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tasisulam   Click here for help

GtoPdb Ligand ID: 14233

Synonyms: LY-573636 | LY573636
PDB Ligand
Compound class: Synthetic organic
Comment: Tasisulam (LY573636) is an acyl-sulfonamide class compound with anti-tumour activities [2]. It has more recently been reported to behave as a molecular glue degrader of the RBM39 spliceosome protein. This activity proceeds via a proteasome-dependent mechanism that relies on the presence of the cullin RING ligase substrate receptor DCAF15 [1].
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 4
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 96.92
Molecular weight 415.11
XLogP 1.83
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 C1=C(C=C(C(=C1)C(=O)NS(=O)(=O)C2=CC=C(Br)S2)Cl)Cl
Isomeric SMILES O=C(NS(=O)(C1=CC=C(Br)S1)=O)C2=CC=C(Cl)C=C2Cl
InChI InChI=1S/C11H6BrCl2NO3S2/c12-9-3-4-10(19-9)20(17,18)15-11(16)7-2-1-6(13)5-8(7)14/h1-5H,(H,15,16)
InChI Key WWONFUQGBVOKOF-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. Faust TB, Yoon H, Nowak RP, Donovan KA, Li Z, Cai Q, Eleuteri NA, Zhang T, Gray NS, Fischer ES. (2020)
Structural complementarity facilitates E7820-mediated degradation of RBM39 by DCAF15.
Nat Chem Biol, 16 (1): 7-14. [PMID:31686031]
2. Meier T, Uhlik M, Chintharlapalli S, Dowless M, Van Horn R, Stewart J, Blosser W, Cook J, Young D, Ye X et al.. (2011)
Tasisulam sodium, an antitumor agent that inhibits mitotic progression and induces vascular normalization.
Mol Cancer Ther, 10 (11): 2168-78. [PMID:21903607]