269741-97-1
Chemical Structure
Avrainvillamide
Synonym(s): (+)-Avrainvillamide; CJ-17,665
- CAS No.: 269741-97-1
- Formula:C26H27N3O4
- Molecular Weight:445.51
IUPAC Name: (7aS,13aS)-3,3,14,14-tetramethyl-8,16-dioxo-3,11,12,13,13a,14-hexahydro-8H,10H-7a,12a-(epiminomethano)indolizino[6,7-h]pyrano[3,2-a]carbazole 15-oxide
InChIKey: ALXLLOQTGLPCFG-XLXODUMSSA-N
SMILES: O=C1[C@]23[C@@](C(C)(C4=[N+]([O-])C5=C6C(OC(C)(C=C6)C)=CC=C5C4=C3)C)([H])CC7(C(N2)=O)N1CCC7
Biological Activity: Avrainvillamide ((+)-Avrainvillamide) is a naturally occurring alkaloid with antiproliferative effects, binds to the nuclear chaperone nucleophosmin, a proposed oncogenic protein that is overexpressed in many different human tumors. Avrainvillamide affects cell biology both by directly binding NPM1 and Crm1 as well as by inhibiting the association of these proteins with certain native cellular partners. Avrainvillamide, an antibiotic, inhibits growth of multi-agent resistant Staphylococcus aureus, Streptococcus pyogenes, and Enterococcus faecalis, with MICs of 12.5, 12.5 and 25 μg/ml, respectively[1][2][3].
| Cat. No. | Product Name | Purity | Description | Pricing | |||||||||||||||||||
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Avrainvillamide | 95.08% | Avrainvillamide ((+)-Avrainvillamide) is a naturally occurring alkaloid with antiproliferative effects, binds to the nuclear chaperone nucleophosmin, a proposed oncogenic protein that is overexpressed in many different human tumors. Avrainvillamide affects cell biology both by directly binding NPM1 and Crm1 as well as by inhibiting the association of these proteins with certain native cellular partners. Avrainvillamide, an antibiotic, inhibits growth of multi-agent resistant Staphylococcus aureus, Streptococcus pyogenes, and Enterococcus faecalis, with MICs of 12.5, 12.5 and 25 μg/ml, respectively. | ||||||||||||||||||||
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- [1]. Wulff JE, et al. The natural product avrainvillamide binds to the oncoprotein nucleophosmin. J Am Chem Soc. 2007;129(46):14444-14451. [Content Brief]
- [2]. Mukherjee H, et al. Interactions of the natural product (+)-avrainvillamide with nucleophosmin and exportin-1 Mediate the cellular localization of nucleophosmin and its AML-associated mutants. ACS Chem Biol. 2015;10(3):855-863. [Content Brief]
- [3]. Sugie Y, et al. A new antibiotic CJ-17,665 from Aspergillus ochraceus. J Antibiot (Tokyo). 2001;54(11):911-916. [Content Brief]
Keywords
