Kifunensine, class I alpha-mannosidase inhibitor

Key facts

CAS number

109944-15-2

Form

Solid

form

Molecular weight

232.19 Da

Molecular formula

C₈H₁₂N₂O₆

PubChem

130611

Nature

Synthetic

Solubility

Soluble in DMSO up to 35 mg/ml

Biochemical name

Kifunensine

Biological description

Cell-permeable, potent, selective inhibitor of class I α-mannosidases. (IC₅₀ = 20-50 nM for mung bean α-1,2-mannosidase I). Alkaloid originally isolated from the actinomycete Kitasatosporia kifunense. Used to suppress Endoplasmic Reticulum-Associated Degradation (ERAD) via the inhibition of endoplasmic reticulum-associated mannosidase activity.

Canonical smiles

C(C1C(C(C(C2N1C(=O)C(=O)N2)O)O)O)O

Isomeric smiles

C([C@@H]1[C@H]([C@@H]([C@@H]([C@@H]2N1C(=O)C(=O)N2)O)O)O)O

InChi

InChI=1S/C8H12N2O6/c11-1-2-3(12)4(13)5(14)6-9-7(15)8(16)10(2)6/h2-6,11-14H,1H2,(H,9,15)/t2-,3-,4+,5+,6+/m1/s1

InChiKey

OIURYJWYVIAOCW-PQMKYFCFSA-N

IUPAC Name

(5R,6R,7S,8R,8aS)-6,7,8-trihydroxy-5-(hydroxymethyl)-1,5,6,7,8,8a-hexahydroimidazo[1,2-a]pyridine-2,3-dione