(3S,3aS,6R,6aR)-6-hydroxy-hexahydro(2,3,3a,5,6,6a-13C6)furo[3,2-b]furan-3-yl nitrate

• ChemBase ID: 171977
• Molecular Formular: C6H9NO6
• Molecular Mass: 197.09468903
• Monoisotopic Mass: 197.06311604
• SMILES: [13C@@H]12[13C@@H]([13C@H]([13CH2]O1)O[N+](=O)[O-])O[13CH2][13C@H]2O
• Canonical SMILES: [O-][N+](=O)O[13C@H]1[13CH2]O[13C@H]2[13C@@H]1O[13CH2][13C@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/i1+1,2+1,3+1,4+1,5+1,6+1
• InChIKey: YWXYYJSYQOXTPL-GVZKVBLJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,3aS,6R,6aR)-6-hydroxy-hexahydro(2,3,3a,5,6,6a-^1^3C₆)furo[3,2-b]furan-3-yl nitrate
• IUPAC Traditional name: (3S,3aS,6R,6aR)-6-hydroxy-hexahydro(2,3,3a,5,6,6a-^1^3C₆)furo[3,2-b]furan-3-yl nitrate
• Synonyms: 1,4:3,6-Dianhydro-D-glucitol-13C6 2-Nitrate; 6-Nitrooxyhexahydro-furo[3,2-b]furan-3-ol-13C6; 1,4:3,6-Dianhydro-D-glucitol-13C6 2-mononitrate; Isosorbide-13C6 2-Mononitrate; Isosorbide-13C6 2-Nitrate

Database IDs

• PubChem SID: 164227887
• PubChem CID: 71749634

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

DETAILS

Toronto Research Chemicals - I902152

A labelled 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)