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

• ChemBase ID: 179553
• Molecular Formular: C10H21NO7
• Molecular Mass: 267.27624
• Monoisotopic Mass: 267.13180202
• SMILES: [C@@H]1([C@@H](C([C@H](CC1(CO)O)NC(CO)CO)O)O)O
• Canonical SMILES: OCC(N[C@H]1CC(O)(CO)[C@H]([C@@H](C1O)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-PYLAIRLGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,5S)-5-[(1,3-dihydroxypropan-2-yl)amino]-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol
• IUPAC Traditional name: (2S,3R,5S)-5-[(1,3-dihydroxypropan-2-yl)amino]-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol
• Synonyms: 3,4-Dideoxy-4-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-2-C-(hydroxymethyl)-D-epiinositol; N-(1,3-Dihydroxy-2-propyl)valiolamine; A 71100; AO 128; Basen; Glustat; Voglibose

Database IDs

• CAS Number: 83480-29-9
• PubChem SID: 164235463
• PubChem CID: 45357542

CALCULATED PROPERTIES

• 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
• Acid pKa: 12.455839

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White to Off-White Solid
• Melting Point: 162-163°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - V750000

An α-Glucosidase inhibitor used as an antidiabetic.

REFERENCES

• Matsuo, T., et al.: Am. J. Clin. Nutr., 55, 314S (1992)
• Goke, B., et al.: Digestion, 56, 493 (1992)
• Shinozaki, K., et al.: Metabolism, 45, 731 (1996)