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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1)transporters (2) Show 3 proteins XML

enzymes (1)transporters (2) Show 3 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:40 UTC

HMDB ID

HMDB0014572

Secondary Accession Numbers

HMDB14572

Metabolite Identification

Common Name

Streptozocin

Description

Streptozocin is only found in individuals that have used or taken this drug.It is an antibiotic that is produced by Stretomyces achromogenes. It is used as an antineoplastic agent and to induce diabetes in experimental animals. [PubChem]Although its mechanism of action is not completely clear, streptozocin is known to inhibit DNA synthesis, interfere with biochemical reactions of NAD and NADH, and inhibit some enzymes involved in gluconeogenesis. Its activity appears to occur as a result of formation of methylcarbonium ions, which alkylate or bind with many intracellular molecular structures including nucleic acids. Its cytotoxic action is probably due to cross-linking of strands of DNA, resulting in inhibition of DNA synthesis.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0014572
     RDKit          3D
Streptozocin
 33 33  0  0  0  0  0  0  0  0999 V2000
    4.8392    0.6617    1.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4714    0.9810    0.7340 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1420    2.3125    0.4767 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6600    3.0913    1.3044 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4947   -0.0406    0.6724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8692   -1.2263    0.9185 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1398    0.2591    0.3447 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1365   -0.7660    0.2781 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9767   -0.5872    1.2498 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3988   -0.4211    2.5202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7681    0.5261    1.0135 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9978    0.7495   -0.3258 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3684    1.3804   -0.4699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6845    1.6410   -1.7891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8827   -0.5455   -1.0628 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4296   -0.4766   -2.3492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4328   -0.9553   -1.0986 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4023   -2.2835   -1.5218 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9197   -0.1942    1.7694 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4230    0.3503    0.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3973    1.5278    1.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8937    1.2499    0.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6297   -1.7544    0.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6373   -1.4671    1.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8869   -0.9332    3.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2898    1.4655   -0.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1447    0.7818    0.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3197    2.3597    0.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6362    1.5428   -2.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4729   -1.3290   -0.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0578   -1.1787   -2.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0536   -0.2853   -1.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2826   -2.3303   -2.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  2  5  1  0
  5  6  2  0
  5  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
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  7 22  1  0
  8 23  1  1
  9 24  1  1
 10 25  1  0
 12 26  1  6
 13 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  1
 16 31  1  0
 17 32  1  6
 18 33  1  0
M  END

428
  Mrv0541 02231214402D          

 18 18  0  0  1  0            999 V2000
    4.2365   -1.1880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.0495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -1.6005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.0495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -2.8381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.8745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    3.3496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.8745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    2.1120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    2.5246    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.3630    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5220    0.0495    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8075   -1.1880    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5220   -1.6005    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2365   -0.3630    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5220   -2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  1 15  1  0  0  0  0
 11  2  1  6  0  0  0
 13  3  1  1  0  0  0
 15  4  1  1  0  0  0
  5 16  1  0  0  0  0
  6 17  2  0  0  0  0
  7 10  2  0  0  0  0
 12  8  1  1  0  0  0
  8 17  1  0  0  0  0
  9 10  1  0  0  0  0
  9 17  1  0  0  0  0
  9 18  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 15  1  0  0  0  0
 13 14  1  0  0  0  0
 14 16  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0014572

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(N=O)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C8H15N3O7/c1-11(10-17)8(16)9-4-6(14)5(13)3(2-12)18-7(4)15/h3-7,12-15H,2H2,1H3,(H,9,16)/t3-,4-,5-,6-,7+/m1/s1

> <INCHI_KEY>
ZSJLQEPLLKMAKR-GKHCUFPYSA-N

> <FORMULA>
C8H15N3O7

> <MOLECULAR_WEIGHT>
265.2206

> <EXACT_MASS>
265.090999849

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
23.742135245179043

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methyl-3-nitroso-1-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]urea

