G5 - ≥98% , CAS No.108477-18-5

CAS: 108477-18-5 Cat. No.: G276270 Molecular Weight: 414.4
AVAILABLE TO ORDER
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
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Size
Status
Price
Qty
5mg
G276270-5mg
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10mg
G276270-10mg
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25mg
G276270-25mg
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50mg
G276270-50mg
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100mg
G276270-100mg
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250mg
G276270-250mg
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$362.90

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Why this grade

≥98% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.

🌡

Storage & shipping

Protected from light,Store at -20°C Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.

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Quality documents

SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.

📚

Literature proof

Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.

Overview

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

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
Specifications & Purity
≥98%
Biochemical and Physiological Mechanisms
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
Shipped In
Ice chest + Ice pads
This product requires cold chain shipping. Ground and other economy services are not available.
Note
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.
Purity
≥98%
Names and Identifiers
Canonical SmilesC1C(=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
InChIKeySSAMIOWVUGBIJK-KAVGSWPWSA-N
INCHI1S/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+
Isomeric 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-]
Molecular Weight 414.4
Reaxy-Rn 56949
Reaxys-RN_link_address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=56949&ln=

Documentation

📋 Safety Data Sheet (SDS)

Comprehensive hazard, handling, storage, and regulatory compliance document.

Download SDS →

✅ Certificate of Analysis (COA)

Lot-specific quality data. Enter your lot number to retrieve the exact COA.

Look up COA →

📊 Datasheet

Quick-reference summary of product specifications and applications.

View datasheet →

🔬 Specification Sheet

Full quality attributes and acceptance criteria for this grade.

View spec sheet →

Advanced Data

Taxonomic Classification

Taxonomy Tree

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassNitrobenzenes
Intermediate Tree Nodes Not available
Direct ParentNitrobenzenes
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 FrameworkAromatic 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
DescriptionThis 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
3D Structure
Interactive Chemical Structure Model





Associated Targets(Human)
U-87 MG (3946 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HepG2 (196354 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UCHL1 Tchem Ubiquitin carboxyl-terminal hydrolase isozyme L1 (107 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
USP2 Tbio Ubiquitin carboxyl-terminal hydrolase 2 (8818 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UCHL5 Tbio Ubiquitin carboxyl-terminal hydrolase isozyme L5 (42 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
USP18 Tbio Ubl carboxyl-terminal hydrolase 18 (5 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Associated Targets(non-human)
rep Replicase polyprotein 1ab (378 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mechanisms of Action
Certificates(CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemical and Physical Properties
SolubilitySoluble in a 1:3 solution of DMSO:PBS. Please see Handling instructions.
Sensitivitylight sensitive
Molecular Weight414.400 g/mol
XLogP32.600
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count7
Rotatable Bond Count2
Exact Mass414.052 Da
Monoisotopic Mass414.052 Da
Topological Polar Surface Area151.000 Ų
Heavy Atom Count29
Formal Charge0
Complexity767.000
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
The total count of all stereochemical bonds2
Covalently-Bonded Unit Count1
Solution Calculators
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