2,5-dioxopyrrolidin-1-yl 6-{[(3S,4R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxan-3-yl]oxy}hexanoate

• ChemBase ID: 174519
• Molecular Formular: C26H31NO12
• Molecular Mass: 549.52384
• Monoisotopic Mass: 549.18462544
• SMILES: [C@@H]1([C@@H](C([C@H](OC1CO)Oc1ccc2c(c1)oc(=O)cc2C)O)O)OCCCCCC(=O)ON1C(=O)CCC1=O
• Canonical SMILES: OCC1O[C@H](Oc2ccc3c(c2)oc(=O)cc3C)C([C@H]([C@@H]1OCCCCCC(=O)ON1C(=O)CCC1=O)O)O
• InChI: InChI=1S/C26H31NO12/c1-14-11-22(32)37-17-12-15(6-7-16(14)17)36-26-24(34)23(33)25(18(13-28)38-26)35-10-4-2-3-5-21(31)39-27-19(29)8-9-20(27)30/h6-7,11-12,18,23-26,28,33-34H,2-5,8-10,13H2,1H3/t18?,23-,24?,25-,26+/m1/s1
• InChIKey: RBZIGRUIFAFDSQ-GLFXSZLYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 6-{[(3S,4R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxan-3-yl]oxy}hexanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 6-{[(3S,4R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(4-methyl-2-oxochromen-7-yl)oxy]oxan-3-yl]oxy}hexanoate
• Synonyms: 4-Methylumbelliferyl α-D-Glucopyranoside 4’-O-C6-NHS Ester; 4-Methylumbelliferyl α-D-Glucopyranoside 4'-O-C6-N-Hydroxysuccinimide Ester

Database IDs

• PubChem SID: 164230429
• PubChem CID: 71750695

CALCULATED PROPERTIES

• Acid pKa: 12.262812
• H Acceptors: 10
• H Donor: 3
• LogD (pH = 5.5): 0.4166272
• LogD (pH = 7.4): 0.41662133
• Log P: 0.4166273
• Molar Refractivity: 130.0019 cm^3
• Polarizability: 51.80623 Å^3
• Polar Surface Area: 178.36 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M334515

4-Methylumbelliferyl α-D-Glucopyranoside 4’-O-C6-N-Hydroxysuccinimide ester is a 4-Methylumbelliferyl derivative as glycosidase inhibitor for the treatment of T2DM.

REFERENCES

• Asano, N., et al.: J. Med. Chem., 37, 3701 (1994)
• Scott, L.J., et al.: Drugs, 59, 521 (1994)