SML1396
Heclin
≥98% (HPLC)
Synonym(s):
N-(4-Acetylphenyl)-3-(5-ethyl-2-furanyl)-2-propenamide
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About This Item
Empirical Formula (Hill Notation):
C17H17NO3
CAS Number:
Molecular Weight:
283.32
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Product Name
Heclin, ≥98% (HPLC)
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
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 20 mg/mL, clear
storage temp.
2-8°C
Quality Level
Related Categories
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
HECT E3 ubiquitin ligase inhibitor
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
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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)
Zeming Zhang et al.
Journal of immunology (Baltimore, Md. : 1950), 204(7), 1904-1918 (2020-02-23)
IFN regulatory factor 3 (IRF3) is critical for the transcription of type I IFNs in defensing virus and promoting inflammatory responses. Although several kinds of posttranslational modifications have been identified to modulate the activity of IRF3, whether atypical ubiquitination participates
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