2-[(2S,3R,4R)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyacetic acid

• ChemBase ID: 171507
• Molecular Formular: C6H8O7
• Molecular Mass: 192.12352
• Monoisotopic Mass: 192.0270026
• SMILES: [C@H]1([C@H]([C@H](C(=O)O1)O)O)C(C(=O)O)O
• Canonical SMILES: OC(=O)C([C@H]1OC(=O)[C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C6H8O7/c7-1-2(8)6(12)13-4(1)3(9)5(10)11/h1-4,7-9H,(H,10,11)/t1-,2-,3?,4+/m1/s1
• InChIKey: XECPAIJNBXCOBO-YDQMYBSPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2S,3R,4R)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyacetic acid
• IUPAC Traditional name: [(2S,3R,4R)-3,4-dihydroxy-5-oxooxolan-2-yl](hydroxy)acetic acid
• Synonyms: L-Idaro-1,4-lactone; L-Idaric-1,4-lactone

Database IDs

• CAS Number: 80876-59-1
• PubChem SID: 164227417
• PubChem CID: 16396806

CALCULATED PROPERTIES

• Acid pKa: 3.0635793
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -4.8292956
• LogD (pH = 7.4): -5.891565
• Log P: -2.4249988
• Molar Refractivity: 34.6462 cm^3
• Polarizability: 14.693422 Å^3
• Polar Surface Area: 124.29 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 145-147°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - I165000

An inhibitor of α-L-idosidurnase.

REFERENCES

• Herd, J.K., et al.: Carbohydrate Res., 99, 33-39 (1982)