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

Molecular Formula C14H6O8
Molecular Weight 302.1926
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
The CLUE test. A multiparameter coagulation and fibrinolysis screening test using the platelet aggregometer.
1975 Jan
Inhibition of human immunodeficiency viral replication by tannins and related compounds.
1992 May
Steroid hormone activity of flavonoids and related compounds.
2000 Jul
Effects of lyophilized black raspberries on azoxymethane-induced colon cancer and 8-hydroxy-2'-deoxyguanosine levels in the Fischer 344 rat.
2001
Ellagic acid formation from galloylglucoses by a crude enzyme of Cornus capitata adventitious roots.
2001 Aug
Effect of processing and storage on the antioxidant ellagic acid derivatives and flavonoids of red raspberry (Rubus idaeus) jams.
2001 Aug
An ellagic compound and iridoids from Cornus capitata root cultures.
2001 Aug
Ellagic [correction of ellagica] acid inhibits arylamine N-acetyltransferase activity and DNA adduct formation in human bladder tumor cell lines (T24 and TSGH 8301).
2001 Dec
Modulation of radiation-induced protein kinase C activity by phenolics.
2001 Dec
Antiproliferative constituents in the plant 8. Seeds of Rhynchosia volubilis.
2001 Dec
Flocculation/flotation/ultrafiltration integrated process for the treatment of cork processing wastewaters.
2001 Dec 15
Mut-Test to detect substances suppressing spontaneous mutation due to oxidative damage.
2001 Jan 25
New antioxidant and antimicrobial ellagic acid derivatives from Pteleopsis hylodendron.
2001 Jun
Constituents of Coriaria ruscifolia fruits.
2001 Jun
Quinone isomers of the WS-5995 antibiotics: synthetic antitumor agents that inhibit macromolecule synthesis, block nucleoside transport, induce DNA fragmentation, and decrease the growth and viability of L1210 leukemic cells more effectively than ellagic acid and genistein in vitro.
2001 Jun
Use of methanolysis for the determination of total ellagic and gallic acid contents of wood and food products.
2001 Mar
Identification of hydrolysable tannins in the reaction zone of Eucalyptus nitens wood by high performance liquid chromatography--electrospray ionisation mass spectrometry.
2001 Mar-Apr
In vitro antiplasmodial activity of extracts of Tristaniopsis species and identification of the active constituents: ellagic acid and 3,4,5-trimethoxyphenyl-(6'-O-galloyl)-O-beta-D-glucopyranoside.
2001 May
Cytogenetic effects of propyl gallate in CHO-K1 cells.
2001 Nov 15
Strong antioxidant activity of ellagic acid in mammalian cells in vitro revealed by the comet assay.
2001 Nov-Dec
Phenolic compounds from Miconia myriantha inhibiting Candida aspartic proteases.
2001 Oct
Antibacterial action of several tannins against Staphylococcus aureus.
2001 Oct
Characterization of peroxidase-mediated chlorophyll bleaching in strawberry fruit.
2001 Oct
Aldose reductase inhibitors from the fruits of Caesalpinia ferrea Mart.
2001 Sep
Chemoprevention of heterocyclic amine-induced mammary carcinogenesis in rats.
2002
Phenolic compounds and antioxidant capacity of Georgia-grown blueberries and blackberries.
2002 Apr 10
Influence of cultivar on quality parameters and chemical composition of strawberry fruits grown in Brazil.
2002 Apr 24
In vitro antiplasmodial activity of extracts of Alchornea cordifolia and identification of an active constituent: ellagic acid.
2002 Aug
Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies.
2002 Dec
Evidence for a global inhibitor-induced conformation change on the Ca(2+)-ATPase of sarcoplasmic reticulum from paired inhibitor studies.
2002 Feb 26
Effect of ellagic acid on gastric damage induced in ischemic rat stomachs following ammonia or reperfusion.
2002 Jan 25
One step purification of corilagin and ellagic acid from Phyllanthus urinaria using high-speed countercurrent chromatography.
2002 Jan-Feb
Pharmacologically active ellagitannins from Terminalia myriocarpa.
2002 Jun
Free radical scavengers, anti-inflammatory and analgesic activity of Acaena magellanica.
2002 Jun
Free radical studies of ellagic acid, a natural phenolic antioxidant.
2002 Mar 27
Cytotoxic, hypoglycemic activity and phytochemical analysis of Rubus imperialis (Rosaceae).
2002 Mar-Apr
Ellagic acid and flavonoid antioxidant content of muscadine wine and juice.
2002 May 22
Ellagic acid derivatives and cytotoxic cucurbitacins from Elaeocarpus mastersii.
2002 Sep
Stages of activation of hepatic stellate cells: effects of ellagic acid, an inhibiter of liver fibrosis, on their differentiation in culture.
2003 Dec
Mechanism-based in vitro screening of potential cancer chemopreventive agents.