> <ALOGPS_LOGP>
-1.71

> <JCHEM_LOGP>
-2.7202855550000002

> <ALOGPS_LOGS>
-0.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.495225806417498

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.42514615892902

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810236083276225

> <JCHEM_POLAR_SURFACE_AREA>
151.92000000000002

> <JCHEM_REFRACTIVITY>
55.955200000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.35e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
streptozocin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014572
     RDKit          3D
Streptozocin
 33 33  0  0  0  0  0  0  0  0999 V2000
    4.8392    0.6617    1.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4714    0.9810    0.7340 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1420    2.3125    0.4767 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6600    3.0913    1.3044 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4947   -0.0406    0.6724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8692   -1.2263    0.9185 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1398    0.2591    0.3447 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1365   -0.7660    0.2781 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9767   -0.5872    1.2498 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3988   -0.4211    2.5202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7681    0.5261    1.0135 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9978    0.7495   -0.3258 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3684    1.3804   -0.4699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6845    1.6410   -1.7891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8827   -0.5455   -1.0628 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4296   -0.4766   -2.3492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4328   -0.9553   -1.0986 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4023   -2.2835   -1.5218 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9197   -0.1942    1.7694 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4230    0.3503    0.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3973    1.5278    1.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8937    1.2499    0.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6297   -1.7544    0.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6373   -1.4671    1.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8869   -0.9332    3.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2898    1.4655   -0.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1447    0.7818    0.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3197    2.3597    0.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6362    1.5428   -2.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4729   -1.3290   -0.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0578   -1.1787   -2.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0536   -0.2853   -1.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2826   -2.3303   -2.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  2  5  1  0
  5  6  2  0
  5  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
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  7 22  1  0
  8 23  1  1
  9 24  1  1
 10 25  1  0
 12 26  1  6
 13 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  1
 16 31  1  0
 17 32  1  6
 18 33  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 428                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       7.908  -2.218   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.907   0.092   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.907  -2.988   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.242   0.092   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.908  -5.298   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       9.242   1.632   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       9.242   6.253   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       6.574   1.632   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       7.908   3.942   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       9.242   4.713   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       5.241  -0.678   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.574   0.092   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.241  -2.218   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.574  -2.988   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.908  -0.678   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.574  -4.528   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.908   2.402   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.574   4.713   0.000  0.00  0.00           C+0
CONECT    1   14   15                                                       
CONECT    2   11                                                            
CONECT    3   13                                                            
CONECT    4   15                                                            
CONECT    5   16                                                            
CONECT    6   17                                                            
CONECT    7   10                                                            
CONECT    8   12   17                                                       
CONECT    9   10   17   18                                                  
CONECT   10    7    9                                                       
CONECT   11    2   12   13                                                  
CONECT   12    8   11   15                                                  
CONECT   13    3   11   14                                                  
CONECT   14    1   13   16                                                  
CONECT   15    1    4   12                                                  
CONECT   16    5   14                                                       
CONECT   17    6    8    9                                                  
CONECT   18    9                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0014572
HETATM    1  C1  UNL     1       4.839   0.662   1.067  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.471   0.981   0.734  1.00  0.00           N  
HETATM    3  N2  UNL     1       3.142   2.313   0.477  1.00  0.00           N  
HETATM    4  O1  UNL     1       2.660   3.091   1.304  1.00  0.00           O  
HETATM    5  C2  UNL     1       2.495  -0.041   0.672  1.00  0.00           C  
HETATM    6  O2  UNL     1       2.869  -1.226   0.919  1.00  0.00           O  
HETATM    7  N3  UNL     1       1.140   0.259   0.345  1.00  0.00           N  
HETATM    8  C3  UNL     1       0.136  -0.766   0.278  1.00  0.00           C  
HETATM    9  C4  UNL     1      -0.977  -0.587   1.250  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.399  -0.421   2.520  1.00  0.00           O  
HETATM   11  O4  UNL     1      -1.768   0.526   1.014  1.00  0.00           O  
HETATM   12  C5  UNL     1      -1.998   0.750  -0.326  1.00  0.00           C  
HETATM   13  C6  UNL     1      -3.368   1.380  -0.470  1.00  0.00           C  
HETATM   14  O5  UNL     1      -3.685   1.641  -1.789  1.00  0.00           O  
HETATM   15  C7  UNL     1      -1.883  -0.545  -1.063  1.00  0.00           C  
HETATM   16  O6  UNL     1      -2.430  -0.477  -2.349  1.00  0.00           O  
HETATM   17  C8  UNL     1      -0.433  -0.955  -1.099  1.00  0.00           C  
HETATM   18  O7  UNL     1      -0.402  -2.283  -1.522  1.00  0.00           O  
HETATM   19  H1  UNL     1       4.920  -0.194   1.769  1.00  0.00           H  
HETATM   20  H2  UNL     1       5.423   0.350   0.153  1.00  0.00           H  
HETATM   21  H3  UNL     1       5.397   1.528   1.480  1.00  0.00           H  
HETATM   22  H4  UNL     1       0.894   1.250   0.153  1.00  0.00           H  
HETATM   23  H5  UNL     1       0.630  -1.754   0.525  1.00  0.00           H  
HETATM   24  H6  UNL     1      -1.637  -1.467   1.307  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.887  -0.933   3.200  1.00  0.00           H  
HETATM   26  H8  UNL     1      -1.290   1.465  -0.793  1.00  0.00           H  
HETATM   27  H9  UNL     1      -4.145   0.782   0.009  1.00  0.00           H  
HETATM   28  H10 UNL     1      -3.320   2.360   0.055  1.00  0.00           H  
HETATM   29  H11 UNL     1      -4.636   1.543  -2.004  1.00  0.00           H  
HETATM   30  H12 UNL     1      -2.473  -1.329  -0.514  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.058  -1.179  -2.938  1.00  0.00           H  
HETATM   32  H14 UNL     1       0.054  -0.285  -1.844  1.00  0.00           H  
HETATM   33  H15 UNL     1      -0.283  -2.330  -2.521  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    5
CONECT    3    4    4
CONECT    5    6    6    7
CONECT    7    8   22
CONECT    8    9   17   23
CONECT    9   10   11   24
CONECT   10   25
CONECT   11   12
CONECT   12   13   15   26
CONECT   13   14   27   28
CONECT   14   29
CONECT   15   16   17   30
CONECT   16   31
CONECT   17   18   32
CONECT   18   33
END

