Filipin III

Names

[ CAS No. ]:
480-49-9

[ Name ]:
Filipin III

[Synonym ]:
Oxacyclooctacosa-17,19,21,23,25-pentaen-2-one, 4,6,8,10,12,14,16,27-octahydroxy-3-(1-hydroxyhexyl)-17,28-dimethyl-, (17E,19E,21E,23E,25E)-
(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
Filipin III

Biological Activity

[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].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Fungal

Research Areas >> Inflammation/Immunology

[Target]

Fungal[1]

[References]

[1]. Payero TD, et al. Functional analysis of filipin tailoring genes from Streptomyces filipinensis reveals alternative routes in filipin III biosynthesis and yields bioactive derivatives. Microb Cell Fact. 2015 Aug 7;14:114.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
913.9±65.0 °C at 760 mmHg

[ Melting Point ]:
163-180°C

[ Molecular Formula ]:
C₃₅H₅₈O₁₁

[ Molecular Weight ]:
654.828

[ Flash Point ]:
279.3±27.8 °C

[ Exact Mass ]:
654.397888

[ PSA ]:
208.37000

[ LogP ]:
-0.41

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.536

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RN9800000

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

CAS REGISTRY NUMBER :: 480-49-9

LAST UPDATED :: 199709

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C35-H58-O11

MOLECULAR WEIGHT :: 654.93

WISWESSER LINE NOTATION :: T-28-OV PU TU VU A&UTJ CYQ5 DQ FQ HQ JQ LQ MQ OQ P1 C&Q D&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 17 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: DNA adduct

TEST SYSTEM :: Bacteria - Escherichia coli

DOSE/DURATION :: 10 mg/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 89,95,1981

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
RN9800000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Cholesterol dependence of collagen and echovirus 1 trafficking along the novel α2β1 integrin internalization pathway.

PLoS ONE 8(2) , e55465, (2013)

We have previously shown that soluble collagen and a human pathogen, echovirus 1 (EV1) cluster α2β1 integrin on the plasma membrane and cause their internalization into cytoplasmic endosomes. Here we ...

Analysis of cholesterol trafficking with fluorescent probes.

Methods Cell Biol. 108 , 367-93, (2012)

Cholesterol plays an important role in determining the biophysical properties of biological membranes, and its concentration is tightly controlled by homeostatic processes. The intracellular transport...

Influence of membrane cholesterol in the molecular evolution and functional regulation of TRPV4.

Biochem. Biophys. Res. Commun. 456(1) , 312-9, (2015)

TRPV4 is involved in several physiological and sensory functions as well as with several diseases and genetic disorders, though the molecular mechanisms for these are unclear. In this work we have ana...