(2S,3S,4S,5R,6S)-6-{[(3S,3aR,6R,6aS)-6-(nitrooxy)-hexahydro(2,3,3a,5,6,6a-13C6)furo[3,2-b]furan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 171976
• Molecular Formular: C12H17NO12
• Molecular Mass: 373.21880903
• Monoisotopic Mass: 373.09520402
• SMILES: [13C@@H]12[13C@@H]([13C@@H]([13CH2]O1)O[N+](=O)[O-])O[13CH2][13C@@H]2O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: [O-][N+](=O)O[13C@@H]1[13CH2]O[13C@H]2[13C@@H]1O[13CH2][13C@@H]2O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C12H17NO12/c14-5-6(15)10(11(17)18)24-12(7(5)16)23-3-1-21-9-4(25-13(19)20)2-22-8(3)9/h3-10,12,14-16H,1-2H2,(H,17,18)/t3-,4+,5-,6-,7+,8+,9+,10-,12+/m0/s1/i1+1,2+1,3+1,4+1,8+1,9+1
• InChIKey: MQHSDQNPAIOBOQ-BKYBPGNXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[(3S,3aR,6R,6aS)-6-(nitrooxy)-hexahydro(2,3,3a,5,6,6a-^1^3C₆)furo[3,2-b]furan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[(3S,3aR,6R,6aS)-6-(nitrooxy)-hexahydro(2,3,3a,5,6,6a-^1^3C₆)furo[3,2-b]furan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1,4:3,6-Dianhydro-2-O-β-D-glucopyranuronosyl-D-glucitol-13C6 5-Nitrate; Isosorbide 5-Mononitrate-13C6 2-β-D-Glucuronide

Database IDs

• PubChem SID: 164227886
• PubChem CID: 71749633

CALCULATED PROPERTIES

• Acid pKa: 3.244002
• H Acceptors: 12
• H Donor: 4
• LogD (pH = 5.5): -4.1680794
• LogD (pH = 7.4): -5.369601
• Log P: -1.9322213
• Molar Refractivity: 70.3581 cm^3
• Polarizability: 29.181364 Å^3
• Polar Surface Area: 189.96 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - I902112

A labelled metabolite of Isosorbide 5-Mononitrate (I902100).

REFERENCES

• Abshagen, U., et al.: Eur. J. Clin. Pharmacol., 27, 637 (1985)