HMDB0014572
     RDKit          3D
Streptozocin
 33 33  0  0  0  0  0  0  0  0999 V2000
    4.8392    0.6617    1.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4714    0.9810    0.7340 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1420    2.3125    0.4767 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6600    3.0913    1.3044 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4947   -0.0406    0.6724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8692   -1.2263    0.9185 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1398    0.2591    0.3447 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1365   -0.7660    0.2781 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9767   -0.5872    1.2498 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3988   -0.4211    2.5202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7681    0.5261    1.0135 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9978    0.7495   -0.3258 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3684    1.3804   -0.4699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6845    1.6410   -1.7891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8827   -0.5455   -1.0628 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4296   -0.4766   -2.3492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4328   -0.9553   -1.0986 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4023   -2.2835   -1.5218 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9197   -0.1942    1.7694 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4230    0.3503    0.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3973    1.5278    1.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8937    1.2499    0.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6297   -1.7544    0.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6373   -1.4671    1.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8869   -0.9332    3.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2898    1.4655   -0.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1447    0.7818    0.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3197    2.3597    0.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6362    1.5428   -2.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4729   -1.3290   -0.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0578   -1.1787   -2.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0536   -0.2853   -1.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2826   -2.3303   -2.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  2  5  1  0
  5  6  2  0
  5  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
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  7 22  1  0
  8 23  1  1
  9 24  1  1
 10 25  1  0
 12 26  1  6
 13 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  1
 16 31  1  0
 17 32  1  6
 18 33  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Deoxy-2-(((methylnitrosoamino)carbonyl)amino)-D-glucopyranose	ChEBI
2-Deoxy-2-(3-methyl-3-nitrosoureido)-D-glucopyranose	ChEBI
Estreptozocina	ChEBI
N-D-Glucosyl-(2)-n'-nitrosomethylharnstoff	ChEBI
N-D-Glucosyl-(2)-n'-nitrosomethylurea	ChEBI
Streptozocine	ChEBI
Streptozocinium	ChEBI
Streptozocinum	ChEBI
Streptozotocin	ChEBI
Zanosar	ChEBI
Streptozotocine	HMDB
Teva brand OF streptozocin	HMDB
Streptozocin teva brand	HMDB
2-Deoxy-2-((methylnitrosoamino)carbonyl)amino-D-glucose	HMDB

