Zaragozic acid A

Zaragozic acid A Structure
CAS No.
142561-96-4
Chemical Name:
Zaragozic acid A
Synonyms
Aids111671;Gr 105155x;Aids-111671;Squalestatin 1;Squalestatin A;Zaragozic Acid;ZARAGOZIC ACID A;DFKDOZMCHOGOBR-NCSQYGPNSA-N;Squalestatin A, Squalestatin S1, L 694599;L-Erythro-L-glycero-D-altro-7-trideculo-7,4-furanosonic acid, 2,7-anhydro-3,4-di-C-carboxy-8,9,10,12,13-pentadeoxy-10-methylene-12-(phenylmethyl)-, 11-acetate 5-[(2E,4S,6S)-4,6-dimethyl-2-octenoate], (7S)-
CBNumber:
CB1505421
Molecular Formula:
C35H46O14
Molecular Weight:
690.73
MOL File:
142561-96-4.mol
Modify Date:
2023/5/18 11:31:06

Zaragozic acid A Properties

alpha D22 +18.3° (c = 0.60 in CHCl3); D25 +37° (c = 1.29 in methanol)
Boiling point 850.1±65.0 °C(Predicted)
Density 1.35±0.1 g/cm3(Predicted)
storage temp. −20°C
solubility Soluble in DMSO
form solid
pka 1.47±0.70(Predicted)
color white to light tan
CAS DataBase Reference 142561-96-4

SAFETY

Risk and Safety Statements

WGK Germany  3

Zaragozic acid A Chemical Properties,Uses,Production

Chemical Properties

White to light tan solid. Soluble in ethanol (10 mg/ml), methanol, DMF, DMSO (10 mg/ml), and water (moderate).

Uses

Zaragozic acid A is the major metabolite of a class of unusual bicyclic tricarboxylic acids, produced by a number of fungi in the genera Curvularia, Exserohilum, Setosphaeria and others, discovered at Merck and Glaxo in the early 1990s. In nature, zaragozic acid A acts as broad spectrum antifungal but its mode of action as an inhibitor of squalene synthase, involved in sterol biosynthesis, lead to investigation as a cholesterol lowering agent. Zaragozic acid A prepared by BioAustralis is presented as the free acid rather than the tri-sodium salt to avoid stability problems associated with hydrolysis of the salt.

Definition

ChEBI: Zaragozic acid A is a polyketide isolated from fungi that is a potent inhibitor of fungal and mammalian squalene synthase. It has a role as an EC 2.5.1.21 (squalene synthase) inhibitor and a fungal metabolite. It is a tricarboxylic acid, an acetate ester, a cyclic ketal, an oxabicycloalkane, a tertiary alcohol and a polyketide.

Application

Zaragozic Acid A is a squalene synthetase inhibitor. it targeted squalene synthase and lowered the cholesterol levels in vivo of marmosets.

Biological Activity

Zaragozic acid A is an inhibitor of acute liver cholsterol synthesis (50% inhibition dose 200 μg/ kg) with Ki value of 78pM. It inhibited cholesterol synthesis in Hep G2 cells.

Zaragozic acid A Preparation Products And Raw materials

Raw materials

Preparation Products

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Squalestatin 1 Aids111671 Aids-111671 Gr 105155x L-Erythro-L-glycero-D-altro-7-trideculo-7,4-furanosonic acid, 2,7-anhydro-3,4-di-C-carboxy-8,9,10,12,13-pentadeoxy-10-methylene-12-(phenylmethyl)-, 11-acetate 5-[(2E,4S,6S)-4,6-dimethyl-2-octenoate], (7S)- Squalestatin A, Squalestatin S1, L 694599 ZARAGOZIC ACID A DFKDOZMCHOGOBR-NCSQYGPNSA-N Zaragozic Acid Squalestatin A 142561-96-4