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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
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
Steroid hormone activity of flavonoids and related compounds.
2000 Jul
Ellagic acid inhibits nucleoside diphosphate kinase-B activity.
2001
Ellagic acid inhibited 2-aminofluorene and p-aminobenzoic acid acetylation by mononuclear leucocytes from Sprague-Dawley rats.
2001
Application of Eudragit P-4135F for the delivery of ellagic acid to the rat lower small intestine.
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
Inhibition of cellular transformation by berry extracts.
2001 Feb
Mut-Test to detect substances suppressing spontaneous mutation due to oxidative damage.
2001 Jan 25
IGF-II down regulation associated cell cycle arrest in colon cancer cells exposed to phenolic antioxidant ellagic acid.
2001 Jan-Feb
Ellagic acid rhamnosides from the stem bark of Eucalyptus globulus.
2001 Jun
[Screening test on protein C].
2001 Mar
Use of methanolysis for the determination of total ellagic and gallic acid contents of wood and food products.
2001 Mar
[Antioxidant properties of novel preparations--bioflavonoid derivatives and tannins].
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
Unusually large numbers of electrons for the oxidation of polyphenolic antioxidants.
2001 May 3
Antibacterial action of several tannins against Staphylococcus aureus.
2001 Oct
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
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
DNA-damaging agents from Crypteronia paniculata.
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
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
Interactive gene expression pattern in prostate cancer cells exposed to phenolic antioxidants.
2002 Mar 1
A rapid screening assay for antioxidant potential of natural and synthetic agents in vitro.
2002 May
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
Effect of naturally occurring plant phenolics on the induction of drug metabolizing enzymes by o-toluidine.
2003 Apr 15
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
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
Determination of immunological activity in vitro of some plant raw materials.
2003 May-Jun
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 Wed Jul 05 22:50:35 UTC 2023 , Edited by admin on Wed Jul 05 22:50:35 UTC 2023
DSLD 1236 (Number of products:47)
Created by admin on Wed Jul 05 22:50:35 UTC 2023 , Edited by admin on Wed Jul 05 22:50:35 UTC 2023
Code System Code Type Description
FDA UNII
19YRN3ZS9P
Created by admin on Wed Jul 05 22:50:35 UTC 2023 , Edited by admin on Wed Jul 05 22:50:35 UTC 2023
PRIMARY
CHEBI
4775
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PRIMARY
DRUG BANK
DB08846
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PRIMARY
RXCUI
1043181
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PRIMARY RxNorm
CAS
476-66-4
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PRIMARY
SMS_ID
100000080747
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PRIMARY
EPA CompTox
DTXSID2020557
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PRIMARY
ECHA (EC/EINECS)
207-508-3
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PRIMARY
EVMPD
SUB06488MIG
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PRIMARY
MESH
D004610
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PRIMARY
NSC
407286
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PRIMARY
WIKIPEDIA
ELLAGIC ACID
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PRIMARY
NSC
656272
Created by admin on Wed Jul 05 22:50:35 UTC 2023 , Edited by admin on Wed Jul 05 22:50:35 UTC 2023
PRIMARY
HSDB
7574
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PRIMARY
MERCK INDEX
M4872
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PRIMARY Merck Index
PUBCHEM
5281855
Created by admin on Wed Jul 05 22:50:35 UTC 2023 , Edited by admin on Wed Jul 05 22:50:35 UTC 2023
PRIMARY
NCI_THESAURUS
C63641
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PRIMARY
ChEMBL
CHEMBL6246
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PRIMARY
INN
2667
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PRIMARY