2-methyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanenitrile

• ChemBase ID: 172415
• Molecular Formular: C11H19NO6
• Molecular Mass: 261.27166
• Monoisotopic Mass: 261.12123733
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)OC(CC)(C)C#N)O)O)O
• Canonical SMILES: OC[C@@H]1O[C@@H](OC(C#N)(CC)C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C11H19NO6/c1-3-11(2,5-12)18-10-9(16)8(15)7(14)6(4-13)17-10/h6-10,13-16H,3-4H2,1-2H3/t6-,7-,8+,9-,10+,11?/m1/s1
• InChIKey: WEWBWVMTOYUPHH-GXUZYPEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanenitrile
• IUPAC Traditional name: 2-methyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanenitrile
• Synonyms: 2-(β-D-Glucopyranosyloxy)-2-methylbutyronitrile; (2R)-2-(β-D-Glucopyranosyloxy)-2-methyl-butanenitrile; Lotaustralin

Database IDs

• CAS Number: 534-67-8
• PubChem SID: 164228325
• PubChem CID: 23638286

CALCULATED PROPERTIES

• Acid pKa: 12.208422
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.229428
• LogD (pH = 7.4): -1.2294347
• Log P: -1.229428
• Molar Refractivity: 59.4697 cm^3
• Polarizability: 24.177946 Å^3
• Polar Surface Area: 123.17 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Semi-Solid

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - L471250

A bioactive constituent of Chinese natural medicines.

REFERENCES

• Masayuki, Y., et al.: Chem. Pharm. Bull., 45(9)
• 1498 (1997)