Chemical Formula

C₈H₁₅N₃O₇

Average Molecular Weight

265.2206

Monoisotopic Molecular Weight

265.090999849

IUPAC Name

3-methyl-3-nitroso-1-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]urea

Traditional Name

streptozocin

CAS Registry Number

18883-66-4

SMILES

CN(N=O)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C8H15N3O7/c1-11(10-17)8(16)9-4-6(14)5(13)3(2-12)18-7(4)15/h3-7,12-15H,2H2,1H3,(H,9,16)/t3-,4-,5-,6-,7+/m1/s1

InChI Key

ZSJLQEPLLKMAKR-GKHCUFPYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
N-methylnitrosourea
Nitrosourea
Oxane
Nitrosamide
Semicarbazide
Organic n-nitroso compound
Hemiacetal
Carbonic acid derivative
Secondary alcohol
Organic nitroso compound
Oxacycle
Polyol
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-nitrosoureas (CHEBI:9288 )
N-acylglucosamine (CHEBI:9288 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014572)

Process

Not Available

Role

Industrial application

Antineoplastic agent (HMDB: HMDB0014572)

Pharmaceutical industry

Antimicrobial agent

Antibiotic (HMDB: HMDB0014572)

Biological role

Metabolite (HMDB: HMDB0014572)

