BBC0403   Click here for help

GtoPdb Ligand ID: 13230

Synonyms: BBC-0403
Compound class: Synthetic organic
Comment: BBC0403 is reported as a inhibitor of bromodomain-containing (BRD) proteins, with some selectivity for BRD2 domains. It has been explored for efficacy as a treatment for osteoarthritis [1]. BBC0403 inhibits NF-κB and MAPK signaling pathways.

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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 7
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 78.38
Molecular weight 382.41
XLogP 1.12
No. Lipinski's rules broken 0

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 CC1=C(C(=CC(=C1)C2=NC3=C(C(=CC(=C3)OC)OC)C(=O)N2)C)OC4COC4
Isomeric SMILES CC=1C=C(C=C(C1OC2COC2)C)C3=NC4=CC(=CC(=C4C(N3)=O)OC)OC
InChI InChI=1S/C21H22N2O5/c1-11-5-13(6-12(2)19(11)28-15-9-27-10-15)20-22-16-7-14(25-3)8-17(26-4)18(16)21(24)23-20/h5-8,15H,9-10H2,1-4H3,(H,22,23,24)
InChI Key AGBJJHZARZYKNH-UHFFFAOYSA-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/)
References
1. Lee H, Nam J, Jang H, Park YS, Son MH, Lee IH, Eyun SI, Yang JH, Jeon J, Yang S. (2024)
BRD2-specific inhibitor, BBC0403, inhibits the progression of osteoarthritis pathogenesis in osteoarthritis-induced C57BL/6 male mice.
Br J Pharmacol, 181 (15): 2528-2544. [PMID:38600628]