| Identification | Back Directory | [Name]
8H,10H-7a,12a-(Iminomethano)indolizino[6,7-h]pyrano[3,2-a]carbazole-8,16-dione, 3,11,12,13,13a,14-hexahydro-3,3,14,14-tetramethyl-, 15-oxide, (7aS,12aS,13aS)- | [CAS]
269741-97-1 | [Synonyms]
Avrainvillamide
8H,10H-7a,12a-(Iminomethano)indolizino[6,7-h]pyrano[3,2-a]carbazole-8,16-dione, 3,11,12,13,13a,14-hexahydro-3,3,14,14-tetramethyl-, 15-oxide, (7aS,12aS,13aS)- | [Molecular Formula]
C26H27N3O4 | [MDL Number]
MFCD30475728 | [MOL File]
269741-97-1.mol | [Molecular Weight]
445.51 |
| Chemical Properties | Back Directory | [density ]
1.42±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
DMSO: soluble; Methanol: soluble | [form ]
A solid | [pka]
11.03±0.60(Predicted) | [color ]
White to off-white |
| Hazard Information | Back Directory | [Uses]
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]. | [Biological Activity]
Avrainvillamide is a fungal metabolite and monomeric form of stephacidin B that has been found in A. ochraceus.1,2 It is active against S. aureus, S. pyogenes, and E. faecalis (MICs = 12.5, 12.5, and 25 μg/ml, respectively).2 Avrainvillamide inhibits the growth of LNCaP, BT-549, T47D, and MALME-3M cancer cells with GI50 values of 0.24, 0.62, 0.21, and 0.41 μM, respectively.1 | [References]
1.Wulff, J.E., Herzon, S.B., Siegrist, R., et al.Evidence for the rapid conversion of stephacidin B into the electrophilic monomer avrainvillamide in cell cultureJ. Am. Chem. Soc.129(16)4898-4899(2007)
2.Sugie, Y., Hirai, H., Inagaki, T., et al.A new antibiotic CJ-17,665 from Aspergillus ochraceusJ. Antibiot.54(11)911-916(2001)
|
|
| Company Name: |
BOC Sciences
|
| Tel: |
1-631-485-4226; 16314854226 |
| Website: |
https://www.bocsci.com |
| Company Name: |
ChemeGen
|
| Tel: |
18818260767 |
| Website: |
https://www.chemegen.com |
|