(17Z,19Z,21Z,23Z,25Z)-4,6,8,10,12,14,16,27-octahydroxy-3-(1-hydroxyhexyl)-17,28-dimethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one

• ChemBase ID: 134359
• Molecular Formular: C35H58O11
• Molecular Mass: 654.82842
• Monoisotopic Mass: 654.39791268
• SMILES: CCCCCC(C1C(CC(CC(CC(CC(CC(CC(/C(=C\C=C/C=C\C=C/C=C\C(C(OC1=O)C)O)/C)O)O)O)O)O)O)O)O
• Canonical SMILES: CCCCCC(C1C(O)CC(O)CC(O)CC(O)CC(O)CC(O)CC(O)/C(=C\C=C/C=C\C=C/C=C\C(C(OC1=O)C)O)/C)O
• 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-
• InChIKey: IMQSIXYSKPIGPD-NJZBBQJYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (17Z,19Z,21Z,23Z,25Z)-4,6,8,10,12,14,16,27-octahydroxy-3-(1-hydroxyhexyl)-17,28-dimethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one
• IUPAC Traditional name: (17Z,19Z,21Z,23Z,25Z)-4,6,8,10,12,14,16,27-octahydroxy-3-(1-hydroxyhexyl)-17,28-dimethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one
• Synonyms: Filipin III from Streptomyces filipinensis

Database IDs

• CAS Number: 480-49-9
• MDL Number: MFCD00466923
• PubChem SID: 24894871; 162228635
• PubChem CID: 71308794

CALCULATED PROPERTIES

• Acid pKa: 13.562741
• H Acceptors: 10
• H Donor: 9
• LogD (pH = 5.5): 0.009002194
• LogD (pH = 7.4): 0.0090018995
• Log P: 0.009002198
• Molar Refractivity: 181.8343 cm^3
• Polarizability: 69.64863 Å^3
• Polar Surface Area: 208.37 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: RN9800000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥85% (HPLC)
• Quality Level: PREMIUM

DETAILS

Sigma Aldrich - F4767

Biochem/physiol Actions
Filipin is a polyene macrolide antibiotic and antifungal. The antifungal mechanism of action may be due to altering membrane permeability and associated functions by binding to membrane sterols.4 Filipin inhibits prion protein (PrP) endocytosis and causes the release of PrP from the plasma membrane.5
Other Notes
Filipin III is the major component of 8 isomeric components in filipin.
Application
Filipin has been used in a double staining procedure as a probe for the detection of lipoproteins in polyacrylamide gel1 and immobilized on nitrocellulose membranes.2 It is also widely used to localize and quantitate unesterified cholesterol by virtue of a specific fluorescent complex.3