potassium [(2R,3S,4R,5R,6R)-5-acetamido-3,4-dihydroxy-6-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxan-2-yl]methyl sulfate

• ChemBase ID: 174531
• Molecular Formular: C18H20KNO11S
• Molecular Mass: 497.5148
• Monoisotopic Mass: 497.03941315
• SMILES: c1(ccc2c(c1)oc(=O)cc2C)O[C@@H]1[C@H]([C@H]([C@@H]([C@@H](O1)COS(=O)(=O)[O-])O)O)NC(=O)C.[K+]
• Canonical SMILES: CC(=O)N[C@@H]1[C@H](O[C@H]([C@H]([C@@H]1O)O)COS(=O)(=O)[O-])Oc1ccc2c(c1)oc(=O)cc2C.[K+]
• InChI: InChI=1S/C18H21NO11S.K/c1-8-5-14(21)29-12-6-10(3-4-11(8)12)28-18-15(19-9(2)20)17(23)16(22)13(30-18)7-27-31(24,25)26;/h3-6,13,15-18,22-23H,7H2,1-2H3,(H,19,20)(H,24,25,26);/q;+1/p-1/t13-,15-,16-,17-,18+;/m1./s1
• InChIKey: TYSZCFCWZWWIHC-FBFKMQNYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: potassium [(2R,3S,4R,5R,6R)-5-acetamido-3,4-dihydroxy-6-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxan-2-yl]methyl sulfate
• IUPAC Traditional name: potassium [(2R,3S,4R,5R,6R)-5-acetamido-3,4-dihydroxy-6-[(4-methyl-2-oxochromen-7-yl)oxy]oxan-2-yl]methyl sulfate
• Synonyms: 7-[[2-(Acetylamino)-2-deoxy-6-O-sulfo-α-D-glucopyranosyl]oxy]-4-methyl-2H-1-benzopyran-2-one Monopotassium Salt; 4-Methylumbelliferyl 6-Sulfo-2-acetamido-2-deoxy-α-D-glucopyranoside Potassium Salt

Database IDs

• CAS Number: 210357-37-2
• PubChem SID: 164230441
• PubChem CID: 71750700

CALCULATED PROPERTIES

• Acid pKa: -2.1009114
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -3.0983253
• LogD (pH = 7.4): -3.098345
• Log P: -2.6951046
• Molar Refractivity: 99.9273 cm^3
• Polarizability: 40.945175 Å^3
• Polar Surface Area: 180.75 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Yellow Solid
• Melting Point: 195-197°C

Safety Information

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

DETAILS

Toronto Research Chemicals - M334950

Shown to be a substrate for the lysosomal N-acetylglucosamine-6-sulphate sulphatase.

REFERENCES

• He, W., et al.: J. inher. Metab. Dis., 16, 935 (1993)