Filicin

Filicin is a chemical compound that has been isolated from ferns of the genus Dryopteris. It has been isolated from the male fern (Dryopteris filix-mas).^[1] Filicin has been studied for its anthelmintic activity.^[2]

Filicin

Names
IUPAC name 2-Butanoyl-4-{{#parsoidfragment:0}}3-butanoyl-5-[(5-butanoyl-2,6-dihydroxy-3,3-dimethyl-4-oxocyclohexa-1,5-dien-1-yl)methyl]-2,4,6-trihydroxyphenyl]methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one
Other names Filixic acid BBB; Filixic acid
Identifiers
CAS Number	4482-83-1
3D model (JSmol)	Interactive image
ChEBI	CHEBI:5060
ChemSpider	170653
ECHA InfoCard	100.022.516
EC Number	224-766-2
KEGG	C10693
PubChem CID	197044
UNII	3OQ8CMM2OZ
CompTox Dashboard (EPA)	DTXSID001101435
InChI InChI=1S/C36H44O12/c1-8-11-20(37)23-27(41)16(14-18-29(43)24(21(38)12-9-2)33(47)35(4,5)31(18)45)26(40)17(28(23)42)15-19-30(44)25(22(39)13-10-3)34(48)36(6,7)32(19)46/h40-46H,8-15H2,1-7H3 Key: FRTCWDLFHSMTNW-UHFFFAOYSA-N
SMILES CCCC(=O)C1=C(C(=C(C(=C1O)CC2=C(C(C(=O)C(=C2O)C(=O)CCC)(C)C)O)O)CC3=C(C(C(=O)C(=C3O)C(=O)CCC)(C)C)O)O
Properties
Chemical formula	C36H44O12
Molar mass	668.736 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

Related compounds

A variety of chemically related compounds, sometimes referred to collectively as filicins, have also been isolated from ferns. Chemical analysis of filicins in fern extracts can assist in determining taxonomy.^[3] Examples of filicins include:

Name(s)	Chemical structure	Molecular formula	Molecular weight (g/mol)	CAS number	PubChem	Notes and references
Filixic acid ABA		C32H36O12	612.63	38226-84-5	CID 15081408 from PubChem	First isolated from Dryopteris dickinsii[4]
Filixic acid ABP		C33H38O12	626.66	57765-54-5	CID 73672225 from PubChem	[5]
Filixic acid ABB		C34H40O12	640.68	37318-24-4	CID 102574620 from PubChem	Found in Dryopteris sieboldii[6]
Filixic acid PBP		C34H40O12	640.68	51005-85-7	CID 20055092 from PubChem	Found in Dryopteris sieboldii[6] and Dryopteris filix-mas
Filixic acid PBB		C35H42O12	654.71	49582-09-4	CID 20055091 from PubChem	[5]
Flavaspidic acid BB; Toxifren; Polystichocitrin; Glavaspidic acid		C24H30O8	446.49	114-42-1	CID 8237 from PubChem	Isolated from Dryopteris abbreviata[7]