NP-MRD: Showing NP-Card for Streptozotocin (NP0137348)

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Record Information

Version

2.0

Created at

2022-05-30 16:49:42 UTC

Updated at

2022-05-30 16:49:42 UTC

NP-MRD ID

NP0137348

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Streptozotocin

Description

STREPTOZOTOCIN, also known as streptozocin or zanosar, belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. STREPTOZOTOCIN is an extremely weak basic (essentially neutral) compound (based on its pKa). Streptozotocin is now long off patent and many generic formulations are available. Due to its high toxicity to beta cells, in scientific research, streptozotocin has also been long used for inducing insulitis and diabetes on experimental animals. Recent advancements in understanding the biosynthesis of this natural product have been made by Balskus et al. This explains its relative toxicity to beta cells, since these cells have relatively high levels of GLUT2. In the 1960s and 1970s, the National Cancer Institute investigated streptozotocin's use in cancer chemotherapy.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 33  0  0  0  0  0  0  0  0999 V2000
    4.8057    0.1659    1.5380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8312    0.1560    0.4682 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3324    0.2523   -0.8322 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2459   -0.4600   -1.2734 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4464    0.0535    0.7428 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0677   -0.0297    1.9392 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4533    0.0389   -0.2543 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0380   -0.0669    0.0521 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5526   -1.3379   -0.4887 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1544   -2.4092    0.3059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9115   -1.3543   -0.6050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4940   -0.3690    0.1727 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9815   -0.6032    0.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5772   -0.5760   -0.9978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1849    0.9465   -0.5463 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4069    0.8057   -1.9270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7084    1.1781   -0.3592 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1923    1.7490   -1.5102 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3541    0.6548    2.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0857   -0.8606    1.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7161    0.6856    1.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7960    0.1102   -1.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0366   -0.1251    1.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1276   -1.5269   -1.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2939   -2.1757    1.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0801   -0.3021    1.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4623    0.1149    0.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1602   -1.6160    0.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0202    0.3232   -1.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7599    1.7720   -0.1249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6239    0.4401   -2.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5890    1.9565    0.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8553    2.4093   -1.8506 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  6
 10 25  1  0
 12 26  1  1
 13 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  1
 16 31  1  0
 17 32  1  1
 18 33  1  0
M  END


  Mrv1533004181500002D          

 18 18  0  0  0  0            999 V2000
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  2  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137348

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN(N=O)C(=O)NC1C(O)OC(CO)C(O)C1O

> <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)

> <INCHI_KEY>
ZSJLQEPLLKMAKR-UHFFFAOYSA-N

> <FORMULA>
C8H15N3O7

> <MOLECULAR_WEIGHT>
265.222

> <EXACT_MASS>
265.090999835

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
23.87387496960638

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methyl-3-nitroso-1-[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>
151.92

> <JCHEM_REFRACTIVITY>
55.9552

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.35e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.667  -4.620   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       1.334  -5.390   0.000  0.00  0.00           N+0
HETATM    4  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       5.335  -4.620   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    8   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
Streptozocin	MeSH
Streptozotocine	MeSH
2-Deoxy-2-((methylnitrosoamino)carbonyl)amino-D-glucose	MeSH
Zanosar	MeSH
2,4,5-Trihydroxy-6-(hydroxymethyl)-N-methyl-N-nitrosooxane-3-carbamimidate	Generator

Chemical Formula

C₈H₁₅N₃O₇

Average Mass

265.2220 Da

Monoisotopic Mass

265.09100 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CN(N=O)C(=O)NC1C(O)OC(CO)C(O)C1O

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)

InChI Key

ZSJLQEPLLKMAKR-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Monosaccharides

Alternative Parents

Substituents

Monosaccharide
Oxane
Organic n-nitroso compound
Hemiacetal
Secondary alcohol
Organic nitroso compound
Carboximidic acid derivative
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Alcohol
Primary alcohol
Hydrocarbon derivative
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

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	-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	23.87 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Streptozotocin

METLIN ID

Not Available

PubChem Compound

5300

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Streptozotocin (NP0137348)

MOL for NP0137348 (Streptozotocin)

3D MOL for NP0137348 (Streptozotocin)

3D SDF for NP0137348 (Streptozotocin)

3D-SDF for NP0137348 (Streptozotocin)

PDB for NP0137348 (Streptozotocin)

3D PDB for NP0137348 (Streptozotocin)

SMILES for NP0137348 (Streptozotocin)

INCHI for NP0137348 (Streptozotocin)

Structure for NP0137348 (Streptozotocin)

3D Structure for NP0137348 (Streptozotocin)