Welcome to DrugBank 4.0! If you prefer, you can still go back to version 3.0.
Identification
NameEllagic Acid
Accession NumberDB08846
Typesmall molecule
Groupsinvestigational
Description

Ellagic acid is present in several fruits such as cranberries, strawberries, raspberries, and pomegranates. In pomegranates, there are several therapeutic compounds but ellagic acid is the most active and abundant. Ellagic acid is also present in vegetables. 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’s therapeutic action mostly involves antioxidant and anti-proliferative effects.

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number476-66-4
WeightAverage: 302.1926
Monoisotopic: 302.006267168
Chemical FormulaC14H6O8
InChI KeyInChIKey=AFSDNFLWKVMVRB-UHFFFAOYSA-N
InChI
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
IUPAC Name
6,7,13,14-tetrahydroxy-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione
SMILES
OC1=C(O)C2=C3C(=C1)C(=O)OC1=C3C(=CC(O)=C1O)C(=O)O2
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassTannins
SubclassHydrolyzable Tannins
Direct parentHydrolyzable Tannins
Alternative parentsIsocoumarins and Derivatives; Coumarins and Derivatives; Benzopyrans; Catechols; Pyranones and Derivatives; Dicarboxylic Acids and Derivatives; Polyols; Polyamines; Enols
Substituentsisocoumarin; coumarin; benzopyran; 1,2-diphenol; phenol derivative; pyranone; dicarboxylic acid derivative; benzene; pyran; polyol; enol; polyamine
Classification descriptionThis compound belongs to the hydrolyzable tannins. These are tannins whose structure is characterized by either ofthe following models
Pharmacology
IndicationEllagic acid is being investigated for use in follicular lymphoma, brain injury in intrauterine growth restricted babies, obese adolescents, and solar lentigines.
PharmacodynamicsEllagic acid's therapeutic action mostly involves antioxidant and anti-proliferative/anti-cancer effects.
Mechanism of actionThe exact mechanism of action of ellagic acid in its different potential indications is still being investigated.
AbsorptionAfter oral consumption, ellagic acid reaches maximum concentrations in about 1 hour.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
Clearance

Ellagic acid is eliminated from the body in about 4 hours.

ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.7199
Blood Brain Barrier + 0.5641
Caco-2 permeable - 0.8307
P-glycoprotein substrate Substrate 0.5382
P-glycoprotein inhibitor I Non-inhibitor 0.9377
P-glycoprotein inhibitor II Non-inhibitor 0.9639
Renal organic cation transporter Non-inhibitor 0.9307
CYP450 2C9 substrate Non-substrate 0.8339
CYP450 2D6 substrate Non-substrate 0.9096
CYP450 3A4 substrate Non-substrate 0.7205
CYP450 1A2 substrate Non-inhibitor 0.5914
CYP450 2C9 substrate Non-inhibitor 0.5591
CYP450 2D6 substrate Non-inhibitor 0.9575
CYP450 2C19 substrate Non-inhibitor 0.8017
CYP450 3A4 substrate Non-inhibitor 0.9078
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9568
Ames test Non AMES toxic 0.9127
Carcinogenicity Non-carcinogens 0.9582
Biodegradation Not ready biodegradable 0.8051
Rat acute toxicity 2.6213 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9721
hERG inhibition (predictor II) Non-inhibitor 0.9152
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting pointGreater than 360°CFrom The Merck Index monographs.
water solubilitySlightly soluble in alcohol or waterFrom The Merck Index monographs.
Predicted Properties
PropertyValueSource
water solubility8.23e-01 g/lALOGPS
logP1.59ALOGPS
logP2.32ChemAxon
logS-2.6ALOGPS
pKa (strongest acidic)5.54ChemAxon
pKa (strongest basic)-4.8ChemAxon
physiological charge-2ChemAxon
hydrogen acceptor count6ChemAxon
hydrogen donor count4ChemAxon
polar surface area133.52ChemAxon
rotatable bond count0ChemAxon
refractivity70.61ChemAxon
polarizability26.34ChemAxon
number of rings4ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
Spectra
References
Synthesis Reference

A)Nierenstein M: The Formation of Ellagic Acid from Galloyl-Glycine by Penicillium. Biochem J. 1915 Jun;9(2):240-4. B)Löwe, Zeitschrift für Chemie, 1868, 4, 603.

