CAS 476-66-4|ellagic acid|2,3,7,8-tetrahydroxychromeno[5,4,3-cde]chromene-5,10-dione|6,7,13,14-tetrahydroxy-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-d...

General Information

Structure

Molecular Formula

C₁₄H₆O₈

Molecular Mass

302.19264

Exact Mass

302.00626715

Charge

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

InChIKey

AFSDNFLWKVMVRB-UHFFFAOYSA-N

Canonic Smiles

Oc1cc2c(=O)oc3c4c2c(c1O)oc(=O)c4cc(c3O)O

Isomeric Smiles

c12c3c4c(oc1=O)c(c(cc4c(=O)oc3c(c(c2)O)O)O)O

Calculated Properties

JChem

Acid pKa

5.538316

H Acceptors

H Donor

LogD (pH = 5.5)

1.9992744

LogD (pH = 7.4)

-0.53068095

Log P

2.3159225

Molar Refractivity

70.6076

Polarizability

27.52004

Polar Surface Area

133.52

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

1.59

LOG S

-2.57

Solubility (Water)

8.23e-01 g/l

Data Source

Names and Identifiers

IUPAC Traditional name

ellagic acid

Synonyms

2,3,7,8-tetrahydroxychromeno[5,4,3-cde]chromene-5,10-dioneEllagic acid4,4′,5,5′,6,6′-Hexahydroxydiphenic acid 2,6,2′,6′-dilactone鞣花酸Ellagic acid鞣花酸水合物4,4',5,5',6,6'-Hexahydroxydiphenic acid 2,6,2',6'-dilactone hydrateEllagic acid hydrate

IUPAC name

6,7,13,14-tetrahydroxy-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione 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 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

Names and Identifiers

Registration numbers

PubChem CID

5281855

PubChem SID

9944493916096950524894460

MDL Number

MFCD00149494MFCD00006914

Beilstein Number

CAS Number

Merck Index

EC Number

CHEBI ID

Unique Ingredient Identifier

Chemspider ID

DrugBank ID

CHEMBL

KEGG ID

Wikipedia Title

Registration numbers

Properties

Pharmacology Properties

Target

Topoisomerases

Gene Information

human ... CSK(1445), DYRK1A(1859), GSK3B(2932), SRC(6714)rat ... Lyn(81515), Syk(25155)

Safety Information

-20°C

Warning

Acute toxicity (oral, dermal, inhalation), category 4

Skin irritation, category 2

Eye irritation, category 2

Skin sensitisation, category 1

Specific Target Organ Toxicity – Single exposure, category 3

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB08468

Drug information: experimental

Selleck Chemicals

S1327

Research Area: Cancer
Biological Activity:
Ellagic acid is a polyphenol antioxidant found in numerous fruits and vegetables. Ellagic acid also has antiproliferative property. Ellagic acid may slow the growth of some tumors caused by certain carcinogens. Ellagic acid can inhibit the two topoisomerases (IC50 was 0.6 and 0.7 μg/ml for topo I and topo II). [1]References on Ellagic acid[1] Nutrition and Cancer , 1995, 23(2)

Wikipedia

Ellagic_acid

Sigma Aldrich

E2250

Biochem/physiol Actions
Commonly occurring plant polyphenol, inhibitor of glutathione S-transferase.1 Used for the assay of factor XIIa in plasma.2 Contact activation in blood coagulation.3
A naturally occurring plant phenol that is a potent antioxidant presumably by acting as a scavenger of oxygen species produced by hydrogen peroxide treatment, and as a protector of the DNA double helix from alkylating agent injury. It therefore has anti-mutagenic and anti-carcinogenic properties. Also reported to inhibit topoisomerases I and II and gyrase.

45140

Biochem/physiol Actions
Commonly occurring plant polyphenol, inhibitor of glutathione S-transferase.1 Used for the assay of factor XIIa in plasma.2 Contact activation in blood coagulation.3

14668

Biochem/physiol Actions
Commonly occurring plant polyphenol, inhibitor of glutathione S-transferase.1 Used for the assay of factor XIIa in plasma.2 Contact activation in blood coagulation.3

Molecule Details

References

PubChem Literature

From Data Sources

• Andreas Constantinou et al. Nutrition and Cancer.

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

ellagic acid

Synonyms

IUPAC name

Registration numbers

PubChem CID

5281855

PubChem SID

9944493916096950524894460

MDL Number

MFCD00149494MFCD00006914

Beilstein Number

CAS Number

Merck Index

EC Number

CHEBI ID

Unique Ingredient Identifier

Chemspider ID

DrugBank ID

CHEMBL

KEGG ID

Wikipedia Title

Molecule Details

DB08468

Drug information: experimental

S1327

E2250

45140

Biochem/physiol Actions
Commonly occurring plant polyphenol, inhibitor of glutathione S-transferase.1 Used for the assay of factor XIIa in plasma.2 Contact activation in blood coagulation.3

14668

Biochem/physiol Actions
Commonly occurring plant polyphenol, inhibitor of glutathione S-transferase.1 Used for the assay of factor XIIa in plasma.2 Contact activation in blood coagulation.3

References

PubChem Literature

From Data Sources

• Andreas Constantinou et al. Nutrition and Cancer.

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

Target

Topoisomerases

Gene Information

human ... CSK(1445), DYRK1A(1859), GSK3B(2932), SRC(6714)rat ... Lyn(81515), Syk(25155)

Safety Information

-20°C

Warning

Acute toxicity (oral, dermal, inhalation), category 4

Skin irritation, category 2

Eye irritation, category 2

Skin sensitisation, category 1

Specific Target Organ Toxicity – Single exposure, category 3

Molecule

ID:6080