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

[H][C@@]1([C@H](O)CCCCC)[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

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
HM17, a new polyene antifungal antibiotic produced by a new strain of Spirillospora.	1994 Nov	8002474
NADPH oxidase and lipid raft-associated redox signaling are required for PCB153-induced upregulation of cell adhesion molecules in human brain endothelial cells.	2009 Oct 15	19632255
Redox signaling via lipid raft clustering in homocysteine-induced injury of podocytes.	2010 Apr	20036696
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 Jun 1	21457723

Patents

Name

Type

Language

FILIPIN

Official Name

English

filipin [INN]

Common Name

English

FILIPIN III

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