Record Information
Version1.0
Creation date2010-04-08 22:10:15 UTC
Update date2018-05-28 23:37:57 UTC
Primary IDFDB012575
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEllagic acid
DescriptionWidely distributed in higher plants especies dicotyledons. Intestinal astringent, dietary role disputed. Nutriceutical with anticancer and antioxidation props. Ellagic acid is a Polyphenol compound found in numerous fruits and vegetables, including, raspberries; Ellagic acid is a polyphenol antioxidant found in numerous fruits and vegetables including raspberries, strawberries, cranberries, walnuts, pecans, pomegranates and other plant foods. The antiproliferative and antioxidant properties of ellagic acid have spurred preliminary research into the potential health benefits of ellagic acid consumption.; 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.; cranberries; pecans; pomegranates; strawberries; walnuts.
CAS Number476-66-4
Structure
Thumb
Synonyms
SynonymSource
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
Alizarine yellowHMDB
ElagostasineHMDB
EleagateHMDB
Eleagic acidHMDB
Ellagic acid dihydrateHMDB
Ellagic acid hydrateHMDB
GallogenHMDB
LlagateHMDB
Llagic acidHMDB
Acid, benzoaricHMDB
Acid, ellagicHMDB
2,3,7,8-Tetrahydroxy[1]benzopyrano[5,4,3-cde][1]benzopyran-5,10-dione, 9CIdb_source
Alizarin yellowdb_source
Gallogen?db_source
Kajidindb_source
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC14H6O8
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
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
Isomeric SMILESOC1=C(O)C2=C3C(=C1)C(=O)OC1=C3C(=CC(O)=C1O)C(=O)O2
Average Molecular Weight302.194
Monoisotopic Molecular Weight302.006267153
Classification
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 55.64%; H 2.00%; O 42.35%DFC
Melting PointMp 360°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data366 (e 8511) (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uk9-0095000000-fbb3052375510a43a32eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0100-3000090000-98c2eaf6f099a674f556View in MoNA
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
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0zi0-0093000000-8a6cc05fc65249815e82View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0zfr-1589000000-a4f6e3a25012f7426f7dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a6r-0192000000-39923f8b1dd96716ea79View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0090000000-a1f823c8fd710f0476d9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0039000000-911cfbddb0cc618af274View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0zfr-1589000000-a4f6e3a25012f7426f7dView 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 AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID4445149
ChEMBL IDCHEMBL6246
KEGG Compound IDC10788
Pubchem Compound ID5281855
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID417
DrugBank IDDB08846
HMDB IDHMDB02899
CRC / DFC (Dictionary of Food Compounds) IDHJC14-Y:HJC14-Y
EAFUS IDNot Available
Dr. Duke IDELLAGIC-ACID
BIGG IDNot Available
KNApSAcK IDC00011153
HET IDREF
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite ID417
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
abortifacient50691 A chemical substance that interrupts pregnancy after implantation.DUKE
angiotensin converting enzyme inhibitor35457 An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).DUKE
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
anti aflatoxin35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti anaphylactic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti cariogenic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti cataract52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti gingivitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti glucose-tolerance-factorDUKE
anti HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
anti hyperthyroid52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti malarial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti mutagenicDUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti periodonticDUKE
anti peroxidantDUKE
anti plaqueDUKE
anti plasmodial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti streptococcic33282 A substance that kills or slows the growth of bacteria.DUKE
anti thyroidDUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
anti yeast33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
apoptoticDUKE
astringent74783 A compound that causes the contraction of body tissues, typically used to reduce bleeding from minor abrasions.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
Candida-secreted-aspartyl-proteinase inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
deiodinase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
detoxicant50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
glucosyl-transferase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
hemostaticDUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
HIV-reverse-transcriptase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
juvabionalDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
quinone-reductase inducerDUKE
sunscreen52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
topoisomerase-I antagonist50276 A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.DUKE
xanthine oxidase inhibitor35634 An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.