fisetin   Click here for help

GtoPdb Ligand ID: 5182

PDB Ligand
Compound class: Natural product
Comment: Fisetin is a plant flavonoid. It is used as an ingredient in dietary supplements. It has been investigated for potential anti-inflammatory and senolytic-like actions [1]. It is a more potent senolytic than quercetin.

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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 1
Hydrogen bond donors 4
Rotatable bonds 1
Topological polar surface area 111.13
Molecular weight 286.05
XLogP 3.85
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 Oc1ccc2c(c1)oc(c(c2=O)O)c1ccc(c(c1)O)O
Isomeric SMILES Oc1ccc2c(c1)oc(c(c2=O)O)c1ccc(c(c1)O)O
InChI InChI=1S/C15H10O6/c16-8-2-3-9-12(6-8)21-15(14(20)13(9)19)7-1-4-10(17)11(18)5-7/h1-6,16-18,20H
InChI Key XHEFDIBZLJXQHF-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/)
Classification Click here for help
Compound class Natural product
IUPAC Name Click here for help
2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-4H-chromen-4-one
Database Links Click here for help
BitterDB Ligand 882
CAS Registry No. 528-48-3
ChEBI CHEBI:42567
ChEMBL Ligand CHEMBL31574
GtoPdb PubChem SID 178101872
LIPID MAPS LMPK12111566
PubChem CID 5281614
RCSB PDB Ligand FSE
Search Google for chemical match using the InChIKey XHEFDIBZLJXQHF-UHFFFAOYSA-N
Search Google for chemicals with the same backbone XHEFDIBZLJXQHF
UniChem Compound Search for chemical match using the InChIKey XHEFDIBZLJXQHF-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey XHEFDIBZLJXQHF-UHFFFAOYSA-N
Wikipedia Fisetin

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MedChemExpress
Fisetin (links to external site)
Cat. No. HY-N0182
Fisetin (Standard) (links to external site)
Cat. No. HY-N0182R