(2S,4S,5S)-2-{[(3R,4R)-4,5-dihydroxy-2-(hydroxymethyl)piperidin-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 169660
• Molecular Formular: C12H23NO9
• Molecular Mass: 325.31232
• Monoisotopic Mass: 325.13728132
• SMILES: [C@@H]1([C@@H](C([C@H](OC1CO)O[C@H]1[C@@H](C(CNC1CO)O)O)O)O)O
• Canonical SMILES: OCC1O[C@H](O[C@@H]2C(CO)NCC([C@H]2O)O)C([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C12H23NO9/c14-2-4-11(7(17)5(16)1-13-4)22-12-10(20)9(19)8(18)6(3-15)21-12/h4-20H,1-3H2/t4?,5?,6?,7-,8-,9+,10?,11-,12-/m1/s1
• InChIKey: GNVIYGFSOIHFHK-IJEQOOHESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5S)-2-{[(3R,4R)-4,5-dihydroxy-2-(hydroxymethyl)piperidin-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,4S,5S)-2-{[(3R,4R)-4,5-dihydroxy-2-(hydroxymethyl)piperidin-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: (2R,3R,4R,5S)-4,5-Dihydroxy-2-(hydroxymethyl)-3-piperidinyl α-D-Glucopyranoside; G1M; 4-O-α-D-Glucopyranosylmoranoline

Database IDs

• CAS Number: 80312-32-9
• PubChem SID: 162263792
• PubChem CID: 46780437

CALCULATED PROPERTIES

• Acid pKa: 12.149712
• H Acceptors: 10
• H Donor: 8
• LogD (pH = 5.5): -7.080406
• LogD (pH = 7.4): -5.347978
• Log P: -4.656579
• Molar Refractivity: 68.9877 cm^3
• Polarizability: 28.995752 Å^3
• Polar Surface Area: 172.1 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 189-192°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - G450000

An α-glucosidase inhibitor. May also prove to be an effective oral anti-diabetic agent.

REFERENCES

• Yoshikuni, Y., et al.: Chem. Pharm. Bull., 37, 106 (1989)
• Ezure, Y., et al.: Agric. Biol. Chem., 53, 61 (1989)
• Kunikata, T., et al.: Biosci., Biotechnol., Biochem., 60, 1104 (1989)