All Photos(1)
Synonym(s):
N-(4-Acetylphenyl)-3-(5-ethyl-2-furanyl)-2-propenamide
Empirical Formula (Hill Notation):
C17H17NO3
CAS Number:
Molecular Weight:
283.32
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
Quality Level
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
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
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.
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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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)
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
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
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
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)
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