GW4064 - Moligand™, ≥98% , Agonist of Farnesoid X receptor, CAS No.278779-30-9, Agonist of Farnesoid X receptor

CAS: 278779-30-9 Cat. No.: G129700 Molecular Weight: 542.84 EC Number: 631-072-7

GRADE & PURITY Moligand™, ≥98%

Synonyms

GW-4064 | Benzoic acid, 3-(2-(2-chloro-4-((3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl)methoxy)phenyl)ethenyl)- | GW-4064X | UNII-SR225WUZ0H | CHEBI:79997 | (E)-3-(2-chloro-4-((3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl)methoxy)styryl)benzo

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

GW4064 is an agonist of farnesoid X receptor (FXR) with EC50 of 65 nM in CV1 cell line and displays no activity at other nuclear receptors at concentrations up to 1 μM.

Specifications

Synonyms

GW-4064 | Benzoic acid, 3-(2-(2-chloro-4-((3-(2, 6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl)methoxy)phenyl)ethenyl)- | GW-4064X | UNII-SR225WUZ0H | CHEBI:79997 | (E)-3-(2-chloro-4-((3-(2, 6-dichlorophenyl)-5-isopropylisoxazol-4-yl)methoxy)styryl)benzo

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Selective, non-steroidal farnesoid X receptor (FXR) agonist (EC50= 15 nM). Displays no activity at other nuclear receptors at concentrations up to 1μM. Improves hyperglycaemia and hyperlipidemia in diabetic db/db mice. Shown to suppress autophagy in nutri

Storage

Store at 2-8°C

Shipped In

Wet ice

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

Grade

Moligand™

Action Type

AGONIST

Mechanism of action

Agonist of Farnesoid X receptor

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488196405
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488196405
• Canonical Smiles: CC(C)C1=C(C(=NO1)C2=C(C=CC=C2Cl)Cl)COC3=CC(=C(C=C3)C=CC4=CC(=CC=C4)C(=O)O)Cl
• IUPAC Name: 3-[(E)-2-[2-chloro-4-[[3-(2,6-dichlorophenyl)-5-propan-2-yl-1,2-oxazol-4-yl]methoxy]phenyl]ethenyl]benzoic acid
• InChIKey: BYTNEISLBIENSA-MDZDMXLPSA-N
• INCHI: 1S/C28H22Cl3NO4/c1-16(2)27-21(26(32-36-27)25-22(29)7-4-8-23(25)30)15-35-20-12-11-18(24(31)14-20)10-9-17-5-3-6-19(13-17)28(33)34/h3-14,16H,15H2,1-2H3,(H,33,34)/b10-9+
• Isomeric SMILES: CC(C)C1=C(C(=NO1)C2=C(C=CC=C2Cl)Cl)COC3=CC(=C(C=C3)/C=C/C4=CC(=CC=C4)C(=O)O)Cl
• WGK Germany: 3
• Alternate CAS: 292047-56-4,1089660-72-9,278779-30-9
• MeSH Entry Terms: GW 4064;GW-4064;GW4064
• Molecular Weight: 542.84
• Reaxy-Rn: 10125635
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=10125635&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Stilbenes

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Stilbenes
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Stilbenes
• Alternative Parents: Benzoic acids Styrenes Phenoxy compounds Phenol ethers Benzoyl derivatives Dichlorobenzenes Alkyl aryl ethers Aryl chlorides Heteroaromatic compounds Isoxazoles Oxacyclic compounds Carboxylic acids Azacyclic compounds Monocarboxylic acids and derivatives Hydrocarbon derivatives Organic oxides Organochlorides Organonitrogen compounds Organopnictogen compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Stilbene - Benzoic acid - Benzoic acid or derivatives - 1,3-dichlorobenzene - Phenol ether - Styrene - Benzoyl - Phenoxy compound - Halobenzene - Chlorobenzene - Alkyl aryl ether - Benzenoid - Aryl chloride - Monocyclic benzene moiety - Aryl halide - Isoxazole - Heteroaromatic compound - Azole - Oxacycle - Azacycle - Organoheterocyclic compound - Carboxylic acid derivative - Carboxylic acid - Ether - Monocarboxylic acid or derivatives - Organopnictogen compound - Organic oxygen compound - Organic oxide - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Organochloride - Organohalogen compound - Organic nitrogen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
• External Descriptors: stilbenoid