Modulator

Inhibitor

DNA synthesis inhibitor (HMDB: HMDB0014572)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	115 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	33.5 g/L	Not Available
LogP	-1.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	33.5 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-2.7	ChemAxon
logS	-0.9	ALOGPS
pKa (Strongest Acidic)	11.43	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	151.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	55.96 m³·mol⁻¹	ChemAxon
Polarizability	23.74 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	157.716	31661259
DarkChem	[M-H]-	155.192	31661259
DeepCCS	[M+H]+	160.092	30932474
DeepCCS	[M-H]-	157.697	30932474
DeepCCS	[M-2H]-	191.936	30932474
DeepCCS	[M+Na]+	166.897	30932474
AllCCS	[M+H]+	158.9	32859911
AllCCS	[M+H-H2O]+	155.5	32859911
AllCCS	[M+NH4]+	162.1	32859911
AllCCS	[M+Na]+	163.0	32859911
AllCCS	[M-H]-	156.3	32859911
AllCCS	[M+Na-2H]-	156.5	32859911
AllCCS	[M+HCOO]-	156.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.7 minutes	32390414
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.44 minutes	32390414
Predicted by Siyang on May 30, 2022	10.1938 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.36 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	320.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	500.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	269.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	44.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	174.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	68.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	310.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	256.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	842.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	583.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	46.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	740.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	193.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	330.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	692.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	454.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	363.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Streptozocin	CN(N=O)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O	2670.2	Standard polar	33892256
Streptozocin	CN(N=O)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O	2026.4	Standard non polar	33892256
Streptozocin	CN(N=O)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O	2427.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Streptozocin,1TMS,isomer #1	CN(N=O)C(=O)N[C@H]1[C@@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O	2230.9	Semi standard non polar	33892256
Streptozocin,1TMS,isomer #2	CN(N=O)C(=O)N[C@H]1[C@@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O	2236.2	Semi standard non polar	33892256
Streptozocin,1TMS,isomer #3	CN(N=O)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O	2248.5	Semi standard non polar	33892256
Streptozocin,1TMS,isomer #4	CN(N=O)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C	2248.7	Semi standard non polar	33892256
Streptozocin,1TMS,isomer #5	CN(N=O)C(=O)N([C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C	2163.6	Semi standard non polar	33892256
Streptozocin,2TMS,isomer #1	CN(N=O)C(=O)N[C@H]1[C@@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O	2202.0	Semi standard non polar	33892256
Streptozocin,2TMS,isomer #10	CN(N=O)C(=O)N([C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	2182.8	Semi standard non polar	33892256
Streptozocin,2TMS,isomer #2	CN(N=O)C(=O)N[C@H]1[C@@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O	2230.9	Semi standard non polar	33892256
Streptozocin,2TMS,isomer #3	CN(N=O)C(=O)N[C@H]1[C@@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C	2220.0	Semi standard non polar	33892256
Streptozocin,2TMS,isomer #4	CN(N=O)C(=O)N([C@H]1[C@@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C	2178.0	Semi standard non polar	33892256
Streptozocin,2TMS,isomer #5	CN(N=O)C(=O)N[C@H]1[C@@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	2222.6	Semi standard non polar	33892256
Streptozocin,2TMS,isomer #6	CN(N=O)C(=O)N[C@H]1[C@@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	2206.5	Semi standard non polar	33892256
Streptozocin,2TMS,isomer #7	CN(N=O)C(=O)N([C@H]1[C@@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O)[Si](C)(C)C	2196.5	Semi standard non polar	33892256
Streptozocin,2TMS,isomer #8	CN(N=O)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2210.2	Semi standard non polar	33892256
Streptozocin,2TMS,isomer #9	CN(N=O)C(=O)N([C@H]1[C@@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O)[Si](C)(C)C	2180.9	Semi standard non polar	33892256
