Aflavinine

Aflavinine is an anti-insectan chemical compound produced by some plants and fungi.[1][2][3]

Aflavinine

Names
IUPAC name (1S,4R,4aS,7R,7aS,11aS)-8-(1H-Indol-3-yl)-4,4a,7-trimethyl-9-propan-2-yl-1,2,3,4,5,6,7,7a,10,11-decahydrobenzo[i]naphthalen-1-ol
Identifiers
CAS Number	74328-59-9
3D model (JSmol)	Interactive image
ChemSpider	10313765
PubChem CID	21725958
UNII	42N1443TXV
CompTox Dashboard (EPA)	DTXSID40995845
InChI InChI=1S/C28H39NO/c1-17(2)20-13-15-28-24(30)11-10-19(4)27(28,5)14-12-18(3)26(28)25(20)22-16-29-23-9-7-6-8-21(22)23/h6-9,16-19,24,26,29-30H,10-15H2,1-5H3/t18-,19-,24+,26+,27+,28+/m1/s1 Key: LXZADDNPPHIYMD-QQVIWQHHSA-N
SMILES CC1CCC2(C(CCC(C23C1C(=C(CC3)C(C)C)C4=CNC5=CC=CC=C54)O)C)C
Properties
Chemical formula	C28H39NO
Molar mass	405.626 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References

1. Gallagher, Rex T.; McCabe, Terrence; Hirotsu, Ken; Clardy, Jon; Nicholson, Judith; Wilson, Benjamin J. (January 1980). "Aflavinine, a novel indole-mevalonate metabolite from tremorgen-producing species". Tetrahedron Letters. 21 (3): 243–246. doi:10.1016/s0040-4039(00)71179-8. ISSN 0040-4039.
2. Gloer, James B.; TePaske, Mark R.; Sima, John S.; Wicklow, Donald T.; Dowd, Patrick F. (November 1988). "Antiinsectan aflavinine derivatives from the sclerotia of Aspergillus flavus". The Journal of Organic Chemistry. 53 (23): 5457–5460. doi:10.1021/jo00258a011. ISSN 0022-3263.
3. Wang, H. J.; Gloer, J. B.; Wicklow, D. T.; Dowd, P. F. (Dec 1995). "Aflavinines and other antiinsectan metabolites from the ascostromata of Eupenicillium crustaceum and related species". Applied and Environmental Microbiology. 61 (12): 4429–4435. ISSN 0099-2240. PMC 167750. PMID 8534106.