(1S,2S,3R,6S)-6-amino-4-(hydroxymethyl)cyclohex-4-ene-1,2,3-triol hydrochloride

• ChemBase ID: 179424
• Molecular Formular: C7H14ClNO4
• Molecular Mass: 211.64336
• Monoisotopic Mass: 211.06113561
• SMILES: [C@H]1([C@H]([C@H](C=C([C@H]1O)CO)N)O)O.Cl
• Canonical SMILES: OCC1=C[C@H](N)[C@@H]([C@H]([C@@H]1O)O)O.Cl
• InChI: InChI=1S/C7H13NO4.ClH/c8-4-1-3(2-9)5(10)7(12)6(4)11;/h1,4-7,9-12H,2,8H2;1H/t4-,5+,6-,7-;/m0./s1
• InChIKey: OXAPXAQYNZNSCY-JIAUUHBNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,6S)-6-amino-4-(hydroxymethyl)cyclohex-4-ene-1,2,3-triol hydrochloride
• IUPAC Traditional name: valienamine hydrochloride
• Synonyms: (1S,2S,3R,6S)-6-Amino-4-(hydroxymethyl)-4-cyclopexene-1,2,3-triol Hydrochloride; Valienamine Hydrochloride; (+)-Valienamine Hydrochloride

Database IDs

• CAS Number: 38231-86-6
• PubChem SID: 164235334
• PubChem CID: 46783223

CALCULATED PROPERTIES

• Acid pKa: 12.832338
• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): -5.7419662
• LogD (pH = 7.4): -4.090651
• Log P: -3.1384158
• Molar Refractivity: 41.8828 cm^3
• Polarizability: 16.75509 Å^3
• Polar Surface Area: 106.94 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Slightly Yellow Solid

Safety Information

• Storage Condition: Hygroscopic, Store under Inert atmosphere Refrigerator

DETAILS

Toronto Research Chemicals - V094000

A glucosidase inhibitor which does not anomerise and undergo hydrolysis.

REFERENCES

• Takeuchi, M., et al.: J. Biochem., 100, 1049 (1986)
• Asano, N., et al.: J. Antibiot., 42, 585 (1986)
• Kapferer, P., et al.: Helv. Chim. Acta, 82, 645 (1986)
• Maeda, A., et al.: Biochem. Eng. J., 8, 217 (1986)
• Maeda, A., et al.: J. Biosci. Bioeng., 95, 60