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Filipin III

Filipin III structure

CAS No:
480-49-9
Formula:
C35H58O11
Chemical Name:
Filipin III
Synonyms:
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)-;Filipin;Filipin III;Oxacyclooctacosane,filipin III deriv.;(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;Filimarisin;[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;15-Deoxylagosin;NSC 3364;NSC 38092;1′,26-Dihydroxyfilipin I;1′-Hydroxyfilipin II;1′-epi-Filipin IV;10109-08-7;11006-21-6;27115-88-4;875829-47-3
Categories:
Organic Chemistry > Heterocyclic Ring

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[1].

A complex of polyene antibiotics obtained from Streptomyces filipinensis. Filipin III alters membrane function by interfering with membrane sterols, inhibits mitochondrial respiration, and is proposed as an antifungal agent. Filipins I, II, and IV are less important.

Filipin III Basic Attributes

Molecular Weight：

654.828

Exact Mass：

654.83

Characteristics

PSA：

208.37000

XLogP3：

-0.41

Density：

1.2±0.1 g/cm3

Melting Point：

163-180 °C

Boiling Point：

913.9±65.0 °C at 760 mmHg

Flash Point：

279.3±27.8 °C

Refractive Index：

1.536

Storage Conditions：

-20ºC

Vapor Pressure：

0mmHg at 25°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R36/37/38

safety instructions：

26-36

RTECS Number：

RN9800000

Marks：

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H315-H319-H335

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)|Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)|Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)

MeSH Entry Terms：

Desoxylagosin

Filipin III Use and Manufacturing

Filipin III is the major component of the filipin complex, a family of pentaene antifungal metabolites first isolated from Streptomyces filipinensis and reported by researchers at Upjohn in 1955. Filipin III is a potent broad spectrum antifungal agent that also exhibits antitumor and antiviral activities. Filipin III acts by binding cell membrane sterols, disrupting membrane integrity. This sterol selectivity has led to the use of filipin III as a routine diagnostic probe for quantifying cholesterol in mammalian cells. Cholesterol is both an important structural component of cell membranes and an early intermediate in hormone and bile acid biosynthesis. The localization and measurement of cholesterol in cells is therefore of great interest. Filipin is the collective name given to four isomeric polyene macrolides isolated from cultures of S. filipinensis; Filipin III is the predominant isomer and the one used in most studies. Filipin binds to cholesterol in membranes, forming ultrastructural aggregates and complexes which can be visualized by freeze-fracture electron microscopy. The binding of cholesterol also decreases the intrinsic fluorescence of Filipin, and this property has also been used to detect cholesterol in membrane fractions.[Cayman Chemical] Produces arthritis rapidly in rabbits: Pras, Weissman, Drug Trade News, July 4, 1966, p 40; as a sterol probe in freeze-fracture cytochemistry.

Computed Properties

Molecular Weight:654.8
XLogP3:3.2
Hydrogen Bond Donor Count:9
Hydrogen Bond Acceptor Count:11
Rotatable Bond Count:5
Exact Mass:654.39791266
Monoisotopic Mass:654.39791266
Topological Polar Surface Area:208
Heavy Atom Count:46
Complexity:991
Undefined Atom Stereocenter Count:11
Undefined Bond Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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FILIPIN III

CAS No.: 480-49-9

Grade: Industrial Grade

Content: 99%

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