LW-213   Click here for help

GtoPdb Ligand ID: 11177

Synonyms: compound 18c [PMID: 28987604] | LW213
Compound class: Synthetic organic
Comment: LW-213 is a derivative of the plant flavinoid wogonin [2], and like its parent it has anticancer activity [1,3-4]. Studies in human cutaneous T-cell lymphomas (CTCL) indicate that LW-213-induced apoptosis is mediated via activation of the PERK-eIF2α-ATF4-CHOP axis, and involves enhanced reactive oxygen species production and calcium-dependent endoplasmic reticulum stress. The primary molecular target of LW-213 has not been defined.
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 CDK toolkit. 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 1
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 72.14
Molecular weight 445.19
XLogP 5.96
No. Lipinski's rules broken 1
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.

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Canonical SMILES CN(CCCOc1c(OCc2ccccc2)cc(c2c1oc(cc2=O)c1ccccc1)O)C
Isomeric SMILES CN(CCCOc1c(OCc2ccccc2)cc(c2c1oc(cc2=O)c1ccccc1)O)C
InChI InChI=1S/C27H27NO5/c1-28(2)14-9-15-31-26-24(32-18-19-10-5-3-6-11-19)17-22(30)25-21(29)16-23(33-27(25)26)20-12-7-4-8-13-20/h3-8,10-13,16-17,30H,9,14-15,18H2,1-2H3
InChI Key CZZGXKYKSUTFEU-UHFFFAOYSA-N
References
1. Liu X, Hu P, Li H, Yu XX, Wang XY, Qing YJ, Wang ZY, Wang HZ, Zhu MY, Guo QL et al.. (2020)
LW-213, a newly synthesized flavonoid, induces G2/M phase arrest and apoptosis in chronic myeloid leukemia.
Acta Pharmacol Sin, 41 (2): 249-259. [PMID:31316178]
2. Wang J, Ge R, Qiu X, Xu X, Wei L, Li Z, Bian J. (2017)
Discovery and synthesis of novel Wogonin derivatives with potent antitumor activity in vitro.
Eur J Med Chem, 140: 421-434. [PMID:28987604]
3. Yu XX, Zhu MY, Wang JR, Li H, Hu P, Qing YJ, Wang XY, Wang HZ. (2020)
LW-213 induces cell apoptosis in human cutaneous T-cell lymphomas by activating PERK-eIF2α-ATF4-CHOP axis.
Acta Pharmacol Sin,. DOI: 10.1038/s41401-020-0466-7 [PMID:32747719]
4. Zhao L, Miao HC, Li WJ, Sun Y, Huang SL, Li ZY, Guo QL. (2016)
LW-213 induces G2/M cell cycle arrest through AKT/GSK3β/β-catenin signaling pathway in human breast cancer cells.
Mol Carcinog, 55 (5): 778-92. [PMID:25945460]