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Merck

C2389

Cerulenin

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

Sinónimos:

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

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Fórmula empírica (notación de Hill):
C12H17NO3
Número CAS:
Peso molecular:
223.27
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
51111800
EC Number:
241-424-8
MDL number:
Beilstein/REAXYS Number:
4140423
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
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Nombre del producto

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

biological source

Cephalosporium caerulens

Quality Level

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)

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


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pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Clase de almacenamiento

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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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
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
Biosynthesis of Enediyne Antibiotics
Iwasaki S
Chemistry & Biology (1999)