General Reference
  1. Seeram NP, Lee R, Heber D: Bioavailability of ellagic acid in human plasma after consumption of ellagitannins from pomegranate (Punica granatum L.) juice. Clin Chim Acta. 2004 Oct;348(1-2):63-8. Pubmed
  2. The Merck Index monographs
External Links
ResourceLink
KEGG CompoundC10788
ChEBI4775
ChEMBL
WikipediaEllagic_acid
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(47.6 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Carbonic anhydrase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Carbonic anhydrase 1 P00915 Details

References:

  1. Innocenti A, Beyza Ozturk Sarikaya S, Gulcin I, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Bioorg Med Chem. 2010 Mar 15;18(6):2159-64. doi: 10.1016/j.bmc.2010.01.076. Epub 2010 Feb 6. Pubmed

2. Carbonic anhydrase 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Carbonic anhydrase 2 P00918 Details

References:

  1. Innocenti A, Beyza Ozturk Sarikaya S, Gulcin I, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Bioorg Med Chem. 2010 Mar 15;18(6):2159-64. doi: 10.1016/j.bmc.2010.01.076. Epub 2010 Feb 6. Pubmed

3. Carbonic anhydrase 3

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Carbonic anhydrase 3 P07451 Details

References:

  1. Innocenti A, Beyza Ozturk Sarikaya S, Gulcin I, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Bioorg Med Chem. 2010 Mar 15;18(6):2159-64. doi: 10.1016/j.bmc.2010.01.076. Epub 2010 Feb 6. Pubmed

4. Carbonic anhydrase 4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Carbonic anhydrase 4 P22748 Details

References:

  1. Innocenti A, Beyza Ozturk Sarikaya S, Gulcin I, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Bioorg Med Chem. 2010 Mar 15;18(6):2159-64. doi: 10.1016/j.bmc.2010.01.076. Epub 2010 Feb 6. Pubmed

5. Carbonic anhydrase 5A, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Carbonic anhydrase 5A, mitochondrial P35218 Details

References:

  1. Innocenti A, Beyza Ozturk Sarikaya S, Gulcin I, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Bioorg Med Chem. 2010 Mar 15;18(6):2159-64. doi: 10.1016/j.bmc.2010.01.076. Epub 2010 Feb 6. Pubmed

6. Carbonic anhydrase 5B, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Carbonic anhydrase 5B, mitochondrial Q9Y2D0 Details

References:

  1. Innocenti A, Beyza Ozturk Sarikaya S, Gulcin I, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Bioorg Med Chem. 2010 Mar 15;18(6):2159-64. doi: 10.1016/j.bmc.2010.01.076. Epub 2010 Feb 6. Pubmed

7. Carbonic anhydrase 6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Carbonic anhydrase 6 P23280 Details

References:

  1. Innocenti A, Beyza Ozturk Sarikaya S, Gulcin I, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Bioorg Med Chem. 2010 Mar 15;18(6):2159-64. doi: 10.1016/j.bmc.2010.01.076. Epub 2010 Feb 6. Pubmed

8. Carbonic anhydrase 7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Carbonic anhydrase 7 P43166 Details

References:

  1. Innocenti A, Beyza Ozturk Sarikaya S, Gulcin I, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Bioorg Med Chem. 2010 Mar 15;18(6):2159-64. doi: 10.1016/j.bmc.2010.01.076. Epub 2010 Feb 6. Pubmed

9. Carbonic anhydrase 9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Carbonic anhydrase 9 Q16790 Details

References:

  1. Innocenti A, Beyza Ozturk Sarikaya S, Gulcin I, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Bioorg Med Chem. 2010 Mar 15;18(6):2159-64. doi: 10.1016/j.bmc.2010.01.076. Epub 2010 Feb 6. Pubmed

10. Carbonic anhydrase 12

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Carbonic anhydrase 12 O43570 Details

References:

  1. Innocenti A, Beyza Ozturk Sarikaya S, Gulcin I, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Bioorg Med Chem. 2010 Mar 15;18(6):2159-64. doi: 10.1016/j.bmc.2010.01.076. Epub 2010 Feb 6. Pubmed

11. Carbonic anhydrase 14

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Carbonic anhydrase 14 Q9ULX7 Details

References:

  1. Innocenti A, Beyza Ozturk Sarikaya S, Gulcin I, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Bioorg Med Chem. 2010 Mar 15;18(6):2159-64. doi: 10.1016/j.bmc.2010.01.076. Epub 2010 Feb 6. Pubmed

12. Casein kinase II subunit alpha

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Casein kinase II subunit alpha P68400 Details

References:

