(1R,2R,3R,4S,5S)-4-amino-5-(methylsulfanyl)cyclopentane-1,2,3-triol

• ChemBase ID: 172542
• Molecular Formular: C6H13NO3S
• Molecular Mass: 179.23732
• Monoisotopic Mass: 179.06161428
• SMILES: [C@@H]1([C@H]([C@H]([C@H]([C@H]1O)N)SC)O)O
• Canonical SMILES: CS[C@@H]1[C@H](O)[C@@H]([C@@H]([C@@H]1N)O)O
• InChI: InChI=1S/C6H13NO3S/c1-11-6-2(7)3(8)4(9)5(6)10/h2-6,8-10H,7H2,1H3/t2-,3+,4+,5+,6-/m0/s1
• InChIKey: BLOFGONIVNXZME-BSQWINAVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,3R,4S,5S)-4-amino-5-(methylsulfanyl)cyclopentane-1,2,3-triol
• IUPAC Traditional name: (1R,2R,3R,4S,5S)-4-amino-5-(methylsulfanyl)cyclopentane-1,2,3-triol
• Synonyms: Mannostatin A, Hydrochloride

Database IDs

• CAS Number: 134235-13-5
• PubChem SID: 164228452
• PubChem CID: 29982865

CALCULATED PROPERTIES

• Acid pKa: 12.879387
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -4.7638383
• LogD (pH = 7.4): -3.3286588
• Log P: -1.9162604
• Molar Refractivity: 42.331 cm^3
• Polarizability: 17.56837 Å^3
• Polar Surface Area: 86.71 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off White Foam

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Moisture sensitive

DETAILS

Toronto Research Chemicals - M166500

A potent glycosidase inhibitor that blocks Golgi processing mannosidase ll more effectively than swainsonine.

REFERENCES

• Tropea, J.E., et al.: Biochemistry, 29, 10062 (1990)