2003 Feb-Mar
Unique phenolic carboxylic acids from Sanguisorba minor.
2003 Jun
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
Induction of rat hepatic and intestinal UDP-glucuronosyltransferases by naturally occurring dietary anticarcinogens.
2003 Oct
Phenolic compounds and fatty acids from acorns (Quercus spp.), the main dietary constituent of free-ranged Iberian pigs.
2003 Oct 8
Antioxidative capacity of extracts and constituents in Cornus capitata adventitious roots.
2003 Sep 24
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:19:45 UTC 2023
Edited
by admin
on Fri Dec 15 15:19:45 UTC 2023
Record UNII
19YRN3ZS9P
Record Status Validated (UNII)
Record Version
  • Download
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 Fri Dec 15 15:19:45 UTC 2023 , Edited by admin on Fri Dec 15 15:19:45 UTC 2023
DSLD 1236 (Number of products:47)
Created by admin on Fri Dec 15 15:19:45 UTC 2023 , Edited by admin on Fri Dec 15 15:19:45 UTC 2023
Code System Code Type Description
FDA UNII
19YRN3ZS9P
Created by admin on Fri Dec 15 15:19:45 UTC 2023 , Edited by admin on Fri Dec 15 15:19:45 UTC 2023
PRIMARY
CHEBI
4775
Created by admin on Fri Dec 15 15:19:45 UTC 2023 , Edited by admin on Fri Dec 15 15:19:45 UTC 2023
PRIMARY
DRUG BANK
DB08846
Created by admin on Fri Dec 15 15:19:45 UTC 2023 , Edited by admin on Fri Dec 15 15:19:45 UTC 2023
PRIMARY
RXCUI
1043181
Created by admin on Fri Dec 15 15:19:45 UTC 2023 , Edited by admin on Fri Dec 15 15:19:45 UTC 2023
PRIMARY RxNorm
CAS
476-66-4
Created by admin on Fri Dec 15 15:19:45 UTC 2023 , Edited by admin on Fri Dec 15 15:19:45 UTC 2023
PRIMARY
SMS_ID
100000080747
Created by admin on Fri Dec 15 15:19:45 UTC 2023 , Edited by admin on Fri Dec 15 15:19:45 UTC 2023
PRIMARY
EPA CompTox
DTXSID2020557
Created by admin on Fri Dec 15 15:19:45 UTC 2023 , Edited by admin on Fri Dec 15 15:19:45 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-508-3
Created by admin on Fri Dec 15 15:19:45 UTC 2023 , Edited by admin on Fri Dec 15 15:19:45 UTC 2023
PRIMARY
EVMPD
SUB06488MIG
Created by admin on Fri Dec 15 15:19:45 UTC 2023 , Edited by admin on Fri Dec 15 15:19:45 UTC 2023
PRIMARY
MESH
D004610
Created by admin on Fri Dec 15 15:19:45 UTC 2023 , Edited by admin on Fri Dec 15 15:19:45 UTC 2023
PRIMARY
NSC
407286
Created by admin on Fri Dec 15 15:19:45 UTC 2023 , Edited by admin on Fri Dec 15 15:19:45 UTC 2023
PRIMARY
WIKIPEDIA
ELLAGIC ACID
Created by admin on Fri Dec 15 15:19:45 UTC 2023 , Edited by admin on Fri Dec 15 15:19:45 UTC 2023
PRIMARY
NSC
656272
Created by admin on Fri Dec 15 15:19:45 UTC 2023 , Edited by admin on Fri Dec 15 15:19:45 UTC 2023
PRIMARY
HSDB
7574
Created by admin on Fri Dec 15 15:19:45 UTC 2023 , Edited by admin on Fri Dec 15 15:19:45 UTC 2023
PRIMARY
MERCK INDEX
m4872
Created by admin on Fri Dec 15 15:19:45 UTC 2023 , Edited by admin on Fri Dec 15 15:19:45 UTC 2023
PRIMARY Merck Index
PUBCHEM
5281855
Created by admin on Fri Dec 15 15:19:45 UTC 2023 , Edited by admin on Fri Dec 15 15:19:45 UTC 2023
PRIMARY
NCI_THESAURUS
C63641
Created by admin on Fri Dec 15 15:19:45 UTC 2023 , Edited by admin on Fri Dec 15 15:19:45 UTC 2023
PRIMARY
ChEMBL
CHEMBL6246
Created by admin on Fri Dec 15 15:19:45 UTC 2023 , Edited by admin on Fri Dec 15 15:19:45 UTC 2023
PRIMARY
INN
2667
Created by admin on Fri Dec 15 15:19:45 UTC 2023 , Edited by admin on Fri Dec 15 15:19:45 UTC 2023
PRIMARY
Related Record Type Details
METABOLITE ACTIVE -> PARENT
FORMED BY MICROFLORA
PARENT -> METABOLITE
Related Record Type Details
ACTIVE MOIETY