Kifunensine - Moligand™,≥98% , CAS No.109944-15-2

CAS: 109944-15-2 Cat. No.: K274698 Molecular Weight: 232.19 EC Number: 634-573-9

GRADE & PURITY Moligand™, ≥98%

Synonyms

FR-900494 | (5R,6R,7S,8R,8aS)-6,7,8-trihydroxy-5-(hydroxymethyl)hexahydroimidazo[1,2-a]pyridine-2,3-dione

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Kifunensine is an effective selective inhibitor of type I α-mannosidases that can be isolated from actinomycetes. It can prevent the trimming of mannose residues on glycoproteins by α-mannosidases I. Kifunensine can inhibit the endoplasmic reticulum-related protein degradation pathway.

Specifications

Synonyms

FR-900494 | (5R, 6R, 7S, 8R, 8aS)-6, 7, 8-trihydroxy-5-(hydroxymethyl)hexahydroimidazo[1, 2-a]pyridine-2, 3-dione

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Cell-permeable, potent, selective inhibitor of class I α-mannosidases. (IC 50 = 20-50 nM for\xa0mung bean α-1, 2-mannosidase I). Alkaloid originally isolated from the actinomycete Kitasatosporia kifunense . Used to suppress Endoplasmic Reticulum-Associated

Storage

Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504757004
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504757004
• Canonical Smiles: C(C1C(C(C(C2N1C(=O)C(=O)N2)O)O)O)O
• 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
• InChIKey: OIURYJWYVIAOCW-PQMKYFCFSA-N
• 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
• Isomeric SMILES: C([C@@H]1[C@H]([C@@H]([C@@H]([C@@H]2N1C(=O)C(=O)N2)O)O)O)O
• Molecular Weight: 232.19
• Reaxy-Rn: 38226983
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=38226983&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives
• Direct Parent: Alpha amino acids and derivatives
• Alternative Parents: Imidazopyridines Piperidines Imidazolidinones Tertiary carboxylic acid amides Secondary carboxylic acid amides Secondary alcohols Lactams Polyols Azacyclic compounds Primary alcohols Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Alpha-amino acid or derivatives - Imidazopyridine - Imidazolidinone - Piperidine - Imidazolidine - Tertiary carboxylic acid amide - Carboxamide group - Lactam - Secondary carboxylic acid amide - Secondary alcohol - Azacycle - Organoheterocyclic compound - Polyol - Organooxygen compound - Organonitrogen compound - Alcohol - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Carbonyl group - Organic nitrogen compound - Primary alcohol - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GH92 alpha-mannosidase (372 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water to 10 mM (with warming)
• Melt Point(°C): >208°C (dec.)
• Molecular Weight: 232.190 g/mol
• XLogP3: -2.800
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 232.07 Da
• Monoisotopic Mass: 232.07 Da
• Topological Polar Surface Area: 130.000 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 334.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Xue Zhichao, Zeng Jiaming, Yin Xinchi, Li Yongshu, Meng Bo, Zhao Yang, Fang Xiang, Gong Xiaoyun, Dai Xinhua.  (2023)  Investigation on acquired palbociclib resistance by LC-MS based multi-omics analysis.  Frontiers in Molecular Biosciences,      [PMID:36743215] [10.3389/fmolb.2023.1116398]