birabresib   Click here for help

GtoPdb Ligand ID: 8359

Synonyms: MK-8628 | OTX-015 | OTX015
PDB Ligand
Compound class: Synthetic organic
Comment: OTX015 inhibits interaction between bromodomain and extra-terminal (BET) family of bromodomain-containing proteins (BRDs) BET domains and acetylated histone 4 (AcH4). It is an orally available novel BRD2/3/4 inhibitor with potent preclinical anti-tumour activity [1,4,6,10,12-13]. OTX015 is an analogue of (+)-JQ1.

birabresib is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 120.12
Molecular weight 491.12
XLogP 5.74
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES O=C(CC1N=C(c2ccc(cc2)Cl)c2c(n3c1nnc3C)sc(c2C)C)Nc1ccc(cc1)O
Isomeric SMILES O=C(C[C@@H]1N=C(c2ccc(cc2)Cl)c2c(n3c1nnc3C)sc(c2C)C)Nc1ccc(cc1)O
InChI InChI=1S/C25H22ClN5O2S/c1-13-14(2)34-25-22(13)23(16-4-6-17(26)7-5-16)28-20(24-30-29-15(3)31(24)25)12-21(33)27-18-8-10-19(32)11-9-18/h4-11,20,32H,12H2,1-3H3,(H,27,33)/t20-/m0/s1
InChI Key GNMUEVRJHCWKTO-FQEVSTJZSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
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]-N-(4-hydroxyphenyl)-acetamide dehydrate
International Nonproprietary Names Click here for help
INN number INN
10407 birabresib
Synonyms Click here for help
MK-8628 | OTX-015 | OTX015
Database Links Click here for help
CAS Registry No. 202590-98-5 (source: WHO INN record)
GtoPdb PubChem SID 252166571
PubChem CID 9936746
RCSB PDB Ligand 6JE
Search Google for chemical match using the InChIKey GNMUEVRJHCWKTO-FQEVSTJZSA-N
Search Google for chemicals with the same backbone GNMUEVRJHCWKTO
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UniChem Compound Search for chemical match using the InChIKey GNMUEVRJHCWKTO-FQEVSTJZSA-N
UniChem Connectivity Search for chemical match using the InChIKey GNMUEVRJHCWKTO-FQEVSTJZSA-N

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MedChemExpress
Birabresib (links to external site)
Cat. No. HY-15743