Ellagic Acid

Status : investigational

Category

Antineoplastic Agents

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.

Used

Ellagic acid is being investigated for use in follicular lymphoma, brain injury in intrauterine growth restricted babies, obese adolescents, and solar lentigines.

Mechanism Of Action

The exact mechanism of action of ellagic acid in its different potential indications is still being investigated.

Pharmacodynamics

Ellagic acid’s therapeutic action mostly involves antioxidant and anti-proliferative/anti-cancer effects.

Absorption

After oral consumption, ellagic acid reaches maximum concentrations in about 1 hour.

Clearance

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

Chemical Classification

This compound belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Hydrolyzable tannins

Organic compounds

Phenylpropanoids and polyketides

Tannins

Hydrolyzable tannins

Calculated Property

kind Value Source
logP 1.59 ALOGPS
logS -2.6 ALOGPS
Water Solubility 8.23e-01 g/l ALOGPS
logP 2.32 ChemAxon
IUPAC Name 6,7,13,14-tetrahydroxy-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione ChemAxon
Traditional IUPAC Name ellagic acid ChemAxon
Molecular Weight 302.1926 ChemAxon
Monoisotopic Weight 302.006267168 ChemAxon
SMILES OC1=C(O)C2=C3C(=C1)C(=O)OC1=C3C(=CC(O)=C1O)C(=O)O2 ChemAxon
Molecular Formula C14H6O8 ChemAxon
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 ChemAxon
InChIKey InChIKey=AFSDNFLWKVMVRB-UHFFFAOYSA-N ChemAxon
Polar Surface Area (PSA) 133.52 ChemAxon
Refractivity 70.61 ChemAxon
Polarizability 26.34 ChemAxon
Rotatable Bond Count 0 ChemAxon
H Bond Acceptor Count 6 ChemAxon
H Bond Donor Count 4 ChemAxon
pKa (strongest acidic) 5.54 ChemAxon
pKa (strongest basic) -4.8 ChemAxon
Physiological Charge -2 ChemAxon
Number of Rings 4 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 1 ChemAxon
Ghose Filter 1 ChemAxon
MDDR-Like Rule 0 ChemAxon

Affected organism

Humans and other mammals

Target within organism

  • Carbonic anhydrase 1 : in Human
  • Carbonic anhydrase 2 : in Human
  • Carbonic anhydrase 3 : in Human
  • Carbonic anhydrase 4 : in Human
  • Carbonic anhydrase 5A, mitochondrial : in Human
  • Carbonic anhydrase 5B, mitochondrial : in Human
  • Carbonic anhydrase 6 : in Human
  • Carbonic anhydrase 7 : in Human
  • Carbonic anhydrase 9 : in Human
  • Carbonic anhydrase 12 : in Human
  • Carbonic anhydrase 14 : in Human
  • Casein kinase II subunit alpha : in Human
  • cAMP-dependent protein kinase catalytic subunit alpha : in Human
  • Protein kinase C alpha type : in Human
  • Protein kinase C beta type : in Human
  • Tyrosine-protein kinase SYK : in Human
  • Squalene monooxygenase : in Human