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)

NR1H4 Tclin Bile acid receptor (40 Activities)

Discover Target: NR1H4

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

ABL1 Tclin Tyrosine-protein kinase ABL (18331 Activities)

Discover Target: ABL1

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

VDR Tclin Vitamin D receptor (26531 Activities)

Discover Target: VDR

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

THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)

Discover Target: THRB

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

GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)

Discover Target: GSK3B

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

CSNK1D Tchem Casein kinase I delta (4546 Activities)

Discover Target: CSNK1D

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

NR1H4 Tclin Bile acid receptor FXR (6228 Activities)

Discover Target: NR1H4

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

CDK2 Tchem Cyclin-dependent kinase 2 (9050 Activities)

Discover Target: CDK2

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

YES1 Tclin Tyrosine-protein kinase YES (2781 Activities)

Discover Target: YES1

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

AURKA Tchem Serine/threonine-protein kinase Aurora-A (10240 Activities)

Discover Target: AURKA

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

Caco-2 (12174 Activities)

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

Huh-7 (12904 Activities)

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

U2OS (164939 Activities)

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

HepG2 (196354 Activities)

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

POLK Tbio DNA polymerase kappa (8653 Activities)

Discover Target: POLK

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

ABCC2 Tchem Canalicular multispecific organic anion transporter 1 (1191 Activities)

Discover Target: ABCC2

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

ABCB11 Tchem Bile salt export pump (2311 Activities)

Discover Target: ABCB11

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

BRD4 Tchem Bromodomain-containing protein 4 (13122 Activities)

Discover Target: BRD4

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

RECQL Tbio ATP-dependent DNA helicase Q1 (5575 Activities)

Discover Target: RECQL

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

BLM Tchem Bloom syndrome protein (4248 Activities)

Discover Target: BLM

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

MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

Discover Target: MEN1

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

TRIM24 Tchem Transcription intermediary factor 1-alpha (2087 Activities)

Discover Target: TRIM24

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

BRPF1 Tchem Peregrin (2217 Activities)

Discover Target: BRPF1

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

HEK-293T (167025 Activities)

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

Associated Targets(non-human)

Ppard Peroxisome proliferator-activated receptor delta (358 Activities)

Discover Target: Ppard

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

Mapk1 MAP kinase ERK2 (650 Activities)

Discover Target: Mapk1

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

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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

Fgfr3 Fibroblast growth factor receptor 3 (21 Activities)

Discover Target: Fgfr3

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

Mus musculus (284745 Activities)

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Rattus norvegicus (775804 Activities)

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3T3-L1 (3664 Activities)

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

GCN5 Histone acetyltransferase GCN5 (89 Activities)

Discover Target: GCN5

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

Nr1h4 Bile acid receptor (142 Activities)

Discover Target: Nr1h4

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

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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

Rorc Nuclear receptor ROR-gamma (89407 Activities)

Discover Target: Rorc

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

FTL Ferritin light chain (43324 Activities)

Discover Target: FTL

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solvent:DMSO, Max Conc. mg/mL: 54.3, Max Conc. mM: 100
• Molecular Weight: 542.800 g/mol
• XLogP3: 8.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 541.061 Da
• Monoisotopic Mass: 541.061 Da
• Topological Polar Surface Area: 72.600 Ų
• Heavy Atom Count: 36
• Formal Charge: 0
• Complexity: 742.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• 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

References

1. Zhiyuan Meng, Sen Yan, Wei Sun, Jin Yan, Miaomiao Teng, Ming Jia, Sinuo Tian, Zhiqiang Zhou, Wentao Zhu.  (2023)  Chlorothalonil induces obesity in mice by regulating host gut microbiota and bile acids metabolism via FXR pathways.  JOURNAL OF HAZARDOUS MATERIALS,      [PMID:37003002] [10.1016/j.jhazmat.2023.131310]