(3S,3aR,6S)-3,5,6-trihydroxy-hexahydrofuro[3,2-b]furan-2-one

• ChemBase ID: 169684
• Molecular Formular: C6H8O6
• Molecular Mass: 176.12412
• Monoisotopic Mass: 176.03208798
• SMILES: C12[C@@H](OC([C@H]1O)O)[C@@H](C(=O)O2)O
• Canonical SMILES: O[C@@H]1C(O)O[C@@H]2C1OC(=O)[C@H]2O
• InChI: InChI=1S/C6H8O6/c7-1-3-4(12-5(1)9)2(8)6(10)11-3/h1-5,7-9H/t1-,2-,3?,4+,5?/m0/s1
• InChIKey: OGLCQHRZUSEXNB-ZAZZRNQYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,3aR,6S)-3,5,6-trihydroxy-hexahydrofuro[3,2-b]furan-2-one
• IUPAC Traditional name: (3S,3aR,6S)-3,5,6-trihydroxy-tetrahydro-3H-furo[3,2-b]furan-2-one
• Synonyms: D-Glucuronic Acid γ-Lactone; D-Glucurono-6,3-lactone; D-Glucuronolactone; Dicurone; Glucoxy; Glucurolactone; Glucurono-6,3-lactone; Glucuronolactone; Glucuronosan; Glycurone; Guronsan; NSC 656; Reulatt S.S.; D-Glucurono-3,6-lactone

Database IDs

• CAS Number: 32449-92-6
• PubChem SID: 162263816
• PubChem CID: 46780443

CALCULATED PROPERTIES

• Acid pKa: 11.14436
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.9477946
• LogD (pH = 7.4): -1.9478717
• Log P: -1.9477936
• Molar Refractivity: 32.2986 cm^3
• Polarizability: 14.018171 Å^3
• Polar Surface Area: 96.22 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 177-180°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - G596900

A glucuronic acid derivative. It is used for treating canine hepatitis.

REFERENCES

• Glassbrook, N., et al.: Nat. Biotechnol., 18, 1142 (2000)
• Nicholson, J., et al.: Xenobiotica, 29, 1181 (2000)
• Gullberg, J., et al.: Anal. Biochem., 331, 283 (2000)