NP-MRD: Showing NP-Card for (2s,3r,4r,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)-n-methyl-n-nitrosooxane-3-carbamimidic acid (NP0224326)

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Record Information

Version

2.0

Created at

2022-09-06 02:39:25 UTC

Updated at

2022-09-06 02:39:25 UTC

NP-MRD ID

NP0224326

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4r,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)-n-methyl-n-nitrosooxane-3-carbamimidic acid

Description

Streptozocin, also known as zanosar, 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. Streptozocin is a drug which is used for the treatment of malignant neoplasms of pancreas (metastatic islet cell carcinoma). Streptozocin is an extremely weak basic (essentially neutral) compound (based on its pKa). (2s,3r,4r,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)-n-methyl-n-nitrosooxane-3-carbamimidic acid is found in Apis cerana and Streptomyces alanosinicus. (2s,3r,4r,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)-n-methyl-n-nitrosooxane-3-carbamimidic acid was first documented in 1959 (PMID: 13841501). Streptozocin is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound (PMID: 4170654) (PMID: 7926307) (PMID: 9421374).

Structure

MOL SDF PDB SMILES InChI

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>
NP0224326

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

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 Mass

265.2206 Da

Monoisotopic Mass

265.09100 Da

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

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Streptomyces alanosinicus	LOTUS Database	35616633

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 )

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	23.74 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

External Links

HMDB ID

HMDB0014572

DrugBank ID

DB00428

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

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. doi: 10.1016/s0140-6736(68)92103-x. [PubMed:4170654 ]
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. doi: 10.2337/diab.43.11.1326. [PubMed:7926307 ]
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. doi: 10.2337/diab.47.1.50. [PubMed:9421374 ]
VAVRA JJ, DEBOER C, DIETZ A, HANKA LJ, SOKOLSKI WT: Streptozotocin, a new antibacterial antibiotic. Antibiot Annu. 1959-1960;7:230-5. [PubMed:13841501 ]
LOTUS database [Link]

Showing NP-Card for (2s,3r,4r,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)-n-methyl-n-nitrosooxane-3-carbamimidic acid (NP0224326)

MOL for NP0224326 ((2s,3r,4r,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)-n-methyl-n-nitrosooxane-3-carbamimidic acid)

3D MOL for NP0224326 ((2s,3r,4r,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)-n-methyl-n-nitrosooxane-3-carbamimidic acid)

3D SDF for NP0224326 ((2s,3r,4r,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)-n-methyl-n-nitrosooxane-3-carbamimidic acid)

3D-SDF for NP0224326 ((2s,3r,4r,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)-n-methyl-n-nitrosooxane-3-carbamimidic acid)

PDB for NP0224326 ((2s,3r,4r,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)-n-methyl-n-nitrosooxane-3-carbamimidic acid)

3D PDB for NP0224326 ((2s,3r,4r,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)-n-methyl-n-nitrosooxane-3-carbamimidic acid)

SMILES for NP0224326 ((2s,3r,4r,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)-n-methyl-n-nitrosooxane-3-carbamimidic acid)

INCHI for NP0224326 ((2s,3r,4r,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)-n-methyl-n-nitrosooxane-3-carbamimidic acid)

Structure for NP0224326 ((2s,3r,4r,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)-n-methyl-n-nitrosooxane-3-carbamimidic acid)

3D Structure for NP0224326 ((2s,3r,4r,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)-n-methyl-n-nitrosooxane-3-carbamimidic acid)