Ellagic acid (CED0002193)

Record Information
Version1.0
Creation Date2016-05-22 03:26:45 UTC
Update Date2026-05-14 19:00:05 UTC
Accession NumberCHEM016304
Identification
Common NameEllagic acid
ClassSmall Molecule
Description
Ellagic acid (C14H6O8) is a compound with an average molecular weight of 302.19 g/mol. Ellagic acid belongs to the hydrolyzable tannins, a subclass of tannins within the organic compounds. In industrial applications, it is used as a softener and conditioner, while biologically it functions as an antioxidant (PMC8253632). It is found in or released from 27 recorded sources across several sectors, including energy, oil & gas (lubricants); healthcare, pharmaceuticals & veterinary products (medical devices); textiles, leather & furnishings (carpets and rugs, synthetic textiles); household cleaning & consumer products (tobacco pipes, pipe accessories, ash trays); electrical & electronic equipment (printed circuit boards, batteries, wires and cables, capacitors, cell phones, and 4 more); and food, food processing & cookware (preparation of malt, molasses and treatment of molasses, cellar tools, food contact materials, food packaging, and 4 more). Recorded exposure routes include oral, touch, and inhalation. At the molecular level, there are 20 recorded protein targets for this compound, including its role as an inhibitor of carbonic anhydrase 1 (CA1), carbonic anhydrase 2 (CA2), carbonic anhydrase 3 (CA3), carbonic anhydrase 4 (CA4), and 16 other proteins. Regarding health effects, ellagic acid is associated with inflammation (PMC10812391) and cancer (PMC7589480). However, it exhibits therapeutic effects on obesity (PMC12196537), liver inflammation (PMC12196537), cataract (PMC3731457), inflammation (PMC5330449), cancer (PMC11421477), and breast cancer (PMC13305355). Additionally, it is used as a treatment for male infertility (PMC8523395).
Contaminant Type
  • PFAS
  • Phytotoxin
Chemical Structure
MOLSDFPDBSMILESInChI
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
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0uk9-0095000000-fbb3052375510a43a32eNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0100-3000090000-98c2eaf6f099a674f556Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0009000000-40fcade2aa63aa93a2aeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0zi0-0192000000-778eac8f3ed58bcaac74Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0zi0-0093000000-8a6cc05fc65249815e82Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0zfr-1589000000-a4f6e3a25012f7426f7dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a6r-0192000000-39923f8b1dd96716ea79Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0090000000-a1f823c8fd710f0476d9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0039000000-911cfbddb0cc618af274Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0zfr-1589000000-a4f6e3a25012f7426f7dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0009000000-67c5a949d6d186ed40d5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0039000000-d2f61e8b5cdaa0f142baNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0090000000-961daa97dff240069d92Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0029000000-246b5797e3aacdc8f2f2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0059000000-cc29f1c85d471f50bb6bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-114i-0190000000-6c3c3d5d2c468609b612Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0009000000-9600b3c9d9dcbf3cca2aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0029000000-9f6b76087b40406d9ff3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0090000000-e7359efe114a8fa3c0e3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0009000000-49d4f264ad1b5c5b0fffNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0009000000-49d4f264ad1b5c5b0fffNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a6s-0090000000-6cad49e11cb1c2a2c0eeNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, DMSO, experimental)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2015.0Log mg/kg[1100:3600]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
inflammationassociated_withNot AvailablePMC10812391
inflammationhas_therapeutic_effect_onNot AvailablePMC5330449
cancerassociated_withNot AvailablePMC7589480
cancerhas_therapeutic_effect_onNot AvailablePMC11421477
breast cancerhas_therapeutic_effect_onNot AvailablePMC13305355
liver inflammationhas_therapeutic_effect_onNot AvailablePMC12196537
