U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C14H6O8
Molecular Weight 302.1926
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ELLAGIC ACID

SMILES

OC1=C(O)C2=C3C(=C1)C(=O)OC4=C3C(=CC(O)=C4O)C(=O)O2

InChI

InChIKey=AFSDNFLWKVMVRB-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description

Ellagic acid is a dilactone of hexahydroxydiphenic acid, that found in numerous fruits and vegetables. Ellagic acid was first discovered by chemist Henri Braconnot in 1831. Ellagic acid is found in oaks species like the North American white oak (Quercus alba) and European red oak (Quercus robur). The highest levels of ellagic acid are found in walnuts, pecans, cranberries, raspberries, strawberries, and grapes, as well as distilled beverages. It is also found in peach, and other plant foods. Ellagic acid has antiproliferative and antioxidant properties in a number of in vitro and small-animal models. The antiproliferative properties of ellagic acid may be due to its ability to directly inhibit the DNA binding of certain carcinogens, including nitrosamines and polycyclic aromatic hydrocarbons. As with other polyphenol antioxidants, ellagic acid has a chemoprotective effect in cellular models by reducing oxidative stress. Ellagic acid is an investigational drug studied for treatment of Follicular Lymphoma (phase 2 trial), protection from brain injury of intrauterine growth restricted babies (phase 1 and 2 trial), improvement of cardiovascular function in adolescents who are obese (phase 2 trial), and topical treatment of solar lentigines. Ellagic acid has been marketed as a dietary supplement with a range of claimed benefits against cancer, heart disease, and other medical problems. Ellagic acid has been identified by the U.S. Food and Drug Administration as a "fake cancer 'cure' consumers should avoid".

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
40.0 nM [IC50]
200.0 nM [IC50]
260.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
3.25 ng/mL
13.5 mg 1 times / day multiple, oral
ELLAGIC ACID plasma
Homo sapiens
200.2 ng/mL
40 mg single, oral
ELLAGIC ACID serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
17.61 ng × h/mL
13.5 mg 1 times / day multiple, oral
ELLAGIC ACID plasma
Homo sapiens
1041.8 ng × h/mL
40 mg single, oral
ELLAGIC ACID serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
8.57 h
13.5 mg 1 times / day multiple, oral
ELLAGIC ACID plasma
Homo sapiens
8.4 h
40 mg single, oral
ELLAGIC ACID serum
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
50%
40 mg single, oral
ELLAGIC ACID serum
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Drug as perpetrator​

PubMed

Sample Use Guides

In Vivo Use Guide
The rats were fasted overnight and diabetes was induced by a single dose via intraperitoneal (i.p.) injection of streptozotocin solution (STZ). A total of 32 Wistar Albino rats was used. The rats were randomly divided into four groups, with eight rats each: normal controls (not diabetic), only ellagic acid treated (ellagic acid controls, not diabetic), diabetic control (STZ, diabetic), and ellagic acid treated diabetic (STZ + ellagic acid). The experiment was designed to last a total of 28 days. The dose of the ellagic acid was arranged (50 mg/kg/day orally)
Route of Administration: Oral
In Vitro Use Guide
A total of 2 x 106 cells were seeded in 100 mm plastic dishes and treated with 30mkM Ellagic acid . After 24 h, media was discarded and the cells were washed twice with PBS