Description
Filipin III is the major component of Filipin, a 28-membered ring pentaene macrolide antifungal antibiotic produced by S. filipinensis, S. avermitilis and S. miharaensis. Filipin interacts with membrane sterols causing the alteration of membrane structure.
Synonyms
16,20,22,24-Octacosapentenoic Acid
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
Molecular Formula
C35H58O11
Canonical SMILES
CCCCC[C@H](C1[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
InChI
IMQSIXYSKPIGPD-YQRUMEKGSA-N
InChI Key
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
Solubility
Soluble in methanol (up to 10 mg/ml)
Appearance
White or light yellow solid
Storage
Powder-20°C, 3 years; 4°C, 2 years; In solvent-80°C, 6 months; -20°C, 1 month.
Source
Streptomyces miharaensis
Stability
Stable for 1 year from date of purchase as supplied. Solutions in methanol may be stored under ineRoom temperature gas at -20 °C for up to 2 months.
Storage Temperature
-20 °C
Supplemental Hazard Statements
H315-H319-H335