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.
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.