(2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)-1-[(2S,3S,4R,5R,6S)-2,4,5,6,7-pentahydroxy-3-(sulfonatooxy)heptyl]thiolan-1-ium

• ChemBase ID: 172139
• Molecular Formular: C12H24O12S2
• Molecular Mass: 424.44176
• Monoisotopic Mass: 424.07091821
• SMILES: [C@@H]1([C@@H]([C@H]([S@@+](C1)C[C@H]([C@H]([C@H](O)[C@@H]([C@@H](O)CO)O)OS(=O)(=O)[O-])O)CO)O)O
• Canonical SMILES: OC[C@@H]([C@H]([C@H]([C@@H]([C@@H](C[S@@+]1C[C@H]([C@@H]([C@H]1CO)O)O)O)OS(=O)(=O)[O-])O)O)O
• InChI: InChI=1S/C12H24O12S2/c13-1-5(15)10(19)11(20)12(24-26(21,22)23)7(17)4-25-3-6(16)9(18)8(25)2-14/h5-20H,1-4H2/t5-,6+,7+,8+,9-,10+,11+,12+,25-/m0/s1
• InChIKey: OMKXVFDVAGCPBS-QTIKZJLFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)-1-[(2S,3S,4R,5R,6S)-2,4,5,6,7-pentahydroxy-3-(sulfonatooxy)heptyl]thiolan-1-ium
• IUPAC Traditional name: (1S,2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)-1-[(2S,3S,4R,5R,6S)-2,4,5,6,7-pentahydroxy-3-(sulfonatooxy)heptyl]thiolan-1-ium
• Synonyms: Kotalanol; 1,4-Dideoxy-1,4-[(S)-[7-deoxy-5-O-sulfo-D-glycero-D-galacto-heptitol-7-yl]episulfoniumylidene]-D-arabinitol Inner Salt

Database IDs

• CAS Number: 214491-07-3
• PubChem SID: 164228049
• PubChem CID: 42632210

CALCULATED PROPERTIES

• Acid pKa: -1.7846687
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -9.222177
• LogD (pH = 7.4): -9.222188
• Log P: -8.538528
• Molar Refractivity: 83.9335 cm^3
• Polarizability: 36.28296 Å^3
• Polar Surface Area: 228.27 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - K655700

Kotalanol is a potent natural α-glucosidase inhibitor. Kotalanol is an adiabetic agent isolated from the roots and stems of Salacia reticulata Wight. Kotalanol was found to show more potent inhibitory activity against sucrase than Salacinol (S085200) and

REFERENCES

• Yoshikawa, M. et al.: Chem. Pharmac. Bull., 46, 1339 (1998)
• Matsuda, H. et al.: Pure Appl. Chem., 74, 1301 (1998)
• Mohan, S. et al.: Nat. Prod. Rep., 27, 481 (1998)