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

• ChemBase ID: 175638
• Molecular Formular: C26H48O16
• Molecular Mass: 616.64972
• Monoisotopic Mass: 616.29423546
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO[C@@H]1[C@H]([C@H]([C@@H]([C@@H](O1)CO)O)O)O)OCCCCCCCC)O)O[C@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)CO)O
• Canonical SMILES: CCCCCCCCO[C@@H]1O[C@@H](CO[C@H]2O[C@@H](CO)[C@H]([C@@H]([C@@H]2O)O)O)[C@H]([C@@H]([C@@H]1O)O[C@H]1O[C@@H](CO)[C@H]([C@@H]([C@@H]1O)O)O)O
• InChI: InChI=1S/C26H48O16/c1-2-3-4-5-6-7-8-37-25-22(36)23(42-26-21(35)19(33)16(30)13(10-28)40-26)17(31)14(41-25)11-38-24-20(34)18(32)15(29)12(9-27)39-24/h12-36H,2-11H2,1H3/t12-,13-,14-,15-,16-,17-,18+,19+,20+,21+,22+,23+,24+,25-,26-/m1/s1
• InChIKey: CMQKGONXPQXZKM-OMWWXRLNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5S,6R)-2-{[(2R,3R,4S,5S,6R)-3,5-dihydroxy-6-(octyloxy)-4-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,3S,4S,5S,6R)-2-{[(2R,3R,4S,5S,6R)-3,5-dihydroxy-6-(octyloxy)-4-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: Man1-α-6[Man1-α-3]Man-β-O-Octyl; n-Octyl 3,6-Di-O-(α-D-mannopyranosyl)-β-D-mannopyranoside

Database IDs

• CAS Number: 140147-36-0
• PubChem SID: 164231548
• PubChem CID: 132273

CALCULATED PROPERTIES

• Acid pKa: 11.755692
• H Acceptors: 16
• H Donor: 10
• LogD (pH = 5.5): -2.7289107
• LogD (pH = 7.4): -2.7289295
• Log P: -2.7289104
• Molar Refractivity: 137.7788 cm^3
• Polarizability: 57.28831 Å^3
• Polar Surface Area: 257.68 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 111-114°C

Safety Information

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

DETAILS

Toronto Research Chemicals - O277500

An acceptor for the assay of N-Acetylglucosaminyltransferase-1. A useful diagnostic for autosomal recessive congenital muscular dystrophies that can have associated brain and eye abnormalities.

REFERENCES

• Kaur, J., K. and Hindsgaul, O.: Glycoconjugate Journal, 8:90 (1991)
• Schachter, H., et al.: Clinical Biochemistry, 36, 339 (2003)