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

• ChemBase ID: 156843
• Molecular Formular: C13H16N2O7
• Molecular Mass: 312.27534
• Monoisotopic Mass: 312.09575086
• SMILES: c1ccc(cc1)NC(=O)O/N=C/1\[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• Canonical SMILES: OC[C@H]1O/C(=N/OC(=O)Nc2ccccc2)/[C@@H]([C@H]([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)/t8-,9-,10+,11-/m1/s1
• InChIKey: GPIOBIZYEXDBSE-CHWFTXMASA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 104012-84-2
• MDL Number: MFCD00145030
• Beilstein Number: 4881004
• PubChem SID: 24872648; 162250980
• PubChem CID: 5487947

CALCULATED PROPERTIES

• Acid pKa: 11.897172
• H Acceptors: 9
• 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

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥85% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C13H16N2O7

DETAILS

Sigma Aldrich - 49125

Other Notes
Highly active inhibitor of β-D-glucosidase1