Kifunensine
Basic information
- CAS
109944-15-2- Standard SMILES
O=C1N[C@@H]2[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)N2C1=O- InChIKey
OIURYJWYVIAOCW-PQMKYFCFSA-N- Molecular formula
- C8H12N2O6
- Average molar mass
- 232.19 g/mol
- Monoisotopic mass
- 232.06953611
Overview
inhibitor of the glycoprotein processing mannosidase I; from actinomycete Kitasatosporia kifunense 9482; structure given in first source; RN given refers to (5R-(5alpha,6beta,7alpha,8alpha,8aalpha))-isomer; RN for cpd without isomeric designation not avail 10/90
Names & identifiers
- Preferred name
- Kifunensine
- IUPAC
- (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
- English name
- KIFUNENSINE
- Molecular formula
- C8H12N2O6
- Molecular weight
- 232.19
Names & synonyms
kifunensine109944-15-2FR 900494(5R,6R,7S,8R,8aS)-6,7,8-trihydroxy-5-(hydroxymethyl)-1,5,6,7,8,8a-hexahydroimidazo[1,2-a]pyridine-2,3-dioneFR-9004940NI8960271DTXSID60883199imidazo(1,2-a)pyridine-2,3-dione, hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-, (5R,6R,7S,8R,8aS)-(5R,6R,7S,8R,8aS)-6,7,8-trihydroxy-5-(hydroxymethyl)-1,5,6,7,8,8a-hexahydroimidazo(1,2-a)pyridine-2,3-dioneRefChem:151233DTXCID401022752(5R,6R,7S,8R,8aS)-6,7,8-trihydroxy-5-(hydroxymethyl)-octahydroimidazolidino(1,2-a)pyridine-2,3-dione
Show more names
KifunensinKifunensine min. 99%Kifunensine - Bio-X ?[5R-(5α,6β,7α,8α,8aα)]-Kifunensine, (+)- - FR 900494KIFUNENSINE, KITASATOSPORIA KIFUNENSEKifunensine, Kitasatosporia kifunenseKifunensine, class I alpha-mannosidase inhibitor
634-573-9(+)-Kifunensine(5R,6R,7S,8R,8aS)-6,7,8-trihydroxy-5-(hydroxymethyl)hexahydroimidazo[1,2-a]pyridine-2,3-dioneImidazo(1,2-a)pyridine-2,3-dione, hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-, (5R-(5alpha,6beta,7alpha,8alpha,8aalpha))-KIF(5R,6R,7S,8R,8aS)-Hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-imidazo[1,2-a]pyridine-2,3-dioneImidazo[1,2-a]pyridine-2,3-dione,hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-, (5R,6R,7S,8R,8aS)-(+)-Kifunensine; FR 900494;
Properties
Computed structural properties
- XLogP
- -2.8
- Topological polar surface area
- 130 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 1
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 334
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 280 °C · >280°C
- Density
- 1.85 · 1.85±0.1 g/cm3(Predicted)
- storage temp.
- 20 °C · −20°C
- solubility
- 50 MM · water, double-distilled: soluble50MM
- form
- White solid
- pka
- 9.61 · 9.61±0.70(Predicted)
- color
- White
- biological source
- synthetic (organic)
- Water Solubility
- 5 mM · Soluble to 5 mM in water with sonication
- Stability
- -20 °C · Desiccate and Store at -20°C
- 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
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory InformationImidazo1,2-apyridine-2,3-dione, hexahydro-6,7,8-trihydroxy-5-(hydroxymethyl)-, (5R,6R,7S,8R,8aS)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesEye Irrit. 2 (100%)
Safety data
- wgk
- 3
- hs_code
- 2939800000
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H319
- Hazard Classifications
- Eye Irrit. 2
- Precautionary statements
- P264-P280-P305+P351+P338-P337+P313
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationCompounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Applications
DescriptionHistorically isolated from Kitasatosporia kifunense.1Kifunensine (CAS 109944-15-2) is an inhibitor of class I α-mannosidases which inhibit glycoprotein processing. Inhibits human endoplasmic reticulum α-1,2-mannosidase I and Golgi Class I mannosidases IA, IB and IC with Ki values of 130 and 23 nM respectively.2 Inhibition of endoplasmic reticulum a-mannosidase I activity rescues the human a-sarcoglycan R77C mutation suggesting a new pharmacological approach for limb girdle muscular dystrophy type 2D patients carrying mutations that impair a-sarcoglycan trafficking.3 Improves maturation of misfolded proteins.4
UsesKifunensine 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.Ph
General DescriptionA potent alkaloid inhibitor of mannosidase I. Does not affect mannosidase II and the endoplasmic reticulum α-mannosidase.
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