3006 T3D2964 Cerulenin Cerulenin is a solid exogenous compound with the formula C12H17NO3 and an average molecular weight of 223.27 g/mol. Cerulenin belongs to the oxirane carboxylic acids and derivatives, a subclass of epoxides within the organic compounds. It is classified as an organoheterocyclic compound. This compound serves as an antibiotic, antifungal agent, antiinfective agent, and antilipemic drug. Biologically, it acts as an antimetabolite and a fatty acid synthesis inhibitor. Its recorded sources include electrical and electronic equipment, such as magnets and relays, as well as food, food processing and cookware, specifically brew kettles and the preparation of wine or sparkling wine. Cerulenin targets four proteins, specifically acting as an inhibitor of Beta-ketoacyl-[acyl-carrier-protein] synthase III (fabH), 3-oxoacyl-[acyl-carrier-protein] synthase 1 (fabB), and 3-oxoacyl-[acyl-carrier-protein] synthase 2 (fabF). It irreversibly binds to fatty acid synthase (FASN), specifically the b-ketoacyl-acyl carrier protein synthase condensation enzymes FabH, FabB, and FabF. Because a number of tumor cells and cell lines have been observed to have highly upregulated expression and activity of fatty acid synthase (FAS), the inhibition of FAS by cerulenin leads to apoptosis and cytotoxicity in human cancer cell lines. This effect is believed to be mediated by the accumulation of malonyl-coenzyme A in cells with an upregulated FAS pathway. 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 2026-05-14T16:56:22Z 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 73.68 73.47930000000001 23.62124170880265 7 4 2 -3.383222626551974 12.56245441151201 0 1 1.83 -3.26 1.22e-01 g/l Organic compounds Organoheterocyclic compounds Epoxides Oxirane carboxylic acids and derivatives 866 CED0005653 GVEZIHKRYBHEFX-NQQPLRFYSA-N 80000400000000000000000000000000a000000000000000000000000000000000000000000004004000000000000000000000020000000000000000000000000000000108000020800000000200000000000000000002000000010000000008000000000002800000000000000080000000000000100000000040410000000080000000000000000000001000000000000000000000000000000000000000080000000000000000000000000000000000000000000000000008000000000000000000000000020000000000000000000010000000000000004000000000000040000000000440000000000000000000000000000000 102060000000000010820000000000000052000002000400200400c4002001100800000000001000080008006200000008c10010000443080a00000c4110400000000000080100000630000000000004000003254040430100009800c3000000040020020000001c4300000200080100801e00411280000021002024040000c0c400008080002480808000811140016444014020000080010000000014300000800400000002840012c211002c00003880108001000000000400200000000040400000200800000010102800000000002004000010000000800000000000c000000000c0000040000002004081000908040800c0000030050040000 776t3gAAAAAQAAAAAwAAAAAAAAAQAAAAEAAAAIABBgA4AAAAAwEEBgBgAAAA AQMGADgAAAADAQQGAGAAAAACAgYAOAAAAAMBBAYAOAAAAAMBBAYAYAAAAAIC BgBgAAAAAgIGACgAAAADBAgAKAAAAAMCBiA0AAAAAQEECAAgAAAAAgYgNAAA AAEBBAYAKAAAAAMECABoAAAAAwEBBwBoAAAAAwIBCwABBAMAAgoCAwIBAwID BAQDBAQDBAUKAgMCAwYFBgQDBgcABwgACAkIAggKAAoLAAsMAAwNAA0OIA0P KAIMCgBCAQAAAAMKCwwXBAAAAAAAAAAW 2026-09-19T04:00:40Z