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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
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".

CNS Activity

Originator

Approval Year

1912
10
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 40.0 nM [IC50]
Inhibitor
8504
 200.0 nM [IC50]
Inhibitor
8504
 260.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Not Provided
511
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.25 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/16172180
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
EXPERIMENT
https://scialert.net/abstract/?doi=pjn.2009.1661.1664
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/16172180
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
EXPERIMENT
https://scialert.net/abstract/?doi=pjn.2009.1661.1664
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/16172180
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
EXPERIMENT
https://scialert.net/abstract/?doi=pjn.2009.1661.1664
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%
EXPERIMENT
https://scialert.net/abstract/?doi=pjn.2009.1661.1664
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

Other InhibitorOther SubstrateOther Inducer
CYP2E1
1060

CYP1A1
132

CYP2B1
14

CYP3A1/2
1

OAT1
725

OAT4
150

P-gp
1741

BCRP
910
CYP1A1
151

UGT1A10
9
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
BCRP
985
 no
CYP3A1/2
4
 no
P-gp
1932
 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
OAT4
150
 weak [Inhibition 35 uM]
OAT1
730
 yes [IC50 0.207 uM]
CYP1A1
272
 yes [Inhibition 100 uM]
CYP2B1
41
 yes [Inhibition 100 uM]
CYP2E1
1146
 yes [Inhibition 100 uM]
CYP1A1
272
 yes
UGT1A10
46
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:4775
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4775
ChemicalBook
CB6214708
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6214708
eMolecules
509332
https://www.emolecules.com/cgi-bin/more?vid=509332
MolPort
MolPort-000-861-050
https://www.molport.com/shop/molecule-link/MolPort-000-861-050
Selleck Chemicals
Ellagic-acid
http://www.selleckchem.com/products/Ellagic-acid.html
ZINC
ZINC000003872446
http://zinc15.docking.org/substances/ZINC000003872446
PubMed