Streptozocin,3TMS,isomer #1	CN(N=O)C(=O)N[C@H]1[C@@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	2241.6	Semi standard non polar	33892256
Streptozocin,3TMS,isomer #10	CN(N=O)C(=O)N([C@H]1[C@@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	2235.9	Semi standard non polar	33892256
Streptozocin,3TMS,isomer #2	CN(N=O)C(=O)N[C@H]1[C@@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	2236.7	Semi standard non polar	33892256
Streptozocin,3TMS,isomer #3	CN(N=O)C(=O)N([C@H]1[C@@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O)[Si](C)(C)C	2217.6	Semi standard non polar	33892256
Streptozocin,3TMS,isomer #4	CN(N=O)C(=O)N[C@H]1[C@@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2239.4	Semi standard non polar	33892256
Streptozocin,3TMS,isomer #5	CN(N=O)C(=O)N([C@H]1[C@@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O)[Si](C)(C)C	2215.6	Semi standard non polar	33892256
Streptozocin,3TMS,isomer #6	CN(N=O)C(=O)N([C@H]1[C@@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	2232.4	Semi standard non polar	33892256
Streptozocin,3TMS,isomer #7	CN(N=O)C(=O)N[C@H]1[C@@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2243.1	Semi standard non polar	33892256
Streptozocin,3TMS,isomer #8	CN(N=O)C(=O)N([C@H]1[C@@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O)[Si](C)(C)C	2240.8	Semi standard non polar	33892256
Streptozocin,3TMS,isomer #9	CN(N=O)C(=O)N([C@H]1[C@@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	2245.6	Semi standard non polar	33892256
Streptozocin,4TMS,isomer #1	CN(N=O)C(=O)N[C@H]1[C@@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2263.9	Semi standard non polar	33892256
Streptozocin,4TMS,isomer #2	CN(N=O)C(=O)N([C@H]1[C@@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O)[Si](C)(C)C	2271.6	Semi standard non polar	33892256
Streptozocin,4TMS,isomer #3	CN(N=O)C(=O)N([C@H]1[C@@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	2284.6	Semi standard non polar	33892256
Streptozocin,4TMS,isomer #4	CN(N=O)C(=O)N([C@H]1[C@@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	2290.8	Semi standard non polar	33892256
Streptozocin,4TMS,isomer #5	CN(N=O)C(=O)N([C@H]1[C@@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	2283.1	Semi standard non polar	33892256
Streptozocin,5TMS,isomer #1	CN(N=O)C(=O)N([C@H]1[C@@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	2325.8	Semi standard non polar	33892256
Streptozocin,5TMS,isomer #1	CN(N=O)C(=O)N([C@H]1[C@@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	2282.3	Standard non polar	33892256
Streptozocin,5TMS,isomer #1	CN(N=O)C(=O)N([C@H]1[C@@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	2679.1	Standard polar	33892256
Streptozocin,1TBDMS,isomer #1	CN(N=O)C(=O)N[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O	2482.2	Semi standard non polar	33892256
Streptozocin,1TBDMS,isomer #2	CN(N=O)C(=O)N[C@H]1[C@@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O	2506.4	Semi standard non polar	33892256
Streptozocin,1TBDMS,isomer #3	CN(N=O)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2508.2	Semi standard non polar	33892256
Streptozocin,1TBDMS,isomer #4	CN(N=O)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2496.4	Semi standard non polar	33892256
Streptozocin,1TBDMS,isomer #5	CN(N=O)C(=O)N([C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C(C)(C)C	2446.7	Semi standard non polar	33892256
Streptozocin,2TBDMS,isomer #1	CN(N=O)C(=O)N[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O	2688.9	Semi standard non polar	33892256
Streptozocin,2TBDMS,isomer #10	CN(N=O)C(=O)N([C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2663.9	Semi standard non polar	33892256
Streptozocin,2TBDMS,isomer #2	CN(N=O)C(=O)N[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2714.7	Semi standard non polar	33892256
Streptozocin,2TBDMS,isomer #3	CN(N=O)C(=O)N[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2686.7	Semi standard non polar	33892256
Streptozocin,2TBDMS,isomer #4	CN(N=O)C(=O)N([C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C(C)(C)C	2654.9	Semi standard non polar	33892256
Streptozocin,2TBDMS,isomer #5	CN(N=O)C(=O)N[C@H]1[C@@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2720.0	Semi standard non polar	33892256
Streptozocin,2TBDMS,isomer #6	CN(N=O)C(=O)N[C@H]1[C@@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2717.1	Semi standard non polar	33892256
Streptozocin,2TBDMS,isomer #7	CN(N=O)C(=O)N([C@H]1[C@@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O)[Si](C)(C)C(C)(C)C	2684.3	Semi standard non polar	33892256
Streptozocin,2TBDMS,isomer #8	CN(N=O)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2689.2	Semi standard non polar	33892256
Streptozocin,2TBDMS,isomer #9	CN(N=O)C(=O)N([C@H]1[C@@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)[Si](C)(C)C(C)(C)C	2673.0	Semi standard non polar	33892256
