NP-MRD: Showing NP-Card for Sisomicin (NP0021480)

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Record Information

Version

1.0

Created at

2021-01-06 06:45:47 UTC

Updated at

2021-07-15 17:36:28 UTC

NP-MRD ID

NP0021480

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sisomicin

Provided By

NPAtlas

Description

Sisomicin is also known as antibiotic 6640 or rickamicin. Sisomicin is found in Micromonospora and Micromonospora inyonensis. It was first documented in 1974 (PMID: 4833504). Based on a literature review very few articles have been published on Sisomicin.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105163D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242105163D          

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 31 68  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021480

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])[C@@]([H])(O[C@@]2([H])OC([H])([H])[C@@](O[H])(C([H])([H])[H])[C@]([H])(N([H])C([H])([H])[H])[C@@]2([H])O[H])[C@]([H])(N([H])[H])C([H])([H])[C@]([H])(N([H])[H])[C@@]1([H])O[C@@]1([H])OC(=C([H])C([H])([H])[C@@]1([H])N([H])[H])C([H])([H])N([H])[H]

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
URWAJWIAIPFPJE-YFMIWBNJSA-N

> <FORMULA>
C19H37N5O7

> <MOLECULAR_WEIGHT>
447.5264

> <EXACT_MASS>
447.269298563

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
47.071546113718036

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4R,5R)-2-{[(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]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol

> <ALOGPS_LOGP>
-2.03

> <JCHEM_LOGP>
-4.318567550666666

> <ALOGPS_LOGS>
-1.46

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
5

> <JCHEM_PKA>
13.159155802521841

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.548251763563151

> <JCHEM_PKA_STRONGEST_BASIC>
9.738114223543352

> <JCHEM_POLAR_SURFACE_AREA>
213.72

> <JCHEM_REFRACTIVITY>
110.3207

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.56e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
SISO

