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
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
8-[3-(dimethylamino)propoxy]-5-hydroxy-2-phenyl-7-phenylmethoxychromen-4-one
Synonyms Click here for help
compound 18c [PMID: 28987604] | LW213
Database Links Click here for help
ChEMBL Ligand CHEMBL4207919
GtoPdb PubChem SID 434122237
PubChem CID 145978851
Search Google for chemical match using the InChIKey CZZGXKYKSUTFEU-UHFFFAOYSA-N
Search Google for chemicals with the same backbone CZZGXKYKSUTFEU
UniChem Compound Search for chemical match using the InChIKey CZZGXKYKSUTFEU-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey CZZGXKYKSUTFEU-UHFFFAOYSA-N