PubMed

TitleDatePubMed
Antimicrobial activity of Rubus chamaemorus leaves.
2004-01
Stages of activation of hepatic stellate cells: effects of ellagic acid, an inhibiter of liver fibrosis, on their differentiation in culture.
2003-12
Pharmacokinetic study of ellagic acid in rat after oral administration of pomegranate leaf extract.
2003-10-25
Determination of immunological activity in vitro of some plant raw materials.
2003-10-15
Phenolic compounds and fatty acids from acorns (Quercus spp.), the main dietary constituent of free-ranged Iberian pigs.
2003-10-08
Induction of rat hepatic and intestinal UDP-glucuronosyltransferases by naturally occurring dietary anticarcinogens.
2003-10
Antioxidative capacity of extracts and constituents in Cornus capitata adventitious roots.
2003-09-24
Intestinal epithelial cell accumulation of the cancer preventive polyphenol ellagic acid--extensive binding to protein and DNA.
2003-09-15
Analysis of ellagitannins and conjugates of ellagic acid and quercetin in raspberry fruits by LC-MSn.
2003-09
Phenolic content and antioxidant capacity of muscadine grapes.
2003-08-27
Frontal immunoaffinity chromatography with mass spectrometric detection: a method for finding active compounds from traditional Chinese herbs.
2003-08-15
Effects of tannins on Chinese hamster cell line B14.
2003-08-05
Antioxidant and pro-oxidant effects of tannins in digestive cells of the freshwater mussel Unio tumidus.
2003-08-05
Polyphenols of Melaleuca quinquenervia leaves--pharmacological studies of grandinin.
2003-08
Aldose reductase inhibitors from the nature.
2003-08
Inhibition of metalloproteinase-9 activity and gene expression by polyphenolic compounds isolated from the bark of Tristaniopsis calobuxus (Myrtaceae).
2003-07
Two new ellagic acid rhamnosides from Punica granatum heartwood.
2003-07
[Cloudberry: an important source of ellagic acid, an anti-oxidant].
2003-06-26
Antiprotozoal activity of the constituents of Rubus coriifolius.
2003-06
Unique phenolic carboxylic acids from Sanguisorba minor.
2003-06
Repeated oral administration of high doses of the pomegranate ellagitannin punicalagin to rats for 37 days is not toxic.
2003-05-21
Isolation and synthesis of a new bioactive ellagic acid derivative from Combretum yunnanensis.
2003-05
Effect of naturally occurring plant phenolics on the induction of drug metabolizing enzymes by o-toluidine.
2003-04-15
DNA damaging activity of ellagic acid derivatives.
2003-04-03
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.
2003-04
Identification of natural dyes in archeological Coptic textiles by liquid chromatography with diode array detection.
2003-03-14
Mechanism-based in vitro screening of potential cancer chemopreventive agents.
2003-03-12
Antioxidant activity of Egyptian Eucalyptus camaldulensis var. brevirostris leaf extracts.
2003-02
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.
2003-02
Evaluation of the bioavailability and metabolism in the rat of punicalagin, an antioxidant polyphenol from pomegranate juice.
2003-01
DNA-damaging agents from Crypteronia paniculata.
2002-12
Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies.
2002-12
Two ellagitannins from Punica granatum heartwood.
2002-12
Two new and four known polyphenolics obtained as new cell-cycle inhibitors from Rubus aleaefolius Poir.
2002-12
Alpha-tocopherol decreases superoxide anion release in human monocytes under hyperglycemic conditions via inhibition of protein kinase C-alpha.
2002-10
Ellagic acid derivatives and cytotoxic cucurbitacins from Elaeocarpus mastersii.
2002-09
Effect of freezing and storage on the phenolics, ellagitannins, flavonoids, and antioxidant capacity of red raspberries.
2002-08-28
Ellagitannins, flavonoids, and other phenolics in red raspberries and their contribution to antioxidant capacity and vasorelaxation properties.
2002-08-28
In vitro antiplasmodial activity of extracts of Alchornea cordifolia and identification of an active constituent: ellagic acid.
2002-08
Inhibition of cancer cell growth by crude extract and the phenolics of Terminalia chebula retz. fruit.
2002-08
Protection against dextran sulfate sodium-induced colitis by microspheres of ellagic acid in rats.
2002-07-05
Ellagic acid and ellagitannins affect on sedimentation in muscadine juice and wine.
2002-07-03
Determination of free and total phenolic acids in plant-derived foods by HPLC with diode-array detection.
2002-06-19
Cytotoxic, hypoglycemic activity and phytochemical analysis of Rubus imperialis (Rosaceae).
2002-06-18
Antioxidant activity and phenolic content of Oregon caneberries.
2002-06-05
In vitro anti-Neisseria gonorrhoeae activity of Terminalia macroptera leaves.
2002-06-04
Pharmacologically active ellagitannins from Terminalia myriocarpa.
2002-06
Free radical scavengers, anti-inflammatory and analgesic activity of Acaena magellanica.
2002-06
[Studies on the chemical constituents in the leaves of Cyclocarya paliurus].
2002-01
Inhibition of human immunodeficiency viral replication by tannins and related compounds.
1992-05
Patents

Patents

JP2000016917A
1
JP2000044427A
1
JP2000247866A
6
JP2001002527A
4
JP2001089321A
1
JP2001302543A
3
JP2002128654A
2
JP2002275184A
1
JP2002293737A
5
JP2003081826A
1
JP2003160461A
1
JP2003235451A
1
JP2003267823A
2
JP2003342158A
2
JP2003532634A
66
JP2004002270A
1
JP2004095493A
1
JP2004107262A
3
JP2004115381A
1
JP2004352644A
7
JP2005047817A
1
JP2005120023A
2
JP2005350375A
1
JP2006008615A
2
JP2006089422A
4
JP2006206537A
2
JP2006298800A
3
JP2008001693A
1
JP2009215235A
5
JP2009227609A
1
JP2010195791A
2
JP2011527889A
1
JP5308042B2
5
JPH02212409A
1
JPH02231423A
1
JPH02255686A
1
JPH02269176A
1
JPH0499778A
1
JPH05112441A
8
JPH05331183A
1
JPH08268890A
1
JPS5642600A
1
JPS57175115A
1

