JQ1

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H25ClN4O2S
Molecular Weight	456.988
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=NN=C2[C@H](CC(=O)OC(C)(C)C)N=C(C3=C(SC(C)=C3C)N12)C4=CC=C(Cl)C=C4

InChI

InChIKey=DNVXATUJJDPFDM-KRWDZBQOSA-N

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

HIDE SMILES / InChI

Molecular Formula	C23H25ClN4O2S
Molecular Weight	456.988
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20871596
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24751816 | https://www.ncbi.nlm.nih.gov/pubmed/22064391

(+)-JQ1 is a selective and potent inhibitor of Bromodomain and Extra-Terminal motif (BET) proteins. These are important epigenetic regulators facilitating the transcription of genes in chromatin areas linked to acetylated histones. (+)-JQ1 engages the bromodomain pocket in a manner that is competitive with acetylated peptide binding, thereby causing the displacement of BET proteins from chromatin. However, the inhibitor’s half life is only one hour, so it has short-lasting effects.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Bromodomain-containing protein 4 13 Target ID: CHEMBL1163125 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20871596\|https://www.ncbi.nlm.nih.gov/pubmed/22316554	Inhibitor 8297	33.0 nM [IC50]
Bromodomain-containing protein 4 13 Target ID: CHEMBL1163125 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20871596	Inhibitor 8297	49.0 nM [Kd]
Bromodomain-containing protein 2 7 Target ID: CHEMBL1293289 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20871596	Inhibitor 8297	128.4 nM [Kd]
Bromodomain-containing protein 3 7 Target ID: CHEMBL1795186 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20871596	Inhibitor 8297	59.5 nM [Kd]
Bromodomain testis-specific protein 1 Target ID: CHEMBL1795185 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20871596	Inhibitor 8297	190.1 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Selective inhibition of BET bromodomains.	2010 Dec 23	20871596

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

JQ1 displaces BET domain containing proteins such as BRD4 from nuclear chromatin in vitro, induces squamous cell differentiation and growth arrest in NUT midline carcinoma (NMC) cells and exhibits antitumour activity in xenograft models of NMC. (+)-JQ1 binds to BRD4-BD1 with a Kd of approximately 50 nM and to BRD4-BD2 with a Kd of 90 nM.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 02:27:51 GMT 2023` Edited by `admin` on `Sat Dec 16 02:27:51 GMT 2023`
Record UNII	1MRH0IMX0W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

JQ1

Code

English

(S)-JQ1

Code

English

JQ-1

Code

English

(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

Systematic Name

English

TERT-BUTYL 2-((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

Systematic Name

English

(+)-JQ1

Code

English

6H-THIENO(3,2-F)(1,2,4)TRIAZOLO(4,3-A)(1,4)DIAZEPINE-6-ACETIC ACID, 4-(4-CHLOROPHENYL)-2,3,9-TRIMETHYL-, 1,1-DIMETHYLETHYL ESTER, (6S)-

Systematic Name

English

Code System Code Type Description

FDA UNII

1MRH0IMX0W