Ellagic acid (CHEM016304)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:26:45 UTC
Update Date2016-10-28 10:02:23 UTC
Accession NumberCHEM016304
Identification
Common NameEllagic acid
ClassSmall Molecule
DescriptionAn organic heterotetracyclic compound resulting from the formal dimerisation of gallic acid by oxidative aromatic coupling with intramolecular lactonisation of both carboxylic acid groups of the resulting biaryl. It is found in many fruits and vegetables, including raspberries, strawberries, cranberries, and pomegranates.
Contaminant Sources
  • Cosmetic Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
4,4',5,5',6,6'-Hexahydroxydiphenate 2,6,2',6'-dilactoneGenerator
BenzoarateGenerator
EllagateGenerator
Acid, benzoaricMeSH
Acid, ellagicMeSH
Alizarine yellowHMDB
ElagostasineHMDB
EleagateHMDB
Eleagic acidHMDB
Ellagic acid dihydrateHMDB
Ellagic acid hydrateHMDB
GallogenHMDB
LlagateHMDB
Llagic acidHMDB
Ellagic acidPhytoBank
Chemical FormulaC14H6O8
Average Molecular Mass302.194 g/mol
Monoisotopic Mass302.006 g/mol
CAS Registry Number476-66-4
IUPAC Name6,7,13,14-tetrahydroxy-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione
Traditional Name6,7,13,14-tetrahydroxy-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione
SMILESOC1=C(O)C2=C3C(=C1)C(=O)OC1=C3C(=CC(O)=C1O)C(=O)O2
InChI IdentifierInChI=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 KeyAFSDNFLWKVMVRB-UHFFFAOYSA-N
Chemical Taxonomy
Description 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 (in some cases, shikimic acid units) that 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
  • Coumarin
  • Isocoumarin
  • Benzopyran
  • 2-benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.82 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 Area133.52 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity70.61 m³·mol⁻¹ChemAxon
Polarizability26.34 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uk9-0095000000-fbb3052375510a43a32eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0100-3000090000-98c2eaf6f099a674f556Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0009000000-40fcade2aa63aa93a2aeSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0zi0-0192000000-778eac8f3ed58bcaac74Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0zi0-0093000000-8a6cc05fc65249815e82Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0zfr-1589000000-a4f6e3a25012f7426f7dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a6r-0192000000-39923f8b1dd96716ea79Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0090000000-a1f823c8fd710f0476d9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0039000000-911cfbddb0cc618af274Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0zfr-1589000000-a4f6e3a25012f7426f7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-67c5a949d6d186ed40d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0039000000-d2f61e8b5cdaa0f142baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0090000000-961daa97dff240069d92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0029000000-246b5797e3aacdc8f2f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0059000000-cc29f1c85d471f50bb6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-114i-0190000000-6c3c3d5d2c468609b612Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-9600b3c9d9dcbf3cca2aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0029000000-9f6b76087b40406d9ff3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0090000000-e7359efe114a8fa3c0e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-49d4f264ad1b5c5b0fffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0009000000-49d4f264ad1b5c5b0fffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6s-0090000000-6cad49e11cb1c2a2c0eeSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB08846
HMDB IDHMDB0002899
FooDB IDFDB012575
Phenol Explorer ID417
KNApSAcK IDC00011153
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID3430
PDB IDNot Available
Wikipedia LinkEllagic_acid
Chemspider ID4445149
ChEBI ID4775
PubChem Compound ID5281855
Kegg Compound IDC10788
YMDB IDYMDB01679
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10445164
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10999626
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11902978
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15659385
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=15936648
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=16317787
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=17379263
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=17940513
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=18155344
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=19015354
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=19684079
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=20034460
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=21922312
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22173652
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22538930
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=22626975
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=23058930
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=23060566
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=23092326
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=23322372
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=25438234
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=7644381
23. 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.
24. 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.
25. 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.
26. 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.
27. 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.
28. 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.