Hymeglusin

Hymeglusin is a fungal beta-lactone antibiotic that inhibits HMG-CoA synthase (IC50 = 0.12 µM) by covalently modifying the active Cys129 residue of the enzyme. At a dose of 25 mg/kg, hymeglusin inhibits cholesterol biosynthesis in rats by 45%. Chiral studies indicate that the (2R,3R)-beta-lactone moiety of hymeglusin is important for eliciting the specific inhibition of HMG-CoA synthase. As a cell-wall targeting antibiotic, hymeglusin has been used to investigate the role of a gene important for controlling S. aureus virulence in a mouse sepsis model of infection.Formal Name: 11-[3R-(hydroxymethyl)-4-oxo-2R-oxetanyl]-3,5,7R-trimethyl-2E,4E-undecadienoic acid. CAS Number: 29066-42-0. Synonyms: Antibiotic 1233A, Antibiotic F 244, L 659,699. Molecular Formula: C18H28O5. Formula Weight: 324.4. Purity: >95%. Formulation: (Request formulation change), A crystalline solid. Solubility: Chloroform: Soluble, DMSO: Soluble, Ethanol: Soluble, Methanol: Soluble. SMILES: OC[C@@H](C1=O)[C@H](O1)CCCC[C@@H](C)C/C(C)=C/C(C)=C/C(O)=O. InChi Code: InChI=1S/C18H28O5/c1-12(8-13(2)9-14(3)10-17(20)21)6-4-5-7-16-15(11-19)18(22)23-16/h9-10,12,15-16,19H,4-8,11H2,1-3H3,(H,20,21)/b13-9+,14-10+/t12-,15-,16-/m1/s1. InChi Key: ODCZJZWSXPVLAW-KXCGKLMDSA-N. Origin: Fungus/Scopulariopsis sp. F-244.