obesityhas_therapeutic_effect_onNot AvailablePMC12196537
male infertilityis_treatment_forNot AvailablePMC8523395
cataracthas_therapeutic_effect_onNot AvailablePMC3731457
colitisis_treatment_forNot AvailablePMC10135842
Exposure Sources
Source IDSourceSectorReference
7PesticidesAgriculture & land managementNot Available
120Wires and cablesElectrical & Electronic EquipmentNot Available
121Printed circuit boardsElectrical & Electronic EquipmentNot Available
125BatteriesElectrical & Electronic EquipmentNot Available
130SemiconductorsElectrical & Electronic EquipmentNot Available
138LubricantsEnergy, oil & gasNot Available
147Food packagingFood, food processing & cookwareNot Available
174LubricantsIndustrial manufacturing & chemical processingNot Available
234Medical devicesHealthcare, pharmaceuticals & veterinary productsNot Available
451Carpets and RugsTextiles, leather & furnishingsNot Available
454Synthetic textilesTextiles, leather & furnishingsNot Available
490Personal care & cosmeticsNot Available
492Cell phonesElectrical & Electronic EquipmentNot Available
493CapacitorsElectrical & Electronic EquipmentNot Available
494Food contact materialsFood, food processing & cookwareNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
534Still Video CamerasElectrical & Electronic EquipmentNot Available
543Cellar ToolsFood, food processing & cookwareNot Available
546Molasses And Treatment Of MolassesFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
554Ash TraysHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
597ChemosterilantsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Translin-associated protein X structureClick to view 3D structureTranslin-associated protein XQ99598HumansPredicted (SEA)0.0778492
Click to view 3D structureTyrosine-protein kinase LynQ07014Rattus norvegicusPredicted (SEA)0.0778492
Click to view 3D structureTyrosine-protein kinase FgrQ6P6U0Rattus norvegicusPredicted (SEA)0.0778492
Polypeptide N-acetylgalactosaminyltransferase 2 structureClick to view 3D structurePolypeptide N-acetylgalactosaminyltransferase 2Q10471HumansPredicted (SEA)0.0778492
Click to view 3D structureEctonucleoside triphosphate diphosphohydrolase 1P55772Mus musculusPredicted (SEA)0.0778492
Click to view 3D structurePolypeptide N-acetylgalactosaminyltransferase 1Q10472HumansPredicted (SEA)0.155698
Click to view 3D structurePolypeptide N-acetylgalactosaminyltransferase 14Q96FL9HumansPredicted (SEA)0.155698
Click to view 3D structurePolypeptide N-acetylgalactosaminyltransferase 6Q8NCL4HumansPredicted (SEA)0.155698
Polypeptide N-acetylgalactosaminyltransferase 10 structureClick to view 3D structurePolypeptide N-acetylgalactosaminyltransferase 10Q86SR1HumansPredicted (SEA)0.155698
Click to view 3D structurePolypeptide N-acetylgalactosaminyltransferase 3Q14435HumansPredicted (SEA)0.155698
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)9.03051
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)12.2223
Carbonic anhydrase 13 structureClick to view 3D structureCarbonic anhydrase 13Q8N1Q1HumansPredicted (SEA)1.86838
Amine oxidase [flavin-containing] A structureClick to view 3D structureAmine oxidase [flavin-containing] AP21397HumansPredicted (SEA)12.923
Glutathione S-transferase structureClick to view 3D structureGlutathione S-transferaseQ8ILQ7Plasmodium falciparumPredicted (SEA)0.0778492
Click to view 3D structureGag-Pol polyproteinQ7ZJM1Human immunodeficiency virus 1Predicted (SEA)7.55137
Click to view 3D structureAldo-keto reductase family 1 member B1P07943Rattus norvegicusPredicted (SEA)5.52729
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)163.406
Aldo-keto reductase family 1 member B1 structureClick to view 3D structureAldo-keto reductase family 1 member B1P15121HumansPredicted (SEA)7.78492
Serine/threonine-protein kinase PLK1 structureClick to view 3D structureSerine/threonine-protein kinase PLK1P53350HumansPredicted (SEA)65.1598
G-protein coupled receptor 35 structureClick to view 3D structureG-protein coupled receptor 35Q9HC97HumansPredicted (SEA)1.55698
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)35.3435
Casein kinase II subunit alpha structureClick to view 3D structureCasein kinase II subunit alphaP68400HumansPredicted (SEA)45.8532
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)31.4511
Pyruvate kinase PKLR structureClick to view 3D structurePyruvate kinase PKLRP30613HumansPredicted (SEA)0.0778492
Concentrations
Not Available
External Links
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.