N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxan-3-yl]sulfamic acid

• ChemBase ID: 174529
• Molecular Formular: C16H19NO10S
• Molecular Mass: 417.38776
• Monoisotopic Mass: 417.07296681
• SMILES: c1c(cc2c(c1)c(cc(=O)o2)C)O[C@@H]1[C@H]([C@H]([C@@H]([C@@H](O1)CO)O)O)NS(=O)(=O)O
• Canonical SMILES: OC[C@@H]1O[C@H](Oc2ccc3c(c2)oc(=O)cc3C)[C@H]([C@H]([C@@H]1O)O)NS(=O)(=O)O
• InChI: InChI=1S/C16H19NO10S/c1-7-4-12(19)26-10-5-8(2-3-9(7)10)25-16-13(17-28(22,23)24)15(21)14(20)11(6-18)27-16/h2-5,11,13-18,20-21H,6H2,1H3,(H,22,23,24)/t11-,13-,14-,15-,16+/m1/s1
• InChIKey: WTEDCRZHOZSQII-BTAUDXDXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxan-3-yl]sulfamic acid
• IUPAC Traditional name: N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(4-methyl-2-oxochromen-7-yl)oxy]oxan-3-yl]sulfamic acid
• Synonyms: 7-[[2-Deoxy-2-(sulfoamino)-α-D-glucopyranosyl]oxy]-4-methyl-2H-1-benzopyran-2-one; 4-Methylumbelliferyl 2-Sulfamino-2-deoxy-α-D-glucopyranosideDISCONTINUED see M334851

Database IDs

• CAS Number: 180088-52-2
• PubChem SID: 164230439
• PubChem CID: 11316590

CALCULATED PROPERTIES

• Acid pKa: -1.4146138
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -3.539727
• LogD (pH = 7.4): -3.5615065
• Log P: -2.54967
• Molar Refractivity: 91.8975 cm^3
• Polarizability: 37.370697 Å^3
• Polar Surface Area: 171.85 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Powder
• Melting Point: >250°C dec.

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M334850

A substrate for the lysosomal heparin sulphamidase. A fluorometric enzyme assay for the diagnosis of Sanfilippo disease type A (MPS IIIA).

REFERENCES

• Karpova, E.A., et al.: J. Inher. Metab. Dis., 19, 278 (1996)