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

• ChemBase ID: 175460
• Molecular Formular: C16H13NO7
• Molecular Mass: 331.27692
• Monoisotopic Mass: 331.06920176
• SMILES: c1cccc(c1C(=O)Oc1cc(ccc1)CO[N+](=O)[O-])OC(=O)C
• Canonical SMILES: [O-][N+](=O)OCc1cccc(c1)OC(=O)c1ccccc1OC(=O)C
• InChI: InChI=1S/C16H13NO7/c1-11(18)23-15-8-3-2-7-14(15)16(19)24-13-6-4-5-12(9-13)10-22-17(20)21/h2-9H,10H2,1H3
• InChIKey: IOJUJUOXKXMJNF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(nitrooxy)methyl]phenyl 2-(acetyloxy)benzoate
• IUPAC Traditional name: 3-[(nitrooxy)methyl]phenyl 2-(acetyloxy)benzoate
• Synonyms: 2-Acetyloxybenzoic Acid 3-Nitrooxymethylphenyl Ester; 3-(Nitroxymethyl)phenyl 2-acetoxybenzoate; NCX 4016; NO-Aspirin 1

Database IDs

• CAS Number: 175033-36-0
• PubChem SID: 164231370
• PubChem CID: 119032

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: 31.457937 Å^3
• Polar Surface Area: 107.65 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetonitrile; Chloroform; Dichloromethane
• Apperance: Off-White Solid
• Melting Point: 61-62°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N633000

NO-Aspirin 1 is a hybrid molecule of aspirin and a nitric oxide (NO) donor. It contains an ester linkage, that when cleaved by esterases in the gut, liver, and plasma releases salicylate and an NO-releasing moiety. It also prevents restinosiis, inhibit

REFERENCES

• Wallace, J.F., et al.: Drug Development Res., 42, 144 (1997)
• Takeuchi, K, et al.: J. Physiol. Pharmacol., 49, 501 (1997)
• Bak, A.W., et al.: Life Sci., 62, 367 (1997)
• Wallace, J.L., et al.: Nature Reviews Drug Discovery, 1, 375 (1997)
• Chiroli, V., et a