(3S,3aS,6R,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl nitrate

• ChemBase ID: 121649
• Molecular Formular: C6H9NO6
• Molecular Mass: 191.13876
• Monoisotopic Mass: 191.04298701
• SMILES: [N+](=O)(O[C@@H]1[C@@H]2[C@H](OC1)[C@@H](CO2)O)[O-]
• Canonical SMILES: [O-][N+](=O)O[C@H]1CO[C@H]2[C@@H]1OC[C@H]2O
• InChI: InChI=1S/C6H9NO6/c8-3-1-11-6-4(13-7(9)10)2-12-5(3)6/h3-6,8H,1-2H2/t3-,4+,5-,6-/m1/s1
• InChIKey: YWXYYJSYQOXTPL-JGWLITMVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,3aS,6R,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl nitrate
• IUPAC Traditional name: (3S,3aS,6R,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl nitrate; isosorbide 5-mononitrate
• Synonyms: (3S,3aS,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl nitrate; Isosorbide-2-mononitrate; 1,4:3,6-Dianhydro-D-glucitol 2-Nitrate; 6-Nitrooxyhexahydro-furo[3,2-b]furan-3-ol; 1,4:3,6-Dianhydro-D-glucitol 2-mononitrate; Isosorbide 2-Mononitrate; Isosorbide 2-Nitrate

Database IDs

• CAS Number: 16106-20-0
• PubChem SID: 162216002
• PubChem CID: 62989

CALCULATED PROPERTIES

• Acid pKa: 13.335235
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -0.48166016
• LogD (pH = 7.4): -0.48166066
• Log P: -0.48166016
• Molar Refractivity: 38.0774 cm^3
• Polarizability: 15.319396 Å^3
• Polar Surface Area: 93.74 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol
• Apperance: Low Melting White Solid

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Mechanism of Action: Effector of EDRF

Product Information

• Application(s): Cardiant

DETAILS

Toronto Research Chemicals - I902150

A metabolite of Isosorbide Dinitrate. Used as an antianginal.

REFERENCES

• Goldberg, et al.: Acta Physiol. Scand., 15, 173 (1948)
• Silvieri, L.A., et al.: Anal. Profiles Drug Subs., 4, 225 (1948)
• Laufen, H., et al.: Arzneim.-Forsch., 33, 980 (1948)