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

• ChemBase ID: 174525
• Molecular Formular: C16H14Na2O12S
• Molecular Mass: 476.3197
• Monoisotopic Mass: 476.00013545
• SMILES: [C@@H]1([C@H]([C@@H]([C@H]([C@@H](O1)Oc1ccc2c(c1)oc(=O)cc2C)OS(=O)(=O)[O-])O)O)C(=O)[O-].[Na+].[Na+]
• Canonical SMILES: [O-]C(=O)[C@@H]1O[C@@H](Oc2ccc3c(c2)oc(=O)cc3C)[C@@H]([C@H]([C@@H]1O)O)OS(=O)(=O)[O-].[Na+].[Na+]
• InChI: InChI=1S/C16H16O12S.2Na/c1-6-4-10(17)26-9-5-7(2-3-8(6)9)25-16-14(28-29(22,23)24)12(19)11(18)13(27-16)15(20)21;;/h2-5,11-14,16,18-19H,1H3,(H,20,21)(H,22,23,24);;/q;2*+1/p-2/t11-,12-,13+,14+,16+;;/m0../s1
• InChIKey: BGWMBPGUPUSUIU-CEWNINSASA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium (2R,3S,4S,5R,6S)-3,4-dihydroxy-6-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]-5-(sulfonatooxy)oxane-2-carboxylate
• IUPAC Traditional name: disodium (2R,3S,4S,5R,6S)-3,4-dihydroxy-6-[(4-methyl-2-oxochromen-7-yl)oxy]-5-(sulfonatooxy)oxane-2-carboxylate
• Synonyms: 4-Methylumbelliferyl α-L-Iduronic Acid-2-sulfate Sodium Salt; 4-Methyl-2-oxo-2H-1-benzopyran-7-yl α-L-Idopyranosiduronic Acid 2-(Hydrogen Sulfate); 4-Methylumbelliferyl α-L-Idopyranosiduronic Acid 2-Sulfate Disodium Salt

Database IDs

• PubChem SID: 164230435
• PubChem CID: 71750698

CALCULATED PROPERTIES

• Acid pKa: -2.1564047
• H Acceptors: 10
• H Donor: 2
• LogD (pH = 5.5): -5.196666
• LogD (pH = 7.4): -5.9895983
• Log P: -2.0711079
• Molar Refractivity: 99.5305 cm^3
• Polarizability: 36.583553 Å^3
• Polar Surface Area: 191.78 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethanol; Methanol; Water
• Apperance: White Solid
• Melting Point: >220°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - M334715

A fluorogenic substrate in the assay of α-L-Iduronidase. A fluorimetric enzyme assay for the diagnosis of MPS II (Hunter disease).

REFERENCES

• Matalon, R., et al.: Biochem. Biophys. Res. Commun., 47, 959 (1972)
• Voznyi, Y.V., et al.: J. Inherit. Metab. Dis., 24, 675 (2001)