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Merck
CN

C2389

Cerulenin

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

Key Documents

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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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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

Exclamation mark
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

Regulatory Information

涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
0000335526
0000335528
0000335527
0000333130
0000308046

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Biosynthesis of Enediyne Antibiotics
Iwasaki S
Chemistry & Biology (1999)
[Mechanism of action of cerulenin on fatty acid synthetase and cerulenin resistance in a cerulenin-producing fungus].
H Tomoda et al.
Seikagaku. The Journal of Japanese Biochemical Society, 57(3), 190-201 (1985-03-01)
Marilyn D Resh
Methods (San Diego, Calif.), 40(2), 191-197 (2006-10-03)
Covalent attachment of palmitate to proteins is a post-translational modification that exerts diverse effects on protein localization and function. The three key technical approaches required for an investigator to determine the role of palmitoylation of your favorite palmitoylated protein (YFPP)
Key role of mitochondria in cerulenin-mediated apoptosis
Heiligtag SJ, et al.
Cell Death and Differentiation (2002)
Darren C J Wong et al.
Frontiers in plant science, 9, 839-839 (2018-07-05)
Hundreds of orchid species secure pollination by sexually luring specific male insects as pollinators by chemical and morphological mimicry. Yet, the biochemical pathways involved in the synthesis of the insect sex pheromone-mimicking volatiles in these sexually deceptive plants remain poorly
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