FILIPIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C35H58O11
Molecular Weight	654.8284
Optical Activity	UNSPECIFIED
Defined Stereocenters	11 / 11
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCC[C@@H](O)[C@@H]1[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@H](O)C(C)=C\C=C\C=C\C=C\C=C\[C@H](O)[C@@H](C)OC1=O

InChI

InChIKey=IMQSIXYSKPIGPD-IUIVKZSISA-N

InChI=1S/C35H58O11/c1-4-5-11-16-31(42)34-33(44)22-29(40)20-27(38)18-25(36)17-26(37)19-28(39)21-32(43)23(2)14-12-9-7-6-8-10-13-15-30(41)24(3)46-35(34)45/h6-10,12-15,24-34,36-44H,4-5,11,16-22H2,1-3H3/b7-6+,10-8+,12-9+,15-13+,23-14-/t24-,25+,26-,27+,28-,29+,30+,31-,32+,33+,34-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C35H58O11
Molecular Weight	654.8284
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	11 / 11
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/mesh/68005372 | https://pubs.acs.org/doi/abs/10.1021/bi00842a021 | https://www.fermentek.com/blog/filipin-iii

FILIPIN is a complex of polyene macrolides obtained from Streptomyces filipinensis. The complex consists of four components: filipin I (4%), II (25%), III (53%), and IV (18%). Filipin III alters membrane function by interfering with membrane sterols, inhibits mitochondrial respiration, and is proposed as an antifungal agent. It is widely used as a marker for detection and quantification of cholesterol in cellular membranes.

Originator

Approval Year

PubMed

Title	Date	PubMed
Regulation of Hsp27 and Hsp70 expression in human and mouse skin construct models by caveolae following exposure to the model sulfur mustard vesicant, 2-chloroethyl ethyl sulfide.	2011-06-01	21457723
Redox signaling via lipid raft clustering in homocysteine-induced injury of podocytes.	2010-04	20036696
NADPH oxidase and lipid raft-associated redox signaling are required for PCB153-induced upregulation of cell adhesion molecules in human brain endothelial cells.	2009-10-15	19632255
PrPC-related signal transduction is influenced by copper, membrane integrity and the alpha cleavage site.	2009-09	19597535
Iron causes interactions of TAK1, p21ras, and phosphatidylinositol 3-kinase in caveolae to activate IkappaB kinase in hepatic macrophages.	2007-02-23	17172471
Caspase activation is accelerated by the inhibition of arsenite-induced, membrane rafts-dependent Akt activation.	2003-03-01	12614848
Filipin prevents pathological prion protein accumulation by reducing endocytosis and inducing cellular PrP release.	2002-07-12	11994310
HM17, a new polyene antifungal antibiotic produced by a new strain of Spirillospora.	1994-11	8002474

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:54:38 GMT 2025` Edited by `admin` on `Mon Mar 31 17:54:38 GMT 2025`
Record UNII	87Z59R7D14
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

FILIPIN III

Preferred Name

English

FILIPIN

Official Name

English

filipin [INN]

Common Name

English

1',26-DIHYDROXYFILIPIN

Common Name

English

FILIPIN [USAN]

Common Name

English

U-5956

Code

English

Oxacyclooctacosa-17,19,21,23,25-pentaen-2-one, 4,6,8,10,12,14,16,27-octahydroxy-3-(1-hydroxyhexyl)-17,28-dimethyl-

Systematic Name

English

15-DEOXYLAGOSIN

Common Name

English

NSC-3364

Code

English

FILIPIN III [MI]

Common Name

English

1'-EPI-FILIPIN IV

Common Name

English

FILIMARISIN

Common Name

English

NSC-38092

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C261