4-[(nitrooxy)methyl]phenyl 2-(acetyloxy)benzoate

• ChemBase ID: 175461
• Molecular Formular: C16H13NO7
• Molecular Mass: 331.27692
• Monoisotopic Mass: 331.06920176
• SMILES: c1cccc(c1C(=O)Oc1ccc(cc1)CO[N+](=O)[O-])OC(=O)C
• Canonical SMILES: [O-][N+](=O)OCc1ccc(cc1)OC(=O)c1ccccc1OC(=O)C
• InChI: InChI=1S/C16H13NO7/c1-11(18)23-15-5-3-2-4-14(15)16(19)24-13-8-6-12(7-9-13)10-22-17(20)21/h2-9H,10H2,1H3
• InChIKey: CTHNKWFUDCMLIQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(nitrooxy)methyl]phenyl 2-(acetyloxy)benzoate
• IUPAC Traditional name: 4-[(nitrooxy)methyl]phenyl 2-(acetyloxy)benzoate
• Synonyms: 2-(Acetyloxy)benzoic Acid 4-[(Nitrooxy)methyl]phenyl Ester; NCX 4040; NO-Aspirin

Database IDs

• CAS Number: 287118-97-2
• PubChem SID: 164231371
• PubChem CID: 9818919

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 3.399544
• LogD (pH = 7.4): 3.399544
• Log P: 3.399544
• Molar Refractivity: 82.5032 cm^3
• Polarizability: 31.457886 Å^3
• Polar Surface Area: 107.65 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: Pale Yellow Solid
• Melting Point: 83-86°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N633005

A novel nitric oxide-releasing aspirin, Nitro-aspirin inhibits MCF-7 breast cancer cell growth. A cyclooxygenase 2 inhibitor.

REFERENCES

• Janicke, R., et al.: J. Biol. Chem., 273, 15540 (1998)
• Schiff, R., et al.: Clin. Cancer Res., 9, 447S (1998)
• Kashfi, K., et al.: Biochem. Pharmacol., 70, 969 ( 2005), Han, A., et al.: Eur. J. Pharmacol., 583, 26 (1998)