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Details

Stereochemistry ACHIRAL
Molecular Formula C14H6O8
Molecular Weight 302.1932
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ELLAGIC ACID

SMILES

c1c2c3c4c(cc(c(c4oc2=O)O)O)c(=O)oc3c(c1O)O

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
Curator's Comment:: 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".

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".

Approval Year

Targets

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.25 ng/mL
13.5 mg 1 times / day multiple, oral
dose: 13.5 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ELLAGIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
200.2 ng/mL
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ELLAGIC ACID serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
17.61 ng × h/mL
13.5 mg 1 times / day multiple, oral
dose: 13.5 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ELLAGIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1041.8 ng × h/mL
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ELLAGIC ACID serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8.57 h
13.5 mg 1 times / day multiple, oral
dose: 13.5 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ELLAGIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
8.4 h
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ELLAGIC ACID serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
50%
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ELLAGIC ACID serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
yes (co-administration study)
Comment: The increase in Cmax, AUC, AUMC, AUCtotal and t1/2 of linagliptin was found to be 2.0-fold, 1.2-fold, 1.74- fold, 1.52-fold and 0.5-fold, respectively, in the EA pretreated group compared with the control group. In vitro experiments showed no inhibition
weak [Inhibition 35 uM]
yes [IC50 0.207 uM]
yes [Inhibition 100 uM]
yes [Inhibition 100 uM]
yes [Inhibition 100 uM]
yes
yes
PubMed

PubMed

TitleDatePubMed
Inhibition of human immunodeficiency viral replication by tannins and related compounds.
1992 May
[Screening test on protein C].
2001 Mar
In vitro antiplasmodial activity of extracts of Alchornea cordifolia and identification of an active constituent: ellagic acid.
2002 Aug
Inhibition of cancer cell growth by crude extract and the phenolics of Terminalia chebula retz. fruit.
2002 Aug
Effect of freezing and storage on the phenolics, ellagitannins, flavonoids, and antioxidant capacity of red raspberries.
2002 Aug 28
Ellagitannins, flavonoids, and other phenolics in red raspberries and their contribution to antioxidant capacity and vasorelaxation properties.
2002 Aug 28
DNA-damaging agents from Crypteronia paniculata.
2002 Dec
Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies.
2002 Dec
Two ellagitannins from Punica granatum heartwood.
2002 Dec
Two new and four known polyphenolics obtained as new cell-cycle inhibitors from Rubus aleaefolius Poir.
2002 Dec
[Studies on the chemical constituents in the leaves of Cyclocarya paliurus].
2002 Jan
Ellagic acid and ellagitannins affect on sedimentation in muscadine juice and wine.
2002 Jul 3
Protection against dextran sulfate sodium-induced colitis by microspheres of ellagic acid in rats.
2002 Jul 5
Pharmacologically active ellagitannins from Terminalia myriocarpa.
2002 Jun
Free radical scavengers, anti-inflammatory and analgesic activity of Acaena magellanica.
2002 Jun
Determination of free and total phenolic acids in plant-derived foods by HPLC with diode-array detection.
2002 Jun 19
In vitro anti-Neisseria gonorrhoeae activity of Terminalia macroptera leaves.
2002 Jun 4
Cytotoxic, hypoglycemic activity and phytochemical analysis of Rubus imperialis (Rosaceae).
2002 Mar-Apr
Alpha-tocopherol decreases superoxide anion release in human monocytes under hyperglycemic conditions via inhibition of protein kinase C-alpha.
2002 Oct
Ellagic acid derivatives and cytotoxic cucurbitacins from Elaeocarpus mastersii.
2002 Sep
Effects of DX-9065a, an inhibitor of factor Xa, on ellagic acid-induced plantar skin thrombosis assessed in tetrodotoxin- and N(omega)-nitro-L-arginine-treated rats.
2003 Apr
Effect of naturally occurring plant phenolics on the induction of drug metabolizing enzymes by o-toluidine.
2003 Apr 15
DNA damaging activity of ellagic acid derivatives.
2003 Apr 3
Polyphenols of Melaleuca quinquenervia leaves--pharmacological studies of grandinin.
2003 Aug
Aldose reductase inhibitors from the nature.
2003 Aug
Frontal immunoaffinity chromatography with mass spectrometric detection: a method for finding active compounds from traditional Chinese herbs.
2003 Aug 15
Phenolic content and antioxidant capacity of muscadine grapes.
2003 Aug 27
Effects of tannins on Chinese hamster cell line B14.
2003 Aug 5
Antioxidant and pro-oxidant effects of tannins in digestive cells of the freshwater mussel Unio tumidus.
2003 Aug 5
Stages of activation of hepatic stellate cells: effects of ellagic acid, an inhibiter of liver fibrosis, on their differentiation in culture.
2003 Dec
Antioxidant activity of Egyptian Eucalyptus camaldulensis var. brevirostris leaf extracts.
2003 Feb
In vitro studies on the mechanism of action of two compounds with antiplasmodial activity: ellagic acid and 3,4,5-trimethoxyphenyl(6'-O-aalloyl)-beta-D-glucopyranoside.
2003 Feb
Mechanism-based in vitro screening of potential cancer chemopreventive agents.
2003 Feb-Mar
Evaluation of the bioavailability and metabolism in the rat of punicalagin, an antioxidant polyphenol from pomegranate juice.
2003 Jan
Inhibition of metalloproteinase-9 activity and gene expression by polyphenolic compounds isolated from the bark of Tristaniopsis calobuxus (Myrtaceae).
2003 Jul
Two new ellagic acid rhamnosides from Punica granatum heartwood.
2003 Jul
Antiprotozoal activity of the constituents of Rubus coriifolius.
2003 Jun
Unique phenolic carboxylic acids from Sanguisorba minor.
2003 Jun
[Cloudberry: an important source of ellagic acid, an anti-oxidant].
2003 Jun 26
Identification of natural dyes in archeological Coptic textiles by liquid chromatography with diode array detection.
2003 Mar 14
Isolation and synthesis of a new bioactive ellagic acid derivative from Combretum yunnanensis.
2003 May
Repeated oral administration of high doses of the pomegranate ellagitannin punicalagin to rats for 37 days is not toxic.
2003 May 21
Determination of immunological activity in vitro of some plant raw materials.
2003 May-Jun
Induction of rat hepatic and intestinal UDP-glucuronosyltransferases by naturally occurring dietary anticarcinogens.
2003 Oct
Pharmacokinetic study of ellagic acid in rat after oral administration of pomegranate leaf extract.
2003 Oct 25
Phenolic compounds and fatty acids from acorns (Quercus spp.), the main dietary constituent of free-ranged Iberian pigs.
2003 Oct 8
Analysis of ellagitannins and conjugates of ellagic acid and quercetin in raspberry fruits by LC-MSn.
2003 Sep
Intestinal epithelial cell accumulation of the cancer preventive polyphenol ellagic acid--extensive binding to protein and DNA.
2003 Sep 15
Antioxidative capacity of extracts and constituents in Cornus capitata adventitious roots.
2003 Sep 24
Antimicrobial activity of Rubus chamaemorus leaves.
2004 Jan
Patents

