19  
SIS  N12  N12  N  0  1  N  N  N  -36.243   3.227   -7.866   1.572  -3.889  -0.213  N12  SIS  20  
SIS  N21  N21  N  0  1  N  N  N  -32.237  -2.467   -5.497  -4.706   1.258   2.208  N21  SIS  21  
SIS  N32  N32  N  0  1  N  N  N  -33.271   2.478   -3.920  -3.017  -2.905   1.185  N32  SIS  22  
SIS  N33  N33  N  0  1  N  N  N  -37.642  -0.600  -12.009   5.889   0.950   0.111  N33  SIS  23  
SIS  N61  N61  N  0  1  N  N  N  -29.071   2.732   -3.698  -5.040  -0.279  -3.070  N61  SIS  24  
SIS  O11  O11  O  0  1  N  N  N  -32.197   0.263   -5.266  -2.358  -0.139   1.286  O11  SIS  25  
SIS  O23  O23  O  0  1  N  N  N  -37.331   1.884  -10.485   4.711  -1.292  -1.262  O23  SIS  26  
SIS  O43  O43  O  0  1  N  N  N  -35.124  -0.260  -13.491   4.027   2.852  -0.825  O43  SIS  27  
SIS  O51  O51  O  0  1  N  N  N  -29.820   0.373   -5.203  -4.097   0.075  -0.262  O51  SIS  28  
SIS  O52  O52  O  0  1  N  N  N  -32.577   0.054   -8.168   0.015   0.714   0.015  O52  SIS  29  
SIS  O53  O53  O  0  1  N  N  N  -33.759   1.107  -11.220   1.867   1.007  -1.029  O53  SIS  30  
SIS  O62  O62  O  0  1  N  N  N  -35.024   1.096   -9.177   2.170  -1.109  -0.093  O62  SIS  31  
SIS  H1   H1   H  0  1  N  N  N  -30.956  -0.452   -6.756  -2.377   1.227  -0.268  H1   SIS  32  
SIS  H2   H2   H  0  1  N  N  N  -36.130   1.440   -6.777   1.047  -2.879   1.553  H2   SIS  33  
SIS  H3   H3   H  0  1  N  N  N  -34.823   2.767  -10.419   2.233  -0.710  -2.120  H3   SIS  34  
SIS  H4   H4   H  0  1  N  N  N  -30.131  -2.339   -5.372  -2.962   2.388   1.876  H4   SIS  35  
SIS  H5   H5   H  0  1  N  N  N  -34.118   3.747   -6.227  -1.063  -3.490  -0.567  H5   SIS  36  
SIS  H6   H6   H  0  1  N  N  N  -35.557   3.374   -5.220  -0.803  -4.410   0.934  H6   SIS  37  
SIS  H7   H7   H  0  1  N  N  N  -36.217   1.766  -12.233   4.326   0.591  -2.023  H7   SIS  38  
SIS  H8   H8   H  0  1  N  N  N  -31.990  -1.463   -3.086  -5.091   3.492   0.936  H8   SIS  39  
SIS  H9   H9   H  0  1  N  N  N  -30.660  -2.669   -3.050  -3.683   3.458  -0.153  H9   SIS  40  
SIS  H10  H10  H  0  1  N  N  N  -34.636   1.072   -4.747  -1.294  -2.377   2.266  H10  SIS  41  
SIS  H11  H11  H  0  1  N  N  N  -36.334  -0.671  -10.318   4.212   0.026   0.977  H11  SIS  42  
SIS  H12  H12  H  0  1  N  N  N  -29.701  -0.564   -1.918  -6.004   2.601  -1.206  H12  SIS  43  
SIS  H13  H13  H  0  1  N  N  N  -32.192   2.021   -6.370  -1.856  -1.123  -0.460  H13  SIS  44  
SIS  H14  H14  H  0  1  N  N  N  -34.271  -0.206   -6.962   0.254  -0.512   1.660  H14  SIS  45  
SIS  H15  H15  H  0  1  N  N  N  -33.718  -0.919  -10.492   1.889   1.056   1.036  H15  SIS  46  
SIS  H16  H16  H  0  1  N  N  N  -32.929  -0.681  -12.087   1.611   2.621   0.235  H16  SIS  47  
SIS  H17  H17  H  0  1  N  N  N  -28.364   1.375   -2.267  -6.372  -0.730  -1.509  H17  SIS  48  
SIS  H18  H18  H  0  1  N  N  N  -27.546   1.305   -3.865  -6.642   0.841  -2.300  H18  SIS  49  
