Skip to Content
Merck
All Photos(1)

Documents

SML1396

Sigma-Aldrich

Heclin

≥98% (HPLC)

Synonym(s):

N-(4-Acetylphenyl)-3-(5-ethyl-2-furanyl)-2-propenamide

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C17H17NO3
CAS Number:
890605-54-6
Molecular Weight:
283.32
UNSPSC Code:
12352200
PubChem Substance ID:
329825844
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

SMILES string

CC(C1=CC=C(NC(/C=C/C2=CC=C(CC)O2)=O)C=C1)=O

InChI

1S/C17H17NO3/c1-3-15-8-9-16(21-15)10-11-17(20)18-14-6-4-13(5-7-14)12(2)19/h4-11H,3H2,1-2H3,(H,18,20)/b11-10+

InChI key

SPTWXRJNCFIDRQ-ZHACJKMWSA-N

Application

Heclin has been used as a HECT-type ubiquitin E3 ligase inhibitor in human embryonic kidney (HEK293) cells. It has also been used to test its effect on dandelion-induced chloride channel protein (ClC-Ka) inhibition in HEK293 cells and fibroblast-like COS-7 cell line.

Biochem/physiol Actions

Heclin is a selective reversible inihbitor of HECT E3 ubiquitin ligases. Heclin inhibited Nedd4, Smurf2 and WWP1 with IC50 values of 6.3 μM, 6.8 μM and 6.9 μM, respectively, and inhibited autoubiquitination of the Smurf2 HECT domain in vivo with an IC50 value of 9 μM. Heclin had no effect on the auto-ubiquitination of the RING domain ligase Mdm2.
Heclin is not effective in inhibiting E1 or E2 proteins.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Jadier Redondo et al.
Neurobiology of learning and memory, 167, 107135-107135 (2019-12-11)
Ubiquitination is involved in synaptic plasticity and memory, but the involvement of HECT E3 ligases in these processes has not yet been established. Here, we bilaterally infused heclin, a specific inhibitor of some of these ligases, into the dorsal hippocampus
O2-dependent protein internalization underlies astrocytic sensing of acute hypoxia by restricting multimodal TRPA1 channel responses
Uchiyama M, et al.
Current Biology, 30(17), 3378-3396 (2020)
Thomas Mund et al.
Proceedings of the National Academy of Sciences of the United States of America, 111(47), 16736-16741 (2014-11-12)
The human genome encodes several hundred E3 ubiquitin ligases containing RING domains, and around 28 containing HECT domains. These enzymes catalyze the transfer of ubiquitin from E2 enzyme thioesters to a huge range of substrates and play crucial roles in
A Nedd4 E3 Ubiquitin Ligase Pathway Inhibits Robo1 Repulsion and Promotes Commissural Axon Guidance across the Midline.
Gorla, et al.
The Journal of Neuroscience, 42, 7547-7561 (2023)
Andrea Gerbino et al.
Scientific reports, 10(1), 10268-10268 (2020-06-26)
The physiological role of the renal ClC-Ka/ClC-K1 channels is to confer a high Cl- permeability to the thin Ascending Limb of Henle (tAL), which in turn is essential for establishing the high osmolarity of the renal medulla that drives water
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service