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Zaragozic Acid A - 95%, high purity , CAS No.142561-96-4, Inhibitor of squalene synthase
a squalene synthetase inhibitor and fungal metabolite containing a novel 4,6,7-trihydroxy-2,8-dioxobicyclo[3.2.1]octane-3,4,5-tricarb
Basic Description Synonyms J-007666 | Zaragozic acid A | (1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-4,7-dihydroxy-6-((S)-6-methyl-4-methyl-oct-2-enoyloxy)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid | 3vjc | GTPL3057 | Ibacitabin | SQU Specifications & Purity Moligand™, ≥95% Source Unidentified fungus Storage Temp Store at -20°C Shipped In Ice chest + Ice pads Grade Moligand™ Action Type INHIBITOR Mechanism of action Inhibitor of squalene synthase Product Description Zaragozic Acid A is a squalene synthetase inhibitor and fungal metabolite containing a novel 4,6,7-trihydroxy-2,8-dioxobicyclo[3.2.1]octane-3,4,5-tricarboxylic acid core. Squalene synthase catalyzes the first committed step in cholesterol synthesis, mediating the reductive dimerization of farnesyl pyrophosphate 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). Zaragozic Acid A dose-dependently reduces cholesterol synthesis in HepG2 cells (IC50 = 6 μM) and inhibits hepatic cholesterol synthesis in mice (ED50 = 0.2 mg/kg).
Associated Targets(Human) Associated Targets(non-human) Names and Identifiers IUPAC Name (1S,3S,4S,5R,6R,7R)-1-[(4S,5R)-4-acetyloxy-5-methyl-3-methylidene-6-phenylhexyl]-6-[(E,4S,6S)-4,6-dimethyloct-2-enoyl]oxy-4,7-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid INCHI 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)/b14-13+/t19-,20+,22+,26+,27+,28+,29+,33-,34+,35-/m0/s1 InChi Key DFKDOZMCHOGOBR-NCSQYGPNSA-N Canonical SMILES CCC(C)CC(C)C=CC(=O)OC1C(C2(OC(C(C1(O2)C(=O)O)(C(=O)O)O)C(=O)O)CCC(=C)C(C(C)CC3=CC=CC=C3)OC(=O)C)O Isomeric SMILES CC[C@H](C)C[C@H](C)/C=C/C(=O)O[C@@H]1[C@H]([C@]2(O[C@@H]([C@]([C@@]1(O2)C(=O)O)(C(=O)O)O)C(=O)O)CCC(=C)[C@H]([C@H](C)CC3=CC=CC=C3)OC(=O)C)O WGK Germany 3 PubChem CID 6438355 Molecular Weight 690.73
Chemical and Physical Properties Solubility Soluble in ethanol (10 mg/ml), methanol, DMF, DMSO (10 mg/ml), and water (moderate). Refractive Index n20D1.59 (Predicted) Boil Point(°C) ~850.1° C at 760 mmHg (Predicted)
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