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

• ChemBase ID: 6080
• Molecular Formular: C14H6O8
• Molecular Mass: 302.19264
• Monoisotopic Mass: 302.00626715
• SMILES: c12c3c4c(oc1=O)c(c(cc4c(=O)oc3c(c(c2)O)O)O)O
• Canonical SMILES: Oc1cc2c(=O)oc3c4c2c(c1O)oc(=O)c4cc(c3O)O
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 6,7,13,14-tetrahydroxy-2,9-dioxatetracyclo[6.6.2.0^4,^1^6.0^1^1,^1^5]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-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-dione; 6,7,13,14-tetrahydroxy-2,9-dioxatetracyclo[6.6.2.0^4,^1^6.0^1^1,^1^5]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione
• IUPAC Traditional name: ellagic acid
• Synonyms: 4,4′,5,5′,6,6′-Hexahydroxydiphenic acid 2,6,2′,6′-dilactone; 2,3,7,8-tetrahydroxychromeno[5,4,3-cde]chromene-5,10-dione; Ellagic acid; Ellagic acid; 4,4',5,5',6,6'-Hexahydroxydiphenic acid 2,6,2',6'-dilactone hydrate; Ellagic acid hydrate; 鞣花酸; 鞣花酸水合物

Database IDs

• CAS Number: 476-66-4
• EC Number: 207-508-3
• MDL Number: MFCD00149494; MFCD00006914
• Beilstein Number: 47549
• Merck Index: 143547
• PubChem SID: 160969505; 24894460; 99444939
• PubChem CID: 5281855
• CHEBI ID: 4775
• CHEMBL: 6246
• Chemspider ID: 4445149
• DrugBank ID: DB08468
• KEGG ID: C10788
• Unique Ingredient Identifier: 19YRN3ZS9P
• Wikipedia Title: Ellagic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 5.538316
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 1.9992744
• LogD (pH = 7.4): -0.53068095
• Log P: 2.3159225
• Molar Refractivity: 70.6076 cm^3
• Polarizability: 27.52004 Å^3
• Polar Surface Area: 133.52 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.59
• LOG S: -2.57
• Solubility (Water): 8.23e-01 g/l

PROPERTIES

Physical Property

• Solubility: 1 M NaOH: soluble10 mg/mL
• Apperance: powder; Yellow powder
• Melting Point: ≥350 °C; 450°C dec.
• Density: 1.67 g/cm3

Safety Information

• Storage Condition: -20°C
• Storage Warning: Air & Light Sensitive
• RTECS: DJ2620000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Topoisomerases
• Gene Information: human ... CSK(1445), DYRK1A(1859), GSK3B(2932), SRC(6714)rat ... Lyn(81515), Syk(25155)

Product Information

• Purity: ≥95% (HPLC); ≥95.0% (HPLC); ≥96.0% (HPCE); 97%, may cont. up to 12% water
• Grade: analytical standard
• Salt Data: Free Base
• Impurities: <12% water; ≤12% water
• Biological Source: from tree bark
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C14H6O8

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)

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.

Sigma Aldrich - 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

Sigma Aldrich - 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

• Andreas Constantinou et al. Nutrition and Cancer.