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
• 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: 51111800
• PubChem Substance ID: 24892323
• NACRES: NA.77

Properties

• product name: Cerulenin, ≥98% (HPLC), from Cephalosporium caerulens
• 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)

Description

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

Safety Information

• pictograms: 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