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:
Molecular Weight:
223.27
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
51111800
EC Number:
241-424-8
MDL number:
Beilstein/REAXYS Number:
4140423
Product Name
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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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)