C2389

Cerulenin

Name: Cerulenin
Brand: SIGMA

from Cephalosporium caerulens, ≥98% (HPLC), powder, de novo phospholipid synthesis inhibitor

Synonym(s):

Helicocerin, (2R,3S,E,E)-2,3-Epoxy-4-oxo-7,10-dodecadienamide

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About This Item

Empirical Formula (Hill Notation):

C₁₂H₁₇NO₃

CAS Number:

17397-89-6

Molecular Weight:

223.27

NACRES:

NA.77

PubChem Substance ID:

24892323

UNSPSC Code:

51111800

EC Number:

241-424-8

MDL number:

MFCD00083595

Beilstein/REAXYS Number:

4140423

Product Name

Cerulenin, ≥98% (HPLC), from Cephalosporium caerulens

InChI key

PTNNGEBMCNMENY-JIVMHGEESA-N

InChI

1S/C13H18O3/c1-3-4-5-6-7-8-9-11(15)13-12(16-13)10(2)14/h3-4,6-7,12-13H,5,8-9H2,1-2H3/b4-3+,7-6+/t12-,13+/m0/s1

SMILES string

C/C=C/C/C=C/CCC([C@@H]1[C@H](C(N)=O)O1)=O

biological source

Cephalosporium caerulens

assay

≥98% (HPLC)

form

powder

mp

93 °C

solubility

acetone: 19.60-20.40 mg/mL, clear to slightly hazy, colorless to yellow

antibiotic activity spectrum

fungi

mode of action

enzyme | inhibits

storage temp.

−20°C

Quality Level

200

Gene Information

human ... FASN(2194)

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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Application

Cerulenin has been used:

as a fatty acid synthase inhibitor to study its effects on aldosterone-induced trained immunity
as a blocker of fatty acid synthase to study its effects on the replication of severe acute respiratory syndrome coronavirus 2 (SARS-CoV2)
as a supplement in yeast extract–peptone–dextrose/glycerol (YPD/G) agar plates for the isolation of cerulenin-resistant yeast strains

General description

Cerulenin, an inhibitor of de novo phospholipid synthesis triggers apoptosis in various wild type p53 and mutant p53 tumor cell lines. This fungal antibiotic also blocks the condensing enzyme involved in fatty acid and polyketide biosynthesis.

pictograms

GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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