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Record Information
Version3.6
Creation Date2006-05-22 15:12:18 UTC
Update Date2016-02-11 01:05:52 UTC
HMDB IDHMDB02899
Secondary Accession NumbersNone
Metabolite Identification
Common NameEllagic acid
DescriptionEllagic acid is a Polyphenol compound found in numerous fruits and vegetables, including, raspberries; strawberries; cranberries; walnuts; pecans; pomegranates; and other plant foods. It is often regarded as an antioxidant. Ellagic Acid Clinical Tests on cultured human cells also show that Ellagic acid prevents the destruction of the p53 gene by cancer cells. Additional studies suggest that one of the mechanisms by which Ellagic acid inhibits mutagenesis and carcinogenesis is by forming adducts with DNA, thus masking binding sites to be occupied by the mutagen or carcinogen.
Structure
Thumb
Synonyms
ValueSource
2,3,7,8-Tetrahydroxy[1]benzopyrano[5,4,3-cde][1]benzopyran-5,10-dioneChEBI
4,4',5,5',6,6'-Hexahydroxydiphenic acid 2,6,2',6'-dilactoneChEBI
Acide ellagiqueChEBI
acido ElagicoChEBI
Acidum ellagicumChEBI
Benzoaric acidChEBI
EllagsaeureChEBI
LagistaseChEBI
EllagateGenerator
4,4',5,5',6,6'-Hexahydroxydiphenate 2,6,2',6'-dilactoneGenerator
BenzoarateGenerator
Alizarine yellowHMDB
ElagostasineHMDB
EleagateHMDB
Eleagic acidHMDB
Ellagic acid dihydrateHMDB
Ellagic acid hydrateHMDB
GallogenHMDB
LlagateHMDB
Llagic acidHMDB
Chemical FormulaC14H6O8
Average Molecular Weight302.1926
Monoisotopic Molecular Weight302.006267168
IUPAC Name6,7,13,14-tetrahydroxy-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione
Traditional Nameellagic acid
CAS Registry Number476-66-4
SMILES
OC1=C(O)C2=C3C(=C1)C(=O)OC1=C3C(=CC(O)=C1O)C(=O)O2
InChI Identifier
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
InChI KeyInChIKey=AFSDNFLWKVMVRB-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassTannins
Sub ClassHydrolyzable tannins
Direct ParentHydrolyzable tannins
Alternative Parents
Substituents
  • Hydrolyzable tannin
  • Ellagic_acid
  • 7,8-dihydroxycoumarin
  • Isocoumarin
  • Coumarin
  • 2-benzopyran
  • 1-benzopyran
  • Benzopyran
  • 1,2-diphenol
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Polyol
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Plant
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point> 360 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.82 mg/mLALOGPS
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 Area133.52 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity70.61 m3·mol-1ChemAxon
Polarizability26.34 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0009000000-40fcade2aa63aa93a2aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0zi0-0192000000-778eac8f3ed58bcaac74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-67c5a949d6d186ed40d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0039000000-d2f61e8b5cdaa0f142baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0090000000-961daa97dff240069d92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0029000000-246b5797e3aacdc8f2f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0059000000-cc29f1c85d471f50bb6bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-114i-0190000000-6c3c3d5d2c468609b612View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Fibroblasts
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 417
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 417
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 417
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 417
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 417
  • Not Applicable
details
BloodDetected and Quantified0.067 +/- 0.0056 uMAdult (>18 years old)Both
Normal
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 417
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 417
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 417
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 417
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 417
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID417
Phenol Explorer Metabolite ID417
FoodDB IDFDB012575
KNApSAcK IDC00011153
Chemspider ID4445149
KEGG Compound IDC10788
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEllagic acid
NuGOwiki LinkHMDB02899
Metagene LinkHMDB02899
METLIN ID3430
PubChem Compound5281855
PDB IDREF
ChEBI ID4775
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Stoner GD, Sardo C, Apseloff G, Mullet D, Wargo W, Pound V, Singh A, Sanders J, Aziz R, Casto B, Sun X: Pharmacokinetics of anthocyanins and ellagic acid in healthy volunteers fed freeze-dried black raspberries daily for 7 days. J Clin Pharmacol. 2005 Oct;45(10):1153-64. [16172180 ]
  2. Glover D, Warner ED: The CLUE test. A multiparameter coagulation and fibrinolysis screening test using the platelet aggregometer. Am J Clin Pathol. 1975 Jan;63(1):74-80. [1111277 ]
  3. Banzouzi JT, Prado R, Menan H, Valentin A, Roumestan C, Mallie M, Pelissier Y, Blache Y: In vitro antiplasmodial activity of extracts of Alchornea cordifolia and identification of an active constituent: ellagic acid. J Ethnopharmacol. 2002 Aug;81(3):399-401. [12127243 ]
  4. Cerda B, Espin JC, Parra S, Martinez P, Tomas-Barberan FA: The potent in vitro antioxidant ellagitannins from pomegranate juice are metabolised into bioavailable but poor antioxidant hydroxy-6H-dibenzopyran-6-one derivatives by the colonic microflora of healthy humans. Eur J Nutr. 2004 Aug;43(4):205-20. Epub 2004 Jan 6. [15309440 ]
  5. Kaiser B, Fareed J, Hoppensteadt D, Birdsong B, Walenga JM, Markwardt F: Influence of recombinant hirudin and unfractionated heparin on thrombin and factor Xa generation in extrinsic and intrinsic activated systems. Thromb Res. 1992 Jan 15;65(2):157-64. [1579892 ]
  6. Jimenez F, Mitts TF, Liu K, Wang Y, Hinek A: Ellagic and tannic acids protect newly synthesized elastic fibers from premature enzymatic degradation in dermal fibroblast cultures. J Invest Dermatol. 2006 Jun;126(6):1272-80. [16601672 ]