Kifunensine - CAS 109944-15-2

Name: Kifunensine
Brand: BOC Sciences
Rating: 5 (1 reviews)

Catalog:	BB002564
Product Name:	Kifunensine
CAS:	109944-15-2
Synonyms:	[5R-(5α,6β,7α,8α,8aα)]-Hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-imidazo[1,2-a]pyridine-2,3-dione; (+)-Kifunensine; FR 900494; (5R,6R,7S,8R,8aS)-6,7,8-trihydroxy-5-(hydroxymethyl)hexahydroimidazo[1,2-a]pyridine-2,3-dione; Imidazo(1,2-a)pyridine-2,3-dione, hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-, (5R-(5alpha,6beta,7alpha,8alpha,8aalpha))-

Technical Data

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
Description:	Kifunensine is an alkaloid produced by the fungus, Kitasatosporia kifunense, and has been shown to be a weak inhibitor of aryl mannosidase. It is a unique oxamide derivative of mannojirimycin and a potent inhibitor of the glycoprotein processing enzyme mannosidase I. Kifunenesine is ineffective in inhibiting either mannosidase II or the endoplasmic reticulum (ER) a-mannosidase. It also possesses immunomodulating properties based on chemical, physicochemical and x-ray crystallographic analysis. When tested in cell culture using influenza virus-infected MDCK cells, kifunensine, at 1 mg/ml or less, caused almost complete inhibition of complex chain formation with the accumulation of Man9(GlcNAc)2. Thus, kifunensine was proven to be 50 to 100 times more effective than deoxymannojirimycin.
Molecular Weight:	232.19
Molecular Formula:	C8H12N2O6
Canonical SMILES:	C(C1C(C(C(C2N1C(=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
InChI Key:	OIURYJWYVIAOCW-PQMKYFCFSA-N
Melting Point:	290-296 °C (dec.)
Purity:	≥95%
Density:	1.85±0.1 g/cm3 (Predicted)
Solubility:	Soluble in DMSO (Slightly, Heated), Methanol (Very Slightly, Heated, Sonicated), Water (Very Slightly)
Appearance:	White to Off-white Solid
Storage:	Store at -20 °C
MDL:	MFCD00270017
LogP:	-4.00520

GHS Hazard Statement:	H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
Precautionary Statement:	P264, P280, P305+P351+P338, and P337+P313
Signal Word:	Warning

Publication Number	Title	Priority Date
CN-111543476-A	Cassava preservative	20200622
WO-2021116398-A1	Glycosylated polypeptides	20191212
WO-2020186111-A2	Vista-binding antibodies and uses thereof	20190312
WO-2019243672-A1	Conjugate	20180619
US-2012027750-A1	Method and compositions for cancer prognosis	20081208

PMID	Publication Date	Title	Journal
31339623	20191001	Unfolded protein response regulates P53 expression in the pulmonary endothelium	Journal of biochemical and molecular toxicology
30140005	20180824	Fatostatin induces pro- and anti-apoptotic lipid accumulation in breast cancer	Oncogenesis
23708606	20130701	Supersite of immune vulnerability on the glycosylated face of HIV-1 envelope glycoprotein gp120	Nature structural & molecular biology
23159373	20130110	Synthesis of kifunensine thioanalogs and their inhibitory activities against HIV-RT and α-mannosidase	Carbohydrate research
22571197	20120801	TGF-β sensitivity is determined by N-linked glycosylation of the type II TGF-β receptor	The Biochemical journal

Complexity:	335
Compound Is Canonicalized:	Yes
Covalently-Bonded Unit Count:	1
Defined Atom Stereocenter Count:	5
Defined Bond Stereocenter Count:	0
Exact Mass:	232.06953611
Formal Charge:	0
Heavy Atom Count:	16
Hydrogen Bond Acceptor Count:	6
Hydrogen Bond Donor Count:	5
Isotope Atom Count:	0
Monoisotopic Mass:	232.06953611
Rotatable Bond Count:	1
Topological Polar Surface Area:	130 Å²
Undefined Atom Stereocenter Count:	0
Undefined Bond Stereocenter Count:	0
XLogP3:	-2.8