CHEBI:85928 - (E)-3-tosylacrylonitrile

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ChEBI Name (E)-3-tosylacrylonitrile
ChEBI ID CHEBI:85928
ChEBI ASCII Name (E)-3-tosylacrylonitrile
Definition A nitrile that is acrylonitrile in which the hydrogen located β,trans to the cyano group is replaced by a tosyl group. It is an inhibitor of cytokine-induced IκB-α phosphorylation in cells.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Margaret Duesbury
Supplier Information
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Formula C10H9NO2S
Net Charge 0
Average Mass 207.24900
Monoisotopic Mass 207.035
InChI InChI=1S/C10H9NO2S/c1-9-3-5-10(6-4-9)14(12,13)8-2-7-11/h2-6,8H,1H3/b8-2+
InChIKey DOEWDSDBFRHVAP-KRXBUXKQSA-N
SMILES Cc1ccc(cc1)S(=O)(=O)\C=C\C#N
Roles Classification
Biological Role(s): EC 2.7.11.10 (IkappaB kinase) inhibitor
An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of IkappaB kinase (EC 2.7.11.10).
EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor
An EC 3.1.3.* (phosphoric monoester hydrolase) inhibitor which interferes with the activity of the enzyme protein tyrosine phosphatases (PTPs), EC 3.1.3.48, involved in the removal of phosphate groups from phosphorylated tyrosine residues on proteins.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Application(s): non-steroidal anti-inflammatory drug
An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
platelet aggregation inhibitor
A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
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ChEBI Ontology
Outgoing (E)-3-tosylacrylonitrile (CHEBI:85928) has role apoptosis inducer (CHEBI:68495)
(E)-3-tosylacrylonitrile (CHEBI:85928) has role EC 2.7.11.10 (IκB kinase) inhibitor (CHEBI:77113)
(E)-3-tosylacrylonitrile (CHEBI:85928) has role EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor (CHEBI:35608)
(E)-3-tosylacrylonitrile (CHEBI:85928) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
(E)-3-tosylacrylonitrile (CHEBI:85928) has role platelet aggregation inhibitor (CHEBI:50427)
(E)-3-tosylacrylonitrile (CHEBI:85928) is a nitrile (CHEBI:18379)
(E)-3-tosylacrylonitrile (CHEBI:85928) is a sulfone (CHEBI:35850)
IUPAC Name
(2E)-3-[(4-methylphenyl)sulfonyl]acrylonitrile
Synonyms Sources
(3E)3-(p-toluenesulfonyl)acrylonitrile ChEBI
(E)-3-(4-methylphenylsulfonyl)-2-propenenenitrile ChEBI
(E)-3-(p-toluenesulfonyl)acrylonitrile ChemIDplus
BAY-11-7082 ChemIDplus
BAY-11-7821 ChemIDplus
Bay-117082 ChEBI
BAY-117821 ChemIDplus
β-(cyanovinyl)-p-tolylsulfone ChemIDplus
Registry Numbers Types Sources
19542-67-7 CAS Registry Number ChemIDplus
2049371 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
12 June 2015