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

• ChemBase ID: 174530
• Molecular Formular: C16H18NNaO10S
• Molecular Mass: 439.36959
• Monoisotopic Mass: 439.05491106
• 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-].[Na+]
• 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-].[Na+]
• InChI: InChI=1S/C16H19NO10S.Na/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);/q;+1/p-1/t11-,13-,14-,15-,16+;/m1./s1
• InChIKey: LMECUNAMBHBGFU-MYDYNYEJSA-M

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 460085-45-4
• PubChem SID: 164230440
• PubChem CID: 23676104

CALCULATED PROPERTIES

• Acid pKa: -1.4146138
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -3.539727
• LogD (pH = 7.4): -3.5615065
• Log P: -2.54967
• Molar Refractivity: 90.7758 cm^3
• Polarizability: 37.088448 Å^3
• Polar Surface Area: 174.68 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol (Sparingly); Water
• Apperance: White Solid
• Melting Point: 224-229°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M334851

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

REFERENCES

• Karpova, E.A., et al.: J. Inher. Metab. Dis., 19, 278 (1996)
• Dasgupta, F., et al.: Carbohydrate Res., 337, 1055 (1996)