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

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
HM17, a new polyene antifungal antibiotic produced by a new strain of Spirillospora.	1994 Nov	8002474
Caspase activation is accelerated by the inhibition of arsenite-induced, membrane rafts-dependent Akt activation.	2003 Mar 1	12614848
PrPC-related signal transduction is influenced by copper, membrane integrity and the alpha cleavage site.	2009 Sep	19597535
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:20:37 UTC 2023` Edited by `admin` on `Fri Dec 15 15:20:37 UTC 2023`
Record UNII	87Z59R7D14
Record Status	`Validated (UNII)`
Record Version

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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