Zaragozic Acid A

Squalene synthase catalyzes the first committed step in cholesterol synthesis, mediating the reductive dimerization of farnesyl pyrophosphate (Cay-63250) to produce squalene. Zaragozic acid A is a fungal metabolite that acts as a reversible competitive inhibitor of squalene synthase (Ki = 78 pM in vitro). It dose-dependently reduces cholesterol synthesis in HepG2 cells (IC50 = 6 µM) and inhibits hepatic cholesterol synthesis in mice (ED50 = 0.2 mg/kg). Zaragozic acid A also inhibits farnesyl transferase (FTase) and geranylgeranyl transferase type I (GGTase I) (IC50s = 216 and 50 nM, respectively).Formal Name: (7S)-11-acetate 5-[(2E,4S,6S)-4,6-dimethyl-2-octenoate]-2,7-anhydro-3,4-di-C-carboxy-8,9,10,12,13-pentadeoxy-10-methylene-12-(phenylmethyl)-L-erythro-L-glycero-D-altro-7-trideculo-7,4-furanosonic acid. CAS Number: 142561-96-4. Synonyms: L-694,599, Squalestatin S1. Molecular Formula: C35H46O14. Formula Weight: 690.7. Purity: >95%. Formulation: (Request formulation change), A solid. Solubility: DMF: Soluble, DMSO: Soluble, Ethanol: Soluble, Methanol: Soluble. SMILES: O[C@@H]1[C@@H](OC(/C=C/[C@@H](C)C[C@@H](C)CC)=O)[C@]2(C(O)=O)[C@](O)(C(O)=O)[C@@H](C(O)=O)O[C@]1(O2)CCC([C@@H](OC(C)=O)[C@H](C)CC3=CC=CC=C3)=C. InChi Code: InChI=1S/C35H46O14/c1-7-19(2)17-20(3)13-14-25(37)47-28-27(38)33(48-29(30(39)40)34(45,31(41)42)35(28,49-33)32(43)44)16-15-21(4)26(46-23(6)36)22(5)18-24-11-9-8-10-12-24/h8-14,19-20,22,26-29,38,45H,4,7,15-18H2,1-3,5-6H3,(H,39,40)(H,41,42)(H,43,44)/b14-1. InChi Key: DFKDOZMCHOGOBR-NCSQYGPNSA-N.