ellagic acid   Click here for help

GtoPdb Ligand ID: 13035

Synonyms: benzoaric acid | eleagic acid
PDB Ligand
Compound class: Natural product or derivative
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].
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
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
SMILES / InChI / InChIKey
Click here for help

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.

✖
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
References
1. Li J, Liao R, Zhang S, Weng H, Liu Y, Tao T, Yu F, Li G, Wu J. (2023)
Promising remedies for cardiovascular disease: Natural polyphenol ellagic acid and its metabolite urolithins.
Phytomedicine, 116: 154867. [PMID:37257327]
2. Seeram NP, Adams LS, Henning SM, Niu Y, Zhang Y, Nair MG, Heber D. (2005)
In vitro antiproliferative, apoptotic and antioxidant activities of punicalagin, ellagic acid and a total pomegranate tannin extract are enhanced in combination with other polyphenols as found in pomegranate juice.
J Nutr Biochem, 16 (6): 360-7. [PMID:15936648]
3. Wang HR, Sui HC, Zhu BT. (2019)
Ellagic acid, a plant phenolic compound, activates cyclooxygenase-mediated prostaglandin production.
Exp Ther Med, 18 (2): 987-996. [PMID:31316596]