(3S,4S,6S)-2-(hydroxymethyl)-6-(octyloxy)oxane-3,4,5-triol

• ChemBase ID: 175639
• Molecular Formular: C14H28O6
• Molecular Mass: 292.36852
• Monoisotopic Mass: 292.18858862
• SMILES: [C@@H]1([C@@H](C([C@H](OC1CO)OCCCCCCCC)O)O)O
• Canonical SMILES: CCCCCCCCO[C@H]1OC(CO)[C@H]([C@@H](C1O)O)O
• InChI: InChI=1S/C14H28O6/c1-2-3-4-5-6-7-8-19-14-13(18)12(17)11(16)10(9-15)20-14/h10-18H,2-9H2,1H3/t10?,11-,12+,13?,14+/m1/s1
• InChIKey: HEGSGKPQLMEBJL-ISDWTXNASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4S,6S)-2-(hydroxymethyl)-6-(octyloxy)oxane-3,4,5-triol
• IUPAC Traditional name: (3S,4S,6S)-2-(hydroxymethyl)-6-(octyloxy)oxane-3,4,5-triol
• Synonyms: n-Octyl α-D-glucopyranoside; α-1-n-Octyl-D-glucopyranoside; Octyl α-D-Glucopyranoside

Database IDs

• CAS Number: 29781-80-4
• PubChem SID: 164231549
• PubChem CID: 46782619

CALCULATED PROPERTIES

• Acid pKa: 12.210987
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 0.8127609
• LogD (pH = 7.4): 0.8127543
• Log P: 0.81276095
• Molar Refractivity: 72.9522 cm^3
• Polarizability: 29.735554 Å^3
• Polar Surface Area: 99.38 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Powder
• Melting Point: 110-112°C

DETAILS

Toronto Research Chemicals - O285000

Angiotensin converting enzyme (ACE) inhibitor

REFERENCES

• Meezan, E., et al.: Cell. Mol. Biol., 43, 1235 (1997)
• Deng, F., et al.: Pest. Biochem. Physiol., 74, 102 (1997)
• Lohith, K., et al.: Eur. J. Med. Chem., 41, 1059 (1997)