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 68 70  0  0  0  0  0  0  0  0999 V2000
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 11 43  1  1
 13 44  1  1
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  1
 21 53  1  0
 21 54  1  0
 22 55  1  6
 23 56  1  0
 23 57  1  0
 24 58  1  0
 24 59  1  0
 25 60  1  1
 26 61  1  0
 26 62  1  0
 28 63  1  0
 28 64  1  0
 30 65  1  0
 30 66  1  0
 30 67  1  0
 31 68  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       6.349   1.242   0.813  0.00  0.00           C+0
HETATM    2  N   UNK     0       6.116  -0.104   0.350  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.120  -0.084  -0.711  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.846   0.440  -0.121  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.376   1.569  -0.811  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.720  -0.583  -0.182  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.552   0.098   0.088  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.837  -0.429   1.151  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.529  -0.802   0.630  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.958  -1.900   1.403  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.517   0.305   0.623  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.456   0.190  -0.405  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.732   0.040   0.095  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.551   1.144  -0.267  0.00  0.00           O+0
HETATM   15  C   UNK     0      -5.926   0.997  -0.393  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.898   1.999   0.111  0.00  0.00           C+0
HETATM   17  N   UNK     0      -8.244   1.546  -0.175  0.00  0.00           N+0
HETATM   18  C   UNK     0      -6.336  -0.105  -0.998  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.303  -1.047  -1.467  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.343  -1.283  -0.333  0.00  0.00           C+0
HETATM   21  N   UNK     0      -3.326  -2.211  -0.788  0.00  0.00           N+0
HETATM   22  C   UNK     0      -0.939   1.693   0.543  0.00  0.00           C+0
HETATM   23  N   UNK     0      -2.017   2.616   0.858  0.00  0.00           N+0
HETATM   24  C   UNK     0       0.174   1.919   1.510  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.643   0.656   2.185  0.00  0.00           C+0
HETATM   26  N   UNK     0      -0.320   0.234   3.186  0.00  0.00           N+0
HETATM   27  O   UNK     0       2.650  -0.987  -1.518  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.689  -1.841  -1.808  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.017  -1.462  -1.275  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.056  -1.607  -2.368  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.369  -2.409  -0.286  0.00  0.00           O+0
HETATM   32  H   UNK     0       6.006   1.962   0.042  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.805   1.497   1.738  0.00  0.00           H+0
HETATM   34  H   UNK     0       7.444   1.359   0.943  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.700  -0.653   1.157  0.00  0.00           H+0
HETATM   36  H   UNK     0       5.468   0.645  -1.471  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.937   0.746   0.940  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.751   1.346  -1.530  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.901  -1.443   0.497  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.332  -1.315   1.598  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.376  -1.168  -0.424  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.221  -2.543   1.434  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.078   0.249   1.589  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.695   0.046   1.200  0.00  0.00           H+0
HETATM   45  H   UNK     0      -6.696   3.003  -0.301  0.00  0.00           H+0
HETATM   46  H   UNK     0      -6.831   2.098   1.227  0.00  0.00           H+0
HETATM   47  H   UNK     0      -8.435   1.450  -1.191  0.00  0.00           H+0
HETATM   48  H   UNK     0      -8.419   0.650   0.299  0.00  0.00           H+0
HETATM   49  H   UNK     0      -7.372  -0.329  -1.153  0.00  0.00           H+0
HETATM   50  H   UNK     0      -5.773  -2.034  -1.732  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.812  -0.691  -2.397  0.00  0.00           H+0
HETATM   52  H   UNK     0      -4.893  -1.727   0.498  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.748  -2.927  -1.430  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.540  -1.752  -1.289  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.643   1.953  -0.518  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.564   3.474   1.266  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.495   2.945  -0.010  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.148   2.613   2.312  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.023   2.419   0.993  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.588   0.883   2.729  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.451   1.024   3.847  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.009  -0.587   3.727  0.00  0.00           H+0
HETATM   63  H   UNK     0       3.368  -2.865  -1.454  0.00  0.00           H+0
HETATM   64  H   UNK     0       3.711  -1.950  -2.932  0.00  0.00           H+0
HETATM   65  H   UNK     0       5.992  -2.598  -2.880  0.00  0.00           H+0
HETATM   66  H   UNK     0       7.093  -1.494  -1.961  0.00  0.00           H+0
HETATM   67  H   UNK     0       5.937  -0.836  -3.159  0.00  0.00           H+0
HETATM   68  H   UNK     0       5.000  -3.283  -0.567  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    1    3   35                                                  
CONECT    3    2    4   29   36                                             
CONECT    4    3    5    6   37                                             
CONECT    5    4   38                                                       
CONECT    6    4    7   27   39                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   25   40                                             
CONECT    9    8   10   11   41                                             
CONECT   10    9   42                                                       
CONECT   11    9   12   22   43                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   20   44                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17   45   46                                             
CONECT   17   16   47   48                                                  
CONECT   18   15   19   49                                                  
CONECT   19   18   20   50   51                                             
CONECT   20   19   21   13   52                                             
CONECT   21   20   53   54                                                  
CONECT   22   11   23   24   55                                             
CONECT   23   22   56   57                                                  
CONECT   24   22   25   58   59                                             
CONECT   25   24   26    8   60                                             
CONECT   26   25   61   62                                                  
CONECT   27    6   28                                                       
CONECT   28   27   29   63   64                                             
CONECT   29   28   30   31    3                                             
CONECT   30   29   65   66   67                                             
CONECT   31   29   68                                                       
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    2                                                            
CONECT   36    3                                                            
CONECT   37    4                                                            
CONECT   38    5                                                            
CONECT   39    6                                                            
CONECT   40    8                                                            
CONECT   41    9                                                            
CONECT   42   10                                                            
CONECT   43   11                                                            
CONECT   44   13                                                            
CONECT   45   16                                                            
CONECT   46   16                                                            
CONECT   47   17                                                            
CONECT   48   17                                                            
CONECT   49   18                                                            
CONECT   50   19                                                            
CONECT   51   19                                                            
CONECT   52   20                                                            
CONECT   53   21                                                            
CONECT   54   21                                                            
CONECT   55   22                                                            
CONECT   56   23                                                            
CONECT   57   23                                                            
CONECT   58   24                                                            
CONECT   59   24                                                            
CONECT   60   25                                                            
CONECT   61   26                                                            
CONECT   62   26                                                            
CONECT   63   28                                                            
CONECT   64   28                                                            
CONECT   65   30                                                            
CONECT   66   30                                                            
CONECT   67   30                                                            
CONECT   68   31                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  140    0
END

