Filicin

Names
IUPAC name

2-Butanoyl-4-[[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

EC Number |

* 224-766-2

KEGG |

* C10693

PubChem CID

* 197044

UNII |

* 3OQ8CMM2OZ

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

Tracking categories (test):

* SizeSet

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]

## 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

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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]

## References

1. ↑ "Filicin". TOXNET. U.S. National Library of Medicine. https://chem.nlm.nih.gov/chemidplus/rn/4482-83-1.
2. ↑ Heikinheimo, R (1963). "Effect of filicin administered as an anthelmintic on the coagulation factors of the blood". Annales Medicinae Internae Fenniae 52: 93–6. PMID 13953368.
3. ↑ Euw, J. v.; Lounasmaa, M.; Reichstein, T.; Widén, C.J. (1980). "Chemotaxonomy in Dryopteris and related fern genera". Studia Geobotanica 1: 275–311. https://www.openstarts.units.it/handle/10077/14793.
4. ↑ Hisada, Sueo; Shiraishi, Koichi; Inagaki, Isao (1972). "Pharmaceutical studies on Japanese ferns containing phloroglucinol derivatives. 9 Constituents of Dryopteris dickinsii". Yakugaku Zasshi 92 (9): 1124–1128. doi:10.1248/yakushi1947.92.9_1124.
5. ↑ 5.0 5.1 Widén, C. J; Lounasmaa, M; Sarvela, J (1975). "Phloroglucinol derivatives of eleven Dryopteris species from Japan". Planta Medica 28 (2): 144–64. PMID 1197418.
6. ↑ 6.0 6.1 Hisada, Sueo; Inoue, O.; Inagak, Isao (1973). "Phloroglucinol derivatives of Dryopteris sieboldii". Phytochemistry 12 (8): 2055. doi:10.1016/s0031-9422(00)91535-8.
7. ↑ Coşkun, Maksut; Sakushima, Akiyo; Nishibe, Sansei; Hisada, Sueo; Tanker, Nevin (1982). "A phloroglucinol derivative of Dryopteris abbreviata". Phytochemistry 21 (6): 1453. doi:10.1016/0031-9422(82)80168-4.

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*[CID]: Compound ID