Cerulenin

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

General

Type : Epoxide, Carboxamide

Chemical_Nomenclature : (2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide

Canonical SMILES : 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

InChIKey : GVEZIHKRYBHEFX-NQQPLRFYSA-N

Other name(s) : Helicocerin  ||  UNII-MF286Y830Q  ||  2,3-Epoxy-4-oxo-7,10-dodecadienamide  ||  CHEMBL45627  ||  CHEBI:171741  ||  CHEBI:94649  ||  ZINC4102315  ||  DB01034


MW : 223.27

Formula : C12H17NO3

CAS_number : 17397-89-6

PubChem : 5282054

UniChem : GVEZIHKRYBHEFX-NQQPLRFYSA-N

Target

Structures : No structure

Families : Dieckmann_Cyclase

References (1)

Title : Structural Basis for Enzymatic Off-Loading of Hybrid Polyketides by Dieckmann Condensation - Cogan_2020_ACS.Chem.Biol_15_2783
Author(s) : Cogan DP , Ly J , Nair SK
Ref : ACS Chemical Biology , 15 :2783 , 2020
Abstract :
PubMedSearch : Cogan_2020_ACS.Chem.Biol_15_2783
PubMedID: 33017142
Gene_locus related to this paper: 9pseu-NcmC