SIS  H19  H19  H  0  1  N  N  N  -33.718   2.491   -8.378   0.485  -1.625  -1.173  H19  SIS  50  
SIS  H20  H20  H  0  1  N  N  N  -35.071  -2.836  -11.401   3.734   1.989   2.405  H20  SIS  51  
SIS  H21  H21  H  0  1  N  N  N  -35.958  -2.659  -12.952   5.073   2.865   1.627  H21  SIS  52  
SIS  H22  H22  H  0  1  N  N  N  -34.163  -2.607  -12.934   3.446   3.586   1.674  H22  SIS  53  
SIS  H23  H23  H  0  1  N  N  N  -39.668  -1.141  -11.725   6.364  -0.461   1.593  H23  SIS  54  
SIS  H24  H24  H  0  1  N  N  N  -38.536  -1.730  -10.460   6.459  -1.063  -0.079  H24  SIS  55  
SIS  H25  H25  H  0  1  N  N  N  -39.006   0.003  -10.509   7.722   0.023   0.550  H25  SIS  56  
SIS  H26  H26  H  0  1  N  N  N  -36.952   3.612   -7.275   1.525  -4.809   0.198  H26  SIS  57  
SIS  H27  H27  H  0  1  N  N  N  -35.636   3.958   -8.177   1.328  -3.917  -1.192  H27  SIS  58  
SIS  H29  H29  H  0  1  N  N  N  -32.276  -3.387   -5.107  -5.151   1.960   2.780  H29  SIS  59  
SIS  H30  H30  H  0  1  N  N  N  -33.040  -1.947   -5.206  -5.391   0.723   1.695  H30  SIS  60  
SIS  H32  H32  H  0  1  N  N  N  -33.953   2.885   -3.312  -3.108  -3.816   1.610  H32  SIS  61  
SIS  H33  H33  H  0  1  N  N  N  -32.760   1.776   -3.424  -3.634  -2.239   1.624  H33  SIS  62  
SIS  H35  H35  H  0  1  N  N  N  -37.899   0.160  -12.606   6.189   1.240  -0.808  H35  SIS  63  
SIS  H37  H37  H  0  1  N  N  N  -28.443   3.454   -3.408  -4.291  -0.877  -2.756  H37  SIS  64  
SIS  H38  H38  H  0  1  N  N  N  -29.206   2.785   -4.687  -5.589  -0.733  -3.784  H38  SIS  65  
SIS  H40  H40  H  0  1  N  N  N  -37.239   2.828  -10.433   4.498  -1.793  -2.061  H40  SIS  66  
SIS  H41  H41  H  0  1  N  N  N  -35.152   0.688  -13.445   3.567   3.703  -0.813  H41  SIS  67  
SIS  H42  H42  H  0  1  N  N  N  -32.079  -0.611   -7.708  -0.467   1.407   0.487  H42  SIS  68  
#   #
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
SIS  O43  C43  SING  N  N   1  
SIS  C83  C43  SING  N  N   2  
SIS  C43  C53  SING  N  N   3  
SIS  C43  C33  SING  N  N   4  
SIS  N33  C33  SING  N  N   5  
SIS  N33  C93  SING  N  N   6  
SIS  C53  O53  SING  N  N   7  
SIS  C33  C23  SING  N  N   8  
SIS  O53  C13  SING  N  N   9  
SIS  C23  C13  SING  N  N  10  
SIS  C23  O23  SING  N  N  11  
SIS  C13  O62  SING  N  N  12  
SIS  O62  C62  SING  N  N  13  
SIS  O52  C52  SING  N  N  14  
SIS  C62  C52  SING  N  N  15  
SIS  C62  C12  SING  N  N  16  
SIS  N12  C12  SING  N  N  17  
SIS  C52  C42  SING  N  N  18  
SIS  C12  C22  SING  N  N  19  
SIS  C42  O11  SING  N  N  20  
SIS  C42  C32  SING  N  N  21  
SIS  C22  C32  SING  N  N  22  
SIS  C11  O11  SING  N  N  23  
SIS  C11  O51  SING  N  N  24  
SIS  C11  C21  SING  N  N  25  
SIS  N21  C21  SING  N  N  26  
SIS  O51  C51  SING  N  N  27  
SIS  C32  N32  SING  N  N  28  
SIS  C21  C31  SING  N  N  29  
SIS  C51  C61  SING  N  N  30  
SIS  C51  C41  DOUB  N  N  31  
SIS  N61  C61  SING  N  N  32  
SIS  C31  C41  SING  N  N  33  
SIS  C11  H1   SING  N  N  34  