RDKit          3D

68 70  0  0  0  0  0  0  0  0999 V2000
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    6.1160   -0.1040    0.3496 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1198   -0.0835   -0.7108 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8461    0.4399   -0.1205 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3760    1.5687   -0.8109 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7203   -0.5829   -0.1824 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5523    0.0981    0.0880 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8372   -0.4291    1.1508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5288   -0.8023    0.6302 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9577   -1.8998    1.4026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5167    0.3045    0.6234 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4558    0.1900   -0.4045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7315    0.0399    0.0947 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5508    1.1438   -0.2673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9255    0.9970   -0.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8977    1.9988    0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2444    1.5459   -0.1753 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3359   -0.1052   -0.9976 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3425   -1.2830   -0.3332 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.0167    2.6157    0.8577 N   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0565   -1.6072   -2.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3691   -2.4088   -0.2855 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3324   -1.3153    1.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3761   -1.1680   -0.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6949    0.0463    1.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6961    3.0029   -0.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8310    2.0979    1.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.4186    0.6502    0.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3725   -0.3293   -1.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7726   -2.0342   -1.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8124   -0.6906   -2.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8933   -1.7273    0.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7480   -2.9266   -1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5396   -1.7520   -1.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6434    1.9527   -0.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0086   -0.5870    3.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3684   -2.8653   -1.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7109   -1.9496   -2.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9916   -2.5979   -2.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0931   -1.4944   -1.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.8356   -3.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9998   -3.2828   -0.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
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 15 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 11 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
  6 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  1
 29  3  1  0
 25  8  1  0
 20 13  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  3 36  1  6
  4 37  1  1
  5 38  1  0
  6 39  1  1
  8 40  1  1
  9 41  1  6
 10 42  1  0
 11 43  1  1
 13 44  1  1
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  1
 21 53  1  0
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 22 55  1  6
 23 56  1  0
 23 57  1  0
 24 58  1  0
 24 59  1  0
 25 60  1  1
 26 61  1  0
 26 62  1  0
 28 63  1  0
 28 64  1  0
 30 65  1  0
 30 66  1  0
 30 67  1  0
 31 68  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Antibiotic 6640	ChEBI
Dehydrogentamicin cla	ChEBI
O-2,6-Diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-4)-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6))-2-deoxy-D-streptamine	ChEBI
Rickamicin	ChEBI
Sissomicin	ChEBI
O-2,6-Diamino-2,3,4,6-tetradeoxy-a-D-glycero-hex-4-enopyranosyl-(1-4)-O-(3-deoxy-4-C-methyl-3-(methylamino)-b-L-arabinopyranosyl-(1-6))-2-deoxy-D-streptamine	Generator
O-2,6-Diamino-2,3,4,6-tetradeoxy-α-D-glycero-hex-4-enopyranosyl-(1-4)-O-(3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl-(1-6))-2-deoxy-D-streptamine	Generator
4,5 Dehydrogentamicin	MeSH
Sisomicin sulfate (2:5) salt	MeSH
Sisomycin	MeSH
Extramycin	MeSH
Pathomycin	MeSH
4,5-Dehydrogentamicin	MeSH
Sizomycin	MeSH
Siseptin	MeSH
Sisomicin sulfate	MeSH
Sisomicin	ChEBI
6640, Antibiotic	MeSH
SISO	KEGG

Chemical Formula

C₁₉H₃₇N₅O₇

Average Mass

447.5264 Da

Monoisotopic Mass

447.26930 Da

IUPAC Name

(2R,3R,4R,5R)-2-{[(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]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol

Traditional Name

SISO

CAS Registry Number

Not Available

SMILES

CN[C@@H]1[C@@H](O)[C@@H](O[C@H]2[C@H](N)C[C@H](N)[C@@H](O[C@H]3OC(CN)=CC[C@H]3N)[C@@H]2O)OC[C@]1(C)O

InChI Identifier

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

InChI Key

URWAJWIAIPFPJE-YFMIWBNJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Micromonospora	NPAtlas	4833504
Micromonospora inyonensis	LOTUS Database	35616633

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidically linked to a carbohydrate moiety. There are two major classes of aminoglycosides containing a 2-streptamine core. They are called 4,5- and 4,6-disubstituted 2-deoxystreptamines.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Aminocyclitol glycosides

Alternative Parents

Substituents

Amino cyclitol glycoside
Glycosyl compound
O-glycosyl compound
Aminocyclitol or derivatives
Cyclohexanol
Cyclohexylamine
Cyclitol or derivatives
Monosaccharide
Oxane
Cyclic alcohol
Tertiary alcohol
1,2-aminoalcohol
Secondary alcohol
Acetal
Secondary aliphatic amine
Secondary amine
Organoheterocyclic compound
Oxacycle
Primary aliphatic amine
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Amine
Alcohol
Primary amine
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

monosaccharide derivative (CHEBI:9169 )
aminoglycoside antibiotic (CHEBI:9169 )
amino cyclitol glycoside (CHEBI:9169 )
beta-L-arabinoside (CHEBI:9169 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2	ALOGPS
logP	-4.3	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	12.55	ChemAxon
pKa (Strongest Basic)	9.74	ChemAxon
Physiological Charge	5	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	213.72 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	110.32 m³·mol⁻¹	ChemAxon
Polarizability	47.07 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

NPA009502

HMDB ID

Not Available

DrugBank ID

DB12604

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

33222

KEGG Compound ID

C00494

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sisomicin

METLIN ID

Not Available

PubChem Compound

36119

PDB ID

Not Available

ChEBI ID

9169

Good Scents ID

Not Available

References

General References

Reimann H, Cooper DJ, Mallams AK, Jaret RS, Yehaskel A, Kugelman M, Vernay HF, Schumacher D: The structure of sisomicin, a novel unsaturated aminocyclitol antibiotic from Micromonospora inyoensis. J Org Chem. 1974 May 31;39(11):1451-7. doi: 10.1021/jo00924a001. [PubMed:4833504 ]

Showing NP-Card for Sisomicin (NP0021480)

MOL for NP0021480 (Sisomicin)

3D MOL for NP0021480 (Sisomicin)

3D SDF for NP0021480 (Sisomicin)

3D-SDF for NP0021480 (Sisomicin)

PDB for NP0021480 (Sisomicin)

3D PDB for NP0021480 (Sisomicin)

SMILES for NP0021480 (Sisomicin)

INCHI for NP0021480 (Sisomicin)

Structure for NP0021480 (Sisomicin)

3D Structure for NP0021480 (Sisomicin)