Streptozocin,3TBDMS,isomer #1	CN(N=O)C(=O)N[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2913.3	Semi standard non polar	33892256
Streptozocin,3TBDMS,isomer #10	CN(N=O)C(=O)N([C@H]1[C@@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2865.9	Semi standard non polar	33892256
Streptozocin,3TBDMS,isomer #2	CN(N=O)C(=O)N[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2889.2	Semi standard non polar	33892256
Streptozocin,3TBDMS,isomer #3	CN(N=O)C(=O)N([C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O)[Si](C)(C)C(C)(C)C	2861.0	Semi standard non polar	33892256
Streptozocin,3TBDMS,isomer #4	CN(N=O)C(=O)N[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2878.3	Semi standard non polar	33892256
Streptozocin,3TBDMS,isomer #5	CN(N=O)C(=O)N([C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)[Si](C)(C)C(C)(C)C	2872.2	Semi standard non polar	33892256
Streptozocin,3TBDMS,isomer #6	CN(N=O)C(=O)N([C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2870.7	Semi standard non polar	33892256
Streptozocin,3TBDMS,isomer #7	CN(N=O)C(=O)N[C@H]1[C@@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2907.7	Semi standard non polar	33892256
Streptozocin,3TBDMS,isomer #8	CN(N=O)C(=O)N([C@H]1[C@@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)[Si](C)(C)C(C)(C)C	2903.7	Semi standard non polar	33892256
Streptozocin,3TBDMS,isomer #9	CN(N=O)C(=O)N([C@H]1[C@@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2888.8	Semi standard non polar	33892256
Streptozocin,4TBDMS,isomer #1	CN(N=O)C(=O)N[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3096.1	Semi standard non polar	33892256
Streptozocin,4TBDMS,isomer #2	CN(N=O)C(=O)N([C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)[Si](C)(C)C(C)(C)C	3082.4	Semi standard non polar	33892256
Streptozocin,4TBDMS,isomer #3	CN(N=O)C(=O)N([C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3081.0	Semi standard non polar	33892256
Streptozocin,4TBDMS,isomer #4	CN(N=O)C(=O)N([C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3082.3	Semi standard non polar	33892256
Streptozocin,4TBDMS,isomer #5	CN(N=O)C(=O)N([C@H]1[C@@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3092.9	Semi standard non polar	33892256
Streptozocin,5TBDMS,isomer #1	CN(N=O)C(=O)N([C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3299.9	Semi standard non polar	33892256
Streptozocin,5TBDMS,isomer #1	CN(N=O)C(=O)N([C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3128.5	Standard non polar	33892256
Streptozocin,5TBDMS,isomer #1	CN(N=O)C(=O)N([C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3160.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Streptozocin GC-MS (Non-derivatized) - 70eV, Positive	splash10-02mj-5940000000-8fb8f1885498bea8bc01	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Streptozocin GC-MS (4 TMS) - 70eV, Positive	splash10-000i-5384590000-954f20357dc689aab130	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Streptozocin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Streptozocin 10V, Positive-QTOF	splash10-066s-1390000000-8a52d6755935e91be345	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Streptozocin 20V, Positive-QTOF	splash10-03di-9730000000-8e7df34a65b316df695e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Streptozocin 40V, Positive-QTOF	splash10-03di-9800000000-8768229ecc0345cd843a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Streptozocin 10V, Negative-QTOF	splash10-000i-9340000000-9e14b4f8a6d8f44c6ad6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Streptozocin 20V, Negative-QTOF	splash10-0a4i-9220000000-2ac584cea0c0d26bc11f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Streptozocin 40V, Negative-QTOF	splash10-0a4i-9200000000-dd74fa78262e5a7d35e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Streptozocin 10V, Negative-QTOF	splash10-0006-4940000000-29bcfe413e3e5b2dd305	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Streptozocin 20V, Negative-QTOF	splash10-0536-9100000000-2a734221e4d6f4a10693	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Streptozocin 40V, Negative-QTOF	splash10-0a4i-9000000000-722b10d68ba035f6a8c2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Streptozocin 10V, Positive-QTOF	splash10-000t-1090000000-4646c5accac0f8935a29	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Streptozocin 20V, Positive-QTOF	splash10-01ox-9000000000-d7d9d98474284352116c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Streptozocin 40V, Positive-QTOF	splash10-03di-9300000000-9cad9495adf263c410f9	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00428	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00428	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00428