SIS  C12  H2   SING  N  N  35  
SIS  C13  H3   SING  N  N  36  
SIS  C21  H4   SING  N  N  37  
SIS  C22  H5   SING  N  N  38  
SIS  C22  H6   SING  N  N  39  
SIS  C23  H7   SING  N  N  40  
SIS  C31  H8   SING  N  N  41  
SIS  C31  H9   SING  N  N  42  
SIS  C32  H10  SING  N  N  43  
SIS  C33  H11  SING  N  N  44  
SIS  C41  H12  SING  N  N  45  
SIS  C42  H13  SING  N  N  46  
SIS  C52  H14  SING  N  N  47  
SIS  C53  H15  SING  N  N  48  
SIS  C53  H16  SING  N  N  49  
SIS  C61  H17  SING  N  N  50  
SIS  C61  H18  SING  N  N  51  
SIS  C62  H19  SING  N  N  52  
SIS  C83  H20  SING  N  N  53  
SIS  C83  H21  SING  N  N  54  
SIS  C83  H22  SING  N  N  55  
SIS  C93  H23  SING  N  N  56  
SIS  C93  H24  SING  N  N  57  
SIS  C93  H25  SING  N  N  58  
SIS  N12  H26  SING  N  N  59  
SIS  N12  H27  SING  N  N  60  
SIS  N21  H29  SING  N  N  61  
SIS  N21  H30  SING  N  N  62  
SIS  N32  H32  SING  N  N  63  
SIS  N32  H33  SING  N  N  64  
SIS  N33  H35  SING  N  N  65  
SIS  N61  H37  SING  N  N  66  
SIS  N61  H38  SING  N  N  67  
SIS  O23  H40  SING  N  N  68  
SIS  O43  H41  SING  N  N  69  
SIS  O52  H42  SING  N  N  70  
#   #
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
SIS  SMILES            ACDLabs               12.01  "O(C2C(O)C(OC1OC(=CCC1N)CN)C(N)CC2N)C3OCC(O)(C(NC)C3O)C"  
SIS  InChI             InChI                 1.03   "InChI=1S/C19H37N5O7/c1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17/h3,9-18,24-27H,4-7,20-23H2,1-2H3/t9-,10+,11-,12+,13-,14-,15+,16-,17-,18-,19+/m1/s1"  
SIS  InChIKey          InChI                 1.03   URWAJWIAIPFPJE-YFMIWBNJSA-N  
SIS  SMILES_CANONICAL  CACTVS                3.370  "CN[C@@H]1[C@@H](O)[C@H](OC[C@]1(C)O)O[C@H]2[C@H](N)C[C@H](N)[C@@H](O[C@H]3OC(=CC[C@H]3N)CN)[C@@H]2O"  
SIS  SMILES            CACTVS                3.370  "CN[CH]1[CH](O)[CH](OC[C]1(C)O)O[CH]2[CH](N)C[CH](N)[CH](O[CH]3OC(=CC[CH]3N)CN)[CH]2O"  
SIS  SMILES_CANONICAL  "OpenEye OEToolkits"  1.7.6  "C[C@@]1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]2[C@@H](C[C@@H]([C@H]([C@@H]2O)O[C@@H]3[C@@H](CC=C(O3)CN)N)N)N)O"  
SIS  SMILES            "OpenEye OEToolkits"  1.7.6  "CC1(COC(C(C1NC)O)OC2C(CC(C(C2O)OC3C(CC=C(O3)CN)N)N)N)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
SIS  "SYSTEMATIC NAME"  ACDLabs               12.01  "(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy}-2-hydroxycyclohexyl 3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranoside"  
SIS  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.7.6  "(2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-3-[[(2S,3R)-6-(aminomethyl)-3-azanyl-3,4-dihydro-2H-pyran-2-yl]oxy]-4,6-bis(azanyl)-2-oxidanyl-cyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
SIS  "Create component"  2012-06-12  PDBJ  
SIS  "Modify synonyms"   2021-03-01  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     SIS
_pdbx_chem_comp_synonyms.name        Sisomicin
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
