sodium (2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxane-2-carboxylate

• ChemBase ID: 174523
• Molecular Formular: C16H15NaO9
• Molecular Mass: 374.27467
• Monoisotopic Mass: 374.06137634
• SMILES: [C@@H]1([C@H]([C@@H]([C@H]([C@@H](O1)Oc1ccc2c(c1)oc(=O)cc2C)O)O)O)C(=O)[O-].[Na+]
• Canonical SMILES: [O-]C(=O)[C@@H]1O[C@@H](Oc2ccc3c(c2)oc(=O)cc3C)[C@@H]([C@H]([C@@H]1O)O)O.[Na+]
• InChI: InChI=1S/C16H16O9.Na/c1-6-4-10(17)24-9-5-7(2-3-8(6)9)23-16-13(20)11(18)12(19)14(25-16)15(21)22;/h2-5,11-14,16,18-20H,1H3,(H,21,22);/q;+1/p-1/t11-,12-,13+,14+,16+;/m0./s1
• InChIKey: DJVQUWOKCARXPZ-OMZMBYLHSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxane-2-carboxylate
• IUPAC Traditional name: sodium (2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(4-methyl-2-oxochromen-7-yl)oxy]oxane-2-carboxylate
• Synonyms: 4-Methylumbelliferyl α-L-Iduronic Acid, Sodium Salt; 4-Methylumbelliferyl α-L-Idopyranosiduronic Acid, Sodium Salt

Database IDs

• CAS Number: 89157-94-8
• PubChem SID: 164230433
• PubChem CID: 71307170

CALCULATED PROPERTIES

• Acid pKa: 2.9729717
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -2.6557503
• LogD (pH = 7.4): -3.6463246
• Log P: -0.16860466
• Molar Refractivity: 90.6604 cm^3
• Polarizability: 31.74887 Å^3
• Polar Surface Area: 145.58 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethanol; Methanol; Water
• Apperance: White Solid
• Melting Point: 193-195°C

Safety Information

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

DETAILS

Toronto Research Chemicals - M334701

A fluorogenic substrate in the assay of a-L-Iduronidase. Useful for the detection of Hurlers syndrome.

REFERENCES

• Matalon, R., et al.: Biochem. Biophys. Res. Commun., 47, 959 (1972)