Structure via PubChem · Public domain (PubChem)
filipin III
Sign in to saveAlso known as 14-Deoxylagosin, Filimarisin, Filipin
Filipin is a mixture of chemical compounds first isolated by chemists at the Upjohn company in 1955 from the mycelium and culture filtrates of a previously unknown actinomycete, Streptomyces filipinensis. It was discovered in a soil sample collected in the Philippine Islands, hence the name filipin. The isolate possessed potent antifungal activity. It was identified as a polyene macrolide based on its characteristic UV-Vis and IR spectra.
In the Vinony graph
Within Vinony's link graph, filipin III is referenced by 10 other articles, and connects out to Philippines, infrared radiation and digital object identifier.
It is catalogued under topics including Antifungals, Chembox image size set and ECHA InfoCard ID from Wikidata.
Its subject is documented across 11 Wikipedia language editions.
Chemical data
- Formula
- C35H58O11
- Molecular weight
- 654.8 g/mol
- IUPAC name
- (3R,4S,6S,8S,10R,12R,14R,16S,17E,19E,21E,23E,25E,27S,28R)-4,6,8,10,12,14,16,27-octahydroxy-3-[(1R)-1-hydroxyhexyl]-17,28-dimethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one
- SMILES
- CCCCC[C@H]([C@@H]1[C@H](C[C@H](C[C@H](C[C@H](C[C@H](C[C@H](C[C@@H](/C(=C/C=C/C=C/C=C/C=C/[C@@H]([C@H](OC1=O)C)O)/C)O)O)O)O)O)O)O)O
- InChIKey
- IMQSIXYSKPIGPD-YQRUMEKGSA-N
- XLogP
- 3.2
- Polar surface area
- 208 Ų
- H-bond donors
- 9
- H-bond acceptors
- 11
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
1,615 papers- Methods for Visualizing and Quantifying Cholesterol Distribution in Mammalian Cells Using Filipin and D4 Probes.Methods in molecular biology (Clifton, N.J.) · 2025
- Functional analysis of filipin tailoring genes from Streptomyces filipinensis reveals alternative routes in filipin III biosynthesis and yields bioactive derivatives.Microbial cell factories · 2015
- Permeabilizing action of filipin III on model membranes through a filipin-phospholipid binding.Biochimica et biophysica acta · 1992
- Cholesterol reporter molecules.Bioscience reports · 2007
- Solution NMR structures of the polyene macrolide antibiotic filipin III.FEBS letters · 2000
via PubMed
Wikidata facts
- Mass
- 654.397913
Show 5 more facts
- chemical formula
- C₃₅H₅₈O₁₁
- canonical SMILES
- CCCCCC(C1C(CC(CC(CC(CC(CC(CC(C(=CC=CC=CC=CC=CC(C(OC1=O)C)O)C)O)O)O)O)O)O)O)O
- isomeric SMILES
- CCCCC[C@H]([C@@H]1[C@H](C[C@H](C[C@H](C[C@H](C[C@H](C[C@H](C[C@@H](/C(=C/C=C/C=C/C=C/C=C/[C@@H]([C@H](OC1=O)C)O)/C)O)O)O)O)O)O)O)O
- subject has role
- antifungal
- different from
- Filipinos
Sources (6)
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Functions
- Types
- References
- External links
Filipin is a mixture of chemical compounds first isolated by chemists at the Upjohn company in 1955 from the mycelium and culture filtrates of a previously unknown actinomycete, Streptomyces filipinensis. It was discovered in a soil sample collected in the Philippine Islands, hence the name filipin. The isolate possessed potent antifungal activity. It was identified as a polyene macrolide based on its characteristic UV-Vis and IR spectra.
==Functions== Although the polyene macrolide antibiotics exhibit potent antifungal activity, most are too toxic for therapeutic applications, with the exceptions of amphotericin B and nystatin A1. Unlike amphotericin B and nystatin A1 which form sterol-dependent ion channels, filipin is thought to be a simple membrane disrupter. Since filipin is highly fluorescent and binds specifically to cholesterol, it has found widespread use as a histochemical stain for cholesterol. This method of detecting cholesterol in cell membranes is used clinically in the study and diagnosis of Type C Niemann-Pick disease.
Excerpted from Wikipedia’s “filipin III” article, available under the CC BY-SA 4.0 licence.