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ANXA3 degrader (R)-SL18   Click here for help

GtoPdb Ligand ID: 13779

Synonyms: (+)-SL18
Compound class: Synthetic organic
Comment: (R)-SL18 is reported as a small molecule degrader of annexin A3 (ANXA3) protein, with degradation mediated principally via the ubiquitin-proteasome system (UPS) [1]. It was superseded by ANXA3 degrader 18a5 which has optimised selectivity and improved binding affinity and anti-proliferative effects in target TNBC cancer cells.
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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Click here for structure editor
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 8
Hydrogen bond donors 3
Rotatable bonds 11
Topological polar surface area 203.43
Molecular weight 597.07
XLogP 3.96
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 CN1C2=C(C=CC=C2)C(=N[C@H](C1=O)NC(=S)SCC(=O)NC(=O)NC3=CC(=CC=C3[N+](=O)[O-])Cl)C4=CC=CC=C4
Isomeric SMILES CN1C2=C(C=CC=C2)C(=N[C@@H](NC(=S)SCC(=O)NC(=O)NC3=C(C=CC(Cl)=C3)[N+]([O-])=O)C1=O)C4=CC=CC=C4
InChI InChI=1S/C26H21ClN6O5S2/c1-32-19-10-6-5-9-17(19)22(15-7-3-2-4-8-15)30-23(24(32)35)31-26(39)40-14-21(34)29-25(36)28-18-13-16(27)11-12-20(18)33(37)38/h2-13,23H,14H2,1H3,(H,31,39)(H2,28,29,34,36)/t23-/m0/s1
InChI Key LWZLLHPZXXUHDA-QHCPKHFHSA-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. Liang Y, Min D, Fan H, Liu K, Tu J, He X, Liu B, Zhou L, Liu S, Sun X. (2023)
Discovery of a first-in-class ANXA3 degrader for the treatment of triple-negative breast cancer.
Acta Pharm Sin B, 13 (4): 1686-1698. [PMID:37139408]