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219557

Cerulenin

Name: Cerulenin
Brand: MM

from Cephalosporium caerulens, ≥98% (TLC), solid, de novo phospholipid synthesis inhibito, Calbiochem

Synonym(s):

Cerulenin, Cephalosporium caerulens

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About This Item

Empirical Formula (Hill Notation):

C₁₂H₁₇NO₃

CAS Number:

17397-89-6

Molecular Weight:

223.27

UNSPSC Code:

41106500

NACRES:

NA.77

MDL number:

MFCD00083595

Assay:

≥98% (TLC)

Form:

solid

Quality level:

100

Storage condition:

OK to freeze, protect from light

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Properties

Product Name

Cerulenin, Cephalosporium caerulens, An antifungal antibiotic that inhibits sterol and fatty acid biosynthesis.

Quality Level

100

description

Merck USA index - 14, 2004

assay

≥98% (TLC)

form

solid

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze, protect from light

color

white to off-white

solubility

DMSO: 10 mg/mL, ethanol: 5 mg/mL, acetone: soluble

shipped in

ambient

storage temp.

2-8°C

SMILES string

NC(=O)[C@@H]1O[C@@H]1C(=O)CC\C=C\C\C=C\C

InChI

1S/C12H17NO3/c1-2-3-4-5-6-7-8-9(14)10-11(16-10)12(13)15/h2-3,5-6,10-11H,4,7-8H2,1H3,(H2,13,15)/b3-2+,6-5+/t10-,11-/m1/s1

InChI key

GVEZIHKRYBHEFX-NQQPLRFYSA-N

Description

General description

An anti-fungal antibiotic that inhibits fatty acid biosynthesis by binding, in equimolar ratio, to β-keto-acyl-ACP synthase. Also inhibits sterol synthesis by blocking the activity of HMG-CoA synthetase activity. Systemic and intracerebroventricular of this compound reduces feeding and induces weight loss.

An antifungal antibiotic that inhibits sterol and fatty acid biosynthesis. In fatty acid synthesis, reported to bind in equimolar ratio to β-keto-acyl-ACP synthase. In sterol synthesis, inhibits HMG-CoA synthetase activity. Also shown to inhibit feeding and induce dramatic weight loss in mice.

Biochem/physiol Actions

Primary Target
sterol & fatty acid biosynthesis

Packaging

Packaged under inert gas

Other Notes

Loftus, T.M., et al. 2000. Science288, 2379.
Inokashi, J., et al. 1994. Mol. Gen. Genet. 244, 90.
Schneider, F., et al. 1993. Biochim. Biophys. Acta 1152, 243.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Harmful (C)

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pictograms

GHS07

signalword

Warning

hcodes

H302

pcodes

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c