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

• ChemBase ID: 169685
• 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?/m1/s1
• InChIKey: OGLCQHRZUSEXNB-UCDXPBRXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,3aS,6R)-3,5,6-trihydroxy-hexahydrofuro[3,2-b]furan-2-one
• IUPAC Traditional name: (3S,3aS,6R)-3,5,6-trihydroxy-tetrahydro-3H-furo[3,2-b]furan-2-one
• Synonyms: L-Glucuronic Acid γ-Lactone; L-Glucurono-3,6-lactone

Database IDs

• CAS Number: 32449-80-2
• PubChem SID: 162263817
• PubChem CID: 71317103

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

DETAILS

Toronto Research Chemicals - G596905

A glucuronic acid derivative. Used in the idurone synthesis.