Substrate Report for: Cerulenin
| Cerulenin | Type | Epoxide |
|---|
| | Carboxamide |
| Other_Name (8) |
| Chemical_Nomenclature | (2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide |
| Formula | C12H17NO3 |
| CAS_number | 17397-89-6 |
| MW | 223.27 |
|  |
| Paper | Cogan_2020_ACS.Chem.Biol_15_2783 |
| Comment | Cerulenin is an epoxydodecadienamide isolated from several fungi species, including Acremonium, Acrocylindrum and Helicoceras Cephalosporium caerulens. It inhibits the biosynthesis of several lipids by interfering with enzyme function. It has a role as an antifungal agent, an antiinfective agent, an antilipemic drug, an antimetabolite, a fatty acid synthesis inhibitor and an antimicrobial agent. It is a monocarboxylic acid amide and an epoxide.In fatty acid synthesis inhibits b-keto-acyl-ACP synthase. In sterol synthesis, inhibits HMG-CoA synthetase activity. Interconversion of cerulenin from its linear to cyclic hemiaminal form,occurs in polar protic solvents. It is this hemiaminal form which is substrate of epoxide ring opening by NcmC |
| Gene_locus | 9pseu-NcmC |
| CID | 5282054 |
| Family | Dieckmann_Cyclase |
| InChIKey | GVEZIHKRYBHEFX-NQQPLRFYSA-N |
| CanonicalSMILES | CC=CCC=CCCC(=O)C1C(O1)C(=O)N |
| InChI | 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 |
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