Sample Use Guides

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
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
Name Type Language
ELLAGIC ACID
HSDB   INCI   INN   MI   WHO-DD  
INN   INCI  
Official Name English
ELLAGIC ACID [MI]
Common Name English
2,3,7,8-TETRAHYDROXY(1)BENZOPYRANO(5,4,3-CDE)-(1)BENZOPYRAN-5,10-DIONE
Systematic Name English
ELLAGIC ACID [INN]
Common Name English
ELLAGIC ACID [HSDB]
Common Name English
NSC-407286
Code English
NSC-656272
Code English
ELLAGIC ACID [WHO-DD]
Common Name English
ELLAGIC ACID [INCI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C68538
Created by admin on Sat Jun 26 16:32:44 UTC 2021 , Edited by admin on Sat Jun 26 16:32:44 UTC 2021
DSLD 1236 (Number of products:47)
Created by admin on Sat Jun 26 16:32:44 UTC 2021 , Edited by admin on Sat Jun 26 16:32:44 UTC 2021
Code System Code Type Description
FDA UNII
19YRN3ZS9P
Created by admin on Sat Jun 26 16:32:44 UTC 2021 , Edited by admin on Sat Jun 26 16:32:44 UTC 2021
PRIMARY
DRUG BANK
DB08846
Created by admin on Sat Jun 26 16:32:44 UTC 2021 , Edited by admin on Sat Jun 26 16:32:44 UTC 2021
PRIMARY
RXCUI
1043181
Created by admin on Sat Jun 26 16:32:44 UTC 2021 , Edited by admin on Sat Jun 26 16:32:44 UTC 2021
PRIMARY RxNorm
CAS
476-66-4
Created by admin on Sat Jun 26 16:32:44 UTC 2021 , Edited by admin on Sat Jun 26 16:32:44 UTC 2021
PRIMARY
EPA CompTox
476-66-4
Created by admin on Sat Jun 26 16:32:44 UTC 2021 , Edited by admin on Sat Jun 26 16:32:44 UTC 2021
PRIMARY
ECHA (EC/EINECS)
207-508-3
Created by admin on Sat Jun 26 16:32:44 UTC 2021 , Edited by admin on Sat Jun 26 16:32:44 UTC 2021
PRIMARY
EVMPD
SUB06488MIG
Created by admin on Sat Jun 26 16:32:44 UTC 2021 , Edited by admin on Sat Jun 26 16:32:44 UTC 2021
PRIMARY
MESH
D004610
Created by admin on Sat Jun 26 16:32:44 UTC 2021 , Edited by admin on Sat Jun 26 16:32:44 UTC 2021
PRIMARY
WIKIPEDIA
ELLAGIC ACID
Created by admin on Sat Jun 26 16:32:44 UTC 2021 , Edited by admin on Sat Jun 26 16:32:44 UTC 2021
PRIMARY
HSDB
7574
Created by admin on Sat Jun 26 16:32:44 UTC 2021 , Edited by admin on Sat Jun 26 16:32:44 UTC 2021
PRIMARY
MERCK INDEX
M4872
Created by admin on Sat Jun 26 16:32:44 UTC 2021 , Edited by admin on Sat Jun 26 16:32:44 UTC 2021
PRIMARY Merck Index
PUBCHEM
5281855
Created by admin on Sat Jun 26 16:32:44 UTC 2021 , Edited by admin on Sat Jun 26 16:32:44 UTC 2021
PRIMARY
NCI_THESAURUS
C63641
Created by admin on Sat Jun 26 16:32:44 UTC 2021 , Edited by admin on Sat Jun 26 16:32:44 UTC 2021
PRIMARY
ChEMBL
CHEMBL6246
Created by admin on Sat Jun 26 16:32:44 UTC 2021 , Edited by admin on Sat Jun 26 16:32:44 UTC 2021
PRIMARY
INN
2667
Created by admin on Sat Jun 26 16:32:44 UTC 2021 , Edited by admin on Sat Jun 26 16:32:44 UTC 2021
PRIMARY