Zaragozic Acid A - Moligand™, ≥95% , Inhibitor of squalene synthase , CAS No.142561-96-4, Inhibitor of squalene synthase

CAS: 142561-96-4 Cat. No.: Z329476 Molecular Weight: 690.73 PubChem CID: 6438355

GRADE & PURITY Moligand™, ≥95%

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

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

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). 

Specifications

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

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

Inhibitor of squalene synthase

Purity

≥95%

Product Properties

• pKa: pKₐ: 1.47 (Predicted)

Names and Identifiers

• 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
• 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
• InChIKey: DFKDOZMCHOGOBR-NCSQYGPNSA-N
• 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
• 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

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Pentacarboxylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Pentacarboxylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Pentacarboxylic acids and derivatives
• Alternative Parents: Phenylpropanes Fatty acid esters Ketals Oxepanes 1,3-dioxanes Alpha hydroxy acids and derivatives Monosaccharides Tertiary alcohols Tetrahydrofurans Enoate esters Secondary alcohols Carboxylic acids Oxacyclic compounds Carbonyl compounds Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Pentacarboxylic acid or derivatives - Phenylpropane - Fatty acid ester - Ketal - Oxepane - Meta-dioxane - Alpha-hydroxy acid - Monocyclic benzene moiety - Hydroxy acid - Monosaccharide - Benzenoid - Fatty acyl - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Tetrahydrofuran - Tertiary alcohol - Secondary alcohol - Carboxylic acid ester - Organoheterocyclic compound - Oxacycle - Carboxylic acid - Acetal - Organooxygen compound - Organic oxide - Hydrocarbon derivative - Alcohol - Organic oxygen compound - Carbonyl group - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups.
• External Descriptors: Other Polyketides

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

FDFT1 Tchem Squalene synthase (5 Activities)

Discover Target: FDFT1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

AKT1 Tchem Serine/threonine-protein kinase AKT (9192 Activities)

Discover Target: AKT1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Fdft1 Squalene synthetase (34 Activities)

Discover Target: Fdft1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Aspergillus niger (16508 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cryptococcus neoformans (21258 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Candida albicans (78123 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Rattus norvegicus (775804 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

dengue virus type 2 (2400 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

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)
• Molecular Weight: 690.700 g/mol
• XLogP3: 4.900
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 19
• Exact Mass: 690.289 Da
• Monoisotopic Mass: 690.289 Da
• Topological Polar Surface Area: 223.000 Ų
• Heavy Atom Count: 49
• Formal Charge: 0
• Complexity: 1290.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1