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SML0002

Sigma-Aldrich

C646

≥98% (HPLC)

Synonym(s):

4-[4-[[5-(4,5-Dimethyl-2-nitrophenyl)-2-furanyl]methylene]-4,5-dihydro-3-methyl-5-oxo-1H-pyrazol-1-yl]benzoic acid

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About This Item

Empirical Formula (Hill Notation):
C24H19N3O6
CAS Number:
328968-36-1
Molecular Weight:
445.42
MDL number:
MFCD01784780
UNSPSC Code:
12352200
PubChem Substance ID:
329825079
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

red to brown

solubility

DMSO: >25 mg/mL

storage temp.

2-8°C

SMILES string

Cc1cc(-c2ccc(\C=C3\C(C)=NN(c4ccc(cc4)C(O)=O)C3=O)o2)c(cc1C)[N+]([O-])=O

InChI

1S/C24H19N3O6/c1-13-10-20(21(27(31)32)11-14(13)2)22-9-8-18(33-22)12-19-15(3)25-26(23(19)28)17-6-4-16(5-7-17)24(29)30/h4-12H,1-3H3,(H,29,30)/b19-12-

InChI key

HEKJYZZSCQBJGB-UNOMPAQXSA-N

Related Categories

Application

C646 was used to study the role of p300 in chronic neuropathic pain in rats with chronic constriction injury.

Biochem/physiol Actions

C646 is a competitive histone acetyltransferase (HAT) p300/CBP inhibitor with a Ki of 400 nM and is selective versus other acetyltransferases.
C646 is a potent, cell permeable and selective inhibitor of p300 and CBP (p300/CBP) histone acetyltransferases. Inhibition of p300/CBP by C646 affects the activity of a variety of transcriptional factors such as NF-κB, p53 and MyoD that are associated with physiology, disease processes, hippocampal synaptic plasticity, spatial memory and contextual fear.
C646 is a potent, competitive, and selective histone acetyltransferase (HAT) p300/CBP inhibitor.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000235500
0000235500
0000144044
0000106340
0000092118

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Jia Cao et al.
Nature communications, 8(1), 131-131 (2017-07-27)
Diabetes and obesity are characterized by insulin resistance and chronic low-grade inflammation. An elevated plasma concentration of lipopolysaccharide (LPS) caused by increased intestinal permeability during diet-induced obesity promotes insulin resistance in mice. Here, we show that LPS induces endoplasmic reticulum
A R Esteves et al.
Biochimica et biophysica acta. Molecular basis of disease, 1865(8), 2008-2023 (2018-12-21)
Protein post-translational modifications (PTMs) that potentiate protein aggregation have been implicated in several neurological disorders, including Alzheimer's (AD) and Parkinson's disease (PD). In fact, Tau and alpha-synuclein (ASYN) undergo several PTMs potentiating their aggregation and neurotoxicity. Recent data posits a
Arunava Bandyopadhaya et al.
Frontiers in microbiology, 8, 1211-1211 (2017-07-18)
Some bacterial quorum sensing (QS) small molecules are important mediators of inter-kingdom signaling and impact host immunity. The QS regulated small volatile molecule 2-aminoacetophenone (2-AA), which has been proposed as a biomarker of
Ke Jin et al.
Cancer research, 77(16), 4228-4237 (2017-06-20)
Although it has long been appreciated that p300 acts as a critical Notch coactivator, the mechanistic details of p300 in Notch-mediated transcription remain unclear. We previously demonstrated that PEAK1-related kinase activating pseudokinase 1 (NACK), also known as SGK223, is a
Roger Marek et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 31(20), 7486-7491 (2011-05-20)
It is well established that the coordinated regulation of activity-dependent gene expression by the histone acetyltransferase (HAT) family of transcriptional coactivators is crucial for the formation of contextual fear and spatial memory, and for hippocampal synaptic plasticity. However, no studies
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