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
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
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 |
|||
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 |
---|---|---|---|
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 |
---|---|---|
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 |
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[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 |
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[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 |
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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 |
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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 |
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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 |
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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 |
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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 |
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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 |
|
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
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
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DSLD |
1236 (Number of products:47)
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Code System | Code | Type | Description | ||
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19YRN3ZS9P
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4775
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DB08846
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1043181
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476-66-4
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100000080747
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DTXSID2020557
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207-508-3
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SUB06488MIG
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D004610
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407286
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ELLAGIC ACID
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656272
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7574
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M4872
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PRIMARY | Merck Index | ||
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5281855
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C63641
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CHEMBL6246
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2667
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ACTIVE MOIETY
METABOLITE ACTIVE (PARENT)
PARENT (METABOLITE)