[(3S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-ylidene]amino N-phenylcarbamate

• ChemBase ID: 169658
• Molecular Formular: C13H16N2O7
• Molecular Mass: 312.27534
• Monoisotopic Mass: 312.09575086
• SMILES: O1/C(=N/OC(=O)Nc2ccccc2)/[C@@H](C([C@@H](C1CO)O)O)O
• Canonical SMILES: OCC1O/C(=N/OC(=O)Nc2ccccc2)/[C@@H](C([C@@H]1O)O)O
• InChI: InChI=1S/C13H16N2O7/c16-6-8-9(17)10(18)11(19)12(21-8)15-22-13(20)14-7-4-2-1-3-5-7/h1-5,8-11,16-19H,6H2,(H,14,20)/b15-12+/t8?,9-,10?,11+/m1/s1
• InChIKey: GPIOBIZYEXDBSE-OPVLAPPMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(3S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-ylidene]amino N-phenylcarbamate
• IUPAC Traditional name: [(3S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-ylidene]amino N-phenylcarbamate
• Synonyms: PUGLU; O-(D-Glucopyranosylidene)amino N-Phenylcarbamate

Database IDs

• CAS Number: 104012-84-2
• PubChem SID: 162263790
• PubChem CID: 45039349

CALCULATED PROPERTIES

• Acid pKa: 11.897172
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -0.71826833
• LogD (pH = 7.4): -0.7182817
• Log P: -0.71826816
• Molar Refractivity: 73.1527 cm^3
• Polarizability: 28.506332 Å^3
• Polar Surface Area: 140.84 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Foam

DETAILS

Toronto Research Chemicals - G432000

A beta-Glucosidase inhibitor.

REFERENCES

• Miller, D.J., et al.: Development, 118, 1279 (1993)