(2R,4S,5S)-2-[(6-aminohexyl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 160160
• Molecular Formular: C12H25NO6
• Molecular Mass: 279.33
• Monoisotopic Mass: 279.16818753
• SMILES: [C@@H]1([C@@H](C([C@@H](OC1CO)OCCCCCCN)O)O)O
• Canonical SMILES: NCCCCCCO[C@@H]1OC(CO)[C@H]([C@@H](C1O)O)O
• InChI: InChI=1S/C12H25NO6/c13-5-3-1-2-4-6-18-12-11(17)10(16)9(15)8(7-14)19-12/h8-12,14-17H,1-7,13H2/t8?,9-,10+,11?,12-/m1/s1
• InChIKey: GWNKFVGAEZHVTM-RXUZKVILSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S,5S)-2-[(6-aminohexyl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,4S,5S)-2-[(6-aminohexyl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: 6-Aminohexyl β-D-Glucopyranoside

Database IDs

• CAS Number: 56981-41-0
• PubChem SID: 162254295
• PubChem CID: 71313260

CALCULATED PROPERTIES

• Acid pKa: 12.214815
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -4.6439233
• LogD (pH = 7.4): -4.224105
• Log P: -1.6199368
• Molar Refractivity: 67.3364 cm^3
• Polarizability: 27.613327 Å^3
• Polar Surface Area: 125.4 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A610650

An aminoalkyl glycoside used in structure-relationship studies in regards to insulin-like activity. Used as a conjugate with magnetite nanoparticles (MNPs) to produce multifunctional HepG2 cancer cell-targeting agents.

REFERENCES

• Durette, P.L. et al.: J. Med. Chem., 21, 854 (1978)
• Lai, C. et al.: Adv. Function. Mat., 20, 3948 (1978)