G5 - ≥98% , CAS No.108477-18-5

CAS: 108477-18-5 Cat. No.: G276270 Summenformel: C₁₉H₁₄N₂O₇S Molekulargewicht: 414.4

GRADE & PURITY ≥98%

Synonyms

3,5-Bis[(4-nitrophenyl)methylene]-2,3,5,6-tetrahydro-4H-thiopyran-4-one-1,1-dioxide | 3,5-bis((4-Nitrophenyl)methylene)-1,1-dioxide | tetrahydro-4H-thiopyran-4-one | NSC-144303 | Ubiquitin Isopeptidase Inhibitor I | tetrahydro-3,5-bis[(4-nitrophenyl)methy

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Übersicht

A cell-permeable cross-conjugated α,β-unsaturated dienone compound that induces caspase activation and apoptosis (IC50 = 1.76 and 1.6 µM in E1A and E1A/C9DN cells, respectively) via the apoptosome-independent mitochondrial pathway by selectively inhibiting ubiquitin isopeptidase activity (IC50 ~30 µM). The cellular expression of Bax and Bak is essential for G5-activated apoptosis, while Bcl-2 appears to protect cells against the effect of G5. G5 is more potent than, but otherwise exhibits similar pharmacological effects as, Ubiquitin Isopeptidase Inhibitor II, F6. At higher concentrations (5-10 µM), shown to induce necrosis in apoptosis-resistant MEFs-DKO.
A cell-permeable cross-conjugated α,β-unsaturated dienone compound that induces caspase activation and apoptosis (IC50 = 1.76 and 1.6 µM in E1A and E1A/C9DN cells, respectively) via the apoptosome-independent mitochondrial pathway by selectively inhibiting ubiquitin isopeptidase activity (IC50 = ~ 30 µM). The cellular expression of Bax and Bak is essential for G5-activated apoptosis, while Bcl-2 appears to protect cells against the effect of G5. G5 is more potent than, but otherwise exhibits similar pharmacological effects as, Ubiquitin Isopeptidase Inhibitor II, F6 . At higher concentrations (5-10 µM), shown to induce necrosis in apoptosis-resistant MEFs-DKO.

Specifications

Synonyme

3,5-Bis[(4-nitrophenyl)methylene]-2,3,5,6-tetrahydro-4H-thiopyran-4-one-1,1-dioxide | 3,5-bis((4-Nitrophenyl)methylene)-1,1-dioxide | tetrahydro-4H-thiopyran-4-one | NSC-144303 | Ubiquitin Isopeptidase Inhibitor I | tetrahydro-3,5-bis[(4-nitrophenyl)methy

Spezifikationen & Reinheit

≥98%

Biochemische und physiologische Mechanismen

Cell permeable: yes Primary Target Ubiquitin isopeptidase activity Product does not compete with ATP. Reversible: no Target IC50: ~ 30 µM against ubiquitin isopeptidase activity; 1.76 and 1.6 µM for the induction of caspase activation and apoptosis in E1A

Storage

Protected from light,Store at -20°C

Verschickt in

Ice chest + Ice pads

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Hinweis

For maximum solubility we recommend this compound be dissolved in DMSO and then diluted with aqueous buffer of choice. This compound has a solubility of approximately 0.25 mg/ml in a 1:3 solution of DMSO:PBS (pH 7.2) using this method. We do not recommend storing the aqueous solution for more than one day. Also, DMSO solution needs to be purged with an inert gas for stability. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Reinheit

≥98%

Namen und Kennungen

• Kanonisches Lächeln: C1C(=CC2=CC=C(C=C2)[N+](=O)[O-])C(=O)C(=CC3=CC=C(C=C3)[N+](=O)[O-])CS1(=O)=O
• IUPAC Name: (3Z,5Z)-3,5-bis[(4-nitrophenyl)methylidene]-1,1-dioxothian-4-one
• InChIKey: SSAMIOWVUGBIJK-KAVGSWPWSA-N
• INCHI: 1S/C19H14N2O7S/c22-19-15(9-13-1-5-17(6-2-13)20(23)24)11-29(27,28)12-16(19)10-14-3-7-18(8-4-14)21(25)26/h1-10H,11-12H2/b15-9+,16-10+
• Isomere SMILES: C\1S(=O)(=O)C/C(=C\C2=CC=C(C=C2)[N+](=O)[O-])/C(=O)/C1=C/C3=CC=C(C=C3)[N+](=O)[O-]
• Molekulargewicht: 414.4
• Reaxy-Rn: 56949
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=56949&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Klasse Benzene and substituted derivatives
      • Subclass Nitrobenzenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Klasse: Benzene and substituted derivatives
• Subclass: Nitrobenzenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Nitrobenzenes
• Alternative Parents: Nitroaromatic compounds Thianes Sulfones Cyclic ketones Propargyl-type 1,3-dipolar organic compounds Organic oxoazanium compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Nitrobenzene - Nitroaromatic compound - Thiane - Sulfone - Ketone - C-nitro compound - Organic nitro compound - Cyclic ketone - Organic oxoazanium - Organoheterocyclic compound - Allyl-type 1,3-dipolar organic compound - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organic oxide - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Carbonyl group - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Aromatic heteromonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as nitrobenzenes. These are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro 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

Zugehörige Ziele (menschlich)

U-87 MG (3946 Activities)

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

A549 (127892 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

UCHL1 Tchem Ubiquitin carboxyl-terminal hydrolase isozyme L1 (107 Activities)

Discover Target: UCHL1

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

USP2 Tbio Ubiquitin carboxyl-terminal hydrolase 2 (8818 Activities)

Discover Target: USP2

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

UCHL5 Tbio Ubiquitin carboxyl-terminal hydrolase isozyme L5 (42 Activities)

Discover Target: UCHL5

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

USP18 Tbio Ubl carboxyl-terminal hydrolase 18 (5 Activities)

Discover Target: USP18

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

Zugehörige Ziele (nicht menschlich)

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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

Wirkungsmechanismen

Chemische und physikalische Eigenschaften

• Löslichkeit: Soluble in a 1:3 solution of DMSO:PBS. Please see Handling instructions.
• Empfindlichkeit: light sensitive
• Molekulargewicht: 414.400 g/mol
• XLogP3: 2.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 414.052 Da
• Monoisotopic Mass: 414.052 Da
• Topological Polar Surface Area: 151.000 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 767.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 2
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 2
• Covalently-Bonded Unit Count: 1

Häufig gestellte Fragen

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at ?20 °C, protected from light. The material is light-sensitive — keep it in its original opaque or amber container.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 108477-18-5, the molecular formula is C19H14N2O7S, and the molecular weight is 414.4 g/mol. InChIKey SSAMIOWVUGBIJK-KAVGSWPWSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.