(2R,3S,4S)-1-[(2S,3S)-2,4-dihydroxy-3-(sulfonatooxy)butyl]-3,4-dihydroxy-2-(hydroxymethyl)thiolan-1-ium

• ChemBase ID: 177675
• Molecular Formular: C9H18O9S2
• Molecular Mass: 334.36382
• Monoisotopic Mass: 334.03922416
• SMILES: [C@@H]1([C@@H]([C@H]([S@@+](C1)C[C@H]([C@H](CO)OS(=O)(=O)[O-])O)CO)O)O
• Canonical SMILES: OC[C@@H]([C@@H](C[S@@+]1C[C@H]([C@@H]([C@H]1CO)O)O)O)OS(=O)(=O)[O-]
• InChI: InChI=1S/C9H18O9S2/c10-1-7(18-20(15,16)17)5(12)3-19-4-6(13)9(14)8(19)2-11/h5-14H,1-4H2/t5-,6-,7+,8-,9+,19-/m1/s1
• InChIKey: SOWRVDSZMRPKRG-YRPOCYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S)-1-[(2S,3S)-2,4-dihydroxy-3-(sulfonatooxy)butyl]-3,4-dihydroxy-2-(hydroxymethyl)thiolan-1-ium
• IUPAC Traditional name: (1S,2R,3S,4S)-1-[(2S,3S)-2,4-dihydroxy-3-(sulfonatooxy)butyl]-3,4-dihydroxy-2-(hydroxymethyl)thiolan-1-ium
• Synonyms: 1,4-Dideoxy-1,4-[(S)-[(2S,3S)-2,4-dihydroxy-3-(sulfooxy)butyl]episulfoniumylidene]-D-arabinitol Inner Salt; (1S,2R,3S,4S)-1-[(2S,3S)-2,4-Dihydroxy-3-(sulfooxy)butyl]tetrahydro-3,4-dihydroxy-2-(hydroxymethyl)thiophenium Inner Salt; Salacinol

Database IDs

• CAS Number: 200399-47-9
• PubChem SID: 164233585
• PubChem CID: 6451151

CALCULATED PROPERTIES

• Acid pKa: -1.8416387
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -7.331172
• LogD (pH = 7.4): -7.3311806
• Log P: -6.6913953
• Molar Refractivity: 66.046 cm^3
• Polarizability: 28.738945 Å^3
• Polar Surface Area: 167.58 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S085200

Salacinol is a α-glucosidase inhibitor discovered from the herb, Salacia reticulata. Salacinol is used as an antidiabetic agent.

REFERENCES

• Matsuda, H. et al.: CHem. Pharmac. Bull., 47, 1725 (1999)
• Mohan, S. et al.: Carb. Res., 342, 1551 (1999)
• Muraoka, O. et al.: J. Nat. Med., 65, 142 (1999)