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C2389

Sigma-Aldrich

Cerulenin

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

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C12H17NO3
Numero CAS:
17397-89-6
Peso molecolare:
223.27
Beilstein:
4140423
Numero CE:
241-424-8
Numero MDL:
MFCD00083595
Codice UNSPSC:
51111800
ID PubChem:
24892323
NACRES:
NA.77

Nome del prodotto

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

Origine biologica

Cephalosporium caerulens

Livello qualitativo

200

Saggio

≥98% (HPLC)

Stato

powder

Punto di fusione

93 °C

Solubilità

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

Spettro attività antibiotica

fungi

Modalità d’azione

enzyme | inhibits

Temperatura di conservazione

−20°C

Stringa SMILE

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
PTNNGEBMCNMENY-JIVMHGEESA-N

Informazioni sul gene

human ... FASN(2194)

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Descrizione generale

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.

Applicazioni

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

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H302

Classi di pericolo

Acute Tox. 4 Oral

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

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Certificati d'analisi (COA)

Lot/Batch Number
119M4035V
109M4083V
14190402
019M4065V
019M4064V

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Sigma-Aldrich

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2-Bromooctanoic acid

TOFA A cell-permeable furoic acid compound that acts as a potent, reversible, and competitive inhibitor of acetyl-CoA carboxylase (ACC), a key enzyme involved in the fatty acid biosynthesis.

Sigma-Aldrich

613450

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FR-900098 monosodium salt ≥97% (NMR)

Sigma-Aldrich

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FR-900098 monosodium salt

Sorafenib European Pharmacopoeia (EP) Reference Standard

Y0002098

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BMS-303141 ≥98% (HPLC)

Sigma-Aldrich

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BMS-303141

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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