Wiskostatin - ≥98%(HPLC) , CAS No.253449-04-6

CAS: 253449-04-6 Cat. No.: W169057 Molecular Weight: 426.15 EC Number: 686-020-6 PubChem CID: 2775510

GRADE & PURITY ≥98%(HPLC)

Synonyms

AS-75867 | J-503093 | KBioGR_000620 | 3,6-Dibromo-alpha-[(dimethylamino)methyl ]-9H-cabazole-9-ethanol | CBDivE_008357 | Oprea1_105682 | C17H18Br2N2O | MFCD00218393 | Oprea1_198540 | Wiskostatin | KBio3_001099 | NCGC00163493-02 | HY-12534 | NCGC00179231-0

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Wiskostatin is a cell-permeable N-alkylated carbazole derivative that selectively blocks actin filament assembly. The compound acts as a selective, reversible inhibitor of N-WASP (neural Wiskott Aldrich syndrome protein), a signal integrating protein. Wiskostatin also binds to N-WASP, stabilize the autoinhibited conformation and prevent the activation of Arp2/3 (actin-related protein 2/3) complex.

Wiskostatin is a selective inhibitor of actin filament assembly

Specifications

Synonyms

AS-75867 | J-503093 | KBioGR_000620 | 3, 6-Dibromo-alpha-[(dimethylamino)methyl ]-9H-cabazole-9-ethanol | CBDivE_008357 | Oprea1_105682 | C17H18Br2N2O | MFCD00218393 | Oprea1_198540 | Wiskostatin | KBio3_001099 | NCGC00163493-02 | HY-12534 | NCGC00179231-0

Specifications & Purity

≥98%(HPLC)

Biochemical and Physiological Mechanisms

Wiskostatin is a selective inhibitor of N-WASP, a ubiquitously expressed member of the Wiskott-Aldrich Syndrome protein (WASp) family that regulates actin polymerization. Wiskostatin inhibits actin-dependent cellular functions, including migration, transm

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

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

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%(HPLC)

Names and Identifiers

• Pubchem Sid: 504761908
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504761908
• Canonical Smiles: CN(C)CC(CN1C2=C(C=C(C=C2)Br)C3=C1C=CC(=C3)Br)O
• IUPAC Name: 1-(3,6-dibromocarbazol-9-yl)-3-(dimethylamino)propan-2-ol
• InChIKey: XUBJEDZHBUPBKL-UHFFFAOYSA-N
• INCHI: 1S/C17H18Br2N2O/c1-20(2)9-13(22)10-21-16-5-3-11(18)7-14(16)15-8-12(19)4-6-17(15)21/h3-8,13,22H,9-10H2,1-2H3
• Isomeric SMILES: CN(C)CC(CN1C2=C(C=C(C=C2)Br)C3=C1C=CC(=C3)Br)O
• WGK Germany: 3
• PubChem CID: 2775510
• Molecular Weight: 426.15

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Biphenyls and derivatives
        • Level5 Brominated biphenyls
          • Level6 Polybrominated biphenyls

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Biphenyls and derivatives
• Intermediate Tree Nodes: Brominated biphenyls
• Direct Parent: Polybrominated biphenyls
• Alternative Parents: Carbazoles N-alkylindoles Indoles Substituted pyrroles Aryl bromides Heteroaromatic compounds Trialkylamines Secondary alcohols 1,2-aminoalcohols Azacyclic compounds Organopnictogen compounds Organobromides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Polybrominated biphenyl - Carbazole - N-alkylindole - Indole - Indole or derivatives - Aryl bromide - Aryl halide - Substituted pyrrole - Heteroaromatic compound - Pyrrole - 1,2-aminoalcohol - Tertiary aliphatic amine - Tertiary amine - Secondary alcohol - Azacycle - Organoheterocyclic compound - Organobromide - Organohalogen compound - Alcohol - Organic nitrogen compound - Organic oxygen compound - Hydrocarbon derivative - Organopnictogen compound - Amine - Organonitrogen compound - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as polybrominated biphenyls. These are organic aromatic compounds containing a biphenyl moiety, which is substituted at two or more ring positions by a bromine atom.
• External Descriptors: organobromine compound - tertiary amino compound - secondary alcohol - carbazoles

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)

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

GBA1 Tclin Beta-glucocerebrosidase (14647 Activities)

Discover Target: GBA1

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

EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

Discover Target: EHMT2

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

SMN1 Tchem Survival motor neuron protein (34246 Activities)

Discover Target: SMN1

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

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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

Pseudomonas aeruginosa (123386 Activities)

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

Plasmodium falciparum (966862 Activities)

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

L6 (7924 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

Mapt Microtubule-associated protein tau (6 Activities)

Discover Target: Mapt

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

ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)

Discover Target: ffp

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

HSP90 (947 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: DMSO: 10 mg/mL, clear
• Melt Point(°C): 148-150°C
• Molecular Weight: 426.100 g/mol
• XLogP3: 4.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 425.977 Da
• Monoisotopic Mass: 423.979 Da
• Topological Polar Surface Area: 28.400 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 356.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Qiankai Shi, Ran Zhao, Linna Chen, Tianyi Liu, Tao Di, Chunwei Zhang, Zhiying Zhang, Fangfang Wang, Zongxi Han, Junfeng Sun, Shengwang Liu.  (2024)  Newcastle disease virus activates diverse signaling pathways via Src to facilitate virus entry into host macrophages.  JOURNAL OF VIROLOGY,      [PMID:38334327] [10.1128/jvi.01915-23]