ellagic acid   Click here for help

GtoPdb Ligand ID: 13035

Synonyms: benzoaric acid | eleagic acid
PDB Ligand
Compound class: Natural product
Comment: Ellagic acid is a plant-derived phenolic compound, that is found in cranberries, strawberries, raspberries, pomegranates, and in some vegetables and nuts. Its biological effects [2] have been proposed for therapeutic potential, however there is no scientific evidence that supports clinical efficacy in serious medical conditions (cancer, heart disease). The pharmacological properties of urolithin ellagic acid metabolites have also been reported [1].

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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 8
Hydrogen bond donors 4
Rotatable bonds 0
Topological polar surface area 133.52
Molecular weight 302.19
XLogP 1.1
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=C2C3=C(C(=C1O)O)OC(=O)C4=C3C(=C(C(=C4)O)O)OC2=O
Isomeric SMILES C1=C2C3=C(C(=C1O)O)OC(=O)C4=CC(=C(C(=C43)OC2=O)O)O
InChI InChI=1S/C14H6O8/c15-5-1-3-7-8-4(14(20)22-11(7)9(5)17)2-6(16)10(18)12(8)21-13(3)19/h1-2,15-18H
InChI Key AFSDNFLWKVMVRB-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
Synonyms Click here for help
benzoaric acid | eleagic acid
Database Links Click here for help
ChEBI CHEBI:4775
ChEMBL Ligand CHEMBL6246
GtoPdb PubChem SID 485206156
PubChem CID 5281855
RCSB PDB Ligand REF
Search Google for chemical match using the InChIKey AFSDNFLWKVMVRB-UHFFFAOYSA-N
Search Google for chemicals with the same backbone AFSDNFLWKVMVRB
UniChem Compound Search for chemical match using the InChIKey AFSDNFLWKVMVRB-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey AFSDNFLWKVMVRB-UHFFFAOYSA-N

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MedChemExpress
Ellagic acid (links to external site)
Cat. No. HY-B0183