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
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
DescriptionSources: https://www.drugbank.ca/drugs/DB08846Curator'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".
Sources: https://www.drugbank.ca/drugs/DB08846
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3629 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19414254 |
40.0 nM [IC50] | ||
Target ID: CHEMBL1900 Sources: http://www.ncbi.nlm.nih.gov/pubmed/22377675 |
200.0 nM [IC50] | ||
Target ID: CHEMBL4128 Sources: http://www.ncbi.nlm.nih.gov/pubmed/22377675 |
260.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/8625497/ Page: 1.0 |
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 |
|||
Sources: https://pubmed.ncbi.nlm.nih.gov/15870380/ Page: 3.0 |
weak [Inhibition 35 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15870380/ Page: 3.0 |
yes [IC50 0.207 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/8625497/ Page: 1.0 |
yes [Inhibition 100 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/8625497/ Page: 1.0 |
yes [Inhibition 100 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/8625497/ Page: 1.0 |
yes [Inhibition 100 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/19469472/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/19469472/ |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Inhibition of human immunodeficiency viral replication by tannins and related compounds. | 1992 May |
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[Screening test on protein C]. | 2001 Mar |
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In vitro antiplasmodial activity of extracts of Alchornea cordifolia and identification of an active constituent: ellagic acid. | 2002 Aug |
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Inhibition of cancer cell growth by crude extract and the phenolics of Terminalia chebula retz. fruit. | 2002 Aug |
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Effect of freezing and storage on the phenolics, ellagitannins, flavonoids, and antioxidant capacity of red raspberries. | 2002 Aug 28 |
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Ellagitannins, flavonoids, and other phenolics in red raspberries and their contribution to antioxidant capacity and vasorelaxation properties. | 2002 Aug 28 |
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DNA-damaging agents from Crypteronia paniculata. | 2002 Dec |
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Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies. | 2002 Dec |
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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 |
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[Studies on the chemical constituents in the leaves of Cyclocarya paliurus]. | 2002 Jan |
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Ellagic acid and ellagitannins affect on sedimentation in muscadine juice and wine. | 2002 Jul 3 |
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Protection against dextran sulfate sodium-induced colitis by microspheres of ellagic acid in rats. | 2002 Jul 5 |
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Pharmacologically active ellagitannins from Terminalia myriocarpa. | 2002 Jun |
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Free radical scavengers, anti-inflammatory and analgesic activity of Acaena magellanica. | 2002 Jun |
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Determination of free and total phenolic acids in plant-derived foods by HPLC with diode-array detection. | 2002 Jun 19 |
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In vitro anti-Neisseria gonorrhoeae activity of Terminalia macroptera leaves. | 2002 Jun 4 |
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Cytotoxic, hypoglycemic activity and phytochemical analysis of Rubus imperialis (Rosaceae). | 2002 Mar-Apr |
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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 |
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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 |
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Phenolic content and antioxidant capacity of muscadine grapes. | 2003 Aug 27 |
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Effects of tannins on Chinese hamster cell line B14. | 2003 Aug 5 |
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Antioxidant and pro-oxidant effects of tannins in digestive cells of the freshwater mussel Unio tumidus. | 2003 Aug 5 |
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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 |
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Mechanism-based in vitro screening of potential cancer chemopreventive agents. | 2003 Feb-Mar |
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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 |
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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 |
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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
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21922312
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18848760
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
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Classification Tree | Code System | Code | ||
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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
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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
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Code System | Code | Type | Description | ||
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19YRN3ZS9P
Created by
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PRIMARY | |||
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DB08846
Created by
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PRIMARY | |||
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1043181
Created by
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PRIMARY | RxNorm | ||
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476-66-4
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PRIMARY | |||
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476-66-4
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PRIMARY | |||
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207-508-3
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PRIMARY | |||
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SUB06488MIG
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PRIMARY | |||
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D004610
Created by
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PRIMARY | |||
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ELLAGIC ACID
Created by
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PRIMARY | |||
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7574
Created by
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PRIMARY | |||
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M4872
Created by
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PRIMARY | Merck Index | ||
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5281855
Created by
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PRIMARY | |||
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C63641
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CHEMBL6246
Created by
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PRIMARY | |||
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2667
Created by
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PRIMARY |
ACTIVE MOIETY
METABOLITE ACTIVE (PARENT)