  1. Sekiguchi Y, Nakaniwa T, Kinoshita T, Nakanishi I, Kitaura K, Hirasawa A, Tsujimoto G, Tada T: Structural insight into human CK2alpha in complex with the potent inhibitor ellagic acid. Bioorg Med Chem Lett. 2009 Jun 1;19(11):2920-3. doi: 10.1016/j.bmcl.2009.04.076. Epub 2009 Apr 22. Pubmed
  2. Cozza G, Bonvini P, Zorzi E, Poletto G, Pagano MA, Sarno S, Donella-Deana A, Zagotto G, Rosolen A, Pinna LA, Meggio F, Moro S: Identification of ellagic acid as potent inhibitor of protein kinase CK2: a successful example of a virtual screening application. J Med Chem. 2006 Apr 20;49(8):2363-6. Pubmed

13. cAMP-dependent protein kinase catalytic subunit alpha

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor, competitive

Components

Name UniProt ID Details
cAMP-dependent protein kinase catalytic subunit alpha P17612 Details

References:

  1. Wang BH, Lu ZX, Polya GM: Inhibition of eukaryote serine/threonine-specific protein kinases by piceatannol. Planta Med. 1998 Apr;64(3):195-9. Pubmed

14. Protein kinase C alpha type

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor, competitive

Components

Name UniProt ID Details
Protein kinase C alpha type P17252 Details

References:

  1. Wang BH, Lu ZX, Polya GM: Inhibition of eukaryote serine/threonine-specific protein kinases by piceatannol. Planta Med. 1998 Apr;64(3):195-9. Pubmed

15. Protein kinase C beta type

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor, competitive

Components

Name UniProt ID Details
Protein kinase C beta type P05771 Details

References:

  1. Wang BH, Lu ZX, Polya GM: Inhibition of eukaryote serine/threonine-specific protein kinases by piceatannol. Planta Med. 1998 Apr;64(3):195-9. Pubmed

16. Tyrosine-protein kinase SYK

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Tyrosine-protein kinase SYK P43405 Details

References:

  1. Cozza G, Bonvini P, Zorzi E, Poletto G, Pagano MA, Sarno S, Donella-Deana A, Zagotto G, Rosolen A, Pinna LA, Meggio F, Moro S: Identification of ellagic acid as potent inhibitor of protein kinase CK2: a successful example of a virtual screening application. J Med Chem. 2006 Apr 20;49(8):2363-6. Pubmed

17. Squalene monooxygenase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Squalene monooxygenase Q14534 Details

References:

  1. Abe I, Kashiwagi Y, Noguchi H, Tanaka T, Ikeshiro Y, Kashiwada Y: Ellagitannins and hexahydroxydiphenoyl esters as inhibitors of vertebrate squalene epoxidase. J Nat Prod. 2001 Aug;64(8):1010-4. Pubmed

1. Cytochrome P450 1A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor inducer

Components

Name UniProt ID Details
Cytochrome P450 1A1 P04798 Details

References:

  1. Gonzalez-Sarrias A, Azorin-Ortuno M, Yanez-Gascon MJ, Tomas-Barberan FA, Garcia-Conesa MT, Espin JC: Dissimilar in vitro and in vivo effects of ellagic acid and its microbiota-derived metabolites, urolithins, on the cytochrome P450 1A1. J Agric Food Chem. 2009 Jun 24;57(12):5623-32. doi: 10.1021/jf900725e. Pubmed
  2. Barch DH, Rundhaugen LM, Thomas PE, Kardos P, Pillay NS: Dietary ellagic acid inhibits the enzymatic activity of CYP1A1 without altering hepatic concentrations of CYP1A1 or CYP1A1 mRNA. Biochem Biophys Res Commun. 1994 Jun 30;201(3):1477-82. Pubmed

2. Cytochrome P450 2E1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2E1 P05181 Details

References:

  1. Ahn D, Putt D, Kresty L, Stoner GD, Fromm D, Hollenberg PF: The effects of dietary ellagic acid on rat hepatic and esophageal mucosal cytochromes P450 and phase II enzymes. Carcinogenesis. 1996 Apr;17(4):821-8. Pubmed

1. Solute carrier family 22 member 6

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Solute carrier family 22 member 6 Q4U2R8 Details

References:

  1. Whitley AC, Sweet DH, Walle T: The dietary polyphenol ellagic acid is a potent inhibitor of hOAT1. Drug Metab Dispos. 2005 Aug;33(8):1097-100. Epub 2005 May 3. Pubmed

2. Solute carrier family 22 member 11

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Solute carrier family 22 member 11 Q9NSA0 Details

References:

  1. Whitley AC, Sweet DH, Walle T: The dietary polyphenol ellagic acid is a potent inhibitor of hOAT1. Drug Metab Dispos. 2005 Aug;33(8):1097-100. Epub 2005 May 3. Pubmed

Comments
Drug created on February 27, 2013 15:37 / Updated on September 16, 2013 18:11