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

27273

KEGG Compound ID

C07313

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Streptozocin

METLIN ID

Not Available

PubChem Compound

29327

PDB ID

Not Available

ChEBI ID

9288

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Wang Z, Gleichmann H: GLUT2 in pancreatic islets: crucial target molecule in diabetes induced with multiple low doses of streptozotocin in mice. Diabetes. 1998 Jan;47(1):50-6. [PubMed:9421374 ]
Schnedl WJ, Ferber S, Johnson JH, Newgard CB: STZ transport and cytotoxicity. Specific enhancement in GLUT2-expressing cells. Diabetes. 1994 Nov;43(11):1326-33. [PubMed:7926307 ]
Mansford KR, Opie L: Comparison of metabolic abnormalities in diabetes mellitus induced by streptozotocin or by alloxan. Lancet. 1968 Mar 30;1(7544):670-1. [PubMed:4170654 ]
Brentjens R, Saltz L: Islet cell tumors of the pancreas: the medical oncologist's perspective. Surg Clin North Am. 2001 Jun;81(3):527-42. [PubMed:11459269 ]
VAVRA JJ, DEBOER C, DIETZ A, HANKA LJ, SOKOLSKI WT: Streptozotocin, a new antibacterial antibiotic. Antibiot Annu. 1959-1960;7:230-5. [PubMed:13841501 ]
BC Cancer Agency [Link]

Enzymes

Enzyme Details

1. Solute carrier family 2, facilitated glucose transporter member 2

General function:: Involved in glucose transmembrane transporter activity
Specific function:: Facilitative glucose transporter. This isoform likely mediates the bidirectional transfer of glucose across the plasma membrane of hepatocytes and is responsible for uptake of glucose by the beta cells; may comprise part of the glucose-sensing mechanism of the beta cell. May also participate with the Na(+)/glucose cotransporter in the transcellular transport of glucose in the small intestine and kidney.
Gene Name:: SLC2A2
Uniprot ID:: P11168
Molecular weight:: 57488.955

References

Wang Z, Gleichmann H: GLUT2 in pancreatic islets: crucial target molecule in diabetes induced with multiple low doses of streptozotocin in mice. Diabetes. 1998 Jan;47(1):50-6. [PubMed:9421374 ]
Schnedl WJ, Ferber S, Johnson JH, Newgard CB: STZ transport and cytotoxicity. Specific enhancement in GLUT2-expressing cells. Diabetes. 1994 Nov;43(11):1326-33. [PubMed:7926307 ]

Transporters

Enzyme Details

1. Canalicular multispecific organic anion transporter 1

General function:: Involved in ATP binding
Specific function:: Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:: ABCC2
Uniprot ID:: Q92887
Molecular weight:: 174205.6

References

Cherrington NJ, Hartley DP, Li N, Johnson DR, Klaassen CD: Organ distribution of multidrug resistance proteins 1, 2, and 3 (Mrp1, 2, and 3) mRNA and hepatic induction of Mrp3 by constitutive androstane receptor activators in rats. J Pharmacol Exp Ther. 2002 Jan;300(1):97-104. [PubMed:11752103 ]

Enzyme Details

2. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Brady JM, Cherrington NJ, Hartley DP, Buist SC, Li N, Klaassen CD: Tissue distribution and chemical induction of multiple drug resistance genes in rats. Drug Metab Dispos. 2002 Jul;30(7):838-44. [PubMed:12065443 ]

Showing metabocard for Streptozocin (HMDB0014572)

MOL for HMDB0014572 (Streptozocin)

3D MOL for HMDB0014572 (Streptozocin)

3D SDF for HMDB0014572 (Streptozocin)

3D-SDF for HMDB0014572 (Streptozocin)

PDB for HMDB0014572 (Streptozocin)

3D PDB for HMDB0014572 (Streptozocin)

SMILES for HMDB0014572 (Streptozocin)

INCHI for HMDB0014572 (Streptozocin)

Structure for HMDB0014572 (Streptozocin)

3D Structure for HMDB0014572 (Streptozocin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

Transporters

References

References