CAS 480-49-9

Filipin III

Description:

Filipin III is a polyene macrolide antibiotic that is primarily derived from the fermentation of the bacterium Streptomyces filipinensis. It is characterized by its complex structure, which includes multiple conjugated double bonds, contributing to its unique biological activity. Filipin III exhibits strong antifungal properties, particularly against various species of fungi, including Candida and Aspergillus. The compound functions by binding to sterols, particularly cholesterol, in cell membranes, leading to increased membrane permeability and ultimately cell death. Its molecular formula reflects a specific arrangement of carbon, hydrogen, and oxygen atoms, which is crucial for its biological function. Filipin III is also used as a research tool in cell biology to study membrane dynamics and lipid interactions. Due to its potent biological activity, it is important to handle Filipin III with care in laboratory settings, as it can pose risks to human health and the environment. Overall, Filipin III is a significant compound in both medicinal chemistry and microbiological research.

Formula: C₃₅H₅₈O₁₁

InChI: 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

InChI key: InChIKey=IMQSIXYSKPIGPD-YQRUMEKGSA-N

SMILES: [C@H](CCCCC)(O)[C@@]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)[H]

Synonyms:

• (17E,19E,21E,23E,25E)-4,6,8,10,12,14,16,27-octahydroxy-3-(1-hydroxyhexyl)-17,28-dimethyloxacyclooctacosa-17,19,21,23,25-pentaen-2-one
• (17Z,19E,21E,23E,25E)-4,6,8,10,12,14,16,27-octahydroxy-3-(1-hydroxyhexyl)-17,28-dimethyloxacyclooctacosa-17,19,21,23,25-pentaen-2-one
• (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-dimethyloxacyclooctacosa-17,19,21,23,25-pentaen-2-one
• 14-Deoxylagosin
• 15-Deoxylagosin
• 1′,26-Dihydroxyfilipin I
• 1′-Hydroxyfilipin II
• 1′-epi-Filipin IV
• 4,6,8,10,12,14,16,27-Octahydroxy-3-(1-Hydroxyhexyl)-17,28-Dimethyloxacyclooctacosa-17,19,21,23,25-Pentaen-2-One
• Filimarisin
• Filipin III
• Filipin Iii From Streptomyces*Filipinensis
• NSC 3364
• NSC 38092
• Oxacyclooctacosa-17,19,21,23,25-pentaen-2-one, 4,6,8,10,12,14,16,27-octahydroxy-3-[(1R)-1-hydroxyhexyl]-17,28-dimethyl-, (3R,4S,6S,8S,10R,12R,14R,16S,17E,19E,21E,23E,25E,27S,28R)-
• Oxacyclooctacosane, filipin III deriv.
• [3R-[3R*(R*),4S*,6S*,8S*,10R*,12R*,14R*,16S*,17E,19E,21E,23E,25E,27S*,28R*]]-4,6,8,10,12,14,16,27-Octahydroxy-3-(1-hydroxyhexyl)-17,28-dimethyloxacyclooctacosa-17,19,21,23,25-pentaen-2-one

Filipin III from Streptomyces filipinensis

CAS: 480-49-9

Formula: C₃₅H₅₈O₁₁

Purity: 95%

Color and Shape: Solid

Molecular weight: 654.8284

Ref: IN-DA003QLD

Filipin III

CAS: 480-49-9

Formula: C₃₅H₅₈O₁₁

Purity: (HPLC) ≥ 97.0%

Color and Shape: White to yellow powder

Molecular weight: 654.83

Ref: 7W-GX3807

Filipin III

CAS: 480-49-9

Filipin III

Formula: C₃₅H₅₈O₁₁

Purity: By hplc: 97.06% (Typical Value in Batch COA)

Color and Shape: slight yellow powder

Molecular weight: 654.82841g/mol

Ref: 54-BIA4324

Filipin III

CAS: 480-49-9

Filipin III is extracted from strain KPE18H and has significant antifungal activity.

Formula: C₃₅H₅₈O₁₁

Purity: 90%

Color and Shape: Solid

Molecular weight: 654.83

Ref: TM-T11288

Filipin III

Controlled Product

CAS: 480-49-9

Applications Filipin III is a cholesterol-binding, fluorescing antibiotic. Also, it is a pentaene macrolide produced by Streptomyces filipinensis, widely used for the detection and quantitation of cholesterol in biological membranes and as a tool for the diagnosis of Niemann-Pick type C disease;Polyene antibiotic, most extensively used tool for the specific detection of fluorescently labeled 3-β-hydroxysterols.
References Payero, T. D., et al.: Microb. Cell Fact., 14, 1-14 (2015); Stanislas, T., et al.: Methods Mol. Biol., 1209, 13-29 (2014)

Formula: C₃₅H₅₈O₁₁

Color and Shape: Neat

Molecular weight: 654.83

Ref: TR-F337003

Filipin III

CAS: 480-49-9

Filipin III is a polyene macrolide antibiotic, which is extracted from Streptomyces filipinensis. Known for its unique mode of action, Filipin III interferes with cholesterol-rich membranes by binding to ergosterol and cholesterol. This interaction disrupts the membrane structure, altering membrane permeability and ultimately affecting cell viability.

Purity: Min. 95%

Ref: 3D-BF162726