N-(4-methyl-2-oxo-7-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-6-yl)hexadecanamide

• ChemBase ID: 169898
• Molecular Formular: C32H49NO9
• Molecular Mass: 591.73276
• Monoisotopic Mass: 591.34073215
• SMILES: c1(c(cc2c(c1)oc(=O)cc2C)NC(=O)CCCCCCCCCCCCCCC)O[C@H]1[C@H]([C@H]([C@H]([C@@H](O1)CO)O)O)O
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)Nc1cc2c(C)cc(=O)oc2cc1O[C@@H]1O[C@@H](CO)[C@@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C32H49NO9/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-27(35)33-23-18-22-21(2)17-28(36)40-24(22)19-25(23)41-32-31(39)30(38)29(37)26(20-34)42-32/h17-19,26,29-32,34,37-39H,3-16,20H2,1-2H3,(H,33,35)/t26-,29+,30+,31-,32-/m1/s1
• InChIKey: XDIAFMWEZYIYBM-XLACBCRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(4-methyl-2-oxo-7-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-6-yl)hexadecanamide
• IUPAC Traditional name: N-(4-methyl-2-oxo-7-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-6-yl)hexadecanamide
• Synonyms: N-[7-(β-D-Galactopyranosyloxy)-4-methyl-2-oxo-2H-1-benzopyran-6-yl]- hexadecanamide; HMGal; 6-Hexadecanoylamino-4-methylumbelliferyl β-D-Galactopyranoside

Database IDs

• CAS Number: 94452-17-2
• PubChem SID: 162264030
• PubChem CID: 21120485

CALCULATED PROPERTIES

• Acid pKa: 12.023937
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): 5.22876
• LogD (pH = 7.4): 5.2287498
• Log P: 5.22876
• Molar Refractivity: 159.2588 cm^3
• Polarizability: 62.419727 Å^3
• Polar Surface Area: 154.78 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H290980

A specific fluorogenic substrate of galactocerebrosidase for the diagnosis of Krabbe disease.

REFERENCES

• Wiederschain, G., et al.: Clin. Chim. Acta, 205, 87 (1992)