Tapinarof - Moligand™, ≥99% , Aryl hydrocarbon receptor agonist, CAS No.79338-84-4, Aryl hydrocarbon receptor agonist

CAS: 79338-84-4 Cat. No.: T414465 Peso molecular: 254.32 Número EC: 838-014-1

GRADE & PURITY Moligand™, ≥99%

Synonyms

5-((1E)-2-PHENYLETHEN-1-YL)-2-(PROPAN-2-YL)BENZENE-1,3-DIOL | Tapinarof (USAN) | 5-[(1E)-2-Phenylethen-1-yl]-2-(propan-2-yl)benzene-1,3-diol | GTPL9686 | AKOS025296109 | s9700 | TAPINAROF [INN] | BCP13569 | Sinefunginum [INN-Latin] | 2-Isopropyl-5-styrylb

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

Information

Tapinarof Tapinarof (GSK2894512, Benvitimod, WBI 1001, DHPS, DMVT 505) is a natural agonist of aryl hydrocarbon receptor (AhR) and induces nuclear translocation of AhR in immortalized keratinocytes (HaCaT) with EC50 of 0.16 nM. Tapinarof induces cellular apoptosis in CD4+ T cells in a dosedependent manner with IC50 of 5.2 μM.

Targets

AhR (in immortalized keratinocytes); apoptosis (in CD4+ T cells) 0.16 nM(EC50); 5.2 μM

In vitro

Tapinarof binds and activates AhR in multiple cell types, including cells of the target tissue –human skin. In addition, tapinarof moderates proinflammatory cytokine expression in stimulated peripheral blood CD4+ T cells and ex vivo human skin, and impacts barrier gene expression in primary human keratinocytes; both of these processes are likely to be downstream of AhR activation based on current evidence.

In vivo

The anti-inflammatory properties of tapinarof derive from AhR agonism is conclusively demonstrated using the mouse model of imiquimod-induced psoriasiform skin lesions. Topical treatment of AhR-sufficient mice with tapinarof leads to compound-driven reductions in erythema, epidermal thickening and tissue cytokine levels. In contrast, tapinarof has no impact on imiquimod-induced skin inflammation in AhR-deficient mice.

Cell Research(from reference)

Cell lines：HaCaT cells 

Concentrations：0.01 pM - 1 μM 

Incubation Time：30 min 

Specifications

Sinónimos

5-((1E)-2-PHENYLETHEN-1-YL)-2-(PROPAN-2-YL)BENZENE-1, 3-DIOL | Tapinarof (USAN) | 5-[(1E)-2-Phenylethen-1-yl]-2-(propan-2-yl)benzene-1, 3-diol | GTPL9686 | AKOS025296109 | s9700 | TAPINAROF [INN] | BCP13569 | Sinefunginum [INN-Latin] | 2-Isopropyl-5-styrylb

Especificaciones y pureza

Moligand™, ≥99%

Mecanismos bioquímicos y fisiológicos

Tapinarof (GSK2894512, Benvitimod, WBI 1001, DHPS, DMVT 505) is a natural agonist of aryl hydrocarbon receptor (AhR) and induces nuclear translocation of AhR in immortalized keratinocytes (HaCaT) with EC50 of 0.16 nM. Tapinarof induces cellular apoptosis

Condiciones de almacenamiento de almacenamiento

Protected from light, Store at -20°C

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Grado

Moligand™

Tipo de acción

AGONIST

Mecanismo de acción

Aryl hydrocarbon receptor agonist

Pureza

≥99%

Propiedades del producto

• ALogP: 4.526
• Recuento HBD: 2
• Enlace rotable: 3

Nombres e identificadores

• Pubchem Sid: 504764186
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504764186
• Sonrisas canónicas: CC(C)C1=C(C=C(C=C1O)C=CC2=CC=CC=C2)O
• IUPAC Name: 5-[(E)-2-phenylethenyl]-2-propan-2-ylbenzene-1,3-diol
• InChIKey: ZISJNXNHJRQYJO-CMDGGOBGSA-N
• INCHI: 1S/C17H18O2/c1-12(2)17-15(18)10-14(11-16(17)19)9-8-13-6-4-3-5-7-13/h3-12,18-19H,1-2H3/b9-8+
• Isómeros SMILES: CC(C)C1=C(C=C(C=C1O)/C=C/C2=CC=CC=C2)O
• Peso molecular: 254.32

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Clase: Stilbenes
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Stilbenes
• Alternative Parents: Monocyclic monoterpenoids Aromatic monoterpenoids Phenylpropanes Cumenes Styrenes Resorcinols 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Organooxygen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Stilbene - P-cymene - Aromatic monoterpenoid - Monocyclic monoterpenoid - Monoterpenoid - Cumene - Phenylpropane - Resorcinol - Styrene - 1-hydroxy-4-unsubstituted benzenoid - Phenol - 1-hydroxy-2-unsubstituted benzenoid - Monocyclic benzene moiety - Benzenoid - Organooxygen compound - Hydrocarbon derivative - Organic oxygen compound - Aromatic homomonocyclic compound
• Descripción: 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: 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

Objetivos asociados (humanos)

AHR Tclin Aryl hydrocarbon receptor (0 Activities)

Discover Target: AHR

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

AHR Tclin Aryl hydrocarbon receptor (1071 Activities)

Discover Target: AHR

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

Objetivos asociados (no humanos)

Escherichia coli (133304 Activities)

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

Bacillus subtilis (32866 Activities)

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Saccharomyces cerevisiae (19171 Activities)

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

Manduca sexta (30 Activities)

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Caenorhabditis elegans (1055 Activities)

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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

Hemolymph (1 Activities)

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

ProPO Prophenoloxidase (1 Activities)

Discover Target: ProPO

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

Photorhabdus luminescens (66 Activities)

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

Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Solubility (25°C) In vitro DMSO: 51 mg/mL (200.53 mM); Ethanol: 51 mg/mL (200.53 mM); Water: Insoluble
• Sensibilidad: Light sensitive
• DMSO (mg/ml) Solubilidad máxima: 51
• DMSO (mM) Solubilidad máxima: 200.534759358289
• Agua (mg/ml) Solubilidad máxima: ＜1
• Punto de fusión (°C): 148 °C
• Peso molecular: 254.320 g/mol
• XLogP3: 4.600
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 254.131 Da
• Monoisotopic Mass: 254.131 Da
• Topological Polar Surface Area: 40.500 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 280.000
• 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