CHEBI:137113 - JQ1

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ChEBI Name JQ1
ChEBI ID CHEBI:137113
Definition A member of the class of thienotriazolodiazepines that is the tert-butyl ester of [(6S)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl]acetic acid. An inhibitor of bromodomain-containing protein 4 that exhibits anti-cancer and cardioprotective properties.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:95080
Supplier Information ChemicalBook:CB5102710, eMolecules:481568, ZINC000001532577
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JQ1 is a thienotriazolodiazepine and a potent inhibitor of the BET family of bromodomain proteins which include BRD2, BRD3, BRD4, and the testis-specific protein BRDT in mammals. BET inhibitors structurally similar to JQ1 are being tested in clinical trials for a variety of cancers including NUT midline carcinoma. It was developed by the James Bradner laboratory at Brigham and Women's Hospital and named after chemist Jun Qi. The chemical structure was inspired by patent of similar BET inhibitors by Mitsubishi Tanabe Pharma. Structurally it is related to benzodiazepines. While widely used in laboratory applications, JQ1 is not itself being used in human clinical trials because it has a short half life.
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Formula C23H25ClN4O2S
Net Charge 0
Average Mass 456.990
Monoisotopic Mass 456.13867
InChI InChI=1S/C23H25ClN4O2S/c1-12-13(2)31-22-19(12)20(15-7-9-16(24)10-8-15)25-17(11-18(29)30-23(4,5)6)21-27-26-14(3)28(21)22/h7-10,17H,11H2,1-6H3/t17-/m0/s1
InChIKey DNVXATUJJDPFDM-KRWDZBQOSA-N
SMILES C(=O)(OC(C)(C)C)C[C@H]1C=2N(C3=C(C(=N1)C4=CC=C(C=C4)Cl)C(=C(S3)C)C)C(=NN2)C
Roles Classification
Biological Role(s): ferroptosis inducer
Any substance that induces or promotes ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms.
bromodomain-containing protein 4 inhibitor
Any inhibitor of bromodomain-containing protein 4 (BRD4).
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Application(s): cardioprotective agent
Any protective agent that is able to prevent damage to the heart.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
angiogenesis inhibitor
An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
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ChEBI Ontology
Outgoing JQ1 (CHEBI:137113) has role angiogenesis inhibitor (CHEBI:48422)
JQ1 (CHEBI:137113) has role anti-inflammatory agent (CHEBI:67079)
JQ1 (CHEBI:137113) has role antineoplastic agent (CHEBI:35610)
JQ1 (CHEBI:137113) has role apoptosis inducer (CHEBI:68495)
JQ1 (CHEBI:137113) has role bromodomain-containing protein 4 inhibitor (CHEBI:137114)
JQ1 (CHEBI:137113) has role cardioprotective agent (CHEBI:77307)
JQ1 (CHEBI:137113) has role ferroptosis inducer (CHEBI:173085)
JQ1 (CHEBI:137113) is a tert-butyl ester (CHEBI:140402)
JQ1 (CHEBI:137113) is a carboxylic ester (CHEBI:33308)
JQ1 (CHEBI:137113) is a organochlorine compound (CHEBI:36683)
JQ1 (CHEBI:137113) is a thienotriazolodiazepine (CHEBI:84232)
IUPAC Name
tert-butyl [(6S)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl]acetate
Synonyms Sources
(+)-JQ1 ChEBI
(S)-(+)-tert-Butyl 2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno(3,2-f)(1,2,4)triazolo(4,3-a)(1,4)diazepin-6-yl)acetate ChemIDplus
(S)-JQ1 ChemIDplus
JQ1 UniProt
JQ1 Compound ChemIDplus
TEN-010 ChEBI
Manual Xrefs Databases
JQ1 Wikipedia
JQ1 PDBeChem
LSM-6332 LINCS
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Registry Numbers Types Sources
1268524-70-4 CAS Registry Number ChemIDplus
21994154 Reaxys Registry Number Reaxys
Citations Waiting for Citations
Last Modified
08 July 2022