3006 T3D2964 Cerulenin Cerulenin is an antifungal antibiotic that inhibits sterol and fatty acid biosynthesis. In fatty acid synthesis, reported to bind in equimolar ratio to b-keto-acyl-ACP synthase. In sterol synthesis, inhibits HMG-CoA synthetase activity. It is also shown to inhibit feeding and induce dramatic weight loss in mice. It is found naturally in the Cephalosporium caerulensfungus. [Wikipedia] 17397-89-6 5282054 C12H17NO3 223.120840 White powder. 93.5°C Slightly soluble Irreversibly binds to fatty acid synthase, specifically b-ketoacyl-acyl carrier protein synthase (FabH, FabB and FabF condensation enzymes). A number of tumor cells and cell lines have been observed to have highly upregulated expression and activity of fatty acid synthase (FAS). Inhibition of FAS by cerulenin leads to cytotoxicity and apoptosis in human cancer cell lines, an effect believed to be mediated by the accumulation of malonyl-coenzyme A in cells with an upregulated FAS pathway. LD50: 547 mg/kg (Oral, Mouse) (A308) No indication of carcinogenicity to humans (not listed by IARC). For use as a biochemical tool, Cerulenin is shown to cause dramatic weight loss in animals Symptoms of overexposure include moderate to severe erythema (redness) and moderate edema (raised skin), nausea, vomiting, and headache. 2009-07-21T20:28:13Z 2026-04-03T15:58:33Z Cerulenin C12058 171741 CPD-6901 Cerulenin DB01034 true [H]\C(C)=C(\[H])C\C([H])=C(/[H])CCC(=O)[C@@]1([H])O[C@@]1([H])C(O)=N C12H17NO3 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 GVEZIHKRYBHEFX-NQQPLRFYSA-N 223.272 223.120843411 Exogenous Solid 1.2 HMDB15168 CHEMBL45627 26530 <p>Garfield P. Royer, Craig A. Townsend, &#8220;Cerulenin compounds for fatty acid synthesis inhibition.&#8221; U.S. Patent US5539132, issued July, 1975.</p> CHEM002327 DTXSID2040995 NS00025714 (2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboximidic acid