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Showing metabocard for Ellagic acid (HMDB0002899)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
enzymes (1) Show 1 protein
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:18 UTC
Update Date2020-02-26 21:24:18 UTC
HMDB IDHMDB0002899
Secondary Accession Numbers
  • HMDB02899
Metabolite Identification
Common NameEllagic acid
DescriptionEllagic acid, also known as ellagate or acide ellagique, 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 an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 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. This could make ellagic acid a potential biomarker for the consumption of these foods. ; cranberries; pecans; pomegranates; strawberries; walnuts. ; and other plant foods. Widely distributed in higher plants especies dicotyledons.
Structure
Data?1582752258
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
Alizarine yellowHMDB
ElagostasineHMDB
EleagateHMDB
Eleagic acidHMDB
Ellagic acid dihydrateHMDB
Ellagic acid hydrateHMDB
GallogenHMDB
LlagateHMDB
Llagic acidHMDB
Acid, benzoaricHMDB
Acid, ellagicHMDB
Chemical FormulaC14H6O8
Average Molecular Weight302.194
Monoisotopic Molecular Weight302.006267153
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
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 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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
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 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
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
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
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Fibroblasts
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 417 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 417 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 417 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 417 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 417 details
BloodDetected and Quantified0.067 +/- 0.0056 uMAdult (>18 years old)Both
Normal		 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 417 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 417 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 417 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 417 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 417 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08846
Phenol Explorer Compound ID417
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Ellagic acid → 3,4,5-trihydroxy-6-({6,13,14-trihydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaen-7-yl}oxy)oxane-2-carboxylic aciddetails
Ellagic acid → 3,4,5-trihydroxy-6-({7,13,14-trihydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaen-6-yl}oxy)oxane-2-carboxylic aciddetails