(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)-N-methyl-N-nitrosooxane-3-carbamimidic acid

• ChemBase ID: 102205
• Molecular Formular: C8H15N3O7
• Molecular Mass: 265.2206
• Monoisotopic Mass: 265.09099984
• SMILES: CN(/C(=N/[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@H]1O)O)O)/O)N=O
• Canonical SMILES: OC[C@H]1O[C@@H](O)[C@@H]([C@H]([C@@H]1O)O)/N=C(/N(N=O)C)\O
• InChI: 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
• InChIKey: ZSJLQEPLLKMAKR-NYMZXIIRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)-N-methyl-N-nitrosooxane-3-carbamimidic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)-N-methyl-N-nitrosooxane-3-carbamimidic acid
• Synonyms: STZ; 2-Deoxy-2-(3-methyl-3-nitrosoureido)-D-glucopyranose; Streptozocin, N-(Methylnitrosocarbamoyl)-α-D-glucosamine; STREPTOZOTOCIN

Database IDs

• CAS Number: 18883-66-4
• EC Number: 242-646-8
• PubChem SID: 162088150
• PubChem CID: 7067772

CALCULATED PROPERTIES

• Acid pKa: 7.5637026
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -1.9044147
• LogD (pH = 7.4): -2.1274488
• Log P: -1.9006814
• Molar Refractivity: 56.4769 cm^3
• Polarizability: 21.91624 Å^3
• Polar Surface Area: 155.41 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 115°C (dec.)

Safety Information

• Storage Condition: 2-8°C
• RTECS: LZ5775000
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 3077
• Hazard Class: 9
• Packing Group: III
• Australian Hazchem: 2X
• Risk Statements: R:45-58-36/37/38
• Safety Statements: S:28-29-36/37/39-45-53-61
• Emergency Response Guidebook(ERG) Number: 171

DETAILS

MP Biomedicals - 02100557

Crystalline Mixed Anomers
Potent methylating agent for DNA.

REFERENCES

• Bennett, R.A., and Pegg, A.E., Cancer Res., 41: 2786, (1981).