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C2389

Sigma-Aldrich

Cerulenin

≥98% (HPLC), from Cephalosporium caerulens

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
Beilstein/REAXYS Number:
4140423
EC Number:
241-424-8
MDL number:
MFCD00083595
UNSPSC Code:
12352200
PubChem Substance ID:
24892323
NACRES:
NA.77

biological source

Cephalosporium caerulens

Quality Level

200

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

SMILES string

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

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

InChI key

PTNNGEBMCNMENY-JIVMHGEESA-N

Gene Information

human ... FASN(2194)

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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.

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

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
[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)
Su Gao et al.
American journal of physiology. Regulatory, integrative and comparative physiology, 301(1), R209-R217 (2011-04-22)
Hypothalamic fatty acid metabolism is involved in central nervous system controls of feeding and energy balance. Malonyl-CoA, an intermediate of fatty acid biosynthesis, is emerging as a significant player in these processes. Notably, hypothalamic malonyl-CoA has been implicated in leptin's
Jennifer W Lou et al.
Scientific reports, 9(1), 12987-12987 (2019-09-12)
During fatty acid biosynthesis, acyl carrier proteins (ACPs) from type I fungal fatty acid synthase (FAS) shuttle substrates and intermediates within a reaction chamber that hosts multiple spatially-fixed catalytic centers. A major challenge in understanding the mechanism of ACP-mediated substrate
Masayoshi Hashimoto et al.
Molecular plant-microbe interactions : MPMI, 28(6), 675-688 (2015-02-05)
Systemic necrosis is one of the most severe symptoms caused by plant RNA viruses. Recently, systemic necrosis has been suggested to have similar features to a defense response referred to as the hypersensitive response (HR), a form of programmed cell
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