AZ876 - Moligand™, ≥99% , Agonist of Liver X receptor-α;Agonist of Liver X receptor-β, CAS No.898800-26-5, Agonist of Liver X receptor-α;Agonist of Liver X receptor-β

CAS: 898800-26-5 Cat. No.: A413448 Molecular Weight: 439.57

GRADE & PURITY Moligand™, ≥99%

Synonyms

2-tert-butyl-1,1-dioxo-5-phenyl-4-(4-piperidin-1-ylanilino)-1,2-thiazol-3-one | AZ12260493 | AZ 87

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

AZ876 AZ876 is a novel high-affinity Liver X Receptor (LXR) agonist with Ki values of 0.007 μM and 0.011 μM for human LXRα and LXRβ respectively.

Targets

LXRα ; LXRβ 0.007 μM(Ki); 0.011 μM(Ki)

In vitro

In binding assays, AZ876 is 25-fold and 2.5-fold more potent than GW3965 on human (h)LXRα and hLXRβ respectively. In reporter transactivation assays, AZ876 is 196-fold and fivefold more potent than GW3965 on hLXRα and hLXRβ respectively. AZ876 is also more potent than GW3965 on mouse (m)LXRα (248-fold) and mLXRβ (10.5-fold). AZ876 is four- to sevenfold more potent than GW3965 on the expression of ABCA1 mRNA in hamster and human blood PMN cells. AZ876 is highly selective with respect to other nuclear hormone receptors, including retinoid X receptor, farnesoid X receptor, thyroid hormone receptor (TR)α or TRβ, when tested in agonist mode in fluorescence resonance energy transfer assays.

In vivo

AZ876 is a dual partial LXR agonist that has been shown to reduce atherosclerosis in mice without affecting liver or plasma triglyceride levels when administered in low dose. Chronic administration of the LXR agonist AZ876 attenuates pathological cardiac hypertrophy in a murine model of chronic pressure overload without altering systemic blood pressure, implicating heart-specific effects. AZ876 treatment diminishes myocardial fibrosis and suppresses induction of profibrotic gene expression.

Specifications

Synonyms

2-tert-butyl-1, 1-dioxo-5-phenyl-4-(4-piperidin-1-ylanilino)-1, 2-thiazol-3-one | AZ12260493 | AZ 87

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

AZ876 is a novel high-affinity Liver X Receptor (LXR) agonist with Ki values of 0.007 μM and 0.011 μM for human LXRα and LXRβ respectively.

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

AGONIST

Mechanism of action

Agonist of Liver X receptor-α;Agonist of Liver X receptor-β

Purity

≥99%

Product Properties

• ALogP: 3.837
• hba_count: 3
• HBD Count: 1
• Rotatable Bond: 5

Names and Identifiers

• Pubchem Sid: 504766626
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504766626
• Canonical Smiles: CC(C)(C)N1C(=O)C(=C(S1(=O)=O)C2=CC=CC=C2)NC3=CC=C(C=C3)N4CCCCC4
• IUPAC Name: 2-tert-butyl-1,1-dioxo-5-phenyl-4-(4-piperidin-1-ylanilino)-1,2-thiazol-3-one
• InChIKey: IVANYIPLGFVBGR-UHFFFAOYSA-N
• INCHI: 1S/C24H29N3O3S/c1-24(2,3)27-23(28)21(22(31(27,29)30)18-10-6-4-7-11-18)25-19-12-14-20(15-13-19)26-16-8-5-9-17-26/h4,6-7,10-15,25H,5,8-9,16-17H2,1-3H3
• Isomeric SMILES: CC(C)(C)N1C(=O)C(=C(S1(=O)=O)C2=CC=CC=C2)NC3=CC=C(C=C3)N4CCCCC4
• MeSH Entry Terms: AZ 876;AZ-876;AZ876 cpd
• Molecular Weight: 439.57
• Reaxy-Rn: 12645349
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=12645349&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Piperidines
      • Subclass Phenylpiperidines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Piperidines
• Subclass: Phenylpiperidines
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylpiperidines
• Alternative Parents: Alpha amino acids and derivatives Dialkylarylamines Aniline and substituted anilines Secondary alkylarylamines Thiazolines Organosulfonic acids and derivatives Enamines Azacyclic compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Phenylpiperidine - Alpha-amino acid or derivatives - Tertiary aliphatic/aromatic amine - Aniline or substituted anilines - Dialkylarylamine - Secondary aliphatic/aromatic amine - Monocyclic benzene moiety - Benzenoid - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Ortho-thiazoline - Tertiary amine - Amino acid or derivatives - Secondary amine - Enamine - Carboxylic acid derivative - Azacycle - Amine - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Organonitrogen compound - Carbonyl group - Organic oxygen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
• External Descriptors: Not available

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)

NR1H2 Tchem Oxysterols receptor LXR-beta (1 Activities)

Discover Target: NR1H2

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

NR1H3 Tchem Oxysterols receptor LXR-alpha (1 Activities)

Discover Target: NR1H3

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

HepG2 (196354 Activities)

Explore this target

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

Associated Targets(non-human)

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility (25°C) In vitro DMSO: 88 mg/mL (200.19 mM)
• DMSO(mg / mL) Max Solubility: 88
• DMSO(mM) Max Solubility: 200.195645744705
• Water(mg / mL) Max Solubility: -1
• Molecular Weight: 439.600 g/mol
• XLogP3: 4.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 439.193 Da
• Monoisotopic Mass: 439.193 Da
• Topological Polar Surface Area: 78.100 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 789.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1