(1S,2S,3R,4S)-5-[(1,3-dihydroxypropan-2-yl)amino]-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol

• ChemBase ID: 179722
• Molecular Formular: C10H21NO7
• Molecular Mass: 267.27624
• Monoisotopic Mass: 267.13180202
• SMILES: [C@]1([C@H]([C@@H]([C@H](C(C1)NC(CO)CO)O)O)O)(O)CO
• Canonical SMILES: OCC(NC1C[C@](O)(CO)[C@H]([C@@H]([C@H]1O)O)O)CO
• InChI: InChI=1S/C10H21NO7/c12-2-5(3-13)11-6-1-10(18,4-14)9(17)8(16)7(6)15/h5-9,11-18H,1-4H2/t6?,7-,8+,9-,10-/m0/s1
• InChIKey: FZNCGRZWXLXZSZ-NSRVDLHZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S)-5-[(1,3-dihydroxypropan-2-yl)amino]-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol
• IUPAC Traditional name: (1S,2S,3R,4S)-5-[(1,3-dihydroxypropan-2-yl)amino]-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol
• Synonyms: Basen; Voglibose

Database IDs

• CAS Number: 83480-29-9
• PubChem SID: 164235632
• PubChem CID: 16760222

CALCULATED PROPERTIES

• Acid pKa: 12.455839
• H Acceptors: 8
• H Donor: 8
• LogD (pH = 5.5): -6.9796877
• LogD (pH = 7.4): -5.301458
• Log P: -4.8527865
• Molar Refractivity: 59.5467 cm^3
• Polarizability: 24.53386 Å^3
• Polar Surface Area: 153.64 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Potent alpha-glucosidase inhibitor

Product Information

• Biological Source: Produced by Streptomyces hygroscopicus-limoneus
• Application(s): Oral antidiabetic agent

REFERENCES

• Eur. Pat., 1982, Takeda, 56 194; CA, 97, 198515r, (synth, pharmacol)
• Horii, S. et al., J. Med. Chem., 1986, 29, 1038, (synth)
• Odaka, H. et al., J. Nutr. Sci. Vitaminol., 1992, 38, 27, (pharmacol)
• Fukase, H. et al., J.O.C., 1992, 57, 3651, (synth, pmr)