Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Version1.0
Created at2006-05-22 15:12:18 UTC
Updated at2021-08-19 23:59:09 UTC
NP-MRD IDNP0001478
Secondary Accession NumbersNone
Natural Product Identification
Common NameEllagic acid
DescriptionEllagic acid is an 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. It has a role as an antioxidant, a food additive, a plant metabolite, an EC 5.99.1.2 (DNA topoisomerase) inhibitor, an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, an EC 1.14.18.1 (Tyrosinase) inhibitor, an EC 2.3.1.5 (Arylamine N-acetyltransferase) inhibitor, an EC 2.4.1.1 (Glycogen phosphorylase) inhibitor, an EC 2.5.1.18 (Glutathione transferase) inhibitor, an EC 2.7.1.127 (Inositol-trisphosphate 3-kinase) inhibitor, an EC 2.7.1.151 (Inositol-polyphosphate multikinase) inhibitor, an EC 2.7.4.6 (Nucleoside-diphosphate kinase) inhibitor, a skin lightening agent, a fungal metabolite and an EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor. It is an organic heterotetracyclic compound, a cyclic ketone, a lactone, a member of catechols and a polyphenol. It derives from a gallic acid. Ellagic acid, also known as ellagate, 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. The antiproliferative and antioxidant properties of ellagic acid have spurred preliminary research into the potential health benefits of ellagic acid consumption. Ellagic acid's therapeutic action mostly involves antioxidant and anti-proliferative/anti-cancer effects. Ellagic acid is found, on average, in the highest concentration within a few different foods, such as chestnuts, common walnuts, and japanese walnuts and in a lower concentration in whiskies, arctic blackberries, and cloudberries. Ellagic acid has also been detected, but not quantified in several different foods, such as lowbush blueberries, bilberries, guava, strawberry guava, and bog bilberries.
Structure
Data?1628564086
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
Alizarine yellowHMDB
ElagostasineHMDB
EleagateHMDB
Eleagic acidHMDB
Ellagic acid dihydrateHMDB
Ellagic acid hydrateHMDB
GallogenHMDB
LlagateHMDB
Llagic acidHMDB
Acid, benzoaricHMDB
Acid, ellagicHMDB
Ellagic acidPhytoBank
Chemical FormulaC14H6O8
Average Mass302.1940 Da
Monoisotopic Mass302.00627 Da
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
CAS Registry Number476-66-4
SMILES
[H]OC1=C([H])C2=C3C(OC(=O)C4=C([H])C(O[H])=C(O[H])C(OC2=O)=C34)=C1O[H]
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 KeyAFSDNFLWKVMVRB-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, simulated)V.dorna832021-07-26View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, simulated)V.dorna832021-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, experimental)V.dorna832021-08-23View Spectrum
Species
Species of Origin
Species NameSourceReference
Agrimonia pilosa var.japonicaKNApSAcK Database
Azadirachta indicaKNApSAcK Database
Bertholletia excelsaFooDB
Brassica rapa var. rapaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea sativaFooDB
Casuarina cunninghamiana Miq.KNApSAcK Database
Casuarina equisetifolia L.KNApSAcK Database
Coffea arabica L.FooDB
Coffea canephoraFooDB
Combretum yunnanensisKNApSAcK Database
Coriandrum sativum L.FooDB
Cowania mexicanaKNApSAcK Database
Cunonia macrophyllaKNApSAcK Database
Daucus carota ssp. sativusFooDB
Emblica officinalisKNApSAcK Database
Eucalyptus citriodoraKNApSAcK Database
Eugenia crebrinervisKNApSAcK Database
Eugenia gustavioidesKNApSAcK Database
Eugenia jambolanaKNApSAcK Database
Euphorbia hirtaKNApSAcK Database
Fragaria x ananassaFooDB
Geranium sibiricumKNApSAcK Database
Geranium thunbergiiKNApSAcK Database
Juglans ailanthifoliaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Kunzea ambiguaKNApSAcK Database
Lagerstroemia indicaKNApSAcK Database
Lythrum salicariaKNApSAcK Database
Macaranga barteriKNApSAcK Database
Malus pumilaFooDB
Mangifera indicaKNApSAcK Database
Miconia myrianthaKNApSAcK Database
Myrciaria caulifloraKNApSAcK Database
Myriophyllum spicatumKNApSAcK Database
Nymphaea albaKNApSAcK Database
Oenothera biennisFooDB
Pinus roxburghiiKNApSAcK Database
Platycarya strobilaceaKNApSAcK Database
Prunus persicaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Punica granatumKNApSAcK Database
Quercus albaKNApSAcK Database
Quercus infectoriaKNApSAcK Database
Quercus roburKNApSAcK Database
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus idaeus L.KNApSAcK Database
Rubus occidentalisFooDB
Salvia officinalisFooDB
Satureja subspicataKNApSAcK Database
Saxifraga azizoonKNApSAcK Database
Solanum lycopersicum var. lycopersicumFooDB
Syzygium aromaticumKNApSAcK Database
Syzygium cuminiKNApSAcK Database
Taxodium lanceolataKNApSAcK Database
Taxus chinensisKNApSAcK Database
Terminalia chebulaKNApSAcK Database
Terminalia superbaKNApSAcK Database
Trigonella foenum-graecumFooDB
Vaccinium angustifoliumFooDB
Vaccinium corymbosumFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtillusFooDB
Vaccinium oxycoccosFooDB
Vaccinium uliginosumFooDB
VitisFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point> 360 °CNot Available
Boiling Point796.50 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility78280 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.239 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility0.82 g/LALOGPS
logP10(1.59) g/LALOGPS
logP10(2.32) g/LChemAxon
logS10(-2.6) g/LALOGPS
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
HMDB IDHMDB0002899
DrugBank IDDB08846
Phenol Explorer Compound ID417
FoodDB IDFDB012575
KNApSAcK IDC00011153
Chemspider ID4445149
KEGG Compound IDC10788
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEllagic_acid
METLIN ID3430
PubChem Compound5281855
PDB IDNot Available
ChEBI ID4775
Good Scents IDrw1098851
References
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:16601672 ]