Filipin

Filipin III

Names
Preferred 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
Identifiers
CAS Number	480-49-9 Y
3D model ( JSmol )	Interactive image
ChemSpider	21106312 Y
ECHA InfoCard	100.164.904
KEGG	D04186 Y
MeSH	Filipin
PubChem CID	6433194
UNII	87Z59R7D14 Y
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 Y Key: IMQSIXYSKPIGPD-NKYUYKLDSA-N Y InChI=1/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 Key: IMQSIXYSKPIGPD-NKYUYKLDBD
SMILES CCCCC[C@H](O)[C@H]1C(=O)O[C@H](C)[C@@H](O)\C=C\C=C\C=C\C=C\C=C(/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@@H]1O
Properties
Chemical formula	C35H58O11
Molar mass	654.838 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Filipin is a mixture of chemical compounds first isolated by chemists at the

It is also used in cellular biology as an inhibitor of the raft/caveolae endocytosis pathway on mammalian cells (at concentrations around 3 µg/mL)^[citation needed]

Types

Filipin is a mixture of four components - filipin I (4%), II (25%), III (53%), and IV (18%) - and should be referred to as the filipin complex.^[2][3]

• The major component, filipin III, has the structure which was proposed by Ceder and Ryhage for the filipin complex.
• Filipin I, which has been difficult to characterize, is probably a mixture of several components each having two hydroxyl groups fewer than filipin III.
• NMR
  data indicate that Filipin II is 1'-deoxy-filipin III.
• Filipin IV is isomeric to filipin III. Their NMR spectra are nearly identical with the major difference being the splitting pattern of the proton at C2. This indicates that filipin IV is probably epimeric to filipin III at either C1' or C3.

The relative and absolute stereochemistry of filipin III was determined by 13C NMR acetonide analysis.^[4]

References