| Stereochemistry | ABSOLUTE |
| Molecular Formula | C12H17NO3 |
| Molecular Weight | 223.2683 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 2 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]1(O[C@]1([H])C(=O)CC\C=C\C\C=C\C)C(N)=O
InChI
InChIKey=GVEZIHKRYBHEFX-NQQPLRFYSA-N
InChI=1S/C12H17NO3/c1-2-3-4-5-6-7-8-9(14)10-11(16-10)12(13)15/h2-3,5-6,10-11H,4,7-8H2,1H3,(H2,13,15)/b3-2+,6-5+/t10-,11-/m1/s1
| Molecular Formula | C12H17NO3 |
| Molecular Weight | 223.2683 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 2 |
| Optical Activity | UNSPECIFIED |
Cerulenin ((2R,3S)-2,3-epoxy-4-oxo-7,10-trans, trans-dodecadienoylamide) is an antifungal antibiotic isolated from Cephalosporium caerulens, that inhibits eukaryotic lipid and sterol synthesis and blocks lipid modification of proteins. Cerulenin is a potent inhibitor of fatty acid synthase (FAS). It inhibits all known types of FASs: both multifunctional enzyme complexes (Type I) (from yeast, rat liver, mammalian cells, and certain bacteria) and unassociated enzymes (Type II) (from most bacteria, and higher plants). Cerulenin blocks the synthesis of polyketides in a wide variety of organisms, including actinomycetes, fungi, and higher plants. In addition, cerulenin is suggested to inhibit the condensation step in polyketide synthesis as well as fatty acid synthesis. Cerulenin has a wide range of antimicrobial activity, the drug significantly inhibits the growth of yeast-like fungi, such as Candida, Saccharomyces, and Cryptococcus. Cerulenin is commercially available as a biochemical reagent for widespread use in the field of obesity, cancer biology, posttranslational protein modification system, drug discovery research and so on.
Originator
Approval Year
Sample Use Guides
SCID mice were treated with Cerulenin 15 and 30 mg/kg every 3 days
Route of Administration:
Intraperitoneal
To measure the cytotoxicity of cerulenin against HCT116 and RKO cells, 3x103 cells were plated per well onto 96-well plates. Following overnight culture, cerulenin and oxaliplatin were added at specified concentra¬tions. After 24 h of incubation, cell viability was measured by the mitochondrial activity in reducing 2-(2-methoxy-4-nitrophenyl)-3-(4-nitrophenyl)-5-(2,4-disulfophenyl)-2H-tetra¬zolium monosodium salt (WST-8) to formazan using a Cell Counting kit-8 (Dojindo Laboratories, Kumamoto, Japan). Cells were incubated with a reagent according to the manufac¬turer's instructions. Plates were read at A450 on a spectrometer.