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
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:54:10 GMT 2025
Edited
by admin
on Mon Mar 31 17:54:10 GMT 2025
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
NSC-407286
Preferred 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-656272
Code English
Ellagic acid [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C68538
Created by admin on Mon Mar 31 17:54:10 GMT 2025 , Edited by admin on Mon Mar 31 17:54:10 GMT 2025
DSLD 1236 (Number of products:47)
Created by admin on Mon Mar 31 17:54:10 GMT 2025 , Edited by admin on Mon Mar 31 17:54:10 GMT 2025
Code System Code Type Description
FDA UNII
19YRN3ZS9P
Created by admin on Mon Mar 31 17:54:10 GMT 2025 , Edited by admin on Mon Mar 31 17:54:10 GMT 2025
PRIMARY
CHEBI
4775
Created by admin on Mon Mar 31 17:54:10 GMT 2025 , Edited by admin on Mon Mar 31 17:54:10 GMT 2025
PRIMARY
DRUG BANK
DB08846
Created by admin on Mon Mar 31 17:54:10 GMT 2025 , Edited by admin on Mon Mar 31 17:54:10 GMT 2025
PRIMARY
RXCUI
1043181
Created by admin on Mon Mar 31 17:54:10 GMT 2025 , Edited by admin on Mon Mar 31 17:54:10 GMT 2025
PRIMARY RxNorm
CAS
476-66-4
Created by admin on Mon Mar 31 17:54:10 GMT 2025 , Edited by admin on Mon Mar 31 17:54:10 GMT 2025
PRIMARY
SMS_ID
100000080747
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PRIMARY
EPA CompTox
DTXSID2020557
Created by admin on Mon Mar 31 17:54:10 GMT 2025 , Edited by admin on Mon Mar 31 17:54:10 GMT 2025
PRIMARY
ECHA (EC/EINECS)
207-508-3
Created by admin on Mon Mar 31 17:54:10 GMT 2025 , Edited by admin on Mon Mar 31 17:54:10 GMT 2025
PRIMARY
EVMPD
SUB06488MIG
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PRIMARY
MESH
D004610
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PRIMARY
NSC
407286
Created by admin on Mon Mar 31 17:54:10 GMT 2025 , Edited by admin on Mon Mar 31 17:54:10 GMT 2025
PRIMARY
WIKIPEDIA
ELLAGIC ACID
Created by admin on Mon Mar 31 17:54:10 GMT 2025 , Edited by admin on Mon Mar 31 17:54:10 GMT 2025
PRIMARY
NSC
656272
Created by admin on Mon Mar 31 17:54:10 GMT 2025 , Edited by admin on Mon Mar 31 17:54:10 GMT 2025
PRIMARY
HSDB
7574
Created by admin on Mon Mar 31 17:54:10 GMT 2025 , Edited by admin on Mon Mar 31 17:54:10 GMT 2025
PRIMARY
MERCK INDEX
m4872
Created by admin on Mon Mar 31 17:54:10 GMT 2025 , Edited by admin on Mon Mar 31 17:54:10 GMT 2025
PRIMARY Merck Index
PUBCHEM
5281855
Created by admin on Mon Mar 31 17:54:10 GMT 2025 , Edited by admin on Mon Mar 31 17:54:10 GMT 2025
PRIMARY
NCI_THESAURUS
C63641
Created by admin on Mon Mar 31 17:54:10 GMT 2025 , Edited by admin on Mon Mar 31 17:54:10 GMT 2025
PRIMARY
ChEMBL
CHEMBL6246
Created by admin on Mon Mar 31 17:54:10 GMT 2025 , Edited by admin on Mon Mar 31 17:54:10 GMT 2025
PRIMARY
INN
2667
Created by admin on Mon Mar 31 17:54:10 GMT 2025 , Edited by admin on Mon Mar 31 17:54:10 GMT 2025
PRIMARY
Related Record Type Details
Structure of UROLITHIN A
METABOLITE ACTIVE -> PARENT
FORMED BY MICROFLORA
Structure of PUNICALAGIN
PARENT -> METABOLITE
Related Record Type Details
Structure of ELLAGIC ACID
ACTIVE MOIETY
NIH
NCATS
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